Recently Sold Windermere, FL Homes

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$350,000

Sold Jun 12, 2026

6528 Helmsley Cir, Windermere, FL 34786
- 2 Beds
- 2.5 Baths
- 1,411 Sq Ft
- Built 2008
Last Sold Summary
- 8% Above List Price
- $248/SF
- 8 Days On Market
Current Estimated Value $329,495

Last Listing Agent Daniel Rodriguez NEW HEIGHTS REALTY GROUP

6528 Helmsley Cir, Windermere, FL 34786
Explore Windermere
/42
$1,114,989

Sold May 04, 2026

14371 Crest Palm Ave, Windermere, FL 34786
- 4 Beds
- 4 Baths
- 3,138 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $355/SF
- 9 Days On Market
Current Estimated Value $1,104,333

Dream Finders Homes Palms at Windermere

14371 Crest Palm Ave, Windermere, FL 34786
/2
$750,000

Sold Sep 18, 2025

14654 Yellow Butterfly Rd, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,094 Sq Ft
- Built 2015
Last Sold Summary
- 6% Below List Price
- $242/SF
- 44 Days On Market
Current Estimated Value $744,891

Last Listing Agent Elijah Lewis FLORIDA IN MOTION REALTY INC

14654 Yellow Butterfly Rd, Windermere, FL 34786
/2
$2,350,000

Sold Oct 14, 2025

1003 Oakdale St, Windermere, FL 34786
- 6 Beds
- 5.5 Baths
- 4,599 Sq Ft
- Built 2003
Last Sold Summary
- 22% Below List Price
- $511/SF
- 280 Days On Market
Current Estimated Value $2,356,824

Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

1003 Oakdale St, Windermere, FL 34786
/2
$753,000

Sold Jan 21, 2026

11660 Delwick Dr, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 3,051 Sq Ft
- Built 2004
Last Sold Summary
- 16% Below List Price
- $247/SF
- 146 Days On Market
Current Estimated Value $775,717

Last Listing Agent Natalie Rosario FATHOM REALTY FL LLC

11660 Delwick Dr, Windermere, FL 34786
/2
$849,000

Sold Dec 09, 2025

11108 Ledgement Ln Unit 2, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,024 Sq Ft
- Built 2003
Last Sold Summary
- $281/SF
- 3 Days On Market
Current Estimated Value $846,438

Last Listing Agent Terrie Giles KELLER WILLIAMS CLASSIC

11108 Ledgement Ln Unit 2, Windermere, FL 34786
/2
$840,646

Sold Mar 30, 2026

4926 Indian Deer Rd, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 3,849 Sq Ft
- Built 2006
Last Sold Summary
- 12% Below List Price
- $218/SF
- 135 Days On Market
Current Estimated Value $862,961

Last Listing Agent Shelley Dawson COMPASS FLORIDA LLC

4926 Indian Deer Rd, Windermere, FL 34786
/2
$862,000

Sold Jan 08, 2026

299 W 4th Ave, Mount Dora, FL 32757
- 4 Beds
- 3 Baths
- 2,410 Sq Ft
- Built 1984
Last Sold Summary
- 4% Below List Price
- $358/SF
- 35 Days On Market
Current Estimated Value $859,216

Last Listing Agent Judy Black UPSIDE REAL ESTATE INC

299 W 4th Ave, Mount Dora, FL 32757
/2
$389,000

Sold Nov 07, 2025

6327 Southbridge St, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,490 Sq Ft
- Built 2007
Last Sold Summary
- 8% Below List Price
- $261/SF
- 169 Days On Market
Current Estimated Value $388,480

Last Listing Agent Vanessa Lee COLDWELL BANKER REALTY

6327 Southbridge St, Windermere, FL 34786
/2
$750,000

Sold Nov 12, 2025

13254 Penshurst Ln, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,720 Sq Ft
- Built 2015
Last Sold Summary
- 6% Below List Price
- $202/SF
- 96 Days On Market
Current Estimated Value $764,240

Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

13254 Penshurst Ln, Windermere, FL 34786
/2
$580,000

Sold Apr 13, 2026

7451 Fairgrove Ave, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,092 Sq Ft
- Built 2017
Last Sold Summary
- $277/SF
- 51 Days On Market
Current Estimated Value $574,346

