South Sarasota Homes with Sidewalks Community Features

South Sarasota Homes with Sidewalks Community Features

Welcome to South Sarasota, a hidden gem nestled in the heart of Florida's picturesque Sarasota County. This vibrant community is renowned for its lush landscapes, friendly atmosphere, and an enviable lifestyle that perfectly blends relaxation with recreation. Here, residents enjoy the best of both worlds—proximity to the stunning Gulf Coast beaches and a thriving local culture that includes art galleries, boutique shopping, and delectable dining options.

One of the standout features of South Sarasota is its inviting homes with sidewalks, fostering a sense of community and encouraging outdoor activity. Imagine leisurely strolls through tree-lined streets, where neighbors greet each other with warm smiles and children play safely in front yards. Sidewalks not only enhance the neighborhood's charm but also promote a healthy, active lifestyle, making it easy for families to enjoy evening walks or morning jogs.

In South Sarasota, you'll find a diverse range of homes that cater to various tastes and budgets, from cozy bungalows to spacious family residences. Many properties are designed with outdoor living in mind, featuring beautiful gardens and patios perfect for entertaining or simply unwinding after a long day.

With its strong sense of community, excellent schools, and abundant parks, South Sarasota is an ideal place for families, retirees, and anyone seeking a serene yet vibrant lifestyle. Whether you’re looking to buy your first home or searching for a peaceful retreat, South Sarasota welcomes you with open arms and endless possibilities. Come discover the charm of this delightful community, where every day feels like a vacation!

Newest South Sarasota Homes with Sidewalks Community Features

2610 Regatta Drive, Sarasota
$394,900
2 Beds ⋅ 2 Baths ⋅ Gulf Gate SubDv. ⋅ 34231 Zip Code
Virtually Staged. Welcome to the lowest priced home in Gulf Gate! It has been extremely well maintained with good bones! Many improvements, including: Interior & Exterior Freshly Painted 2026*Guest Bathroom completely remodeled 2026*Washer & Dryer 2025*Lanai Re-screened 2024*Shingle Roof 2023*Air Conditioner (Rudd Package 14 Seer, 7 KW) 2022*Water Heater 2022*Ten (10) Impact Resistant Energy Efficient Windows and Doors 2018*Soffits and Fascia 2018*Bosch Dishwasher 2017* Refrigerator & Range 2017*Hurricane Garage Door and Opener 2016*Plumbing redone overhead & much more! Excellent Curb Appeal with attractive landscaping and a convenient circular driveway for easy in and out! This is a dead-end street with very little traffic and just a community of good neighbors. Enforced deed restrictions keep the community nice and Gulf Gate is lined with sidewalks for walkers & runners! Split Plan, Beautiful Plantation Shutters throughout, a spacious Florida Room plus a Huge Lanai for entertaining and relaxation! Outside Patio and a Fenced Area for pets to roam. This home is within minutes to World Renowned Siesta Key Beaches, Legacy Trail, several fitness centers, Gulf Gate Shops & Restaurants, Gulf Gate Library and A+ Schools. Within 15-20 minutes to cultural downtown Sarasota which offers fine dining, opera, Selby Gardens, boutique shopping, movie theaters and much more. This is a properly priced home and it is ready for you to move right in! All the major ticket items have been done, so add your personal touches and either have the terrazzo floors professional buffed and finished or add your own flooring to make this home sparkle. This one is a beauty and the location couldn’t be better! Enjoy the Gulf Gate shopping/dining, library & more! Make it yours but don’t wait … this one simply won’t last. H-U-R-R-Y while you can!

