1,172

Recently Sold Winter Park, FL Homes

Section Image
  • 1394 Stewart St, Winter Park, FL 32789
    1394 Stewart St, Winter Park, FL 32789
    /2

    $1,942,000 Sold Jul 14, 2025

    1394 Stewart St, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 3,907 Sq Ft
    • Built 1961

    Last Sold Summary

    • 12% Below List Price
    • $497/SF
    • 50 Days On Market

    Current Estimated Value $1,945,055

    Last Listing Agent Richard Vaughn REALTY ONE GROUP INSPIRATION

    1394 Stewart St, Winter Park, FL 32789
  • 2880 Old Castle Dr, Winter Park, FL 32792
    2880 Old Castle Dr, Winter Park, FL 32792
    /2

    $1,010,000 Sold Sep 30, 2025

    2880 Old Castle Dr, Winter Park, FL 32792

    • 5 Beds
    • 4.5 Baths
    • 3,839 Sq Ft
    • Built 1993

    Last Sold Summary

    • 10% Below List Price
    • $263/SF
    • 90 Days On Market

    Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

    2880 Old Castle Dr, Winter Park, FL 32792
  • 3324 Alena Ct, Winter Park, FL 32792
    3324 Alena Ct, Winter Park, FL 32792
    /2

    $437,000 Sold Jan 24, 2025

    3324 Alena Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,873 Sq Ft
    • Built 1971

    Last Sold Summary

    • $233/SF
    • 15 Days On Market

    Current Estimated Value $434,611

    Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

    3324 Alena Ct, Winter Park, FL 32792
  • 105 Conrad Ct, Winter Park, FL 32789
    105 Conrad Ct, Winter Park, FL 32789
    /2

    $429,999 Sold Oct 21, 2025

    105 Conrad Ct, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,573 Sq Ft
    • Built 1958

    Last Sold Summary

    • $273/SF
    • 24 Days On Market

    Last Listing Agent Pam Grabenhorst THE WILKINS WAY LLC

    105 Conrad Ct, Winter Park, FL 32789
  • 712 Baffie Ave, Winter Park, FL 32789
    712 Baffie Ave, Winter Park, FL 32789
    /2

    $292,000 Sold May 16, 2025

    712 Baffie Ave, Winter Park, FL 32789

    • 3 Beds
    • 1 Bath
    • 1,304 Sq Ft
    • Built 1925

    Last Sold Summary

    • 10% Below List Price
    • $224/SF
    • 7 Days On Market

    Current Estimated Value $310,842

    Last Listing Agent Bobby Livera BALDWIN PARK REALTY LLC

    712 Baffie Ave, Winter Park, FL 32789
  • 2337 Antilles Dr, Winter Park, FL 32792
    2337 Antilles Dr, Winter Park, FL 32792
    /2

    $249,900 Sold Mar 27, 2025

    2337 Antilles Dr, Winter Park, FL 32792

    • 2 Beds
    • 1 Bath
    • 849 Sq Ft
    • Built 1979

    Last Sold Summary

    • $294/SF
    • 20 Days On Market

    Current Estimated Value $244,720

    Last Listing Agent Diane Sterling KELLER WILLIAMS ADVANTAGE REALTY

    2337 Antilles Dr, Winter Park, FL 32792
  • 7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792
    7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792
    /2

    $100,000 Sold Sep 09, 2025

    7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft
    • Built 1974

    Last Sold Summary

    • 8% Below List Price
    • $97/SF
    • 38 Days On Market

    Current Estimated Value $102,919

    Last Listing Agent Pedro Ramos ROCKER'S REAL ESTATE, LLC

    7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792
  • 2619 Lafayette Ave, Winter Park, FL 32789
    2619 Lafayette Ave, Winter Park, FL 32789
    /2

    $1,635,000 Sold Dec 27, 2024

    2619 Lafayette Ave, Winter Park, FL 32789

    • 3 Beds
    • 4 Baths
    • 2,835 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $577/SF
    • 2 Days On Market

    Current Estimated Value $1,591,272

    Last Listing Agent Ahmad Hassan COMPASS FLORIDA LLC

    2619 Lafayette Ave, Winter Park, FL 32789
  • 1250 S Denning Dr Unit 210, Winter Park, FL 32789
    1250 S Denning Dr Unit 210, Winter Park, FL 32789
    /2

