1,128

Recently Sold Winter Park, FL Homes

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  • /2

    $1,650,000

    Sold Jun 30, 2025

    2339 Lafayette Ave, Winter Park, FL 32789

    • 4 Beds
    • 6 Baths
    • 3,379 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $488/SF
    • 15 Days On Market

    Current Estimated Value $1,694,236

    Last Listing Agent Skip Kirst COLLADO REAL ESTATE

    2339 Lafayette Ave, Winter Park, FL 32789
  • /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 $2,995,439

    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 $272,676

    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 $353,208

    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 $1,830,954

    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 $1,023,691

    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 $199,316

    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 $382,718

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

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

    $965,000

    Sold Jul 07, 2025

    1760 Mondrian Cir, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,245 Sq Ft
    • Built 2024

    Last Sold Summary

    • 1% Below List Price
    • $430/SF
    • 11 Days On Market

    Current Estimated Value $945,805

    Last Listing Agent Brian Teach COLDWELL BANKER REALTY

    1760 Mondrian Cir, 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 $479,538

    Last Listing Agent Christopher Lyons AGILE GROUP REALTY

    958 Hanover 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 $1,365,808

    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 $603,718

    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 $1,648,959

    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 $994,019

    Last Listing Agent Sharon Helsby FANNIE HILLMAN & ASSOCIATES

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

    $365,000

    Sold Nov 05, 2025

    2320 High St, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,071 Sq Ft
    • Built 1971

    Last Sold Summary

    • 9% Below List Price
    • $341/SF
    • 63 Days On Market

    Current Estimated Value $356,386

    Last Listing Agent Jessica Lee ONE LUXURY INTERNATIONAL LLC

    2320 High St, Winter Park, FL 32792
  • /2

    $1,650,000

    Sold Oct 09, 2025

    1915 Stonehurst Rd, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,489 Sq Ft
    • Built 1956

    Last Sold Summary

    • $663/SF
    • 0 Days On Market

    Current Estimated Value $1,646,019

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    1915 Stonehurst Rd, Winter Park, FL 32789
  • /2

    $362,500

    Sold Jul 30, 2025

    311 E Morse Blvd Unit 6-7, Winter Park, FL 32789

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

    Last Sold Summary

    • 19% Below List Price
    • $410/SF
    • 103 Days On Market

    Current Estimated Value $381,804

    Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    311 E Morse Blvd Unit 6-7, Winter Park, FL 32789
  • /2

    $1,810,000

    Sold Mar 31, 2026

    1710 Oneco Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,240 Sq Ft
    • Built 2020

    Last Sold Summary

    • $559/SF

    Current Estimated Value $1,804,328

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

    1710 Oneco Ave, Winter Park, FL 32789
  • /2

    $550,000

    Sold Oct 23, 2025

    7864 Pleasant Pine Cir, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,182 Sq Ft
    • Built 2016

    Last Sold Summary

    • 2% Above List Price
    • $252/SF
    • 6 Days On Market

    Current Estimated Value $559,438

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    7864 Pleasant Pine Cir, Winter Park, FL 32792
  • /2

    $513,000

    Sold Aug 22, 2025

    1819 Shadyhill Terrace, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,811 Sq Ft
    • Built 1989

    Last Sold Summary

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

    Current Estimated Value $507,763

    Last Listing Agent Jonathan Ruiz KELLER WILLIAMS WINTER PARK

    1819 Shadyhill Terrace, Winter Park, FL 32792
  • /2

    $420,000

    Sold Jul 17, 2025

    5334 Cypress Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,734 Sq Ft
    • Built 1976

    Last Sold Summary

    • 1% Above List Price
    • $242/SF
    • 4 Days On Market

    Current Estimated Value $426,676

    Last Listing Agent Jeff Taulbee CHARLES RUTENBERG REALTY ORLANDO

    5334 Cypress Dr, Winter Park, FL 32792
  • /2

    $600,000

    Sold Oct 17, 2025

    2812 Woodside Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,842 Sq Ft
    • Built 1952

    Last Sold Summary

    • 4% Below List Price
    • $326/SF
    • 50 Days On Market

    Current Estimated Value $601,782

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    2812 Woodside Ave, Winter Park, FL 32789
  • /2

