Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.

4 Beds ⋅ 4 Baths ⋅ A4680006 MLS

Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.

1005 Bogey Lane, Longboat Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-383-7591

$550,000

Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.

2 Beds ⋅ 2 Baths ⋅ TB8455704 MLS ⋅ Bldg L BLDG.

Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.

4420 Exeter Drive Unit 303, Longboat Key

Listing courtesy of SMITH & ASSOCIATES REAL ESTATE. 727-342-3800

$1,395,000

Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property delivers rare privacy and an elevated coastal lifestyle. Beach chairs, tables, and umbrellas are provided, making it easy to step outside and enjoy the sand shoreline just moments from your door. The residence offers both elevator and stair access, one assigned covered parking space under the building and convenient guest parking. Owners enjoy resort-style amenities including in ground salt water pool and spa, tennis and pickleball courts, a library and a clubhouse with indoor and outdoor kitchen spaces, perfect for entertaining or relaxing after a day on the water. Ideally positioned on coveted Gulf of Mexico Drive, this prime location places you steps from the St. Regis, minutes to Publix and the world-class dining and shopping of St. Armands Circle. Whether as a full-time residence, seasonal escape or investment opportunity, this condo offers the very best of Longboat Key living- private, serene, and undeniably beautiful. A rare opportunity to own a Gulf-front condo in one of Longboat Key’s most desirable beachfront communities.

2 Beds ⋅ 3 Baths ⋅ A4679674 MLS ⋅ Players Club 1 BLDG.

Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property delivers rare privacy and an elevated coastal lifestyle. Beach chairs, tables, and umbrellas are provided, making it easy to step outside and enjoy the sand shoreline just moments from your door. The residence offers both elevator and stair access, one assigned covered parking space under the building and convenient guest parking. Owners enjoy resort-style amenities including in ground salt water pool and spa, tennis and pickleball courts, a library and a clubhouse with indoor and outdoor kitchen spaces, perfect for entertaining or relaxing after a day on the water. Ideally positioned on coveted Gulf of Mexico Drive, this prime location places you steps from the St. Regis, minutes to Publix and the world-class dining and shopping of St. Armands Circle. Whether as a full-time residence, seasonal escape or investment opportunity, this condo offers the very best of Longboat Key living- private, serene, and undeniably beautiful. A rare opportunity to own a Gulf-front condo in one of Longboat Key’s most desirable beachfront communities.

1485 Gulf Of Mexico Drive Unit 303, Longboat Key

Listing courtesy of COLDWELL BANKER REALTY. 941-383-6411

$4,400,000

Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast. Sellers will repaint exterior of house whatever color Buyer selects before closing, upon firm executed Contract.

4 Beds ⋅ 4 Baths ⋅ A4666688 MLS

Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast. Sellers will repaint exterior of house whatever color Buyer selects before closing, upon firm executed Contract.

1571 Harbor Cay Lane, Longboat Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-388-4447

$2,000,000

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond three estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home, nearly one acre of land, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 280 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and the sparkling waters of the Gulf of Mexico await. Ideally just a short drive from the shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island and all the Sarasota–Bradenton area has to offer, you really can have it all.

A4679439 MLS

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond three estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home, nearly one acre of land, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 280 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and the sparkling waters of the Gulf of Mexico await. Ideally just a short drive from the shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island and all the Sarasota–Bradenton area has to offer, you really can have it all.

6604-6608 Gulf Of Mexico Drive, Longboat Key

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

$1,000,000

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond two estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home. With the additional purchase of the adjacent lot at 6608 Gulf of Mexico Drive, nearly one acre of land can be assembled, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 140 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and sparkling waters of the Gulf of Mexico await. Ideally just a short drive from the shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island, and all the Sarasota–Bradenton area has to offer, you really can have it all.

A4679437 MLS

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond two estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home. With the additional purchase of the adjacent lot at 6608 Gulf of Mexico Drive, nearly one acre of land can be assembled, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 140 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and sparkling waters of the Gulf of Mexico await. Ideally just a short drive from the shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island, and all the Sarasota–Bradenton area has to offer, you really can have it all.

6608 Gulf Of Mexico Drive, Longboat Key

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

$1,000,000

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond three estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home. With the additional purchase of adjacent lot at 6608 Gulf of Mexico Drive, nearly one acre of land can be assembled, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 140 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and sparkling waters of the Gulf of Mexico await. Ideally just a short drive from shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island and all the Sarasota–Bradenton area has to offer, you really can have it all.

A4679263 MLS

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond three estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home. With the additional purchase of adjacent lot at 6608 Gulf of Mexico Drive, nearly one acre of land can be assembled, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 140 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and sparkling waters of the Gulf of Mexico await. Ideally just a short drive from shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island and all the Sarasota–Bradenton area has to offer, you really can have it all.

6604 Gulf Of Mexico Drive, Longboat Key

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

$1,460,000

Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle. Extremely well managed building- all improvements have been completed!

2 Beds ⋅ 4 Baths ⋅ A4678941 MLS ⋅ Building Ii BLDG.

Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle. Extremely well managed building- all improvements have been completed!

3040 Grand Bay Boulevard Unit 213, Longboat Key

Listing courtesy of COMPASS FLORIDA LLC. 941-279-3630

$13,995,000

This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.

4 Beds ⋅ 5 Baths ⋅ A4677413 MLS

This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.

6489 Gulfside Road, Longboat Key

Listing courtesy of COLDWELL BANKER REALTY. 941-383-6411

$225,000

Quick access to dock you boat! Located just inside the marina on the east side. This 48 x 20 foot slip at Longboat Key Club Moorings is located on the north side of P-dock. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 43 LOA; beam depends on the vessel. Call for more information.

