South Sarasota Real Estate

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Newest Listings in South Sarasota

$224,900

2 Beds ⋅ 2 Baths ⋅ N6145560 MLS ⋅ Gulf Gate Gardens BLDG.

Welcome to Gulf Gate Garden, a desirable condominium community in Sarasota. This well-appointed two-bedroom, two-bathroom end unit condo offers 914 square feet of comfortable living space, featuring a desirable split floor plan and open concept living and dining. The updated kitchen showcases stainless steel appliances, while new tile flooring and an in-unit washer and dryer add convenience. Step outside to the enclosed screened-in deck, an ideal spot to relax and enjoy the Florida lifestyle. Conveniently located just 5.3 miles from the world famous Siesta Key Beach and close to shopping, dining, entertainment, don't miss this opportunity to enjoy comfortable living in the popular Gulf Gate area.

7219 Cloister Drive Unit 202, South Sarasota

Listing courtesy of EXIT KING REALTY. 941-497-6060

$1,650,000

6 Beds ⋅ 5 Baths ⋅ A4704943 MLS

BOATING LIFESTYLE . . . ENTERTAINER'S DREAM HOME . . . WATERFRONT . . . CENTRAL LOCATION . . . PRIVATE DEAD-END STREET . . . Virtually staged with before-and-after photos. Welcome to a one-of-a-kind waterfront home where there truly is a surprise around every corner. Designed for those who love to entertain, boat, gather with family and friends, and enjoy the Florida lifestyle, this spacious pool home offers incredible versatility across three levels with beautiful water views and unforgettable sunsets. The oversized driveway and generous garage space set the tone for a home built to accommodate an active lifestyle. Step inside to soaring ceilings, abundant natural light, and an impressive main living area anchored by a beautiful Coral stone fireplace. Walls of glass sliders draw your eye toward the water and open to a spacious main-level patio—the perfect place for morning coffee, evening cocktails and spectacular Sarasota sunsets. The primary suite is conveniently located on the main living level, complete with its own fireplace, direct patio access, a large walk-in closet with custom built-ins, and a spacious bath with separate his-and-hers vanities. A second bedroom on this level offers wonderful flexibility as a guest room, private office or den. Upstairs, the exceptionally large bedrooms provide plenty of room for family and overnight guests, creating private spaces away from the main entertaining areas. But the fun really begins downstairs. The fully built-out lower level transforms this home into an entertainer’s dream with a bar, game room, additional bedroom or fantastic workout room, full bath that doubles perfectly as a pool bath, and direct walk-in/walk-out access to the pool and patio. Guests can roam from indoors to the pool, fire pit, and waterfront without ever passing through the main living areas. Outside is where this property truly embraces Sarasota living. The fenced yard is ideal for pets, while the waterfront pool and patio create your own private resort. Head down to the dock, where boating water, a composite dock with a 13,000-pound boat lift, and two Jet Ski floating docks make it easy to spend the day exploring the waterways and return home for an evening around the fire pit. With approximately 4,433 square feet of living space, six bedrooms, multiple gathering spaces, and incredible indoor-outdoor flow, this is not a cookie-cutter Florida home. It is a home meant to be experienced—whether hosting a houseful of friends, accommodating extended family, working from home, working out, boating, swimming, or simply watching the sun disappear over the water. This is a fun, unexpected, and wonderfully livable home where every level offers something special and every day feels like vacation. All information provided by the sellers is deemed reliable but is not guaranteed. Buyers are encouraged to verify all information independently.

