Homes in Gillespie Park

$2,399,000
4 Beds ⋅ 5 Baths ⋅ Central Park SubDv. ⋅ 34236 Zip Code ⋅ A4705541 MLS ⋅ Active Status
Discover modern downtown living in the heart of Gillespie Park, where this brand-new single-family home offers a rare combination of contemporary design, generous living space and exceptional walkability just moments from Downtown Sarasota and the Rosemary District. The property offers 4 bedrooms in total, including 3 bedrooms plus a dedicated office in the main residence and a private 1-bedroom, 1-bathroom attached apartment. Designed for everyday living and entertaining, the main residence features a spacious open floor plan filled with natural light. Engineered hardwood flooring, PGT impact-rated windows and doors, soaring ceilings and thoughtfully selected finishes complement the home’s clean, contemporary design. At the heart of the home, the kitchen features Thermador appliances, generous workspace and a seamless connection to the main living and dining areas. One of the home’s most distinctive features is the approximately 600-square-foot attached apartment complete with its own private entrance, bedroom, bathroom, living room and kitchen. Ideal for guests, multigenerational living, a private home office or potential rental income, this separate living space provides exceptional flexibility while preserving the privacy of the main residence. An attached 2-car garage and additional covered parking provide everyday convenience rarely found this close to downtown. Just outside your door, enjoy easy access to the Rosemary District, Downtown Sarasota’s restaurants, boutiques and arts scene, the Sarasota bayfront and the area’s renowned Gulf beaches. Whether heading out for morning coffee, dinner downtown or a day at the beach, this brand-new home places the best of the Sarasota lifestyle within easy reach.

1675 5th Street, Downtown
$450,000
3 Beds ⋅ 2 Baths ⋅ Petroutsa Brothers Sub SubDv. ⋅ 34236 Zip Code ⋅ A4703716 MLS ⋅ Active Status
Welcome to Gillespie Park, one of Sarasota’s most distinctive historic neighborhoods, where established residential streets meet the energy, growth, and convenience of Downtown Sarasota. This 5,000-square-foot parcel with DTE zoning is being offered for its land value and the existing structure is being conveyed in its present As-Is condition. A great opportunity for a developer, builder, investor, or long-term landholder seeking a strategically positioned site near the heart of the city. Downtown Edge zoning is intended to provide a transition between Sarasota’s downtown core and surrounding neighborhoods while accommodating a mix of residential and compatible nonresidential uses. The property is also located within a zoning district eligible for the City of Sarasota’s Downtown Attainable Housing Density Bonus Program, which may provide additional density opportunities for qualifying developments, subject to City requirements, approvals, development standards, and site-specific feasibility. The location adds another layer to the opportunity. Gillespie Park combines historic neighborhood character with newer construction, redevelopment, green space, and convenient access to the many destinations surrounding Downtown Sarasota. Restaurants, coffee shops, entertainment, cultural venues, the Rosemary District, Main Street, The Bay, and Sarasota’s waterfront are nearby, while St. Armands Circle, Lido Key, and the Gulf beaches are within easy reach. For those looking beyond the existing improvements and toward the potential of the site itself, this is an opportunity to control DTE-zoned land within Sarasota’s downtown area and explore what may be possible today or in the future. Buyers and developers are encouraged to independently verify zoning, allowable uses, density, setbacks, demolition requirements, utilities, and eligibility for applicable development incentives with the City of Sarasota.

919 Goodrich Avenue, Downtown
$479,900
6 Beds ⋅ 5 Baths ⋅ Petroutsa Brothers Sub SubDv. ⋅ 34236 Zip Code ⋅ O6433142 MLS ⋅ Active Status
Gillespie Park Triplex Investment Opportunity! Located in the highly sought-after Gillespie Park area of Sarasota, this 1,983 SF triplex offers an excellent opportunity to renovate and reposition a multi-unit property in one of Sarasota's desirable in-town locations. The property features three separate units with a total of 6 bedrooms and 3 baths, each having a Kitchen with living/dining combination, providing flexible income-producing potential. Zoned DTE, the property offers a variety of possibilities for an investor or owner looking to create value in a sought-after Sarasota location. Conveniently located near downtown Sarasota, Gillespie Park, restaurants, shopping, entertainment, and the area's beautiful beaches. With its desirable location, three-unit configuration, and redevelopment potential, this property is an excellent opportunity to bring new life to a multi-family asset in an established Sarasota neighborhood. Buyer to verify all zoning, dimensions, uses, and redevelopment possibilities with the appropriate governing authorities. All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyer advised to verify.

