1,143

Recently Sold Winter Park, FL Homes

Section Image
  • 2472 Firstlight Way, Winter Park, FL 32792
    2472 Firstlight Way, Winter Park, FL 32792
    /2

    $432,000 Sold May 08, 2025

    2472 Firstlight Way, Winter Park, FL 32792

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

    Last Sold Summary

    • 8% Below List Price
    • $208/SF
    • 53 Days On Market

    Current Estimated Value $444,256

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    2472 Firstlight Way, Winter Park, FL 32792
  • 2478 Whitehall Cir, Winter Park, FL 32792
    2478 Whitehall Cir, Winter Park, FL 32792
    /2

    $605,000 Sold Dec 22, 2025

    2478 Whitehall Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,256 Sq Ft
    • Built 1965

    Last Sold Summary

    • 19% Below List Price
    • $268/SF
    • 123 Days On Market

    Last Listing Agent Erica Magtira LPT REALTY, LLC

    2478 Whitehall Cir, Winter Park, FL 32792
  • 690 Osceola Ave Unit 502, Winter Park, FL 32789
    690 Osceola Ave Unit 502, Winter Park, FL 32789
    /2

    $417,100 Sold Nov 24, 2025

    690 Osceola Ave Unit 502, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1969

    Last Sold Summary

    • 26% Below List Price
    • $298/SF
    • 196 Days On Market

    Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

    690 Osceola Ave Unit 502, Winter Park, FL 32789
  • 508 W Swoope Ave, Winter Park, FL 32789
    508 W Swoope Ave, Winter Park, FL 32789
    /2

    $1,640,000 Sold Mar 06, 2025

    508 W Swoope Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 4,133 Sq Ft
    • Built 2021

    Last Sold Summary

    • 17% Below List Price
    • $397/SF
    • 258 Days On Market

    Last Listing Agent Whitney Johnson COLDWELL BANKER RESIDENTIAL RE

    508 W Swoope Ave, Winter Park, FL 32789
  • 3505 Balsam Dr, Winter Park, FL 32792
    3505 Balsam Dr, Winter Park, FL 32792
    /2

    $380,000 Sold Feb 27, 2025

    3505 Balsam Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,709 Sq Ft
    • Built 1965

    Last Sold Summary

    • 9% Above List Price
    • $222/SF
    • 21 Days On Market

    Current Estimated Value $376,264

    Last Listing Agent Jennifer Clark GLORY INTL. REAL ESTATE CO

    3505 Balsam Dr, Winter Park, FL 32792
  • 4048 Gilder Rose Place, Winter Park, FL 32792
    4048 Gilder Rose Place, Winter Park, FL 32792
    /2

    $1,206,400 Sold Oct 15, 2025

    4048 Gilder Rose Place, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,321 Sq Ft
    • Built 1992

    Last Sold Summary

    • $363/SF
    • 101 Days On Market

    Current Estimated Value $1,196,981

    Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

    4048 Gilder Rose Place, Winter Park, FL 32792
  • 273 Scottsdale Square Unit 273, Winter Park, FL 32792
    273 Scottsdale Square Unit 273, Winter Park, FL 32792
    /2

    $72,000 Sold Jun 24, 2025

    273 Scottsdale Square Unit 273, Winter Park, FL 32792

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

    Last Sold Summary

    • 24% Below List Price
    • $92/SF
    • 4 Days On Market

    Current Estimated Value $76,258

    Last Listing Agent Erin Tompkins COLDWELL BANKER RESIDENTIAL RE

    273 Scottsdale Square Unit 273, Winter Park, FL 32792
  • 2732 Lion Heart Rd, Winter Park, FL 32792
    2732 Lion Heart Rd, Winter Park, FL 32792
    /2

    $660,000 Sold May 23, 2025

    2732 Lion Heart Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,975 Sq Ft
    • Built 1962

    Last Sold Summary

    • $334/SF
    • 2 Days On Market

    Current Estimated Value $648,191

    Last Listing Agent Sue Grafton FANNIE HILLMAN & ASSOCIATES

    2732 Lion Heart Rd, Winter Park, FL 32792
  • 1321 Medinah Ct, Winter Park, FL 32792
    1321 Medinah Ct, Winter Park, FL 32792
    /2

    $685,000 Sold May 27, 2025

    1321 Medinah Ct, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,446 Sq Ft
    • Built 1979

    Last Sold Summary

    • 9% Below List Price
    • $280/SF
    • 53 Days On Market

    Current Estimated Value $684,074

    Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

    1321 Medinah Ct, Winter Park, FL 32792
  • 595 Huntington Ave Unit 4, Winter Park, FL 32789
    595 Huntington Ave Unit 4, Winter Park, FL 32789
    /2