A4678265 MLS

Quick access to dock you boat! Located just inside the marina on the east side. This 48 x 20 foot slip at Longboat Key Club Moorings is located on the north side of P-dock. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 43 LOA; beam depends on the vessel. Call for more information.

2600 Harbourside Drive Unit P-07, Longboat Key

Listing courtesy of LBRE LLC. 941-383-8383

$499,000

Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!

1 Beds ⋅ 1 Baths ⋅ A4676730 MLS ⋅ 1 BLDG.

Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!

5231 Gulf Of Mexico Drive Unit 104, Longboat Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-383-7591

$675,000

LOCATION, LOCATION, LOCATION!!! Discover a rare and recently cleared premium homesite located on one of Longboat Key’s most charming and historic streets. This exclusive New Pass Shores community features only 6 homes, providing an intimate neighborhood atmosphere. While this homesite is not directly on the waterfront, it includes a NEW composite wood boat dock shared with just 3 other homes, granting you fishing and boating access or a peaceful retreat to enjoy the beauty of Sarasota Bay's waters and wildlife. This property represents the perfect blend of luxury, convenience, and serene coastal living, making it an ideal location to build your dream home or investment property. Nestled on the highly sought-after southernmost part of the key, it is within walking and biking distance to both Sarasota Bay and the beach. Living on Longboat Key means more than a home — it’s a lifestyle. From the pristine beaches and world-class golf and tennis at the Resort at Longboat Key Club (membership required) to boutique shopping and fine dining on St. Armand's Circle, and cultural attractions just minutes away in Sarasota, you’ll enjoy the perfect balance of island tranquility and vibrant city life as well as quick access to SRQ airport! All measurements are approximate; it is the buyer's responsibility to verify the boundaries and accuracy of all information provided

A4676908 MLS

LOCATION, LOCATION, LOCATION!!! Discover a rare and recently cleared premium homesite located on one of Longboat Key’s most charming and historic streets. This exclusive New Pass Shores community features only 6 homes, providing an intimate neighborhood atmosphere. While this homesite is not directly on the waterfront, it includes a NEW composite wood boat dock shared with just 3 other homes, granting you fishing and boating access or a peaceful retreat to enjoy the beauty of Sarasota Bay's waters and wildlife. This property represents the perfect blend of luxury, convenience, and serene coastal living, making it an ideal location to build your dream home or investment property. Nestled on the highly sought-after southernmost part of the key, it is within walking and biking distance to both Sarasota Bay and the beach. Living on Longboat Key means more than a home — it’s a lifestyle. From the pristine beaches and world-class golf and tennis at the Resort at Longboat Key Club (membership required) to boutique shopping and fine dining on St. Armand's Circle, and cultural attractions just minutes away in Sarasota, you’ll enjoy the perfect balance of island tranquility and vibrant city life as well as quick access to SRQ airport! All measurements are approximate; it is the buyer's responsibility to verify the boundaries and accuracy of all information provided

525 Channel Lane, Longboat Key

Listing courtesy of VUE REALTY, LLC. 941-269-8400

$3,499,900

Virtually Staged. A rare opportunity to own a single-family waterfront home with 100 feet of canal frontage and direct access to Sarasota Bay. Located in Country Club Shores on the desirable southern end of Longboat Key, 562 Ranger Lane offers 4 bedrooms, 3 full baths, and approximately 3,149 square feet of living space designed for relaxed coastal living. The property features a sunny southern rear exposure overlooking the canal, with a north-facing street frontage, providing balanced natural light throughout the day. The home underwent a comprehensive renovation in 2018, including a tile roof, paver driveway, two Trane A/C units, tankless water heater, updated sprinkler system, railings, pool equipment, and a Pebble Tec refinished pool positioned to maximize the southern exposure. The interior features an open great-room layout with 16-foot ceilings, porcelain tile flooring throughout, plantation shutters, LED lighting, and a spacious kitchen with Starmark solid-wood soft-close cabinetry, Cambria quartz countertops, and stainless-steel appliances. An 8-foot arched iron front door introduces abundant natural light and an open, functional floor plan. The current configuration includes an upper-level primary suite with solid oak flooring, walk-in closets, and a well-appointed bath, while the first level offers three large bedrooms, including an office with custom built-ins, and two full baths with handcrafted cabinetry, quartz countertops, and glass-enclosed showers. The flexible layout provides the opportunity to create a first-floor primary suite to suit individual lifestyle needs. Boating amenities include a new seawall, a 70-foot private Trex dock with 50-amp shore power, and a recently serviced 10,000-pound boat lift. Outdoor living is enhanced by a covered lanai and a two-level travertine deck ideal for entertaining and enjoying the canal setting. Residents enjoy access to a private deeded beach on the Gulf of Mexico and proximity to Longboat Key Club golf, dining, and shopping at St. Armands Circle, with downtown Sarasota’s cultural arts and dining scene just minutes away. Schedule a private showing to experience this waterfront home, its flexible living options, and direct access to Sarasota Bay