    $439,900

    Sold Feb 12, 2026

    2835 Bongart Rd, Winter Park, FL 32792

    • 3 Beds
    • 3 Baths
    • 1,880 Sq Ft
    • Built 1961

    Last Sold Summary

    • $234/SF
    • 4 Days On Market

    Current Estimated Value $433,822

    Last Listing Agent Irina Paul FUTURE HOME REALTY INC

    2835 Bongart Rd, Winter Park, FL 32792
  • /59

    $300,000

    Sold Dec 23, 2025

    1405 Auburn Green Loop, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,126 Sq Ft
    • Built 1984

    Last Sold Summary

    • 17% Below List Price
    • $266/SF
    • 170 Days On Market

    Current Estimated Value $308,144

    Last Listing Agent Geannina Mejia-Acevedo Charles Rutenberg Realty Orlan

    1405 Auburn Green Loop, Winter Park, FL 32792
  • /2

    $615,000

    Sold Jun 10, 2026

    1034 Turner Rd, Winter Park, FL 32789

    • Land
    • 23,522 Sq Ft
    • $1,138,889 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 77 Days On Market

    Current Estimated Value $705,511

    Last Listing Agent Parker Blanchard OLDE TOWN BROKERS INC

    1034 Turner Rd, Winter Park, FL 32789
  • /2

    $660,000

    Sold Jun 05, 2026

    5275 Pine Lily Cir, Winter Park, FL 32792

    • 5 Beds
    • 3.5 Baths
    • 3,152 Sq Ft
    • Built 2014

    Last Sold Summary

    • 4% Below List Price
    • $209/SF
    • 87 Days On Market

    Current Estimated Value $666,258

    Last Listing Agent Kathy Williams REAL BROKER, LLC

    5275 Pine Lily Cir, Winter Park, FL 32792
  • /2

    $1,025,000

    Sold Jun 27, 2025

    2680 Oglesby Ave, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,546 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Below List Price
    • $403/SF
    • 55 Days On Market

    Current Estimated Value $1,020,281

    Last Listing Agent Kris Kennedy COMPASS FLORIDA LLC

    2680 Oglesby Ave, Winter Park, FL 32789
  • /18

    $1,000,000

    Sold May 15, 2026

    1903 S Lakemont Ave, Winter Park, FL 32792

    • 4,056 Sq Ft
    • Built 1964

    Last Sold Summary

    • 60% Below List Price
    • $247/SF
    • 386 Days On Market

    Last Listing Agent Maria Tenner Platinum Properties Int'l Inc.

