1,102

Recently Sold Winter Park, FL Homes

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  • /2

    $2,100,000

    Sold Jun 11, 2026

    2503 Versailles Ave, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 4,026 Sq Ft
    • Built 2015

    Last Sold Summary

    • 24% Below List Price
    • $522/SF
    • 138 Days On Market

    Current Estimated Value $2,041,682

    Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

    2503 Versailles Ave, Winter Park, FL 32789
  • /2

    $380,000

    Sold Jul 28, 2026

    3949 Cool Water Ct, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,979 Sq Ft
    • Built 1994

    Last Sold Summary

    • 5% Below List Price
    • $192/SF
    • 20 Days On Market

    Current Estimated Value $406,335

    Last Listing Agent Heather Unger, PA ACME REAL ESTATE FLORIDA LLC

    3949 Cool Water Ct, Winter Park, FL 32792
  • /2

    $152,000

    Sold Jul 31, 2026

    3282 Oak Lake Place, Winter Park, FL 32792

    • 2 Beds
    • 1.5 Baths
    • 990 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Below List Price
    • $154/SF
    • 78 Days On Market

    Current Estimated Value $156,643

    Last Listing Agent Chad Busby BUSBY REALTY LLC

    3282 Oak Lake Place, Winter Park, FL 32792
  • /2

    $214,990

    Sold Mar 09, 2026

    7744 Country Place Unit C4, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • Built 1985

    Last Sold Summary

    • $201/SF
    • 7 Days On Market

    Current Estimated Value $217,036

    Last Listing Agent David Knight EXP REALTY LLC

    7744 Country Place Unit C4, Winter Park, FL 32792
  • /2

    $1,100,000

    Sold Mar 16, 2026

    1700 Mizell Ave, Winter Park, FL 32789

    • 4 Beds
    • 4 Baths
    • 2,045 Sq Ft
    • Built 1949

    Last Sold Summary

    • $538/SF
    • 1 Day On Market

    Current Estimated Value $1,084,845

    Last Listing Agent Giannviana Roberts KORR REALTY CORP

    1700 Mizell Ave, Winter Park, FL 32789
  • /2

    $1,475,000

    Sold Mar 16, 2026

    1408 Chapman Cir, Winter Park, FL 32789

    • 4 Beds
    • 4 Baths
    • 3,237 Sq Ft
    • Built 2003

    Last Sold Summary

    • 5% Below List Price
    • $456/SF
    • 95 Days On Market

    Current Estimated Value $1,507,233

    Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

    1408 Chapman Cir, Winter Park, FL 32789
  • /2

    $1,800,000

    Sold Oct 24, 2025

    1682 Arbor Park Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,950 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $610/SF
    • 16 Days On Market

    Current Estimated Value $1,810,296

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    1682 Arbor Park Dr, Winter Park, FL 32789
  • /2

    $550,000

    Sold Nov 10, 2025

    2612 Lafayette Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,447 Sq Ft
    • Built 1956

    Last Sold Summary

    • 39% Below List Price
    • $225/SF
    • 573 Days On Market

    Current Estimated Value $661,685

    Last Listing Agent Maoline Herrera EXP REALTY LLC

    2612 Lafayette Ave, Winter Park, FL 32789
  • /2

    $935,000

    Sold Mar 07, 2026

    2260 Hawick Ln, Winter Park, FL 32792

    • Land
    • 19,602 Sq Ft
    • $2,077,778 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 123 Days On Market

