1,102

Recently Sold Winter Park, FL Homes

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  • /2

    $180,000

    Sold Jan 06, 2026

    2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,018 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $177/SF
    • 8 Days On Market

    Current Estimated Value $184,304

    Last Listing Agent Chris Bessette KELLER WILLIAMS CLASSIC

    2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792
  • /2

    $1,950,000

    Sold Sep 16, 2025

    141 Oakwood Way, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 3,909 Sq Ft
    • Built 2015

    Last Sold Summary

    • 14% Below List Price
    • $499/SF
    • 170 Days On Market

    Current Estimated Value $2,022,969

    Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

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

    $160,000

    Sold Jun 05, 2026

    2500 Lee Rd Unit 122, Winter Park, FL 32789

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

    Last Sold Summary

    • 11% Below List Price
    • $248/SF
    • 60 Days On Market

    Current Estimated Value $161,286

    Last Listing Agent Andrea Aylett-Hosch PINEAPPLE PLACE REALTY, LLC

    2500 Lee Rd Unit 122, Winter Park, FL 32789
  • /2

    $145,000

    Sold Apr 23, 2026

    2500 Lee Rd Unit 243, Winter Park, FL 32789

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

    Last Sold Summary

    • 28% Below List Price
    • $225/SF
    • 286 Days On Market

    Current Estimated Value $145,972

    Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

    2500 Lee Rd Unit 243, Winter Park, FL 32789
  • /2

    $850,000

    Sold Mar 31, 2026

    1929 S Lakemont Ave, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 2,160 Sq Ft
    • Built 2023

    Last Sold Summary

    • 10% Below List Price
    • $394/SF
    • 91 Days On Market

    Current Estimated Value $875,647

    Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

    1929 S Lakemont Ave, Winter Park, FL 32792
  • /2

    $912,500

    Sold Jan 14, 2026

    210 Laurel Park Ct, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,838 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Below List Price
    • $322/SF
    • 25 Days On Market

    Current Estimated Value $917,338

    Last Listing Agent Alireza Partovi EXP REALTY LLC

    210 Laurel Park Ct, Winter Park, FL 32792
  • /2

    $485,000

    Sold Aug 18, 2025

    1921 Japonica Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,171 Sq Ft
    • Built 1971

    Last Sold Summary

    • $223/SF
    • 11 Days On Market

    Current Estimated Value $505,866

    Last Listing Agent Jose Gabriel Rodriguez COLDWELL BANKER REALTY

    1921 Japonica Rd, Winter Park, FL 32792
  • /2

    $335,000

    Sold Oct 31, 2025

    3525 Baxter Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1970

    Last Sold Summary

    • 14% Above List Price
    • $215/SF
    • 5 Days On Market

    Current Estimated Value $338,173

    Last Listing Agent Ashley Fisak COLDWELL BANKER REALTY

    3525 Baxter Dr, Winter Park, FL 32792
  • /2

    $715,000

    Sold Jun 12, 2026

    688 Brechin Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,599 Sq Ft
    • Built 1961

    Last Sold Summary

    • 1% Below List Price
    • $447/SF
    • 3 Days On Market

    Current Estimated Value $712,580

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    688 Brechin Dr, Winter Park, FL 32792
  • /2

    $179,900

    Sold Jun 02, 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
    • $214/SF
    • 44 Days On Market

    Current Estimated Value $177,239

    Last Listing Agent REZA Shirzad ANNE ROGERS REALTY GROUP INC

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

    $893,000

    Sold Oct 09, 2025

    2890 Wild Ginger Ct, Winter Park, FL 32792

    • 4 Beds
    • 4.5 Baths
    • 3,408 Sq Ft
    • Built 1993

    Last Sold Summary

    • 27% Below List Price
    • $262/SF
    • 78 Days On Market

    Current Estimated Value $903,710

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    2890 Wild Ginger Ct, Winter Park, FL 32792
  • /2

