1,174

Recently Sold Winter Park, FL Homes

Section Image
  • 700 Melrose Ave Unit F2, Winter Park, FL 32789
    700 Melrose Ave Unit F2, Winter Park, FL 32789
    /2

    $230,000 Sold Feb 21, 2025

    700 Melrose Ave Unit F2, Winter Park, FL 32789

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

    Last Sold Summary

    • 8% Below List Price
    • $315/SF
    • 193 Days On Market

    Current Estimated Value $218,087

    Last Listing Agent Carol van den Berg FLORIDA ONE REAL ESTATE LLC

    700 Melrose Ave Unit F2, Winter Park, FL 32789
  • 2500 Lee Rd Unit 243, Winter Park, FL 32789
    2500 Lee Rd Unit 243, Winter Park, FL 32789
    /2

    $195,000 Sold Jan 31, 2025

    2500 Lee Rd Unit 243, Winter Park, FL 32789

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

    Last Sold Summary

    • 2% Below List Price
    • $302/SF
    • 10 Days On Market

    Last Listing Agent Christine Bouchard HOMESMART

    2500 Lee Rd Unit 243, Winter Park, FL 32789
  • 3304 Bennington Ct, Winter Park, FL 32792
    3304 Bennington Ct, Winter Park, FL 32792
    /2

    $455,000 Sold Aug 20, 2025

    3304 Bennington Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,804 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $252/SF
    • 59 Days On Market

    Current Estimated Value $453,181

    Last Listing Agent Peter Hamilton DAHLIA REALTY GROUP

    3304 Bennington Ct, Winter Park, FL 32792
  • 2161 Sharon Rd, Winter Park, FL 32789
    2161 Sharon Rd, Winter Park, FL 32789
    /2

    $4,430,000 Sold Oct 09, 2025

    2161 Sharon Rd, Winter Park, FL 32789

    • 5 Beds
    • 6.5 Baths
    • 6,338 Sq Ft
    • Built 2023

    Last Sold Summary

    • 11% Below List Price
    • $699/SF
    • 247 Days On Market

    Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

    2161 Sharon Rd, Winter Park, FL 32789
  • 2518 Sweetwater Trail, Winter Park, FL 32789
    2518 Sweetwater Trail, Winter Park, FL 32789
    /2

    $519,180 Sold Jul 08, 2025

    2518 Sweetwater Trail, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 2,205 Sq Ft
    • Built 1965

    Last Sold Summary

    • 21% Below List Price
    • $235/SF
    • 201 Days On Market

    Current Estimated Value $578,683

    Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

    2518 Sweetwater Trail, Winter Park, FL 32789
  • 1450 Glencoe Rd, Winter Park, FL 32789
    1450 Glencoe Rd, Winter Park, FL 32789
    /2

    $1,565,000 Sold Sep 24, 2025

    1450 Glencoe Rd, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,662 Sq Ft
    • Built 1952

    Last Sold Summary

    • 1% Below List Price
    • $588/SF
    • 42 Days On Market

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1450 Glencoe Rd, Winter Park, FL 32789
  • 631 Callahan St, Winter Park, FL 32789
    631 Callahan St, Winter Park, FL 32789
    /2

    $600,000 Sold Apr 04, 2025

    631 Callahan St, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,751 Sq Ft
    • Built 1950

    Last Sold Summary

    • 8% Below List Price
    • $343/SF
    • 41 Days On Market

    Current Estimated Value $596,222

    Last Listing Agent Yousef Zeidan CORCORAN PREMIER REALTY

    631 Callahan St, Winter Park, FL 32789
  • 620 Pinetree Rd, Winter Park, FL 32789
    620 Pinetree Rd, Winter Park, FL 32789
    /2

    $2,300,000 Sold Jan 15, 2025

    620 Pinetree Rd, Winter Park, FL 32789

    • Land
    • 0.49 Acre
    • $4,693,878 per Acre

    Last Sold Summary

    • 0 Days On Market

    Current Estimated Value $2,270,952

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    620 Pinetree Rd, Winter Park, FL 32789
  • 2480 Tahoe Cir, Winter Park, FL 32792
    2480 Tahoe Cir, Winter Park, FL 32792
    /2