5544 Dinah Lane, South Sarasota

Listing courtesy of RE/MAX ALLIANCE GROUP. 941-954-5454

$459,000

2 Beds ⋅ 2 Baths ⋅ A4704993 MLS

Welcome to your beachy home at 3141 Regatta Circle! This cozy coastal property perfectly blends peace of mind with luxurious Florida living, boasting an impressive lineup of brand-new, high-ticket upgrades and a spectacular outdoor oasis. Less then 2 miles to Siesta Key Beach and 7.7 miles to Downtown/ Main Street. The Highlights Brand-New Systems (2026): Move in with absolute confidence. This home features a completely new AC/HVAC system, a brand-new hot water heater. This home has had updated piping throughout in the past 10 years, ensuring peak efficiency and years of worry-free living. Sunroom Paradise: Enjoy the gorgeous Florida sunshine year-round in the beautiful all-season sunroom, fully equipped with premium hurricane-impact windows for ultimate safety, climate control, and comfort. this space over looks the the fenced in backyard and pool area Pool & Patio Oasis: Step outside into your private backyard retreat. The pristine pool area features a newly refurbished and re-screened cage (2024) alongside a brand-new pool pump (2024), making it the perfect low-maintenance spot for entertaining or relaxing From the moment you arrive, the pride of ownership is evident. The thoughtful layout maximizes space and natural light, while the seamless transition to the all-season sunroom offers an extended living area perfect for morning coffee or evening relaxation. With all major mechanicals completely updated in 2024/2026, this residence allows you to skip the stress of renovations and start enjoying the coastal lifestyle immediately. This has a very low maintenance yard that is fenced in for peace of mind. This home offers a one car garage with ample storage and a shower! all windows have been replaced with energy efficient, double pane windows, the home has been re-plumbed in the past. This home went through 3 recent major storms with no damage or water intrusion. Don’t miss the chance to own this beautifully updated, storm-ready gem on Regatta Circle. Schedule your private showing today! ***Realtors please see showing restricted times in Realtor comments.

3141 Regatta Circle, South Sarasota

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

$339,000

2 Beds ⋅ 2 Baths ⋅ A4704822 MLS ⋅ 9 BLDG.

Location! Location! Location! Only 3.5 miles to the world-famous sugary sands of Siesta Key Beach. Experience the unique fine quartz sand from the Appalachian Mountains. This tastefully decorated turnkey furnished unit is also safe and secure from the elements. THIS UNIT HAS HURRICANE IMPACT SLIDING GLASS LANAI DOORS, KITCHEN & BEDROOM WINDOWS. Installed in 2018. Unit is on the 2nd floor of a 3-story building with a newly furbished elevator access or stairs. Updated kitchen and bathrooms. Kitchen walls opened, making it bright and cheerful. The entire unit is bright, airy and welcoming. Relax on the screened lanai and let our wildlife entertain you. Ashton Lakes Community is located on 33 acres of luscious greenery, with 4 lakes, a combination of 2 tennis courts and 4 pickleball courts, 2 heated swimming pools, one with lap lane, shuffleboard, clubhouse, grilling stations and other amenities. Close to I-75, rte.41, shopping, restaurants, hospitals and schools. We are also connected to the Merchants Mart by a foot bridge. Shops include CVS, take-outs, ACE hardware, liquor store, beauty salon and the famous Detwiler's Farm market. It's all there for your shopping convenience Make this slice of heaven your paradise in the sun. Disclosures, updates attached. Roof 2014, Air handler 2021. UNIT RENTED FOR FEB & MARCH 2027. Buyer must honor rental lease. Our location is a well-kept secret. Come be a part of this friendly community. Welcome to Ashton Lakes.

5627 Ashton Way Unit 5627, South Sarasota

Listing courtesy of ASHTON LAKES REALTY INC. 941-924-4832

$320,000

3 Beds ⋅ 2 Baths ⋅ A4704874 MLS

Exceptional Investment Opportunity West of the Trail! Rarely available duplex 2/1 + efficiency in the desirable Vamo area offering positive cash flow and excellent income-producing potential. With tenants already in place, this property is an attractive opportunity for investors looking to expand their rental portfolio. Located just minutes from world-famous Siesta Key Beach, shopping, dining, entertainment, and everyday conveniences. No deed restrictions provide additional flexibility and make this property even more appealing as a long-term investment. Property is being sold AS-IS. Don't miss this opportunity to own an income-producing multifamily property in a highly desirable Sarasota location. Please do not disturb tenants. Showings by appointment only.

1854 Debbie Street, South Sarasota

Listing courtesy of RE/MAX ALLIANCE GROUP. 941-954-5454

$320,000

3 Beds ⋅ 2 Baths ⋅ A4704865 MLS

Exceptional Investment Opportunity West of the Trail! Rarely available duplex in the desirable Vamo area offering positive cash flow and excellent income-producing potential. With tenants already in place, this property is an attractive opportunity for investors looking to expand their rental portfolio. Located just minutes from world-famous Siesta Key Beach, shopping, dining, entertainment, and everyday conveniences. No deed restrictions provide additional flexibility and make this property even more appealing as a long-term investment. Property is being sold AS-IS. Don't miss this opportunity to own an income-producing multifamily property in a highly desirable Sarasota location. Please do not disturb tenants. Showings by appointment only.

