1,102

Recently Sold Winter Park, FL Homes

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  • /2

    $222,500

    Sold Aug 03, 2026

    7771 Country Place Unit 7, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,230 Sq Ft
    • Built 1987

    Last Sold Summary

    • 7% Below List Price
    • $181/SF
    • 189 Days On Market

    Current Estimated Value $217,930

    Last Listing Agent Ivan Tobon OUTLET REALTY

    7771 Country Place Unit 7, Winter Park, FL 32792
  • /2

    $332,000

    Sold Oct 20, 2025

    3490 Bougainvillea Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,461 Sq Ft
    • Built 1960

    Last Sold Summary

    • 12% Below List Price
    • $227/SF
    • 39 Days On Market

    Current Estimated Value $335,159

    Last Listing Agent EJ Jimenez KELLER WILLIAMS ADVANTAGE III

    3490 Bougainvillea Dr, Winter Park, FL 32792
  • /2

    $445,000

    Sold Jan 22, 2026

    2743 Merrie Oaks Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,661 Sq Ft
    • Built 1966

    Last Sold Summary

    • 1% Above List Price
    • $268/SF
    • 9 Days On Market

    Current Estimated Value $448,467

    Last Listing Agent Julio Zayas ONE45 REALTY LLC

    2743 Merrie Oaks Rd, Winter Park, FL 32792
  • /2

    $1,675,000

    Sold May 08, 2026

    1560 Woodland Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,851 Sq Ft
    • Built 1990

    Last Sold Summary

    • 9% Below List Price
    • $435/SF
    • 16 Days On Market

    Current Estimated Value $1,698,693

    Last Listing Agent Chris Creegan CREEGAN GROUP

    1560 Woodland Ave, Winter Park, FL 32789
  • /2

    $800,000

    Sold Apr 13, 2026

    1183 Wildmeadow Run, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,020 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Below List Price
    • $265/SF
    • 43 Days On Market

