1,127

Recently Sold Winter Park, FL Homes

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    $1,688,750

    Sold Apr 01, 2026

    1705 Elizabeths Walk, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 3,820 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Above List Price
    • $442/SF
    • 3 Days On Market

    Current Estimated Value $1,701,350

    Last Listing Agent Keith Moore HOMEVEST REALTY

    1705 Elizabeths Walk, Winter Park, FL 32789
  • /2

    $895,000

    Sold Dec 29, 2025

    1802 Arbor Park Dr, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 1,808 Sq Ft
    • Built 1968

    Last Sold Summary

    • $495/SF
    • 1 Day On Market

    Current Estimated Value $979,206

    Last Listing Agent Jennifer Roberts FLORIDA EXECUTIVE REALTY

    1802 Arbor Park Dr, Winter Park, FL 32789
  • /2

    $421,000

    Sold Apr 29, 2026

    633 Lander Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1956

    Last Sold Summary

    • 1% Below List Price
    • $301/SF
    • 6 Days On Market

    Current Estimated Value $422,263

    Last Listing Agent Raymond Lopez KELLER WILLIAMS ADVANTAGE 2 REALTY

    633 Lander Rd, Winter Park, FL 32792
  • /2

    $470,000

    Sold Dec 23, 2025

    2381 Roxbury Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft
    • Built 1949

    Last Sold Summary

    • 8% Below List Price
    • $263/SF
    • 24 Days On Market

    Current Estimated Value $471,862

    Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

    2381 Roxbury Rd, 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 $1,964,805

    Last Listing Agent Richard Vaughn REALTY ONE GROUP INSPIRATION

    1394 Stewart St, Winter Park, FL 32789
  • /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

    Current Estimated Value $1,036,485

    Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

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

    $540,000

    Sold Dec 29, 2025

    1817 Jessica Ct, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,870 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Above List Price
    • $289/SF
    • 3 Days On Market

    Current Estimated Value $544,913

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1817 Jessica Ct, Winter Park, FL 32789
  • /2

    $1,450,000

    Sold Mar 19, 2026

    141 W Lake Sue Ave, Winter Park, FL 32789

    • Land
    • 22,215 Sq Ft
    • $2,843,137 per Acre

    Last Sold Summary

    • 14% Below List Price
    • 137 Days On Market

    Current Estimated Value $1,411,589

    Last Listing Agent Brian Mitnik RE/MAX 200 REALTY

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

    $1,100,000

    Sold Apr 15, 2026

    100 S Interlachen Ave Unit 404, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,220 Sq Ft
    • Built 1971

    Last Sold Summary

    • 8% Below List Price
    • $902/SF
    • 51 Days On Market

    Current Estimated Value $1,125,415

    Last Listing Agent Ruth Harris COLDWELL BANKER REALTY

    100 S Interlachen Ave Unit 404, 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

    Current Estimated Value $444,863

    Last Listing Agent Pam Grabenhorst THE WILKINS WAY LLC

    105 Conrad Ct, Winter Park, FL 32789
  • /2

    $600,000

    Sold Jan 23, 2026

    2817 Fitzooth Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,619 Sq Ft
    • Built 1965

    Last Sold Summary

    • 6% Below List Price
    • $371/SF
    • 36 Days On Market

    Current Estimated Value $591,742

    Last Listing Agent Diego Trujillo-Castillo REALTY HUB

    2817 Fitzooth Dr, 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 $106,852

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

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

    $1,300,000

    Sold Jan 02, 2026

    1400 S Pennsylvania Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,310 Sq Ft
    • Built 1962

    Last Sold Summary

    • 6% Below List Price
    • $563/SF
    • 333 Days On Market

    Current Estimated Value $1,245,007

    Last Listing Agent Jack Keller JACK KELLER INC

    1400 S Pennsylvania Ave, 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

    Current Estimated Value $1,064,806

    Last Listing Agent Jason Gilkey GILKEY REAL ESTATE

    620 Virginia Dr, Winter Park, FL 32789
  • /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 $4,590,054

    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 $111,962

    Last Listing Agent Jhoana Loyo Urrutia LA ROSA 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 $458,962

    Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

    130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
  • /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 $267,823

    Last Listing Agent Michelle Parrish PARRISH REALTY GROUP INC

    3015 Casselwood St, Winter Park, FL 32792
  • /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 $1,622,234

    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 $362,325

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

    1436 Auburn Green Loop, Winter Park, FL 32792
  • /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 $364,658

    Last Listing Agent Marion McGrath ABSOLUTE REALTY GROUP, LLC

    1975 Staunton Ave, Winter Park, FL 32789
  • /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 $3,021,130

    Last Listing Agent Lauren Richardson FANNIE HILLMAN & ASSOCIATES

    700 Pinetree Rd, Winter Park, FL 32789
  • /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 $196,874

    Last Listing Agent Arthur Love LA ROSA REALTY ORLANDO LLC

    4878 Tangerine Ave, Winter Park, FL 32792
  • /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 $376,110

    Last Listing Agent Deanna Chance A+ REALTY PROFESSIONALS, INC

    4923 N Magnolia Ave, 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 $757,861

    Last Listing Agent Chris Watts THE TEAM REAL ESTATE GROUP INC

    1465 Lone Feather Trail, 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 $1,276,414

    Last Listing Agent Julie Glass KEYSEEKERS REAL ESTATE

    1621 Hillcrest Ave, 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 $6,289,586

    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 $447,017

    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 $301,255

    Last Listing Agent Andrea Parra FANNIE HILLMAN & ASSOCIATES

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

    $455,000

    Sold Mar 03, 2026

    1221 Valley Creek Run, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,916 Sq Ft
    • Built 1994

    Last Sold Summary

    • 1% Above List Price
    • $237/SF
    • 3 Days On Market

    Current Estimated Value $454,145

    Last Listing Agent Tricia Jenkins LPT REALTY, LLC

    1221 Valley Creek Run, 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 $1,857,772

    Last Listing Agent Shanon Luiz SELECTIVE REALTY GROUP LLC

    1841 Harland Park Dr, 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 $339,616

    Last Listing Agent Emily Nickley MARKET CONNECT REALTY LLC

    2249 Minnesota Ave, Winter Park, FL 32789
  • /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 $82,142

    Last Listing Agent Alan Barbosa DALTON WADE INC

    348 Scottsdale Square, Winter Park, FL 32792
  • /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 $548,180

    Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1210 Fairway 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 $273,094

    Last Listing Agent Jeremy Wood KELLER WILLIAMS HERITAGE REALTY

    5164 Lazy Oaks 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 $474,066

    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 $199,916

    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 $4,250,043

    Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

    2161 Sharon Rd, Winter Park, FL 32789
  • /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 $475,099

    Last Listing Agent Peter Hamilton DAHLIA REALTY GROUP

    3304 Bennington Ct, Winter Park, FL 32792

Showing Results 441 - 480, Page 12 of 18

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