1854 Debbie Street, South Sarasota

Listing courtesy of RE/MAX ALLIANCE GROUP. 941-954-5454

$594,900

3 Beds ⋅ 3 Baths ⋅ A4704777 MLS

Some houses just have a vibe. This one has it in spades. Tucked away on a quiet dead-end street, this fully updated 3-bedroom, 3-bathroom mid-century modern home blends clean, classic lines with genuine personality — the kind of place that feels curated, not staged. Two of the three bedrooms come with their own ensuite baths, so privacy and convenience are built right in. Step inside and every detail has been thought through: newer appliances, custom closets throughout, and custom blinds that let in just the right amount of Sarasota sunshine. Out back, the good times continue. A permanent screened-in living space is made for long evenings, morning coffee, or watching the rain roll through without missing a beat. The yard is spacious and professionally landscaped, with pet turf that keeps things low-maintenance and always green — no mud, no fuss, just easy living. And then there's the bonus: a separate, private-entrance guest suite. Whether it becomes overflow space for visitors, a long-term income opportunity, or flexible living quarters for extended family, the possibilities are wide open — the layout gives you the freedom to decide what works best. Location seals the deal. This dead-end street offers a rare mix of privacy and convenience, with easy access to everything Sarasota living is known for — shopping, dining, culture, and the Gulf Coast lifestyle just minutes away. Homes that combine this level of updated detail with true flexible living space don't come around often in Sarasota's market. Come see what makes 2121 Palm Terrace special.

2121 Palm Terrace, South Sarasota

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-951-6660

$549,750

4 Beds ⋅ 2 Baths ⋅ TB8544374 MLS

Well maintained Home 4bedroom 2bathrooms 2 car garage. split floor plan, new tile floor throughout main house, new crown molding and baseboards. new garage door opener with camera. Kitchen full remodel wood cabinets with granite countertops with breakfast bar. Large stainless steel Samsung appliances. Laundry room with walk-in shower, when you cut you grass take a shower before going in the house. Wood cabinet Acacia wood shelving, large capacity washer and dryer still has warranty. Master Bath has wood vanity cabinet granite countertop. nice family room for the family to enjoy with sliding door to the big in Lanie. close to all the modern conveniences: beaches, dining, shopping and entertainment.

2161 Inner Cass Circle, South Sarasota

Listing courtesy of ENTERPRISE REALTY SERVICES LLC. 813-965-6587

$1,979,000

3 Beds ⋅ 2 Baths ⋅ A4703427 MLS

Nestled within the desirable West of Trail Southpointe Shores Community, this home benefits from top-rated school zones and a serene, upscale waterfront atmosphere. This canal front home was fully updated with a bright open layout. Three bedrooms, two bathrooms, large updated kitchen with lots of windows and the living areas have pocket sliding doors to outdoor entertaining areas. Luxury vinyl flooring throughout. The indoor/outdoor living quality is almost unbeatable. The current owner added and enlarged the outdoor terrace (almost the width of the entire home) including roofing a section of it and having panoramic and vaulted screening installed that you barely see. Open the pocket sliding doors to create seamless entertaining. Gorgeous views of the canal and great dock space and jet ski lifts also. The canal is very wide and deep water in all tide conditions. The home is only 4 homes away from the intracoastal waterway and just 10 minutes by boat to access the Gulf and Midnight Pass. Roof was replaced in 2021, new pool equipment and air conditioning in 2021. Boat lift 2022. Oversized dock. The neighborhood's private boat ramp, available for a minimal annual fee, enhances its appeal for boating enthusiasts. Perfectly situated close to Sarasota's shopping, dining, Siesta Key beaches, and marinas, the property still offers the tranquility, water access, and elevated coastal living that define a true retreat. Come see it for yourself and bask in the waterfront views from the amazing terrace.

1761 Sandalwood Drive, South Sarasota

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-951-6660

$315,000

2 Beds ⋅ 1 Baths ⋅ A4704625 MLS

Turnkey and beautifully furnished, this Sarasota home is ready to enjoy from day one. Wood-grain tile flooring flows throughout the home, creating a stylish look with the ease of low-maintenance living. The kitchen features a farmhouse sink and breakfast bar that opens to the main living area, while the large dining room/Florida room offers an ideal space for meals, gatherings, or simply relaxing. A custom-tiled shower adds character to the updated bathroom. Outside, the paver patio opens to a private, fully fenced backyard with plenty of space to unwind or entertain. With furnishings included, this home is an excellent choice for a full-time residence, seasonal retreat, first-time buyer, downsizer, or investment property. Conveniently situated to enjoy Sarasota’s shopping, dining, entertainment, and Gulf Coast lifestyle.