2610 Regatta Drive, Sarasota
1640 Stickney Point Road Unit 40-101, Sarasota
$319,000
2 Beds ⋅ 2 Baths ⋅ Castel Del Mare SubDv. ⋅ 34231 Zip Code
Say Hello to a Great Buy! You simply can’t beat this location! This freshly updated, fully furnished 2-bedroom, 2-bath ground-floor condo is located West of the Trail in the highly sought-after waterfront community of Castel Del Mare, just minutes from world-famous Siesta Key. Step inside and discover an inviting, move-in-ready residence featuring Corian countertops, stainless steel appliances, tasteful furnishings, a designer fireplace, and HD Smart TVs in both bedrooms and the main living area. The A/C system and water heater were replaced in 2022, while the separate laundry room offers a full-size washer and dryer plus additional storage. Best of all, ground-floor living means no stairs and easy access! Castel Del Mare offers a true resort-style Florida lifestyle with two sparkling swimming pools—including one overlooking the Intracoastal Waterway—tennis and pickleball courts, kayak launches, fishing piers, community grills, assigned parking, and on-site management. And the location is hard to beat! Siesta Key and its beautiful beaches are just minutes away, while the nearby Southbridge area puts restaurants, shopping, entertainment, and bike and boat rentals practically at your doorstep. With one-month minimum rentals permitted, this property offers excellent flexibility for a full-time residence, seasonal getaway, or investment opportunity. Fully furnished, meticulously maintained, and priced to sell—this is your opportunity to own a little piece of paradise. Welcome home to YOUR Castle by the Sea!

1640 Stickney Point Road Unit 40-101, Sarasota
3458 Wilkinson Woods Drive Unit 2, Sarasota
$335,000
2 Beds ⋅ 2 Baths ⋅ Wilkinson Woods SubDv. ⋅ 34231 Zip Code
UPDATED THROUGHOUT, NEWER FLOORING, WATER HEATER, LED DIMMABLE LIGHTING, SOFT CLOSE CABINETRY, TILE, JETTED SPA TUB, OVERSIZED WALK IN SHOWER, GRANITE SINKS, HIGH END FAUCETS, LADIES VANITY, WALK IN CLOSETS, MURPHY BED, TWO FULL UPDATED BATHROOMS, LARGE ENCLOSED LINAI, PRIVATE PATIO, NEWER WATER HEATER, WASHER AND DRYER, UTILITY SINK, HUGE DRIVEWAY, 2 CAR GARAGE. HEATED SWIMMING POOL, CLUBHOUSE & TENNIS JUST STEPS AWAY. EXTERIOR MAINTENANCE, INSURANCE, INTERNET AND CABLE INCLUDED. CALL FOR A SHOWING TODAY

3458 Wilkinson Woods Drive Unit 2, Sarasota
1636 Stickney Point Road Unit 201, Sarasota
$315,000
2 Beds ⋅ 2 Baths ⋅ Castel Del Mare SubDv. ⋅ 34231 Zip Code
Welcome to This Move In (and Rent Ready) Condo in the Highly Desirable Castel Del Mare Condo Community in Siesta Key ! This Bayfront Neighborhood is ideally Situated at the Gateway to the "Hidden Jewel of the Bay" & Offers an Unmatched Combination of Convenience & Lifestyle Amenities for the Value. Step Inside to Neutral Decor & an open Floor Plan ! Many Furnishings Negotiable ! Solid Surface Flooring Throughout. The Updated Kitchen Features Plenty of Cabinetry, Granite Counters, Pantry, & Eat In Breakfast Bar Accompanied by a Dining Area. The Spacious Great Room Offers Plenty of Space to Entertain & Has Access to the Covered Lanai. Down the Hall are the Bedrooms Including the Primary Suite Which Includes an En Suite Bath, Large Walk in Closet, & Private Access to the Lanai. The Laundry & More Storage Area Can Also be Found Outside. Newer HVAC ! This Resort Style Complex Makes for the Complete Lifestyle Experience with Two Pools (One Overlooking the Intercoastal), Tennis/Pickleball Courts, Shuffleboard, Kayak Racks, Boardwalk & Bayside Gazebo, & a Fishing Pier All Set Up Amongst a Gorgeous Waterfront. Located Just Steps From Shopping, Fine Dining, & Everything You Need - Including the Beach ! Whether for a Full Time Residence, Seasonal Escape, or an Investment Opportunity - This Affordable Condominium in a Fantastic Location is a Must See for Your Dream Sarasota Living !

