Privately positioned on a tropical peninsula on Siesta Key in the coveted community of Hidden Harbor, this extraordinary bayfront estate captures sweeping views across Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline. Set on 0.62 acres with 125 feet of panoramic waterfront, the residence was masterfully built by luxury builder M. L. Collingwood and thoughtfully designed to celebrate both architectural craftsmanship and the beauty of its remarkable setting. A protected deep-water harbor, a private 50-foot dock and 20,000-pound lift create an exceptional opportunity for the serious boater, while the home’s privacy, scale and resort-style outdoor living make it equally ideal as a serene waterfront retreat. From the moment you arrive, custom mahogany doors, beveled glass transoms, lush landscaping and a gracious entry introduce the timeless character found throughout the residence. Inside, soaring ceilings, generous room proportions and walls of glass frame magnificent water views from many of the principal living areas. Rich architectural details include coffered and tray ceilings, bentwood arches, crown molding, custom millwork and travertine inset flooring. The formal living and dining rooms flow beautifully for entertaining and are complemented by a fully outfitted cherrywood-paneled bar and wine room. The executive office and library are a showpiece, featuring cherrywood paneling, an 18-foot coffered ceiling and a spiral staircase leading to upper bookshelves. The well-appointed island kitchen offers Wood-Mode cabinetry, quartzite countertops, stainless steel appliances, paneled Sub-Zero refrigeration, a Viking six-burner gas range, dual ovens, a walk-in pantry and a spacious breakfast bar. Open to the bayfront breakfast and gathering rooms, the space features an electric fireplace, adding warmth and ambiance, and connects effortlessly to the outdoor living areas. The primary suite is a private waterfront sanctuary with a bayfront sitting room and a generous bath with dual vanities, a two-person shower, a soaking tub and private water closets. Two additional guest suites are privately positioned in their own wing on the main level, along with a powder bath and laundry room. Upstairs, a fourth bedroom or game room includes a full bath, walk-in closet and private western balcony overlooking the harbor, ideal for taking in evening sunsets. Designed for relaxed Florida living, the expansive lanai features a heated saltwater infinity-edge pool, travertine decking and a shaded outdoor living space with custom ceiling detail, creating an inviting setting for alfresco dining and waterfront entertaining. Frequent dolphin and manatee sightings add to the magic of this rare waterfront setting. Additional features include a side-entry three-car garage, a paver drive and walkways, landscape lighting, a walk-in attic and abundant storage. Hidden Harbor is one of Siesta Key’s most treasured boating communities, offering exceptional privacy just one mile from the powdery white sands of Siesta Beach and close to Siesta Village’s dining, shopping and island charm. Mainland Sarasota’s cultural venues, restaurants, shopping, medical facilities and schools, including nationally acclaimed Pine View School, are also within easy reach.

4 Beds ⋅ 5 Baths ⋅ A4696603 MLS

Privately positioned on a tropical peninsula on Siesta Key in the coveted community of Hidden Harbor, this extraordinary bayfront estate captures sweeping views across Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline. Set on 0.62 acres with 125 feet of panoramic waterfront, the residence was masterfully built by luxury builder M. L. Collingwood and thoughtfully designed to celebrate both architectural craftsmanship and the beauty of its remarkable setting. A protected deep-water harbor, a private 50-foot dock and 20,000-pound lift create an exceptional opportunity for the serious boater, while the home’s privacy, scale and resort-style outdoor living make it equally ideal as a serene waterfront retreat. From the moment you arrive, custom mahogany doors, beveled glass transoms, lush landscaping and a gracious entry introduce the timeless character found throughout the residence. Inside, soaring ceilings, generous room proportions and walls of glass frame magnificent water views from many of the principal living areas. Rich architectural details include coffered and tray ceilings, bentwood arches, crown molding, custom millwork and travertine inset flooring. The formal living and dining rooms flow beautifully for entertaining and are complemented by a fully outfitted cherrywood-paneled bar and wine room. The executive office and library are a showpiece, featuring cherrywood paneling, an 18-foot coffered ceiling and a spiral staircase leading to upper bookshelves. The well-appointed island kitchen offers Wood-Mode cabinetry, quartzite countertops, stainless steel appliances, paneled Sub-Zero refrigeration, a Viking six-burner gas range, dual ovens, a walk-in pantry and a spacious breakfast bar. Open to the bayfront breakfast and gathering rooms, the space features an electric fireplace, adding warmth and ambiance, and connects effortlessly to the outdoor living areas. The primary suite is a private waterfront sanctuary with a bayfront sitting room and a generous bath with dual vanities, a two-person shower, a soaking tub and private water closets. Two additional guest suites are privately positioned in their own wing on the main level, along with a powder bath and laundry room. Upstairs, a fourth bedroom or game room includes a full bath, walk-in closet and private western balcony overlooking the harbor, ideal for taking in evening sunsets. Designed for relaxed Florida living, the expansive lanai features a heated saltwater infinity-edge pool, travertine decking and a shaded outdoor living space with custom ceiling detail, creating an inviting setting for alfresco dining and waterfront entertaining. Frequent dolphin and manatee sightings add to the magic of this rare waterfront setting. Additional features include a side-entry three-car garage, a paver drive and walkways, landscape lighting, a walk-in attic and abundant storage. Hidden Harbor is one of Siesta Key’s most treasured boating communities, offering exceptional privacy just one mile from the powdery white sands of Siesta Beach and close to Siesta Village’s dining, shopping and island charm. Mainland Sarasota’s cultural venues, restaurants, shopping, medical facilities and schools, including nationally acclaimed Pine View School, are also within easy reach.

1280 Hidden Harbor Way, Siesta Key

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY. 941-364-4000

$6,990,000

Start living your dream lifestyle on world-famous Siesta Key in this Pham Development custom-built waterfront British West Indies–style home. Located on a quiet street on the north end of the key—close to the beach, Siesta Key Village and Out-of-Door Academy—and just minutes on and off the island, this residence offers island living at its best. Set on a corner canal-front lot, the two-story home features 5 bedrooms, 5 full bathrooms and 1 half bath, with 3,875 square feet under air, a great room floor plan, soaring 22-foot vaulted ceilings, and walls of windows and doors—including large pocket sliders—that bring in abundant natural light and seamlessly connect indoor and outdoor living. The adjacent dining area provides ample space for entertaining, while the stunning kitchen—completely open to the great room—serves as the heart of the home with a large 9-foot island with extended seating, professional stainless steel gas appliances and a walk-in butler’s pantry. The home also features a fully integrated security system, whole-home sound system and a complete Control4 smart home system. The first-floor owner’s suite offers a private retreat with a walk-in shower, freestanding tub, dual vanities, and a large custom walk-in closet. A laundry room, powder room and mudroom complete the first level, and a 3-car garage provides ample parking and storage. Upstairs you’ll find four en-suite guest bedrooms, an additional laundry area to service them, and an expansive second-level balcony to take in the views. Outdoor living includes approximately 1,502 square feet of covered lanai, an exterior wrap-around porch, and balcony space designed for enjoying the island lifestyle, complete with SunBrite outdoor TVs, and Brazilian hardwood ceilings. The privately gated driveway and fully fenced property are surrounded by lush landscaping, creating a secluded tropical setting with a large swimming pool, champagne spa and expansive pool deck perfect for relaxing or entertaining. A private well supports irrigation. With 31 linear feet of canal frontage, the property features a 31-by-12-foot electric boat lift rated for 6,500 pounds, two jet ski ramps and about a 4.5-foot draft—ideal for boating and enjoying the water, making this oasis the perfect place to enjoy the Siesta Key lifestyle.

5 Beds ⋅ 6 Baths ⋅ A4698367 MLS

Start living your dream lifestyle on world-famous Siesta Key in this Pham Development custom-built waterfront British West Indies–style home. Located on a quiet street on the north end of the key—close to the beach, Siesta Key Village and Out-of-Door Academy—and just minutes on and off the island, this residence offers island living at its best. Set on a corner canal-front lot, the two-story home features 5 bedrooms, 5 full bathrooms and 1 half bath, with 3,875 square feet under air, a great room floor plan, soaring 22-foot vaulted ceilings, and walls of windows and doors—including large pocket sliders—that bring in abundant natural light and seamlessly connect indoor and outdoor living. The adjacent dining area provides ample space for entertaining, while the stunning kitchen—completely open to the great room—serves as the heart of the home with a large 9-foot island with extended seating, professional stainless steel gas appliances and a walk-in butler’s pantry. The home also features a fully integrated security system, whole-home sound system and a complete Control4 smart home system. The first-floor owner’s suite offers a private retreat with a walk-in shower, freestanding tub, dual vanities, and a large custom walk-in closet. A laundry room, powder room and mudroom complete the first level, and a 3-car garage provides ample parking and storage. Upstairs you’ll find four en-suite guest bedrooms, an additional laundry area to service them, and an expansive second-level balcony to take in the views. Outdoor living includes approximately 1,502 square feet of covered lanai, an exterior wrap-around porch, and balcony space designed for enjoying the island lifestyle, complete with SunBrite outdoor TVs, and Brazilian hardwood ceilings. The privately gated driveway and fully fenced property are surrounded by lush landscaping, creating a secluded tropical setting with a large swimming pool, champagne spa and expansive pool deck perfect for relaxing or entertaining. A private well supports irrigation. With 31 linear feet of canal frontage, the property features a 31-by-12-foot electric boat lift rated for 6,500 pounds, two jet ski ramps and about a 4.5-foot draft—ideal for boating and enjoying the water, making this oasis the perfect place to enjoy the Siesta Key lifestyle.

4634 Higel Avenue, Siesta Key

Listing courtesy of PHAM REALTY GROUP LLC. 559-359-5112

$569,000

A Wonderful, Beachside Opportunity Awaits in Vista Hermosa! Discover the ultimate turnkey coastal lifestyle with this newly renovated, beautifully furnished 2-bedroom, 2-bathroom villa condominium (furnishings included). Step inside to find stunning beach-oriented finishes, brand-new ceramic plank flooring, new appliances, and modern cabinets and countertops. Perfectly positioned within easy walking distance of both Crescent Beach and the world-famous Siesta Key Beach, this home lets you spend your days playing in the sand and surf and your evenings soaking in dramatic, world-class sunsets. After a long day in the sun, relax in the sparkling Vista Hermosa community pool. This villa offers premium convenience with an attached carport and a well-sized private laundry room that doubles as excellent storage for your beach chairs, toys, and fishing gear. Step outside for a brief walk to shopping and popular beach-themed restaurants, including the Daiquiri Deck and Captain Curt's. Want to explore further? Hop on the free Siesta Islander trolley for an easy ride up to Siesta Village to enjoy its endless souvenir shops and diverse breakfast, lunch, and dinner dining options. Whether you are seeking a permanent tropical retreat or a lucrative island getaway, this gorgeous villa offers the absolute best of Siesta Key living!

2 Beds ⋅ 2 Baths ⋅ A4698372 MLS

A Wonderful, Beachside Opportunity Awaits in Vista Hermosa! Discover the ultimate turnkey coastal lifestyle with this newly renovated, beautifully furnished 2-bedroom, 2-bathroom villa condominium (furnishings included). Step inside to find stunning beach-oriented finishes, brand-new ceramic plank flooring, new appliances, and modern cabinets and countertops. Perfectly positioned within easy walking distance of both Crescent Beach and the world-famous Siesta Key Beach, this home lets you spend your days playing in the sand and surf and your evenings soaking in dramatic, world-class sunsets. After a long day in the sun, relax in the sparkling Vista Hermosa community pool. This villa offers premium convenience with an attached carport and a well-sized private laundry room that doubles as excellent storage for your beach chairs, toys, and fishing gear. Step outside for a brief walk to shopping and popular beach-themed restaurants, including the Daiquiri Deck and Captain Curt's. Want to explore further? Hop on the free Siesta Islander trolley for an easy ride up to Siesta Village to enjoy its endless souvenir shops and diverse breakfast, lunch, and dinner dining options. Whether you are seeking a permanent tropical retreat or a lucrative island getaway, this gorgeous villa offers the absolute best of Siesta Key living!

