1,095

Recently Sold Winter Park, FL Homes

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  • 100 S Virginia Ave Unit 314, Winter Park, FL 32789
    100 S Virginia Ave Unit 314, Winter Park, FL 32789
    /2

    $1,129,000 Sold Dec 10, 2025

    100 S Virginia Ave Unit 314, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 2,615 Sq Ft
    • Built 2009

    Last Sold Summary

    • $432/SF
    • 4 Days On Market

    Current Estimated Value $1,126,567

    Last Listing Agent Julieta Knapp ACCUMARK PROPERTIES

    100 S Virginia Ave Unit 314, Winter Park, FL 32789
  • 300 Carolina Ave Unit 201, Winter Park, FL 32789
    300 Carolina Ave Unit 201, Winter Park, FL 32789
    /2

    $702,050 Sold Jan 23, 2026

    300 Carolina Ave Unit 201, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,305 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $538/SF
    • 19 Days On Market

    Last Listing Agent Teri Webster LPT REALTY, LLC

    300 Carolina Ave Unit 201, Winter Park, FL 32789
  • 426 S Lakemont Ave, Winter Park, FL 32792
    426 S Lakemont Ave, Winter Park, FL 32792
    /2

    $510,000 Sold Sep 24, 2025

    426 S Lakemont Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,656 Sq Ft
    • Built 1955

    Last Sold Summary

    • 10% Below List Price
    • $308/SF
    • 150 Days On Market

    Current Estimated Value $516,548

    Last Listing Agent Caroline Moffitt-Lawton KELLER WILLIAMS HERITAGE REALTY

    426 S Lakemont Ave, Winter Park, FL 32792
  • 843 W Swoope Ave, Winter Park, FL 32789
    843 W Swoope Ave, Winter Park, FL 32789
    /2

    $610,000 Sold Aug 11, 2025

    843 W Swoope Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1962

    Last Sold Summary

    • 10% Below List Price
    • $495/SF
    • 67 Days On Market

    Current Estimated Value $586,945

    Last Listing Agent Jean Chalifour COLDWELL BANKER REALTY

    843 W Swoope Ave, Winter Park, FL 32789
  • 5150 Old Howell Branch Rd, Winter Park, FL 32792
    5150 Old Howell Branch Rd, Winter Park, FL 32792
    /2

    $610,000 Sold Apr 09, 2026

    5150 Old Howell Branch Rd, Winter Park, FL 32792

    • 3 Beds
    • 1.5 Baths
    • 2,108 Sq Ft
    • Built 1964

    Last Sold Summary

    • 6% Below List Price
    • $289/SF
    • 168 Days On Market

    Last Listing Agent John Sadri JOHN SADRI & COMPANY

    5150 Old Howell Branch Rd, Winter Park, FL 32792
  • 7449 Restful St, Winter Park, FL 32792
    7449 Restful St, Winter Park, FL 32792
    /2

    $235,000 Sold Dec 11, 2025

    7449 Restful St, Winter Park, FL 32792

    • Land
    • 31,798 Sq Ft
    • $321,918 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 30 Days On Market

    Current Estimated Value $234,247

    Last Listing Agent Ray Al-Malt EXP REALTY LLC

    7449 Restful St, Winter Park, FL 32792
  • 3651 N Goldenrod Rd Unit 107, Winter Park, FL 32792
    3651 N Goldenrod Rd Unit 107, Winter Park, FL 32792
    /2

    $155,000 Sold Aug 06, 2025

    3651 N Goldenrod Rd Unit 107, Winter Park, FL 32792

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

    Last Sold Summary

    • 28% Below List Price
    • $185/SF
    • 388 Days On Market

    Last Listing Agent Veronica Figueroa EXP REALTY LLC

    3651 N Goldenrod Rd Unit 107, Winter Park, FL 32792
  • 1712 Golfside Dr, Winter Park, FL 32792
    1712 Golfside Dr, Winter Park, FL 32792
    /2

