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You are here: Home / Gillespie Park Homes for Sale in Sarasota, FL

Gillespie Park Homes for Sale in Sarasota, FL

Located just blocks from Downtown Sarasota, Gillespie Park is one of the city’s most distinctive and historically rich neighborhoods. With roots dating back to the early 1920s, this established community blends architectural character, cultural depth, and walkable urban living in a way few Sarasota neighborhoods can match.

The neighborhood is anchored by Gillespie Park itself, a public green space named after Sarasota’s first mayor. The park serves as both a recreational and social focal point, helping preserve the sense of community that has defined Gillespie Park for generations. Mature trees, brick-lined streets, and an eclectic mix of homes give the area a timeless, lived-in feel.

Homes for sale in Gillespie Park reflect a wide range of architectural styles. Buyers will find Old Florida cottages, Spanish Colonial residences, French Country homes, and Caribbean-inspired designs alongside newer construction featuring Modernist and Mediterranean influences. This diversity is part of what makes the neighborhood so appealing to homeowners and investors alike.

Gillespie Park’s close proximity to downtown has helped support long-term property value growth. The neighborhood appeals to full-time residents, second-home buyers, and investors looking for character-rich properties near Sarasota’s cultural and employment centers. New construction and thoughtful renovations continue to complement the area’s historic charm without overpowering it.

Daily life in Gillespie Park is centered on convenience and lifestyle. Residents enjoy easy access to museums, theaters, art galleries, restaurants, and cafes, all within walking or biking distance. Beaches are typically about a ten-minute drive away, making it easy to balance urban living with Sarasota’s coastal lifestyle.

Gillespie Park Sarasota Neighborhood Gallery

Gillespie Park Sarasota Florida Homes for Sale
Gillespie Park in Sarasota Playground