161 Vista Hermosa Circle Unit 26A, Siesta Key

Listing courtesy of RKW BUTTON. 941-378-2328

$525,000

Welcome to the beautifully maintained and highly sought-after Gulf to Bay community on Siesta Key—Bay Tree Club. This charming 2-bedroom, 2-bath END UNIT is situated on the second floor, offering an abundance of natural light through its FOUR SIDE WINDOWS. Enjoy open views of the swimming pool and a glimpse of Little Sarasota Bay in the distance. Bay Tree Club boasts PRIVATE DEEDED BEACH ACCESS, a bayside swimming pool with a picnic and grill area, and a gulf-side swimming pool equipped with additional grills and picnic spaces. The community also features beautifully maintained BOAT DOCKS for your convenience, along with kayak and canoe storage onsite. Each unit includes a PRIVATE GULF SIDE CABANA for storing beach chairs and toys. The grounds are impeccably kept, and the community welcomes two pets, each weighing no more than 35 pounds. There is flexible rental availability, with a one-month minimum during peak season and a two-week minimum in the offseason. This FURNISHED unit is ready for its new owner!

2 Beds ⋅ 2 Baths ⋅ A4697723 MLS ⋅ B BLDG.

Welcome to the beautifully maintained and highly sought-after Gulf to Bay community on Siesta Key—Bay Tree Club. This charming 2-bedroom, 2-bath END UNIT is situated on the second floor, offering an abundance of natural light through its FOUR SIDE WINDOWS. Enjoy open views of the swimming pool and a glimpse of Little Sarasota Bay in the distance. Bay Tree Club boasts PRIVATE DEEDED BEACH ACCESS, a bayside swimming pool with a picnic and grill area, and a gulf-side swimming pool equipped with additional grills and picnic spaces. The community also features beautifully maintained BOAT DOCKS for your convenience, along with kayak and canoe storage onsite. Each unit includes a PRIVATE GULF SIDE CABANA for storing beach chairs and toys. The grounds are impeccably kept, and the community welcomes two pets, each weighing no more than 35 pounds. There is flexible rental availability, with a one-month minimum during peak season and a two-week minimum in the offseason. This FURNISHED unit is ready for its new owner!

8625 Midnight Pass Road Unit 208B, Siesta Key

Listing courtesy of WATERSIDE REALTY LLC. 941-346-7454

$699,000

Fantastic Siesta Key sunsets await from this spacious and updated two-bedroom, two-bath condominium facing west overlooking Siesta Key Beach. You can be on the sugary sands in seconds from your front door. Beautifully finished with an open floor plan, amazing natural light, neutral ceramic tile throughout, large kitchen island bar complete with granite countertops and beverage refrigerator, stainless steel appliances, spacious walk-in finished closets, custom built-ins, crown molding, plantation shutters, and all impact glass windows and sliders. This unit has a new air conditioning system, and the building has just been freshly painted. Beach Way allows monthly rentals 12 times a year, and has a large heated pool with an outside grilling area, social room with a kitchen for entertaining, elevator to your floor and a separate storage closet for all your beach needs. A carport just outside this condominium is included but there is no need for a car as you are minutes from the shopping and dining of Siesta Key Village, or a short ride to the arts and culture of downtown Sarasota. A great Island getaway, full-time residence or a highly desirable investment property as this condominium has a good rental history, allowing you to still enjoy the benefits of personal use when not renting. A truly unique property.

2 Beds ⋅ 2 Baths ⋅ A4697642 MLS ⋅ N/A BLDG.

Fantastic Siesta Key sunsets await from this spacious and updated two-bedroom, two-bath condominium facing west overlooking Siesta Key Beach. You can be on the sugary sands in seconds from your front door. Beautifully finished with an open floor plan, amazing natural light, neutral ceramic tile throughout, large kitchen island bar complete with granite countertops and beverage refrigerator, stainless steel appliances, spacious walk-in finished closets, custom built-ins, crown molding, plantation shutters, and all impact glass windows and sliders. This unit has a new air conditioning system, and the building has just been freshly painted. Beach Way allows monthly rentals 12 times a year, and has a large heated pool with an outside grilling area, social room with a kitchen for entertaining, elevator to your floor and a separate storage closet for all your beach needs. A carport just outside this condominium is included but there is no need for a car as you are minutes from the shopping and dining of Siesta Key Village, or a short ride to the arts and culture of downtown Sarasota. A great Island getaway, full-time residence or a highly desirable investment property as this condominium has a good rental history, allowing you to still enjoy the benefits of personal use when not renting. A truly unique property.

5600 Beach Way Dr Unit 213, Siesta Key

Listing courtesy of EXIT KING REALTY. 941-927-6060

$559,000

Ideally on the south end of Siesta Key, directly across from the free Siesta Key trolley and less than a quarter mile to Turtle Beach, this two-bedroom, two-bath residence offers 1,093 square feet of living space with panoramic Sarasota Bay views and glimpses of the Gulf. The open-concept great room is designed to maximize the water views and features luxury vinyl tile flooring, built-in surround sound and direct access to the screened lanai. Motorized blinds enhance the lanai, creating a comfortable space to enjoy the serene bayfront scenery. The kitchen is open to the living area and offers granite countertops, stainless steel appliances, creamy white cabinetry, a spacious pantry, and views of the Gulf and Sarasota Bay. Water views continue into the primary suite, where owners can wake to spectacular sunrises from the comfort of their bedroom. The primary suite also features a custom walk-in closet system and en-suite bath. The guest bedroom offers Gulf views and a large walk-in closet. Additional conveniences include a dedicated storage space, communal laundry facilities on the same floor adjacent to the elevator, an assigned covered carport space near the elevator and abundant guest parking. Recent improvements include a new electrical panel in 2021 and a new water heater in 2026. Sunrise Cove offers an array of amenities, including a renovated clubhouse with social spaces and kitchen, fitness center, library, billiards and table tennis, two heated swimming pools, tennis courts, pickleball courts, grilling areas and boat slips available for lease. Residents can also take advantage of the kayak, canoe and paddleboard storage available for lease, along with convenient marina access nearby. Enjoy easy access to Turtle Beach, boating, waterfront recreation and all the shopping, dining and entertainment of Siesta Village. Experience the best of Siesta Key living with bayfront views, beach access and resort-style amenities in one exceptional location.

2 Beds ⋅ 2 Baths ⋅ N6144720 MLS ⋅ 8911 BLDG.

Ideally on the south end of Siesta Key, directly across from the free Siesta Key trolley and less than a quarter mile to Turtle Beach, this two-bedroom, two-bath residence offers 1,093 square feet of living space with panoramic Sarasota Bay views and glimpses of the Gulf. The open-concept great room is designed to maximize the water views and features luxury vinyl tile flooring, built-in surround sound and direct access to the screened lanai. Motorized blinds enhance the lanai, creating a comfortable space to enjoy the serene bayfront scenery. The kitchen is open to the living area and offers granite countertops, stainless steel appliances, creamy white cabinetry, a spacious pantry, and views of the Gulf and Sarasota Bay. Water views continue into the primary suite, where owners can wake to spectacular sunrises from the comfort of their bedroom. The primary suite also features a custom walk-in closet system and en-suite bath. The guest bedroom offers Gulf views and a large walk-in closet. Additional conveniences include a dedicated storage space, communal laundry facilities on the same floor adjacent to the elevator, an assigned covered carport space near the elevator and abundant guest parking. Recent improvements include a new electrical panel in 2021 and a new water heater in 2026. Sunrise Cove offers an array of amenities, including a renovated clubhouse with social spaces and kitchen, fitness center, library, billiards and table tennis, two heated swimming pools, tennis courts, pickleball courts, grilling areas and boat slips available for lease. Residents can also take advantage of the kayak, canoe and paddleboard storage available for lease, along with convenient marina access nearby. Enjoy easy access to Turtle Beach, boating, waterfront recreation and all the shopping, dining and entertainment of Siesta Village. Experience the best of Siesta Key living with bayfront views, beach access and resort-style amenities in one exceptional location.

8911 Midnight Pass Road Unit 409, Siesta Key

Listing courtesy of PREMIER SOTHEBYS INTL REALTY. 941-412-3323

$1,195,000

Gulf view condominium at the Siesta Sands Resort, at the southern tip of world-famous Crescent Beach on Siesta Key. This second-floor end unit, featuring two bedrooms, two baths and two private balconies, has been completely renovated, tastefully decorated and furnished, with in-unit laundry, a reserved parking space and a nice view of the blue waters of the Gulf, as well as a good view of one of the resort’s pools. The resort-style condominium is on a beautiful private beach featuring what has been rated as the whitest sand, consisting of 99 percent pure quartz, which stays cool under your feet. Residents of Siesta Sands enjoy an impressive array of resort-style amenities, including beach service for lounge chairs and umbrellas, two heated pools, community Wi-Fi, a poolside gazebo, gas grills, an exercise room and serene bamboo lounge. This boutique beachfront community offers a secluded, gated retreat with only 31 units and exclusive private beach access to Crescent Beach. The unbeatable location places you near Siesta Key's South Village. Siesta Sands allows weekly rentals and has an excellent on-site rental office to keep the condominium rented when not being utilized for personal use. The Point of Rocks is an area known for its coral formations and marine life, ideal for fishing or snorkeling. This resort condominium is offered turnkey furnished with solid rental history and further bookings in place. This is must-see. Don’t miss out.

2 Beds ⋅ 2 Baths ⋅ A4697514 MLS ⋅ Siesta Sands BLDG.

Gulf view condominium at the Siesta Sands Resort, at the southern tip of world-famous Crescent Beach on Siesta Key. This second-floor end unit, featuring two bedrooms, two baths and two private balconies, has been completely renovated, tastefully decorated and furnished, with in-unit laundry, a reserved parking space and a nice view of the blue waters of the Gulf, as well as a good view of one of the resort’s pools. The resort-style condominium is on a beautiful private beach featuring what has been rated as the whitest sand, consisting of 99 percent pure quartz, which stays cool under your feet. Residents of Siesta Sands enjoy an impressive array of resort-style amenities, including beach service for lounge chairs and umbrellas, two heated pools, community Wi-Fi, a poolside gazebo, gas grills, an exercise room and serene bamboo lounge. This boutique beachfront community offers a secluded, gated retreat with only 31 units and exclusive private beach access to Crescent Beach. The unbeatable location places you near Siesta Key's South Village. Siesta Sands allows weekly rentals and has an excellent on-site rental office to keep the condominium rented when not being utilized for personal use. The Point of Rocks is an area known for its coral formations and marine life, ideal for fishing or snorkeling. This resort condominium is offered turnkey furnished with solid rental history and further bookings in place. This is must-see. Don’t miss out.

1001 Point Of Rocks Road Unit 208, Siesta Key

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY. 941-364-4000

$649,000

Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. This completely updated, open floor plan. Upgrades galore!! Fantastic rental history! The HOA installed a new roof on the property in 2023, too! Jamaica Royale allows short term rentals so this could be a great investment property or keep it for your own second home. This is the closest gulf side weekly rental property to the main public beach offering 3 swimming pools, grilling stations and shuffle board. Make this great property yours today at a value!

