South Sarasota Homes under $500,000

South Sarasota Homes under $500,000

Welcome to South Sarasota, a hidden gem nestled in the heart of Florida’s picturesque Gulf Coast. Known for its lush landscapes, vibrant community, and stunning beaches, South Sarasota offers a perfect blend of relaxation and recreation. With its warm, sunny climate and a laid-back atmosphere, this charming city is an ideal destination for families, retirees, and anyone seeking a serene lifestyle.

One of the most appealing aspects of South Sarasota is its diverse real estate market. If you’re searching for homes under $500,000, you’ll be delighted to discover a wide variety of options. From cozy single-family homes to modern townhouses, the choices are plentiful. Many properties feature spacious yards, inviting outdoor spaces, and proximity to local parks, making them perfect for families and pet lovers alike.

South Sarasota is not just about beautiful homes; it’s also about a vibrant lifestyle. Residents enjoy easy access to pristine beaches, world-class dining, and boutique shopping. The nearby Legacy Trail invites outdoor enthusiasts to explore scenic paths, while cultural attractions like art galleries and theaters enrich the community's artistic spirit.

With its affordable housing options and a welcoming atmosphere, South Sarasota is a place where dreams of homeownership can become a reality. Whether you’re looking to settle down or invest, this charming city has something for everyone. Discover the beauty of South Sarasota today, and find your perfect home under $500,000 in this idyllic Floridian paradise!

Newest South Sarasota Homes under $500,000

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
3416 Wilkinson Woods Drive Unit 63, Sarasota
$335,000
3 Beds ⋅ 2 Baths ⋅ Wilkinson Woods SubDv. ⋅ 34231 Zip Code
Beautifully updated 3-bedroom, 2-bath villa in the desirable Wilkinson Woods community, offering a spacious, comfortable floor plan in an incredibly convenient Sarasota location! Step inside and you’ll immediately appreciate the attention to detail, including crown molding, abundant natural light, and an updated kitchen designed for both style and everyday functionality. The kitchen features attractive finishes and thoughtfully designed pull-out storage, making cabinets and pantry items easy to access. The spacious living and dining areas flow nicely for entertaining, while the enclosed sunroom provides additional flexible living space with the floor professionally raised to create a level transition with the rest of the home. The large dining room mirror conveys and adds an attractive finishing touch to the space. Additional improvements include impact-resistant windows throughout the home, with the exception of the double French doors in the office, which are not impact glass. The HVAC system was installed in 2021 or newer and features a UV light installed in 2026. The water heater was replaced in August 2024, followed by the addition of a hot water circulation system in October 2024. The washer and dryer also convey. Storage is another standout feature, with a new attic access ladder and illuminated attic storage space above the garage. An invisible pet fence provides another convenient feature for pet owners. Wilkinson Woods offers a relaxed Sarasota lifestyle with community amenities including a clubhouse, swimming pool, tennis courts, and reclaimed-water irrigation. Association fees include cable TV, community pool access, common area insurance, exterior maintenance, grounds maintenance, and recreational facilities. The association has indicated that roof replacement is anticipated as part of a future community-wide roof project; timing and details should be independently verified with the association. Located in the heart of Sarasota, this home provides convenient access to shopping, restaurants, grocery stores, medical facilities, downtown Sarasota, Siesta Key and its world-famous beaches, Gulf Gate, cultural attractions, and Sarasota-Bradenton International Airport. If you’ve been looking for an updated Sarasota villa with generous living space, extensive improvements, community amenities, and easy access to everything the area has to offer, 3416 Wilkinson Woods Drive is one you’ll want to see!

3416 Wilkinson Woods Drive Unit 63, Sarasota
3048 Savage Road, Sarasota
$475,000
3 Beds ⋅ 2 Baths ⋅ Palm Lakes SubDv. ⋅ 34231 Zip Code
Beautifully remodeled 3-bedroom, 2-bathroom ranch-style home in the highly desirable Gulf Gate area. Thoughtfully renovated from top to bottom, this move-in-ready home offers a fresh, modern feel with quality updates throughout. The stylish new kitchen features white shaker cabinetry, quartz countertops, and stainless-steel appliances. Both bathrooms have been tastefully remodeled, while new luxury vinyl flooring and LED lighting add a clean, contemporary touch throughout the home. Major updates include impact windows, new sewer lines, and underground utilities, providing peace of mind for years to come. The spacious floor plan offers generously sized rooms, with two of the three bedrooms featuring large walk-in closets for excellent storage. Whether you’re looking for a full-time residence, second home, or investment property, this home offers flexibility to fit your needs. Enjoy the convenience of being just minutes from the restaurants, shops, and local businesses of bustling Gulf Gate, with the world-renowned beaches of Siesta Key only a few miles away. Move right in and enjoy all the updates, or take advantage of the opportunity to keep the current tenant, who is clean and would be happy to stay. A fantastic opportunity to own a completely updated home in a convenient Sarasota location!

