1,107

Recently Sold Winter Park, FL Homes

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  • /2

    $4,500,000

    Sold Apr 30, 2026

    887 Georgia Ave, Winter Park, FL 32789

    • 6 Beds
    • 5.5 Baths
    • 5,759 Sq Ft
    • Built 1924

    Last Sold Summary

    • 31% Below List Price
    • $781/SF
    • 222 Days On Market

    Current Estimated Value $4,507,670

    Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

    887 Georgia Ave, Winter Park, FL 32789
  • /2

    $75,000

    Sold Nov 20, 2025

    3053 George Mason Ave Unit 7, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft
    • Built 1974

    Last Sold Summary

    • 25% Below List Price
    • $73/SF
    • 85 Days On Market

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    3053 George Mason Ave Unit 7, Winter Park, FL 32792
  • /2

    $110,000

    Sold Sep 15, 2025

    1000 S Semoran Blvd Unit 415, Winter Park, FL 32792

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

    Last Sold Summary

    • 18% Below List Price
    • $150/SF
    • 78 Days On Market

    Current Estimated Value $111,257

    Last Listing Agent Jhoana Loyo Urrutia LPT REALTY, LLC

    1000 S Semoran Blvd Unit 415, Winter Park, FL 32792
  • /2

    $465,000

    Sold Oct 21, 2025

    130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 1,536 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Below List Price
    • $303/SF
    • 75 Days On Market

    Current Estimated Value $452,889

    Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

    130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
  • /2

    $1,555,000

    Sold Sep 12, 2025

    817 Antonette Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 3,971 Sq Ft
    • Built 1990

    Last Sold Summary

    • 22% Below List Price
    • $392/SF
    • 146 Days On Market

    Current Estimated Value $1,632,561

    Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

    817 Antonette Ave, Winter Park, FL 32789
  • /2

    $363,000

    Sold Jan 23, 2026

    1436 Auburn Green Loop, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,415 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Above List Price
    • $257/SF
    • 9 Days On Market

