1,102

Recently Sold Winter Park, FL Homes

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  • /2

    $260,000

    Sold Jan 20, 2026

    2489 Tahoe Cir Unit 2489, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $198/SF
    • 87 Days On Market

    Current Estimated Value $261,665

    Last Listing Agent Kim James CHARLES RUTENBERG REALTY ORLANDO

    2489 Tahoe Cir Unit 2489, Winter Park, FL 32792
  • /2

    $399,000

    Sold Jun 30, 2026

    2808 Bright Bird Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft
    • Built 2024

    Last Sold Summary

    • $209/SF
    • 8 Days On Market

    Current Estimated Value $401,485

    Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

    2808 Bright Bird Ln, Winter Park, FL 32792
  • /2

    $1,201,000

    Sold Jun 18, 2026

    1723 Chestnut Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,608 Sq Ft
    • Built 1962

    Last Sold Summary

    • 7% Above List Price
    • $461/SF
    • 1 Day On Market

    Current Estimated Value $1,160,453

    Last Listing Agent Anne Rogers ANNE ROGERS REALTY GROUP INC

    1723 Chestnut Ave, Winter Park, FL 32789
  • /2

    $345,000

    Sold Jul 17, 2026

    2889 Rouen Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft
    • Built 1959

    Last Sold Summary

    • 14% Below List Price
    • $302/SF
    • 64 Days On Market

    Current Estimated Value $365,988

    Last Listing Agent Dan Farber HELLOSOLD LLC

    2889 Rouen Ave, Winter Park, FL 32789
  • /2

    $207,000

    Sold Jun 26, 2026

    5454 Bracken Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Above List Price
    • $155/SF
    • 0 Days On Market

    Current Estimated Value $225,372

    Last Listing Agent Mark Ramey EXP REALTY LLC

    5454 Bracken Ct, Winter Park, FL 32792
  • /2

    $420,000

    Sold Jun 11, 2026

    1611 Little Wren Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft
    • Built 2020

    Last Sold Summary

    • 1% Above List Price
    • $239/SF
    • 3 Days On Market

    Current Estimated Value $419,944

    Last Listing Agent Chris Winn BLOOM HOME GROUP REALTY LLC

    1611 Little Wren Ln, Winter Park, FL 32792
  • /2

    $6,500,000

    Sold Jul 31, 2026

    405 Lakewood Dr, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 4,208 Sq Ft
    • Built 2008

    Last Sold Summary

    • 3% Below List Price
    • $1,545/SF
    • 0 Days On Market

    Current Estimated Value $3,954,691

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    405 Lakewood Dr, Winter Park, FL 32789
  • /2

    $630,000

    Sold Oct 03, 2025

    1015 Bungalow Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • Built 2012

    Last Sold Summary

    • $377/SF
    • 2 Days On Market

    Current Estimated Value $679,965

    Last Listing Agent David Francetic COLDWELL BANKER REALTY

    1015 Bungalow Ave, Winter Park, FL 32789
  • /2

    $105,000

    Sold Jun 30, 2026

    1695 Lee Rd Unit E116, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,149 Sq Ft
    • Built 1966

    Last Sold Summary

    • 16% Below List Price
    • $91/SF
    • 36 Days On Market

    Current Estimated Value $119,640

    Last Listing Agent Cara Edwards ALL REAL ESTATE & INVESTMENTS

    1695 Lee Rd Unit E116, Winter Park, FL 32789
  • /2

    $455,500

    Sold Oct 16, 2025

    1317 Medinah Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,015 Sq Ft
    • Built 1979

    Last Sold Summary

    • 9% Below List Price
    • $226/SF

    Current Estimated Value $734,934

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    1317 Medinah Ct, Winter Park, FL 32792
  • /2

    $1,575,000

    Sold Jan 20, 2026

    1780 Mizell Ave, Winter Park, FL 32789

    • 4 Beds
    • 4 Baths
    • 2,743 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $574/SF
    • 0 Days On Market

    Current Estimated Value $1,511,187

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    1780 Mizell Ave, Winter Park, FL 32789
  • /2

    $4,550,000

    Sold Jun 05, 2026

    1701 Summerland Ave, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 5,253 Sq Ft
    • Built 2026

    Last Sold Summary

    • $866/SF
    • 0 Days On Market

    Current Estimated Value $3,546,904

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    1701 Summerland Ave, Winter Park, FL 32789
  • /2