1 Beds ⋅ 1 Baths ⋅ A4697756 MLS ⋅ 3 BLDG.

Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. This completely updated, open floor plan. Upgrades galore!! Fantastic rental history! The HOA installed a new roof on the property in 2023, too! Jamaica Royale allows short term rentals so this could be a great investment property or keep it for your own second home. This is the closest gulf side weekly rental property to the main public beach offering 3 swimming pools, grilling stations and shuffle board. Make this great property yours today at a value!

5830 Midnight Pass Road Unit 3, Siesta Key

Listing courtesy of TIDELINE REAL ESTATE BROKERS. 941-587-1669

$15,900,000

Inspired by the timeless grandeur of Louisiana's legendary Oak Alley Plantation, this extraordinary Gulf-to-lagoon estate is one of the most architecturally distinctive residences on Siesta Key. Positioned on a rare 1.97-acre Gulf-to-bay homesite within the private gates of The Sanderling Club, this home evokes the sophistication of a Southern manor while embracing the relaxed sophistication of Florida's Gulf Coast. A sweeping palm-lined drive, stately columned façade, and symmetrical architecture create a memorable first impression, echoing the enduring beauty that inspired its design. Constructed by Christner Bros., the residence encompasses approximately 8,209 square feet under air with four bedrooms, four full baths, one half bath, elevator access, and an oversized five-car collector's garage with dedicated workshop space. Designed for both grand-scale entertaining and refined everyday living, the home showcases soaring ceilings, handcrafted millwork, marble flooring, and a dramatic curved staircase that anchors the elegant interiors. Expansive living and dining rooms flow effortlessly onto an exceptional wraparound covered terrace, creating seamless indoor-outdoor living while framing panoramic views of the Gulf of Mexico, Heron Lagoon, and the surrounding tropical landscape. The chef's kitchen is equally suited for intimate gatherings and large-scale entertaining, featuring custom cabinetry, granite countertops, Wolf and Sub-Zero appliances, double wall ovens, generous preparation areas, and direct terrace access. A richly detailed executive office with custom built-ins, an extensive butler's pantry, media room, and abundant utility spaces further enhance the home's thoughtful design. The primary suite is a private sanctuary with terrace access, generous sitting areas, and a spa-inspired bath featuring dual vanities, extensive custom cabinetry, a walk-in shower, and abundant natural light. Three additional guest suites, each with en-suite baths, provide luxurious accommodations while overlooking the estate's lush tropical grounds. The lower level offers exceptional flexibility with expansive bonus space ideal for a wellness center, fitness studio, golf simulator, game room, collector's gallery, workshop, or additional recreational living. Impact-rated windows and doors, hurricane shutters and screens, a security system, and a newer 24-kW Kohler generator contribute to the home's enduring quality and peace of mind. The estate's setting is equally remarkable. With approximately 150 feet of pristine Gulf frontage and 150 feet of frontage along tranquil Heron Lagoon, opportunities to own a true Gulf-to-lagoon property are exceedingly rare. Launch a kayak or paddleboard from the private dock, spend afternoons on the secluded beach, or experience spectacular sunsets over the Gulf from your own backyard. Residents also enjoy the exclusive amenities of The Sanderling Club, including a private beach, marina, tennis courts, clubhouse, and one of Siesta Key's most private and prestigious waterfront communities. Just beyond the gates await Siesta Key's internationally acclaimed quartz-sand beaches, the boutiques and restaurants of Siesta Village, and the arts, dining, and cultural attractions of downtown Sarasota. 8132 Sanderling Road is a legacy estate where inspired architecture, timeless elegance, and one of Florida's rarest Gulf-to-lagoon settings come together to create an offering of exceptional significance.

4 Beds ⋅ 5 Baths ⋅ A4694017 MLS

Inspired by the timeless grandeur of Louisiana's legendary Oak Alley Plantation, this extraordinary Gulf-to-lagoon estate is one of the most architecturally distinctive residences on Siesta Key. Positioned on a rare 1.97-acre Gulf-to-bay homesite within the private gates of The Sanderling Club, this home evokes the sophistication of a Southern manor while embracing the relaxed sophistication of Florida's Gulf Coast. A sweeping palm-lined drive, stately columned façade, and symmetrical architecture create a memorable first impression, echoing the enduring beauty that inspired its design. Constructed by Christner Bros., the residence encompasses approximately 8,209 square feet under air with four bedrooms, four full baths, one half bath, elevator access, and an oversized five-car collector's garage with dedicated workshop space. Designed for both grand-scale entertaining and refined everyday living, the home showcases soaring ceilings, handcrafted millwork, marble flooring, and a dramatic curved staircase that anchors the elegant interiors. Expansive living and dining rooms flow effortlessly onto an exceptional wraparound covered terrace, creating seamless indoor-outdoor living while framing panoramic views of the Gulf of Mexico, Heron Lagoon, and the surrounding tropical landscape. The chef's kitchen is equally suited for intimate gatherings and large-scale entertaining, featuring custom cabinetry, granite countertops, Wolf and Sub-Zero appliances, double wall ovens, generous preparation areas, and direct terrace access. A richly detailed executive office with custom built-ins, an extensive butler's pantry, media room, and abundant utility spaces further enhance the home's thoughtful design. The primary suite is a private sanctuary with terrace access, generous sitting areas, and a spa-inspired bath featuring dual vanities, extensive custom cabinetry, a walk-in shower, and abundant natural light. Three additional guest suites, each with en-suite baths, provide luxurious accommodations while overlooking the estate's lush tropical grounds. The lower level offers exceptional flexibility with expansive bonus space ideal for a wellness center, fitness studio, golf simulator, game room, collector's gallery, workshop, or additional recreational living. Impact-rated windows and doors, hurricane shutters and screens, a security system, and a newer 24-kW Kohler generator contribute to the home's enduring quality and peace of mind. The estate's setting is equally remarkable. With approximately 150 feet of pristine Gulf frontage and 150 feet of frontage along tranquil Heron Lagoon, opportunities to own a true Gulf-to-lagoon property are exceedingly rare. Launch a kayak or paddleboard from the private dock, spend afternoons on the secluded beach, or experience spectacular sunsets over the Gulf from your own backyard. Residents also enjoy the exclusive amenities of The Sanderling Club, including a private beach, marina, tennis courts, clubhouse, and one of Siesta Key's most private and prestigious waterfront communities. Just beyond the gates await Siesta Key's internationally acclaimed quartz-sand beaches, the boutiques and restaurants of Siesta Village, and the arts, dining, and cultural attractions of downtown Sarasota. 8132 Sanderling Road is a legacy estate where inspired architecture, timeless elegance, and one of Florida's rarest Gulf-to-lagoon settings come together to create an offering of exceptional significance.

8132 Sanderling Road, Siesta Key

Listing courtesy of DOUGLAS ELLIMAN. 941-867-6199

$364,000

At the very end of Midnight Pass Road—where tranquility, water, and lifestyle take over. The Pointe is a private, gated, park-like condominium community situated on the southernmost tip of Siesta Key, where Midnight Pass Road ends and a remarkable waterfront lifestyle begins. Surrounded by water, wildlife, and natural beauty, residents regularly enjoy sightings of dolphins, manatees, pelicans, herons, egrets, and active osprey nests, while kayakers and paddle boarders quietly pass through the surrounding waterways. Set on more than five acres and surrounded by over 900 feet of seawall, The Pointe combines a private gated setting, Gazebo Island, boat slips, kayak launches, abundant wildlife, and immediate access to Sarasota Bay and the Gulf—an exceptionally rare combination of amenities and natural beauty found in very few condominium communities in Southwest Florida. Unit 903S is one of only 16 one-bedroom residences within the entire community and is currently the only available one-bedroom opportunity at The Pointe. Positioned on the 9th floor, the residence enjoys wonderful sunrise views over Little Sarasota Bay and evening sunsets toward the Gulf. During much of the year, fresh Gulf breezes flow naturally through the residence, creating the relaxed coastal lifestyle that attracts owners to Siesta Key. The residence has been thoughtfully refreshed and furnished in a clean coastal-contemporary style with designer furnishings selected through The Pamaro Shop. The presentation emphasizes light, openness, comfort, and surrounding water views while still allowing future owners the flexibility to personalize the residence according to their own tastes. The Pointe is recognized for its strong ownership structure, professional on-site management, and completion of all required post-Champlain engineering and structural requirements. Major building improvements have been completed and paid for, providing buyers with confidence in the community's long-term stewardship and financial stability. WATERFRONT LIFESTYLE & AMENITIES • Largest condominium swimming pool on Siesta Key (heated year-round)• 12-person in-ground spa• Tennis and pickleball court• Three BBQ and outdoor gathering areas, including the covered island gazebo• Boat slips available for owners• Kayak and paddle board storage racks and launch areas• Less than five minutes by boat or kayak to the Gulf via Midnight Pass• Private Gazebo Island with BBQ facilities and park benches overlooking mangrove preserves and Sarasota Bay• Multiple garden sitting areas and park benches throughout the property• Seawall features a lighted concrete waterfront walkway, ideal for morning walks, sunset strolls, fishing, wildlife viewing, and enjoying the ever-changing beauty of Sarasota Bay• The Cottage Community Center with fireplace, full kitchen, social gathering areas, and community events• On-site Property Manager, Maintenance Manager, Maintenance Technician, and fully equipped maintenance workshop. The Pointe maintains a three-month minimum rental policy, preserving a quiet, owner-oriented environment without constant short-term rental turnover. Whether enjoying morning coffee overlooking the Bay, a sunset over the Gulf, boating through Midnight Pass, or simply relaxing in one of Siesta Key's most peaceful waterfront communities, Unit 903S offers a rare opportunity to enjoy the very best of coastal Florida living.

1 Beds ⋅ 1 Baths ⋅ A4696940 MLS ⋅ 9397 BLDG.

At the very end of Midnight Pass Road—where tranquility, water, and lifestyle take over. The Pointe is a private, gated, park-like condominium community situated on the southernmost tip of Siesta Key, where Midnight Pass Road ends and a remarkable waterfront lifestyle begins. Surrounded by water, wildlife, and natural beauty, residents regularly enjoy sightings of dolphins, manatees, pelicans, herons, egrets, and active osprey nests, while kayakers and paddle boarders quietly pass through the surrounding waterways. Set on more than five acres and surrounded by over 900 feet of seawall, The Pointe combines a private gated setting, Gazebo Island, boat slips, kayak launches, abundant wildlife, and immediate access to Sarasota Bay and the Gulf—an exceptionally rare combination of amenities and natural beauty found in very few condominium communities in Southwest Florida. Unit 903S is one of only 16 one-bedroom residences within the entire community and is currently the only available one-bedroom opportunity at The Pointe. Positioned on the 9th floor, the residence enjoys wonderful sunrise views over Little Sarasota Bay and evening sunsets toward the Gulf. During much of the year, fresh Gulf breezes flow naturally through the residence, creating the relaxed coastal lifestyle that attracts owners to Siesta Key. The residence has been thoughtfully refreshed and furnished in a clean coastal-contemporary style with designer furnishings selected through The Pamaro Shop. The presentation emphasizes light, openness, comfort, and surrounding water views while still allowing future owners the flexibility to personalize the residence according to their own tastes. The Pointe is recognized for its strong ownership structure, professional on-site management, and completion of all required post-Champlain engineering and structural requirements. Major building improvements have been completed and paid for, providing buyers with confidence in the community's long-term stewardship and financial stability. WATERFRONT LIFESTYLE & AMENITIES • Largest condominium swimming pool on Siesta Key (heated year-round)• 12-person in-ground spa• Tennis and pickleball court• Three BBQ and outdoor gathering areas, including the covered island gazebo• Boat slips available for owners• Kayak and paddle board storage racks and launch areas• Less than five minutes by boat or kayak to the Gulf via Midnight Pass• Private Gazebo Island with BBQ facilities and park benches overlooking mangrove preserves and Sarasota Bay• Multiple garden sitting areas and park benches throughout the property• Seawall features a lighted concrete waterfront walkway, ideal for morning walks, sunset strolls, fishing, wildlife viewing, and enjoying the ever-changing beauty of Sarasota Bay• The Cottage Community Center with fireplace, full kitchen, social gathering areas, and community events• On-site Property Manager, Maintenance Manager, Maintenance Technician, and fully equipped maintenance workshop. The Pointe maintains a three-month minimum rental policy, preserving a quiet, owner-oriented environment without constant short-term rental turnover. Whether enjoying morning coffee overlooking the Bay, a sunset over the Gulf, boating through Midnight Pass, or simply relaxing in one of Siesta Key's most peaceful waterfront communities, Unit 903S offers a rare opportunity to enjoy the very best of coastal Florida living.