    Current Estimated Value $921,917

    Last Listing Agent Michael Rasmussen DAVEN REAL ESTATE INC

    2260 Hawick Ln, Winter Park, FL 32792
  • /2

    $125,000

    Sold Feb 23, 2026

    1695 Lee Rd Unit B216, Winter Park, FL 32789

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

    Last Sold Summary

    • 7% Below List Price
    • $109/SF
    • 7 Days On Market

    Current Estimated Value $128,123

    Last Listing Agent Martha Grasty EXP REALTY LLC

    1695 Lee Rd Unit B216, Winter Park, FL 32789
  • /2

    $485,000

    Sold Jul 16, 2026

    1032 Manchester Cir, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,787 Sq Ft
    • Built 1976

    Last Sold Summary

    • 3% Above List Price
    • $271/SF
    • 39 Days On Market

    Current Estimated Value $463,109

    Last Listing Agent Nancy Morales BHHS FLORIDA REALTY

    1032 Manchester Cir, Winter Park, FL 32792
  • /2

    $2,500,000

    Sold Mar 31, 2026

    1401 Green Cove Rd, Winter Park, FL 32789

    • 3 Beds
    • 7 Baths
    • 5,483 Sq Ft
    • Built 2009

    Last Sold Summary

    • 14% Below List Price
    • $456/SF
    • 99 Days On Market

    Current Estimated Value $2,644,775

    Last Listing Agent Adriana Oyarce ANCHOR REAL ESTATE

    1401 Green Cove Rd, Winter Park, FL 32789
  • /2

    $1,063,303

    Sold Dec 10, 2025

    1835 Karolina Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,662 Sq Ft
    • Built 2025

    Last Sold Summary

    • 23% Above List Price
    • $399/SF
    • 50 Days On Market

    Current Estimated Value $1,042,333

    Last Listing Agent Laura Hope COMPASS FLORIDA LLC

    1835 Karolina Ave, Winter Park, FL 32789
  • /2

    $699,450

    Sold Nov 19, 2025

    1346 Golfside Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,829 Sq Ft
    • Built 1979

    Last Sold Summary

    • 1% Above List Price
    • $382/SF
    • 4 Days On Market

    Current Estimated Value $709,543

    Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

    1346 Golfside Dr, Winter Park, FL 32792
  • /2

    $387,000

    Sold Dec 23, 2025

    5422 Albert Dr, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,689 Sq Ft
    • Built 1978

    Last Sold Summary

    • 9% Below List Price
    • $229/SF
    • 74 Days On Market

    Current Estimated Value $389,604

    Last Listing Agent Virginia Bellhorn WATSON REALTY CORP

    5422 Albert Dr, Winter Park, FL 32792
  • /2

    $275,000

    Sold Mar 31, 2026

    409 Sandlewood Cove Unit 3, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 1,413 Sq Ft
    • Built 1986

    Last Sold Summary

    • $195/SF

    Current Estimated Value $269,182

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    409 Sandlewood Cove Unit 3, Winter Park, FL 32789
  • /2