    $3,100,000

    Sold Jul 06, 2026

    141 Glenridge Way, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 5,243 Sq Ft
    • Built 2008

    Last Sold Summary

    • 5% Below List Price
    • $591/SF
    • 49 Days On Market

    Current Estimated Value $3,200,100

    Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

    141 Glenridge Way, Winter Park, FL 32789
  • /2

    $1,825,000

    Sold Oct 16, 2025

    1361 Palmer Ave, Winter Park, FL 32789

    • 5 Beds
    • 3.5 Baths
    • 3,558 Sq Ft
    • Built 2005

    Last Sold Summary

    • 22% Below List Price
    • $513/SF
    • 121 Days On Market

    Current Estimated Value $1,865,432

    Last Listing Agent Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

    1361 Palmer Ave, Winter Park, FL 32789
  • /2

    $5,125,000

    Sold Jun 24, 2026

    1221 Richmond Rd, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 5,164 Sq Ft
    • Built 2024

    Last Sold Summary

    • 3% Above List Price
    • $992/SF
    • 3 Days On Market

    Current Estimated Value $3,943,761

    Last Listing Agent Christopher Salhab LA ROSA REALTY HORIZONS LLC

    1221 Richmond Rd, Winter Park, FL 32789
  • /2

    $775,000

    Sold Apr 05, 2026

    1770 Bryan Ave, Winter Park, FL 32789

    • Land
    • 8,276 Sq Ft
    • $4,078,947 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 142 Days On Market

    Current Estimated Value $780,000

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    1770 Bryan Ave, Winter Park, FL 32789
  • /2

    $163,000

    Sold Jul 20, 2026

    2923 Antique Oaks Cir Unit 39, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Built 1984

    Last Sold Summary

    • 29% Below List Price
    • $148/SF
    • 491 Days On Market

    Current Estimated Value $187,071

    Last Listing Agent Michell Carrasquero GLOBALWIDE REALTY LLC

    2923 Antique Oaks Cir Unit 39, Winter Park, FL 32792
  • /2

    $450,000

    Sold May 13, 2026

    518 Shoreview Ave, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,609 Sq Ft
    • Built 1920

    Last Sold Summary

    • 10% Above List Price
    • $280/SF
    • 14 Days On Market

    Current Estimated Value $447,642

    Last Listing Agent Kendra Wallace UNITED REAL ESTATE PREFERRED

    518 Shoreview Ave, Winter Park, FL 32789
  • /2

    $2,550,000

    Sold Aug 15, 2025

    1400 Place Picardy, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,338 Sq Ft
    • Built 2008

    Last Sold Summary

    • 10% Below List Price
    • $588/SF
    • 82 Days On Market

    Current Estimated Value $2,617,381

    Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

    1400 Place Picardy, Winter Park, FL 32789
  • /36

    $1,100,000

    Sold Oct 08, 2025

    930 S Kentucky Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,495 Sq Ft
    • Built 2014

    Last Sold Summary

    • $441/SF
    • 4 Days On Market

    Current Estimated Value $1,135,442

    Last Listing Agent Debi Callahan Adams, Cameron & Co., Realtors

    930 S Kentucky Ave, Winter Park, FL 32789
  • /2

    $160,000

    Sold Mar 24, 2026

    3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Built 1990

    Last Sold Summary

    • 3% Below List Price
    • $190/SF
    • 12 Days On Market

    Current Estimated Value $177,239

    Last Listing Agent Kirsten Weir PARK VIEW REALTY INC

    3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792
  • /2

    $4,300,000

    Sold May 29, 2026

    1760 Via Venetia, Winter Park, FL 32789

    • 4 Beds
    • 6.5 Baths
    • 6,242 Sq Ft
    • Built 2013

    Last Sold Summary

    • 8% Below List Price
    • $689/SF
    • 19 Days On Market

    Current Estimated Value $4,413,917

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

    1760 Via Venetia, Winter Park, FL 32789
  • /2

    $475,000

    Sold Nov 14, 2025

    260 Orange Terrace Dr, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 1,330 Sq Ft
    • Built 1953

    Last Sold Summary

    • 1% Below List Price
    • $357/SF
    • 6 Days On Market

    Current Estimated Value $482,936

    Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

    260 Orange Terrace Dr, Winter Park, FL 32789
  • /2

    $549,000

    Sold Apr 02, 2026

    4033 Yacht Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,268 Sq Ft
    • Built 1977

    Last Sold Summary

    • $242/SF
    • 13 Days On Market

    Current Estimated Value $546,198

    Last Listing Agent Pam White COLDWELL BANKER REALTY

    4033 Yacht Ct, Winter Park, FL 32792
  • /2

    $485,000

    Sold Apr 02, 2026

    2809 Casa Aloma Way, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Below List Price
    • $298/SF
    • 22 Days On Market