    Current Estimated Value $367,024

    Last Listing Agent Victoria Myers RE/MAX TOWN & COUNTRY REALTY

    1436 Auburn Green Loop, Winter Park, FL 32792
  • /2

    $3,278,530

    Sold May 20, 2026

    700 Pinetree Rd, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,897 Sq Ft
    • Built 1955

    Last Sold Summary

    • $841/SF
    • 1 Day On Market

    Current Estimated Value $3,111,413

    Last Listing Agent Lauren Richardson FANNIE HILLMAN & ASSOCIATES

    700 Pinetree Rd, Winter Park, FL 32789
  • /2

    $367,500

    Sold Nov 17, 2025

    1975 Staunton Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1949

    Last Sold Summary

    • 15% Below List Price
    • $306/SF
    • 225 Days On Market

    Current Estimated Value $371,259

    Last Listing Agent Marion McGrath ABSOLUTE REALTY GROUP, LLC

    1975 Staunton Ave, Winter Park, FL 32789
  • /2

    $375,000

    Sold Jun 10, 2026

    4923 N Magnolia Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,559 Sq Ft
    • Built 1953

    Last Sold Summary

    • 4% Below List Price
    • $241/SF
    • 0 Days On Market

    Current Estimated Value $375,163

    Last Listing Agent Deanna Chance A+ REALTY PROFESSIONALS, INC

    4923 N Magnolia Ave, Winter Park, FL 32792
  • /2

    $419,900

    Sold Jul 10, 2026

    1871 Casselwood St, Winter Park, FL 32792

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

    Last Sold Summary

    • 1% Below List Price
    • $260/SF
    • 24 Days On Market

    Current Estimated Value $410,721

    Last Listing Agent Alexa Monasterio Flores KELLER WILLIAMS ADVANTAGE 2 REALTY

    1871 Casselwood St, Winter Park, FL 32792
  • /2

    $1,250,000

    Sold Aug 29, 2025

    1621 Hillcrest Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,755 Sq Ft
    • Built 1947

    Last Sold Summary

    • $454/SF
    • 0 Days On Market

    Current Estimated Value $1,292,905

    Last Listing Agent Julie Glass KEYSEEKERS REAL ESTATE

    1621 Hillcrest Ave, Winter Park, FL 32789
  • /2

    $749,900

    Sold Oct 14, 2025

    1465 Lone Feather Trail, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 2,582 Sq Ft
    • Built 2021

    Last Sold Summary

    • $290/SF
    • 11 Days On Market

    Current Estimated Value $762,450

    Last Listing Agent Chris Watts THE TEAM REAL ESTATE GROUP INC

    1465 Lone Feather Trail, Winter Park, FL 32792
  • /2

    $6,300,000

    Sold Nov 04, 2025

    1308 Green Cove Rd, Winter Park, FL 32789

    • 4 Beds
    • 5.5 Baths
    • 6,981 Sq Ft
    • Built 1990

    Last Sold Summary

    • $902/SF
    • 0 Days On Market

    Current Estimated Value $6,378,104

    Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

    1308 Green Cove Rd, Winter Park, FL 32789
  • /2

    $445,000

    Sold Dec 17, 2025

    2380 Shadowland Loop, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 2,076 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Below List Price
    • $214/SF
    • 45 Days On Market

    Current Estimated Value $451,558

    Last Listing Agent Cristian Cen Chen SIMPSON REALTY LLC

    2380 Shadowland Loop, Winter Park, FL 32792
  • /2

    $310,000

    Sold Apr 30, 2026

    736 Warrenton Rd, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Above List Price
    • $235/SF
    • 5 Days On Market

    Current Estimated Value $306,295

    Last Listing Agent Andrea Parra FANNIE HILLMAN & ASSOCIATES

    736 Warrenton Rd, Winter Park, FL 32792
  • /2

    $1,635,000

    Sold May 11, 2026

    1841 Harland Park Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,470 Sq Ft
    • Built 2014

    Last Sold Summary

    • 18% Below List Price
    • $471/SF
    • 103 Days On Market

    Current Estimated Value $1,674,993

    Last Listing Agent Shanon Luiz SELECTIVE REALTY GROUP LLC

    1841 Harland Park Dr, Winter Park, FL 32789
  • /2

    $1,450,000

    Sold Jul 31, 2026

    1660 Walnut Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,249 Sq Ft
    • Built 2026

    Last Sold Summary

    • 12% Below List Price
    • $645/SF
    • 43 Days On Market

    Current Estimated Value $1,513,256

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

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

    $315,000

    Sold Mar 27, 2026

    2249 Minnesota Ave, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1955

    Last Sold Summary

    • 28% Below List Price
    • $205/SF
    • 42 Days On Market

    Current Estimated Value $370,022

    Last Listing Agent Emily Nickley MARKET CONNECT REALTY LLC

    2249 Minnesota Ave, Winter Park, FL 32789
  • /2

    $480,000

    Sold May 21, 2026

    1210 Fairway Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,737 Sq Ft
    • Built 1979

    Last Sold Summary

    • 13% Below List Price
    • $276/SF
    • 11 Days On Market

    Current Estimated Value $500,278

    Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1210 Fairway Dr, Winter Park, FL 32792
  • /2