Homes for Sale at Gillespie Park in Sarasota

510 N OSPREY AVENUE SARASOTA FL 34236
Open House Sat, Feb 28, 1 PM
1 / 46
$1,097,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,354
SQFT
510 N OSPREY AVENUE
SARASOTA, FL 34236
INWOOD PARK FIRST ADD Subdivision
1923 5TH STREET SARASOTA FL 34236
New Listing - a week on site
1 / 25
$1,250,000
Land For Sale
Active
0.24
ACRES
SARASOTA
COUNTY
1923 5TH STREET
SARASOTA, FL 34236
INWOOD PARK FIRST ADD Subdivision
1862 6TH STREET SARASOTA FL 34236
New Listing - 2 weeks on site
1 / 41
$799,000
Triplex For Sale
Active
6
TOTAL BATHS
1,419
SQFT
1862 6TH STREET
SARASOTA, FL 34236
INWOOD PARK FIRST ADDITION Subdivision
1862 6TH STREET SARASOTA FL 34236
New Listing - 2 weeks on site
1 / 42
$799,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
1,419
SQFT
1862 6TH STREET
SARASOTA, FL 34236
INWOOD PARK FIRST ADDITION Subdivision
1672 10TH STREET SARASOTA FL 34236
Real Estate Owned
1 / 24
$499,900
Residential For Sale
Active
6
BEDS
5
TOTAL BATHS
1,983
SQFT
1672 10TH STREET
SARASOTA, FL 34236
PETROUTSA BROTHERS SUB Subdivision
503 N OSPREY AVENUE SARASOTA FL 34236
Price Change - 4 weeks ago
1 / 30
$1,199,999
Residential Income For Sale
Active
6
BEDS
5
TOTAL BATHS
2,958
SQFT
503 N OSPREY AVENUE
SARASOTA, FL 34236
CENTRAL PARK SUB Subdivision
1755 8TH STREET SARASOTA FL 34236
1 / 7
$2,600,000
Single Family Residence For Sale
Active
9
BEDS
7
TOTAL BATHS
5,372
SQFT
1755 8TH STREET
SARASOTA, FL 34236
SCHINDLER SUB Subdivision
640 N OSPREY AVENUE SARASOTA FL 34236
Price Change - a week ago
1 / 84
$1,295,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
1,738
SQFT
640 N OSPREY AVENUE
SARASOTA, FL 34236
GILLESPIE PARK SUB Subdivision
417 N OSPREY AVENUE SARASOTA FL 34236
Price Change - 2 weeks ago
1 / 99
$1,995,000
Single Family Residence For Sale
Active
4
BEDS
5
TOTAL BATHS
3,154
SQFT
417 N OSPREY AVENUE
SARASOTA, FL 34236
CENTRAL PARK Subdivision
1685 6TH STREET SARASOTA FL 34236
1 / 60
$1,725,000
Single Family Residence For Sale
Active
4
BEDS
5
TOTAL BATHS
2,938
SQFT
1685 6TH STREET
SARASOTA, FL 34236
HALLS SUB JAMES S Subdivision
432 ADELIA AVENUE SARASOTA FL 34236
Price Change - 2 hours ago
1 / 47
$699,000
Quadruplex For Sale
Active
4
BEDS
4
TOTAL BATHS
2,063
SQFT
432 ADELIA AVENUE
SARASOTA, FL 34236
PRITCHARD FRANK Subdivision
1721 8TH STREET SARASOTA FL 34236
1 / 42
$1,400,000
Land For Sale
Active
0.44
ACRES
SARASOTA
COUNTY
1721 8TH STREET
SARASOTA, FL 34236
SCHINDLER SUB Subdivision
1755 7 TH STREET SARASOTA FL 34236
Price Change - 3 weeks ago
1 / 94
$2,100,000
Duplex For Sale
Active
4
BEDS
4
TOTAL BATHS
4,451
SQFT
1755 7 TH STREET
SARASOTA, FL 34236
SCHINDLER SUB Subdivision
1755 7TH STREET SARASOTA FL 34236
Price Change - 3 weeks ago
1 / 77
$2,100,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
4,451
SQFT
1755 7TH STREET
SARASOTA, FL 34236
SCHINDLER SUB Subdivision
941 N OSPREY AVENUE SARASOTA FL 34236
Short Sale
1 / 53
$495,000
Townhouse For Sale
Active
2
BEDS
2
TOTAL BATHS
1,550
SQFT
941 N OSPREY AVENUE
SARASOTA, FL 34236
SCHINDLER SUB Subdivision
1743 8TH STREET SARASOTA FL 34236
1 / 75
$1,400,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,400
SQFT
1743 8TH STREET
SARASOTA, FL 34236
SCHINDLERS Subdivision
624 GOODRICH AVENUE SARASOTA FL 34236
1 / 44
$1,600,000
Land For Sale
Active
0.24
ACRES
SARASOTA
COUNTY
624 GOODRICH AVENUE
SARASOTA, FL 34236
INWOOD PARK Subdivision
1705 6TH STREET SARASOTA FL 34236
1 / 43
$1,600,000
Land For Sale
Active
0.28
ACRES
SARASOTA
COUNTY
1705 6TH STREET
SARASOTA, FL 34236
INWOOD PARK Subdivision
1744 10TH STREET SARASOTA FL 34236
1 / 32
$625,000
Single Family Residence For Sale
Active
2
BEDS
1
TOTAL BATH
1,230
SQFT
1744 10TH STREET
SARASOTA, FL 34236
SCHINDLER SUB Subdivision
1744 10TH STREET SARASOTA FL 34236
1 / 32
$625,000
Land For Sale
Active
0.16
ACRES
SARASOTA
COUNTY
1744 10TH STREET
SARASOTA, FL 34236
SCHINDLER SUB Subdivision

Gillespie Park Sarasota FAQs

Where is Gillespie Park located?

Gillespie Park is located just north of Downtown Sarasota, within walking distance of the city’s cultural, dining, and entertainment districts.

Is Gillespie Park considered a historic neighborhood?

Yes. Gillespie Park dates back to the 1920s and is recognized as one of Sarasota’s most historically significant residential areas.

What types of homes are found in Gillespie Park?

The neighborhood features a mix of Old Florida cottages, Spanish Colonial homes, French Country designs, Caribbean influences, and newer modern or Mediterranean-style residences.

Is Gillespie Park popular with real estate investors?

Yes. Its proximity to downtown, architectural diversity, and ongoing revitalization make Gillespie Park attractive to both long-term homeowners and investors.

What amenities are nearby?

Residents are close to Gillespie Park itself, which includes tennis courts, picnic areas, a pond, walking paths, and gathering spaces, along with downtown museums, theaters, and restaurants.

How far is Gillespie Park from the beach?

Gulf beaches are typically about a 10-minute drive, depending on traffic.

Is Gillespie Park a walkable neighborhood?

Yes. Many residents enjoy walking or biking to downtown Sarasota, nearby parks, dining, and cultural attractions.

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