1636 Stickney Point Road Unit 201, Sarasota
1515 Clower Creek Drive Unit HA158, Sarasota
$395,000
3 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
Welcome to the award-winning waterfront community of Pelican Cove, where lush tropical grounds, an incredible array of amenities, activities, and social clubs create a truly exceptional Sarasota lifestyle. This GROUND-FLOOR WATERFRONT CONDO enjoys a prime location overlooking the entrance to beautiful Clower Creek. The light and bright END-UNIT features additional windows for added light, neutral tile flooring, updated bathrooms, a newer electrical panel, upgraded raised-panel doors throughout, modern paint colors, and a new A/C system. Step outside from the sliding glass-enclosed lanai to the oversized waterfront Trex-type deck and relax while enjoying abundant wildlife, tropical surroundings, and boats as they cruise into the canal. Offered turnkey furnished, this inviting condo is move-in ready and provides the perfect opportunity to enjoy the Pelican Cove lifestyle from day one. PELICAN COVE FEATURES includes over 28+ organized clubs including art & sculpture, active yacht club, folk music, photography & cinema clubs, social clubs, and many more. There is a for-fun “Pelican Cove University” covering several diverse subjects like politics, history, financial topics, and much more. The community has a woodworking studio, pottery studio, many card-playing clubs, water exercise & yoga, and a tennis club. There are several yearly jazz and cultural concerts and a few harborside concerts as well. Pelican Cove has a 24-hour gated and staffed entrance, 87-slip boat harbor with over 130 kayak/canoe storage racks & launch docks, fishing docks, three very active clubhouses, large exercise room, six heated pools, hot tub, basketball, dog exercise area, 5.5 miles of meandering boardwalks & nature trails, two lighted tennis courts and six lighted pickleball courts all in an award-winning community with unbelievably well-manicured tropical grounds! Welcome to Pelican Cove!

1515 Clower Creek Drive Unit HA158, Sarasota
7143 Wood Creek Drive Unit 203, Sarasota
$229,900
2 Beds ⋅ 2 Baths ⋅ Woodside Terrace SubDv. ⋅ 34231 Zip Code
Just 8 minutes from SIESTA KEY this 2/2 condo Is fully FURNISHED in a modern/coastal decor. It has an open floor plan featuring stainless appliances, granite counters, 2 renovated baths, & inside laundry rm. There's a screened lanai, w/ new 2005 hurricane shield protecting both sliders. A large storage area and carport at your doorstep. Low maint fees ( $ 603) include INTERNET, ROOF REPLACEMENT, ext maint, HEATED POOL, ext insurance, pest control, management, TRASH, landscaping etc. The remodeled clubhouse has a grill, full kitchen W/WINE BAR, internet, lg TV, darts, & a library. There's always fun social events ( poolside TIKI BAR ) in this 55+, well maintained community. There are brand new Roofs on this 2story, carports & clubhouse ( 9/15/26 ) The complex & unit did not experience any water damage during the last hurricanes. Located just a few blocks from the fun & funky VILLAGE of GULF GATE . EASY TO VIEW!

7143 Wood Creek Drive Unit 203, Sarasota
2510 Bispham Road, Sarasota
$399,900
2 Beds ⋅ 2 Baths ⋅ Gulf Gate SubDv. ⋅ 34231 Zip Code
There's a lot to love about this charming Gulf Gate residence- the location, the well-appointed interior, and the oversized impeccably landscaped lot all come together to create a package that offers great value! This two bedroom home offers a spacious split floor plan with nice interior updates including luxury vinyl flooring throughout, can lighting, updated kitchen with stainless steel appliances and butcher block countertops, updated bathrooms and much more. There is an extended, pavered, covered lanai for enjoying the Florida outdoor lifestyle. The landscaped front and backyards round out this amazing offering. The shingle roof was replaced in 2017. The Gulf Gate location is really what its all about- just a short drive to Siesta Key Beach, easy access to retail, shopping and night life- this location has it all. Don't wait- schedule your private showing today!