3048 Savage Road, Sarasota
1841 Joyce Street, Sarasota
$429,000
2 Beds ⋅ 2 Baths ⋅ Vamo SubDv. ⋅ 34231 Zip Code
Morning paddle boarding on Little Sarasota Bay. An afternoon at Siesta Key Beach. Dinner back home on your own patio. At 1841 Joyce Street, Sarasota’s coastal lifestyle comes with a two-bedroom home, a fully fenced backyard, no HOA and a new roof in 2025. Located west of US 41 in Sarasota’s Vamo neighborhood, this single-story, two-bedroom home offers 1,318 square feet with a bright Florida room that gives you extra space to relax or entertain. The connected living, dining and kitchen areas keep everyone together, while white cabinetry, light countertops and stainless steel appliances give the kitchen a fresh, welcoming feel. A dedicated office area provides the flexibility to comfortably work from home, while the light-filled Florida bonus room offers even more versatile living space with Windows on three sides bringing natural light into the Florida room, an inviting place for morning coffee, a good book or gathering with friends. Outside, the long paver patio extends your living space into the fully fenced backyard, with room for outdoor dining, gardening, pets and keeping kayaks or bikes close at hand. Recent improvements include a new roof in 2025, stainless steel appliances, water heater, electrical panel, toilets and exterior stucco. Significant electrical preparation has also been completed for the addition of a future whole-house generator. Walk to Vamo Drive Park and its public canoe and kayak launch on Little Sarasota Bay, where you can get out on the water, enjoy the shoreline and watch for local wildlife. Nearby Wharf Road Park offers another waterfront spot to explore. When the beach calls, drive across the Stickney Point bridge to Siesta Key for quartz sand, swimming in the Gulf and sunsets, with island restaurants ready to round out the day. Gulf Gate dining, plus the exciting redevelopment of the former Sarasota Square Mall bringing many new restaurants, Shops and much more to the area for everyday convenience. Whether you’re looking for a year-round Sarasota home or a seasonal place to return to, 1841 Joyce Street brings together coastal recreation, comfortable indoor and outdoor living, and recent improvements that make this home worth a closer look.

1841 Joyce Street, 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
84 Southwinds Drive, Sarasota
$264,900
2 Beds ⋅ 2 Baths ⋅ South Winds Mobile Home Park Co-Op SubDv. ⋅ 34231 Zip Code
Welcome home to this absolutely immaculate double-wide in desirable Southwinds Mobile Home Park! Affordable living with monthly HOA dues of only $195 a month make this attractive immediately! Beautifully maintained, this inviting home offers a warm coastal feel from the moment you step inside. Don’t wait on this one—it’s a beauty and you'll love the tasteful furniture and decor! The spacious floorplan features 2 bedrooms plus a versatile den that could easily serve as a 3rd bedroom, home office, or guest space. Enjoy both formal living and dining areas, a comfortable Florida Room, and a spacious kitchen with a separate dinette. Sliding glass doors from the dinette bring in plenty of natural light and overlook the front of the home. Additional features include a covered carport, storage shed, and convenient inside laundry closet with washer and dryer included. Many improvements by Sellers including the following: Shingle Roof 2026*Shed Door 2025*Microwave 2023*Air Conditioner 2023*Washer 2020*Flooring upgraded 2019*FL Room Roof 2019*10 x 8 Shed for storage & much more! Situated toward the back of the community, the home enjoys a quieter location while still being just a short distance from the clubhouse and community amenities. The community pool is always a great place to meet up with your friends in the park, as well as pickleball and shuffleboard too! And ... the location is hard to beat! World-renowned Siesta Key and its beautiful beaches are just minutes away, along with the popular Gulf Gate shops and restaurants. Legacy Trail, Costco, fitness centers, shopping, and an abundance of dining options are all nearby. Cultural downtown Sarasota is approximately 15 minutes away, offering boutique shopping, restaurants, theaters, the opera, Marie Selby Botanical Gardens, and so much more. Southwinds is a welcoming 55+ co-op community known for its friendly atmosphere and wonderful sense of community. Come enjoy the Florida lifestyle and become part of this special neighborhood. This one truly stands out—schedule your showing today!