4 Beds ⋅ 3 Baths ⋅ A4675541 MLS

Virtually Staged. A rare opportunity to own a single-family waterfront home with 100 feet of canal frontage and direct access to Sarasota Bay. Located in Country Club Shores on the desirable southern end of Longboat Key, 562 Ranger Lane offers 4 bedrooms, 3 full baths, and approximately 3,149 square feet of living space designed for relaxed coastal living. The property features a sunny southern rear exposure overlooking the canal, with a north-facing street frontage, providing balanced natural light throughout the day. The home underwent a comprehensive renovation in 2018, including a tile roof, paver driveway, two Trane A/C units, tankless water heater, updated sprinkler system, railings, pool equipment, and a Pebble Tec refinished pool positioned to maximize the southern exposure. The interior features an open great-room layout with 16-foot ceilings, porcelain tile flooring throughout, plantation shutters, LED lighting, and a spacious kitchen with Starmark solid-wood soft-close cabinetry, Cambria quartz countertops, and stainless-steel appliances. An 8-foot arched iron front door introduces abundant natural light and an open, functional floor plan. The current configuration includes an upper-level primary suite with solid oak flooring, walk-in closets, and a well-appointed bath, while the first level offers three large bedrooms, including an office with custom built-ins, and two full baths with handcrafted cabinetry, quartz countertops, and glass-enclosed showers. The flexible layout provides the opportunity to create a first-floor primary suite to suit individual lifestyle needs. Boating amenities include a new seawall, a 70-foot private Trex dock with 50-amp shore power, and a recently serviced 10,000-pound boat lift. Outdoor living is enhanced by a covered lanai and a two-level travertine deck ideal for entertaining and enjoying the canal setting. Residents enjoy access to a private deeded beach on the Gulf of Mexico and proximity to Longboat Key Club golf, dining, and shopping at St. Armands Circle, with downtown Sarasota’s cultural arts and dining scene just minutes away. Schedule a private showing to experience this waterfront home, its flexible living options, and direct access to Sarasota Bay

562 Ranger Lane, Longboat Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-748-6300

$649,999

This beautifully maintained, ground-floor 2-bedroom, 2-bathroom condo in the desirable Banyan Bay Club offers an exceptional opportunity to own a spacious, modern / updated, move-in-ready home perfectly positioned in a charming, pet-friendly gulf-to-bay community. This unit combines convenience, amenities, and a relaxed coastal lifestyle—all at an outstanding location. This Banyan Bay condominium has an open floor plan with plank style ceramic tile throughout, recently updated featuring new cabinets, vanities, quartzite/quartz countertops and new stainless steel appliances; new Central Air system, and new hot water heater, in-unit full-size washer & dryer, modern tile design in bath, extra sleeping nook for added flexibility, tastefully furnished (can be sold furnished), private patio nestled under a majestic banyan tree-ideal for morning coffee or evening cocktails, large glass hurricane sliders & windows offering a garden view, fiber optic internet included for each unit. SQUARE FOOTAGE IN SLEEPING NOOK IS ADDED TO MAKE THE INTERIOR SQ FTG 1163. The resort-Style Community Amenities (steps from your door): heated community swimming pool, newly resurfaced tennis and pickleball court, fully equipped fitness center, clubhouse with social hall and full kitchen, new day dock, fishing pier, kayak/paddleboard launch, & storage, private gulf beach access with complimentary lounge chairs on the sand, assigned covered carport parking plus ample guest parking, exterior storage for beach gear, on-site manager and carefree exterior maintenance handled by the association, bicycle storage and mature tropical landscaping with giant banyan trees. Unbeatable Location-why Mid-Key is Best! Everything you need is within walking distance; numerous restaurants & cafes, boutiques, beautiful Durante Park with shaded trails and playground, 3 minute walk to your private Gulf beach, 1-minute walk to the community pool, gym, clubhouse, and courts,. This 44-unit condominium offers a social atmosphere, plenty of activities, up to 2 pets allowed (no weight or size limit). Whether you are seeking a full-time residence, vacation getaway, second home or investment property (valued returning renter’s incomes can offset HOA fees), this immaculate condo is ready for you to move in and start enjoying the island lifestyle today. Don't miss this combination of location, amenities and value on Longboat Key!

2 Beds ⋅ 2 Baths ⋅ A4677090 MLS ⋅ Na BLDG.

This beautifully maintained, ground-floor 2-bedroom, 2-bathroom condo in the desirable Banyan Bay Club offers an exceptional opportunity to own a spacious, modern / updated, move-in-ready home perfectly positioned in a charming, pet-friendly gulf-to-bay community. This unit combines convenience, amenities, and a relaxed coastal lifestyle—all at an outstanding location. This Banyan Bay condominium has an open floor plan with plank style ceramic tile throughout, recently updated featuring new cabinets, vanities, quartzite/quartz countertops and new stainless steel appliances; new Central Air system, and new hot water heater, in-unit full-size washer & dryer, modern tile design in bath, extra sleeping nook for added flexibility, tastefully furnished (can be sold furnished), private patio nestled under a majestic banyan tree-ideal for morning coffee or evening cocktails, large glass hurricane sliders & windows offering a garden view, fiber optic internet included for each unit. SQUARE FOOTAGE IN SLEEPING NOOK IS ADDED TO MAKE THE INTERIOR SQ FTG 1163. The resort-Style Community Amenities (steps from your door): heated community swimming pool, newly resurfaced tennis and pickleball court, fully equipped fitness center, clubhouse with social hall and full kitchen, new day dock, fishing pier, kayak/paddleboard launch, & storage, private gulf beach access with complimentary lounge chairs on the sand, assigned covered carport parking plus ample guest parking, exterior storage for beach gear, on-site manager and carefree exterior maintenance handled by the association, bicycle storage and mature tropical landscaping with giant banyan trees. Unbeatable Location-why Mid-Key is Best! Everything you need is within walking distance; numerous restaurants & cafes, boutiques, beautiful Durante Park with shaded trails and playground, 3 minute walk to your private Gulf beach, 1-minute walk to the community pool, gym, clubhouse, and courts,. This 44-unit condominium offers a social atmosphere, plenty of activities, up to 2 pets allowed (no weight or size limit). Whether you are seeking a full-time residence, vacation getaway, second home or investment property (valued returning renter’s incomes can offset HOA fees), this immaculate condo is ready for you to move in and start enjoying the island lifestyle today. Don't miss this combination of location, amenities and value on Longboat Key!

