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You are here: Home / Gillespie Park in Sarasota : Homes for Sale in a Diverse Neighborhood

Gillespie Park in Sarasota : Homes for Sale in a Diverse Neighborhood

Gillespie Park in Sarasota Playground
Located just blocks away from Downtown, Gillespie Park in Sarasota is a neighborhood that evokes a prestige similar to that of Old City in Philadelphia, Beacon Hill in Boston and the French Quarter of New Orleans.

Thanks to its historic standing and organic development dating back to 1920, the Gillespie Park residential district is one of Sarasota’s most cherished neighborhoods. The public park that anchors this charming community was named after the first Mayor of Sarasota, a man who firmly believed that his city was destined for greatness. These days, Gillespie Park stands as a truly diverse neighborhood in terms of history, culture and residential architecture.

The various styles found in Gillespie Park include Old Florida, Spanish Colonial, French Country, and Caribbean. In recent years, home builders have added Modernist and Mediterranean designs to the already eclectic mix. The stately character of this neighborhood, coupled with its proximity to Downtown Sarasota, have provided a very positive effect on home values. If you are a property investor, this is a district that you will want to add to your list of investment targets.

As of mid-2018, a historic Old Florida home with two bedrooms and two bathrooms was listed under $500K. One of the most attractive listings was a Southern Plantation mansion with eight bedrooms, five bathrooms and a wrought iron fence surrounding a lot larger than 10,000 square feet. A 2018 Modernist home with four bedrooms and two levels was listed for less than $600K.

Residents of Gillespie Park live within walking distance of a park featuring tennis courts, picnic grounds, a pond, a pavilion, and nature trails. The museums, galleries and theaters of Downtown Sarasota are only blocks away, and driving to the beach takes about 10 minutes. Shopping, dining and entertainment options can be found all around the district.

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

Homes for Sale at Gillespie Park in Sarasota

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  • 1726 8th Street, Sarasota, FL
    1726 8th Street
    Sarasota, FL
    Photo of 1726 8th Street, Sarasota, FL 34236 (MLS # A4651820)
    $650,000
    • Lot Size
      7,406 sqft

    • Home Size
      1,569 sqft

    • Beds
      4 Beds

    • Baths
      2 Baths

    • Year Built
      1971

    • Days on Market
      3

    View Virtual Tour
  • 1726 8th Street, Sarasota, FL
    1726 8th Street
    Sarasota, FL
    Photo of 1726 8th Street, Sarasota, FL 34236 (MLS # A4651815)
    $650,000
    • Lot Size
      7,406 sqft

    • Home Size

    • Beds

    • Baths

    • Year Built
      0

    • Days on Market
      3

    View Virtual Tour
  • 1726 8th Street, Sarasota, FL
    1726 8th Street
    Sarasota, FL
    Photo of 1726 8th Street, Sarasota, FL 34236 (MLS # A4651812)
    $650,000
    • Lot Size
      7,406 sqft

    • Home Size
      1,569 sqft

    • Beds
      4 Beds

    • Baths
      2 Baths

    • Year Built
      1971

    • Days on Market
      3

    View Virtual Tour
  • 1755 7th Street, Sarasota, FL
    1755 7th Street
    Sarasota, FL
    Photo of 1755 7th Street, Sarasota, FL 34236 (MLS # A4651311)
    $2,950,000
    • Lot Size
      7,406 sqft

    • Home Size
      4,451 sqft

    • Beds
      4 Beds

    • Baths
      4 Baths

    • Year Built
      2023

    • Days on Market
      4

    View Virtual Tour
  • 1755 7th Street, Sarasota, FL
    1755 7th Street
    Sarasota, FL
    Photo of 1755 7th Street, Sarasota, FL 34236 (MLS # A4645817)
    $2,950,000
    • Lot Size
      7,406 sqft

    • Home Size
      4,451 sqft

    • Beds
      4 Beds

    • Baths
      4 Baths

    • Year Built
      2023

    • Days on Market
      4

    View Virtual Tour

See all Gillespie Park Sarasota Homes for Sale.
(all data current as of 5/8/2025)

Listing information deemed reliable but not guaranteed. Read full disclaimer.