84 Southwinds Drive, Sarasota
2920 Clark Road Unit 102, Sarasota
$174,900
2 Beds ⋅ 1 Baths ⋅ Town N Country SubDv. ⋅ 34231 Zip Code
Enjoy a convenient Sarasota location just minutes from Siesta Key! Unit 102 at Town 'N Country offers easy access to everything that makes this area so desirable. Siesta Key Beach is less than 3 miles away, while Detwiler's Farm Market, Publix, shopping, restaurants, and everyday services are nearby. Sarasota-Bradenton International Airport is approximately 10 miles from the property. Residents enjoy a community swimming pool, courtyard, and shared laundry facilities. The building roof was also replaced in 2022. For buyers seeking a larger investment opportunity, Units 101, 102, and 204 at 2920 Clark Road are all being offered together by the owner. Acquiring multiple units within the same building creates a unique opportunity to establish or expand a Sarasota real estate portfolio while keeping properties in one convenient location.

2920 Clark Road Unit 102, Sarasota
2920 Clark Road Unit 101, Sarasota
$174,900
2 Beds ⋅ 1 Baths ⋅ Town N Country SubDv. ⋅ 34231 Zip Code
LOCATION, CONVENIENCE, AND OPPORTUNITY come together at Town 'N Country in Sarasota! Unit 101 is ideally positioned along the Clark Road corridor, less than 3 miles from Siesta Key Beach and close to shopping, dining, Detwiler's Farm Market, Publix, and everyday conveniences. Sarasota-Bradenton International Airport is approximately 10 miles away. The community offers a swimming pool, courtyard, and shared laundry facilities, while the building roof was replaced in 2022. Adding to the opportunity, Units 101, 102, and 204 at 2920 Clark Road are all being offered together by the same owner, providing the chance to acquire three units within the same building. Whether you're looking to expand your real estate portfolio or secure multiple Sarasota properties in one convenient location, this is an opportunity worth considering.

2920 Clark Road Unit 101, Sarasota
2920 Clark Road Unit 204, Sarasota
$174,900
2 Beds ⋅ 1 Baths ⋅ Town N Country SubDv. ⋅ 34231 Zip Code
Discover a conveniently located Sarasota condo just a short drive from Siesta Key. Unit 204 at Town 'N Country is less than 3 miles from Siesta Key Beach and near Detwiler's Farm Market, Publix, restaurants, shopping, and other everyday conveniences. Sarasota-Bradenton International Airport is approximately 10 miles away. Community amenities include a swimming pool, central courtyard, and shared laundry facilities, and the building roof was replaced in 2022. A particularly unique feature of this offering is the availability of Units 101, 102, and 204, all being offered together by the same owner. This provides an appealing opportunity for a buyer looking to acquire three properties within one Sarasota building, with beaches, shopping, dining, and recreation all within easy reach.

2920 Clark Road Unit 204, Sarasota
5697 Ashton Lake Drive Unit 6, Sarasota
$236,000
2 Beds ⋅ 2 Baths ⋅ Ashton Lakes SubDv. ⋅ 34231 Zip Code
Location! Location! Location! Only 3.5 miles to the world-famous Siesta Key Beach. This much sought after 2-bedroom 2 bath, ground floor unit overlooking the vast expanse of Sunnyside Lake with very pleasant view. The screened lanai faces east and could be your observation deck as the Florida Wildlife entertains you. Unit is bright and airy. Updated in 2021 with vinyl floor, kitchen cabinets granite counter, updated bathrooms, and new stainless-steel kitchen appliances that will be installed the first week in October. Ashton Lakes is located on 33 acres of luscious greenery, with 4 lakes, a combination of 2 tennis courts and 4 pickleball courts, a shuffleboard, clubhouse, 2 heated pools, the large one with a lap lane, grilling stations and other amenities. Close to I-75 and rte.41, hospitals, schools, restaurants, shopping etc. We are also connected to Merchants Mart shopping center by a foot bridge, shops such as ACE, CVS, Restaurants, beauty salon, liquor store and the famous Detwiller's Farm Market. Roof 2009. Come be a part of this friendly community...