    $240,000 Sold Sep 10, 2025

    2480 Tahoe Cir, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,173 Sq Ft
    • Built 1980

    Last Sold Summary

    • 9% Below List Price
    • $205/SF
    • 41 Days On Market

    Current Estimated Value $236,939

    Last Listing Agent Michael Wood UNITED REAL ESTATE PREFERRED

    2480 Tahoe Cir, Winter Park, FL 32792
  • 678 Depugh St, Winter Park, FL 32789
    678 Depugh St, Winter Park, FL 32789
    /2

    $675,000 Sold Jan 29, 2025

    678 Depugh St, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 1,940 Sq Ft
    • Built 1952

    Last Sold Summary

    • 4% Below List Price
    • $348/SF
    • 89 Days On Market

    Current Estimated Value $694,780

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    678 Depugh St, Winter Park, FL 32789
  • 1387 Sawgrass Ct, Winter Park, FL 32792
    1387 Sawgrass Ct, Winter Park, FL 32792
    /2

    $550,000 Sold Jul 17, 2025

    1387 Sawgrass Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,867 Sq Ft
    • Built 1979

    Last Sold Summary

    • 4% Below List Price
    • $295/SF
    • 8 Days On Market

    Current Estimated Value $548,077

    Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    1387 Sawgrass Ct, Winter Park, FL 32792
  • 600 Ololu Dr, Winter Park, FL 32789
    600 Ololu Dr, Winter Park, FL 32789
    /2

    $2,250,000 Sold Nov 17, 2025

    600 Ololu Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,749 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Below List Price
    • $600/SF
    • 2 Days On Market

    Last Listing Agent David Francetic COLDWELL BANKER RESIDENTIAL RE

    600 Ololu Dr, Winter Park, FL 32789
  • 796 Mcintyre Ave, Winter Park, FL 32789
    796 Mcintyre Ave, Winter Park, FL 32789
    /2

    $645,000 Sold Jun 13, 2025

    796 Mcintyre Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,910 Sq Ft
    • Built 1988

    Last Sold Summary

    • 4% Below List Price
    • $338/SF
    • 18 Days On Market

    Current Estimated Value $647,514

    Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    796 Mcintyre Ave, Winter Park, FL 32789
  • 700 Melrose Ave Unit B4, Winter Park, FL 32789
    700 Melrose Ave Unit B4, Winter Park, FL 32789
    /2

    $260,000 Sold Feb 28, 2025

    700 Melrose Ave Unit B4, Winter Park, FL 32789

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

    Last Sold Summary

    • $242/SF
    • 0 Days On Market

    Current Estimated Value $291,515

    Last Listing Agent Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

    700 Melrose Ave Unit B4, Winter Park, FL 32789
  • 232 Lewfield Cir, Winter Park, FL 32792
    232 Lewfield Cir, Winter Park, FL 32792
    /2

    $200,000 Sold Feb 21, 2025

    232 Lewfield Cir, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 953 Sq Ft
    • Built 1973

    Last Sold Summary

    • 1% Above List Price
    • $210/SF
    • 39 Days On Market

    Current Estimated Value $194,434

    Last Listing Agent Kym LaQuea CHARLES RUTENBERG REALTY ORLANDO

    232 Lewfield Cir, Winter Park, FL 32792
  • 958 Dunraven Dr, Winter Park, FL 32792
    958 Dunraven Dr, Winter Park, FL 32792
    /2

    $649,000 Sold Jul 02, 2025

    958 Dunraven Dr, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,835 Sq Ft
    • Built 1957

    Last Sold Summary

    • 9% Below List Price
    • $354/SF
    • 126 Days On Market

    Current Estimated Value $632,952

    Last Listing Agent Rhonda Hunter COLDWELL BANKER RESIDENTIAL RE

    958 Dunraven Dr, Winter Park, FL 32792
  • 1368 Devon Rd, Winter Park, FL 32789
    1368 Devon Rd, Winter Park, FL 32789
    /2