Last Listing Agent Lorraine da Silva Andrade TALENT REALTY SOLUTIONS

7451 Fairgrove Ave, Windermere, FL 34786
/2
$1,000,000

Sold Oct 27, 2025

5235 W Lake Butler Rd, Windermere, FL 34786
- Land
- 29,620 Sq Ft
- $1,470,588 per Acre
Last Sold Summary
- 53% Below List Price
- 211 Days On Market
Current Estimated Value $1,025,956

Last Listing Agent Andrew Burgard CHARLES RUTENBERG REALTY ORLANDO

5235 W Lake Butler Rd, Windermere, FL 34786
/2
$735,000

Sold Oct 23, 2025

12821 Westside Village Loop, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,689 Sq Ft
- Built 2018
Last Sold Summary
- 2% Below List Price
- $199/SF
- 15 Days On Market
Current Estimated Value $762,374

Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

12821 Westside Village Loop, Windermere, FL 34786
/2
$1,274,000

Sold Mar 27, 2026

12779 Westside Village Loop, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,689 Sq Ft
- Built 2018
Last Sold Summary
- $345/SF
- 5 Days On Market
Current Estimated Value $1,224,751

Last Listing Agent Ramon Brandão WEBB FLORIDA REALTY LLC

12779 Westside Village Loop, Windermere, FL 34786
/2
$350,000

Sold Feb 04, 2026

7462 Bentonshire Ave, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,480 Sq Ft
- Built 2007
Last Sold Summary
- 9% Below List Price
- $236/SF
- 185 Days On Market
Current Estimated Value $356,581

Last Listing Agent Ivan Petkov FLORIDA REALTY INVESTMENTS

7462 Bentonshire Ave, Windermere, FL 34786
/2
$2,400,000

Sold May 05, 2026

8402 Lake Burden Cir Unit 2, Windermere, FL 34786
- 5 Beds
- 6.5 Baths
- 6,248 Sq Ft
- Built 2004
Last Sold Summary
- 16% Below List Price
- $384/SF
- 163 Days On Market
Current Estimated Value $2,643,663

Last Listing Agent Toni Marie Cafferty COMPASS FLORIDA LLC

8402 Lake Burden Cir Unit 2, Windermere, FL 34786
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$1,069,989

Sold Jan 22, 2026

14427 Crest Palm Ave, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 4,571 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $234/SF
- 15 Days On Market
Current Estimated Value $1,049,599

Dream Finders Homes Palms at Windermere

14427 Crest Palm Ave, Windermere, FL 34786
/2
$1,194,000

Sold Aug 25, 2025

6720 Winter Garden Vineland Rd, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,554 Sq Ft
- Built 2003
Last Sold Summary
- 8% Below List Price
- $336/SF
- 32 Days On Market
Current Estimated Value $1,280,440

Last Listing Agent Rita Schoeffler BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

6720 Winter Garden Vineland Rd, Windermere, FL 34786
/2
$975,000

Sold Apr 01, 2026

7545 Lake Albert Dr, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 3,425 Sq Ft
- Built 2008
Last Sold Summary
- 11% Below List Price
- $285/SF
- 158 Days On Market
Current Estimated Value $957,976

Last Listing Agent Nicole Mickle OLYMPUS EXECUTIVE REALTY INC

7545 Lake Albert Dr, Windermere, FL 34786
/2
$1,450,000

Sold Aug 13, 2025

8430 Woburn Ct, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,319 Sq Ft
- Built 1999
Last Sold Summary
- 3% Below List Price
- $437/SF
- 64 Days On Market
Current Estimated Value $1,421,023

Last Listing Agent Mauricio Penha VOLKE REAL ESTATE LLC

8430 Woburn Ct, Windermere, FL 34786
/2
$670,000

Sold Nov 14, 2025

2015 Woody Dr, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,042 Sq Ft
- Built 1978
Last Sold Summary
- 4% Below List Price
- $328/SF
- 28 Days On Market
Current Estimated Value $670,279

Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

2015 Woody Dr, Windermere, FL 34786
/2
$680,000

Sold Feb 20, 2026

4825 Palm Tree Ct, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,100 Sq Ft
- Built 1985
Last Sold Summary
- $324/SF
- 9 Days On Market
Current Estimated Value $672,492

Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

4825 Palm Tree Ct, Windermere, FL 34786
/2
$550,000

Sold Sep 30, 2025

5238 Beach River Rd, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,414 Sq Ft
- Built 2004
Last Sold Summary
- $228/SF
- 3 Days On Market
Current Estimated Value $560,903

Last Listing Agent Liza Farzati SERHANT

5238 Beach River Rd, Windermere, FL 34786
/2
$620,000

Sold Apr 24, 2026

6846 Helmsley Cir, Windermere, FL 34786
- 5 Beds
- 3 Baths
- 2,555 Sq Ft
- Built 2009
Last Sold Summary
- 11% Below List Price
- $243/SF
- 154 Days On Market
Current Estimated Value $619,191

Last Listing Agent Nickolas Amburgey COMPASS FLORIDA LLC

6846 Helmsley Cir, Windermere, FL 34786
/2
$1,318,000

Sold May 01, 2026

1625 Down Lake Dr, Windermere, FL 34786
- 5 Beds
- 5.5 Baths
- 3,383 Sq Ft
- Built 1984
Last Sold Summary
- 6% Below List Price
- $390/SF
- 48 Days On Market
Current Estimated Value $1,366,171

Last Listing Agent Cindy Rosenbloom THE ROSENBLOOM TEAM

1625 Down Lake Dr, Windermere, FL 34786
/2
$2,404,000

Sold Jan 15, 2026

1724 Windermeredown Place, Windermere, FL 34786
- 6 Beds
- 6.5 Baths
- 6,000 Sq Ft
- Built 1995
Last Sold Summary
- 4% Below List Price
- $401/SF
- 46 Days On Market
Current Estimated Value $2,359,045

Last Listing Agent Chad Going SERHANT

1724 Windermeredown Place, Windermere, FL 34786
/2
$1,655,000

Sold Aug 15, 2025

1424 Kelso Blvd, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 3,104 Sq Ft
- Built 1975
Last Sold Summary
- 12% Below List Price
- $533/SF
- 112 Days On Market
Current Estimated Value $1,751,336

Last Listing Agent Carmen Aridas RE/MAX PRIME PROPERTIES

1424 Kelso Blvd, Windermere, FL 34786
/2
$718,000

Sold Oct 20, 2025

12755 Westside Village Loop, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,064 Sq Ft
- Built 2018
Last Sold Summary
- 12% Below List Price
- $234/SF
- 142 Days On Market
Current Estimated Value $734,884

Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

12755 Westside Village Loop, Windermere, FL 34786
/2
$825,000

Sold Feb 11, 2026

1735 Maple Leaf Dr, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,771 Sq Ft
- Built 1989
Last Sold Summary
- 3% Below List Price
- $298/SF
- 3 Days On Market
Current Estimated Value $825,460

Last Listing Agent Frank Del Toro REVEL REALTY LLC

1735 Maple Leaf Dr, Windermere, FL 34786
/2
$1,500,000

Sold Apr 29, 2026

11821 Waterstone Loop Dr, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 3,447 Sq Ft
- Built 2012
Last Sold Summary
- 3% Below List Price
- $435/SF
- 7 Days On Market
Current Estimated Value $1,514,934

Last Listing Agent Mauricio Penha VOLKE REAL ESTATE LLC

11821 Waterstone Loop Dr, Windermere, FL 34786
/2
$535,000

Sold Jun 18, 2026

11486 Misty Oak Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,950 Sq Ft
- Built 2016
Last Sold Summary
- 3% Below List Price
- $274/SF
- 24 Days On Market
Current Estimated Value $544,902

Last Listing Agent Kikuko Moribe CENTURY 21 CARIOTI

11486 Misty Oak Aly, Windermere, FL 34786
/2
$966,400

Sold Oct 17, 2025

11508 Delwick Dr, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 3,206 Sq Ft
- Built 2003
Last Sold Summary
- 12% Below List Price
- $301/SF
- 144 Days On Market
Current Estimated Value $959,324

Last Listing Agent Ziad El Aryan FLORIDA REALTY INVESTMENTS

11508 Delwick Dr, Windermere, FL 34786
/2
$1,699,000

Sold Mar 10, 2026

13120 Zori Ln, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 4,329 Sq Ft
- Built 2005
Last Sold Summary
- $392/SF
- 2 Days On Market
Current Estimated Value $1,678,701

