1,126

Recently Sold Winter Park, FL Homes

Section Image
  • 443 S Lakemont Ave, Winter Park, FL 32792
    443 S Lakemont Ave, Winter Park, FL 32792
    /2

    $450,000 Sold Dec 29, 2025

    443 S Lakemont Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,364 Sq Ft
    • Built 1955

    Last Sold Summary

    • $330/SF
    • 0 Days On Market

    Current Estimated Value $458,414

    Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

    443 S Lakemont Ave, Winter Park, FL 32792
  • 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 $559,464

    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

    Current Estimated Value $2,209,943

    Last Listing Agent David Francetic COLDWELL BANKER REALTY

    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 $642,996

    Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    796 Mcintyre Ave, Winter Park, FL 32789
  • 1875 Staunton Ave, Winter Park, FL 32789
    1875 Staunton Ave, Winter Park, FL 32789
    /2

    $560,000 Sold Jan 27, 2026

    1875 Staunton Ave, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 2,036 Sq Ft
    • Built 1954

    Last Sold Summary

    • 3% Below List Price
    • $275/SF
    • 89 Days On Market

    Current Estimated Value $555,813

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    1875 Staunton Ave, Winter Park, FL 32789
  • 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 $621,481

    Last Listing Agent Rhonda Hunter COLDWELL BANKER REALTY

    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 $587,372

    Last Listing Agent Karen Ripperger LPT REALTY, LLC

    1368 Devon Rd, Winter Park, FL 32789
  • 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 $2,884,132

    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 $706,218

    Last Listing Agent Erin Tompkins COLDWELL BANKER REALTY

    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 $2,080,018

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

    104 Cortland Ave, Winter Park, FL 32789
  • 4591 Whimbrel Place, Winter Park, FL 32792
    4591 Whimbrel Place, Winter Park, FL 32792
    /2

    $480,000 Sold Mar 03, 2026

    4591 Whimbrel Place, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,942 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Below List Price
    • $247/SF
    • 0 Days On Market

    Current Estimated Value $481,445

    Last Listing Agent Nicole Wilbur CHARLES RUTENBERG REALTY ORLANDO

    4591 Whimbrel Place, Winter Park, FL 32792
  • 623 Saint Johns Ct Unit 623, Winter Park, FL 32792
    623 Saint Johns Ct Unit 623, Winter Park, FL 32792
    /2

    $192,000 Sold Feb 24, 2026

    623 Saint Johns Ct Unit 623, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1981

    Last Sold Summary

    • 15% Below List Price
    • $171/SF
    • 28 Days On Market

    Current Estimated Value $198,828

    Last Listing Agent David Dorman CENTURY 21 CARIOTI

    623 Saint Johns Ct Unit 623, 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 $571,049

    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 $756,631

    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 $495,043

    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 $385,888

    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

    Current Estimated Value $814,465

    Last Listing Agent Michael Domi COMPASS FLORIDA LLC

    734 Maryland Ave, 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

    Current Estimated Value $761,083

    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 $168,948

    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

    Current Estimated Value $412,927

    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 $856,452

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    1919 S Lakemont Ave, Winter Park, FL 32792
  • 2074 Laurelwood Way, Winter Park, FL 32792
    2074 Laurelwood Way, Winter Park, FL 32792
    /2

    $755,000 Sold Dec 30, 2025

    2074 Laurelwood Way, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,192 Sq Ft
    • Built 2019

    Last Sold Summary

    • 4% Below List Price
    • $344/SF
    • 8 Days On Market

    Current Estimated Value $757,030

    Last Listing Agent Janki Thakkar DJ & LINDSEY REAL ESTATE

    2074 Laurelwood Way, 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 $723,036

    Last Listing Agent Erica Diltz BALDWIN PARK REALTY LLC

    2178 Whitehall Dr, Winter Park, FL 32792
  • 1921 Taylor Ave, Winter Park, FL 32792
    1921 Taylor Ave, Winter Park, FL 32792
    /2

    $415,000 Sold Dec 25, 2025

    1921 Taylor Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,322 Sq Ft
    • Built 1956

    Last Sold Summary

    • 1% Above List Price
    • $314/SF
    • 167 Days On Market

    Current Estimated Value $409,554

    Last Listing Agent Brianna Perez Montalvo EXP REALTY LLC

    1921 Taylor Ave, 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 $91,397

    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 $293,819

    Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

    1908 Carrigan Ave, 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 $637,578

    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 $193,592

    Last Listing Agent Bobby Christiano COLDWELL BANKER REALTY

    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 $732,963

    Last Listing Agent Kim Helmling MILLER GRANT AND COMPANY

    2907 Summerfield Rd, Winter Park, FL 32792
  • 1871 Casselwood St, Winter Park, FL 32792
    1871 Casselwood St, Winter Park, FL 32792
    /2

    $270,000 Sold Oct 15, 2025

    1871 Casselwood St, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,616 Sq Ft
    • Built 1988

    Last Sold Summary

    • 16% Below List Price
    • $167/SF
    • 33 Days On Market

    Current Estimated Value $279,887

    Last Listing Agent Nicholas Zervos ERA GRIZZARD REAL ESTATE

    1871 Casselwood St, Winter Park, FL 32792
  • 1921 Heathwood Dr, Winter Park, FL 32792
    1921 Heathwood Dr, Winter Park, FL 32792
    /2