5260 Gulf Of Mexico Drive Unit 403, Longboat Key

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

$1,798,000

PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings

2 Beds ⋅ 3 Baths ⋅ R4910478 MLS ⋅ Grand Bay One BLDG.

PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings

3060 Grand Bay Boulevard Unit 174, Longboat Key

Listing courtesy of LEN SCAVRON. 908-304-5454

$1,040,000

Huge $100,000 price adjustment and it’s comes TURN Key furnished. Enjoy the best of Gulf-front living in one of the largest units, this 3-bedroom, 3-bath residence with a flexible study/den/4th bedroom, in a gated community located on the sought-after south end of Longboat Key. This residence offers sweeping views of the Gulf of Mexico and includes an enclosed lanai with new telescopes, hurricane windows, and a spacious interior with tile floors in the main living areas and a neutral color palette. A wall of sliding glass doors in the living room opens to a spacious enclosed terrace—perfect for relaxing, dining, and enjoying the sounds of the surf through the new telescoping hurricane windows. The kitchen is large enough for all the chefs in the family. Corian countertops, a tile backsplash, and a breakfast bar that connects easily to the living space. The primary suite includes a Queen-size bed, wake up to view of the Gulf, access to the terrace/lania, and an en-suite bath with a large walk-in shower. For your guests, the second bedroom has an en-suite bathroom. The third bedroom provides a great space for guests or a home office. The private terrace offers views of the beautifully maintained grounds, the beach, and the Gulf beyond. HVAC unit is a 2021 and comes with a transferable maintenance contract with Home-Tec. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, 4 Har-Tru pickleball courts, a putting green, and a heated saltwater pool and spa. This community also has rental opportunities of monthly rentals 12 times per year. Players Club is located just a short drive to St. Armands Circle, where you will enjoy the shopping and dining experiences. Just over the Ringling Bridge, there are many theater options downtown Sarasota. Additional conveniences include on-site management and a 24-hour staffed gate, ensuring comfort and peace of mind.

3 Beds ⋅ 3 Baths ⋅ A4676606 MLS ⋅ 1425 BLDG.

Huge $100,000 price adjustment and it’s comes TURN Key furnished. Enjoy the best of Gulf-front living in one of the largest units, this 3-bedroom, 3-bath residence with a flexible study/den/4th bedroom, in a gated community located on the sought-after south end of Longboat Key. This residence offers sweeping views of the Gulf of Mexico and includes an enclosed lanai with new telescopes, hurricane windows, and a spacious interior with tile floors in the main living areas and a neutral color palette. A wall of sliding glass doors in the living room opens to a spacious enclosed terrace—perfect for relaxing, dining, and enjoying the sounds of the surf through the new telescoping hurricane windows. The kitchen is large enough for all the chefs in the family. Corian countertops, a tile backsplash, and a breakfast bar that connects easily to the living space. The primary suite includes a Queen-size bed, wake up to view of the Gulf, access to the terrace/lania, and an en-suite bath with a large walk-in shower. For your guests, the second bedroom has an en-suite bathroom. The third bedroom provides a great space for guests or a home office. The private terrace offers views of the beautifully maintained grounds, the beach, and the Gulf beyond. HVAC unit is a 2021 and comes with a transferable maintenance contract with Home-Tec. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, 4 Har-Tru pickleball courts, a putting green, and a heated saltwater pool and spa. This community also has rental opportunities of monthly rentals 12 times per year. Players Club is located just a short drive to St. Armands Circle, where you will enjoy the shopping and dining experiences. Just over the Ringling Bridge, there are many theater options downtown Sarasota. Additional conveniences include on-site management and a 24-hour staffed gate, ensuring comfort and peace of mind.

1425 Gulf Of Mexico Drive Unit 308, Longboat Key

Listing courtesy of KELLER WILLIAMS ON THE WATER S. 941-803-7522

$875,000

Investor Dream Home! A double condo unit which feels like a single-family home and comes with 2 attached oversized garage spaces. Elevated among the treetops on the bay side of Longboat Key, this home features wood floors throughout the first elevated living level, an open great room and kitchen for entertaining. There’s an inviting wood-burning fireplace, screened lanai for bay breezes and a flex room to use as an office, den or guest room. Upstairs you will find 3 bedrooms. Two share a full bath while the primary bedroom features a large ensuite and two walk-in closets. You’ll find stunning views of the bay through a wall of windows and a screened lanai where you can catch the sunset glow over the treetops. Amenities in the premier tennis community include exceptional access to bay waters, perfect for launching a kayak, fishing and enjoying the tide pools. Enjoy a boardwalk stroll through mangroves and watch the sunrise from a private bayside dock (no boat access). Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate. Update, redesign and make it your home or income opportunity today!

3 Beds ⋅ 3 Baths ⋅ A4674750 MLS ⋅ 836 BLDG.

Investor Dream Home! A double condo unit which feels like a single-family home and comes with 2 attached oversized garage spaces. Elevated among the treetops on the bay side of Longboat Key, this home features wood floors throughout the first elevated living level, an open great room and kitchen for entertaining. There’s an inviting wood-burning fireplace, screened lanai for bay breezes and a flex room to use as an office, den or guest room. Upstairs you will find 3 bedrooms. Two share a full bath while the primary bedroom features a large ensuite and two walk-in closets. You’ll find stunning views of the bay through a wall of windows and a screened lanai where you can catch the sunset glow over the treetops. Amenities in the premier tennis community include exceptional access to bay waters, perfect for launching a kayak, fishing and enjoying the tide pools. Enjoy a boardwalk stroll through mangroves and watch the sunrise from a private bayside dock (no boat access). Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate. Update, redesign and make it your home or income opportunity today!