2510 Bispham Road, Sarasota
1720 Glenhouse Drive Unit 328, Sarasota
$319,900
2 Beds ⋅ 2 Baths ⋅ Pelican Cove SubDv. ⋅ 34231 Zip Code
COMPLETELY RENOVATED AND MOVE-IN READY IN PELICAN COVE! Almost everything inside this spacious 2-bedroom, 2-bath condo has been updated, giving you the opportunity to move in and immediately start enjoying one of Sarasota's most unique gated waterfront communities. Step inside to a bright, open living and dining area featuring new flooring throughout, fresh interior paint, new lighting and ceiling fans and a beautifully renovated kitchen overlooking the main living space. The kitchen features new quartz countertops, cabinetry, stainless steel appliances, subway-tile backsplash and updated fixtures. Both bathrooms have been beautifully updated with new vanities, countertops, fixtures and finishes, including a newly tiled tub/shower surround. The bedrooms feature the same new flooring and fresh, neutral finishes found throughout the home. The closets have also been upgraded with new shelving, providing plenty of useful storage. Enjoy the large screened lanai, surrounded by Pelican Cove's lush tropical landscaping, with the added convenience of an in-unit washer and dryer located just off the lanai. Another feature you'll appreciate every day is the covered parking located right by the unit — no long walk from your car to your condo. And then there's Pelican Cove. This gated, approximately 75-acre waterfront community offers a lifestyle that's difficult to duplicate in Sarasota, with a private harbor and boat slips, direct access to the Intracoastal Waterway, kayak/canoe/paddleboard facilities, fishing areas, multiple heated swimming pools, tennis and pickleball courts, fitness facilities, three clubhouses, and miles of scenic walking paths and boardwalks winding through lush tropical landscaping. Pelican Cove is also known for its exceptionally active community, offering numerous resident clubs, art and creative programs, educational opportunities, concerts, fitness activities and year-round social events. All of this is tucked away in a beautiful Sarasota location, convenient to Siesta Key, shopping, restaurants, the Legacy Trail and downtown Sarasota. Everything has been done — bring your furniture and start enjoying the Pelican Cove lifestyle!

1720 Glenhouse Drive Unit 328, Sarasota
1650 Assisi Drive Unit 16, Sarasota
$1,425,000
4 Beds ⋅ 4 Baths ⋅ Portofino On The Bay SubDv. ⋅ 34231 Zip Code
Nestled within the gated community of Portofino on the Bay, an intimate Mediterranean-inspired enclave of just twenty homesites in the Sarasota/Vamo area, this residence offers an inviting coastal setting and an active Florida lifestyle. Enjoy deeded access to Little Sarasota Bay, complete with a community dock, kayak storage and launch, and the potential to purchase a private boat slip with lift separate to community homeowner when available. Double entrance doors open into a two-story foyer, introducing an open-concept floor plan complemented by soft, welcoming wall tones, custom window and door trim, and crown molding across both levels. Plantation windows shutters add a classic touch throughout the entire home—including the garage, which features durable epoxy flooring. In the main living room, an accent stone floor to ceiling gas fireplace serves as a centerpiece for gathering or relaxing in the evening. The adjacent kitchen offers bright, clean-lined soft-close cabinetry, a built-in cooktop, stainless steel appliances, and a convenient closet pantry. The main-floor Owner’s Retreat provides a comfortable private wing, complete with its own dedicated A/C zone (one of three independent systems in the home). The bedroom features a tray ceiling and French doors opening directly to the pool patio. The ensuite bathroom is equipped with dual sinks, a makeup vanity, a walk-in shower, a bidet, a generous walk-in closet with custom built-ins and a tub ready for relaxation with bubbles after a day on the water. A main-floor den with tray ceilings offers flexible space for a home office or reading room, complemented by a main-level guest half bath. Upstairs via the wrought-iron staircase railing, a central loft connects to three additional bedrooms—each accented with tray ceilings. Two of the guest rooms share direct access to a private outdoor balcony, while the fourth bedroom showcases soaring ceiling height and abundant natural light, all cooled by a dedicated second-floor A/C zone. Step out back to the newly extended panoramic-screened lanai, finished with travertine tile surrounding the heated salt-water pool and spa. A convenient pool half bath and an outdoor shower make outdoor living effortless. Situated in an X Flood Zone with no prior hurricane damage, this home is also exceptionally well-located: just a 10-minute drive (6 miles) to world-renowned Siesta Key Beach and 15 minutes (9 miles) to vibrant Downtown Sarasota for premier dining, arts, and shopping. The new Sarasota Square presently being remodel led with approximately 90,000 square feet of daily-needs retail scheduled for delivery in the first quarter of 2027 plus with easy Costco shopping.

