Recently Sold Windermere, FL Homes

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$599,990

Sold Jun 15, 2026

6315 Clearmeadow Ct, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,077 Sq Ft
- Built 2002
Last Sold Summary
- 3% Below List Price
- $289/SF
- 20 Days On Market
Current Estimated Value $617,294

Last Listing Agent Jessica Otero KELLER WILLIAMS REALTY AT THE PARKS

6315 Clearmeadow Ct, Windermere, FL 34786
/2
$470,000

Sold Mar 26, 2026

7028 Ventnor Dr, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 1,980 Sq Ft
- Built 2008
Last Sold Summary
- 10% Below List Price
- $237/SF
- 84 Days On Market
Current Estimated Value $469,583

Last Listing Agent Amanda Black PA UPSIDE REAL ESTATE INC

7028 Ventnor Dr, Windermere, FL 34786
/2
$900,000

Sold Sep 26, 2025

6426 Montclair Bluff Ln, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 3,080 Sq Ft
- Built 2002
Last Sold Summary
- 10% Below List Price
- $292/SF
- 76 Days On Market
Current Estimated Value $906,238

Last Listing Agent Charlie Akduman REGENCY REAL ESTATE LLC

6426 Montclair Bluff Ln, Windermere, FL 34786
/2
$890,000

Sold May 04, 2026

13858 Caywood Pond Dr, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,070 Sq Ft
- Built 2004
Last Sold Summary
- 11% Below List Price
- $290/SF
- 38 Days On Market
Current Estimated Value $934,787

Last Listing Agent Chun Cai SPRING REALTY ONE LLC

13858 Caywood Pond Dr, Windermere, FL 34786
/2
$1,130,000

Sold Oct 31, 2025

1438 Belfiore Way, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 4,213 Sq Ft
- Built 2006
Last Sold Summary
- 5% Below List Price
- $268/SF
- 23 Days On Market
Current Estimated Value $1,140,025

Last Listing Agent Danilo Novak NOVAK REALTY CORP

1438 Belfiore Way, Windermere, FL 34786
/2
$360,000

Sold Nov 14, 2025

14234 Desert Haven St Unit 14234, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,067 Sq Ft
- Built 2012
Last Sold Summary
- 6% Below List Price
- $174/SF
- 113 Days On Market
Current Estimated Value $376,524

Last Listing Agent Debi Roldan KELLER WILLIAMS ADVANTAGE III

14234 Desert Haven St Unit 14234, Windermere, FL 34786
/2
$1,100,000

Sold Aug 07, 2025

2106 Ridgewind Way, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,838 Sq Ft
- Built 1999
Last Sold Summary
- 6% Below List Price
- $388/SF
- 25 Days On Market
Current Estimated Value $1,091,388

Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

2106 Ridgewind Way, Windermere, FL 34786
/2
$475,000

Sold Dec 30, 2025

8160 Iron Mountain Trail, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,009 Sq Ft
- Built 2016
Last Sold Summary
- 16% Below List Price
- $236/SF
- 201 Days On Market
Current Estimated Value $495,239

Last Listing Agent Francine Arroyo Santowski BHHS FLORIDA REALTY

8160 Iron Mountain Trail, Windermere, FL 34786
/2
$3,450,000

Sold Jan 23, 2026

10545 Down Lakeview Cir, Windermere, FL 34786
- 5 Beds
- 7 Baths
- 7,263 Sq Ft
- Built 1987
Last Sold Summary
- 9% Below List Price
- $475/SF
- 143 Days On Market
Current Estimated Value $3,575,075

Last Listing Agent Valerie Kennedy COLONIALTOWN REALTY

10545 Down Lakeview Cir, Windermere, FL 34786
/2
$1,600,000

Sold Jun 16, 2026

5106 Tildens Grove Blvd, Windermere, FL 34786
- 6 Beds
- 4.5 Baths
- 4,572 Sq Ft
- Built 2006
Last Sold Summary
- 6% Below List Price
- $350/SF
- 40 Days On Market
Current Estimated Value $1,685,081

