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 an inviting blend of community spirit and natural beauty, making it the perfect place to call home. With its lush landscapes, tree-lined streets, and a variety of architectural styles, South Side Park radiates a warm and welcoming atmosphere.

Residents of South Side Park enjoy a lifestyle that balances tranquility with convenience. The subdivision is strategically located just minutes away from the vibrant downtown Sarasota area, where you can explore an array of dining, shopping, and entertainment options. The nearby beaches, including the stunning Siesta Key and Lido Key, are also just a short drive away, providing endless opportunities for sun-soaked days and picturesque sunsets.

Families will appreciate the excellent schools and parks in the vicinity, which offer recreational activities for all ages. South Side Park features a community park that serves as a hub for social gatherings, picnics, and outdoor fun. Whether you’re taking a leisurely stroll, enjoying a morning jog, or simply soaking in the serene surroundings, this neighborhood fosters a strong sense of community.

With a diverse range of homes available, from cozy bungalows to spacious family residences, South Side Park caters to various lifestyles and preferences. If you’re seeking a place where community, convenience, and charm intersect, look no further than South Side Park in Central Sarasota. Discover your new home in this delightful subdivision and experience the best of Florida living!

Newest Listings in South Side Park

$269,900

3 Beds ⋅ 2 Baths ⋅ South Side Park SubDv. ⋅ 33803 Zip Code

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 ⋅ 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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