1672 10th Street, North Sarasota
$1,595,000
5 Beds ⋅ 5 Baths ⋅ Gillespie Park Sub SubDv. ⋅ 34236 Zip Code ⋅ A4702560 MLS ⋅ Active Status
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, Downtown
$390,000
Central Park SubDv. ⋅ 34236 Zip Code ⋅ N6145316 MLS ⋅ Active Status
INQUIRE ABOUT SELLER FINANCING OPTIONS. Prime 5,042 sq. ft. corner lot in downtown Sarasota, zoned DTN (Downtown Neighborhood), offering an excellent opportunity to build in one of Sarasota’s established downtown neighborhoods. The 50' x 101' lot has public water and sewer available, along with electricity and cable, making it well positioned for future development. DTN zoning supports residential development and other neighborhood-compatible uses, with the specific building type, density, setbacks, height, parking, and other development requirements subject to current City of Sarasota regulations and site-specific review. The location puts you close to the best of downtown Sarasota, with a vibrant mix of restaurants, cafés, boutique shopping, galleries, entertainment, and cultural venues nearby. Gillespie Park is just a short distance away, offering walking trails, tennis and basketball courts, a playground, fitness areas, a pond, and a dog park, providing convenient outdoor recreation in an established downtown neighborhood. The property also offers convenient access to Sarasota’s renowned Gulf Coast beaches, including Lido Key and Siesta Key, as well as St. Armands Circle for shopping and dining. With downtown amenities, parks, waterfront recreation, arts and culture, restaurants, and beaches all within easy reach, this corner lot presents an attractive opportunity to create a new residence or investment property in a highly desirable Sarasota location.

449 N Osprey Avenue, Downtown
$1,849,000
4 Beds ⋅ 5 Baths ⋅ Schindler Sub SubDv. ⋅ 34236 Zip Code ⋅ A4700509 MLS ⋅ Active Status
The Gillespie Park Casa del Sol Is Finally on the Market! Nestled beneath a canopy of majestic oaks in Sarasota's beloved and historic Gillespie Park, Casa del Sol is an extraordinary Mediterranean-inspired estate where timeless architecture, modern luxury, and resort-style living come together just moments from the heart of downtown. Built in 2007 with solid masonry construction, this remarkable property offers 3,338 total square feet, including a 2,854-square-foot main residence, a beautifully appointed 484-square-foot detached studio casita resting above the spacious detached 2 car garage w/covered carport. This 4 bedrooms, 4.5 bathrooms, is offered for well under $2 million. Designed to capture the romance of an authentic Mediterranean villa, the home showcases imported Colombian roof tiles, handcrafted Colombian brick pavers, rich hardwood flooring, elegant French doors, a chef's kitchen with stainless steel appliances, a gas range and fireplace, dual-zone HVAC, a tankless water heater, and a convenient second-floor laundry room. Every detail reflects exceptional craftsmanship while blending seamlessly with today's modern lifestyle. Step outside to your own private tropical retreat, where lush landscaping, a sparkling heated pool (with fountain water feature), and a newly installed privacy fence create an atmosphere of serenity and effortless entertaining. The detached studio casita offers outstanding flexibility as a luxurious guest suite, executive office, fitness studio, creative space, or income-producing accommodation. It is separately metered for convenience. Just a 2 min walk from the 10-acre John Hamilton Gillespie Park and a 2 minute drive (or short walk or bike ride) from Downtown Main Street and Sarasota's award-winning restaurants, boutiques, theaters, galleries, waterfront, and renowned Farmers Market, Casa del Sol places the very best of Sarasota at your doorstep. Located within the desirable Downtown Neighborhood (DTN) zoning district allowing one-week minimum short-term rentals, the property presents a rare opportunity as a primary residence, seasonal escape, or exceptional investment. Rarely does a home provide this level of architectural distinction, walkable downtown convenience, investment flexibility, and resort-inspired living. Casa del Sol is finally on the market, offering an extraordinary opportunity to experience one of Sarasota's most coveted lifestyles.