Last Listing Agent Tara Moore TARA MOORE REAL ESTATE

5106 Tildens Grove Blvd, Windermere, FL 34786
/2
$862,000

Sold Jul 01, 2026

1925 Breezy Hill Dr, Windermere, FL 34786
- 5 Beds
- 3 Baths
- 3,063 Sq Ft
- Built 2001
Last Sold Summary
- 2% Below List Price
- $281/SF
- 34 Days On Market
Current Estimated Value $860,313

Last Listing Agent Michelle Melo FLORIDA REALTY INVESTMENTS

1925 Breezy Hill Dr, Windermere, FL 34786
/2
$426,000

Sold Mar 13, 2026

12944 Garridan Ave, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,583 Sq Ft
- Built 2007
Last Sold Summary
- 2% Above List Price
- $269/SF
- 5 Days On Market
Current Estimated Value $425,602

Last Listing Agent Fred Jackson 407 PROPERTIES

12944 Garridan Ave, Windermere, FL 34786
/2
$430,000

Sold Jun 30, 2026

7560 Bentonshire Ave, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 1,905 Sq Ft
- Built 2009
Last Sold Summary
- 3% Below List Price
- $226/SF
- 19 Days On Market
Current Estimated Value $440,133

Last Listing Agent Sharon Six SOLD BY SIX REALTY, LLC

7560 Bentonshire Ave, Windermere, FL 34786
/2
$2,050,000

Sold Oct 20, 2025

5502 Marleon Dr, Windermere, FL 34786
- 6 Beds
- 4.5 Baths
- 6,355 Sq Ft
- Built 2011
Last Sold Summary
- 2% Below List Price
- $323/SF
- 17 Days On Market
Current Estimated Value $2,059,247

Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

5502 Marleon Dr, Windermere, FL 34786
/2
$1,750,000

Sold Jun 30, 2026

12235 Montalcino Cir, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 4,550 Sq Ft
- Built 2018
Last Sold Summary
- 12% Below List Price
- $385/SF
- 107 Days On Market
Current Estimated Value $1,852,161

Last Listing Agent Teresa Stewart SOUTHERN REALTY GROUP LLC

12235 Montalcino Cir, Windermere, FL 34786
/2
$415,000

Sold Jul 22, 2025

5892 Soter Ln, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,001 Sq Ft
- Built 2019
Last Sold Summary
- 10% Below List Price
- $207/SF
- 82 Days On Market
Current Estimated Value $434,727

Last Listing Agent Claire Jesso SERHANT

5892 Soter Ln, Windermere, FL 34786
/2
$620,000

Sold Feb 12, 2026

13290 Orange Isle Dr, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,146 Sq Ft
- Built 2022
Last Sold Summary
- 5% Below List Price
- $289/SF
- 23 Days On Market
Current Estimated Value $621,295

Last Listing Agent Christian Posegger EMPIRE NETWORK REALTY

13290 Orange Isle Dr, Windermere, FL 34786
/45
$900,000

Sold Sep 05, 2025

6125 Foxfield Ct, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,868 Sq Ft
- Built 2000
Last Sold Summary
- 36% Below List Price
- $314/SF
- 104 Days On Market
Current Estimated Value $975,151

Last Listing Agent Mary Ann Thompson RE/MAX Elite

6125 Foxfield Ct, Windermere, FL 34786
/2
$6,600,000

Sold Aug 11, 2025

5507 Worsham Ct, Windermere, FL 34786
- 5 Beds
- 11 Baths
- 10,200 Sq Ft
- Built 2008
Last Sold Summary
- 24% Below List Price
- $647/SF
- 494 Days On Market
Current Estimated Value $6,678,370

Last Listing Agent Rob Rahter STOCKWORTH REALTY GROUP

5507 Worsham Ct, Windermere, FL 34786
/2
$1,035,000

Sold Dec 30, 2025

14244 Crest Palm Ave, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,764 Sq Ft
- Built 2025
Last Sold Summary
- $275/SF
Current Estimated Value $1,047,411