    1903 S Lakemont Ave, Winter Park, FL 32792
  • /2

    $390,000

    Sold Oct 27, 2025

    5346 Cypress Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • Built 1976

    Last Sold Summary

    • 7% Below List Price
    • $234/SF
    • 31 Days On Market

    Current Estimated Value $391,624

    Last Listing Agent Kristy Kesterson KELLER WILLIAMS ADVANTAGE REALTY

    5346 Cypress Dr, Winter Park, FL 32792
  • /2

    $405,000

    Sold Apr 01, 2026

    1028 Lake Bell Dr, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,418 Sq Ft
    • Built 1956

    Last Sold Summary

    • 1% Above List Price
    • $286/SF
    • 4 Days On Market

    Current Estimated Value $398,824

    Last Listing Agent Maria Nunez COMPASS FLORIDA LLC

    1028 Lake Bell Dr, Winter Park, FL 32789
  • /2

    $170,000

    Sold Sep 04, 2025

    3651 N Goldenrod Rd Unit 210, Winter Park, FL 32792

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

    Last Sold Summary

    • 15% Below List Price
    • $202/SF
    • 176 Days On Market

    Last Listing Agent Elenice Pereira WRA BUSINESS & REAL ESTATE

    3651 N Goldenrod Rd Unit 210, Winter Park, FL 32792
  • /2

    $1,050,000

    Sold Jul 14, 2025

    795 W Canton Ave, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,374 Sq Ft
    • Built 2017

    Last Sold Summary

    • 9% Below List Price
    • $442/SF
    • 23 Days On Market

    Current Estimated Value $1,067,665

    Last Listing Agent Margo Rochelle WEICHERT REALTORS HALLMARK PROPERTIES

    795 W Canton Ave, Winter Park, FL 32789
  • /2

    $360,000

    Sold Aug 08, 2025

    1612 Eastbrook Blvd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,240 Sq Ft
    • Built 1961

    Last Sold Summary

    • 3% Below List Price
    • $290/SF
    • 104 Days On Market

    Current Estimated Value $358,757

    Last Listing Agent Justin Adams EXP REALTY LLC

    1612 Eastbrook Blvd, Winter Park, FL 32792
  • /2

    $507,500

    Sold Jun 17, 2026

    2009 Shadyhill Terrace, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • Built 1987

    Last Sold Summary

    • 5% Below List Price
    • $304/SF
    • 19 Days On Market

    Current Estimated Value $522,151

    Last Listing Agent Byron Kirkpatrick HOUSE HUNTING IN FLORIDA LLC

    2009 Shadyhill Terrace, Winter Park, FL 32792
  • /2

    $1,480,000

    Sold Sep 19, 2025

    1742 Barcelona Way, Winter Park, FL 32789

    • 5 Beds
    • 8 Baths
    • 3,626 Sq Ft
    • Built 1973

    Last Sold Summary

    • 18% Below List Price
    • $408/SF
    • 81 Days On Market

    Current Estimated Value $1,562,306

    Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

    1742 Barcelona Way, Winter Park, FL 32789
  • /2

    $365,000

    Sold May 13, 2026

    765 Baffie Ave, Winter Park, FL 32789

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

    Last Sold Summary

    • 4% Below List Price
    • $390/SF
    • 32 Days On Market

    Current Estimated Value $371,503

    Last Listing Agent Anne Rogers ANNE ROGERS REALTY GROUP INC

    765 Baffie Ave, Winter Park, FL 32789
  • /2

    $350,000

    Sold Jul 21, 2025

    1541 Florentino Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,682 Sq Ft
    • Built 2004

    Last Sold Summary

    • $208/SF
    • 70 Days On Market

    Current Estimated Value $356,685

    Last Listing Agent Jeffrey Friedman FANNIE HILLMAN & ASSOCIATES

    1541 Florentino Ln, Winter Park, FL 32792
  • /2

    $560,000

    Sold Aug 19, 2025

    1339 Orchid Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 789 Sq Ft
    • Built 1953

    Last Sold Summary

    • 12% Below List Price
    • $710/SF
    • 46 Days On Market

    Current Estimated Value $548,845

    Last Listing Agent Barbara Allen ABIDE REALTY

    1339 Orchid Ave, Winter Park, FL 32789
  • /2

    $975,000

    Sold Mar 25, 2026

    456 Carolina Ave, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 1,615 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Below List Price
    • $604/SF
    • 9 Days On Market

    Current Estimated Value $972,808

    Last Listing Agent Heather Frazee FANNIE HILLMAN & ASSOCIATES

    456 Carolina Ave, Winter Park, FL 32789
  • /2

    $140,000

    Sold Nov 17, 2025

    4960 Tangerine Ave Unit 4960, Winter Park, FL 32792

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

    Last Sold Summary

    • 10% Below List Price
    • $183/SF
    • 72 Days On Market

    Current Estimated Value $143,880

    Last Listing Agent Stacy Chen KELLER WILLIAMS ADVANTAGE III

    4960 Tangerine Ave Unit 4960, Winter Park, FL 32792

Showing Results 321 - 360, Page 9 of 18

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