836 Evergreen Way, Longboat Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-383-7591

$2,850,000

Virtually Staged. Under Construction. Under Construction. Pre-Construction | Custom Build | Water to Front & Rear A once-in-a-generation opportunity on one of Longboat Key's most extraordinary streets. Lyons Lane is a truly singular address — a quiet, private enclave in North Longboat Key where homes enjoy an exceptionally rare double-water setting, with sparkling canal frontage to the rear and serene, protected wetland and mangrove views to the front. This is island living at its most private and unspoiled. Design Your Dream Home The vision is still yours to shape. The buyer has the rare opportunity to work directly with the architect to customize the layout, finishes, and features of this brand-new custom home before it's complete. From floor plan adjustments to material selections, this is your chance to create a residence that is uniquely and entirely your own without the years of planning that a true ground-up build typically demands. The property sits on a prime lot with water on both sides; the property includes an existing pool ready to be incorporated into your design, along with a private boat dock and lift with direct access to Millar and Sarasota Bays and no fixed bridges to the Gulf of Mexico. For the boating enthusiast, it simply does not get better than this deep water access, protected dockage, and open water within minutes. Lyons Lane — Longboat's Best-Kept Secret Unlike any other street on the island, Lyons Lane offers homes on one side only, with lush native mangroves lining the opposite side — ensuring that your views, privacy, and natural surroundings will never be compromised. It is one of the few locations on Longboat Key where you can wake up to undisturbed natural beauty in every direction while remaining just moments from the finest dining, boutique shopping, and white-sand Gulf beaches the island has to offer. Longboat Key — Florida's Premier Barrier Island. Stretching 11 miles along Florida's Gulf Coast with over 25 miles of combined waterfront between the Gulf of Mexico and Sarasota Bay, Longboat Key is consistently ranked among the most desirable addresses in the country. The island attracts discerning buyers who demand privacy, natural beauty, and world-class amenities — including the legendary Longboat Key Club, with 45 holes of championship golf, a full-service deep-water marina, spa, and beach club. Opportunities like this — a custom home, double waterfront, dock and lift, and the freedom to personalize are extraordinarily rare on Longboat Key. Don't miss your chance to build exactly the island life you've always envisioned

4 Beds ⋅ 5 Baths ⋅ A4674925 MLS

Virtually Staged. Under Construction. Under Construction. Pre-Construction | Custom Build | Water to Front & Rear A once-in-a-generation opportunity on one of Longboat Key's most extraordinary streets. Lyons Lane is a truly singular address — a quiet, private enclave in North Longboat Key where homes enjoy an exceptionally rare double-water setting, with sparkling canal frontage to the rear and serene, protected wetland and mangrove views to the front. This is island living at its most private and unspoiled. Design Your Dream Home The vision is still yours to shape. The buyer has the rare opportunity to work directly with the architect to customize the layout, finishes, and features of this brand-new custom home before it's complete. From floor plan adjustments to material selections, this is your chance to create a residence that is uniquely and entirely your own without the years of planning that a true ground-up build typically demands. The property sits on a prime lot with water on both sides; the property includes an existing pool ready to be incorporated into your design, along with a private boat dock and lift with direct access to Millar and Sarasota Bays and no fixed bridges to the Gulf of Mexico. For the boating enthusiast, it simply does not get better than this deep water access, protected dockage, and open water within minutes. Lyons Lane — Longboat's Best-Kept Secret Unlike any other street on the island, Lyons Lane offers homes on one side only, with lush native mangroves lining the opposite side — ensuring that your views, privacy, and natural surroundings will never be compromised. It is one of the few locations on Longboat Key where you can wake up to undisturbed natural beauty in every direction while remaining just moments from the finest dining, boutique shopping, and white-sand Gulf beaches the island has to offer. Longboat Key — Florida's Premier Barrier Island. Stretching 11 miles along Florida's Gulf Coast with over 25 miles of combined waterfront between the Gulf of Mexico and Sarasota Bay, Longboat Key is consistently ranked among the most desirable addresses in the country. The island attracts discerning buyers who demand privacy, natural beauty, and world-class amenities — including the legendary Longboat Key Club, with 45 holes of championship golf, a full-service deep-water marina, spa, and beach club. Opportunities like this — a custom home, double waterfront, dock and lift, and the freedom to personalize are extraordinarily rare on Longboat Key. Don't miss your chance to build exactly the island life you've always envisioned

640 Lyons Lane, Longboat Key

Listing courtesy of SEA BREEZE REAL ESTATE LLC. 941-777-7171

$719,000

Experience exceptional beachfront living in this beautiful Gulf-front residence at Arbomar on Longboat Key. Unit 402 is a 2-bedroom, 2-bath condominium offering direct, unobstructed Gulf of Mexico views and immediate beach access, making it the most affordable 2-bedroom, 2-bath opportunity on Longboat Key with true Gulf frontage. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways, updated carports, and new doors and impact-rated windows throughout the community. Inside, the home is move-in ready with a newer AC system and newer appliances, ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. Arbomar offers elevator access, a heated beachfront pool, fitness center, and a welcoming, well-maintained community. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions, and world-class golf—while delivering the rare luxury of direct Gulf views and private beach access at an exceptional value.

