South Sarasota Real Estate

South Sarasota Real Estate

Welcome to South Sarasota, a vibrant city nestled in the heart of Sarasota County, Florida. Known for its stunning beaches, rich cultural heritage, and thriving real estate market, South Sarasota offers an exceptional quality of life for residents and visitors alike.

Located in the southwestern part of the Sunshine State, South Sarasota benefits from Florida's year-round warm climate, making it a haven for outdoor enthusiasts. With its pristine white sandy beaches and crystal-clear turquoise waters, residents can enjoy a variety of water activities such as swimming, sunbathing, boating, and fishing.

In addition to its natural beauty, South Sarasota boasts a diverse range of cultural attractions. The city is home to several art galleries, theaters, and museums, offering a wealth of cultural experiences. The vibrant arts scene is complemented by a thriving culinary scene, with an abundance of restaurants, cafes, and bistros serving up delicious cuisine from around the world.

South Sarasota also offers a wide range of real estate options to suit every lifestyle and budget. From luxurious waterfront properties with breathtaking views to cozy single-family homes in family-friendly neighborhoods, there is something for everyone. The city's real estate market is known for its stability and growth, making it an attractive destination for both homeowners and investors.

With its idyllic location, rich cultural heritage, and thriving real estate market, South Sarasota is truly a gem on Florida's Gulf Coast. Whether you're looking to settle down or invest in property, South Sarasota has it all.

Newest Listings in South Sarasota

4 Beds ⋅ 8 Baths ⋅ A4703378 MLS

Some properties offer a view. This extraordinary 1.41 acre Oyster Bay estate offers an entire waterfront world of its own and is one of the best waterfront locations that Sarasota has to offer, with more than 430 feet along Sarasota Bay and a setting that feels virtually irreplaceable. Spanish and Mediterranean inspired architecture lends warmth, character, and timeless sophistication to this remarkable six bedroom residence, while its expansive shoreline creates a front row seat to spectacular sunsets, passing boats, and the natural beauty of Sarasota’s coastal landscape. With access to the Intracoastal Waterway and Gulf of Mexico, this is a rare opportunity for the luxury buyer who believes life is best lived on the water. Spanning more than 10,000 total square feet, with nearly all principal living areas on one level, the home was created for both grand entertaining and relaxed waterfront living. Dramatic ceilings, distinctive architectural details, expansive windows, and a spectacular gallery space with an interior fountain establish a sense of occasion, while multiple intimate gathering areas make the estate equally comfortable for everyday life. A commercial grade chef’s kitchen with professional appliances is equipped for effortless entertaining, from elegant dinners to large celebrations. The primary suite is a private sanctuary framed by beautiful bay views, featuring an expansive custom wardrobe and an indulgent bath with soaking tub, oversized shower, and dedicated massage and sauna room. Five additional bedroom suites provide exceptional privacy for family and guests, each with its own bath and generous storage. Beyond the interiors, the estate unfolds like a private resort. A swimming pool, tennis court, fitness room, billiard room, private office, three car garage, abundant storage, and permitted dock replacement create a property designed for recreation, relaxation, and life on the water. A new roof completed in 2024 adds further value and peace of mind. The address is equally exceptional. Oyster Bay Estates places you near The Field Club, Siesta Key, Southside Village, Sarasota Memorial Hospital, and Downtown Sarasota, offering remarkable access to world class beaches, boating, fine dining, shopping, arts, and culture while remaining tucked within a prestigious waterfront enclave. For those with an even greater vision, the magnificent acreage and extraordinary bay frontage also present the opportunity to create a completely new custom waterfront estate. The property may offer potential for division into two buildable homesites if the existing residence is removed, subject to verification and applicable approvals. With its commanding Sarasota Bay frontage, boating access, acreage, privacy, and coveted location, 1136 N Lake Shore Drive is not simply a place to live. It is the opportunity to claim an extraordinary piece of Sarasota’s waterfront lifestyle.

1136 N Lake Shore Drive, South Sarasota

3 Beds ⋅ 2 Baths ⋅ A4703229 MLS

Welcome to 2702 Grand Cayman Street, a charming and well-maintained starter home ideally located in Sarasota between the convenience of downtown and the beaches of Siesta Key. This move-in ready 3-bedroom, 2-bathroom residence offers a comfortable layout with generous bedroom sizes, custom blinds, and plenty of closet space. The kitchen features granite countertops, stainless steel appliances, and a unique built-in coffee system. What truly sets this home apart is the significant investment made in its core structural components, offering a buyer true long-term security. A brand-new roof was installed just weeks ago, providing an immediate advantage when securing home insurance alongside total peace of mind. The home is also equipped with a fully programmed alarm system covering all doors and windows. Situated in a great school district close to Phillippi Shores Elementary and Riverview High, this property is equally suited as a welcoming primary residence or a investment opportunity.