    Current Estimated Value $802,658

    Last Listing Agent Kara Lushear COLDWELL BANKER REALTY

    1183 Wildmeadow Run, Winter Park, FL 32792
  • /2

    $455,000

    Sold Dec 29, 2025

    1116 Fairway Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,738 Sq Ft
    • Built 1978

    Last Sold Summary

    • 24% Below List Price
    • $262/SF
    • 333 Days On Market

    Current Estimated Value $484,230

    Last Listing Agent Mathew Kelly TURN-KEY MOVES REALTY

    1116 Fairway Dr, Winter Park, FL 32792
  • /2

    $2,232,000

    Sold Apr 17, 2026

    660 Osceola Ave Unit 101, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,714 Sq Ft
    • Built 1999

    Last Sold Summary

    • 3% Below List Price
    • $822/SF
    • 145 Days On Market

    Current Estimated Value $2,185,609

    Last Listing Agent Richard Traynor FLORIDA ONE REAL ESTATE LLC

    660 Osceola Ave Unit 101, Winter Park, FL 32789
  • /2

    $250,000

    Sold Oct 06, 2025

    200 Saint Andrews Blvd Unit 1004, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,322 Sq Ft
    • Built 1970

    Last Sold Summary

    • 17% Below List Price
    • $189/SF
    • 157 Days On Market

    Current Estimated Value $254,951

    Last Listing Agent Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

    200 Saint Andrews Blvd Unit 1004, Winter Park, FL 32792
  • /2

    $300,000

    Sold Mar 27, 2026

    1313 S Denning Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 1950

    Last Sold Summary

    • $176/SF

    Current Estimated Value $324,389

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

    1313 S Denning Dr, Winter Park, FL 32789
  • /2

    $360,000

    Sold Nov 20, 2025

    611 Ololu Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,145 Sq Ft
    • Built 1973

    Last Sold Summary

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

    Current Estimated Value $376,452

    Last Listing Agent Amanda Johnson HOMERUN REALTY, LLC

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

    $2,500,000

    Sold Oct 31, 2025

    2652 Lake Howell Ln, Winter Park, FL 32792

    • 5 Beds
    • 3.5 Baths
    • 3,898 Sq Ft
    • Built 1954

    Last Sold Summary

    • 12% Below List Price
    • $641/SF
    • 64 Days On Market

    Current Estimated Value $2,421,380

    Last Listing Agent Brigitte Elzarki COLDWELL BANKER REALTY

    2652 Lake Howell Ln, Winter Park, FL 32792
  • /2

    $385,000

    Sold Apr 21, 2026

    2232 Shadowland Loop, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft
    • Built 2021

    Last Sold Summary

    • 10% Below List Price
    • $219/SF
    • 77 Days On Market

    Current Estimated Value $389,140

    Last Listing Agent He Gao U S GLORY REALTY

    2232 Shadowland Loop, Winter Park, FL 32792
  • /2

    $1,535,000

    Sold Mar 30, 2026

    507 Country Club Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,985 Sq Ft
    • Built 2020

    Last Sold Summary

    • 1% Below List Price
    • $514/SF
    • 27 Days On Market

    Current Estimated Value $1,541,393

    Last Listing Agent Lianna D'Angelo SOTERA LIVING

    507 Country Club Dr, Winter Park, FL 32789
  • /2

    $640,000

    Sold Jun 29, 2026

    1618 Indiana Ave, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 1,604 Sq Ft
    • Built 1963

    Last Sold Summary

    • 7% Below List Price
    • $399/SF
    • 49 Days On Market

    Current Estimated Value $657,046

    Last Listing Agent Johnathan Lam NATIONAL REAL ESTATE

    1618 Indiana Ave, Winter Park, FL 32789
  • /2

    $1,000,500

    Sold Dec 11, 2025

    210 E Rockwood Way, Winter Park, FL 32789

    • 3 Beds
    • 1.5 Baths
    • 1,431 Sq Ft
    • Built 1950

    Last Sold Summary

    • $699/SF
    • 0 Days On Market

    Current Estimated Value $1,070,017

    Last Listing Agent Penny Puente DALTON WADE INC

    210 E Rockwood Way, Winter Park, FL 32789
  • /2

    $519,000

    Sold Jun 30, 2026

    1944 Natalen Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 1957

    Last Sold Summary

    • $376/SF
    • 10 Days On Market