2 Beds ⋅ 2 Baths ⋅ A4675789 MLS ⋅ Arbors Apts BLDG.

Experience exceptional beachfront living in this beautiful Gulf-front residence at Arbomar on Longboat Key. Unit 402 is a 2-bedroom, 2-bath condominium offering direct, unobstructed Gulf of Mexico views and immediate beach access, making it the most affordable 2-bedroom, 2-bath opportunity on Longboat Key with true Gulf frontage. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways, updated carports, and new doors and impact-rated windows throughout the community. Inside, the home is move-in ready with a newer AC system and newer appliances, ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. Arbomar offers elevator access, a heated beachfront pool, fitness center, and a welcoming, well-maintained community. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions, and world-class golf—while delivering the rare luxury of direct Gulf views and private beach access at an exceptional value.

4485 Gulf Of Mexico Drive Unit 402, Longboat Key

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

$7,495,000

Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes. Walk in to this fully furnished home which is steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room. The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth. The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub. Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels. Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more. With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.

4 Beds ⋅ 5 Baths ⋅ A4673495 MLS

Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes. Walk in to this fully furnished home which is steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room. The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth. The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub. Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels. Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more. With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.

5005 Gulf Of Mexico Drive Unit 4, Longboat Key

Listing courtesy of DEVELOPERS REALTY LBK, INC. 941-799-9096

$754,900

Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence with a NEW AC (Aug 2026) truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.

3 Beds ⋅ 3 Baths ⋅ A4673695 MLS ⋅ 5 BLDG.

Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence with a NEW AC (Aug 2026) truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.

5270 Gulf Of Mexico Drive Unit 508, Longboat Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-907-9595

$235,000

Great city skyline views and easy access! This 45 x 20 foot slip at Longboat Key Club Moorings is located on the South side of O-dock. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 43 LOA; beam depends on the vessel. Call for more information.

A4674985 MLS

Great city skyline views and easy access! This 45 x 20 foot slip at Longboat Key Club Moorings is located on the South side of O-dock. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 43 LOA; beam depends on the vessel. Call for more information.

2600 Harbourside Drive Unit O-04, Longboat Key

Listing courtesy of LBRE LLC. 941-383-8383

$975,000

Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.

3 Beds ⋅ 3 Baths ⋅ A4674194 MLS ⋅ Players Club BLDG.

Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.

1425 Gulf Of Mexico Drive Unit 408, Longboat Key

Listing courtesy of COLDWELL BANKER REALTY. 941-383-6411

$150,000

WELCOME TO PARADISE! Gulfshore of Longboat Key has it all - private, pristine sand beach, combined with the turquoise waters of the Gulf of Mexico, a marina on Sarasota Bay, large heated community pool, clubhouse with a commercial kitchen, a well-maintained campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armands Circle. This 0.03-acre lot is ready for a new elevated home that will place you only steps to the Gulf of Mexico sand beaches and the marina. There are contractors ready for you to design your floor plan and they will build your home to meet all FEMA standards. The lot also has an outside bath house that is perfect for when you return from the beach. Gulfshore does not permit rentals or pets. This lot, combined with the amenities offered by Gulfshore and the surrounding area, make it the perfect location for you to own a piece of paradise. Please call and schedule your personal showing and review possibilities for your new home in paradise

A4674837 MLS

WELCOME TO PARADISE! Gulfshore of Longboat Key has it all - private, pristine sand beach, combined with the turquoise waters of the Gulf of Mexico, a marina on Sarasota Bay, large heated community pool, clubhouse with a commercial kitchen, a well-maintained campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armands Circle. This 0.03-acre lot is ready for a new elevated home that will place you only steps to the Gulf of Mexico sand beaches and the marina. There are contractors ready for you to design your floor plan and they will build your home to meet all FEMA standards. The lot also has an outside bath house that is perfect for when you return from the beach. Gulfshore does not permit rentals or pets. This lot, combined with the amenities offered by Gulfshore and the surrounding area, make it the perfect location for you to own a piece of paradise. Please call and schedule your personal showing and review possibilities for your new home in paradise

3710 Gulf Of Mexico Drive Unit D11, Longboat Key

Listing courtesy of EDGEWATER REAL ESTATE, INC. 941-778-8104

$2,325,000

Virtually Staged. Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900 square feet, the open-concept layout showcases a chef’s kitchen with an oversized quartz island, premium appliances, and generous counter space ideal for entertaining family and friends. Light-filled second-level living and dining spaces open to an expansive porch and outdoor dining space , creating a seamless indoor-outdoor flow. The first living level features a serene primary suite with a spa-inspired bath and private balcony, offering a peaceful retreat. Upstairs guest suites provide privacy and comfort, with terraces to capture the island’s cooling breezes and glowing Gulf sunsets. A stunning rooftop deck with jacuzzi crowns the home, creating an unforgettable setting for evening relaxation or gatherings under the stars. Additional highlights include impact-rated windows and doors, elevator ready, and a two-car garage with ample storage. The award-winning Conrad Beach community offers a recently renovated resort-style pool with bath facilities and beautifully maintained landscaping, all just a short stroll from the shoreline. Enjoy the vibrant charm of nearby Anna Maria Island, Longbeach Village dining, marinas, and boutique shopping at St. Armands Circle and Sarasota. This home blends coastal sophistication, privacy, and comfort—an ideal winter haven to share with family and friends.

4 Beds ⋅ 5 Baths ⋅ A4672573 MLS

Virtually Staged. Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900 square feet, the open-concept layout showcases a chef’s kitchen with an oversized quartz island, premium appliances, and generous counter space ideal for entertaining family and friends. Light-filled second-level living and dining spaces open to an expansive porch and outdoor dining space , creating a seamless indoor-outdoor flow. The first living level features a serene primary suite with a spa-inspired bath and private balcony, offering a peaceful retreat. Upstairs guest suites provide privacy and comfort, with terraces to capture the island’s cooling breezes and glowing Gulf sunsets. A stunning rooftop deck with jacuzzi crowns the home, creating an unforgettable setting for evening relaxation or gatherings under the stars. Additional highlights include impact-rated windows and doors, elevator ready, and a two-car garage with ample storage. The award-winning Conrad Beach community offers a recently renovated resort-style pool with bath facilities and beautifully maintained landscaping, all just a short stroll from the shoreline. Enjoy the vibrant charm of nearby Anna Maria Island, Longbeach Village dining, marinas, and boutique shopping at St. Armands Circle and Sarasota. This home blends coastal sophistication, privacy, and comfort—an ideal winter haven to share with family and friends.