    $750,000 Sold Jan 08, 2026

    1712 Golfside Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,111 Sq Ft
    • Built 1979

    Last Sold Summary

    • $355/SF
    • 11 Days On Market

    Current Estimated Value $745,011

    Last Listing Agent Shawn McCormick ERA GRIZZARD REAL ESTATE

    1712 Golfside Dr, Winter Park, FL 32792
  • 2831 Lion Heart Rd, Winter Park, FL 32792
    2831 Lion Heart Rd, Winter Park, FL 32792
    /2

    $460,000 Sold Dec 05, 2025

    2831 Lion Heart Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft
    • Built 1963

    Last Sold Summary

    • 4% Below List Price
    • $233/SF
    • 35 Days On Market

    Current Estimated Value $467,936

    Last Listing Agent Joyce Tang JOY ESTATE ENTERPRISE INC

    2831 Lion Heart Rd, Winter Park, FL 32792
  • 5618 Winterbrook Way, Winter Park, FL 32792
    5618 Winterbrook Way, Winter Park, FL 32792
    /2

    $730,000 Sold Oct 07, 2025

    5618 Winterbrook Way, Winter Park, FL 32792

    • 5 Beds
    • 4 Baths
    • 2,866 Sq Ft
    • Built 2020

    Last Sold Summary

    • 14% Below List Price
    • $255/SF
    • 206 Days On Market

    Current Estimated Value $741,100

    Last Listing Agent Elizabeth Binder REDFIN CORPORATION

    5618 Winterbrook Way, Winter Park, FL 32792
  • 1660 Tremont Ln, Winter Park, FL 32792
    1660 Tremont Ln, Winter Park, FL 32792
    /2

    $450,000 Sold Oct 17, 2025

    1660 Tremont Ln, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,980 Sq Ft
    • Built 1986

    Last Sold Summary

    • $227/SF
    • 12 Days On Market

    Current Estimated Value $445,532

    Last Listing Agent Jason Howell REAL BROKER, LLC

    1660 Tremont Ln, Winter Park, FL 32792
  • 160 Moyses Rd, Winter Park, FL 32792
    160 Moyses Rd, Winter Park, FL 32792
    /2

    $780,000 Sold May 16, 2025

    160 Moyses Rd, Winter Park, FL 32792

    • 8 Beds
    • 8 Baths
    • 3,600 Sq Ft
    • Built 1979

    Last Sold Summary

    • $217/SF
    • 34 Days On Market

    Last Listing Agent Marybeth Brown FLORIDA ONE REAL ESTATE LLC

    160 Moyses Rd, Winter Park, FL 32792
  • 2065 Cocos Ln, Winter Park, FL 32792
    2065 Cocos Ln, Winter Park, FL 32792
    /2

    $357,500 Sold Nov 25, 2025

    2065 Cocos Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft
    • Built 1966

    Last Sold Summary

    • 1% Below List Price
    • $247/SF
    • 3 Days On Market

    Current Estimated Value $363,874

    Last Listing Agent Stacey Mortensen KELLER WILLIAMS REALTY AT THE PARKS

    2065 Cocos Ln, Winter Park, FL 32792
  • 141 Lewfield Cir Unit 141, Winter Park, FL 32792
    141 Lewfield Cir Unit 141, Winter Park, FL 32792
    /2

    $160,000 Sold Oct 28, 2025

    141 Lewfield Cir Unit 141, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 678 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Below List Price
    • $236/SF
    • 95 Days On Market

    Current Estimated Value $148,094

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

    141 Lewfield Cir Unit 141, Winter Park, FL 32792
  • 2008 Nottingdale Ln, Winter Park, FL 32792
    2008 Nottingdale Ln, Winter Park, FL 32792
    /2

    $365,000 Sold Sep 11, 2025

    2008 Nottingdale Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,278 Sq Ft
    • Built 1980

    Last Sold Summary

    • $286/SF
    • 9 Days On Market

    Current Estimated Value $361,225

    Last Listing Agent Robert Bretz, PA EXP REALTY LLC

    2008 Nottingdale Ln, Winter Park, FL 32792
  • 2412 Middleton Ave, Winter Park, FL 32792
    2412 Middleton Ave, Winter Park, FL 32792
    /2