1719 7th Street, North Sarasota
$1,395,000
2 Beds ⋅ 2 Baths ⋅ Plat Of Sarasota SubDv. ⋅ 34236 Zip Code ⋅ A4700305 MLS ⋅ Active Status ⋅ The Demarcay BLDG.
Experience refined downtown living from the 15th floor of The DeMarcay, one of Sarasota's premier luxury condominium residences. Perfectly positioned in the heart of downtown, this exceptional two-bedroom, two-bath residence offers the ultimate lifestyle, placing world-class dining, boutique shopping, art galleries, theaters, the Sarasota Opera, Whole Foods, the Saturday Farmers Market and the city's vibrant cultural scene just outside your door. Just a short stroll away, Sarasota Bay, Marina Jack, Bayfront Park and O'Leary's Tiki Bar provide endless opportunities to enjoy waterfront dining, boating and spectacular Gulf Coast sunsets. Inside, the residence showcases sophisticated contemporary design with an open-concept floor plan highlighted by a stunning chef's kitchen featuring quartz countertops, a waterfall island and seamless flow into the dining and living areas. Floor-to-ceiling windows and the private terrace capture beautiful city views along with a picturesque peek of Sarasota Bay. A custom-built entertainment wall and elegant dry bar with wine refrigeration create the perfect setting for entertaining, while porcelain tile flooring, designer lighting and premium finishes elevate every space. The spacious primary suite offers a custom walk-in closet and a beautifully appointed spa-inspired bath. Residents of The DeMarcay enjoy an exceptional luxury lifestyle with concierge service, valet parking, the secure Butterfly entry system, a state-of-the-art fitness center, owner's storage and a spectacular rooftop amenity level featuring a resort-style pool, outdoor kitchen, club room and panoramic views of Sarasota's skyline and bay. This is a rare opportunity to enjoy sophisticated, maintenance-free living with the very best of downtown Sarasota just moments from your front door.

33 S Palm Avenue Unit 1503, Sarasota
$625,000
4 Beds ⋅ 2 Baths ⋅ Petroutsa Brothers Sub SubDv. ⋅ 34236 Zip Code ⋅ A4695133 MLS ⋅ Active Status
Virtually Staged. Welcome to the heart of Sarasota living in the desirable Gillespie Park neighborhood! This spacious 4-bedroom, 2-bath residence offers over 1,800 square feet of comfortable living space with an open floor plan, soaring ceilings, and durable tile flooring throughout. Built in 1996 and thoughtfully updated with a new AC system and new windows, the home combines modern efficiency with everyday functionality. The enclosed garage provides exceptional flexibility and can serve as a bonus room, home office, den, fitness space, or potential in-law suite opportunity. Step outside to your own private backyard sanctuary featuring a fully fenced yard—perfect for entertaining, gardening, pets, or simply enjoying Florida’s outdoor lifestyle. Located within Sarasota city limits, this property offers excellent short-term rental potential and places you just minutes from vibrant downtown Sarasota, world-renowned beaches, SRQ Airport, shopping, dining, arts, and entertainment. Residents of Gillespie Park enjoy access to the community’s beautiful 10-acre park featuring tennis courts, walking paths, a scenic pond, playground, and expansive green space. Whether you’re searching for a primary residence, investment property, or seasonal retreat, this home delivers the best of Sarasota living with location, versatility, and lifestyle all in one exceptional package.

1649 8th Street, North Sarasota
$650,000
Schindler Sub SubDv. ⋅ 34236 Zip Code ⋅ A4695998 MLS ⋅ Active Status
Rare opportunity to acquire a 9,200 SF double lot in one of Downtown Sarasota’s most desirable and rapidly evolving neighborhoods. Located just steps from the 10-acre Gillespie Park, this property offers exceptional potential in an area experiencing significant investment and redevelopment. Residents enjoy easy access to tennis and basketball courts, a scenic pond, dog park, fitness trail, playground, and shaded walking paths beneath majestic oak trees. The property is within walking distance of Downtown Sarasota’s restaurants, galleries, shopping, and entertainment venues, and only 0.7 miles from Sarasota Bay and The Bay, the city’s signature waterfront park. With no HOA, no deed restrictions, DTN (Downtown Neighborhood) zoning, and potential benefits under Florida’s Live Local Act, this property offers outstanding flexibility for a variety of residential development opportunities. The location provides convenient access to Sarasota’s vibrant cultural scene, including the Westcoast Black Theatre Troupe, Sarasota Orchestra, Bayfront Marina, and the city’s renowned arts and dining districts. Whether you are looking to build now or secure land in one of Sarasota’s most dynamic growth corridors, this oversized double lot presents a rare opportunity in the heart of Downtown Sarasota. Adjacent home is also available for purchase. Combined, the properties would create four contiguous lots totaling approximately 19,200 SF (0.44 acres), presenting an exceptional assemblage opportunity for future development.