 
 

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eXp Realty
Phone: (941) 421-7375
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Downtown Sarasota Neighborhoods & Condo Communities

  • 100 Central
  • 624 Palm
  • 7 One One
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  • Alinari
  • Allure
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  • Avondale
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  • Bay Point Park
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  • Bayview Heights
  • Beau Ciel
  • Bird Key
  • BLVD Sarasota
  • Broadway Promenade
  • Bungalow Hill
  • Burns Court
  • Central Park
  • Central Park II
  • Cherokee Park
  • Citrus Square
  • Cityscape
  • Condo on the Bay
  • Demarcay
  • Dolphin Tower
  • Embassy House
  • Encore
  • Epoch
  • Echelon on Palm
  • Essex House
  • Frances Carlton
  • Gillespie Park
  • Golden Gate Point
  • Granada
  • Grande Riviera
  • Grove Heights
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  • Harbor Acres
  • Hudson Bayou
  • Hudson Harbour
  • Kanaya
  • La Bellasara
  • Laurel Park
  • Lawrence Pointe
  • Le Chateau
  • Majestic Bay
  • Marina Tower
  • Marquee En Ville
  • McClellan Park
  • One Watergate
  • ONE88
  • Orange Blossom
  • Orange Club
  • Palm Place
  • Paradise Shores
  • Phoenix
  • Pier 550
  • Plaza at Five Points
  • Regency House
  • Renaissance
  • Rigbys
  • Ritz Carlton
  • Rivo at Ringling
  • Royal St. Andrew
  • San Remo Estates
  • Sansara
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  • St Regis
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  • Tahiti Park
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Areas We Serve

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Phone: (941) 421-7375
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Latest Real Estate

  • $425,000 8377 Mambo Avenue
    North Port, FL
  • $987,000 5531 Cannes Cir #201
    Sarasota, FL
  • $295,000 17655 Opal Sand Drive #304
    Venice, FL
  • $275,000 17470 Opal Sand Drive #103
    Venice, FL
  • $285,000 17595 Opal Sand Drive #104
    Venice, FL
  • $529,000 3803 E Bay Drive #10
    Bradenton Beach, FL
  • $389,000 5331 Citadel Road
    Venice, FL
  • $6,850,000 216 Tenacity Lane
    Sarasota, FL
  • $325,900 8205 Grand Estuary Trail #101
    Bradenton, FL
  • $530,000 1234 Paradise Way
    Venice, FL
  • $430,000 4627 56th Drive E
    Bradenton, FL
  • $783,000 4928 Hidden Oaks Trail
    Sarasota, FL
  • $1,198,000 140 Riviera Dunes Way #1203
    Palmetto, FL
  • $630,000 4403 Via Del Villetti Drive
    Venice, FL
  • $160,000 5619 Bayshore Road #164
    Palmetto, FL
  • $699,900 5320 Layton Drive
    Venice, FL
  • $399,900 7302 9th Avenue W #5836
    Bradenton, FL
  • $454,000 11648 Okaloosa Drive
    Venice, FL
  • $890,000 12240 Thornhill Court
    Lakewood Ranch, FL
  • $474,900 1227 Waterside Lane
    Venice, FL
8377 Mambo Avenue
North Port, FL
Photo of 8377 Mambo Avenue, North Port, FL 34291 (MLS # C7509663)
$425,000
Lot Size
10,019 sqft

Home Size
2,162 sqft

Beds
4 Beds

Baths
2 Baths

5531 Cannes Cir #201
Sarasota, FL
Photo of 5531 Cannes Cir #201, Sarasota, FL 34231 (MLS # A4651888)
$987,000
Lot Size
N/A

Home Size
2,024 sqft

Beds
3 Beds

Baths
2 Baths

17655 Opal Sand Drive #304
Venice, FL
Photo of 17655 Opal Sand Drive #304, Venice, FL 34293 (MLS # TB8383428)
$295,000
Lot Size
4,356 sqft

Home Size
1,120 sqft

Beds
2 Beds

Baths
2 Baths

17470 Opal Sand Drive #103
Venice, FL
Photo of 17470 Opal Sand Drive #103, Venice, FL 34293 (MLS # TB8383457)
$275,000
Lot Size
4,356 sqft

Home Size
1,366 sqft

Beds
2 Beds

Baths
2 Baths

17595 Opal Sand Drive #104
Venice, FL
Photo of 17595 Opal Sand Drive #104, Venice, FL 34293 (MLS # TB8383421)
$285,000
Lot Size
4,356 sqft

Home Size
1,120 sqft

Beds
2 Beds

Baths
2 Baths

3803 E Bay Drive #10
Bradenton Beach, FL
Photo of 3803 E Bay Drive #10, Bradenton Beach, FL 34217 (MLS # A4651831)
$529,000
Lot Size
N/A

Home Size
1,320 sqft

Beds
2 Beds

Baths
2 Baths

5331 Citadel Road
Venice, FL
Photo of 5331 Citadel Road, Venice, FL 34293 (MLS # C7509656)
$389,000
Lot Size
7,841 sqft

Home Size
1,718 sqft

Beds
3 Beds

Baths
2 Baths

216 Tenacity Lane
Sarasota, FL
Photo of 216 Tenacity Lane, Sarasota, FL 34242 (MLS # A4650729)
$6,850,000
Lot Size
11,326 sqft