    $500,000 Sold Jan 26, 2026

    2412 Middleton Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • Built 1959

    Last Sold Summary

    • 19% Below List Price
    • $373/SF
    • 54 Days On Market

    Last Listing Agent Santiago Borrero REAL ESTATE INVESTMENTS BY BOR

    2412 Middleton Ave, Winter Park, FL 32792
  • 690 Williams Dr, Winter Park, FL 32789
    690 Williams Dr, Winter Park, FL 32789
    /2

    $1,770,000 Sold Sep 22, 2025

    690 Williams Dr, Winter Park, FL 32789

    • 3 Beds
    • 4 Baths
    • 3,121 Sq Ft
    • Built 1962

    Last Sold Summary

    • 2% Below List Price
    • $567/SF
    • 0 Days On Market

    Current Estimated Value $1,761,863

    Last Listing Agent Tiffany Grindstaff KELLY PRICE & COMPANY LLC

    690 Williams Dr, Winter Park, FL 32789
  • 1700 Palm Ave, Winter Park, FL 32789
    1700 Palm Ave, Winter Park, FL 32789
    /2

    $2,440,000 Sold Jul 01, 2025

    1700 Palm Ave, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,770 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $647/SF
    • 41 Days On Market

    Current Estimated Value $2,438,265

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1700 Palm Ave, Winter Park, FL 32789
  • 513 Cornwall Rd, Winter Park, FL 32792
    513 Cornwall Rd, Winter Park, FL 32792
    /2

    $629,000 Sold Apr 03, 2026

    513 Cornwall Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,735 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Below List Price
    • $363/SF
    • 39 Days On Market

    Current Estimated Value $621,751

    Last Listing Agent Chad Isenhart PREMIER SOTHEBY'S INTL. REALTY

    513 Cornwall Rd, Winter Park, FL 32792
  • 1648 Cypress Point Ln, Winter Park, FL 32792
    1648 Cypress Point Ln, Winter Park, FL 32792
    /2

    $899,000 Sold Nov 21, 2025

    1648 Cypress Point Ln, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,455 Sq Ft
    • Built 1982

    Last Sold Summary

    • 3% Below List Price
    • $366/SF
    • 21 Days On Market

    Current Estimated Value $896,220

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    1648 Cypress Point Ln, Winter Park, FL 32792
  • 1705 Elizabeths Walk, Winter Park, FL 32789
    1705 Elizabeths Walk, Winter Park, FL 32789
    /2

    $1,688,750 Sold Apr 01, 2026

    1705 Elizabeths Walk, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 3,820 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Above List Price
    • $442/SF
    • 3 Days On Market

    Current Estimated Value $2,002,870

    Last Listing Agent Keith Moore HOMEVEST REALTY

    1705 Elizabeths Walk, Winter Park, FL 32789
  • 1802 Arbor Park Dr, Winter Park, FL 32789
    1802 Arbor Park Dr, Winter Park, FL 32789
    /2

    $895,000 Sold Dec 29, 2025

    1802 Arbor Park Dr, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 1,808 Sq Ft
    • Built 1968

    Last Sold Summary

    • $495/SF
    • 1 Day On Market

    Current Estimated Value $1,029,004

    Last Listing Agent Jennifer Roberts FLORIDA EXECUTIVE REALTY

    1802 Arbor Park Dr, Winter Park, FL 32789
  • 1604 Nottingham Dr, Winter Park, FL 32792
    1604 Nottingham Dr, Winter Park, FL 32792
    /2

    $420,000 Sold Jun 16, 2025

    1604 Nottingham Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,562 Sq Ft
    • Built 1970

    Last Sold Summary

    • 7% Below List Price
    • $269/SF
    • 15 Days On Market

    Current Estimated Value $432,407

    Last Listing Agent Keegan Siegfried LPT REALTY, LLC

    1604 Nottingham Dr, Winter Park, FL 32792
  • 633 Lander Rd, Winter Park, FL 32792
    633 Lander Rd, Winter Park, FL 32792
    /2

    $421,000 Sold Apr 29, 2026

    633 Lander Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1956

    Last Sold Summary

    • 1% Below List Price
    • $301/SF
    • 6 Days On Market

    Current Estimated Value $421,023

    Last Listing Agent Raymond Lopez KELLER WILLIAMS ADVANTAGE 2 REALTY

    633 Lander Rd, Winter Park, FL 32792
  • 2381 Roxbury Rd, Winter Park, FL 32789
    2381 Roxbury Rd, Winter Park, FL 32789
    /2