    $220,000 Sold Jan 05, 2025

    1250 S Denning Dr Unit 210, Winter Park, FL 32789

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

    Last Sold Summary

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

    Current Estimated Value $235,656

    Last Listing Agent Tina Beshara REALTY GROUP SPECIALISTS, LLC

    1250 S Denning Dr Unit 210, Winter Park, FL 32789
  • 620 Virginia Dr, Winter Park, FL 32789
    620 Virginia Dr, Winter Park, FL 32789
    /2

    $1,050,000 Sold Dec 05, 2025

    620 Virginia Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,577 Sq Ft
    • Built 1965

    Last Sold Summary

    • 6% Above List Price
    • $666/SF
    • 0 Days On Market

    Last Listing Agent Jason Gilkey GILKEY REAL ESTATE

    620 Virginia Dr, Winter Park, FL 32789
  • 1230 N Denning Dr, Winter Park, FL 32789
    1230 N Denning Dr, Winter Park, FL 32789
    /2

    $575,000 Sold May 27, 2025

    1230 N Denning Dr, Winter Park, FL 32789

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

    Last Sold Summary

    • 3% Below List Price
    • $592/SF
    • 24 Days On Market

    Current Estimated Value $561,098

    Last Listing Agent Ed Klein FANNIE HILLMAN & ASSOCIATES

    1230 N Denning Dr, Winter Park, FL 32789
  • 627 N Interlachen Ave Unit B, Winter Park, FL 32789
    627 N Interlachen Ave Unit B, Winter Park, FL 32789
    /2

    $1,005,000 Sold Feb 05, 2025

    627 N Interlachen Ave Unit B, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,610 Sq Ft
    • Built 1981

    Last Sold Summary

    • 16% Below List Price
    • $624/SF
    • 164 Days On Market

    Current Estimated Value $1,003,559

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

    627 N Interlachen Ave Unit B, Winter Park, FL 32789
  • 3053 George Mason Ave Unit 7, Winter Park, FL 32792
    3053 George Mason Ave Unit 7, Winter Park, FL 32792
    /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
  • 1000 S Semoran Blvd Unit 415, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 415, 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 $107,792

    Last Listing Agent Jhoana Loyo Urrutia LA ROSA REALTY LLC

    1000 S Semoran Blvd Unit 415, Winter Park, FL 32792
  • 130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
    130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
    /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

    Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

    130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
  • 3015 Casselwood St, Winter Park, FL 32792
    3015 Casselwood St, Winter Park, FL 32792
    /2

    $260,000 Sold Aug 07, 2025

    3015 Casselwood St, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $241/SF
    • 18 Days On Market

    Current Estimated Value $263,382

    Last Listing Agent Michelle Parrish PARRISH REALTY GROUP INC

    3015 Casselwood St, Winter Park, FL 32792
  • 2207 Winter Woods Blvd, Winter Park, FL 32792
    2207 Winter Woods Blvd, Winter Park, FL 32792
    /2

    $445,000 Sold May 23, 2025

    2207 Winter Woods Blvd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,710 Sq Ft
    • Built 1969

    Last Sold Summary

    • 7% Below List Price
    • $260/SF
    • 89 Days On Market

    Current Estimated Value $441,424

    Last Listing Agent Abby Moyer COLDWELL BANKER PARADISE

    2207 Winter Woods Blvd, Winter Park, FL 32792
  • 2112 Staunton Ave, Winter Park, FL 32789
    2112 Staunton Ave, Winter Park, FL 32789
    /2

    $449,000 Sold Jan 30, 2025

    2112 Staunton Ave, Winter Park, FL 32789

    • 3 Beds
    • 1 Bath
    • 1,438 Sq Ft
    • Built 1954

    Last Sold Summary

    • $312/SF
    • 12 Days On Market

    Current Estimated Value $449,971

    Last Listing Agent Stacey Payne PREFERRED REAL ESTATE BROKERS

    2112 Staunton Ave, Winter Park, FL 32789
  • 817 Antonette Ave, Winter Park, FL 32789
    817 Antonette Ave, 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 $1,567,703

    Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

    817 Antonette Ave, Winter Park, FL 32789
  • 335 Scottsdale Square Unit 335, Winter Park, FL 32792
    335 Scottsdale Square Unit 335, Winter Park, FL 32792
    /2

    $98,000 Sold Jan 17, 2025

    335 Scottsdale Square Unit 335, Winter Park, FL 32792

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

    Last Sold Summary

    • 22% Below List Price
    • $130/SF
    • 159 Days On Market

    Current Estimated Value $85,965

    Last Listing Agent Michel Pineda HOMERIVER GROUP

    335 Scottsdale Square Unit 335, Winter Park, FL 32792
  • 1181 Via Capri, Winter Park, FL 32789
    1181 Via Capri, Winter Park, FL 32789
    /2

    $1,550,000 Sold May 30, 2025

    1181 Via Capri, Winter Park, FL 32789

    • Land
    • 0.3 Acre
    • $5,166,667 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 42 Days On Market

    Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    1181 Via Capri, Winter Park, FL 32789
  • 1975 Staunton Ave, Winter Park, FL 32789
    1975 Staunton Ave, 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

    Last Listing Agent Marion McGrath ABSOLUTE REALTY GROUP, LLC

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

    $1,516,500 Sold Apr 24, 2025

    335 Beloit Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 2,420 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $627/SF
    • 31 Days On Market

    Current Estimated Value $1,476,670

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    335 Beloit Ave, Winter Park, FL 32789
  • 4878 Tangerine Ave, Winter Park, FL 32792
    4878 Tangerine Ave, Winter Park, FL 32792
    /2

    $192,000 Sold Jul 16, 2025

    4878 Tangerine Ave, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 1973

    Last Sold Summary

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

    Current Estimated Value $189,686

    Last Listing Agent Arthur Love LA ROSA REALTY ORLANDO LLC

    4878 Tangerine Ave, Winter Park, FL 32792
  • 218 Balfour Dr Unit 12, Winter Park, FL 32792
    218 Balfour Dr Unit 12, Winter Park, FL 32792
    /2

    $295,000 Sold Feb 07, 2025

    218 Balfour Dr Unit 12, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,256 Sq Ft
    • Built 1985

    Last Sold Summary

    • $235/SF
    • 19 Days On Market

    Current Estimated Value $299,913

    Last Listing Agent Dawn Romance FANNIE HILLMAN & ASSOCIATES

    218 Balfour Dr Unit 12, Winter Park, FL 32792
  • 2012 Loch Berry Rd, Winter Park, FL 32792
    2012 Loch Berry Rd, Winter Park, FL 32792
    /2

    $535,000 Sold May 02, 2025

    2012 Loch Berry Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft
    • Built 1956

    Last Sold Summary

    • 5% Below List Price
    • $352/SF
    • 1 Day On Market

    Current Estimated Value $541,066

    Last Listing Agent Al Sines PREMIER SOTHEBY'S INTL. REALTY

    2012 Loch Berry Rd, Winter Park, FL 32792
  • 1465 Lone Feather Trail, Winter Park, FL 32792
    1465 Lone Feather Trail, Winter Park, FL 32792
    /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

    Last Listing Agent Chris Watts THE TEAM REAL ESTATE GROUP INC

    1465 Lone Feather Trail, Winter Park, FL 32792
  • 1621 Hillcrest Ave, Winter Park, FL 32789
    1621 Hillcrest Ave, Winter Park, FL 32789
    /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 $1,254,137

    Last Listing Agent Julie Glass KEYSEEKERS REAL ESTATE

    1621 Hillcrest Ave, Winter Park, FL 32789
  • 1308 Green Cove Rd, Winter Park, FL 32789
    1308 Green Cove Rd, Winter Park, FL 32789
    /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

    Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

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

    $1,340,000 Sold May 28, 2025

    571 Lakefront Blvd, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 5,500 Sq Ft
    • Built 1967

    Last Sold Summary

    • 68% Below List Price
    • $244/SF
    • 293 Days On Market

    Current Estimated Value $1,340,403

    Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

    571 Lakefront Blvd, Winter Park, FL 32789
  • 2380 Shadowland Loop, Winter Park, FL 32792
    2380 Shadowland Loop, Winter Park, FL 32792
    /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