5697 Ashton Lake Drive Unit 6, Sarasota
2127 Shawnee Street, Sarasota
$359,000
4 Beds ⋅ 2 Baths ⋅ Las Lomas De Sarasota SubDv. ⋅ 34231 Zip Code
Opportunity, flexibility, and a hard-to-beat South Sarasota location come together at 2127 Shawnee Street. Located in the established Las Lomas de Sarasota neighborhood, this 4-bedroom 2-bath property offers approximately a versatile layout that creates options for homeowners, investors, or anyone looking to offset their monthly expenses with rental income. The main portion of the home is configured as a 3-bedroom, 1-bath residence, while the separate mother-in-law suite offers a studio-style living space with its own kitchenette and full bathroom. The studio is currently rented for $1,250 per month, with potential for increased rental income based on current market conditions. Major improvements include a roof replaced in 2021 and an A/C system replaced in 2024, helping take care of two of the bigger-ticket items buyers look for. Outside, the property offers even more usable space with a 250+ square-foot screened lanai overlooking a large, fully fenced backyard. A separate block storage building provides plenty of room for tools, bikes, beach gear, lawn equipment, and more. Parking is another standout feature, with a horseshoe-style driveway and single-car covered parking providing room for multiple vehicles. The covered parking area may also offer future possibilities for additional living space, subject to applicable zoning, permitting, and approvals. The location is where this property really shines. Las Lomas de Sarasota sits in the heart of South Sarasota, directly across from The Landings area and convenient to shopping, dining, Sarasota Memorial Hospital, Downtown Sarasota, and everything along the US-41 corridor. Best of all, Siesta Key and its world-famous beaches are less than two miles away, putting one of Sarasota's biggest attractions practically in your backyard. Whether you're looking for an affordable Sarasota home with additional income to help offset your mortgage, a multi-generational living setup, or an investment property with multiple ways to generate value, 2127 Shawnee Street offers the kind of versatility that's increasingly difficult to find this close to Siesta Key. OWNER FINANCING AVAILABLE!!

2127 Shawnee Street, Sarasota
2609 Woodgate Lane Unit K4, Sarasota
$209,900
2 Beds ⋅ 2 Baths ⋅ Pinewood Village SubDv. ⋅ 34231 Zip Code
The work is done, so you can relax and enjoy life. This totally transformed ground-floor condo in Pinewood Village sits less than 10 minutes from the Siesta Key beaches, and every room shows the care that went into it. A private sidewalk winds between palms, crotons, and oversized elephant ears to a deep covered porch, where a café table waits for morning coffee and a good book. Step through the glass-paneled storm door and the home opens up in light: crisp white walls, clean white baseboards, and wide wood-look luxury vinyl planks in a pale natural oak tone running uninterrupted from the entry to the sliding glass doors. The kitchen is where the transformation hits first. White shaker uppers sit over warm honey-toned wood lowers, finished with brushed gold bar pulls. White quartz counters with a soft sparkle wrap around to an undermount stainless sink with a sleek pull-down faucet, set against a glossy handmade-look tile backsplash that catches the light. A stainless French-door refrigerator, glass-top range, dishwasher, and under-cabinet hood complete the space, while recessed lighting and a modern ring-light ceiling fan give the room a polished, contemporary glow. A pass-through with a quartz ledge keeps the kitchen connected to the dining area, so whoever is cooking is never left out of the conversation. The bathrooms are the moment you'll remember. In one, the shower is wrapped floor to ceiling in fluted wood-look tile, grounded by a river-pebble floor and finished with a recessed niche trimmed in gold, a square rain showerhead, and a brushed gold handheld on a slide bar. A wood shaker vanity with quartz top and gold faucet sits beneath an arched black-framed mirror and a soft LED light bar. The second bath takes a different mood: glossy sea-green vertical tile surrounds the tub, paired with a gold rain showerhead, a round gold-framed mirror, and a light wood vanity with brushed gold hardware. Two bathrooms, two personalities, and both feel like a personal spa. Every room has a fan with lights, there are no popcorn ceilings, and even the doors have been freshly painted. There's also a separate laundry room with a washer, dryer, and utility sink. Slide open the glass doors and the Florida room pulls you in. Tall PGT windows wrap the space, overlooking green lawn and swaying palms, with the pool just steps away. It's the spot for slow mornings and sunset evenings. The building is concrete construction, including concrete ceilings, for a quiet, near-soundproof living experience. HVAC and heat pump are brand NEW (Sept 2026) and ducts replaced 2023. The home is in flood zone X, and water, cable, internet, and grounds maintenance are included. Pinewood Village offers a heated community pool, a fitness center, a sauna, a clubhouse with a kitchen, and shuffleboard courts. Enjoy an afternoon close to home, then head out to explore what makes this location so appealing: Siesta Key Beach for a day on the sand, Phillippi Estate Park for a walk beneath the trees, or Gulf Gate for its restaurants and neighborhood gathering spots. Downtown Sarasota brings waterfront walks at Bayfront Park, performances at the Sarasota Opera, and dining along Main Street and Palm Avenue. Whether you're making Sarasota your year-round home or returning each season, 2609 Woodgate Lane is ready for you. All you have to bring is your toothbrush.

2609 Woodgate Lane Unit K4, Sarasota
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