2702 Grand Cayman Street, South Sarasota

2 Beds ⋅ 2 Baths ⋅ A4701100 MLS

Don't miss the opportunity to see this fantastic, centrally located 2/2/1 residential home in the much sought after Gulf Gate neighborhood. The property consists of a lush, large corner lot with a side fenced area and an irrigation system. Located just minutes from World Famous Siesta Key Beach and the Gulf Gate shopping district. This Ruth Richmond designed split plan home was remodeled in the 90's and has a cool, retro vibe. Beautiful Terrazzo floors thru-out the main living areas and carpet in the bedrooms. Spacious main bedroom has a walk-in closet and a large bay window. The main, attached bath has his & her sinks and a walk-in shower. The light & bright central kitchen has a breakfast bar, Corian countertops & plenty of cabinet space. Gulf Gate is a deed restricted neighborhood just down the street from the new Sarasota Square project. New flat roof installed last year. This represents the lowest priced single family home in the neighborhood . Become part of a friendly, family-focused community in one of Sarasota’s most desirable areas. Location truly matters—and Gulf Gate delivers! Tenant occupied until March 31, 2027.

3190 Regatta Circle, South Sarasota

2 Beds ⋅ 1 Baths ⋅ A4703297 MLS

AFFORDABLE SARASOTA LIVING JUST MINUTES FROM SIESTA KEY! Opportunities like this are hard to find! Located in desirable South Winds Mobile Home Park, this well-maintained home offers an incredibly affordable lifestyle with monthly fees of only $195. Enjoy the best of Sarasota living in this friendly 55+ community, just minutes from world-renowned Siesta Key Beach! This home has been lovingly maintained and is ready for immediate occupancy. The comfortable interior features an open living and dining area along with a nicely arranged kitchen. Even better, the outdoor living space is exceptional! A newer carport and screened lanai have been added (2 nice sized lanai's ... 1 on each side!) providing additional space to relax and enjoy the Florida lifestyle. This area also includes a convenient storage room for a washer and dryer. On the opposite side is an additional covered lanai, giving you even more space for outdoor living, entertaining, or simply enjoying our beautiful Florida weather. Important improvements include an air-conditioning system installed in 2020 and re-piping completed in 2022. A termite warranty/contract will also transfer to the new owner at closing. Tucked toward the back of the community on one of its quieter streets with minimal through traffic, this home offers a peaceful setting while keeping you remarkably close to everything in Sarasota. South Winds offers a beautiful, heated community pool, shuffleboard, horseshoes, pickleball, a putting green, library, recreation hall, social activities, friendly neighbors and superb on-site management! Hop on your bike or scooter and head towards Siesta Key, or take a quick drive and have your toes in the sand in approximately five minutes! Cultural downtown Sarasota is approximately 15 minutes away, offering outstanding restaurants, shopping, theaters, opera, galleries and entertainment. Affordable fees, a fantastic location and the Siesta Key lifestyle - this one is a gem! Furniture is negotiable. Being sold As-Is with Right to Inspect. Don't miss this rare opportunity to own in one of Sarasota's affordable 55+ co-op communities but don't wait ... this one won't last long. H-U-R-R-Y!