    $485,000

    Sold Jun 15, 2026

    2707 Tierra Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft
    • Built 1970

    Last Sold Summary

    • 2% Below List Price
    • $284/SF
    • 21 Days On Market

    Current Estimated Value $485,292

    Last Listing Agent Hannah True RE/MAX 200 REALTY

    2707 Tierra Cir, Winter Park, FL 32792
  • /2

    $198,000

    Sold Feb 20, 2026

    7457 Belle River Ct Unit 12, Winter Park, FL 32792

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

    Last Sold Summary

    • 6% Below List Price
    • $192/SF
    • 88 Days On Market

    Current Estimated Value $197,421

    Last Listing Agent Jasmin Cabral LIFESTYLE INTERNATIONAL REALTY

    7457 Belle River Ct Unit 12, Winter Park, FL 32792
  • /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

    Current Estimated Value $4,508,554

    Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

    2161 Sharon Rd, Winter Park, FL 32789
  • /2

    $675,000

    Sold Jul 20, 2026

    7740 Lake Dawn Dr, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 2,495 Sq Ft
    • Built 1959

    Last Sold Summary

    • 7% Below List Price
    • $271/SF
    • 24 Days On Market

    Current Estimated Value $675,597

    Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

    7740 Lake Dawn Dr, 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 $478,344

    Last Listing Agent Peter Hamilton DAHLIA REALTY GROUP

    3304 Bennington Ct, Winter Park, FL 32792
  • /2

    $913,000

    Sold Jul 27, 2026

    422 Balmoral Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1957

    Last Sold Summary

    • $507/SF
    • 0 Days On Market

    Current Estimated Value $836,762

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

    422 Balmoral 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

    Current Estimated Value $1,624,226

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1450 Glencoe Rd, Winter Park, FL 32789
  • /2

    $660,000

    Sold Jun 29, 2026

    927 Fairway Dr, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,918 Sq Ft
    • Built 1973

    Last Sold Summary

    • 6% Below List Price
    • $344/SF
    • 40 Days On Market

    Current Estimated Value $679,977

    Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

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

    $414,000

    Sold Feb 19, 2026

    740 Baffie Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1960

    Last Sold Summary

    • 12% Below List Price
    • $284/SF
    • 94 Days On Market

    Current Estimated Value $419,135

    Last Listing Agent Chris Creegan CREEGAN GROUP

    740 Baffie Ave, Winter Park, FL 32789
  • /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 $239,695

    Last Listing Agent Michael Wood UNITED REAL ESTATE PREFERRED

    2480 Tahoe Cir, Winter Park, FL 32792
  • /2

    $194,995

    Sold May 26, 2026

    4790 Tangerine Ave Unit 4790, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,058 Sq Ft
    • Built 1973

    Last Sold Summary

    • 13% Below List Price
    • $184/SF
    • 71 Days On Market

    Current Estimated Value $195,671

    Last Listing Agent Sonny Manku SUNSHINE BROKERAGE, LLC

    4790 Tangerine Ave Unit 4790, 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 $471,212

    Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

    443 S Lakemont Ave, Winter Park, FL 32792
  • /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 $2,262,256

    Last Listing Agent David Francetic COLDWELL BANKER REALTY

    600 Ololu Dr, 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 $565,342

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

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

    $324,000

    Sold Aug 07, 2026

    2676 Barbados Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,743 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $186/SF
    • 26 Days On Market

    Current Estimated Value $336,789

    Last Listing Agent Joseph Sipp KELLER WILLIAMS WINTER PARK

    2676 Barbados Dr, Winter Park, FL 32792
  • /2

    $73,500

    Sold May 21, 2026

    3053 George Mason Ave Unit 8, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 809 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Below List Price
    • $91/SF
    • 3 Days On Market

    Last Listing Agent Carmen Quintana COLDWELL BANKER REALTY

    3053 George Mason Ave Unit 8, Winter Park, FL 32792
  • /2

    $760,000

    Sold May 13, 2026

    2919 Bower Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,325 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Below List Price
    • $327/SF
    • 22 Days On Market

    Current Estimated Value $758,610

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    2919 Bower Rd, Winter Park, FL 32792
  • /2

    $445,000

    Sold Jul 30, 2026

    3009 Nicholson Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,645 Sq Ft
    • Built 1980

    Last Sold Summary

    • 1% Below List Price
    • $271/SF
    • 3 Days On Market

    Current Estimated Value $387,711

    Last Listing Agent Benjamin Simanton LPT REALTY, LLC

    3009 Nicholson Dr, 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 $481,584

    Last Listing Agent Nicole Wilbur CHARLES RUTENBERG REALTY ORLANDO

    4591 Whimbrel Place, 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 $198,002

    Last Listing Agent David Dorman CENTURY 21 CARIOTI

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

    $620,000

    Sold Apr 10, 2026

    1137 Oaks Blvd, Winter Park, FL 32789

    • 2 Beds
    • 1.5 Baths
    • 1,149 Sq Ft
    • Built 1958

    Last Sold Summary

    • 4% Below List Price
    • $540/SF
    • 44 Days On Market

    Current Estimated Value $615,403

    Last Listing Agent David Gallup RE/MAX 200 REALTY

    1137 Oaks Blvd, Winter Park, FL 32789

Showing Results 441 - 480, Page 12 of 18

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