Home Size
2,454 sqft

Beds
3 Beds

Baths
4 Baths

8205 Grand Estuary Trail #101
Bradenton, FL
Photo of 8205 Grand Estuary Trail #101, Bradenton, FL 34212 (MLS # A4650247)
$325,900
Lot Size
42,254 sqft

Home Size
1,296 sqft

Beds
2 Beds

Baths
2 Baths

1234 Paradise Way
Venice, FL
Photo of 1234 Paradise Way, Venice, FL 34285 (MLS # N6138800)
$530,000
Lot Size
9,584 sqft

Home Size
1,702 sqft

Beds
2 Beds

Baths
2 Baths

4627 56th Drive E
Bradenton, FL
Photo of 4627 56th Drive E, Bradenton, FL 34203 (MLS # A4651703)
$430,000
Lot Size
12,197 sqft

Home Size
1,557 sqft

Beds
3 Beds

Baths
2 Baths

4928 Hidden Oaks Trail
Sarasota, FL
Photo of 4928 Hidden Oaks Trail, Sarasota, FL 34232 (MLS # A4651852)
$783,000
Lot Size
1.13 ac

Home Size
2,182 sqft

Beds
3 Beds

Baths
2 Baths

140 Riviera Dunes Way #1203
Palmetto, FL
Photo of 140 Riviera Dunes Way #1203, Palmetto, FL 34221 (MLS # TB8383622)
$1,198,000
Lot Size
1.38 ac

Home Size
2,930 sqft

Beds
3 Beds

Baths
4 Baths

4403 Via Del Villetti Drive
Venice, FL
Photo of 4403 Via Del Villetti Drive, Venice, FL 34293 (MLS # N6138778)
$630,000
Lot Size
9,584 sqft

Home Size
2,188 sqft

Beds
2 Beds

Baths
2 Baths

5619 Bayshore Road #164
Palmetto, FL
Photo of 5619 Bayshore Road #164, Palmetto, FL 34221 (MLS # A4651830)
$160,000
Lot Size
3,921 sqft

Home Size
1,224 sqft

Beds
2 Beds

Baths
2 Baths

5320 Layton Drive
Venice, FL
Photo of 5320 Layton Drive, Venice, FL 34293 (MLS # A4651889)
$699,900
Lot Size
9,584 sqft

Home Size
2,835 sqft

Beds
4 Beds

Baths
3 Baths

7302 9th Avenue W #5836
Bradenton, FL
Photo of 7302 9th Avenue W #5836, Bradenton, FL 34209 (MLS # A4651825)
$399,900
Lot Size
8.84 ac

Home Size
1,745 sqft

Beds
2 Beds

Baths
2 Baths

11648 Okaloosa Drive
Venice, FL
Photo of 11648 Okaloosa Drive, Venice, FL 34293 (MLS # N6138784)
$454,000
Lot Size
4,356 sqft

Home Size
1,632 sqft

Beds
2 Beds

Baths
2 Baths

12240 Thornhill Court
Lakewood Ranch, FL
Photo of 12240 Thornhill Court, Lakewood Ranch, FL 34202 (MLS # A4651878)
$890,000
Lot Size
10,455 sqft

Home Size
2,582 sqft

Beds
3 Beds

Baths
3 Baths

1227 Waterside Lane
Venice, FL
Photo of 1227 Waterside Lane, Venice, FL 34285 (MLS # A4651856)
$474,900
Lot Size
9,584 sqft

Home Size
1,862 sqft

Beds
3 Beds

Baths
2 Baths

  • 8377 Mambo Avenue
    North Port, FL
    Photo of 8377 Mambo Avenue, North Port, FL 34291 (MLS # C7509663)
    $425,000
    Lot Size
    10,019 sqft

    Home Size
    2,162 sqft

    Beds
    4 Beds

    Baths
    2 Baths

  • 5531 Cannes Cir #201
    Sarasota, FL
    Photo of 5531 Cannes Cir #201, Sarasota, FL 34231 (MLS # A4651888)
    $987,000
    Lot Size
    N/A

    Home Size
    2,024 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 17655 Opal Sand Drive #304
    Venice, FL
    Photo of 17655 Opal Sand Drive #304, Venice, FL 34293 (MLS # TB8383428)
    $295,000
    Lot Size
    4,356 sqft