9397 Midnight Pass Road Unit 903, Siesta Key

Listing courtesy of COLDWELL BANKER SARASOTA CENT.. 941-487-5600

$1,050,000

Welcome home to a fully updated, fully furnished 2 bedroom 2 bathroom beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring costal decor with modern neutral colors.This unit is nestled in B Building with direct beach access which is just steps away from your front door. Enjoy breath taking sunsets from your personal balcony or head down to the private beach for an up close view of the #1 beach in the US. The sandy white powder stretches 800 feet across this pristine 32 acre meticulously cared for tropical community. You will be impressed with world class amenities offered at Gulf & Bay Club. Enjoy the comfort of 24 hour gated security, heated pools, a fitness center, dry saunas, hot tub, tennis courts, just to name a few. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The amenities don’t stop there, the club house has a library, bar, pool table and TV's all for your enjoyment. Not to mention the electric car charging stations and car wash on grounds. You are moments away from Siesta Village to enjoy alfresco dining with live music, specialty shopping and more! Take a short trip to the mainland and discover theater, art and fine dining. This is the island resort lifestyle you have been looking for, don't let your chance of fine beach living slip away.

2 Beds ⋅ 2 Baths ⋅ A4697559 MLS ⋅ B407 BLDG.

Welcome home to a fully updated, fully furnished 2 bedroom 2 bathroom beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring costal decor with modern neutral colors.This unit is nestled in B Building with direct beach access which is just steps away from your front door. Enjoy breath taking sunsets from your personal balcony or head down to the private beach for an up close view of the #1 beach in the US. The sandy white powder stretches 800 feet across this pristine 32 acre meticulously cared for tropical community. You will be impressed with world class amenities offered at Gulf & Bay Club. Enjoy the comfort of 24 hour gated security, heated pools, a fitness center, dry saunas, hot tub, tennis courts, just to name a few. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The amenities don’t stop there, the club house has a library, bar, pool table and TV's all for your enjoyment. Not to mention the electric car charging stations and car wash on grounds. You are moments away from Siesta Village to enjoy alfresco dining with live music, specialty shopping and more! Take a short trip to the mainland and discover theater, art and fine dining. This is the island resort lifestyle you have been looking for, don't let your chance of fine beach living slip away.

5780 Midnight Pass Road Unit 407, Siesta Key

Listing courtesy of PREFERRED SHORE LLC. 941-999-1179

$650,137

Experience the ultimate island lifestyle in this beautifully appointed 2-bedroom, 2-bathroom condo on world-famous Siesta Key. Located just steps away from the powdery white quartz sands of Siesta Beach, this property grants you your own private deeded beach access where loungers are waiting for you. With the vibrant dining and shopping of the Village, this location cannot be beat. You can be picked up right at the front of the building with free transportation on the island. The split bedroom living space area features Italian porcelain tile flooring, crown molding, abundant natural light, hurricane impact windows throughout, NO popcorn ceilings here-smooth as butter, seamlessly flowing onto a private lanai where you can enjoy your morning coffee with a peaceful view of the courtyard, pool, pond, a peak of the Bay, and beautiful grounds. The community offers resort-style amenities, including two heated pools and hot tubs (one on the Bay side and one on the Gulf side), tennis courts, pickleball courts, a fitness center, shuffle board, fishing dock, grilling stations, library and a community room. You will have an assigned covered parking space under the building, ample additional parking for your guests and a storage unit for your beach toys. Excelsior Beach to Bay also has a management company on site to rent your unit while you are away for your convenience, if you choose to do so. You will love this close knit community and all the fun social events offered throughout the season. Call for your private showing today.

2 Beds ⋅ 2 Baths ⋅ A4696685 MLS ⋅ 6267 BLDG.

Experience the ultimate island lifestyle in this beautifully appointed 2-bedroom, 2-bathroom condo on world-famous Siesta Key. Located just steps away from the powdery white quartz sands of Siesta Beach, this property grants you your own private deeded beach access where loungers are waiting for you. With the vibrant dining and shopping of the Village, this location cannot be beat. You can be picked up right at the front of the building with free transportation on the island. The split bedroom living space area features Italian porcelain tile flooring, crown molding, abundant natural light, hurricane impact windows throughout, NO popcorn ceilings here-smooth as butter, seamlessly flowing onto a private lanai where you can enjoy your morning coffee with a peaceful view of the courtyard, pool, pond, a peak of the Bay, and beautiful grounds. The community offers resort-style amenities, including two heated pools and hot tubs (one on the Bay side and one on the Gulf side), tennis courts, pickleball courts, a fitness center, shuffle board, fishing dock, grilling stations, library and a community room. You will have an assigned covered parking space under the building, ample additional parking for your guests and a storage unit for your beach toys. Excelsior Beach to Bay also has a management company on site to rent your unit while you are away for your convenience, if you choose to do so. You will love this close knit community and all the fun social events offered throughout the season. Call for your private showing today.

6267 Midnight Pass Road Unit 306, Siesta Key

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICE. 941-556-2150

$1,250,000

Nestled beneath majestic oak trees, this beautifully updated home has a flexible floor plan. It boasts multiple sleeping areas that comfortably accommodates visiting family and guests. Tastefully furnished and decorated, this residence underwent extensive renovations in recent years and features a newly installed roof, new impact rated windows, restored terrazzo flooring complemented by updated tile throughout. The kitchen is well-appointed with stainless steel appliances. Both bathrooms have been tastefully remodeled with granite countertops, updated fixtures, modern sinks, and designer finishes. Walk, Bike or golf cart just a short distance to the Siesta Key Village and America's most celebrated beach. Step outside to enjoy the enclosed, heated, chlorine-free pool and a private backyard oasis, perfect for relaxing or entertaining. Nearby, Siesta Key Village offers boutique shopping, acclaimed dining, live entertainment, vibrant nightlife, charming cafés, and peaceful parks. Aside from the stunning Siesta Key beaches... pickle ball, tennis courts and parks just a short bike ride away, provide fantastic outdoor recreation opportunities. Throughout the year, the island hosts a variety of special events that celebrate the unique lifestyle and beauty of the area. Discover the best of island living on world-famous Siesta Key, celebrated for its powder-soft white sand, crystal-clear turquoise waters, and relaxed coastal lifestyle. Whether you're looking for a full-time residence, vacation retreat, or income-producing investment, this charming property offers the opportunity to own your own piece of paradise. A pre-sale home inspection has been completed, providing added peace of mind, and the property is being offered turn-key and ready to enjoy. The seller is also offering a one-year home warranty with the sale. With strong year-round rental demand, this property combines an exceptional island lifestyle with attractive investment potential. All measurements are approximate and should be independently verified by the buyer.

2 Beds ⋅ 2 Baths ⋅ A4697056 MLS

Nestled beneath majestic oak trees, this beautifully updated home has a flexible floor plan. It boasts multiple sleeping areas that comfortably accommodates visiting family and guests. Tastefully furnished and decorated, this residence underwent extensive renovations in recent years and features a newly installed roof, new impact rated windows, restored terrazzo flooring complemented by updated tile throughout. The kitchen is well-appointed with stainless steel appliances. Both bathrooms have been tastefully remodeled with granite countertops, updated fixtures, modern sinks, and designer finishes. Walk, Bike or golf cart just a short distance to the Siesta Key Village and America's most celebrated beach. Step outside to enjoy the enclosed, heated, chlorine-free pool and a private backyard oasis, perfect for relaxing or entertaining. Nearby, Siesta Key Village offers boutique shopping, acclaimed dining, live entertainment, vibrant nightlife, charming cafés, and peaceful parks. Aside from the stunning Siesta Key beaches... pickle ball, tennis courts and parks just a short bike ride away, provide fantastic outdoor recreation opportunities. Throughout the year, the island hosts a variety of special events that celebrate the unique lifestyle and beauty of the area. Discover the best of island living on world-famous Siesta Key, celebrated for its powder-soft white sand, crystal-clear turquoise waters, and relaxed coastal lifestyle. Whether you're looking for a full-time residence, vacation retreat, or income-producing investment, this charming property offers the opportunity to own your own piece of paradise. A pre-sale home inspection has been completed, providing added peace of mind, and the property is being offered turn-key and ready to enjoy. The seller is also offering a one-year home warranty with the sale. With strong year-round rental demand, this property combines an exceptional island lifestyle with attractive investment potential. All measurements are approximate and should be independently verified by the buyer.

5128 Oxford Drive, Siesta Key

Listing courtesy of COLDWELL BANKER REALTY. 941-349-4411

$595,000

NEW PRICE — SIESTA KEY BEACHFRONT LIFESTYLE AWAITS! Don’t miss this opportunity to own a beautifully renovated TURNKEY FURNISHED 2-bedroom, 1-bath villa in Casa Blanca, one of Siesta Key’s most desirable beachfront communities. Located on the Gulf side of Midnight Pass Road, you’re just steps from the powdery white quartz sands and turquoise waters of Crescent Beach. Near Point of Rocks, enjoy incredible beach walks, shelling, snorkeling, swimming, and unforgettable Gulf sunsets right outside your door. Beautifully remodeled from top to bottom, this move-in-ready villa has been thoughtfully updated for easy, carefree island living. Features include impact-rated windows and doors, an updated kitchen with GE appliances, a beautifully renovated bathroom, tile flooring throughout, and a bright, open floor plan with stylish coastal finishes. The location within Casa Blanca is another standout feature—just a short stroll to the community pool and clubhouse and, of course, the BEACH! Looking for a Siesta Key property you can enjoy while also having rental potential? Casa Blanca’s highly desirable 5- to 7-day minimum rental policy provides tremendous flexibility, making this an appealing option as a vacation getaway, investment property, seasonal retreat, or full-time island home. Leave the car behind and embrace the Siesta Key lifestyle! The nearby Siesta Key trolley provides easy access to Siesta Key Village, Stickney Point, restaurants, shopping, entertainment, and waterfront dining. Turnkey furnished, beautifully renovated, impact windows and doors, flexible rentals, a great location near the pool, and just steps from one of the most beautiful beaches in the world—this is the Siesta Key opportunity you’ve been waiting for. NEW PRICE—schedule your private showing and come experience your own little piece of paradise!