1650 Assisi Drive Unit 16, Sarasota
2740 Riverbluff Parkway Unit V107, Sarasota
$220,000
1 Beds ⋅ 2 Baths ⋅ Strathmore Riverside SubDv. ⋅ 34231 Zip Code
Welcome to Strathmore Riverside Villas, a waterfront 55+ community in South Sarasota just east of the Tamiami Trail. This free-standing villa is one of only a handful in the community that stands entirely on its own, offering no shared walls and windows on all four sides for added natural light and privacy. The flexible floor plan features one bedroom plus a den that could easily be converted to a second bedroom, along with one and a half baths and comfortable living spaces that flow naturally throughout the home. The living room and dining area are finished with bamboo flooring and crown molding, while the den offers additional space for guests, a home office, hobby room, or second bedroom depending on your needs. At the center of the home, the updated kitchen features white raised-panel cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, floating shelves, and a window above the sink. Just beyond the kitchen, the Florida room is wrapped in windows and finished with light wood-look plank flooring, creating a bright space to relax with its own exterior entrance. The primary bedroom is privately positioned with wood-look plank flooring, a reclaimed wood accent wall, walk-in closet, and ensuite bath featuring a frameless glass walk-in shower. The interior laundry room also serves as a convenient half bath for guests and includes a full-size washer and dryer, vanity sink, and built-in storage. Hurricane glass windows and energy-efficient appliances are already in place, and the roof is only three years old. Outside, a private driveway leads to the covered carport and tiled entry patio, while an exterior storage closet provides room for bikes, beach gear, and more. Mature landscaping and open lawn surround the villa. Community amenities include a waterfront clubhouse, heated pool, saunas, exercise room, billiard room, library, and an active social calendar. Boaters can enjoy the 33-slip marina with an on-site dockmaster and slips available on a first-come basis for $20 per month, providing canal access to Phillippi Creek, the Intracoastal Waterway, and the Gulf beyond. Siesta Key, Gulf Gate dining and shopping, Downtown Sarasota, and US 41 are all within easy reach. Come experience the flexibility of this unique free-standing villa and the waterfront lifestyle of Strathmore Riverside Villas in person. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

2740 Riverbluff Parkway Unit V107, Sarasota
2327 Waterbluff Place Unit V315, Sarasota
$220,000
2 Beds ⋅ 2 Baths ⋅ Strathmore Riverside SubDv. ⋅ 34231 Zip Code
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 a BRAND NEW HVAC system in September 2026 with 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, Sarasota
5823 Tidewood Avenue Unit 19, Sarasota
$289,900
2 Beds ⋅ 2 Baths ⋅ Baywood Colony SubDv. ⋅ 34231 Zip Code
COMPLETELY REMODELED & MOVE-IN READY! Welcome home to this beautifully updated 2-bedroom, 2-bath villa featuring a desirable split-bedroom floor plan and stylish improvements throughout. Step inside to a bright, fresh interior showcasing NEW PAINT and LUXURY VINYL FLOORING THROUGHOUT, creating a clean, cohesive look with easy-care living. The stunning NEW KITCHEN is the heart of the home, featuring QUARTZ COUNTERTOPS, NEW STAINLESS-STEEL APPLIANCES, and plenty of workspace for everyday meals and entertaining. Both bathrooms have been thoughtfully remodeled with attractive, modern finishes that complement the home's updated design. Major improvements provide added peace of mind, including a NEW ROOF and NEW HURRICANE-IMPACT WINDOWS AND DOORS THROUGHOUT. Additional conveniences include a PRIVATE LAUNDRY ROOM and COVERED CARPORT, adding valuable storage and functionality to everyday living. The updated lanai provides a wonderful extension of the living space—perfect for morning coffee, relaxing with a good book, or enjoying an evening meal.Beyond the villa, the community offers a relaxed Florida lifestyle with an ACTIVE CLUBHOUSE, BEAUTIFUL COMMUNITY POOL, and a peaceful, park-like setting along LITTLE SARASOTA BAY, where you can unwind and enjoy spectacular sunsets. Best of all, you're just a short bike ride from SIESTA KEY'S WORLD-FAMOUS WHITE-SAND BEACHES, along with nearby restaurants, shopping, and entertainment. With its extensive renovations, desirable location, and truly move-in-ready condition, this villa offers an exceptional opportunity to enjoy the best of Florida living!

5823 Tidewood Avenue Unit 19, Sarasota
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