Last Listing Agent Matt Tomaszewski CORCORAN PREMIER REALTY

13120 Zori Ln, Windermere, FL 34786
/2
$1,650,000

Sold Feb 17, 2026

9922 Brentford Ct, Windermere, FL 34786
- 6 Beds
- 4 Baths
- 3,894 Sq Ft
- Built 2000
Last Sold Summary
- 13% Below List Price
- $424/SF
- 164 Days On Market
Current Estimated Value $1,677,475

Last Listing Agent Shane Croft COLDWELL BANKER REALTY

9922 Brentford Ct, Windermere, FL 34786
/2
$730,000

Sold Aug 15, 2025

9025 Horizon Pointe Trail, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,264 Sq Ft
- Built 2014
Last Sold Summary
- 1% Below List Price
- $224/SF
- 19 Days On Market
Current Estimated Value $737,679

Last Listing Agent Erin Fang FLORIDA REALTY INVESTMENTS

9025 Horizon Pointe Trail, Windermere, FL 34786
/34
$370,000

Sold Jul 01, 2026

14215 Desert Haven St, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,028 Sq Ft
- Built 2012
Last Sold Summary
- 5% Below List Price
- $182/SF
- 24 Days On Market
Last Listing Agent Brandi Crain Iron Valley R.E.Osceola

14215 Desert Haven St, Windermere, FL 34786
/2
$330,000

Sold Oct 22, 2025

11565 Mizzon Dr Unit 208, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
- Built 2006
Last Sold Summary
- 6% Below List Price
- $229/SF
- 10 Days On Market
Current Estimated Value $322,270

Last Listing Agent Gisele Abrantes Trautman LARTOK LLC

11565 Mizzon Dr Unit 208, Windermere, FL 34786
/2
$2,335,000

Sold Jun 10, 2026

105 Pine St, Windermere, FL 34786
- 5 Beds
- 5.5 Baths
- 5,696 Sq Ft
- Built 2015
Last Sold Summary
- 7% Below List Price
- $410/SF
- 9 Days On Market
Current Estimated Value $2,291,802

Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

105 Pine St, Windermere, FL 34786
/2
$485,000

Sold Sep 24, 2025

7837 Berkshire Oak Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,904 Sq Ft
- Built 2018
Last Sold Summary
- 1% Below List Price
- $255/SF
- 3 Days On Market
Current Estimated Value $494,642

Last Listing Agent Cara Edwards ALL REAL ESTATE & INVESTMENTS

7837 Berkshire Oak Aly, Windermere, FL 34786
/2
$1,050,000

Sold Oct 31, 2025

65 Oakdale St, Windermere, FL 34786
- 4 Beds
- 2 Baths
- 2,191 Sq Ft
- Built 1959
Last Sold Summary
- 12% Below List Price
- $479/SF
- 34 Days On Market
Current Estimated Value $1,085,749

Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

65 Oakdale St, Windermere, FL 34786

Showing Results 1 - 40, Page 1 of 17

Florida Orange County Windermere

Frequently Asked Questions

What is the average home price in Windermere, FL?

Homes for sale in Windermere, FL have an average home price of $1,628,526.

What is the average time to sell a house in Windermere, FL?

The houses for sale in Windermere, FL spend an average of 69 days on the market.

What is the number of active homes for sale in Windermere, FL?

There are 250 active homes for sale in Windermere, FL.

How many homes have sold over the last 12 months in Windermere, FL?

681 homes have sold in Windermere, FL over the last 12 months.

Home Prices in Windermere, FL

The median home sale price in Windermere, FL is $831,000, down 2% year-over-year. Homes in Windermere sell in 69 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price $831,000	Median Single Family Sale Price $1,084,779
Median Townhouse Sale Price $390,000	Median 2 Bedroom Sale Price $350,000
Average Price Per Sq Ft $366	Number of Homes for Sale 250
Last 12 months Home Sales 681	Months of Supply 4.40
Median List Price $950,000	Median Change From 1st List Price 5%
Median Home Sale Price YoY Change -2%

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Windermere Types of Homes for Sale

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