    $569,000 Sold May 30, 2025

    1368 Devon Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,642 Sq Ft
    • Built 1952

    Last Sold Summary

    • $347/SF
    • 5 Days On Market

    Current Estimated Value $573,522

    Last Listing Agent Karen Ripperger LPT REALTY, LLC

    1368 Devon Rd, Winter Park, FL 32789
  • 200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792
    /2

    $198,500 Sold Jan 30, 2025

    200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792

    • 2 Beds
    • 1.5 Baths
    • 1,219 Sq Ft
    • Built 1970

    Last Sold Summary

    • 21% Below List Price
    • $163/SF
    • 80 Days On Market

    Current Estimated Value $205,010

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792
  • 266 Chase Ave, Winter Park, FL 32789
    266 Chase Ave, Winter Park, FL 32789
    /2

    $2,935,000 Sold May 27, 2025

    266 Chase Ave, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,088 Sq Ft
    • Built 1930

    Last Sold Summary

    • 10% Below List Price
    • $718/SF
    • 30 Days On Market

    Current Estimated Value $2,894,095

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

    266 Chase Ave, Winter Park, FL 32789
  • 2368 Summerfield Rd, Winter Park, FL 32792
    2368 Summerfield Rd, Winter Park, FL 32792
    /2

    $717,000 Sold Apr 30, 2025

    2368 Summerfield Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft
    • Built 1966

    Last Sold Summary

    • 3% Above List Price
    • $377/SF
    • 6 Days On Market

    Current Estimated Value $707,188

    Last Listing Agent Erin Tompkins COLDWELL BANKER RESIDENTIAL RE

    2368 Summerfield Rd, Winter Park, FL 32792
  • 104 Cortland Ave, Winter Park, FL 32789
    104 Cortland Ave, Winter Park, FL 32789
    /2

    $2,100,000 Sold Jul 07, 2025

    104 Cortland Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 3,182 Sq Ft
    • Built 1926

    Last Sold Summary

    • 12% Below List Price
    • $660/SF
    • 36 Days On Market

    Current Estimated Value $2,108,017

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

    104 Cortland Ave, Winter Park, FL 32789
  • 1409 Hyde Park Dr, Winter Park, FL 32792
    1409 Hyde Park Dr, Winter Park, FL 32792
    /2

    $455,000 Sold Mar 21, 2025

    1409 Hyde Park Dr, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,018 Sq Ft
    • Built 1986

    Last Sold Summary

    • 8% Below List Price
    • $225/SF
    • 128 Days On Market

    Current Estimated Value $466,039

    Last Listing Agent Leyder Salamanca FLORIDA REALTY INVESTMENTS

    1409 Hyde Park Dr, Winter Park, FL 32792
  • 2310 Cady Way, Winter Park, FL 32792
    2310 Cady Way, Winter Park, FL 32792
    /2

    $550,000 Sold Jun 24, 2025

    2310 Cady Way, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft
    • Built 1961

    Last Sold Summary

    • 8% Below List Price
    • $296/SF
    • 68 Days On Market

    Current Estimated Value $573,367

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    2310 Cady Way, Winter Park, FL 32792
  • 1429 Indiana Ave, Winter Park, FL 32789
    1429 Indiana Ave, Winter Park, FL 32789
    /2

    $749,000 Sold Aug 01, 2025

    1429 Indiana Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,939 Sq Ft
    • Built 2019

    Last Sold Summary

    • 6% Below List Price
    • $386/SF
    • 63 Days On Market

    Current Estimated Value $743,555

    Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

    1429 Indiana Ave, Winter Park, FL 32789
  • 2138 Whitehall Dr, Winter Park, FL 32792
    2138 Whitehall Dr, Winter Park, FL 32792
    /2

