Gillespie Park Sub Real Estate

Gillespie Park Sub Real Estate

Welcome to Gillespie Park Subdivision, a hidden gem nestled in the heart of Sarasota, Florida. This vibrant community is not just a place to live; it’s a lifestyle enriched by the charm of local culture, beautiful landscapes, and a strong sense of community.

Gillespie Park Sub is characterized by its picturesque tree-lined streets and an array of thoughtfully designed homes that cater to various tastes and budgets. Whether you’re seeking a cozy bungalow or a modern family home, this subdivision offers diverse architectural styles that blend seamlessly with the surrounding environment. The community is known for its friendly neighbors and welcoming atmosphere, making it an ideal place for families, retirees, and young professionals alike.

One of the standout features of Gillespie Park Sub is its proximity to the lush Gillespie Park itself, which provides residents with ample opportunities for outdoor recreation. Enjoy leisurely strolls, picnics, or weekend gatherings under the shade of ancient oaks. The park also hosts various community events, fostering a tight-knit neighborhood spirit.

Convenience is key in Gillespie Park Sub. Located just minutes away from Sarasota’s vibrant downtown area, residents have easy access to an array of dining, shopping, and entertainment options. The nearby beaches, renowned for their pristine sands and crystal-clear waters, are perfect for sunbathing, swimming, or simply unwinding.

With its charming homes, lush green spaces, and a strong sense of community, Gillespie Park Subdivision is a perfect place to call home. Discover the lifestyle you’ve been dreaming of in this delightful Sarasota neighborhood!

Newest Listings in Gillespie Park Sub

$345,000
2 Beds ⋅ 1 Baths ⋅ Gillespie Park Sub SubDv. ⋅ 34236 Zip Code
Rare Gillespie Park infill lot opportunity! 5,040 SF just steps from Downtown Sarasota in one of the city's most walkable neighborhoods (Walk Score 87). Existing 1941 cottage sold as-is — an ideal teardown/redevelopment infill lot for a builder, developer, or end-user ready to design a custom modern home. Surrounded by new construction, minutes to the Rosemary District, restaurants, and the Sarasota bayfront. Land value — bring your builder! Buyer to verify zoning/FAR with the City of Sarasota.

614 N Osprey Avenue, Sarasota
$999,000
5 Beds ⋅ 4 Baths ⋅ Gillespie Park Sub SubDv. ⋅ 34237 Zip Code
Three renovated units, one corner parcel, four blocks from Main Street. A fully occupied Sarasota triplex producing $7,200 per month, or $86,400 annually, against a $999,000 asking price. That is an 8.65% gross yield and a basis of $333,000 per door. Every unit has been rebuilt inside. Large-format marble-look porcelain tile runs wall to wall through all three, with no carpet anywhere in the building. Walls and ceilings are crisp white under flush-mount LED fixtures in every room. Kitchens carry light flat-panel cabinetry, and stainless appliances, with stacked laundry inside the unit rather than a shared machine down the hall. Bathrooms are white vanities, chrome fittings and framed mirrors over the same tile. The finish package is deliberately consistent across all three units, and that consistency is what makes it turnkey: one material palette, one maintenance standard, and no unit sitting in line for work before it can lease. The mix spans three price points. A three-bedroom, two-bath at $3,800. A two-bedroom, one-bath at $1,900. A studio at $1,500. All three are occupied. The building is single-story concrete block on a slab under a shingle roof, with central air, public water and public sewer, and off-street parking for ten. Three water meters and three electric meters measure consumption per unit. The parcel sits in Flood Zone X. Between masonry construction and Flood Zone X, the two variables that drive Florida insurance both point the same direction. Ownership is fee simple with no HOA, no condominium association and no CDD fee. Two levers sit on top of the in-place rent. The first is vacation rental. The City of Sarasota extended its vacation rental ordinance to the Downtown Neighborhood zone district in March 2024, and this parcel falls inside it. Stays of seven nights or longer are permitted with a city certificate, which is a materially different revenue profile than a twelve-month lease in a location four blocks off Main Street. The second is the land. A 12,472 square foot corner site, zoned DTN and sitting under the City's Missing Middle Overlay, which can support density beyond the three units standing today where attainable-housing, design and permitting standards are satisfied. Nothing further is approved and any concept requires confirmation with the City, but the parcel carries a second thesis that a stabilized triplex elsewhere does not. Renovated, occupied, individually metered, insurable, and sitting on urban ground with room to grow. Income now, optionality later.