3231 New England Street, South Sarasota

Listing courtesy of HARRY ROBBINS ASSOC INC. 941-924-8346

$2,385,000

4 Beds ⋅ 5 Baths ⋅ A4704478 MLS

Welcome to this extraordinary residence, where luxury, comfort, and the ultimate Florida lifestyle come together. Nestled within an intimate community of just five multi-million-dollar homes, this exceptional property offers deeded boating access to Phillippi Creek, leading directly to the beautiful Gulf waters. A private community path leads to the deeded dock with a 10,000-lb boat lift. Even more remarkable, the home sits at approximately 23 feet of elevation and is not located in a flood zone, a rare opportunity to enjoy close proximity to the water with added peace of mind. Barely four years old and showing like new construction, this impressive residence was designed with quality, durability, and energy efficiency in mind. **Sturdy concrete block construction, spray foam insulation, impact-resistant windows and doors, and a metal roof** provide added durability, efficiency, and peace of mind. Inside, soaring 12- to 14-foot ceilings, abundant natural light, and wood-look tile flooring create a bright, elegant, and inviting atmosphere. The spacious open floor plan features four bedrooms plus a dedicated office, three full bathrooms and two half baths, including a convenient pool bath. The office is beautifully appointed with an abundance of custom-built cabinetry, while the oversized laundry room provides even more valuable storage. At the heart of the home is a gourmet kitchen featuring brand-new 2026 Thermador appliances, quartz countertops, abundant cabinetry, LED ceiling lighting, and generous workspace. The kitchen and main living areas flow seamlessly toward the outdoor living space, overlooking the sparkling heated saltwater pool. The expansive lanai is designed for year-round Florida living, complete with a TV and sun shades for added comfort and privacy. Lush tropical landscaping, accent lighting highlighting the beautiful tropical plants, and a collection of fruit trees producing a variety of exotic fruits create a backyard that feels like a private oasis. Indoor and outdoor speakers powered by a Sonos system make the space equally suited for peaceful evenings or entertaining family and friends. The oversized garage offers nearly 1,000 square feet of space and has been fully repainted, upgraded with epoxy flooring, and equipped with its own split A/C system. The home also features three separate interior A/C zones for enhanced comfort and energy efficiency. Located near highly rated A-rated schools and just a short drive from Sarasota's beautiful Gulf beaches, this home combines an exceptional location with boating access, impressive elevation, quality construction, and an extensive list of thoughtful upgrades. From the custom cabinetry and abundant storage to the resort-style outdoor living spaces, every detail contributes to the home's unique and luxurious character. **This is a truly special opportunity. Schedule your private showing today and experience this remarkable home for yourself.** Video link attached.

2462 Missara Lane, South Sarasota

Listing courtesy of DALTON WADE INC. 888-668-8283

$240,000

2 Beds ⋅ 2 Baths ⋅ A4704481 MLS ⋅ Na BLDG.

A little Sarasota gem you didn't know existed. Quiet and secluded Crooked Creek is hidden near Red Bug Slough Preserve where you have a private gated entrance to the park. A laid-back community with a newer roof & carport, heated pool, gazebo, poolside kitchen, gas and charcoal grills, tennis and pickleball court, and community storage with private lockers. This adorable dog friendly 2 bedroom 2 bath condo is positioned perfectly on the first floor and near the pool with an unobstructed view of Crooked Creek. With 1,027 sf of living space, there is room to accommodate a dedicated home office space and entertaining guests comfortably. The kitchen is large with a pantry, bar seating and a garden window. The primary bedroom has windows facing the creek, a walk-in closet and a second built-in closet, and an en-suite bathroom that also hosts the washer and dryer. A spacious and versatile second bedroom is ready to suit your needs and is adjacent to the guest bath. Embrace the Sarasota lifestyle and enjoy dog friendly Red Bug Slough with over 3 miles of combined unpaved and accessible nature paths. Minutes to Siesta Key & Turtle Beach, Gulf Gate, The Legacy Trail, shopping and dining.

3365 Cross Creek Dr Unit 3365, South Sarasota

Listing courtesy of WIEGAND REALTY. 941-232-0946

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