2 Beds ⋅ 1 Baths ⋅ A4696503 MLS

NEW PRICE — SIESTA KEY BEACHFRONT LIFESTYLE AWAITS! Don’t miss this opportunity to own a beautifully renovated TURNKEY FURNISHED 2-bedroom, 1-bath villa in Casa Blanca, one of Siesta Key’s most desirable beachfront communities. Located on the Gulf side of Midnight Pass Road, you’re just steps from the powdery white quartz sands and turquoise waters of Crescent Beach. Near Point of Rocks, enjoy incredible beach walks, shelling, snorkeling, swimming, and unforgettable Gulf sunsets right outside your door. Beautifully remodeled from top to bottom, this move-in-ready villa has been thoughtfully updated for easy, carefree island living. Features include impact-rated windows and doors, an updated kitchen with GE appliances, a beautifully renovated bathroom, tile flooring throughout, and a bright, open floor plan with stylish coastal finishes. The location within Casa Blanca is another standout feature—just a short stroll to the community pool and clubhouse and, of course, the BEACH! Looking for a Siesta Key property you can enjoy while also having rental potential? Casa Blanca’s highly desirable 5- to 7-day minimum rental policy provides tremendous flexibility, making this an appealing option as a vacation getaway, investment property, seasonal retreat, or full-time island home. Leave the car behind and embrace the Siesta Key lifestyle! The nearby Siesta Key trolley provides easy access to Siesta Key Village, Stickney Point, restaurants, shopping, entertainment, and waterfront dining. Turnkey furnished, beautifully renovated, impact windows and doors, flexible rentals, a great location near the pool, and just steps from one of the most beautiful beaches in the world—this is the Siesta Key opportunity you’ve been waiting for. NEW PRICE—schedule your private showing and come experience your own little piece of paradise!

6154 Midnight Pass Road Unit B1, Siesta Key

Listing courtesy of COLDWELL BANKER REALTY. 941-349-4411

$2,895,000

There Is Only One. Crescent Beach House was purpose-built for a different kind of ownership experience. One where beach days, family gatherings, and investment performance can coexist under the same roof. Positioned in one of Siesta Key's most enduring vacation corridors, this is the type of property people return to year after year, and increasingly, seek to own. Sited at the mouth of the Point of Rocks’ beach access located at the end of the street, Crescent Beach House is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, and expansive indoor-outdoor living spaces designed to accommodate large groups with ease. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment performance. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.

5 Beds ⋅ 7 Baths ⋅ A4694972 MLS

There Is Only One. Crescent Beach House was purpose-built for a different kind of ownership experience. One where beach days, family gatherings, and investment performance can coexist under the same roof. Positioned in one of Siesta Key's most enduring vacation corridors, this is the type of property people return to year after year, and increasingly, seek to own. Sited at the mouth of the Point of Rocks’ beach access located at the end of the street, Crescent Beach House is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, and expansive indoor-outdoor living spaces designed to accommodate large groups with ease. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment performance. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.

Siesta Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-349-3444

$689,000

**Resort Style Living in the Heart of Siesta Key, For Those Who Desire The Active Life Style** Experience the best of Siesta Key living at Harbor Towers Yacht & Racquet Club, a premier waterfront community overlooking Little Sarasota Bay with one of the lowest HOA's on the Key. This beautifully maintained turn-key furnished **2-bedroom, 2-bath residence** features a desirable **split floor plan** and is ideally positioned on the **5th floor**, offering tranquil **Intracoastal Waterway views**. Inside, you’ll find thoughtful updates including **new wood-look vinyl plank flooring in both bedrooms**, along with a **new electric range and microwave** in the kitchen. Enjoy the convenience of a **deeded covered carport**, providing protected parking and added value. Harbor Towers is renowned for its resort-style amenities, including **two heated pools**, a clubhouse with outdoor grilling patio, and a **state-of-the-art fitness center** with cardio equipment, free weights, and sauna. Tennis enthusiasts will appreciate the meticulously maintained **Har-Tru courts**, serviced daily for optimal play. The in house Rental Agency is there to help you rent, with a 2 week minimum rental policy. For boating and water lovers, the on-site **marina with 40 slips equipped with water/electric available on first-come, first-served basis**, along with kayak storage and launch, offers direct access to the Intracoastal Waterway. Residents can relax along the scenic waterway, enjoy shaded seating, or unwind in the waterfront gazebo. Additional perks include bicycle storage and **complimentary access to the Siesta Key Open-Air Trolley**, making it easy to explore the island. You’re just moments from **world-famous Siesta Key Beach**, known for its powdery quartz sand and breathtaking sunsets, as well as Siesta Key Village with its vibrant dining, shopping, and entertainment. The community has recently undergone significant upgrades, including **new stucco exterior, impact-resistant windows, and sliding glass doors**, offering enhanced beauty and peace of mind.

2 Beds ⋅ 2 Baths ⋅ A4696548 MLS ⋅ 5855 BLDG.

**Resort Style Living in the Heart of Siesta Key, For Those Who Desire The Active Life Style** Experience the best of Siesta Key living at Harbor Towers Yacht & Racquet Club, a premier waterfront community overlooking Little Sarasota Bay with one of the lowest HOA's on the Key. This beautifully maintained turn-key furnished **2-bedroom, 2-bath residence** features a desirable **split floor plan** and is ideally positioned on the **5th floor**, offering tranquil **Intracoastal Waterway views**. Inside, you’ll find thoughtful updates including **new wood-look vinyl plank flooring in both bedrooms**, along with a **new electric range and microwave** in the kitchen. Enjoy the convenience of a **deeded covered carport**, providing protected parking and added value. Harbor Towers is renowned for its resort-style amenities, including **two heated pools**, a clubhouse with outdoor grilling patio, and a **state-of-the-art fitness center** with cardio equipment, free weights, and sauna. Tennis enthusiasts will appreciate the meticulously maintained **Har-Tru courts**, serviced daily for optimal play. The in house Rental Agency is there to help you rent, with a 2 week minimum rental policy. For boating and water lovers, the on-site **marina with 40 slips equipped with water/electric available on first-come, first-served basis**, along with kayak storage and launch, offers direct access to the Intracoastal Waterway. Residents can relax along the scenic waterway, enjoy shaded seating, or unwind in the waterfront gazebo. Additional perks include bicycle storage and **complimentary access to the Siesta Key Open-Air Trolley**, making it easy to explore the island. You’re just moments from **world-famous Siesta Key Beach**, known for its powdery quartz sand and breathtaking sunsets, as well as Siesta Key Village with its vibrant dining, shopping, and entertainment. The community has recently undergone significant upgrades, including **new stucco exterior, impact-resistant windows, and sliding glass doors**, offering enhanced beauty and peace of mind.

5855 Midnight Pass Road Unit 510, Siesta Key

Listing courtesy of COLDWELL BANKER REALTY. 941-349-4411

$2,895,000

There Is Only One. Point of Rocks. Crescent Beach. Captain Curt's. For generations, this stretch of Siesta Key has attracted families, vacationers, and investors alike, and that demand has endured year after year for what seems to be one simple reason: people never seem to stop coming back. Positioned just moments from beach access located at the end of the street, Point of Rocks is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, waterslide, and expansive indoor-outdoor living spaces designed to accommodate up to fourteen guests. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment potential. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.

5 Beds ⋅ 7 Baths ⋅ A4694978 MLS ⋅ 6910 B BLDG.

There Is Only One. Point of Rocks. Crescent Beach. Captain Curt's. For generations, this stretch of Siesta Key has attracted families, vacationers, and investors alike, and that demand has endured year after year for what seems to be one simple reason: people never seem to stop coming back. Positioned just moments from beach access located at the end of the street, Point of Rocks is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, waterslide, and expansive indoor-outdoor living spaces designed to accommodate up to fourteen guests. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment potential. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.

6910 Midnight Pass Road Unit B, Siesta Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-349-3444

$595,000

Fully Funded Reserves & Passed SIRS Inspections! 2 Bedroom, 2 Bath First-Floor Condo with Screened Lanai on fabulous Siesta Key Across from Crescent Beach – Just Steps from Siesta Key Beach! This turnkey furnished, beautifully maintained 2-bedroom, 2-bathroom condo is located on the first floor and offers the perfect blend of comfort and convenience. Enjoy stunning views of the Intracoastal Waterway right from your screened lanai. The property is fully funded for reserves and has passed the required SIRS inspections, providing peace of mind for the new owner. Key Features: Turnkey Furnished: Move-in ready with everything you need. Location: Prime location on Siesta Key, just across the street from Crescent Beach and an easy walk to world-renowned Siesta Key Beach. Views: Enjoy picturesque views of the Intracoastal Waterway from your lanai. Community Amenities: Marina with dock space available for rent or purchase. Fitness center and basketball court for active living. Heated pool for year-round enjoyment. Rental Opportunities: Midnight Cove II allows 1-week rentals, offering great potential for short-term rental income. The on-site office is optionally available to handle rentals on your behalf, making it a hassle-free investment. This property is an excellent opportunity for investors or those seeking a relaxing retreat in one of Florida’s most desirable locations. Schedule your private showing today!

2 Beds ⋅ 2 Baths ⋅ A4695562 MLS ⋅ 2 BLDG.

Fully Funded Reserves & Passed SIRS Inspections! 2 Bedroom, 2 Bath First-Floor Condo with Screened Lanai on fabulous Siesta Key Across from Crescent Beach – Just Steps from Siesta Key Beach! This turnkey furnished, beautifully maintained 2-bedroom, 2-bathroom condo is located on the first floor and offers the perfect blend of comfort and convenience. Enjoy stunning views of the Intracoastal Waterway right from your screened lanai. The property is fully funded for reserves and has passed the required SIRS inspections, providing peace of mind for the new owner. Key Features: Turnkey Furnished: Move-in ready with everything you need. Location: Prime location on Siesta Key, just across the street from Crescent Beach and an easy walk to world-renowned Siesta Key Beach. Views: Enjoy picturesque views of the Intracoastal Waterway from your lanai. Community Amenities: Marina with dock space available for rent or purchase. Fitness center and basketball court for active living. Heated pool for year-round enjoyment. Rental Opportunities: Midnight Cove II allows 1-week rentals, offering great potential for short-term rental income. The on-site office is optionally available to handle rentals on your behalf, making it a hassle-free investment. This property is an excellent opportunity for investors or those seeking a relaxing retreat in one of Florida’s most desirable locations. Schedule your private showing today!

1800 Cove Ii Place Unit 213, Siesta Key

Listing courtesy of EXCEPTIONS REALTY. 941-315-2662

$1,349,000

Siesta Key, exclusive gated community of only 18 homes with Marina, pool and tennis all within a private, lush, tropical paradise . Walking paths around the lagoon as well as the beautiful Marina make Hamilton Club a truly unique lifestyle. Inspired by the architcture of Bermuda with its close ties to 17th Century Great Britian is recognised by its striking pastel colored walls and "welcoming arms" staircases . Very close to the Village and Beach , yet equally convenient to Downtown . This sophisticated townhome has been completly renovated with fine finishes , wood and stone prevail with architectural beauty . Soaring ceilings bring in the most elegant lighting . The kitchen with its sweeping bar of magnificent granite can accomodate a large party-open to the Great Room , it is both sleek and inviting .Premium appliances include Miele, Bosch , GE and KitchenAid .Expansive counter space , built in shelving and a variety of pantries and drawers add to the incredible functionality. The Great Room with 20 foot ceilings opens to the screened balcony with a charming view of the lagoon and pool area . The primary bedroom is enhanced by the stunning view of treetops and is all the more cozy for having its own fireplace . Impact rated windows and a metal roof combine to make this solid structure weather worthy . On the ground floor , in addition to the oversized two car gargage is a climate controlled bonus room which opens to the ground floor lanai . Boating , swimming , tennis and walking paths , within a private and peaceful environment close to everything -that is the Hamilton Club .