251 Southwinds Drive, South Sarasota

2 Beds ⋅ 2 Baths ⋅ A4702878 MLS ⋅ 5785 BLDG.

Virtually Staged. Welcome to this beautifully updated 2 bedroom, 2 bathroom condo offering a refined blend of comfort, style, and effortless Florida living. Thoughtfully updated throughout, this light-filled residence features LVP flooring throughout the main living areas, inviting indoor and outdoor living spaces, a welcoming front porch, and a private rear porch, along with access to a beautifully maintained community pool. The updated kitchen combines modern style with warm, natural accents, featuring crisp white cabinetry, stainless steel appliances, and custom Acacia wood butcher-block countertops sealed with a water-based polyurethane finish. A sliding glass door off the kitchen opens directly to the private front porch. The spacious primary suite provides a peaceful retreat with a generously sized walk in closet featuring built-in shelving for exceptional storage and organization. The beautifully updated en-suite bathroom continues the home's custom finishes with an Acacia wood butcher-block vanity countertop, also sealed with a water-based polyurethane finish, complemented by a stylish vessel sink and matte-black faucet. A glass-enclosed walk-in shower finished with wood look tile completes this inviting, spa-inspired space. The second bedroom offers excellent flexibility for guests, a home office, or a hobby room and is conveniently served by a full guest bathroom featuring a tub and shower combination with tasteful tile accents. For added everyday convenience, the home includes a full size stacked washer and dryer along with additional shelving, making laundry and storage effortless. Outdoor living is just as inviting, with both a welcoming front porch and private rear porch providing comfortable spaces to enjoy morning coffee, outdoor dining, grilling, or relaxing in the Florida breeze. Residents also enjoy access to a sparkling community pool surrounded by lush landscaping, mature shade trees, and ample lounge seating, creating a peaceful retreat just steps from home. Ideally positioned near Siesta Key, this residence puts some of Sarasota's most desirable beaches, restaurants, shopping, and local attractions within easy reach. Whether you're looking for a full-time residence, seasonal retreat, or low maintenance investment, this beautifully updated condo offers the ideal blend of thoughtful upgrades, private outdoor living, community amenities, and an unbeatable Sarasota location.

5785 Summer Side Lane Unit 4A, South Sarasota

3 Beds ⋅ 2 Baths ⋅ A4703111 MLS

Rarely available 1965 Sarasota School of Architecture home designed by James Padgett, offering a masterclass in mid-century design in the heart of Gulf Gate. Floor-to-ceiling windows in the primary suite, kitchen, and dining area flood the home with natural light, while soaring pine ceilings extend through the kitchen, dining, and living spaces for a warm, architectural feel rarely found at this price point. Recently updated with a brand new roof, fresh interior and exterior paint, and new landscaping this home is truly move-in ready. Ideal for the buyer who loves indoor/outdoor living, the home sits minutes from Siesta Key Beach with easy access to downtown Sarasota and Venice. Located in Gulf Gate, walking distance to Gulf Gate Elementary (also a local hurricane shelter), and close to the future Whole Foods–anchored redevelopment of the former Sarasota Square Mall site bringing new retail, dining, and residential growth to the area. A rare chance to own an architecturally significant home in one of Sarasota's most connected neighborhoods.

6332 Pauline Avenue, South Sarasota

One property. Multiple possibilities. This cleared 15,080-square-foot corner property in Orange Crest Park offers the flexibility to create one custom dream residence on an expansive homesite or explore its potential for two-home development. Currently held under one tax parcel, the property comprises two originally platted lots, with a new survey in process. Sarasota County has indicated the lots may be restored to their original configuration, with potential for one single-family residence per lot. An accessory dwelling unit may also be permitted with a primary residence, subject to County requirements. A County-approved variance provides additional design flexibility, subject to its terms and review of proposed plans. Phillippi Shores Elementary is just around the corner, while downtown Sarasota, Southside Village, shopping, dining, cultural attractions and Siesta Key Beach are only a short drive away. Whether your vision includes a custom residence, multigenerational living or new-home development, this property offers a rare combination of location, land and versatility. Buyer and Buyer’s Agent are responsible for independently verifying all information contained in this listing. All information is deemed reliable but is not guaranteed.

2110 Sandrala Drive, South Sarasota

2 Beds ⋅ 2 Baths ⋅ A4702996 MLS

BUYER INCENTIVE – RECEIVE A 1% LENDER CREDIT WITH PREFERRED LENDER! BRAND NEW ROOF WITH TRANSFERABLE WARRANTY + BRAND NEW A/C! Welcome home to this well-maintained villa located in a 55+ Sarasota community with plenty of amenities to enjoy. Inside, you'll find a bright and comfortable layout with 2 bedrooms, 2 bathrooms, spacious living and dining areas, and a functional kitchen with plenty of cabinet and counter space. The big-ticket items have already been taken care of with a brand new roof, transferable roof warranty, and brand new A/C, giving the next owner added peace of mind. Enjoy an active Florida lifestyle with community amenities including a heated pool, fitness center, shuffleboard, clubhouse, library, billiards, gathering spaces, and an on-site marina with boat docks. Conveniently located near shopping, dining, beaches, and everything Sarasota has to offer. Come see why this home and community are such a great place to call home!