    $300,000 Sold Apr 28, 2025

    1921 Heathwood Dr, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 1,611 Sq Ft
    • Built 1980

    Last Sold Summary

    • $186/SF
    • 0 Days On Market

    Current Estimated Value $448,940

    Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    1921 Heathwood Dr, Winter Park, FL 32792
  • 4041 Yacht Ct, Winter Park, FL 32792
    4041 Yacht Ct, Winter Park, FL 32792
    /2

    $593,000 Sold Jul 01, 2025

    4041 Yacht Ct, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 2,153 Sq Ft
    • Built 1977

    Last Sold Summary

    • 20% Below List Price
    • $275/SF
    • 297 Days On Market

    Current Estimated Value $584,073

    Last Listing Agent Andrew Livingston COLDWELL BANKER REALTY

    4041 Yacht Ct, Winter Park, FL 32792
  • 2405 Firstlight Way, Winter Park, FL 32792
    2405 Firstlight Way, Winter Park, FL 32792
    /2

    $455,000 Sold Oct 27, 2025

    2405 Firstlight Way, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft
    • Built 2019

    Last Sold Summary

    • 3% Below List Price
    • $232/SF
    • 91 Days On Market

    Current Estimated Value $444,831

    Last Listing Agent Carmen Acosta EXP REALTY LLC

    2405 Firstlight Way, Winter Park, FL 32792
  • 535 N Interlachen Ave Unit 107, Winter Park, FL 32789
    535 N Interlachen Ave Unit 107, Winter Park, FL 32789
    /2

    $412,000 Sold Aug 22, 2025

    535 N Interlachen Ave Unit 107, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,088 Sq Ft
    • Built 1972

    Last Sold Summary

    • 18% Below List Price
    • $379/SF
    • 127 Days On Market

    Current Estimated Value $415,031

    Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

    535 N Interlachen Ave Unit 107, Winter Park, FL 32789
  • 1640 Mayfield Ave, Winter Park, FL 32789
    1640 Mayfield Ave, Winter Park, FL 32789
    /2

    $1,785,000 Sold Sep 11, 2025

    1640 Mayfield Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,907 Sq Ft
    • Built 1953

    Last Sold Summary

    • 1% Below List Price
    • $614/SF
    • 29 Days On Market

    Current Estimated Value $1,760,450

    Last Listing Agent Beverly Brown RE/MAX PRIME PROPERTIES

    1640 Mayfield Ave, Winter Park, FL 32789
  • 3025 Northwood Blvd, Winter Park, FL 32789
    3025 Northwood Blvd, Winter Park, FL 32789
    /2

    $520,000 Sold Nov 24, 2025

    3025 Northwood Blvd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft
    • Built 1953

    Last Sold Summary

    • 5% Below List Price
    • $336/SF
    • 2 Days On Market

    Current Estimated Value $519,609

    Last Listing Agent Alie Gattis MAINFRAME REAL ESTATE

    3025 Northwood Blvd, Winter Park, FL 32789
  • 3529 Australian Cir, Winter Park, FL 32792
    3529 Australian Cir, Winter Park, FL 32792
    /2

    $398,000 Sold Nov 24, 2025

    3529 Australian Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,255 Sq Ft
    • Built 1963

    Last Sold Summary

    • $317/SF
    • 8 Days On Market

    Current Estimated Value $388,278

    Last Listing Agent Lori Hoover EXP REALTY LLC

    3529 Australian Cir, Winter Park, FL 32792
  • 5234 Ohio St, Winter Park, FL 32792
    5234 Ohio St, Winter Park, FL 32792
    /2

    $405,000 Sold Sep 12, 2025

    5234 Ohio St, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,226 Sq Ft
    • Built 1973

    Last Sold Summary

    • 6% Above List Price
    • $330/SF
    • 15 Days On Market

    Current Estimated Value $388,435

    Last Listing Agent Emily Nickley MARKET CONNECT REALTY LLC

    5234 Ohio St, Winter Park, FL 32792
  • 2308 Mulbry Dr, Winter Park, FL 32789
    2308 Mulbry Dr, Winter Park, FL 32789
    /2

    $502,000 Sold Oct 30, 2025

    2308 Mulbry Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft
    • Built 1952

    Last Sold Summary

    • 9% Below List Price
    • $352/SF
    • 4 Days On Market

    Current Estimated Value $512,242

    Last Listing Agent Daniel Sposato BALDWIN PARK REALTY LLC

    2308 Mulbry Dr, Winter Park, FL 32789
  • 2607 Verde Ln, Winter Park, FL 32792
    2607 Verde Ln, Winter Park, FL 32792
    /2

    $515,000 Sold Jun 25, 2025

    2607 Verde Ln, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,953 Sq Ft
    • Built 1968

    Last Sold Summary

    • 6% Below List Price
    • $264/SF
    • 68 Days On Market

    Current Estimated Value $498,624

    Last Listing Agent David Wald FOUNDERS REALTY GROUP

    2607 Verde Ln, 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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