South Side Park Homes for Sale

South Side Park Homes for Sale

Welcome to South Side Park, a charming subdivision nestled in the heart of Central Sarasota, Florida. This delightful community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and professionals alike. With its lush greenery, friendly neighbors, and a strong sense of community, South Side Park is a hidden gem waiting to be discovered.

The homes for sale in South Side Park showcase a variety of architectural styles, from cozy single-family residences to modern contemporary designs, catering to diverse tastes and lifestyles. Many of these homes feature spacious layouts, well-manicured yards, and inviting outdoor spaces perfect for entertaining or simply enjoying the Florida sunshine. With an array of options available, potential buyers will find homes that suit their needs, whether they are seeking a starter home or a more expansive property.

Residents of South Side Park enjoy easy access to a wealth of amenities, including parks, shopping centers, and dining options. The area is known for its excellent schools and proximity to cultural attractions, such as the renowned Ringling Museum of Art and the vibrant downtown Sarasota scene. For those who love the outdoors, stunning beaches and nature preserves are just a short drive away, offering endless opportunities for recreation and relaxation.

If you're looking for a welcoming community with a strong sense of belonging, South Side Park might just be the perfect place for you to call home. Explore the available homes for sale today and start envisioning your new life in this enchanting Sarasota neighborhood!

Newest South Side Park Homes for Sale

$995,000
2 Beds ⋅ 1 Baths ⋅ A11380195 MLS
Excellent INVESTMENT and/or an AMAZING DEVELOPMENT OPPORTUNITY awaits the perfect vision. In the beautifully tree-lined streets of Parkside is the gem of Hollywood. Conveniently in the heartbeat of it all, with a smattering of single-family homes of assorted architectural styles and a lovely mix of multiplexes and small boutique style buildings. This property can be developed up to 14-stories. Currently, a Mid-Century modern 2-Bed/1-Bath Pool home w/ lush landscaping, easily converts to a 3-Bed/2-Bath adding wall & turning the laundry rm into a bath -making a Primary Suite. Setbacks only 10-ft from the front and back. A must see for both investor & home owner alike, endless ROI potential. Walking distance to restaurants, nightlife, bars, cafes, and the Arts & Entertainment district

2018 Fletcher Street, Hollywood
$500,000
3 Beds ⋅ 2 Baths ⋅ A12048173 MLS
Great corner property! This home features 3 bedrooms, 2 full baths, plus large Den, could easily be used as a 4th bedroom. Master suite has walk in closet. Living room has exposed wood beams. Laundry Room. 1 car carport. Fenced backyard. Walking distance to downtown Hollywood, short drive to Hollywood Beach and Hollywood Ft. Lauderdale Airport

1300 S 20th Avenue, Hollywood
$269,900
3 Beds ⋅ 2 Baths ⋅ L4962951 MLS
Virtually Staged. Did you see the improved listing price?! Welcome to 3142 Henderson Circle W, Lakeland, Florida 33803! This centrally located Southwest Lakeland home offers 3 bedrooms, 2 bathrooms and approximately 1,457 square feet of living space on a spacious 0.21-acre homesite. The practical split-bedroom floor plan provides added privacy, while the versatile 11-by-12-foot bonus room offers flexible space for a home office, media room, hobby area, playroom or possible fourth bedroom. Interior features include an inviting living area, updated flooring, kitchen cabinetry, bathroom vanities, windows, blinds and appliances. The primary bedroom includes a walk-in closet and private bathroom. Outside, the partially fenced backyard provides room for outdoor entertaining, gardening, pets or future improvements. A detached 16-by-12-foot workshop offers valuable storage and workspace for tools, equipment or hobbies. The double driveway provides convenient off-street parking. Located in Lakeland’s desirable 33803 ZIP code, this Central Florida home offers convenient access to downtown Lakeland, Florida Southern College, Lakeside Village, shopping, restaurants, parks, medical facilities and major roadways connecting Lakeland with Tampa and Orlando. Whether you are searching for a primary residence, Lakeland investment property or a home with an office and workshop, 3142 Henderson Cir W combines a flexible floor plan, usable outdoor space and a convenient Southwest Lakeland location. Schedule your private showing today! *** UPDATES and MAINTENANCE: New AC 2025. New roof 2020. Shed added 2022. Plumbing updated 2025. Bonus / WIC wood look floor added 2024. Back yard pavers added. *** Please take a virtual tour (click the "no furniture" icon to see vacant rooms), and have a look at the pictures. If you can see yourself making this a home, please request a private showing today!

3142 Henderson Circle W, Lakeland
$1,149,000
4 Beds ⋅ 4 Baths ⋅ A4692960 MLS
Exceptional opportunity to own a fully renovated, income-generating property with a strong track record of short-term rental success. This 4-bedroom, 3.5-bath home, located in the highly desirable Arlington Park area of Sarasota, was completely renovated in 2020, offering modern finishes, updated systems, and true turnkey condition for both personal use and continued rental income. For the past six years, the property has operated as a successful short-term rental, delivering consistent performance and strong guest demand. Even more compelling, there are future reservations already in place for 2026 and 2027, providing immediate, built-in income for the next owner. The spacious layout is ideal for accommodating larger groups, and the home has been meticulously maintained to meet guest expectations and maximize occupancy. Step outside to a private backyard retreat featuring a heated swimming pool, expansive deck, and a covered patio with a built-in outdoor grilling island—perfect for entertaining guests and enhancing the rental experience year-round. The listing agent is also the current property manager and has successfully managed the home over the past six years. For buyers seeking a seamless transition, professional management can continue in place, offering a true hands-off investment opportunity. Ideally situated less than 10 minutes to Downtown Sarasota and the world-renowned Siesta Key beaches, this location consistently attracts both vacationers and long-term visitors alike. 2201 Weber Street offers a rare combination of modern renovation, established income history, future bookings, resort-style outdoor living, prime location, and optional ongoing management—making it an exceptional opportunity for investors and second-home buyers alike.

2201 Webber Street, Central Sarasota
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