    $2,025,000

    Sold Aug 06, 2026

    2299 Via Tuscany, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,986 Sq Ft
    • Built 1953

    Last Sold Summary

    • 14% Below List Price
    • $508/SF
    • 230 Days On Market

    Current Estimated Value $2,225,992

    Last Listing Agent Vincent Scarlatos CORCORAN PREMIER REALTY

    2299 Via Tuscany, Winter Park, FL 32789
  • /2

    $312,000

    Sold Oct 16, 2025

    1921 Dartmouth Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 987 Sq Ft
    • Built 1956

    Last Sold Summary

    • 16% Below List Price
    • $316/SF
    • 76 Days On Market

    Current Estimated Value $330,231

    Last Listing Agent Pat Hancock THOMAS LYNNE REALTY GROUP LLC

    1921 Dartmouth Ave, Winter Park, FL 32789
  • /2

    $78,000

    Sold Nov 25, 2025

    330 Scottsdale Square Unit 330, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft
    • Built 1974

    Last Sold Summary

    • 12% Below List Price
    • $76/SF
    • 25 Days On Market

    Current Estimated Value $86,664

    Last Listing Agent Milton James COLDWELL BANKER REALTY

    330 Scottsdale Square Unit 330, Winter Park, FL 32792
  • /2

    $310,000

    Sold Aug 29, 2025

    7642 Glenmoor Ln, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,217 Sq Ft
    • Built 1984

    Last Sold Summary

    • 24% Above List Price
    • $255/SF
    • 4 Days On Market

    Current Estimated Value $330,992

    Last Listing Agent Pam Grabenhorst THE WILKINS WAY LLC

    7642 Glenmoor Ln, Winter Park, FL 32792
  • /2

    $3,000,000

    Sold Aug 18, 2025

    1730 Winchester Dr, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,080 Sq Ft
    • Built 2024

    Last Sold Summary

    • 9% Below List Price
    • $735/SF
    • 313 Days On Market

    Current Estimated Value $3,116,873

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    1730 Winchester Dr, Winter Park, FL 32789
  • /2

    $449,000

    Sold Dec 10, 2025

    1710 Aster Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft
    • Built 1979

    Last Sold Summary

    • 11% Below List Price
    • $270/SF
    • 302 Days On Market

    Current Estimated Value $451,524

    Last Listing Agent Dora Siler FOLIO REALTY LLC

    1710 Aster Dr, Winter Park, FL 32792
  • /2

    $130,000

    Sold May 01, 2026

    151 Lewfield Cir Unit 4, Winter Park, FL 32792

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

    Last Sold Summary

    • 16% Below List Price
    • $192/SF
    • 115 Days On Market

    Current Estimated Value $132,238

    Last Listing Agent Susan Tamlin KELLER WILLIAMS REALTY AT THE PARKS

    151 Lewfield Cir Unit 4, Winter Park, FL 32792
  • /2

    $2,200,000

    Sold Sep 09, 2025

    1554 Lake Knowles Cir, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 3,155 Sq Ft
    • Built 1954

    Last Sold Summary

    • 12% Below List Price
    • $697/SF
    • 2 Days On Market

    Current Estimated Value $2,208,540

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

    1554 Lake Knowles Cir, Winter Park, FL 32789
  • /2

    $150,000

    Sold Aug 15, 2025

    3318 Amber Wood Way Unit 100, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft
    • Built 1983

    Last Sold Summary

    • 7,795% Above List Price
    • $145/SF
    • 0 Days On Market

    Current Estimated Value $162,760

    Last Listing Agent Ramon Ortiz Cruz DIAMOND 2000 REALTY, INC

    3318 Amber Wood Way Unit 100, Winter Park, FL 32792
  • /2

    $755,000

    Sold Feb 26, 2026

    1317 Medinah Ct, Winter Park, FL 32792

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

    Last Sold Summary

    • 3% Below List Price
    • $375/SF
    • 13 Days On Market

    Current Estimated Value $734,934

    Last Listing Agent Zach Mitchell SAND DOLLAR REALTY GROUP INC

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

    $434,000

    Sold Aug 04, 2026

    5117 Cypress Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,534 Sq Ft
    • Built 1972

    Last Sold Summary

    • 4% Below List Price
    • $283/SF
    • 36 Days On Market

    Current Estimated Value $439,203

    Last Listing Agent Kristin McIntosh EXP REALTY LLC

    5117 Cypress Ct, Winter Park, FL 32792
  • /2

    $3,100,001

    Sold Apr 13, 2026

    611 Williams Dr, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 4,686 Sq Ft
    • Built 2007

    Last Sold Summary

    • 4% Above List Price
    • $662/SF
    • 6 Days On Market

    Current Estimated Value $3,018,102

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    611 Williams Dr, Winter Park, FL 32789
  • /2