    $500,000 Sold Jul 25, 2025

    2138 Whitehall Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,752 Sq Ft
    • Built 1964

    Last Sold Summary

    • 9% Below List Price
    • $285/SF
    • 63 Days On Market

    Current Estimated Value $500,273

    Last Listing Agent Angela McCloskey KELLER WILLIAMS REALTY AT THE PARKS

    2138 Whitehall Dr, Winter Park, FL 32792
  • 3377 Hamlet Loop, Winter Park, FL 32792
    3377 Hamlet Loop, Winter Park, FL 32792
    /2

    $385,000 Sold Apr 15, 2025

    3377 Hamlet Loop, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,397 Sq Ft
    • Built 1994

    Last Sold Summary

    • 4% Below List Price
    • $276/SF
    • 46 Days On Market

    Current Estimated Value $375,937

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    3377 Hamlet Loop, Winter Park, FL 32792
  • 734 Maryland Ave, Winter Park, FL 32789
    734 Maryland Ave, Winter Park, FL 32789
    /2

    $819,000 Sold Oct 31, 2025

    734 Maryland Ave, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 1926

    Last Sold Summary

    • 3% Below List Price
    • $655/SF
    • 44 Days On Market

    Last Listing Agent Michael Domi PREMIER SOTHEBY'S INTL. REALTY

    734 Maryland Ave, Winter Park, FL 32789
  • 640 Worthington Dr, Winter Park, FL 32789
    640 Worthington Dr, Winter Park, FL 32789
    /2

    $755,000 Sold Mar 03, 2025

    640 Worthington Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 2,012 Sq Ft
    • Built 1960

    Last Sold Summary

    • 100% Below List Price
    • $375/SF
    • 78 Days On Market

    Current Estimated Value $764,263

    Last Listing Agent Felicia Donateli PALM PROPERTIES OF CF, INC.

    640 Worthington Dr, Winter Park, FL 32789
  • 438 W Swoope Ave, Winter Park, FL 32789
    438 W Swoope Ave, Winter Park, FL 32789
    /2

    $715,000 Sold Sep 26, 2025

    438 W Swoope Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft
    • Built 2014

    Last Sold Summary

    • 9% Below List Price
    • $275/SF
    • 46 Days On Market

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    438 W Swoope Ave, Winter Park, FL 32789
  • 200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792
    /2

    $170,000 Sold Jul 03, 2025

    200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,067 Sq Ft
    • Built 1970

    Last Sold Summary

    • 10% Below List Price
    • $159/SF
    • 58 Days On Market

    Current Estimated Value $175,304

    Last Listing Agent Patricia Wojewoda BETTER HOMES & GARDENS RE STAR

    200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792
  • 2464 Lotafun Ave, Winter Park, FL 32789
    2464 Lotafun Ave, Winter Park, FL 32789
    /2

    $410,000 Sold Dec 02, 2025

    2464 Lotafun Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 1,804 Sq Ft
    • Built 1951

    Last Sold Summary

    • 9% Below List Price
    • $227/SF
    • 112 Days On Market

    Last Listing Agent Irina Paul FUTURE HOME REALTY INC

    2464 Lotafun Ave, Winter Park, FL 32789
  • 1919 S Lakemont Ave, Winter Park, FL 32792
    1919 S Lakemont Ave, Winter Park, FL 32792
    /2

    $850,000 Sold Jun 20, 2025

    1919 S Lakemont Ave, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 2,085 Sq Ft
    • Built 2024

    Last Sold Summary

    • 10% Below List Price
    • $408/SF
    • 282 Days On Market

    Current Estimated Value $850,886

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    1919 S Lakemont Ave, Winter Park, FL 32792
  • 2178 Whitehall Dr, Winter Park, FL 32792
    2178 Whitehall Dr, Winter Park, FL 32792
    /2

    $738,000 Sold May 09, 2025

    2178 Whitehall Dr, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,360 Sq Ft
    • Built 1964

    Last Sold Summary

    • 3% Below List Price
    • $313/SF
    • 8 Days On Market

    Current Estimated Value $726,273

    Last Listing Agent Erica Diltz BALDWIN PARK REALTY LLC

    2178 Whitehall Dr, Winter Park, FL 32792
  • 197 Scottsdale Square, Winter Park, FL 32792
    197 Scottsdale Square, Winter Park, FL 32792
    /2