    Last Listing Agent Cristian Cen Chen SIMPSON REALTY LLC

    2380 Shadowland Loop, Winter Park, FL 32792
  • 141 W Lake Sue Ave, Winter Park, FL 32789
    141 W Lake Sue Ave, Winter Park, FL 32789
    /2

    $1,450,000 Sold Apr 11, 2025

    141 W Lake Sue Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,559 Sq Ft
    • Built 1951

    Last Sold Summary

    • $930/SF

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

    141 W Lake Sue Ave, Winter Park, FL 32789
  • 1821 Summerland Ave, Winter Park, FL 32789
    1821 Summerland Ave, Winter Park, FL 32789
    /2

    $3,450,000 Sold Feb 04, 2025

    1821 Summerland Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 5,097 Sq Ft
    • Built 2014

    Last Sold Summary

    • 1% Below List Price
    • $677/SF
    • 0 Days On Market

    Current Estimated Value $3,462,326

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    1821 Summerland Ave, Winter Park, FL 32789
  • 604 Darcey Dr, Winter Park, FL 32792
    604 Darcey Dr, Winter Park, FL 32792
    /2

    $675,000 Sold Apr 11, 2025

    604 Darcey Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,258 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Below List Price
    • $299/SF
    • 4 Days On Market

    Current Estimated Value $678,902

    Last Listing Agent Tiffany Grindstaff KELLY PRICE & COMPANY LLC

    604 Darcey Dr, Winter Park, FL 32792
  • 1517 Florentino Ln, Winter Park, FL 32792
    1517 Florentino Ln, Winter Park, FL 32792
    /2

    $350,000 Sold Jun 11, 2025

    1517 Florentino Ln, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Below List Price
    • $226/SF
    • 27 Days On Market

    Current Estimated Value $346,990

    Last Listing Agent Lou DiBerardino KELLER WILLIAMS WINTER PARK

    1517 Florentino Ln, Winter Park, FL 32792
  • 348 Scottsdale Square, Winter Park, FL 32792
    348 Scottsdale Square, Winter Park, FL 32792
    /2

    $80,000 Sold Jun 30, 2025

    348 Scottsdale Square, Winter Park, FL 32792

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

    Last Sold Summary

    • 27% Below List Price
    • $106/SF
    • 3 Days On Market

    Current Estimated Value $80,508

    Last Listing Agent Alan Barbosa DALTON WADE INC

    348 Scottsdale Square, Winter Park, FL 32792
  • 4353 Steed Terrace, Winter Park, FL 32792
    4353 Steed Terrace, Winter Park, FL 32792
    /2

    $575,000 Sold Jun 11, 2025

    4353 Steed Terrace, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,275 Sq Ft
    • Built 1989

    Last Sold Summary

    • $253/SF
    • 4 Days On Market

    Current Estimated Value $579,479

    Last Listing Agent Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

    4353 Steed Terrace, Winter Park, FL 32792
  • 5164 Lazy Oaks Dr, Winter Park, FL 32792
    5164 Lazy Oaks Dr, Winter Park, FL 32792
    /2

    $265,000 Sold Jul 31, 2025

    5164 Lazy Oaks Dr, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,236 Sq Ft
    • Built 1984

    Last Sold Summary

    • 5% Below List Price
    • $214/SF
    • 8 Days On Market

    Current Estimated Value $269,061

    Last Listing Agent Jeremy Wood KELLER WILLIAMS HERITAGE REALTY

    5164 Lazy Oaks Dr, Winter Park, FL 32792
  • 907 Moss Ln, Winter Park, FL 32789
    907 Moss Ln, Winter Park, FL 32789
    /2

    $1,400,000 Sold Feb 04, 2025

    907 Moss Ln, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,503 Sq Ft
    • Built 2003

    Last Sold Summary

    • 6% Below List Price
    • $559/SF
    • 8 Days On Market

    Current Estimated Value $1,387,669

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

    907 Moss Ln, Winter Park, FL 32789
  • 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

Showing Results 441 - 480, Page 12 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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