3 Beds ⋅ 4 Baths ⋅ A4696120 MLS ⋅ 3942 BLDG.

Siesta Key, exclusive gated community of only 18 homes with Marina, pool and tennis all within a private, lush, tropical paradise . Walking paths around the lagoon as well as the beautiful Marina make Hamilton Club a truly unique lifestyle. Inspired by the architcture of Bermuda with its close ties to 17th Century Great Britian is recognised by its striking pastel colored walls and "welcoming arms" staircases . Very close to the Village and Beach , yet equally convenient to Downtown . This sophisticated townhome has been completly renovated with fine finishes , wood and stone prevail with architectural beauty . Soaring ceilings bring in the most elegant lighting . The kitchen with its sweeping bar of magnificent granite can accomodate a large party-open to the Great Room , it is both sleek and inviting .Premium appliances include Miele, Bosch , GE and KitchenAid .Expansive counter space , built in shelving and a variety of pantries and drawers add to the incredible functionality. The Great Room with 20 foot ceilings opens to the screened balcony with a charming view of the lagoon and pool area . The primary bedroom is enhanced by the stunning view of treetops and is all the more cozy for having its own fireplace . Impact rated windows and a metal roof combine to make this solid structure weather worthy . On the ground floor , in addition to the oversized two car gargage is a climate controlled bonus room which opens to the ground floor lanai . Boating , swimming , tennis and walking paths , within a private and peaceful environment close to everything -that is the Hamilton Club .

3942 Hamilton Club Circle Unit 13, Siesta Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-349-3444

$4,795,000

Under Construction. An exceptional opportunity to own a brand-new waterfront residence in the highly sought-after Siesta Isles community. Expertly crafted by Nutter Custom Construction, this British West Indies-inspired custom home offers 3,568 square feet of air-conditioned living space and 5,725 total square feet designed for luxurious coastal living. Situated on a 14,300-square-foot lot with 104 feet of waterfront and a brand-new seawall, this thoughtfully designed residence features 4 bedrooms, 4.5 bathrooms, a 2-car garage, private pool and spa, and an expansive outdoor living area complete with a summer kitchen. Interior features include soaring 23.5-foot ceilings in the entry & foyer, 11.4-foot ceilings throughout the main living areas, custom wood beam details, wide-plank wood flooring, custom cabinetry, natural stone finishes, and a premium Thermador appliance package. The well-designed floor plan offers a first-floor primary suite, spacious great room, and seamless indoor-outdoor living. Upstairs, a flexible bonus room showcases dramatic glass corner sliders opening to a waterfront balcony with sunset views. The luxurious primary suite features a private lanai, spa-inspired bath with outdoor shower, and oversized walk-in closets. Located just minutes from Siesta Key Village and world-renowned Siesta Key Beach, this exceptional property combines the best of waterfront living with convenient access to dining, shopping, and entertainment. Buyers may have the opportunity to make select finishes and customization choices depending on the stage of construction. Estimated completion February 2027. Experience the unmatched craftsmanship and attention to detail that define every Nutter Custom Construction home.

4 Beds ⋅ 5 Baths ⋅ A4695248 MLS

Under Construction. An exceptional opportunity to own a brand-new waterfront residence in the highly sought-after Siesta Isles community. Expertly crafted by Nutter Custom Construction, this British West Indies-inspired custom home offers 3,568 square feet of air-conditioned living space and 5,725 total square feet designed for luxurious coastal living. Situated on a 14,300-square-foot lot with 104 feet of waterfront and a brand-new seawall, this thoughtfully designed residence features 4 bedrooms, 4.5 bathrooms, a 2-car garage, private pool and spa, and an expansive outdoor living area complete with a summer kitchen. Interior features include soaring 23.5-foot ceilings in the entry & foyer, 11.4-foot ceilings throughout the main living areas, custom wood beam details, wide-plank wood flooring, custom cabinetry, natural stone finishes, and a premium Thermador appliance package. The well-designed floor plan offers a first-floor primary suite, spacious great room, and seamless indoor-outdoor living. Upstairs, a flexible bonus room showcases dramatic glass corner sliders opening to a waterfront balcony with sunset views. The luxurious primary suite features a private lanai, spa-inspired bath with outdoor shower, and oversized walk-in closets. Located just minutes from Siesta Key Village and world-renowned Siesta Key Beach, this exceptional property combines the best of waterfront living with convenient access to dining, shopping, and entertainment. Buyers may have the opportunity to make select finishes and customization choices depending on the stage of construction. Estimated completion February 2027. Experience the unmatched craftsmanship and attention to detail that define every Nutter Custom Construction home.

5572 Shadow Lawn Drive, Siesta Key

Listing courtesy of NCC PROPERTIES LLC. 941-924-1868

$3,795,000

Tucked away near the end of a quiet cul-de-sac on an oversized, private waterfront lot in Siesta Isles with 109 feet of frontage on Siesta Key's Grand Canal, this exceptional 4,161-square-foot residence offers a rare combination of privacy, expansive living spaces, extensive upgrades, and breathtaking water views. Positioned at the canal's coveted "Big Bend," the home enjoys panoramic open-water vistas enhanced by neighboring county-owned green space, creating a lush natural backdrop and a remarkable sense of seclusion. Designed for both grand entertaining and everyday comfort, the light-filled floor plan features four bedrooms+bonus room, three full baths, multiple living areas, and rich wood flooring throughout. At the heart of the home is a gourmet chef's kitchen appointed with premium appliances, seamlessly connecting to an expansive great room where floor-to-ceiling glass frames stunning waterfront views. A separate entertaining bar features illuminated cabinetry, a wine refrigerator, sink, second Bosch dishwasher, and pass-through window to the lanai, making indoor-outdoor hosting effortless. The great room easily accommodates a dining table for ten while offering multiple gathering spaces to relax and enjoy the ever-changing waterfront scenery. The spacious primary suite serves as a private retreat, featuring a newly replaced waterfront deck and captivating water views from nearly every angle. Extensively upgraded with an emphasis on durability and peace of mind, the home features impact-rated windows and doors, recently replaced metal and flat roofs, two elevated HVAC systems, an elevated whole-house generator, mini-split air conditioning in the garage, two water heaters, extensive electrical upgrades, and all cast-iron sewer lines replaced with PVC. Outside, the resort-style living experience continues with expansive travertine patios, a heated saltwater pool and spa, multiple covered and open-air seating areas, and exceptional boating amenities including a new dock, 10,000-pound boat lift, and additional double jet ski/kayak lift. Professionally designed landscaping and architectural lighting enhance the home's tropical setting, creating a beautiful ambiance both day and night. With quick access to Roberts Bay and the Intracoastal Waterway, this property is perfectly suited for boating enthusiasts. Located just one mile from world-famous Siesta Key Beach and minutes from Sarasota's renowned dining, shopping, and cultural attractions, this extraordinary waterfront retreat offers the perfect blend of luxury, comfort, boating lifestyle, and privacy. This is truly A HOME FOR JOYFUL GATHERINGS!

4 Beds ⋅ 3 Baths ⋅ A4694937 MLS

Tucked away near the end of a quiet cul-de-sac on an oversized, private waterfront lot in Siesta Isles with 109 feet of frontage on Siesta Key's Grand Canal, this exceptional 4,161-square-foot residence offers a rare combination of privacy, expansive living spaces, extensive upgrades, and breathtaking water views. Positioned at the canal's coveted "Big Bend," the home enjoys panoramic open-water vistas enhanced by neighboring county-owned green space, creating a lush natural backdrop and a remarkable sense of seclusion. Designed for both grand entertaining and everyday comfort, the light-filled floor plan features four bedrooms+bonus room, three full baths, multiple living areas, and rich wood flooring throughout. At the heart of the home is a gourmet chef's kitchen appointed with premium appliances, seamlessly connecting to an expansive great room where floor-to-ceiling glass frames stunning waterfront views. A separate entertaining bar features illuminated cabinetry, a wine refrigerator, sink, second Bosch dishwasher, and pass-through window to the lanai, making indoor-outdoor hosting effortless. The great room easily accommodates a dining table for ten while offering multiple gathering spaces to relax and enjoy the ever-changing waterfront scenery. The spacious primary suite serves as a private retreat, featuring a newly replaced waterfront deck and captivating water views from nearly every angle. Extensively upgraded with an emphasis on durability and peace of mind, the home features impact-rated windows and doors, recently replaced metal and flat roofs, two elevated HVAC systems, an elevated whole-house generator, mini-split air conditioning in the garage, two water heaters, extensive electrical upgrades, and all cast-iron sewer lines replaced with PVC. Outside, the resort-style living experience continues with expansive travertine patios, a heated saltwater pool and spa, multiple covered and open-air seating areas, and exceptional boating amenities including a new dock, 10,000-pound boat lift, and additional double jet ski/kayak lift. Professionally designed landscaping and architectural lighting enhance the home's tropical setting, creating a beautiful ambiance both day and night. With quick access to Roberts Bay and the Intracoastal Waterway, this property is perfectly suited for boating enthusiasts. Located just one mile from world-famous Siesta Key Beach and minutes from Sarasota's renowned dining, shopping, and cultural attractions, this extraordinary waterfront retreat offers the perfect blend of luxury, comfort, boating lifestyle, and privacy. This is truly A HOME FOR JOYFUL GATHERINGS!

813 Idlewild Way, Siesta Key

Listing courtesy of MANGROVE REALTY ASSOCIATES. 941-957-0080

$558,000

Welcome to your own slice of paradise at Jamaica Royale, located directly on the world-famous shores of Siesta Key Beach. This beautifully remodeled one-bedroom, one-bath condominium, complete with a queen sleeper sofa, and a twin sleeper sofa, offers the perfect combination of coastal sophistication and exceptional rental income potential. Thoughtfully updated throughout, the stunning kitchen features elegant quartz countertops, custom wood cabinetry, stainless steel appliances, and a convenient laundry closet with a stackable washer and dryer—ideal for effortless beachside living and entertaining. The spa-inspired bathroom showcases designer finishes, including a custom-tiled shower and sleek quartz top vanity. Designed with both comfort and style in mind, the open and inviting floor plan is offered fully furnished and turnkey, allowing you to begin enjoying the Siesta Key lifestyle immediately. Whether you're seeking a personal beachfront getaway, an investment property, or both, this residence delivers. Jamaica Royale is one of Siesta Key's most sought-after beachfront communities, offering flexible one-week minimum rentals, making it highly attractive to vacationers and investors alike. Residents and guests enjoy 3 heated community pools, designated BBQ areas, a shuffleboard court and approximately 300 feet of private beachfront, with direct access to the Gulf of Mexico's crystal-clear waters and powder-soft quartz sand. Perfectly positioned just minutes from Siesta Key Village, you'll enjoy easy access to award-winning restaurants, charming boutiques, entertainment, and vibrant nightlife. This is a rare opportunity to own a turnkey beachfront retreat in one of Florida's most desirable coastal destinations—where every day feels like a vacation.

