1,137

Recently Sold Winter Park, FL Homes

Section Image
  • 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 $262,728

    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 $449,236

    Last Listing Agent Abby Vollmann COLDWELL BANKER PARADISE

    2207 Winter Woods Blvd, Winter Park, FL 32792
  • 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 $1,569,557

    Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

    817 Antonette Ave, Winter Park, FL 32789
  • 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

    Current Estimated Value $1,696,976

    Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    1181 Via Capri, Winter Park, FL 32789
  • 1436 Auburn Green Loop, Winter Park, FL 32792
    1436 Auburn Green Loop, Winter Park, FL 32792
    /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

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

    1436 Auburn Green Loop, Winter Park, FL 32792
  • 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 $1,497,447

    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 $194,196

    Last Listing Agent Arthur Love LA ROSA REALTY ORLANDO LLC

    4878 Tangerine Ave, 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

    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

    Current Estimated Value $760,702

    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 $1,256,839

    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

    Current Estimated Value $6,373,034

    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 $1,327,083

    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
  • 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 $679,082

    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 $346,822

    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 $80,876

    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 $582,302

    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 $269,654

    Last Listing Agent Jeremy Wood KELLER WILLIAMS HERITAGE REALTY

    5164 Lazy Oaks Dr, Winter Park, FL 32792
  • 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 $220,221

    Last Listing Agent Carol van den Berg VAN DEN BERG REAL ESTATE GROUP

    700 Melrose Ave Unit F2, 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 $454,303

    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

    Current Estimated Value $4,110,928

    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 $603,460

    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 $603,574

    Last Listing Agent Yousef Zeidan RE/MAX PRIME PROPERTIES

    631 Callahan St, 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 $243,427

    Last Listing Agent Michael Wood UNITED REAL ESTATE PREFERRED

    2480 Tahoe Cir, Winter Park, FL 32792
  • 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

    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 $562,082

    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 $652,417

    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 $295,199

    Last Listing Agent Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

    700 Melrose Ave Unit B4, 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

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    1875 Staunton Ave, 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 $194,702

    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 $630,839

    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 $579,112

    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 $2,919,753

    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 $702,495

    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 $2,108,527

    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 $467,687

    Last Listing Agent Leyder Salamanca FLORIDA REALTY INVESTMENTS

    1409 Hyde Park Dr, Winter Park, FL 32792

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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