1721 8th Street, North Sarasota
$2,195,000
3 Beds ⋅ 4 Baths ⋅ Demarcay SubDv. ⋅ 34236 Zip Code ⋅ A4695811 MLS ⋅ Active Status ⋅ Demarcay BLDG.
Welcome to The DeMarcay, where luxury, convenience, and sophistication come together in one of the city's newest premier high-rise residences. Rarely available and highly sought after, this spacious 3-bedroom, 3.5-bathroom floor plan offers the flexibility and comfort of a single-family home with all the advantages of maintenance-free condominium living. Designed for effortless everyday living, the open-concept layout features expansive living spaces, soaring ceilings, floor-to-ceiling windows, and designer finishes throughout. One of the residence's most captivating features is its breathtaking panoramic views of Sarasota Bay, providing a front-row seat to spectacular year-round sunsets and the city's vibrant waterfront fireworks displays. Whether relaxing with your morning coffee or entertaining guests in the evening, the ever-changing views create an unforgettable backdrop. The gourmet kitchen is beautifully appointed with premium appliances, custom cabinetry, and elegant stone countertops, creating the perfect setting for entertaining guests or enjoying a quiet evening at home. Each bedroom features its own private en-suite bathroom, providing comfort and privacy for family and visitors alike. The luxurious primary suite serves as a private retreat with spa-inspired finishes, generous closet space, and a serene atmosphere designed for relaxation. Leave behind the maintenance of a traditional home and embrace a lock-and-leave lifestyle with exceptional amenities at your fingertips. Residents enjoy a stunning rooftop pool with panoramic city and bay views, a state-of-the-art fitness center, rooftop entertaining spaces, outdoor lounges, and personalized services designed to make everyday living effortless. Ideally located in the heart of downtown Sarasota, you're just steps from fine dining, boutique shopping, theaters, galleries, Sarasota Bay, Marina Jack, and the city's vibrant cultural scene. Whether you're seeking a full-time residence or seasonal retreat, this exceptional 3-bedroom residence offers a rare opportunity to enjoy spacious downtown living without compromise. Luxury, convenience, panoramic bay views, and a coveted three-bedroom layout—The DeMarcay delivers a truly elevated downtown Sarasota lifestyle. Book your private showing today!

33 S Palm Avenue Unit 901, Sarasota
$750,000
3 Beds ⋅ 2 Baths ⋅ Schindler Sub SubDv. ⋅ 34236 Zip Code ⋅ A4695550 MLS ⋅ Active Status ⋅ 1743 BLDG.
Rare opportunity to own a beautifully restored vintage home with a detached art studio on a 10,000 SF double lot in one of Downtown Sarasota’s most desirable and evolving neighborhoods. Extensively renovated in 2000, the home features updated plumbing, electrical, windows, Hardie board siding, and numerous additional improvements, resulting in an effective year built of 2020. The property blends timeless character with modern functionality while offering exceptional flexibility and value. Just steps from the 10-acre Gillespie Park, residents enjoy access to tennis and basketball courts, a scenic pond, dog park, fitness trail, playground, and shaded walking paths beneath majestic oak trees. The location is within walking distance of Downtown Sarasota’s restaurants, galleries, shopping, and entertainment venues, and only 0.7 miles from Sarasota Bay and The Bay, the city’s signature waterfront park. With no HOA, no deed restrictions, DTN (Downtown Neighborhood) zoning, and potential benefits under Florida’s Live Local Act, this property offers unique opportunities for homeowners, investors, and entrepreneurs alike. The detached art studio provides an ideal live-work setting for artists, creatives, remote professionals, or anyone seeking dedicated workspace separate from the main residence. Enjoy convenient access to Sarasota’s vibrant cultural scene, including the Westcoast Black Theatre Troupe, Sarasota Orchestra, Bayfront Marina, and the city’s renowned arts, dining, and entertainment districts. Whether you're seeking a primary residence, seasonal retreat, live-work property, or investment opportunity, this home offers a rare combination of historic charm, modern upgrades, generous outdoor space, and an exceptional downtown location. Adjacent lot also available for purchase. Combined, the properties would create four contiguous lots totaling approximately 19,200 SF (0.44 acres), presenting a rare opportunity for additional space or future development in the heart of Downtown Sarasota.