    Home Size
    1,120 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 17470 Opal Sand Drive #103
    Venice, FL
    Photo of 17470 Opal Sand Drive #103, Venice, FL 34293 (MLS # TB8383457)
    $275,000
    Lot Size
    4,356 sqft

    Home Size
    1,366 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 17595 Opal Sand Drive #104
    Venice, FL
    Photo of 17595 Opal Sand Drive #104, Venice, FL 34293 (MLS # TB8383421)
    $285,000
    Lot Size
    4,356 sqft

    Home Size
    1,120 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 3803 E Bay Drive #10
    Bradenton Beach, FL
    Photo of 3803 E Bay Drive #10, Bradenton Beach, FL 34217 (MLS # A4651831)
    $529,000
    Lot Size
    N/A

    Home Size
    1,320 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 5331 Citadel Road
    Venice, FL
    Photo of 5331 Citadel Road, Venice, FL 34293 (MLS # C7509656)
    $389,000
    Lot Size
    7,841 sqft

    Home Size
    1,718 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 216 Tenacity Lane
    Sarasota, FL
    Photo of 216 Tenacity Lane, Sarasota, FL 34242 (MLS # A4650729)
    $6,850,000
    Lot Size
    11,326 sqft

    Home Size
    2,454 sqft

    Beds
    3 Beds

    Baths
    4 Baths

  • 8205 Grand Estuary Trail #101
    Bradenton, FL
    Photo of 8205 Grand Estuary Trail #101, Bradenton, FL 34212 (MLS # A4650247)
    $325,900
    Lot Size
    42,254 sqft

    Home Size
    1,296 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 1234 Paradise Way
    Venice, FL
    Photo of 1234 Paradise Way, Venice, FL 34285 (MLS # N6138800)
    $530,000
    Lot Size
    9,584 sqft

    Home Size
    1,702 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 4627 56th Drive E
    Bradenton, FL
    Photo of 4627 56th Drive E, Bradenton, FL 34203 (MLS # A4651703)
    $430,000
    Lot Size
    12,197 sqft

    Home Size
    1,557 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 4928 Hidden Oaks Trail
    Sarasota, FL
    Photo of 4928 Hidden Oaks Trail, Sarasota, FL 34232 (MLS # A4651852)
    $783,000
    Lot Size
    1.13 ac

    Home Size
    2,182 sqft

    Beds
    3 Beds

    Baths
    2 Baths

  • 140 Riviera Dunes Way #1203
    Palmetto, FL
    Photo of 140 Riviera Dunes Way #1203, Palmetto, FL 34221 (MLS # TB8383622)
    $1,198,000
    Lot Size
    1.38 ac

    Home Size
    2,930 sqft

    Beds
    3 Beds

    Baths
    4 Baths

  • 4403 Via Del Villetti Drive
    Venice, FL
    Photo of 4403 Via Del Villetti Drive, Venice, FL 34293 (MLS # N6138778)
    $630,000
    Lot Size
    9,584 sqft

    Home Size
    2,188 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 5619 Bayshore Road #164
    Palmetto, FL
    Photo of 5619 Bayshore Road #164, Palmetto, FL 34221 (MLS # A4651830)
    $160,000
    Lot Size
    3,921 sqft

    Home Size
    1,224 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 5320 Layton Drive
    Venice, FL
    Photo of 5320 Layton Drive, Venice, FL 34293 (MLS # A4651889)
    $699,900
    Lot Size
    9,584 sqft

    Home Size
    2,835 sqft

    Beds
    4 Beds

    Baths
    3 Baths

  • 7302 9th Avenue W #5836
    Bradenton, FL
    Photo of 7302 9th Avenue W #5836, Bradenton, FL 34209 (MLS # A4651825)
    $399,900
    Lot Size
    8.84 ac

    Home Size
    1,745 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 11648 Okaloosa Drive
    Venice, FL
    Photo of 11648 Okaloosa Drive, Venice, FL 34293 (MLS # N6138784)
    $454,000
    Lot Size
    4,356 sqft

    Home Size
    1,632 sqft

    Beds
    2 Beds

    Baths
    2 Baths

  • 12240 Thornhill Court
    Lakewood Ranch, FL
    Photo of 12240 Thornhill Court, Lakewood Ranch, FL 34202 (MLS # A4651878)
    $890,000
    Lot Size
    10,455 sqft

    Home Size
    2,582 sqft

    Beds
    3 Beds

    Baths
    3 Baths

  • 1227 Waterside Lane
    Venice, FL
    Photo of 1227 Waterside Lane, Venice, FL 34285 (MLS # A4651856)
    $474,900
    Lot Size
    9,584 sqft

    Home Size
    1,862 sqft

    Beds
    3 Beds

    Baths
    2 Baths

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