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

14244 Crest Palm Ave, Windermere, FL 34786
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$930,454

Sold Apr 13, 2026

14377 Crest Palm Ave, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,239 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $287/SF
- 8 Days On Market
Dream Finders Homes Palms at Windermere

14377 Crest Palm Ave, Windermere, FL 34786
/2
$2,000,000

Sold Jun 24, 2026

5926 Blakeford Dr, Windermere, FL 34786
- 4 Beds
- 4 Baths
- 3,906 Sq Ft
- Built 1999
Last Sold Summary
- 7% Below List Price
- $512/SF
- 40 Days On Market
Current Estimated Value $2,063,835

Last Listing Agent Teresa Stewart SOUTHERN REALTY GROUP LLC

5926 Blakeford Dr, Windermere, FL 34786
/2
$3,178,500

Sold Nov 12, 2025

6030 Greatwater Dr, Windermere, FL 34786
- 6 Beds
- 6.5 Baths
- 6,489 Sq Ft
- Built 1999
Last Sold Summary
- 1% Below List Price
- $490/SF
- 4 Days On Market
Current Estimated Value $3,169,244

Last Listing Agent TJ Cosgrove REAL BROKER, LLC

6030 Greatwater Dr, Windermere, FL 34786
/2
$560,000

Sold Apr 03, 2026

8650 Abbotsbury Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,628 Sq Ft
- Built 2004
Last Sold Summary
- 6% Below List Price
- $213/SF
- 20 Days On Market
Current Estimated Value $565,479

Last Listing Agent Andy Neal THE AGENCY FL

8650 Abbotsbury Dr, Windermere, FL 34786
/2
$1,160,000

Sold Jan 09, 2026

2 Oakdale St, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,152 Sq Ft
- Built 1959
Last Sold Summary
- 3% Below List Price
- $539/SF
- 3 Days On Market
Current Estimated Value $1,135,388

Last Listing Agent Christopher Bauman REVEL REALTY LLC

2 Oakdale St, Windermere, FL 34786
/2
$512,290

Sold Jul 01, 2026

11234 Rapallo Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,236 Sq Ft
- Built 2003
Last Sold Summary
- 1% Below List Price
- $229/SF
- 1 Day On Market
Current Estimated Value $570,808

Last Listing Agent Kyle Grafton FANNIE HILLMAN & ASSOCIATES

11234 Rapallo Ln, Windermere, FL 34786
/2
$1,158,517

Sold Aug 08, 2025

14360 Crest Palm Ave, Windermere, FL 34786
- 6 Beds
- 4.5 Baths
- 4,443 Sq Ft
- Built 2025
Last Sold Summary
- 8% Below List Price
- $261/SF
- 0 Days On Market
Current Estimated Value $1,172,667

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14360 Crest Palm Ave, Windermere, FL 34786
/2
$400,000

Sold Nov 18, 2025

14466 Bridgewater Crossings Blvd, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 1,642 Sq Ft
- Built 2006
Last Sold Summary
- 6% Below List Price
- $244/SF
- 87 Days On Market
Current Estimated Value $405,164

Last Listing Agent Tennille Biggers KELLER WILLIAMS ELITE PARTNERS III REALTY

14466 Bridgewater Crossings Blvd, Windermere, FL 34786
/2
$675,000

Sold Feb 24, 2026

7616 Colbury Ave, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,794 Sq Ft
- Built 2010
Last Sold Summary
- 3% Below List Price
- $242/SF
- 4 Days On Market
Current Estimated Value $677,999

Last Listing Agent Jenny Miller PROVIDENCE REALTY AND PROPERTY MANAGEMENT LLC

7616 Colbury Ave, Windermere, FL 34786
/2
$1,950,000

Sold Oct 20, 2025

1984 Windermere Rd, Windermere, FL 34786
- 6 Beds
- 5.5 Baths
- 6,601 Sq Ft
- Built 2014
Last Sold Summary
- 10% Below List Price
- $295/SF
- 180 Days On Market
Current Estimated Value $1,991,943