333 Firehouse Court, Longboat Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-383-7591

$1,250,000

It's all about location. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. This home/land lot is a 1/3-acre with 100 feet of canal frontage on the desired south side of Longboat Key, and so close to the beach is about as good as it gets. The improvement can be inspected for remediation, and the generous lot features a healthy and substantial seawall on a private and quiet street, offering a golden opportunity for a luxury new build. Seller will offer house plans from a reputable LBK coastal builder, Brista Homes (plan buyer expense). The Buttonwood Community has been touted by the Longboat Observer as the neighborliest neighborhood on Longboat Key and is unique for having its safe harbor, boat ramp and boat slips up to 28 feet for its residents. Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. It's all about connectivity. Sarasota SRQ Airport’s soaring success added 20 flights, 20% passenger growth, a new runway and terminal in 2024, ranks No. 1 for the fastest-growing airport in the U.S., and ranks No. 1 best resort airport in the entire country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. Beyond the numbers is the intangible and powerful increase in consumer confidence, which has always proven to enormously influence the housing market, especially luxury and second-home purchases. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide’s list of Top 12 Destinations for 2025. Gov. Ron Desantis announced February 20, 2026, another record-breaking year for tourism in Florida welcomed 143.3 million visitors throughout 2025. An estimated 33.5 million visitors as the highest fourth quarter for visitation on record. According to the release, Florida is the #1 domestic travel destination in the U.S. and a standout choice for international visitors.

A4673355 MLS

It's all about location. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. This home/land lot is a 1/3-acre with 100 feet of canal frontage on the desired south side of Longboat Key, and so close to the beach is about as good as it gets. The improvement can be inspected for remediation, and the generous lot features a healthy and substantial seawall on a private and quiet street, offering a golden opportunity for a luxury new build. Seller will offer house plans from a reputable LBK coastal builder, Brista Homes (plan buyer expense). The Buttonwood Community has been touted by the Longboat Observer as the neighborliest neighborhood on Longboat Key and is unique for having its safe harbor, boat ramp and boat slips up to 28 feet for its residents. Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. It's all about connectivity. Sarasota SRQ Airport’s soaring success added 20 flights, 20% passenger growth, a new runway and terminal in 2024, ranks No. 1 for the fastest-growing airport in the U.S., and ranks No. 1 best resort airport in the entire country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. Beyond the numbers is the intangible and powerful increase in consumer confidence, which has always proven to enormously influence the housing market, especially luxury and second-home purchases. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide’s list of Top 12 Destinations for 2025. Gov. Ron Desantis announced February 20, 2026, another record-breaking year for tourism in Florida welcomed 143.3 million visitors throughout 2025. An estimated 33.5 million visitors as the highest fourth quarter for visitation on record. According to the release, Florida is the #1 domestic travel destination in the U.S. and a standout choice for international visitors.

615 Buttonwood Drive, Longboat Key

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY. 941-383-2500

$595,000

Discover the irresistible charm of historic Longbeach Village and seize a rare opportunity to build your dream island home on Longboat Key. Welcome to the lowest priced vacant single-family parcel available in the Village, an exceptional chance to design a custom residence just off the coast of Sarasota. This desired corner lot in the heart of the village offers flexible design possibilities, including optional rear alley access in addition to two street frontages, giving you potential entry on up to three sides of the property. Positioned within this golf-cart-friendly community, the homesite provides effortless access to everything that makes Longbeach Village so beloved. Enjoy the dazzling white sands and shimmering turquoise waters of the Gulf of Mexico just moments from your door, along with the serene beauty of Sarasota Bay at opposite end of Broadway, both only about a block away. Here, sunrise and sunset become part of your daily routine. Residents of the village enjoy numerous waterfront conveniences, including multiple neighborhood kayak launch points, two fishing piers, a community boat ramp and a variety of dining, shopping and fitness options within minutes of home. With no mandatory HOA, you can store your boat, golf cart, or other island toys beneath a beautiful new elevated home and fully embrace the relaxed coastal lifestyle. This exceptional piece of island real estate invites you to bring your vision to life. Start planning your dream home or private vacation retreat today and experience the unmatched charm of Longbeach Village for yourself.

A4672996 MLS

Discover the irresistible charm of historic Longbeach Village and seize a rare opportunity to build your dream island home on Longboat Key. Welcome to the lowest priced vacant single-family parcel available in the Village, an exceptional chance to design a custom residence just off the coast of Sarasota. This desired corner lot in the heart of the village offers flexible design possibilities, including optional rear alley access in addition to two street frontages, giving you potential entry on up to three sides of the property. Positioned within this golf-cart-friendly community, the homesite provides effortless access to everything that makes Longbeach Village so beloved. Enjoy the dazzling white sands and shimmering turquoise waters of the Gulf of Mexico just moments from your door, along with the serene beauty of Sarasota Bay at opposite end of Broadway, both only about a block away. Here, sunrise and sunset become part of your daily routine. Residents of the village enjoy numerous waterfront conveniences, including multiple neighborhood kayak launch points, two fishing piers, a community boat ramp and a variety of dining, shopping and fitness options within minutes of home. With no mandatory HOA, you can store your boat, golf cart, or other island toys beneath a beautiful new elevated home and fully embrace the relaxed coastal lifestyle. This exceptional piece of island real estate invites you to bring your vision to life. Start planning your dream home or private vacation retreat today and experience the unmatched charm of Longbeach Village for yourself.

