Jackson Square Real Estate

Jackson Square Real Estate

Welcome to Jackson Square, a charming subdivision nestled in the heart of St. Petersburg, Florida, within the picturesque Pinellas County. This vibrant community offers a unique blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike.

Jackson Square is characterized by its beautifully landscaped streets, lined with a mix of modern homes and classic Florida architecture. The subdivision exudes a warm, welcoming atmosphere, where neighbors become friends and community spirit thrives. With an array of parks and recreational areas nearby, residents can enjoy outdoor activities, from leisurely strolls to picnics in the sun.

One of the standout features of Jackson Square is its proximity to the stunning Gulf Coast beaches, just a short drive away. Imagine spending your weekends basking in the sun on the sandy shores, indulging in water sports, or enjoying a sunset stroll along the beach. For those who appreciate a vibrant arts scene, downtown St. Petersburg is just minutes away, offering an eclectic mix of galleries, theaters, and cultural events.

Families will also appreciate the quality of schools in the area, ensuring that children receive a top-notch education. With a variety of shopping and dining options close by, residents have everything they need right at their fingertips.

In Jackson Square, you’re not just purchasing a home; you’re investing in a lifestyle filled with warmth, community, and endless opportunities for adventure. Discover the charm of Jackson Square and make it your next home sweet home!

Newest Listings in Jackson Square

$185,000
2 Beds ⋅ 1 Baths ⋅ Jackson Square SubDv. ⋅ 33701 Zip Code
INVESTOR / RENOVATION OPPORTUNITY IN THE HEART OF ST. PETERSBURG! Bring your vision to this 2-bedroom, 1-bath home offering over 1,000 square feet of living space and significant potential for the right buyer. Located in the rapidly evolving Bartlett Park area, this property presents an exciting opportunity for investors, flippers, or buyers looking to renovate and create value. The location is a major highlight—just minutes from Downtown St. Pete, Tropicana Field and the Gas Plant District, with easy access to Central Avenue, USF St. Petersburg, the waterfront, restaurants, entertainment, and everything the city has to provide. With renovated homes in the surrounding area commanding significantly higher values, 781 16th Ave S offers an opportunity to capitalize on the spread between acquisition, renovation, and potential resale value. Whether you’re looking for your next flip, rental property, or renovation project, the combination of location, square footage, and neighborhood feel makes this one worth a closer look. Bring your contractor, run the numbers, and unlock the potential of this St. Pete investment opportunity.

781 16th Avenue S, St Petersburg
$329,000
2 Beds ⋅ 1 Baths ⋅ Jackson Square SubDv. ⋅ 33701 Zip Code
Virtually Staged. Presenting a charming 2-bedroom, 1-bathroom Craftsman home offering 816 square feet of elegantly appointed living space. Nestled along the picturesque historic brick-paved streets of the highly desirable Jackson Square subdivision, this residence beautifully balances classic character with functional design. The inviting interior features a dedicated dining room and a spacious, comfortable living area perfectly suited for hosting friends and family during the holidays. Two enclosed porches—situated at the front and rear of the home—provide versatile bonus spaces that can be enjoyed year-round. Step through the rear porch to discover a generously sized, fully fenced backyard offering incredible indoor-outdoor living, complemented by a dedicated rear parking pad. This property is virtually maintenance-free... Roof (2018) Hurricane windows and doors (2024) New Plumbing and sewer drain line (2026) New electrical (2026) newer HVAC, property maintenance package included, and fully renovated in 2021. This is St. Pete living done right; blocks away from the coastal waterfront, blocks away from downtown, and easy access to the beach, schedule your private showing today!

789 16th Avenue S, St Petersburg
$300,000
2 Beds ⋅ 2 Baths ⋅ Jackson Square SubDv. ⋅ 33701 Zip Code
Welcome to 711 16th Ave S — a beautifully renovated 3-bedroom, 2-bathroom bungalow for sale in St. Petersburg, FL, where 1940s historic character meets modern, move-in-ready finishes. Homes like this — updated, charming, and minutes from Downtown St. Pete — don't come along often. Step inside 1,042 square feet of bright, thoughtfully designed living space. The open floor plan connects the main living areas seamlessly, making the home feel larger than its footprint and perfect for both everyday living and entertaining. The stylishly updated kitchen [add specifics: shaker cabinets, quartz counters, stainless appliances] anchors the heart of the home, while both bathrooms have been tastefully refreshed with modern fixtures and finishes. Three true bedrooms give you flexibility for guests, a home office, or a nursery, and the smart layout makes every square foot count. Major systems bring peace of mind too — the roof was replaced in 2020. Outside, the yard offers room to relax, garden, or entertain under the Florida sun — and the rare detached garage is a standout, ideal for secure parking, storage, a workshop, or future studio potential. Garages at this price point in St. Petersburg are genuinely hard to find. The location seals the deal. In under 5 minutes you're at Downtown St. Petersburg's waterfront — the St. Pete Pier, world-class museums like the Dalí, and the city's award-winning dining, coffee, and craft-brewery scene along Central Avenue. Sports fans, arts lovers, and beachgoers are all covered: quick access to I-275 puts Tampa, St. Pete Beach, and the Gulf of Mexico's amazing beaches within an easy drive, and Tampa International Airport is about 30 minutes away. Whether you're searching for your first home, a low-maintenance Downtown St. Pete crash pad, or a turnkey income/investment property in one of Florida's fastest-growing cities, this renovated St. Petersburg bungalow checks every box. Historic charm, modern updates, unbeatable location — schedule your private showing today! The location is the kicker: less than 5 minutes to Downtown St. Petersburg's waterfront, the Pier, museums, and the city's award-winning dining and craft-brewery scene. Quick access to I-275 puts Tampa and the Gulf beaches within an easy drive. Historic charm, modern updates! Schedule your private showing today!

711 16th Avenue S, St Petersburg
$575,000
2 Beds ⋅ 1 Baths ⋅ Jackson Square SubDv. ⋅ 33701 Zip Code
Wonderful Opportunity in Prime Location of Highly Desired Bartlett Park neighborhood just south of Downtown St. Pete and Historic Roser Park! The 1936 two-bedroom, one-bath home is just minutes from the downtown restaurants, shops, museums, waterfront, and so much more. This charming bungalow features a completely fenced-in yard which includes detached one-car garage, ample enough space to store an RV and/or Boat and easy alley access with a large gate opening to the yard. The location is absolutely ideal with NO FLOOD INSURANCE NEEDED AND WAS COMPLETELY UNDAMAGED FROM THE HURRICANES! USF St. Petersburg, HCA Hospital, and Bayfront Medical Center only a few blocks away, if you want to hang out at a heated pool the North Shore Aquatic Center is just a short 10-minute bike ride away. The world renowned Gulf beaches (15-20 minutes away), Tampa International Airport (25-30 minutes away), and plenty of public golf courses are throughout the area as well as the sailing community of St Pete Yacht Club & the Marina only a stones throw away. Sports facilities are also comfortably close by with the MLB Rays Tropicana Field and Rowdies soccer. Don't miss out on this amazing opportunity to call St Petersburg Home and schedule your showing today!

860 16th Avenue S, St Petersburg
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