2407 Riverbluff Parkway Unit V-226, South Sarasota

2 Beds ⋅ 2 Baths ⋅ A4702960 MLS ⋅ 3427 BLDG.

Tour 1 Come see this very modern, updated 2-bedroom, 2-bath condo in Sienna Park, ideally located in the heart of Sarasota! This move-in-ready unit features an updated kitchen with granite countertops, updated bathrooms, attractive vinyl flooring, and a bright, comfortable living space. This ground floor unit has a very favorable front door, designated parking space. Also, a private fenced in back yard is included!! Sienna Park offers great community amenities, including a heated swimming pool, fitness center, clubhouse, tennis courts, and recreational areas. The central location puts you close to shopping, restaurants, grocery stores, entertainment, and everyday conveniences, with world-famous Siesta Key Beach just a short drive away. This unit has maintained great rental history for the investor.

3427 Clark Rd Unit 127, South Sarasota

2 Beds ⋅ 2 Baths ⋅ O6433310 MLS

Welcome to this bright and inviting 2-bedroom, 2-bath Sarasota home offering 1,395 square feet of living space and a desirable split-bedroom floor plan. The interior features laminate flooring throughout and an updated kitchen with quartz countertops, decorative backsplash, and ample cabinetry. There is an inside laundry room and a separate living room that provides additional flexible living space, while the Florida room offers another versatile area for enjoying the Florida lifestyle. The spacious layout and abundant natural light create a comfortable atmosphere throughout the home. Conveniently located near downtown Sarasota, area dining, shopping, cultural attractions, and the beautiful Gulf beaches, this property offers an excellent opportunity to enjoy all that Sarasota has to offer. Bring your personal touches to make this home your own! All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyer advised to verify.

1840 Glengary Street, South Sarasota

2 Beds ⋅ 2 Baths ⋅ A4702358 MLS ⋅ V-315 BLDG.

Welcome to Strathmore Riverside Villas, an active 55+ community in Sarasota where maintenance-free living meets a true boater's amenity package just minutes from Siesta Key. This move-in ready villa offers two bedrooms, two bathrooms, a flex room that works beautifully as a den, study, or office, and an enclosed lanai Florida room, giving you an abundance of flexible living arrangements all on one level. The foyer opens to the main living areas, where luxury vinyl flooring, plantation shutters, and natural light set a clean coastal tone. The spacious and open living and dining space continues into the Florida room, overlooking the green space behind the home, an inviting spot for morning coffee, reading, or casual entertaining. The updated kitchen features recycled glass countertops, a glass mosaic tile backsplash, white cabinetry, stainless appliances, recessed lighting, and pantry storage. The primary suite includes a walk-in closet and an ensuite bath with a walk-in shower, and a guest bedroom and full bath sit at the front of the home. The covered carport delivers everyday convenience, with a dedicated laundry room featuring a utility sink and shelving that doubles as extra storage for beach gear, bikes, and tools. The community's waterfront setting is what sets it apart. A resident marina offers boat slips on a first-come basis for a nominal fee, with access out to the Intracoastal Waterway and the Gulf beyond, so you can keep your boat steps from home. The waterfront clubhouse anchors a full social calendar and includes a large gathering hall, fitness room, library, and a game room with billiards, shuffleboard, and ping pong, all beside a heated pool and sun deck overlooking the water, with outdoor shuffleboard courts nearby. Grounds maintenance is handled for you, leaving more time to enjoy it all. From here you are about four miles from the sands of Siesta Key Beach, minutes from the shops and restaurants of Gulf Gate, and a short drive to downtown Sarasota's dining, arts, and bayfront. Come experience the villa and the lifestyle that comes with it. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

2327 Waterbluff Place Unit V315, South Sarasota

3 Beds ⋅ 2 Baths ⋅ A4702845 MLS

Beautiful!! Completely rehabbed with nice finishes throughout,New Ac and much more , this move-in-ready home offers modern updates, quality craftsmanship, and a bright, welcoming interior. Ideally located near top Sarasota schools, shopping, and dining, and just minutes from Siesta Key Beach, this property delivers both comfort and convenience in one of Sarasota’s most desirable areas. The neighborhood features new construction homes selling at significantly higher prices, making this an exceptional value. Enjoy a spacious, fully fenced patio—including the front yard—for absolute privacy, with plenty of room for an RV, multiple vehicles, or a boat. Schedule your showing today and explore the possibilities for yourself.

2839 Olympic Street, South Sarasota

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