    $100,000 Sold Jun 25, 2025

    197 Scottsdale Square, Winter Park, FL 32792

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

    Last Sold Summary

    • 5% Below List Price
    • $98/SF
    • 1 Day On Market

    Current Estimated Value $96,123

    Last Listing Agent Edward Lee LA ROSA REALTY ORLANDO LLC

    197 Scottsdale Square, Winter Park, FL 32792
  • 1908 Carrigan Ave, Winter Park, FL 32792
    1908 Carrigan Ave, Winter Park, FL 32792
    /2

    $290,000 Sold Jun 13, 2025

    1908 Carrigan Ave, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,122 Sq Ft
    • Built 1954

    Last Sold Summary

    • 23% Below List Price
    • $258/SF
    • 464 Days On Market

    Current Estimated Value $297,810

    Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

    1908 Carrigan Ave, Winter Park, FL 32792
  • 1771 Winchester Dr, Winter Park, FL 32789
    1771 Winchester Dr, Winter Park, FL 32789
    /2

    $1,395,000 Sold Mar 26, 2025

    1771 Winchester Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,516 Sq Ft
    • Built 1957

    Last Sold Summary

    • $554/SF
    • 0 Days On Market

    Current Estimated Value $1,390,609

    Last Listing Agent Michael Ford FANNIE HILLMAN & ASSOCIATES

    1771 Winchester Dr, Winter Park, FL 32789
  • 2350 Sherbrooke Rd, Winter Park, FL 32792
    2350 Sherbrooke Rd, Winter Park, FL 32792
    /2

    $779,000 Sold Jan 17, 2025

    2350 Sherbrooke Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft
    • Built 1967

    Last Sold Summary

    • 8% Below List Price
    • $354/SF
    • 106 Days On Market

    Current Estimated Value $763,406

    Last Listing Agent Alexa Monasterio Flores KELLER WILLIAMS ADVANTAGE 2 REALTY

    2350 Sherbrooke Rd, Winter Park, FL 32792
  • 513 Cornwall Rd, Winter Park, FL 32792
    513 Cornwall Rd, Winter Park, FL 32792
    /2

    $527,500 Sold Apr 04, 2025

    513 Cornwall Rd, Winter Park, FL 32792

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

    Last Sold Summary

    • 12% Below List Price
    • $304/SF
    • 55 Days On Market

    Current Estimated Value $527,417

    Last Listing Agent Michelle Deleon BHHS FLORIDA REALTY

    513 Cornwall Rd, Winter Park, FL 32792
  • 851 Miles Ave Unit 8, Winter Park, FL 32789
    851 Miles Ave Unit 8, Winter Park, FL 32789
    /2

    $199,000 Sold Aug 01, 2025

    851 Miles Ave Unit 8, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 808 Sq Ft
    • Built 1984

    Last Sold Summary

    • 12% Below List Price
    • $246/SF
    • 16 Days On Market

    Current Estimated Value $203,812

    Last Listing Agent Bobby Christiano COLDWELL BANKER RESIDENTIAL RE

    851 Miles Ave Unit 8, Winter Park, FL 32789
  • 2907 Summerfield Rd, Winter Park, FL 32792
    2907 Summerfield Rd, Winter Park, FL 32792
    /2

    $749,000 Sold Jun 16, 2025

    2907 Summerfield Rd, Winter Park, FL 32792

    • 5 Beds
    • 2 Baths
    • 2,532 Sq Ft
    • Built 1968

    Last Sold Summary

    • $296/SF
    • 3 Days On Market

    Current Estimated Value $740,512

    Last Listing Agent Kim Helmling MILLER GRANT AND COMPANY

    2907 Summerfield Rd, Winter Park, FL 32792

Showing Results 481 - 520, Page 13 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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