Last Listing Agent Steven Ritz KELLER WILLIAMS WINTER PARK

1984 Windermere Rd, Windermere, FL 34786
/2
$1,050,000

Sold Sep 23, 2025

5232 Tildens Grove Blvd, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 3,079 Sq Ft
- Built 2005
Last Sold Summary
- 9% Below List Price
- $341/SF
- 17 Days On Market
Current Estimated Value $1,130,038

Last Listing Agent Steve Healy CORCORAN PREMIER REALTY

5232 Tildens Grove Blvd, Windermere, FL 34786
/2
$1,120,000

Sold Nov 20, 2025

1927 Watermere Ln, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,053 Sq Ft
- Built 2005
Last Sold Summary
- 2% Below List Price
- $367/SF
- 11 Days On Market
Current Estimated Value $1,111,870

Last Listing Agent Guang Yang YOUR HOME SOLD GUARANTEED REALTY

1927 Watermere Ln, Windermere, FL 34786
/2
$640,000

Sold Feb 13, 2026

13413 Zori Ln, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,830 Sq Ft
- Built 2003
Last Sold Summary
- 5% Below List Price
- $226/SF
- 85 Days On Market
Current Estimated Value $641,463

Last Listing Agent Annie Kwan ORLANDO SUNSHINE REALTY

13413 Zori Ln, Windermere, FL 34786
/2
$1,700,000

Sold Oct 27, 2025

5243 W Lake Butler Rd, Windermere, FL 34786
- 3 Beds
- 3 Baths
- 3,255 Sq Ft
- Built 1996
Last Sold Summary
- 46% Below List Price
- $522/SF
- 211 Days On Market
Current Estimated Value $1,934,990

Last Listing Agent Andrew Burgard CHARLES RUTENBERG REALTY ORLANDO

5243 W Lake Butler Rd, Windermere, FL 34786
/2
$370,000

Sold Sep 03, 2025

7348 Yoder St, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,479 Sq Ft
- Built 2008
Last Sold Summary
- 11% Below List Price
- $250/SF
- 95 Days On Market
Current Estimated Value $366,465

Last Listing Agent Christopher Gabriel EXP REALTY LLC

7348 Yoder St, Windermere, FL 34786
/2
$1,070,000

Sold Sep 30, 2025

9641 Crown Prince Ln, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,924 Sq Ft
- Built 2001
Last Sold Summary
- 3% Below List Price
- $273/SF
- 2 Days On Market
Current Estimated Value $1,116,181

Last Listing Agent Anderson Tiu REIKI REALTY LLC

9641 Crown Prince Ln, Windermere, FL 34786
/2
$378,250

Sold Jul 08, 2025

12963 Garridan Ave, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,535 Sq Ft
- Built 2009
Last Sold Summary
- 3% Below List Price
- $246/SF
- 6 Days On Market
Current Estimated Value $378,299

Last Listing Agent Chase Morton Tate COMPASS FLORIDA LLC

12963 Garridan Ave, Windermere, FL 34786
/2
$640,000

Sold Apr 30, 2026

6638 Bridgewater Village Rd, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,908 Sq Ft
- Built 2013
Last Sold Summary
- 5% Below List Price
- $220/SF
- 91 Days On Market
Current Estimated Value $653,317

Last Listing Agent Nickolas Amburgey COMPASS FLORIDA LLC

6638 Bridgewater Village Rd, Windermere, FL 34786
/2
$340,000

Sold Apr 16, 2026

12327 Cruxbury Dr, Windermere, FL 34786
- 2 Beds
- 2.5 Baths
- 1,211 Sq Ft
- Built 2006
Last Sold Summary
- 4% Below List Price
- $281/SF
- 15 Days On Market
Current Estimated Value $338,430

Last Listing Agent Mae Stigell JASON MITCHELL REAL ESTATE FLO

12327 Cruxbury Dr, Windermere, FL 34786
/2
$425,000

Sold Jan 29, 2026

7545 Ripplepointe Way, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
- Built 2009
Last Sold Summary
- 1% Below List Price
- $262/SF
- 5 Days On Market
Current Estimated Value $417,013

Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

7545 Ripplepointe Way, Windermere, FL 34786

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