1743 8th Street, North Sarasota
$1,995,000
5 Beds ⋅ 4 Baths ⋅ Schindler Sub SubDv. ⋅ 34236 Zip Code ⋅ A4693200 MLS ⋅ Active Status
Under Construction. Introducing 1738 7th Street, a brand-new modern luxury residence offering 3,337 square feet of refined coastal living on a 42 x 130 lot in downtown Sarasota's Gillespie Park neighborhood. This thoughtfully designed 5-bedroom, 3.5-bath home delivers the privacy of a standalone property with the architectural cohesion of a boutique collection. Behind a premium plaster facade and 8-foot hand-crafted black iron impact-rated entry doors, the home opens to an expansive open-concept main level anchored by soaring 21-foot ceilings. Floor-to-ceiling windows frame the private outdoor living space and flood the interior with natural light. The professional chef's kitchen features a 48-inch Thor gas range with six sealed burners, integrated griddle, and dual convection ovens. A commanding center island anchors the space with a Karran stainless undermount sink, custom-painted bespoke cabinetry, and signature matte black hardware. The adjacent butler's pantry includes an oversized walk-in, 64-inch Electrolux refrigerator and freezer column suite, and built-in microwave. A dedicated beverage gallery with dual-zone wine refrigeration and high-capacity ice maker rounds out the hospitality wing. The first-floor primary suite serves as a private sanctuary overlooking a hedged-in patio, with an adjoining sitting room or home office, a spa-inspired bath with large-format marble tile, an architectural glass-enclosed wet room with deep soaking tub and multi-head shower system, polished nickel double vanity, and a massive custom walk-in closet. Upstairs, 10-foot ceilings continue across four generously proportioned guest bedrooms with high-profile windows. Two oversized Jack-and-Jill marble bathrooms feature floor-to-ceiling showers, custom storage niches, double vanities, and private water closets. A detached two-car garage delivers secure covered off-street parking, a premium and increasingly rare feature in the downtown Sarasota core. Structural provisions are in place for a future ADU above the garage, offering flexibility for a guest suite, studio, or additional living space. The outdoor living space features an expansive large-format paver patio and low-maintenance turf lawn. The backyard is designed to accommodate a future private pool addition, allowing buyers to customize to their preference. Hedged privacy screening frames the space. Additional highlights include a designer powder room, first-floor laundry, 2-zone HVAC, 200-amp electrical, designer LED recessed lighting, 8-foot black iron French doors, weathershed wide-plank flooring, and Benjamin Moore Chantilly Lace paint with Revere Pewter cabinetry. Exterior touches include a crushed shell driveway. Est. completion September 30, 2026. Renderings are illustrative; actual construction may vary.

1738 7th Street, North Sarasota
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Gillespie Park, Sarasota, FL: Historic Charm and Urban Oasis

Explore the unique blend of historic charm and urban oasis in Gillespie Park, a distinct neighborhood in Sarasota, Florida. Nestled just north of downtown Sarasota, Gillespie Park offers residents a serene escape with tree-lined streets, historic homes, and a central park that serves as a hub for community engagement. Join us as we delve into the character and appeal of Gillespie Park.

 

Key Features:

Gillespie Park:

The neighborhood's namesake, Gillespie Park, is a green oasis at the heart of the community. Residents can enjoy walking trails, open spaces, and community events in this picturesque park setting.

Historic Architecture:

Gillespie Park is known for its historic architecture, featuring a mix of charming cottages and bungalows. The well-preserved homes contribute to the neighborhood's character and offer a glimpse into Sarasota's past.

Proximity to Downtown Sarasota:

Situated just north of downtown Sarasota, Gillespie Park provides residents with easy access to the city's cultural amenities, dining, and entertainment options. The urban proximity enhances the neighborhood's overall appeal.

Cultural and Arts District:

Gillespie Park is part of Sarasota's cultural and arts district, allowing residents to immerse themselves in the vibrant arts scene. Galleries, theaters, and cultural events add to the neighborhood's dynamic atmosphere.

 

 

Real Estate Opportunities:

Explore the real estate offerings in Gillespie Park, featuring historic homes and residences with unique architectural character. The neighborhood's real estate landscape caters to individuals who appreciate the charm of historic properties.

 

Why Choose Gillespie Park:

Tranquil Urban Oasis:

Gillespie Park offers a tranquil urban oasis with its central park, providing residents with a serene retreat amidst the hustle and bustle of the city.

Historic Homes and Architecture:

The neighborhood's historic homes showcase unique architectural styles, allowing residents to live amidst the charm of the past. Gillespie Park is a testament to Sarasota's rich architectural heritage.

Close Proximity to Downtown:

The neighborhood's proximity to downtown Sarasota ensures that residents can easily access cultural amenities, restaurants, and entertainment options. The urban convenience enhances the overall lifestyle in Gillespie Park.

Community Engagement:

Gillespie Park fosters community engagement through its central park and events. Residents have opportunities to connect with neighbors, participate in local activities, and contribute to the close-knit community spirit.

 

 

Gillespie Park invites you to experience the allure of historic charm and urban serenity in Sarasota. Connect with our real estate experts today to explore the diverse homes and lifestyle opportunities that await you in this distinctive neighborhood. Gillespie Park is not just a location; it's a community where residents can enjoy the beauty of a central park, the character of historic homes, and the convenience of urban living in a tranquil oasis.