Recently Sold Homes near Windermere Preparatory School

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$490,000 Sold Jan 16, 2026

2237 Wintermere Pointe Dr, Winter Garden, FL 34787
- 4 Beds
- 2 Baths
- 1,950 Sq Ft
- Built 2000
Last Sold Summary
- 1% Below List Price
- $251/SF
- 1 Day On Market
Current Estimated Value $494,320

Last Listing Agent Tara Pintor CLOCK TOWER REALTY

2237 Wintermere Pointe Dr, Winter Garden, FL 34787
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$1,800,000 Sold May 23, 2025

6203 Blakeford Dr, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 4,350 Sq Ft
- Built 2001
Last Sold Summary
- 8% Below List Price
- $414/SF
- 261 Days On Market
Current Estimated Value $1,791,130

Last Listing Agent Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

6203 Blakeford Dr, Windermere, FL 34786
/2
$600,000 Sold May 11, 2025

15475 Camp Dubois Crescent, Winter Garden, FL 34787
- 6 Beds
- 3 Baths
- 2,674 Sq Ft
- Built 2013
Last Sold Summary
- $224/SF
- 2 Days On Market
Current Estimated Value $594,547

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

15475 Camp Dubois Crescent, Winter Garden, FL 34787
/2
$423,500 Sold May 21, 2025

6237 Aralia Ivy Ln, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 1,714 Sq Ft
- Built 2020
Last Sold Summary
- 3% Below List Price
- $247/SF
- 27 Days On Market
Current Estimated Value $435,846

Last Listing Agent Brandon Hamamura STELLAR REAL ESTATE OF FLORIDA

6237 Aralia Ivy Ln, Winter Garden, FL 34787
/2
$395,000 Sold Apr 06, 2026

8166 Mosaic Ln, Winter Garden, FL 34787
- 3 Beds
- 3 Baths
- 2,032 Sq Ft
- Built 2019
Last Sold Summary
- 14% Below List Price
- $194/SF
- 80 Days On Market
Current Estimated Value $455,209

Last Listing Agent Martonio Pinto AMERICAN HORIZONS REALTY

8166 Mosaic Ln, Winter Garden, FL 34787
/2
$790,000 Sold Apr 18, 2025

2341 Baronsmede Ct, Winter Garden, FL 34787
- 4 Beds
- 4.5 Baths
- 3,507 Sq Ft
- Built 2002
Last Sold Summary
- 7% Below List Price
- $225/SF
- 28 Days On Market
Current Estimated Value $786,677

Last Listing Agent Deb Obert WEICHERT REALTORS HALLMARK PRO

2341 Baronsmede Ct, Winter Garden, FL 34787
/2
$1,330,000 Sold Dec 29, 2025

12904 Canopy Woods Way, Winter Garden, FL 34787
- 4 Beds
- 4.5 Baths
- 3,665 Sq Ft
- Built 2018
Last Sold Summary
- 3% Below List Price
- $363/SF
- 21 Days On Market
Current Estimated Value $1,319,969

Last Listing Agent Freyda Smith CHARLES RUTENBERG REALTY ORLANDO

12904 Canopy Woods Way, Winter Garden, FL 34787
/2
$675,000 Sold Aug 21, 2025

14936 Masthead Landing Cir, Winter Garden, FL 34787
- 5 Beds
- 3 Baths
- 2,826 Sq Ft
- Built 2005
Last Sold Summary
- 3% Below List Price
- $239/SF
- 61 Days On Market
Current Estimated Value $660,527

Last Listing Agent Beatriz Dominguez BROKERS REAL ESTATE GROUP INC

14936 Masthead Landing Cir, Winter Garden, FL 34787
/2
$1,100,000 Sold May 26, 2025

9076 Great Heron Cir, Orlando, FL 32836
- 4 Beds
- 3.5 Baths
- 3,133 Sq Ft
- Built 1990
Last Sold Summary
- $351/SF
Current Estimated Value $1,110,744

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

9076 Great Heron Cir, Orlando, FL 32836
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$760,000 Sold Oct 17, 2025

13218 Orange Isle Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,109 Sq Ft
- Built 2021
Last Sold Summary
- 3% Below List Price
- $244/SF
- 57 Days On Market
Current Estimated Value $756,316