    $470,000 Sold Dec 23, 2025

    2381 Roxbury Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft
    • Built 1949

    Last Sold Summary

    • 8% Below List Price
    • $263/SF
    • 24 Days On Market

    Current Estimated Value $470,047

    Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

    2381 Roxbury Rd, Winter Park, FL 32789
  • 1394 Stewart St, Winter Park, FL 32789
    1394 Stewart St, Winter Park, FL 32789
    /2

    $1,942,000 Sold Jul 14, 2025

    1394 Stewart St, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 3,907 Sq Ft
    • Built 1961

    Last Sold Summary

    • 12% Below List Price
    • $497/SF
    • 50 Days On Market

    Current Estimated Value $1,928,367

    Last Listing Agent Richard Vaughn REALTY ONE GROUP INSPIRATION

    1394 Stewart St, Winter Park, FL 32789
  • 2880 Old Castle Dr, Winter Park, FL 32792
    2880 Old Castle Dr, Winter Park, FL 32792
    /2

    $1,010,000 Sold Sep 30, 2025

    2880 Old Castle Dr, Winter Park, FL 32792

    • 5 Beds
    • 4.5 Baths
    • 3,839 Sq Ft
    • Built 1993

    Last Sold Summary

    • 10% Below List Price
    • $263/SF
    • 90 Days On Market

    Current Estimated Value $1,040,169

    Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

    2880 Old Castle Dr, Winter Park, FL 32792
  • 1817 Jessica Ct, Winter Park, FL 32789
    1817 Jessica Ct, Winter Park, FL 32789
    /2

    $540,000 Sold Dec 29, 2025

    1817 Jessica Ct, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,870 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Above List Price
    • $289/SF
    • 3 Days On Market

    Current Estimated Value $548,679

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1817 Jessica Ct, Winter Park, FL 32789
  • 141 W Lake Sue Ave, Winter Park, FL 32789
    141 W Lake Sue Ave, Winter Park, FL 32789
    /2

    $1,450,000 Sold Mar 19, 2026

    141 W Lake Sue Ave, Winter Park, FL 32789

    • Land
    • 22,215 Sq Ft
    • $2,843,137 per Acre

    Last Sold Summary

    • 14% Below List Price
    • 137 Days On Market

    Current Estimated Value $1,460,259

    Last Listing Agent Brian Mitnik RE/MAX 200 REALTY

    141 W Lake Sue Ave, Winter Park, FL 32789
  • 100 S Interlachen Ave Unit 404, Winter Park, FL 32789
    100 S Interlachen Ave Unit 404, Winter Park, FL 32789
    /2

    $1,100,000 Sold Apr 15, 2026

    100 S Interlachen Ave Unit 404, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,220 Sq Ft
    • Built 1971

    Last Sold Summary

    • 8% Below List Price
    • $902/SF
    • 51 Days On Market

    Current Estimated Value $932,521

    Last Listing Agent Ruth Harris COLDWELL BANKER REALTY

    100 S Interlachen Ave Unit 404, Winter Park, FL 32789
  • 105 Conrad Ct, Winter Park, FL 32789
    105 Conrad Ct, Winter Park, FL 32789
    /2

    $429,999 Sold Oct 21, 2025

    105 Conrad Ct, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,573 Sq Ft
    • Built 1958

    Last Sold Summary

    • $273/SF
    • 24 Days On Market

    Current Estimated Value $436,778

    Last Listing Agent Pam Grabenhorst THE WILKINS WAY LLC

    105 Conrad Ct, Winter Park, FL 32789
  • 712 Baffie Ave, Winter Park, FL 32789
    712 Baffie Ave, Winter Park, FL 32789
    /2

    $292,000 Sold May 16, 2025

    712 Baffie Ave, Winter Park, FL 32789

    • 3 Beds
    • 1 Bath
    • 1,304 Sq Ft
    • Built 1925

    Last Sold Summary

    • 10% Below List Price
    • $224/SF
    • 7 Days On Market

    Current Estimated Value $318,985

    Last Listing Agent Bobby Livera BALDWIN PARK REALTY LLC

    712 Baffie Ave, Winter Park, FL 32789
  • 2817 Fitzooth Dr, Winter Park, FL 32792
    2817 Fitzooth Dr, Winter Park, FL 32792
    /2