    Current Estimated Value $483,888

    Last Listing Agent Curt Marksbury WATSON REALTY CORP., REALTORS

    2809 Casa Aloma Way, Winter Park, FL 32792
  • /2

    $180,000

    Sold Feb 18, 2026

    Unlisted Address

    • 3 Beds
    • 2 Baths
    • 1,686 Sq Ft
    • Built 1960

    Last Sold Summary

    • $107/SF
    • 0 Days On Market

    Current Estimated Value $236,556

    Last Listing Agent Dragana Todorovic ENGEL & VOLKERS NEW SMYRNA

    Unlisted Address
  • /2

    $795,000

    Sold May 08, 2026

    639 Friar Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,950 Sq Ft
    • Built 1967

    Last Sold Summary

    • $408/SF
    • 17 Days On Market

    Current Estimated Value $768,061

    Last Listing Agent Dianne Moore FLORIDA REALTY INVESTMENTS

    639 Friar Rd, Winter Park, FL 32792
  • /2

    $299,000

    Sold Jun 17, 2026

    2529 Windward Way, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Built 1977

    Last Sold Summary

    • $271/SF
    • 5 Days On Market

    Current Estimated Value $280,111

    Last Listing Agent Myriam Quintero MY Q REALTY, LLC

    2529 Windward Way, Winter Park, FL 32792
  • /2

    $505,000

    Sold Jan 05, 2026

    1651 N Park Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,263 Sq Ft
    • Built 1965

    Last Sold Summary

    • $400/SF
    • 0 Days On Market

    Current Estimated Value $532,340

    Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

    1651 N Park Ave, Winter Park, FL 32789
  • /2

    $119,000

    Sold Dec 08, 2025

    1000 S Semoran Blvd Unit 608, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,049 Sq Ft
    • Built 1969

    Last Sold Summary

    • 30% Below List Price
    • $113/SF
    • 155 Days On Market

    Current Estimated Value $127,172

    Last Listing Agent Maria Peralta CHARLES RUTENBERG REALTY ORLANDO

    1000 S Semoran Blvd Unit 608, Winter Park, FL 32792
  • /2

    $750,000

    Sold Jan 12, 2026

    1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,957 Sq Ft
    • Built 2007

    Last Sold Summary

    • 6% Below List Price
    • $383/SF
    • 84 Days On Market

    Current Estimated Value $772,189

    Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789
  • /2

    $270,000

    Sold Aug 28, 2025

    2426 Windward Way, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 932 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $290/SF
    • 50 Days On Market

    Current Estimated Value $270,212

    Last Listing Agent Kim Coburn RE/MAX TOWN & COUNTRY REALTY

    2426 Windward Way, Winter Park, FL 32792
  • /2

    $670,000

    Sold Jul 22, 2026

    505 Cornwall Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,813 Sq Ft
    • Built 1965

    Last Sold Summary

    • 1% Below List Price
    • $370/SF
    • 18 Days On Market

    Current Estimated Value $669,622

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    505 Cornwall Rd, Winter Park, FL 32792
  • /2

    $110,000

    Sold Apr 15, 2026

    1695 Lee Rd Unit E211, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Built 1966

    Last Sold Summary

    • 24% Below List Price
    • $125/SF
    • 117 Days On Market

    Current Estimated Value $113,413

    Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1

    1695 Lee Rd Unit E211, Winter Park, FL 32789
  • /2

    $724,900

    Sold Jul 13, 2026

    1340 Blue Stem Ln, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 2,587 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $280/SF
    • 156 Days On Market

    Current Estimated Value $728,817

    Last Listing Agent Beth Hobart MAINFRAME REAL ESTATE

    1340 Blue Stem Ln, Winter Park, FL 32792
  • /2

    $650,000

    Sold May 22, 2026

    638 Blairshire Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,701 Sq Ft
    • Built 1964

    Last Sold Summary

    • 2% Above List Price
    • $382/SF
    • 0 Days On Market

    Current Estimated Value $636,689

    Last Listing Agent Sharon Wainman REALTY ONE GROUP MVP

    638 Blairshire Cir, Winter Park, FL 32792
  • /2

    $230,000

    Sold Jun 09, 2026

    1250 S Denning Dr Unit 117, Winter Park, FL 32789

    • 2 Beds
    • 1.5 Baths
    • 908 Sq Ft
    • Built 1967

    Last Sold Summary

    • 4% Below List Price
    • $253/SF
    • 11 Days On Market

    Current Estimated Value $231,487

    Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    1250 S Denning Dr Unit 117, Winter Park, FL 32789
  • /2

    $625,000

    Sold Jun 11, 2026

    962 Aragon Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1996

    Last Sold Summary

    • 4% Above List Price
    • $372/SF
    • 1 Day On Market

    Current Estimated Value $616,534

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    962 Aragon Ave, Winter Park, FL 32789
  • /2

    $470,000

    Sold Jul 08, 2026

    1511 Gladiolas Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,594 Sq Ft
    • Built 1979

    Last Sold Summary

    • $295/SF
    • 2 Days On Market

    Current Estimated Value $467,189

    Last Listing Agent Richard Aybar KELLER WILLIAMS ADVANTAGE III

    1511 Gladiolas Dr, Winter Park, FL 32792
  • /2

    $285,000

    Sold Jun 29, 2026

    3159 Greenwood St, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,241 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Below List Price
    • $230/SF
    • 4 Days On Market

    Current Estimated Value $286,435

    Last Listing Agent Joe Pietzyk GLOBAL PROPERTIES SALES/MGMT

    3159 Greenwood St, Winter Park, FL 32792

Showing Results 561 - 600, Page 15 of 18

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