    Current Estimated Value $514,863

    Last Listing Agent Trevor Thomas EMPIRE NETWORK REALTY

    1944 Natalen Rd, Winter Park, FL 32792
  • /2

    $350,000

    Sold Oct 22, 2025

    5128 Lake Howell Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,220 Sq Ft
    • Built 1957

    Last Sold Summary

    • $287/SF
    • 12 Days On Market

    Current Estimated Value $345,035

    Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

    5128 Lake Howell Rd, Winter Park, FL 32792
  • /2

    $555,000

    Sold Jan 29, 2026

    1267 Michigan Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,798 Sq Ft
    • Built 2019

    Last Sold Summary

    • 17% Below List Price
    • $309/SF
    • 88 Days On Market

    Current Estimated Value $457,888

    Last Listing Agent Megan Cross FANNIE HILLMAN & ASSOCIATES

    1267 Michigan Ave, Winter Park, FL 32789
  • /2

    $450,000

    Sold Mar 31, 2026

    764 W Comstock Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 925 Sq Ft
    • Built 1935

    Last Sold Summary

    • 5% Below List Price
    • $486/SF
    • 17 Days On Market

    Current Estimated Value $451,679

    Last Listing Agent Manny del Valle KELLER WILLIAMS WINTER PARK

    764 W Comstock Ave, Winter Park, FL 32789
  • /2

    $4,950,000

    Sold Jul 30, 2026

    1660 Palmer Ave, Winter Park, FL 32789

    • 5 Beds
    • 6.5 Baths
    • 5,636 Sq Ft
    • Built 2024

    Last Sold Summary

    • 13% Below List Price
    • $878/SF
    • 438 Days On Market

    Current Estimated Value $3,711,995

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

    1660 Palmer Ave, Winter Park, FL 32789
  • /2

    $900,000

    Sold Aug 29, 2025

    3011 Temple Trail, Winter Park, FL 32789

    • 5 Beds
    • 2.5 Baths
    • 2,406 Sq Ft
    • Built 1965

    Last Sold Summary

    • 10% Below List Price
    • $374/SF
    • 83 Days On Market

    Current Estimated Value $933,653

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    3011 Temple Trail, Winter Park, FL 32789
  • /2

    $4,150,000

    Sold Feb 18, 2026

    702 Via Bella, Winter Park, FL 32789

    • 4 Beds
    • 5.5 Baths
    • 3,720 Sq Ft
    • Built 2025

    Last Sold Summary

    • 11% Below List Price
    • $1,116/SF
    • 149 Days On Market

    Current Estimated Value $3,621,837

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

    702 Via Bella, Winter Park, FL 32789
  • /2

    $360,000

    Sold Oct 09, 2025

    1309 Paradise Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,606 Sq Ft
    • Built 1984

    Last Sold Summary

    • 15% Below List Price
    • $224/SF
    • 242 Days On Market

    Current Estimated Value $378,134

    Last Listing Agent Barbara Mills COLDWELL BANKER REALTY

    1309 Paradise Ln, Winter Park, FL 32792
  • /2

    $190,000

    Sold Mar 20, 2026

    1250 S Denning Dr Unit 104, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 908 Sq Ft
    • Built 1967

    Last Sold Summary

    • 17% Below List Price
    • $209/SF
    • 60 Days On Market

    Current Estimated Value $194,685

    Last Listing Agent John Harbuck SERHANT

    1250 S Denning Dr Unit 104, Winter Park, FL 32789
  • /2

    $368,500

    Sold Apr 03, 2026

    958 Dupont Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft
    • Built 1956

    Last Sold Summary

    • 3% Below List Price
    • $234/SF
    • 49 Days On Market

    Current Estimated Value $371,934

    Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

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

    $60,000

    Sold Feb 19, 2026

    3028 George Mason Ave Unit 7, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,088 Sq Ft
    • Built 1974

    Last Sold Summary

    • 50% Above List Price
    • $55/SF
    • 87 Days On Market

    Last Listing Agent David Rollins FLORIDA REALTY INVESTMENTS

    3028 George Mason Ave Unit 7, Winter Park, FL 32792
  • /2

    $1,650,000

    Sold May 01, 2026

    1016 Howell Branch Rd, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Below List Price
    • $525/SF
    • 7 Days On Market