    $272,250

    Sold Apr 29, 2026

    2519 Windward Way, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Built 1976

    Last Sold Summary

    • 7% Below List Price
    • $246/SF
    • 13 Days On Market

    Current Estimated Value $269,437

    Last Listing Agent Itzel Sotorosa NONA LEGACY POWERED BY LA ROSA

    2519 Windward Way, Winter Park, FL 32792
  • /2

    $350,000

    Sold Dec 30, 2025

    3117 Shady Pine Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,214 Sq Ft
    • Built 1983

    Last Sold Summary

    • 10% Below List Price
    • $288/SF
    • 88 Days On Market

    Current Estimated Value $360,856

    Last Listing Agent Alistair Baxter EXP REALTY LLC

    3117 Shady Pine Ave, Winter Park, FL 32792
  • /2

    $1,840,000

    Sold Jun 09, 2026

    640 Arjay Way, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 3,953 Sq Ft
    • Built 1958

    Last Sold Summary

    • 8% Below List Price
    • $465/SF
    • 107 Days On Market

    Current Estimated Value $1,806,419

    Last Listing Agent Farah Bloom KELLER WILLIAMS WINTER PARK

    640 Arjay Way, Winter Park, FL 32789
  • /2

    $1,050,000

    Sold Aug 14, 2025

    2250 Forrest Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,492 Sq Ft
    • Built 1950

    Last Sold Summary

    • 12% Below List Price
    • $704/SF
    • 0 Days On Market

    Current Estimated Value $1,039,004

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

    2250 Forrest Rd, Winter Park, FL 32789
  • /2

    $200,000

    Sold Jan 30, 2026

    1821 Killarney Dr, Winter Park, FL 32789

    • Land
    • 16,552 Sq Ft
    • $526,316 per Acre

    Last Sold Summary

    Current Estimated Value $894,485

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    1821 Killarney Dr, Winter Park, FL 32789
  • /2

    $389,000

    Sold Apr 02, 2026

    311 E Morse Blvd Unit 7-2, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • Built 1960

    Last Sold Summary

    • 25% Below List Price
    • $432/SF
    • 567 Days On Market

    Current Estimated Value $380,669

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    311 E Morse Blvd Unit 7-2, Winter Park, FL 32789
  • /2

    $482,000

    Sold May 28, 2026

    958 Hanover Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 1,378 Sq Ft
    • Built 1956

    Last Sold Summary

    • 2% Below List Price
    • $350/SF
    • 9 Days On Market

    Current Estimated Value $477,239

    Last Listing Agent Christopher Lyons AGILE GROUP REALTY

    958 Hanover Ave, Winter Park, FL 32789
  • /2

    $3,000,000

    Sold Jul 22, 2026

    1351 Magnolia Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,460 Sq Ft
    • Built 2026

    Last Sold Summary

    • 3% Below List Price
    • $867/SF
    • 0 Days On Market

    Current Estimated Value $2,374,328

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    1351 Magnolia Ave, Winter Park, FL 32789
  • /2

    $1,300,000

    Sold May 29, 2026

    1780 Mondrian Cir, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft
    • Built 2023

    Last Sold Summary

    • 7% Below List Price
    • $563/SF
    • 48 Days On Market

    Current Estimated Value $1,278,157

    Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

    1780 Mondrian Cir, Winter Park, FL 32789
  • /2

    $560,000

    Sold Apr 10, 2026

    1517 Harmon Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,035 Sq Ft
    • Built 2005

    Last Sold Summary

    • $275/SF

    Current Estimated Value $630,091

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    1517 Harmon Ave, Winter Park, FL 32789
  • /2

    $1,670,000

    Sold Mar 04, 2026

    501 Darcey Dr, Winter Park, FL 32792

    • 5 Beds
    • 4.5 Baths
    • 3,033 Sq Ft
    • Built 2023

    Last Sold Summary

    • $551/SF
    • 3 Days On Market

    Current Estimated Value $1,659,396

    Last Listing Agent Karen Jacobs COLDWELL BANKER REALTY

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

    $975,000

    Sold Nov 18, 2025

    901 Palmer Ave, Winter Park, FL 32789

    • Land
    • 13,939 Sq Ft
    • $3,046,875 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 33 Days On Market

    Current Estimated Value $1,065,607

    Last Listing Agent Sharon Helsby FANNIE HILLMAN & ASSOCIATES

    901 Palmer Ave, Winter Park, FL 32789

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