431 N East Avenue, Sarasota
$1,595,000
5 Beds ⋅ 5 Baths ⋅ Gillespie Park Sub SubDv. ⋅ 34236 Zip Code
LOCATION, LOCATION, LOCATION! If you are seeking a premier home which is steps from the dining, culture, boutiques, and waterfront recreation of Downtown Sarasota/Main St, The Bay Park, the Rosemary District, Five Points Park, and Gillespie Park, this is the one! This beautifully renovated, Key West–inspired 5-bedroom, 2938 sf pool home welcomes you with a magnificent oak tree and gorgeous tropical landscaping. Inside, the chef-owner’s kitchen is a culinary dream complete with a professional Forno gas range, custom soft-close cabinetry, and sleek quartz countertops. High-end finishes elevate the open living areas, including rich hardwood floors, an electric fireplace, and a custom temperature-controlled wine room. A flexible downstairs bonus area with a half bath and closet can easily convert to a luxurious primary suite/5th bedroom. A 600 sf guest apartment, The Pineapple Loft, is consistently ranked 5 stars on Airbnb and features a vaulted ceiling, full kitchen, induction cooking, laundry, and a private balcony— fully qualifying for high-demand weekly rentals! The exterior features a screened courtyard lanai and a heated pool with a waterfall, while the local 10-acre park provides tennis, pickleball, walking trails, and a lively neighborhood scene. Don't miss this perfect blend of historic character, modern luxury, and ultimate flexibility in an incredible location.

1685 6th Street, Sarasota
$314,600
3 Beds ⋅ 1 Baths ⋅ Gillespie Park Sub SubDv. ⋅ 34234 Zip Code
Welcome to 2509 Dixie Ave, Sarasota, FL 34234 — an exciting opportunity to secure a partially renovated 3-bedroom, 1-bath home before the final touches are complete. Whether you are a first-time homebuyer, investor, or buyer searching for a property with flexible living or income-producing potential, this home offers value, location, and opportunity. Renovations are already underway, making this the perfect chance for a buyer to get in early and secure the property before completion. Updates in progress include a new roof, updated A/C system, updated electrical, new flooring, updated windows, new kitchen cabinets and countertops, stainless steel appliances, fresh interior and exterior paint, and improvements to the front porch. Additional finishing work is still being completed. This property offers a functional layout with three bedrooms and strong potential as a primary residence, rental property, or shared housing opportunity, subject to local regulations and buyer verification. Buyers looking for a home with upside and future value will appreciate the ability to purchase while improvements are still in progress. Located just minutes from Downtown Sarasota with convenient access to US-41 and US-301, this home is close to shopping, dining, employment centers, and everyday conveniences. Sarasota’s city and Gulf beaches are less than 15 minutes away, adding even more appeal to this well-located property. Opportunities like this do not last long. Get in now, secure your home early, and take advantage of the chance to own a newly updated property before renovations are fully complete. Schedule your showing today and see the potential for yourself.

2509 Dixie Avenue, Sarasota
$1,100,000
4 Beds ⋅ 3 Baths ⋅ Gillespie Park Sub SubDv. ⋅ 34236 Zip Code
Under Construction. **New Construction Luxury Half Duplex in Gillespie Park – Walkable to Downtown Sarasota** Discover a rare opportunity to own a newly constructed luxury residence in Sarasota's highly sought-after Historic Gillespie Park neighborhood. This three-story, all-block half duplex offers more than 2,500 square feet of thoughtfully designed living space, featuring 4 bedrooms, 3 bathrooms, a spacious third-floor flex room, and an expansive rooftop-style balcony ideal for entertaining, working remotely, or enjoying Sarasota's year-round sunshine. Currently in the drywall phase of construction, this home presents a unique chance for buyers to personalize interior finishes, fixtures, and materials before completion. Major infrastructure is already in place, including electrical, plumbing, hurricane-rated PGT impact windows, and a durable EPDM roofing system. The versatile third-floor space can serve as a home office, media room, game room, art studio, fitness area, or private retreat. Located just four homes from Gillespie Park and only blocks from Downtown Sarasota, residents will enjoy convenient access to award-winning restaurants, boutique shopping, cultural venues, theaters, farmers markets, waterfront attractions, and the vibrant downtown lifestyle that makes Sarasota one of Florida's most desirable places to live. Priced at $1.1 million, this property offers the rare combination of new construction, customizable finishes, modern hurricane-resistant construction, and an unbeatable walkable location near downtown Sarasota. **Important:** This offering is for the west-side residence only. The property is currently situated on a single parcel. Sale is contingent upon final municipal approval, recording of the lot split, and issuance of a separate Parcel ID prior to closing. Schedule your private tour today and secure one of the most unique new construction opportunities currently available in Gillespie Park and Downtown Sarasota.

1755 8th Street Unit West, Sarasota
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