    Current Estimated Value $1,633,057

    Last Listing Agent Andrew Birr PLAID PROPERTIES, LLC

    1016 Howell Branch Rd, Winter Park, FL 32789
  • /2

    $205,000

    Sold Dec 09, 2025

    200 Saint Andrews Blvd Unit 1707, Winter Park, FL 32792

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

    Last Sold Summary

    • 5% Below List Price
    • $168/SF
    • 14 Days On Market

    Current Estimated Value $213,081

    Last Listing Agent Tiffany Yates COMPASS FLORIDA LLC

    200 Saint Andrews Blvd Unit 1707, Winter Park, FL 32792
  • /2

    $810,000

    Sold Nov 26, 2025

    1314 Canterbury Rd, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,738 Sq Ft
    • Built 1950

    Last Sold Summary

    • $466/SF

    Current Estimated Value $829,296

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

    1314 Canterbury Rd, Winter Park, FL 32789
  • /2

    $325,000

    Sold Mar 06, 2026

    5047 Ferncrest Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,242 Sq Ft
    • Built 1969

    Last Sold Summary

    • 7% Below List Price
    • $262/SF
    • 67 Days On Market

    Current Estimated Value $328,306

    Last Listing Agent Wanda Perkins GLOBAL PROPERTIES SALES & MGMT

    5047 Ferncrest Dr, Winter Park, FL 32792
  • /2

    $892,500

    Sold Jun 25, 2026

    1960 E Winter Park Rd, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 1,864 Sq Ft
    • Built 1948

    Last Sold Summary

    • 1% Below List Price
    • $479/SF
    • 13 Days On Market

    Current Estimated Value $912,809

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1960 E Winter Park Rd, Winter Park, FL 32789
  • /2

    $887,500

    Sold Jun 11, 2026

    627 Dunblane Dr, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,086 Sq Ft
    • Built 1962

    Last Sold Summary

    • 1% Below List Price
    • $425/SF
    • 5 Days On Market

    Current Estimated Value $874,649

    Last Listing Agent Steven Ritz KELLER WILLIAMS WINTER PARK

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

    $485,000

    Sold Feb 03, 2026

    131 Stefanik Rd, Winter Park, FL 32792

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • Built 1980

    Last Sold Summary

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

    Last Listing Agent Thomas McNamara EXP REALTY LLC

    131 Stefanik Rd, Winter Park, FL 32792
  • /2

    $449,999

    Sold Aug 22, 2025

    7446 Houston Ct E, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,795 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Below List Price
    • $251/SF
    • 56 Days On Market

    Current Estimated Value $445,842

    Last Listing Agent Walter Taylor KELLER WILLIAMS REALTY AT THE PARKS

    7446 Houston Ct E, Winter Park, FL 32792
  • /2

    $455,000

    Sold Oct 03, 2025

    1157 Valley Creek Run, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,171 Sq Ft
    • Built 1995

    Last Sold Summary

    • 16% Below List Price
    • $210/SF
    • 133 Days On Market

    Current Estimated Value $472,654

    Last Listing Agent Roberta Shoopman CHARLES RUTENBERG REALTY ORLANDO

    1157 Valley Creek Run, Winter Park, FL 32792
  • /2

    $349,000

    Sold Aug 29, 2025

    1050 Reading Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,637 Sq Ft
    • Built 1983

    Last Sold Summary

    • 8% Below List Price
    • $213/SF
    • 52 Days On Market

    Current Estimated Value $377,968

    Last Listing Agent Carmen Vazquez REALTY TECH INC

    1050 Reading Ct, Winter Park, FL 32792
  • /2

    $1,755,000

    Sold Jul 24, 2026

    1813 Harland Park Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,551 Sq Ft
    • Built 2013

    Last Sold Summary

    • 12% Below List Price
    • $494/SF
    • 67 Days On Market

    Current Estimated Value $1,851,965

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1813 Harland Park Dr, Winter Park, FL 32789
  • /2

    $4,500,000

    Sold May 29, 2026

    1521 Harris Cir, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,922 Sq Ft
    • Built 2026

    Last Sold Summary

    • $1,147/SF
    • 0 Days On Market

    Current Estimated Value $2,081,033

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

    1521 Harris Cir, Winter Park, FL 32789
  • /2

    $287,500

    Sold Jun 29, 2026

    4428 Steed Terrace, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 1990

    Last Sold Summary

    • $160/SF

    Current Estimated Value $441,467

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

    4428 Steed Terrace, Winter Park, FL 32792
  • /2

    $290,000

    Sold Jul 15, 2026

    184 Sandlewood Trail Unit 2, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 1,133 Sq Ft
    • Built 1985

    Last Sold Summary

    • 12% Below List Price
    • $256/SF
    • 141 Days On Market

    Current Estimated Value $293,978

    Last Listing Agent Tom Noelke NOELKE REALTY

    184 Sandlewood Trail Unit 2, Winter Park, FL 32789

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