641 Broadway Street, Longboat Key

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY. 941-383-2500

$15,550,000

Where the sky opens wide above the Gulf and the shoreline runs uninterrupted, this extraordinary 12,000+ sq. ft. estate stands with a presence that defies comparison. Set on nearly 200 feet of pristine beachfront, the residence is elevated on pilings and wrapped in walls of glass that pull the Gulf’s horizon into every major living space. Inside, soaring cedar ceilings, exposed trusses, and dramatic lines create a sense of volume and warmth that is both refined and inviting. The great room unfolds beneath grand architectural beams and transitions effortlessly to expansive terraces above the sand. A richly crafted lounge with custom bar and billiards area brings a club-like sophistication to the home’s entertainment spaces. The extraordinary chef’s kitchen commands attention with custom inlaid cabinetry, dual oversized islands, professional-grade appliances, and a hidden pantry—ideal for both catered events and everyday living. The second-floor primary suite serves as a private escape with Gulf views, generous sitting area, and a spa-inspired bath. Additional bedroom suites offer privacy for guests, while flexible spaces—including offices, fitness room with sauna, and bonus areas—accommodate a variety of lifestyles. An elevated pool and spa overlook the beach, complemented by multiple decks and outdoor living areas that capture sunrise, sunset, and the sound of the surf. With two elevators, multi-car garage, and exceptional craftsmanship throughout, this is a residence designed for those who seek scale, presence, and true Gulf-front living.

8 Beds ⋅ 10 Baths ⋅ A4671535 MLS

Where the sky opens wide above the Gulf and the shoreline runs uninterrupted, this extraordinary 12,000+ sq. ft. estate stands with a presence that defies comparison. Set on nearly 200 feet of pristine beachfront, the residence is elevated on pilings and wrapped in walls of glass that pull the Gulf’s horizon into every major living space. Inside, soaring cedar ceilings, exposed trusses, and dramatic lines create a sense of volume and warmth that is both refined and inviting. The great room unfolds beneath grand architectural beams and transitions effortlessly to expansive terraces above the sand. A richly crafted lounge with custom bar and billiards area brings a club-like sophistication to the home’s entertainment spaces. The extraordinary chef’s kitchen commands attention with custom inlaid cabinetry, dual oversized islands, professional-grade appliances, and a hidden pantry—ideal for both catered events and everyday living. The second-floor primary suite serves as a private escape with Gulf views, generous sitting area, and a spa-inspired bath. Additional bedroom suites offer privacy for guests, while flexible spaces—including offices, fitness room with sauna, and bonus areas—accommodate a variety of lifestyles. An elevated pool and spa overlook the beach, complemented by multiple decks and outdoor living areas that capture sunrise, sunset, and the sound of the surf. With two elevators, multi-car garage, and exceptional craftsmanship throughout, this is a residence designed for those who seek scale, presence, and true Gulf-front living.

6685 Gulf Of Mexico Drive, Longboat Key

Listing courtesy of COLDWELL BANKER REALTY. 941-383-6411

$995,000

A corner A+ junior suite with a walk-down rarely becomes available. It offers quiet and private golf course views and was completely renovated, with the added benefit of being in the hotel program. A separate bedroom from the living room, with a pullout sofa, offers more flexible sleeping arrangements. The living room and bedroom open directly to your private balcony, with stairs leading to the additional open patio area, which is the advantage of the walk-down. There is also added luxury of in-unit laundry. The primary en-suite bath has double sinks and a full shower, with private access for your guests. There is also plenty of closet space. The resort at Inn on the Beach offers a variety of dining experiences, including a pool, a fitness center, a full-service spa, championship golf, tennis and more. Conveniently on southern Longboat Key, just minutes to St. Armands Circle, with its restaurants and shopping, along with Sarasota and all it offers.

1 Beds ⋅ 1 Baths ⋅ A4672352 MLS ⋅ Na BLDG.

A corner A+ junior suite with a walk-down rarely becomes available. It offers quiet and private golf course views and was completely renovated, with the added benefit of being in the hotel program. A separate bedroom from the living room, with a pullout sofa, offers more flexible sleeping arrangements. The living room and bedroom open directly to your private balcony, with stairs leading to the additional open patio area, which is the advantage of the walk-down. There is also added luxury of in-unit laundry. The primary en-suite bath has double sinks and a full shower, with private access for your guests. There is also plenty of closet space. The resort at Inn on the Beach offers a variety of dining experiences, including a pool, a fitness center, a full-service spa, championship golf, tennis and more. Conveniently on southern Longboat Key, just minutes to St. Armands Circle, with its restaurants and shopping, along with Sarasota and all it offers.

250 Sands Point Road Unit 5101, Longboat Key

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

$769,000

This residence is now available for public and private showings. "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” Restricted access resulted in only three private showings in six months. Buyer's have a rare chance to discover a home that’s been under the radar. (Do not let the days on the market fool you. Snowbirds were unable to view this listing the entire "season"). The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”

2 Beds ⋅ 2 Baths ⋅ A4671822 MLS ⋅ G-Building BLDG.

This residence is now available for public and private showings. "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” Restricted access resulted in only three private showings in six months. Buyer's have a rare chance to discover a home that’s been under the radar. (Do not let the days on the market fool you. Snowbirds were unable to view this listing the entire "season"). The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”

4500 Gulf Of Mexico Drive Unit 206, Longboat Key

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