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 offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and anyone seeking a vibrant community atmosphere.

South Side Park is characterized by its lush, tree-lined streets and beautifully maintained homes, each exuding unique architectural charm. The neighborhood boasts a friendly, welcoming vibe, where neighbors become friends and community spirit thrives. Residents enjoy easy access to a variety of local amenities, including parks, shopping centers, and dining options that cater to every palate.

One of the standout features of South Side Park is its proximity to some of Sarasota’s most beautiful beaches. Just a short drive away, you can bask in the sun on the soft sands of Siesta Key or explore the vibrant cultural scene downtown. For those who enjoy outdoor activities, the nearby parks and recreational facilities provide ample opportunities for hiking, biking, and enjoying Florida’s stunning natural landscape.

Families will appreciate the highly-rated schools within the Sarasota County School District, ensuring a quality education for children of all ages. Additionally, the community hosts various events throughout the year, fostering connections among residents and creating a sense of belonging.

In South Side Park, you’ll find not just a home, but a lifestyle enriched by community, convenience, and the beauty of Florida living. Come discover why this delightful neighborhood is the perfect place to call home!

Newest Listings in South Side Park

$500,000
2 Beds ⋅ 2 Baths ⋅ South Side Park SubDv. ⋅ 34239 Zip Code
Opportunity knocks in one of Sarasota's most sought after neighborhoods. Surrounded by multimillion dollar homes, this 2 bedroom, 2 bathroom pool home is ideal for investors, builders, renovators, or buyers looking to secure a prime piece of real estate and create something truly special. Whether you envision a complete renovation or a future custom home, the possibilities are endless. Set on a mature lot with tropical plants, this property offers exceptional privacy and a tranquil setting. The screened pool area is the centerpiece of the home, providing the perfect space to entertain, unwind, or transform into an impressive outdoor living area. Inside, the home features higher ceilings, two spacious living areas, generously sized bedrooms with built in closets, and a Location doesn't get much better than this. You're minutes from everything that makes Sarasota special, Sarasota Memorial Hospital is less than a mile away, Downtown Sarasota and Main Street's shops and restaurants are just under two miles down the road, and world-famous Siesta Key Beach is a quick four-mile drive. Outdoor lovers will appreciate Arlington Park right around the corner, with its walking trails, tennis courts, aquatic center, playgrounds, and dog park. Families will also love that the home falls within a highly rated school districts all within walking distance. Additional features include city water and sewer, a carport, and an estimated 4 year old air conditioning system. The roof is estimated to be approximately 15 years old. Properties with this combination of location, value, and potential are becoming increasingly difficult to find. Bring your vision and take advantage of this exceptional opportunity before it is gone.

2742 S East Avenue, Sarasota
$274,900
3 Beds ⋅ 2 Baths ⋅ South Side Park SubDv. ⋅ 33803 Zip Code
Virtually Staged. 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 ⋅ South Side Park SubDv. ⋅ 34239 Zip Code
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, Sarasota
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