Last Listing Agent Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

13218 Orange Isle Dr, Windermere, FL 34786
/2
$490,000 Sold Apr 24, 2025

12777 Bosworth Ave, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,696 Sq Ft
- Built 2012
Last Sold Summary
- 8% Below List Price
- $289/SF
- 130 Days On Market
Current Estimated Value $496,322

Last Listing Agent Stephanie Pitts KELLER WILLIAMS CLASSIC

12777 Bosworth Ave, Windermere, FL 34786
$613,504 Sold Feb 25, 2026

5936 Flowering Cherry Bend, Winter Garden, FL 34787
- 3 Beds
- 2 Baths
- 1,772 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $346/SF
- 104 Days On Market
Dream Finders Homes Avalon Woods - 40' Homesites

5936 Flowering Cherry Bend, Winter Garden, FL 34787
/2
$830,000 Sold Jan 16, 2026

11031 Ledgement Ln, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 2,788 Sq Ft
- Built 2003
Last Sold Summary
- 8% Below List Price
- $298/SF
- 178 Days On Market
Current Estimated Value $843,398

Last Listing Agent Billy Wygle THE WILKINS WAY LLC

11031 Ledgement Ln, Windermere, FL 34786
/2
$575,000 Sold Oct 01, 2025

14436 Topaghan Way, Winter Garden, FL 34787
- 4 Beds
- 3 Baths
- 2,107 Sq Ft
- Built 2022
Last Sold Summary
- 6% Below List Price
- $273/SF
- 189 Days On Market
Current Estimated Value $581,031

Last Listing Agent Elisabeth Rusnak SOUTHERN REALTY GROUP LLC

14436 Topaghan Way, Winter Garden, FL 34787
/2
$425,000 Sold Feb 01, 2026

403 Lake Amberleigh Dr, Winter Garden, FL 34787
- 3 Beds
- 2 Baths
- 1,713 Sq Ft
- Built 2002
Last Sold Summary
- 7% Below List Price
- $248/SF
- 11 Days On Market
Current Estimated Value $430,655

Last Listing Agent Vimi Gobin PINNACLE SIGNATURE REALTY LLC

403 Lake Amberleigh Dr, Winter Garden, FL 34787
/2
$2,175,000 Sold Mar 06, 2026

16689 Broadwater Ave, Winter Garden, FL 34787
- 7 Beds
- 6.5 Baths
- 5,283 Sq Ft
- Built 2016
Last Sold Summary
- 3% Below List Price
- $412/SF
- 75 Days On Market
Current Estimated Value $2,200,990

Last Listing Agent Bent Danholm DANHOLM COLLECTION

16689 Broadwater Ave, Winter Garden, FL 34787
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$636,000 Sold Apr 11, 2025

4253 Willow Bay Dr, Winter Garden, FL 34787
- 3 Beds
- 2 Baths
- 2,406 Sq Ft
- Built 1994
Last Sold Summary
- 8% Below List Price
- $264/SF
- 58 Days On Market
Current Estimated Value $642,984

Last Listing Agent Raymond York SGT YORKS REAL ESTATE SERVICES

4253 Willow Bay Dr, Winter Garden, FL 34787
/2
$1,330,000 Sold May 30, 2025

14442 Avenue of the Rushes, Winter Garden, FL 34787
- 5 Beds
- 5 Baths
- 4,969 Sq Ft
- Built 2012
Last Sold Summary
- 7% Below List Price
- $268/SF
- 74 Days On Market
Current Estimated Value $1,353,873

Last Listing Agent Jeffrey Funk EXP REALTY LLC

14442 Avenue of the Rushes, Winter Garden, FL 34787
/2
$600,000 Sold Dec 15, 2025

12925 Holdenbury Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,981 Sq Ft
- Built 2013
Last Sold Summary
- 4% Below List Price
- $201/SF
- 98 Days On Market
Current Estimated Value $614,460

Last Listing Agent Eric Nelson SIGNATURE HOMES

12925 Holdenbury Ln, Windermere, FL 34786
/2
$619,000 Sold Dec 18, 2025

8776 Crescendo Ave, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,072 Sq Ft
- Built 2016
Last Sold Summary
- $299/SF
- 4 Days On Market
Current Estimated Value $619,101