1 Beds ⋅ 1 Baths ⋅ A4695273 MLS

Welcome to your own slice of paradise at Jamaica Royale, located directly on the world-famous shores of Siesta Key Beach. This beautifully remodeled one-bedroom, one-bath condominium, complete with a queen sleeper sofa, and a twin sleeper sofa, offers the perfect combination of coastal sophistication and exceptional rental income potential. Thoughtfully updated throughout, the stunning kitchen features elegant quartz countertops, custom wood cabinetry, stainless steel appliances, and a convenient laundry closet with a stackable washer and dryer—ideal for effortless beachside living and entertaining. The spa-inspired bathroom showcases designer finishes, including a custom-tiled shower and sleek quartz top vanity. Designed with both comfort and style in mind, the open and inviting floor plan is offered fully furnished and turnkey, allowing you to begin enjoying the Siesta Key lifestyle immediately. Whether you're seeking a personal beachfront getaway, an investment property, or both, this residence delivers. Jamaica Royale is one of Siesta Key's most sought-after beachfront communities, offering flexible one-week minimum rentals, making it highly attractive to vacationers and investors alike. Residents and guests enjoy 3 heated community pools, designated BBQ areas, a shuffleboard court and approximately 300 feet of private beachfront, with direct access to the Gulf of Mexico's crystal-clear waters and powder-soft quartz sand. Perfectly positioned just minutes from Siesta Key Village, you'll enjoy easy access to award-winning restaurants, charming boutiques, entertainment, and vibrant nightlife. This is a rare opportunity to own a turnkey beachfront retreat in one of Florida's most desirable coastal destinations—where every day feels like a vacation.

5830 Midnight Pass Road Unit 48, Siesta Key

Listing courtesy of PEPPERTREE BAY REALTY INC. 941-349-7777

$449,000

Welcome to Unit 201 at White Sands Condominium — a bright, airy coastal retreat perfectly positioned on iconic Midnight Pass Road, Siesta Key. This spacious 1,012 sq ft, two-bedroom, two-bathroom condo is your gateway to the laid-back island lifestyle you've been dreaming of. Whether you choose to walk, cycle, or simply stroll, the world-famous Siesta Key Beach — voted the #1 beach in the USA — is just moments from your front door. Step inside and feel immediately at home. Generous natural light floods the open living spaces, beautifully complemented by wood-look flooring that runs throughout the unit, giving it a polished feel with all the ease of coastal living. The thoughtful layout offers two full bathrooms plus a convenient in-unit washer and dryer, so laundry day never interrupts island day. A dedicated storage closet rounds things out, giving you that extra breathing room that makes everyday life so much easier. When the sun starts to dip and the breeze picks up, step out onto your private covered lanai — the ideal spot to mix a cocktail, host friends, or simply let the Siesta Key evening wash over you. Sheltered and spacious, it extends your living space outdoors in true Florida fashion, and is the kind of feature you'll use every single day. Beyond your front door, White Sands offers a wonderful sense of community. Take a dip in the sparkling community pool, or take advantage of the community boat docks — available on a first-come, first-served basis — perfect for those who love life on the water. And with your own deeded covered parking spot, convenience is always part of the package. This is more than a condo — it's a front-row seat to everything that makes Siesta Key one of Florida's most sought-after addresses. Whether you're looking for a full-time residence, a vacation escape, or a smart investment, Unit 201 checks every box.

2 Beds ⋅ 2 Baths ⋅ A4694956 MLS ⋅ Na BLDG.

Welcome to Unit 201 at White Sands Condominium — a bright, airy coastal retreat perfectly positioned on iconic Midnight Pass Road, Siesta Key. This spacious 1,012 sq ft, two-bedroom, two-bathroom condo is your gateway to the laid-back island lifestyle you've been dreaming of. Whether you choose to walk, cycle, or simply stroll, the world-famous Siesta Key Beach — voted the #1 beach in the USA — is just moments from your front door. Step inside and feel immediately at home. Generous natural light floods the open living spaces, beautifully complemented by wood-look flooring that runs throughout the unit, giving it a polished feel with all the ease of coastal living. The thoughtful layout offers two full bathrooms plus a convenient in-unit washer and dryer, so laundry day never interrupts island day. A dedicated storage closet rounds things out, giving you that extra breathing room that makes everyday life so much easier. When the sun starts to dip and the breeze picks up, step out onto your private covered lanai — the ideal spot to mix a cocktail, host friends, or simply let the Siesta Key evening wash over you. Sheltered and spacious, it extends your living space outdoors in true Florida fashion, and is the kind of feature you'll use every single day. Beyond your front door, White Sands offers a wonderful sense of community. Take a dip in the sparkling community pool, or take advantage of the community boat docks — available on a first-come, first-served basis — perfect for those who love life on the water. And with your own deeded covered parking spot, convenience is always part of the package. This is more than a condo — it's a front-row seat to everything that makes Siesta Key one of Florida's most sought-after addresses. Whether you're looking for a full-time residence, a vacation escape, or a smart investment, Unit 201 checks every box.

5673 Midnight Pass Road Unit 201, Siesta Key

Listing courtesy of COLDWELL BANKER REALTY. 941-366-8070

$469,900

This second floor 2-bedroom, 2 bath condo is located in the Marlin House in the 55+ community of wonderful Siesta Harbor! This unit offers an open floor plan with plenty of light. Step out onto one of the balcony’s to view the peaceful water, boats going by and you may see dolphins playing while you are enjoying your morning beverage. This community offers more than just serene water views. Included in the many amenities are a heated pool, shuffleboard, library and a fitness area. Feel free to participate in movie night, Tai Chi and Happy Hour along with many other activities offered at the clubhouse. Are you a boater? Siesta Harbor is one of the few condos on Siesta Key that offers a boat dock with deep water, for those interested in this bonus extra. If you wish to walk to the beautiful Siesta Key beach, voted best beach in the USA and the world, private access right across the street through a deeded access. Siesta Harbor keeps its grounds and buildings well maintained, recently updated with new roofs and updated common areas. This unit is a must have, with the deep water of the Intracoastal Waterway right in your backyard, the peaceful and serene atmosphere of the area, the beautiful beach just a shore walk away and it can be an income producer should that be something you want to consider.

2 Beds ⋅ 2 Baths ⋅ A4695140 MLS ⋅ Marlin BLDG.

This second floor 2-bedroom, 2 bath condo is located in the Marlin House in the 55+ community of wonderful Siesta Harbor! This unit offers an open floor plan with plenty of light. Step out onto one of the balcony’s to view the peaceful water, boats going by and you may see dolphins playing while you are enjoying your morning beverage. This community offers more than just serene water views. Included in the many amenities are a heated pool, shuffleboard, library and a fitness area. Feel free to participate in movie night, Tai Chi and Happy Hour along with many other activities offered at the clubhouse. Are you a boater? Siesta Harbor is one of the few condos on Siesta Key that offers a boat dock with deep water, for those interested in this bonus extra. If you wish to walk to the beautiful Siesta Key beach, voted best beach in the USA and the world, private access right across the street through a deeded access. Siesta Harbor keeps its grounds and buildings well maintained, recently updated with new roofs and updated common areas. This unit is a must have, with the deep water of the Intracoastal Waterway right in your backyard, the peaceful and serene atmosphere of the area, the beautiful beach just a shore walk away and it can be an income producer should that be something you want to consider.

1250 N Portofino Drive Unit 202, Siesta Key

Listing courtesy of BECKMANN REAL ESTATE. 941-346-3500

$529,900

This property is a rare find, featuring two master suites upstairs, each with its own private balcony. The home is tastefully decorated and is being sold Turnkey, making it an excellent opportunity for immediate use or investment. Notably, the property already has a strong track record of rental income with several future bookings already in place. The Bay Oaks community offers a serene setting with mature landscaping and a wide array of amenities, including a heated pool, tennis courts, recreation room and a fishing pier. It also provides the convenience of on-site management and a picnic area with Barbeques for your enjoyment. Located less than a mile from Crescent Beach, the property offers easy access to the world-renowned powdery, quartz sand of Siesta Key, recently ranked as the #4 beach in the world by Tripadvisor in 2025. The area is a premier destination spot. Additionally, the trolley stops directly in front of the complex providing easy transportation to the various dining, shopping and nightlife options Siesta Key is famous for.

2 Beds ⋅ 3 Baths ⋅ A4692762 MLS ⋅ Na BLDG.

This property is a rare find, featuring two master suites upstairs, each with its own private balcony. The home is tastefully decorated and is being sold Turnkey, making it an excellent opportunity for immediate use or investment. Notably, the property already has a strong track record of rental income with several future bookings already in place. The Bay Oaks community offers a serene setting with mature landscaping and a wide array of amenities, including a heated pool, tennis courts, recreation room and a fishing pier. It also provides the convenience of on-site management and a picnic area with Barbeques for your enjoyment. Located less than a mile from Crescent Beach, the property offers easy access to the world-renowned powdery, quartz sand of Siesta Key, recently ranked as the #4 beach in the world by Tripadvisor in 2025. The area is a premier destination spot. Additionally, the trolley stops directly in front of the complex providing easy transportation to the various dining, shopping and nightlife options Siesta Key is famous for.

6157 Midnight Pass Road Unit F22, Siesta Key

Listing courtesy of BECKMANN REAL ESTATE. 941-346-3500

$1,850,000

TOP FLOOR. TOP BEACH. TOP NOTCH. This Siesta Key condo checks ALL the hard to find boxes — THREE bedrooms. PRIVATE Beach. TOP Floor. RESORT Style Amenities. GARAGE Parking Space. NO Work Needed! Welcome to Unit 907, a beautifully refreshed top-floor residence offering generous living space, a calm coastal feel, and the easy beach lifestyle buyers are looking for. From the moment you open the door, the residence feels bright, relaxed, and beautifully pulled together with updated coastal furnishings and a soft beachside palette. Spacious living and dining areas create an easy flow for everyday enjoyment or extended stays, while the kitchen offers quartz countertops, stainless appliances, breakfast bar, and generous storage. The Master Bedroom has spectacular gulf views, ensuite with double sinks, walk-in shower, and a spacious closet. The split-bedroom floor plan with two guest bedrooms provides privacy and flexibility for guests, or home office, hobbies, and additional storage. The Casarina community has recently completed significant improvements which include a new roof, elevator updates, electrical updates, new A/C units, flood-prevention panels, new carport roofs, refreshed landscaping, new driveway and pool pavers, new grilling area, and more — assessments already paid by seller! Get ready to enjoy approximately 7 acres of tropical grounds, direct access to Siesta Key's powdery-soft, white sand beach, heated pool and spa, clubhouse, fitness room, tennis and pickleball courts, basketball, BBQ areas, onsite management, secured access, two elevators, and beautifully maintained outdoor spaces. Minutes from Siesta Key Village, dining, shopping, and downtown Sarasota. Contact me today to schedule your private tour and start living the Siesta Key lifestyle you've always dreamed of.

3 Beds ⋅ 2 Baths ⋅ A4694262 MLS ⋅ 5880 BLDG.

TOP FLOOR. TOP BEACH. TOP NOTCH. This Siesta Key condo checks ALL the hard to find boxes — THREE bedrooms. PRIVATE Beach. TOP Floor. RESORT Style Amenities. GARAGE Parking Space. NO Work Needed! Welcome to Unit 907, a beautifully refreshed top-floor residence offering generous living space, a calm coastal feel, and the easy beach lifestyle buyers are looking for. From the moment you open the door, the residence feels bright, relaxed, and beautifully pulled together with updated coastal furnishings and a soft beachside palette. Spacious living and dining areas create an easy flow for everyday enjoyment or extended stays, while the kitchen offers quartz countertops, stainless appliances, breakfast bar, and generous storage. The Master Bedroom has spectacular gulf views, ensuite with double sinks, walk-in shower, and a spacious closet. The split-bedroom floor plan with two guest bedrooms provides privacy and flexibility for guests, or home office, hobbies, and additional storage. The Casarina community has recently completed significant improvements which include a new roof, elevator updates, electrical updates, new A/C units, flood-prevention panels, new carport roofs, refreshed landscaping, new driveway and pool pavers, new grilling area, and more — assessments already paid by seller! Get ready to enjoy approximately 7 acres of tropical grounds, direct access to Siesta Key's powdery-soft, white sand beach, heated pool and spa, clubhouse, fitness room, tennis and pickleball courts, basketball, BBQ areas, onsite management, secured access, two elevators, and beautifully maintained outdoor spaces. Minutes from Siesta Key Village, dining, shopping, and downtown Sarasota. Contact me today to schedule your private tour and start living the Siesta Key lifestyle you've always dreamed of.