    $800,200

    Sold Oct 03, 2025

    4107 Gabriella Ln, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,074 Sq Ft
    • Built 1998

    Last Sold Summary

    • 33% Below List Price
    • $260/SF
    • 112 Days On Market

    Current Estimated Value $934,837

    Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

    4107 Gabriella Ln, Winter Park, FL 32792
  • /2

    $405,500

    Sold May 28, 2026

    2834 Bright Bird Ln, Winter Park, FL 32792

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

    Last Sold Summary

    • 7% Below List Price
    • $213/SF
    • 108 Days On Market

    Current Estimated Value $405,497

    Last Listing Agent Irene Navarro LIFESTYLE INTERNATIONAL REALTY

    2834 Bright Bird Ln, Winter Park, FL 32792
  • /2

    $510,000

    Sold Jul 21, 2026

    641 W Lyman Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 2003

    Last Sold Summary

    • $455/SF
    • 12 Days On Market

    Current Estimated Value $547,708

    Last Listing Agent Ted Moseley REAL BROKER, LLC

    641 W Lyman Ave, Winter Park, FL 32789
  • /2

    $3,020,000

    Sold Oct 02, 2025

    1820 Englewood Rd, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,263 Sq Ft
    • Built 2015

    Last Sold Summary

    • 8% Below List Price
    • $708/SF
    • 70 Days On Market

    Current Estimated Value $3,087,570

    Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

    1820 Englewood Rd, Winter Park, FL 32789
  • /2

    $1,120,000

    Sold Jan 08, 2026

    5236 Lake Howell Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 3,710 Sq Ft
    • Built 2025

    Last Sold Summary

    • 23% Below List Price
    • $302/SF
    • 129 Days On Market

    Current Estimated Value $1,068,939

    Last Listing Agent Troy Hensley BHHS FLORIDA REALTY

    5236 Lake Howell Rd, Winter Park, FL 32792
  • /2

    $389,900

    Sold Mar 18, 2026

    700 Melrose Ave Unit M4, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,074 Sq Ft
    • Built 1964

    Last Sold Summary

    • 1% Below List Price
    • $363/SF
    • 7 Days On Market

    Current Estimated Value $377,531

    Last Listing Agent Mary Harmening ROAM FLORIDA REALTY LLC

    700 Melrose Ave Unit M4, Winter Park, FL 32789
  • /2

    $415,000

    Sold Jul 09, 2026

    1016 Manchester Cir, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft
    • Built 1976

    Last Sold Summary

    • 1% Below List Price
    • $255/SF
    • 3 Days On Market

    Current Estimated Value $414,385

    Last Listing Agent Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

    1016 Manchester Cir, Winter Park, FL 32792
  • /2

    $565,000

    Sold Jun 04, 2026

    1018 Bradford Dr, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 2,513 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Above List Price
    • $225/SF
    • 4 Days On Market

    Current Estimated Value $556,427

    Last Listing Agent Janie Harris UNITED REAL ESTATE PREFERRED

    1018 Bradford Dr, Winter Park, FL 32792
  • /2

    $260,000

    Sold Apr 03, 2026

    3580 Wilde Ave, Winter Park, FL 32792

    • Land
    • 35,283 Sq Ft
    • $320,988 per Acre

    Last Sold Summary

    • 340 Days On Market

    Current Estimated Value $261,729

    Last Listing Agent Gwendolen Flynn COLDWELL BANKER REALTY

    3580 Wilde Ave, Winter Park, FL 32792
  • /2

    $417,100

    Sold Nov 24, 2025

    690 Osceola Ave Unit 502, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1969

    Last Sold Summary

    • 26% Below List Price
    • $298/SF
    • 196 Days On Market

    Current Estimated Value $425,764

    Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

    690 Osceola Ave Unit 502, Winter Park, FL 32789
  • /2

    $435,800

    Sold Apr 27, 2026

    5418 Ardmore Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Below List Price
    • $279/SF
    • 5 Days On Market

    Current Estimated Value $436,346

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    5418 Ardmore Dr, Winter Park, FL 32792
  • /2

    $1,200,000

    Sold Mar 20, 2026

    950 Aragon Ave, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,592 Sq Ft
    • Built 2020

    Last Sold Summary

    • $463/SF
    • 5 Days On Market

    Current Estimated Value $1,197,659

    Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

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

    $1,206,400

    Sold Oct 15, 2025

    4048 Gilder Rose Place, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,321 Sq Ft
    • Built 1992

    Last Sold Summary

    • $363/SF
    • 101 Days On Market

    Current Estimated Value $1,186,317

    Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

    4048 Gilder Rose Place, Winter Park, FL 32792
  • /2

    $487,500

    Sold Mar 26, 2026

    275 N Ranger Blvd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,864 Sq Ft
    • Built 1965

    Last Sold Summary

    • 2% Below List Price
    • $262/SF
    • 2 Days On Market

    Current Estimated Value $725,777

    Last Listing Agent David Augello ON POINT REALTY LLC

    275 N Ranger Blvd, Winter Park, FL 32792
  • /2

    $630,000

    Sold Apr 16, 2026

    649 Berwick Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,943 Sq Ft
    • Built 1966

    Last Sold Summary

    • 3% Above List Price
    • $324/SF
    • 3 Days On Market

    Current Estimated Value $621,986

    Last Listing Agent Caroline Fiore MAINFRAME REAL ESTATE

    649 Berwick Dr, Winter Park, FL 32792
  • /2

    $168,500

    Sold Jul 02, 2026

    1500 Gay Rd Unit 5, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 732 Sq Ft
    • Built 1972

    Last Sold Summary

    • 14% Below List Price
    • $230/SF
    • 97 Days On Market

    Last Listing Agent Jacob Hara TRANSCEND REALTY

    1500 Gay Rd Unit 5, Winter Park, FL 32789
  • /2

    $625,090

    Sold Jun 03, 2026

    2713 Eastern Pkwy, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Below List Price
    • $479/SF
    • 12 Days On Market