Last Listing Agent Matt Kester THE REAL ESTATE COLLECTION LLC

8776 Crescendo Ave, Windermere, FL 34786
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$565,000 Sold Sep 29, 2025

6545 Chagford Ln, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,265 Sq Ft
- Built 2007
Last Sold Summary
- $249/SF
Current Estimated Value $554,835

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

6545 Chagford Ln, Windermere, FL 34786
/2
$805,000 Sold Feb 13, 2026

14551 Yellow Butterfly Rd, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,546 Sq Ft
- Built 2014
Last Sold Summary
- 2% Below List Price
- $227/SF
- 51 Days On Market
Current Estimated Value $795,634

Last Listing Agent Silvia Odebrecht ICON REALTY ASSOCIATES INC

14551 Yellow Butterfly Rd, Windermere, FL 34786
/2
$783,000 Sold Jan 09, 2026

5940 Chesapeake Park Unit 47, Orlando, FL 32819
- 3 Beds
- 2.5 Baths
- 2,612 Sq Ft
- Built 1983
Last Sold Summary
- 19% Below List Price
- $300/SF
- 251 Days On Market
Current Estimated Value $800,930

Last Listing Agent Michelle Corbin ISLEWORTH REALTY LLC

5940 Chesapeake Park Unit 47, Orlando, FL 32819
/2
$1,535,000 Sold Sep 19, 2025

11755 Waterstone Loop Dr, Windermere, FL 34786
- 5 Beds
- 5 Baths
- 3,665 Sq Ft
- Built 2012
Last Sold Summary
- 4% Below List Price
- $419/SF
- 97 Days On Market
Current Estimated Value $1,517,715

Last Listing Agent Deb Schroeder INFINITY REALTY GROUP LLC

11755 Waterstone Loop Dr, Windermere, FL 34786
/26
$974,990 Sold Sep 12, 2025

11057 Hollow Bay Dr, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 3,327 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $293/SF
- 22 Days On Market
Current Estimated Value $903,000

D.R. Horton Waterleigh

11057 Hollow Bay Dr, Winter Garden, FL 34787
/2
$1,800,000 Sold Jan 15, 2026

5412 Water Creek Dr, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 4,247 Sq Ft
- Built 2005
Last Sold Summary
- 10% Below List Price
- $424/SF
- 39 Days On Market
Current Estimated Value $1,811,242

Last Listing Agent Kari Fleck THE REAL ESTATE COLLECTION LLC

5412 Water Creek Dr, Windermere, FL 34786
/2
$649,000 Sold Jun 04, 2025

3136 Winesap Way, Winter Garden, FL 34787
- 4 Beds
- 3 Baths
- 2,540 Sq Ft
- Built 2016
Last Sold Summary
- 4% Below List Price
- $256/SF
- 66 Days On Market
Current Estimated Value $647,552

Last Listing Agent Maribel Ramos VESTI LLC

3136 Winesap Way, Winter Garden, FL 34787
/2
$720,000 Sold Aug 15, 2025

10417 Oakview Pointe Terrace, Gotha, FL 34734
- 4 Beds
- 3 Baths
- 2,402 Sq Ft
- Built 2002
Last Sold Summary
- 4% Below List Price
- $300/SF
- 54 Days On Market
Current Estimated Value $693,506

Last Listing Agent Rhiana Rusnak REAL BROKER, LLC

10417 Oakview Pointe Terrace, Gotha, FL 34734
/2
$8,000,000 Sold Apr 21, 2025

12238 Park Ave, Windermere, FL 34786
- 3 Beds
- 3.5 Baths
- 4,110 Sq Ft
- Built 1962
Last Sold Summary
- $1,946/SF
Current Estimated Value $3,845,491

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

12238 Park Ave, Windermere, FL 34786
/2
$575,000 Sold Jan 30, 2026

6700 Tamarind Cir, Orlando, FL 32819
- 4 Beds
- 2 Baths
- 1,914 Sq Ft
- Built 1977
Last Sold Summary
- 11% Below List Price
- $300/SF
- 249 Days On Market
Current Estimated Value $563,725