5880 Midnight Pass Road Unit 907, Siesta Key

Listing courtesy of COLDWELL BANKER REALTY. 941-349-4411

$515,000

Welcome to White Sands. Whether you're searching for a profitable investment opportunity or your own private island retreat, this property offers the best of both worlds. Ideally located directly across from world-famous Siesta Key Beach where you will conveniently find pickleball, tennis, volleyball and a playground. This turn-key, pet-friendly furnished completely remodeled 2/2 condominium features an open-concept design filled with natural light and generous living space, creating the perfect coastal getaway. The unit includes 2023 HOT WATER HEATER, 2024 RE-PIPED KITCHEN AND BATHROOMS, 2024 INTERIOR PAINT, 2024 AC, 2024 CEILING FANS, 2025 NEW LIGHTING IN MASTER BEDROOM AND MASTER BATHROOM, 2024 NEW FURNITURE AND TVS, 2024 NEW TILE FLOORING SECOND BEDROOM. The spacious primary suite offers an en-suite bath and ample closet space, while the guest bedroom provides flexibility for visitors, a home office, or additional rental accommodations. Move-in ready, this unit is ideal as a full-time residence, seasonal escape, or income-producing vacation rental. On-site management is available for both rentals and maintenance, adding convenience and peace of mind for owners and guests alike. Residents enjoy resort-style amenities including multiple laundry facilities, designated shaded carport parking spaces in addition to plenty of open guest parking, heated community pool, clubhouse, sauna, BBQ grills, private beach access, and boat docks available annually on a first-come basis. The property allows rentals every two weeks throughout the year, offering excellent income potential. Don't miss out on this exceptional Siesta Key lifestyle opportunity!

2 Beds ⋅ 2 Baths ⋅ A4693474 MLS ⋅ 5619 BLDG.

Welcome to White Sands. Whether you're searching for a profitable investment opportunity or your own private island retreat, this property offers the best of both worlds. Ideally located directly across from world-famous Siesta Key Beach where you will conveniently find pickleball, tennis, volleyball and a playground. This turn-key, pet-friendly furnished completely remodeled 2/2 condominium features an open-concept design filled with natural light and generous living space, creating the perfect coastal getaway. The unit includes 2023 HOT WATER HEATER, 2024 RE-PIPED KITCHEN AND BATHROOMS, 2024 INTERIOR PAINT, 2024 AC, 2024 CEILING FANS, 2025 NEW LIGHTING IN MASTER BEDROOM AND MASTER BATHROOM, 2024 NEW FURNITURE AND TVS, 2024 NEW TILE FLOORING SECOND BEDROOM. The spacious primary suite offers an en-suite bath and ample closet space, while the guest bedroom provides flexibility for visitors, a home office, or additional rental accommodations. Move-in ready, this unit is ideal as a full-time residence, seasonal escape, or income-producing vacation rental. On-site management is available for both rentals and maintenance, adding convenience and peace of mind for owners and guests alike. Residents enjoy resort-style amenities including multiple laundry facilities, designated shaded carport parking spaces in addition to plenty of open guest parking, heated community pool, clubhouse, sauna, BBQ grills, private beach access, and boat docks available annually on a first-come basis. The property allows rentals every two weeks throughout the year, offering excellent income potential. Don't miss out on this exceptional Siesta Key lifestyle opportunity!

5619 Midnight Pass Road Unit 503, Siesta Key

Listing courtesy of PREFERRED SHORE LLC. 941-999-1179

$449,900

Welcome to Jamaica Royale, a Gulf-side development on Siesta Key, with its award-winning, crystal powder soft sandy beach, just nearby. This studio offers a main-floor villa that has been renovated for comfort and durability. Enjoy the new kitchen with new stainless steel appliances, quartz counters throughout and a new bath. All furnishings have been tastefully replaced with a focus on quality and functionality. The water heater is new, freshly painted, and waiting for its new owner. The location of the rear patio is conveniently near one of three pools. An on-site office offers an optional rental program, so you may generate potential income when not in residence. While you go out your rear patio to the beach, you will pass Jamaica Royale's additional pools, beach cabana and white sands of Siesta Key. The clubhouse offers a full kitchen, a meeting room, on-site association services and rental management. Outside offers barbecue grills, a table and chairs, a lounging area and shuffleboard, a great area to gather with family and friends. Siesta Key offers public transportation to many of the area's local coastal attractions, restaurants, shopping and Sarasota, with all that it offers.

1 Baths ⋅ A4694962 MLS ⋅ Jamaica Royale BLDG.

Welcome to Jamaica Royale, a Gulf-side development on Siesta Key, with its award-winning, crystal powder soft sandy beach, just nearby. This studio offers a main-floor villa that has been renovated for comfort and durability. Enjoy the new kitchen with new stainless steel appliances, quartz counters throughout and a new bath. All furnishings have been tastefully replaced with a focus on quality and functionality. The water heater is new, freshly painted, and waiting for its new owner. The location of the rear patio is conveniently near one of three pools. An on-site office offers an optional rental program, so you may generate potential income when not in residence. While you go out your rear patio to the beach, you will pass Jamaica Royale's additional pools, beach cabana and white sands of Siesta Key. The clubhouse offers a full kitchen, a meeting room, on-site association services and rental management. Outside offers barbecue grills, a table and chairs, a lounging area and shuffleboard, a great area to gather with family and friends. Siesta Key offers public transportation to many of the area's local coastal attractions, restaurants, shopping and Sarasota, with all that it offers.

5830 Midnight Pass Road Unit 32, Siesta Key

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY. 941-364-4000

$1,100,000

Experience the best of beachfront living at Gulf & Bay Club, one of Siesta Key's premier Gulf-front communities on the world-famous white quartz sands of Siesta Key Beach. This beautiful ground-floor residence offers 2 bedrooms/2 baths, office area, dining & living rooms, and in unit laundry - all surrounded by lush tropical landscaping that creates a peaceful, private setting. The open-concept floor plan features warm coastal finishes, crown molding, and an updated kitchen with newer appliances, abundant cabinetry, a convenient beverage cooler, and an in-unit LG washer/dryer. Expansive sliding glass doors fill the home with natural light while showcasing views of two lagoon fountains, tropical landscaping, and partial Gulf views that provide spectacular sunset backdrops. Recent updates include an A/C (Nov. 2021), hot water heater (Mar. 2026), and GE microwave (2025). Ideally located just steps from one of the community's grilling areas, this residence offers the perfect blend of comfort and convenience. Gulf & Bay Club is a gated 32-acre beachfront community with 800 feet of private Gulf frontage and exceptional resort-style amenities, including three heated pools, two clubhouses, a fitness center, hot tub, dry saunas, eight tennis courts, racquetball and basketball courts, a scenic lagoon with a charming island, electric vehicle charging stations, and an active social calendar with organized events and activities. Whether you're looking for a full-time residence, vacation retreat, or investment opportunity, this exceptional condominium offers the ultimate Siesta Key lifestyle.

2 Beds ⋅ 2 Baths ⋅ A4693221 MLS ⋅ B BLDG.

Experience the best of beachfront living at Gulf & Bay Club, one of Siesta Key's premier Gulf-front communities on the world-famous white quartz sands of Siesta Key Beach. This beautiful ground-floor residence offers 2 bedrooms/2 baths, office area, dining & living rooms, and in unit laundry - all surrounded by lush tropical landscaping that creates a peaceful, private setting. The open-concept floor plan features warm coastal finishes, crown molding, and an updated kitchen with newer appliances, abundant cabinetry, a convenient beverage cooler, and an in-unit LG washer/dryer. Expansive sliding glass doors fill the home with natural light while showcasing views of two lagoon fountains, tropical landscaping, and partial Gulf views that provide spectacular sunset backdrops. Recent updates include an A/C (Nov. 2021), hot water heater (Mar. 2026), and GE microwave (2025). Ideally located just steps from one of the community's grilling areas, this residence offers the perfect blend of comfort and convenience. Gulf & Bay Club is a gated 32-acre beachfront community with 800 feet of private Gulf frontage and exceptional resort-style amenities, including three heated pools, two clubhouses, a fitness center, hot tub, dry saunas, eight tennis courts, racquetball and basketball courts, a scenic lagoon with a charming island, electric vehicle charging stations, and an active social calendar with organized events and activities. Whether you're looking for a full-time residence, vacation retreat, or investment opportunity, this exceptional condominium offers the ultimate Siesta Key lifestyle.

5780 Midnight Pass Road Unit B105, Siesta Key

Listing courtesy of ANDREWS & ASSOCIATES REALTY. 941-921-5999

$100,000

Fractional Ownership. Unique opportunity to own four consecutive weeks in March on Siesta Key Beach. Experience luxury beachfront living with this Winter Fractional Package, offering a 1/8th ownership share at The Residences on Siesta Key Beach. This rare offering provides the opportunity to own a piece of paradise on one of America’s most celebrated beaches while enjoying the comfort, convenience, and elevated service of a luxury resort. This expansive residence features a primary suite, a junior suite and beautifully updated custom furnishings valued at more than $150,000. The fully equipped kitchen is appointed with premium Wolf, Sub-Zero, and Fisher & Paykel appliances, complemented by imported linens and thoughtful details throughout. Owners enjoy the legendary hospitality and services of Hyatt Vacation Club, including daily complimentary continental breakfast, beach service, recreation and front desk staff, assistance with local activities, valet parking, and 24-hour security. Enjoy the best of Siesta Key beachfront living with resort-style amenities, full-service convenience, and luxury condominium ownership, all at a fraction of the cost.

2 Beds ⋅ 3 Baths ⋅ A4694774 MLS ⋅ Hyatt Residences On Siesta Key BLDG.

Fractional Ownership. Unique opportunity to own four consecutive weeks in March on Siesta Key Beach. Experience luxury beachfront living with this Winter Fractional Package, offering a 1/8th ownership share at The Residences on Siesta Key Beach. This rare offering provides the opportunity to own a piece of paradise on one of America’s most celebrated beaches while enjoying the comfort, convenience, and elevated service of a luxury resort. This expansive residence features a primary suite, a junior suite and beautifully updated custom furnishings valued at more than $150,000. The fully equipped kitchen is appointed with premium Wolf, Sub-Zero, and Fisher & Paykel appliances, complemented by imported linens and thoughtful details throughout. Owners enjoy the legendary hospitality and services of Hyatt Vacation Club, including daily complimentary continental breakfast, beach service, recreation and front desk staff, assistance with local activities, valet parking, and 24-hour security. Enjoy the best of Siesta Key beachfront living with resort-style amenities, full-service convenience, and luxury condominium ownership, all at a fraction of the cost.

915 Seaside Drive Unit 402, Weeks 10-13, Siesta Key

Listing courtesy of DOUGLAS ELLIMAN. 941-867-6199