    Current Estimated Value $645,250

    Last Listing Agent Helen Thompson RE/MAX SELECT GROUP

    2713 Eastern Pkwy, Winter Park, FL 32789
  • /2

    $637,500

    Sold Jan 16, 2026

    595 Huntington Ave Unit 4, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,951 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Below List Price
    • $327/SF
    • 149 Days On Market

    Current Estimated Value $638,985

    Last Listing Agent Andrew Livingston COLDWELL BANKER REALTY

    595 Huntington Ave Unit 4, Winter Park, FL 32789
  • /2

    $1,250,000

    Sold Dec 29, 2025

    359 Beloit Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,395 Sq Ft
    • Built 1979

    Last Sold Summary

    • $522/SF
    • 0 Days On Market

    Current Estimated Value $1,276,215

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    359 Beloit Ave, Winter Park, FL 32789
  • /2

    $775,000

    Sold May 22, 2026

    521 Fairfax Ave, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 2,112 Sq Ft
    • Built 1955

    Last Sold Summary

    • 2% Below List Price
    • $367/SF
    • 2 Days On Market

    Current Estimated Value $772,935

    Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

    521 Fairfax Ave, Winter Park, FL 32789
  • /2

    $1,199,000

    Sold Jun 09, 2026

    1807 Magnolia Ave, Winter Park, FL 32789

    • 5 Beds
    • 3 Baths
    • 2,618 Sq Ft
    • Built 2026

    Last Sold Summary

    • $458/SF
    • 9 Days On Market

    Current Estimated Value $1,140,096

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    1807 Magnolia Ave, Winter Park, FL 32789
  • /2

    $1,595,000

    Sold Sep 02, 2025

    1733 Harmon Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,267 Sq Ft
    • Built 2025

    Last Sold Summary

    • $488/SF
    • 27 Days On Market

    Current Estimated Value $1,703,811

    Last Listing Agent Jordan Freeland SOUTH REALTY, INC

    1733 Harmon Ave, Winter Park, FL 32789
  • /2

    $749,000

    Sold Aug 13, 2025

    627 Darcey Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,509 Sq Ft
    • Built 1967

    Last Sold Summary

    • 6% Below List Price
    • $299/SF
    • 52 Days On Market

    Current Estimated Value $787,810

    Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

    627 Darcey Dr, Winter Park, FL 32792
  • /2

    $1,095,000

    Sold Dec 01, 2025

    1450 Chestnut Ave, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 1,942 Sq Ft
    • Built 2009

    Last Sold Summary

    • 16% Below List Price
    • $564/SF
    • 49 Days On Market

    Current Estimated Value $1,130,622

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1450 Chestnut Ave, Winter Park, FL 32789
  • /2

    $220,000

    Sold Jan 30, 2026

    700 Melrose Ave Unit J23, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 772 Sq Ft
    • Built 1964

    Last Sold Summary

    • 6% Below List Price
    • $285/SF
    • 107 Days On Market

    Current Estimated Value $216,749

    Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    700 Melrose Ave Unit J23, Winter Park, FL 32789
  • /2

    $1,900,000

    Sold Jun 03, 2026

    1760 Alabama Dr, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,841 Sq Ft
    • Built 1971

    Last Sold Summary

    • 24% Below List Price
    • $669/SF
    • 75 Days On Market

    Current Estimated Value $1,884,993

    Last Listing Agent Brian Ruth DAILLAND REAL ESTATE

    1760 Alabama Dr, Winter Park, FL 32789
  • /2

    $400,000

    Sold Feb 13, 2026

    2833 Prince John Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,605 Sq Ft
    • Built 1963

    Last Sold Summary

    • 7% Below List Price
    • $249/SF
    • 9 Days On Market

    Current Estimated Value $407,976

    Last Listing Agent Makena Clark EXIT REALTY PREMIER LEGACY

    2833 Prince John Rd, Winter Park, FL 32792
  • /2

    $735,000

    Sold May 19, 2026

    675 Overspin Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,062 Sq Ft
    • Built 2010

    Last Sold Summary

    • 8% Below List Price
    • $240/SF
    • 58 Days On Market

    Current Estimated Value $757,455

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    675 Overspin Dr, Winter Park, FL 32789
  • /2

    $290,000

    Sold Sep 22, 2025

    7102 Easter St, Winter Park, FL 32792

    • 3 Beds
    • 1 Bath
    • 1,114 Sq Ft
    • Built 1956

    Last Sold Summary

    • 3% Below List Price
    • $260/SF
    • 67 Days On Market

    Current Estimated Value $301,089

    Last Listing Agent Mayken Giraldo THE C SMITH REAL ESTATE GROUP LLC

    7102 Easter St, Winter Park, FL 32792

Showing Results 81 - 120, Page 3 of 18

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