South Side Park Real Estate

South Side Park Real Estate

Welcome to South Side Park, a hidden gem nestled in the heart of Central Sarasota, Florida. This charming subdivision is renowned for its inviting atmosphere, lush greenery, and a strong sense of community. Perfectly situated near the vibrant downtown area, South Side Park offers residents the best of both worlds: the tranquility of suburban living combined with easy access to urban amenities.

As you stroll through the tree-lined streets, you’ll discover beautifully maintained homes that reflect a variety of architectural styles, from classic Floridian bungalows to modern designs. The neighborhood is characterized by its friendly neighbors and a welcoming spirit, making it an ideal place for families, retirees, and everyone in between.

South Side Park is not just about stunning homes; it also boasts an array of recreational opportunities. Residents can enjoy the nearby parks, perfect for picnics, jogging, or simply soaking up the sun. The proximity to Sarasota’s renowned beaches means that sun-soaked days by the ocean are just a short drive away. Additionally, the area is rich in cultural attractions, including art galleries, theaters, and an array of dining options that cater to every palate.

For those who value community engagement, South Side Park hosts various neighborhood events throughout the year, fostering connections and friendships among residents. With its prime location, beautiful homes, and a vibrant community spirit, South Side Park is truly a wonderful place to call home in Central Sarasota. Come experience the charm of South Side Park and discover your dream home today!

Newest Listings in South Side Park

$924,900
B26065061 MLS
Southside Villas presents an exceptional opportunity to acquire a well-located 5-income producing unit multifamily property in the heart of Hollywood, Florida. Situated just moments from the vibrant Arts Park at Young Circle, the property offers residents convenient access to Downtown Hollywood's thriving dining, entertainment, shopping, and cultural destinations. Hollywood continues to experience strong population growth, ongoing redevelopment, and increasing rental demand driven by its strategic location between Fort Lauderdale and Miami. The property's central location places tenants within minutes of Hollywood Beach, Memorial Regional Hospital, Fort Lauderdale-Hollywood International Airport, and numerous employment centers throughout South Florida. The property has seen capital improvements, providing investors with a strong foundation for long-term ownership. Recent upgrades include the installation of hurricane impact windows, enhancing both safety and operational efficiency while reducing future capital expenditure requirements. Additional improvements have contributed to the property's overall appeal and tenant retention, and upgraded kitchen and bathroom in one unit positioning Southside Villas as a value-add investment with continued upside potential.

1314 S 20TH Avenue, Hollywood
$3,000,000
A12061033 MLS
Shovel-Ready Multifamily Development Opportunity – Hollywood, FL | 2022–2026 Fletcher Street. An exceptional opportunity for developers to acquire a shovel-ready site with fully approved plans for a contemporary five-story, 42-unit multifamily development. The project consists of 32 one-bedroom/one-bath units and 10 two-bedroom/two-bath units, along with 58 parking spaces, a fitness center, and a rooftop common area offering panoramic views. Strategically located in the heart of Hollywood, this project is ideally positioned to capitalize on the strong and growing demand for high-quality rental housing in one of South Florida’s fastest-growing submarkets. Residents will benefit from convenient access to Downtown Hollywood, world-class beaches, vibrant dining and entertainment, major transportation corridors, and nearby casino destinations. With approvals in place and construction positioned to begin by year-end or sooner, this offering presents a compelling opportunity to deliver a modern multifamily community in a highly desirable South Florida location.

2022 Fletcher Street, Hollywood
$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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