    $600,000 Sold Jan 23, 2026

    2817 Fitzooth Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,619 Sq Ft
    • Built 1965

    Last Sold Summary

    • 6% Below List Price
    • $371/SF
    • 36 Days On Market

    Current Estimated Value $593,859

    Last Listing Agent Diego Trujillo-Castillo REALTY HUB

    2817 Fitzooth Dr, Winter Park, FL 32792
  • 7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792
    7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792
    /2

    $100,000 Sold Sep 09, 2025

    7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft
    • Built 1974

    Last Sold Summary

    • 8% Below List Price
    • $97/SF
    • 38 Days On Market

    Last Listing Agent Pedro Ramos ROCKER'S REAL ESTATE, LLC

    7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792
  • 1400 S Pennsylvania Ave, Winter Park, FL 32789
    1400 S Pennsylvania Ave, Winter Park, FL 32789
    /2

    $1,300,000 Sold Jan 02, 2026

    1400 S Pennsylvania Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,310 Sq Ft
    • Built 1962

    Last Sold Summary

    • 6% Below List Price
    • $563/SF
    • 333 Days On Market

    Current Estimated Value $1,261,348

    Last Listing Agent Jack Keller JACK KELLER INC

    1400 S Pennsylvania Ave, Winter Park, FL 32789
  • 1230 N Denning Dr, Winter Park, FL 32789
    1230 N Denning Dr, Winter Park, FL 32789
    /2

    $575,000 Sold May 27, 2025

    1230 N Denning Dr, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 972 Sq Ft
    • Built 1952

    Last Sold Summary

    • 3% Below List Price
    • $592/SF
    • 24 Days On Market

    Current Estimated Value $576,987

    Last Listing Agent Ed Klein FANNIE HILLMAN & ASSOCIATES

    1230 N Denning Dr, Winter Park, FL 32789
  • 620 Virginia Dr, Winter Park, FL 32789
    620 Virginia Dr, Winter Park, FL 32789
    /2

    $1,050,000 Sold Dec 05, 2025

    620 Virginia Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,577 Sq Ft
    • Built 1965

    Last Sold Summary

    • 6% Above List Price
    • $666/SF
    • 0 Days On Market

    Current Estimated Value $1,065,336

    Last Listing Agent Jason Gilkey GILKEY REAL ESTATE

    620 Virginia Dr, Winter Park, FL 32789
  • 887 Georgia Ave, Winter Park, FL 32789
    887 Georgia Ave, Winter Park, FL 32789
    /2

    $4,500,000 Sold Apr 30, 2026

    887 Georgia Ave, Winter Park, FL 32789

    • 6 Beds
    • 5.5 Baths
    • 5,759 Sq Ft
    • Built 1924

    Last Sold Summary

    • 31% Below List Price
    • $781/SF
    • 222 Days On Market

    Current Estimated Value $4,650,376

    Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

    887 Georgia Ave, Winter Park, FL 32789
  • 3053 George Mason Ave Unit 7, Winter Park, FL 32792
    3053 George Mason Ave Unit 7, Winter Park, FL 32792
    /2

    $75,000 Sold Nov 20, 2025

    3053 George Mason Ave Unit 7, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft
    • Built 1974

    Last Sold Summary

    • 25% Below List Price
    • $73/SF
    • 85 Days On Market

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    3053 George Mason Ave Unit 7, Winter Park, FL 32792
  • 1000 S Semoran Blvd Unit 415, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 415, Winter Park, FL 32792
    /2

    $110,000 Sold Sep 15, 2025

    1000 S Semoran Blvd Unit 415, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 735 Sq Ft
    • Built 1969

    Last Sold Summary

    • 18% Below List Price
    • $150/SF
    • 78 Days On Market

    Current Estimated Value $107,607

    Last Listing Agent Jhoana Loyo Urrutia LA ROSA REALTY LLC

    1000 S Semoran Blvd Unit 415, Winter Park, FL 32792

Showing Results 401 - 440, Page 11 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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