Last Listing Agent Heather Spirazza REGENCY REAL ESTATE LLC

6700 Tamarind Cir, Orlando, FL 32819
/2
$1,755,000 Sold Aug 15, 2025

11856 Vinci Dr, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 3,680 Sq Ft
- Built 2011
Last Sold Summary
- 5% Below List Price
- $477/SF
- 108 Days On Market
Current Estimated Value $1,727,993

Last Listing Agent Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

11856 Vinci Dr, Windermere, FL 34786
/2
$505,000 Sold Mar 26, 2026

8006 Jozee Cir, Orlando, FL 32836
- 3 Beds
- 2 Baths
- 1,661 Sq Ft
- Built 1980
Last Sold Summary
- 3% Below List Price
- $304/SF
- 9 Days On Market
Current Estimated Value $523,543

Last Listing Agent Alexander van Grondelle NEXTHOME HORIZON REALTY

8006 Jozee Cir, Orlando, FL 32836
/2
$520,000 Sold Sep 19, 2025

7920 S Marbella Ct, Orlando, FL 32836
- 3 Beds
- 2 Baths
- 1,619 Sq Ft
- Built 1989
Last Sold Summary
- 5% Below List Price
- $321/SF
- 34 Days On Market
Current Estimated Value $510,097

Last Listing Agent Ivey Geisler KELLER WILLIAMS REALTY AT THE PARKS

7920 S Marbella Ct, Orlando, FL 32836
/2
$460,000 Sold Feb 11, 2026

8059 N Cadiz Ct, Orlando, FL 32836
- 3 Beds
- 2 Baths
- 1,295 Sq Ft
- Built 1985
Last Sold Summary
- 2% Above List Price
- $355/SF
- 3 Days On Market
Current Estimated Value $456,514

Last Listing Agent Erika Gao RC GROUP REALTY LLC

8059 N Cadiz Ct, Orlando, FL 32836
/2
$1,045,000 Sold Jan 20, 2026

8764 Lookout Pointe Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,423 Sq Ft
- Built 2015
Last Sold Summary
- 4% Below List Price
- $305/SF
- 71 Days On Market
Current Estimated Value $1,031,311

Last Listing Agent Ken Pozek REAL BROKER, LLC

8764 Lookout Pointe Dr, Windermere, FL 34786
/2
$670,000 Sold Sep 09, 2025

9473 Palm Tree Dr, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,084 Sq Ft
- Built 1986
Last Sold Summary
- 3% Below List Price
- $321/SF
- 7 Days On Market
Current Estimated Value $652,976

Last Listing Agent Mike Long COLDWELL BANKER REALTY

9473 Palm Tree Dr, Windermere, FL 34786
/2
$465,000 Sold Oct 20, 2025

15064 Grove Lake Dr, Horizon West, FL 34787
- 3 Beds
- 2.5 Baths
- 1,846 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $252/SF
- 49 Days On Market
Current Estimated Value $461,127

Last Listing Agent Adam Schott DRB GROUP REALTY, LLC

15064 Grove Lake Dr, Horizon West, FL 34787
/2
$1,500,000 Sold Jun 30, 2025

16161 Barkly Ridge Ct, Winter Garden, FL 34787
- 6 Beds
- 6.5 Baths
- 5,424 Sq Ft
- Built 2024
Last Sold Summary
- 16% Below List Price
- $277/SF
- 86 Days On Market
Current Estimated Value $1,446,333

Last Listing Agent Bruna Sereno SELECTA REALTY LLC

16161 Barkly Ridge Ct, Winter Garden, FL 34787
/2
$939,000 Sold Apr 16, 2025

315 E 6th Ave, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,869 Sq Ft
- Built 1964
Last Sold Summary
- $327/SF
- 13 Days On Market
Current Estimated Value $940,565

Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

315 E 6th Ave, Windermere, FL 34786
/2
$1,625,000 Sold Nov 21, 2025

6054 Tarawood Dr, Orlando, FL 32819
- 4 Beds
- 3 Baths
- 3,070 Sq Ft
- Built 1978
Last Sold Summary
- 24% Below List Price
- $529/SF
- 158 Days On Market
Current Estimated Value $1,631,031

Last Listing Agent Michael Julian JULIAN PROPERTIES, INC.

6054 Tarawood Dr, Orlando, FL 32819

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