Recently Sold Winter Park Homes

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$710,000

Sold Jun 23, 2026

1108 Fairway Dr, Winter Park, FL 32792
- 3 Beds
- 2 Baths
- 1,677 Sq Ft
- Built 1978
Last Sold Summary
- 2% Below List Price
- $423/SF
- 82 Days On Market
Current Estimated Value $705,334

Last Listing Agent Rene Droz, III CHARLES RUTENBERG REALTY ORLANDO

1108 Fairway Dr, Winter Park, FL 32792
Explore Winter Park
/2
$1,965,000

Sold Jul 29, 2026

2261 Mulbry Dr, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 3,696 Sq Ft
- Built 2020
Last Sold Summary
- 2% Below List Price
- $532/SF
- 28 Days On Market
Current Estimated Value $1,868,808

Last Listing Agent Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

2261 Mulbry Dr, Winter Park, FL 32789
/2
$955,000

Sold Feb 24, 2026

512 Clarendon Ave, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,824 Sq Ft
- Built 2001
Last Sold Summary
- 3% Below List Price
- $338/SF
- 21 Days On Market
Current Estimated Value $954,693

Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

512 Clarendon Ave, Winter Park, FL 32789
/2
$6,000,000

Sold Dec 19, 2025

1920 Lakeside Dr, Orlando, FL 32803
- 5 Beds
- 5.5 Baths
- 5,964 Sq Ft
- Built 2020
Last Sold Summary
- 5% Below List Price
- $1,006/SF
- 12 Days On Market
Current Estimated Value $6,120,433

Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

1920 Lakeside Dr, Orlando, FL 32803
/2
$449,000

Sold Aug 12, 2026

2611 Lotafun Ave, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,838 Sq Ft
- Built 1962
Last Sold Summary
- $244/SF
- 3 Days On Market
Current Estimated Value $482,926

Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

2611 Lotafun Ave, Winter Park, FL 32789
/2
$2,295,000

Sold Dec 16, 2025

1661 Palm Ave, Winter Park, FL 32789
- 4 Beds
- 6 Baths
- 3,570 Sq Ft
- Built 2025
Last Sold Summary
- 12% Below List Price
- $643/SF
- 26 Days On Market
Current Estimated Value $2,188,495

Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

1661 Palm Ave, Winter Park, FL 32789
/2
$2,700,000

Sold Oct 30, 2025

1020 Mayfield Ave, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 2,663 Sq Ft
- Built 1989
Last Sold Summary
- 15% Below List Price
- $1,014/SF
- 149 Days On Market
Current Estimated Value $2,827,570

Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

1020 Mayfield Ave, Winter Park, FL 32789
/2
$714,000

Sold Mar 12, 2026

636 Dunblane Dr, Winter Park, FL 32792
- 3 Beds
- 2 Baths
- 1,803 Sq Ft
- Built 1962
Last Sold Summary
- 2% Below List Price
- $396/SF
- 7 Days On Market
Current Estimated Value $709,590

Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

636 Dunblane Dr, Winter Park, FL 32792
/2
$638,250

Sold Sep 02, 2025

1536 Golfside Dr, Winter Park, FL 32792
- 3 Beds
- 2 Baths
- 1,888 Sq Ft
- Built 1980
Last Sold Summary
- $338/SF
- 3 Days On Market
Current Estimated Value $653,104

Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

1536 Golfside Dr, Winter Park, FL 32792
/2
$401,000

Sold Oct 15, 2025

1809 Palmer Ave, Winter Park, FL 32792
- Land
- 9,147 Sq Ft
- $1,909,524 per Acre
Last Sold Summary
- 5 Days On Market
Current Estimated Value $406,555

Last Listing Agent Christina Munkberg COLDWELL BANKER REALTY

1809 Palmer Ave, Winter Park, FL 32792
/2
$4,250,000

Sold Jun 01, 2026

1336 College Point, Winter Park, FL 32789
- 4 Beds
- 5 Baths
- 3,181 Sq Ft
- Built 1926
Last Sold Summary
- 8% Below List Price
- $1,336/SF
- 109 Days On Market
Current Estimated Value $4,173,530

Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

1336 College Point, Winter Park, FL 32789
/2
$270,000

Sold Aug 14, 2026

1927 Diamond Dr, Orlando, FL 32807
- 3 Beds
- 2 Baths
- 1,616 Sq Ft
- Built 1971
Last Sold Summary
- 10% Below List Price
- $167/SF
- 0 Days On Market
Current Estimated Value $361,743

Last Listing Agent Debbi Jones COLDWELL BANKER REALTY

1927 Diamond Dr, Orlando, FL 32807
/2
$730,000

Sold Mar 23, 2026

1213 Lindenwood Ln, Winter Park, FL 32792
- 4 Beds
- 2 Baths
- 2,505 Sq Ft
- Built 1960
Last Sold Summary
- 3% Below List Price
- $291/SF
- 81 Days On Market
Current Estimated Value $727,395

Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

1213 Lindenwood Ln, Winter Park, FL 32792
/2
$1,590,000

Sold Mar 06, 2026

1166 Oaks Blvd, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,860 Sq Ft
- Built 2018
Last Sold Summary
- 12% Below List Price
- $556/SF
- 153 Days On Market
Current Estimated Value $1,620,787

Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

1166 Oaks Blvd, Winter Park, FL 32789
/2
$2,050,000

Sold Apr 30, 2026

1205 Mayfield Ave, Winter Park, FL 32789
- Land
- 23,958 Sq Ft
- $3,727,273 per Acre
Last Sold Summary
- 18% Below List Price
- 89 Days On Market
Current Estimated Value $2,147,768

Last Listing Agent Abby Nelson RE/MAX 200 REALTY

1205 Mayfield Ave, Winter Park, FL 32789
/2
$261,000

Sold May 13, 2026

1500 Gay Rd Unit 8D, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
- Built 1972
Last Sold Summary
- 2% Below List Price
- $254/SF
- 19 Days On Market
Current Estimated Value $260,275

Last Listing Agent Trevor Laug. Realtor SOLID OAK REAL ESTATE LLC

1500 Gay Rd Unit 8D, Winter Park, FL 32789
/2
$800,000

Sold Apr 30, 2026

737 N Capen Ave, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,930 Sq Ft
- Built 2021
Last Sold Summary
- 13% Below List Price
- $415/SF
- 99 Days On Market
Current Estimated Value $832,601

Last Listing Agent Jenn Carlisle LPT REALTY, LLC

737 N Capen Ave, Winter Park, FL 32789
/2
$640,000

Sold Jun 05, 2026

352 Cambridge Blvd, Winter Park, FL 32789
- 5 Beds
- 3 Baths
- 1,917 Sq Ft
- Built 1920
Last Sold Summary
- 2% Below List Price
- $334/SF
- 46 Days On Market
Current Estimated Value $628,676

Last Listing Agent Karen Jacobs COLDWELL BANKER REALTY

352 Cambridge Blvd, Winter Park, FL 32789
/2
$315,000

Sold Jan 01, 2026

615 Warrenton Rd, Winter Park, FL 32792
- 2 Beds
- 2 Baths
- 1,221 Sq Ft
- Built 1984
Last Sold Summary
- 2% Below List Price
- $258/SF
- 50 Days On Market
Current Estimated Value $323,975

Last Listing Agent Bryan Burns RE/MAX DOWNTOWN

615 Warrenton Rd, Winter Park, FL 32792
/2
$699,000

Sold Jul 09, 2026

676 Dunblane Dr, Winter Park, FL 32792
- 3 Beds
- 2 Baths
- 1,827 Sq Ft
- Built 1962
Last Sold Summary
- 7% Below List Price
- $383/SF
- 172 Days On Market
Current Estimated Value $689,250

Last Listing Agent Emma Kaplan BALDWIN PARK REALTY LLC

676 Dunblane Dr, Winter Park, FL 32792
/2
$325,000

Sold Dec 30, 2025

520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,160 Sq Ft
- Built 1986
Last Sold Summary
- 7% Below List Price
- $280/SF
- 6 Days On Market
Current Estimated Value $321,938

Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
/2
$6,200,000

Sold Aug 21, 2026

550 Palmer Ave, Winter Park, FL 32789
- 5 Beds
- 6.5 Baths
- 5,939 Sq Ft
- Built 2025
Last Sold Summary
- 14% Below List Price
- $1,044/SF
- 285 Days On Market
Current Estimated Value $5,859,205

Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

550 Palmer Ave, Winter Park, FL 32789
/2
$720,000

Sold Jan 20, 2026

2955 Lolissa Ln, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 3,538 Sq Ft
- Built 1969
Last Sold Summary
- 4% Below List Price
- $204/SF
- 47 Days On Market
Current Estimated Value $784,995

Last Listing Agent Catherine Williams COLDWELL BANKER REALTY

2955 Lolissa Ln, Winter Park, FL 32789
/2
$2,285,000

Sold Nov 19, 2025

521 S Phelps Ave, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 3,883 Sq Ft
- Built 2015
Last Sold Summary
- 7% Below List Price
- $588/SF
- 118 Days On Market
Current Estimated Value $2,398,900

Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

521 S Phelps Ave, Winter Park, FL 32789
/2
$350,000

Sold May 22, 2026

989 Eastbrook Blvd, Winter Park, FL 32792
- 3 Beds
- 1.5 Baths
- 1,140 Sq Ft
- Built 1959
Last Sold Summary
- 3% Below List Price
- $307/SF
- 35 Days On Market
Current Estimated Value $347,400

Last Listing Agent Jane Pedigree COLDWELL BANKER REALTY

989 Eastbrook Blvd, Winter Park, FL 32792
/2
$290,000

Sold Nov 24, 2025

2411 Gallery View Dr Unit 5, Winter Park, FL 32792
- 2 Beds
- 2 Baths
- 1,004 Sq Ft
- Built 1985
Last Sold Summary
- 9% Below List Price
- $289/SF
- 54 Days On Market
Current Estimated Value $298,424

Last Listing Agent Maria Elena Perez MEP REALTY INVESTMENTS LLC

2411 Gallery View Dr Unit 5, Winter Park, FL 32792
/2
$180,000

Sold Feb 27, 2026

200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
- 2 Beds
- 2 Baths
- 987 Sq Ft
- Built 1970
Last Sold Summary
- 8% Below List Price
- $182/SF
- 11 Days On Market
Current Estimated Value $184,713

Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
/2
$115,000

Sold May 08, 2026

1000 S Semoran Blvd Unit 512, Winter Park, FL 32792
- 2 Beds
- 2 Baths
- 1,072 Sq Ft
- Built 1969
Last Sold Summary
- 11% Below List Price
- $107/SF
- 41 Days On Market
Current Estimated Value $120,573

Last Listing Agent Cristina Burgos REALSOURCE PROPERTY MANGNT LLC

1000 S Semoran Blvd Unit 512, Winter Park, FL 32792
/2
$4,772,500

Sold Sep 18, 2025

765 Via Lugano, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 4,319 Sq Ft
- Built 2019
Last Sold Summary
- $1,105/SF
- 1 Day On Market
Current Estimated Value $4,888,049

Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

765 Via Lugano, Winter Park, FL 32789
/2
$840,000

Sold Nov 12, 2025

2604 Marble Ave, Orlando, FL 32803
- 5 Beds
- 4 Baths
- 3,424 Sq Ft
- Built 2007
Last Sold Summary
- 10% Below List Price
- $245/SF
- 102 Days On Market
Current Estimated Value $934,432

Last Listing Agent Brian Spain LAKESIDE REALTY

2604 Marble Ave, Orlando, FL 32803
/2
$2,700,000

Sold Oct 02, 2025

1445 Holts Grove Cir, Winter Park, FL 32789
- 5 Beds
- 5 Baths
- 4,489 Sq Ft
- Built 2002
Last Sold Summary
- 2% Above List Price
- $601/SF
- 2 Days On Market
Current Estimated Value $2,761,734

Last Listing Agent Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

1445 Holts Grove Cir, Winter Park, FL 32789
/2
$660,000

Sold Nov 17, 2025

2421 Summerfield Rd, Winter Park, FL 32792
- 4 Beds
- 2 Baths
- 2,256 Sq Ft
- Built 1968
Last Sold Summary
- 2% Above List Price
- $293/SF
- 6 Days On Market
Current Estimated Value $676,054

Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

2421 Summerfield Rd, Winter Park, FL 32792
/2
$3,485,000

Sold Oct 17, 2025

2171 Forrest Rd, Winter Park, FL 32789
- 5 Beds
- 6 Baths
- 4,565 Sq Ft
- Built 2016
Last Sold Summary
- 9% Below List Price
- $763/SF
- 134 Days On Market
Current Estimated Value $3,521,934

Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

2171 Forrest Rd, Winter Park, FL 32789
/71
$1,000,000

Sold Apr 01, 2026

2607 Lafayette Ave, Winter Park, FL 32789
- 4 Beds
- 3.5 Baths
- 2,770 Sq Ft
- Built 2018
Last Sold Summary
- 15% Below List Price
- $361/SF
- 244 Days On Market
Current Estimated Value $1,053,677

Last Listing Agent James Coombs Fortune Christie's International Real Estate

2607 Lafayette Ave, Winter Park, FL 32789
/2
$420,000

Sold Sep 12, 2025

1905 Diamond Dr, Orlando, FL 32807
- 4 Beds
- 2 Baths
- 1,660 Sq Ft
- Built 1972
Last Sold Summary
- 7% Below List Price
- $253/SF
- 172 Days On Market
Current Estimated Value $424,397

Last Listing Agent John Walker, Jr HOUWZER INC

1905 Diamond Dr, Orlando, FL 32807
/2
$530,000

Sold Aug 31, 2026

2552 Brookshire Ave, Winter Park, FL 32792
- 3 Beds
- 1.5 Baths
- 1,314 Sq Ft
- Built 1959
Last Sold Summary
- $403/SF
- 3 Days On Market
Current Estimated Value $528,189

Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES

2552 Brookshire Ave, Winter Park, FL 32792
/2
$1,905,000

Sold Apr 10, 2026

501 Henkel Cir, Winter Park, FL 32789
- 5 Beds
- 4.5 Baths
- 3,746 Sq Ft
- Built 2009
Last Sold Summary
- 4% Above List Price
- $509/SF
- 4 Days On Market
Current Estimated Value $1,956,262

Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

501 Henkel Cir, Winter Park, FL 32789
/2
$420,000

Sold Jan 15, 2026

1847 Azalea Ave, Winter Park, FL 32789
- 4 Beds
- 2.5 Baths
- 1,477 Sq Ft
- Built 1961
Last Sold Summary
- $284/SF
- 1 Day On Market
Current Estimated Value $424,431

Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

1847 Azalea Ave, Winter Park, FL 32789
/2
$199,900

Sold Nov 03, 2025

2500 Lee Rd Unit 134, Winter Park, FL 32789
- 1 Bed
- 1 Bath
- 645 Sq Ft
- Built 1969
Last Sold Summary
- 5% Below List Price
- $310/SF
- 130 Days On Market
Current Estimated Value $185,870

Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

2500 Lee Rd Unit 134, Winter Park, FL 32789
/2
$266,000

Sold Nov 19, 2025

1500 Gay Rd Unit 9B, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
- Built 1972
Last Sold Summary
- 1% Below List Price
- $259/SF
- 5 Days On Market
Current Estimated Value $255,091

Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

1500 Gay Rd Unit 9B, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 17

Florida Orange County Winter Park

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Frequently Asked Questions

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

The houses for sale in Winter Park, FL spend an average of 72 days on the market.

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

There are 234 active homes for sale in Winter Park, FL.

Is Winter Park, FL a good neighborhood?

Winter Park, FL is a highly rated neighborhood receiving 4.3 stars from it's current and former residents.

Home Prices in Winter Park, FL

The median home sale price in Winter Park, FL is $669,250, down 1% year-over-year. Homes in Winter Park sell in 72 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $669,250	Median Single Family Sale Price $899,000
Median Townhouse Sale Price $660,000	Median 2 Bedroom Sale Price $312,500
Median 1 Bedroom Sale Price $167,000	Average Price Per Sq Ft $446
Number of Homes for Sale 234	Last 12 months Home Sales 652
Months of Supply 4.30	Median List Price $750,000
Median Change From 1st List Price 5%	Median Home Sale Price YoY Change -1%

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