    $637,500 Sold Jan 16, 2026

    595 Huntington Ave Unit 4, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,951 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Below List Price
    • $327/SF
    • 149 Days On Market

    Last Listing Agent Andrew Livingston COLDWELL BANKER RESIDENTIAL RE

    595 Huntington Ave Unit 4, Winter Park, FL 32789
  • 5144 Goldenrod Place Rd, Winter Park, FL 32792
    5144 Goldenrod Place Rd, Winter Park, FL 32792
    /2

    $400,000 Sold May 29, 2025

    5144 Goldenrod Place Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Below List Price
    • $273/SF
    • 36 Days On Market

    Current Estimated Value $403,244

    Last Listing Agent Rebecca Sparks C. APOLLO REALTY INC

    5144 Goldenrod Place Rd, Winter Park, FL 32792
  • 359 Beloit Ave, Winter Park, FL 32789
    359 Beloit Ave, Winter Park, FL 32789
    /2

    $1,250,000 Sold Dec 29, 2025

    359 Beloit Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,395 Sq Ft
    • Built 1979

    Last Sold Summary

    • $522/SF
    • 0 Days On Market

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    359 Beloit Ave, Winter Park, FL 32789
  • 1026 Manchester Cir, Winter Park, FL 32792
    1026 Manchester Cir, Winter Park, FL 32792
    /2

    $468,470 Sold Jun 20, 2025

    1026 Manchester Cir, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,724 Sq Ft
    • Built 1977

    Last Sold Summary

    • 3% Below List Price
    • $272/SF
    • 25 Days On Market

    Current Estimated Value $485,328

    Last Listing Agent David Miller KELLER WILLIAMS HERITAGE REALTY

    1026 Manchester Cir, Winter Park, FL 32792
  • 1006 Bradford Dr, Winter Park, FL 32792
    1006 Bradford Dr, Winter Park, FL 32792
    /2

    $430,000 Sold Aug 08, 2025

    1006 Bradford Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,130 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Above List Price
    • $202/SF
    • 7 Days On Market

    Current Estimated Value $437,769

    Last Listing Agent Paul Giannotti TERZA REAL ESTATE

    1006 Bradford Dr, Winter Park, FL 32792
  • 1733 Harmon Ave, Winter Park, FL 32789
    1733 Harmon Ave, Winter Park, FL 32789
    /2

    $1,595,000 Sold Sep 02, 2025

    1733 Harmon Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,267 Sq Ft
    • Built 2025

    Last Sold Summary

    • $488/SF
    • 27 Days On Market

    Current Estimated Value $1,572,177

    Last Listing Agent Jordan Freeland SOUTH REALTY, INC

    1733 Harmon Ave, Winter Park, FL 32789
  • 627 Darcey Dr, Winter Park, FL 32792
    627 Darcey Dr, Winter Park, FL 32792
    /2

    $749,000 Sold Aug 13, 2025

    627 Darcey Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,509 Sq Ft
    • Built 1967

    Last Sold Summary

    • 6% Below List Price
    • $299/SF
    • 52 Days On Market

    Current Estimated Value $751,899

    Last Listing Agent Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

    627 Darcey Dr, Winter Park, FL 32792
  • 350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
    350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
    /2

    $380,000 Sold May 02, 2025

    350 Killarney Bay Ct Unit 5, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 1,428 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $266/SF
    • 42 Days On Market

    Current Estimated Value $388,807

    Last Listing Agent Dora Siler FOLIO REALTY LLC

    350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
  • 1450 Chestnut Ave, Winter Park, FL 32789
    1450 Chestnut Ave, Winter Park, FL 32789
    /2

    $1,095,000 Sold Dec 01, 2025

    1450 Chestnut Ave, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 1,942 Sq Ft
    • Built 2009

    Last Sold Summary

    • 16% Below List Price
    • $564/SF
    • 49 Days On Market

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1450 Chestnut Ave, Winter Park, FL 32789
  • 5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792
    5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792
    /2

    $260,000 Sold Feb 27, 2025

    5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1982

    Last Sold Summary

    • 5% Below List Price
    • $258/SF
    • 1 Day On Market

    Current Estimated Value $259,201

    Last Listing Agent Natalia Moege PARK 26 REALTY LLC

    5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792
  • 700 Melrose Ave Unit J23, Winter Park, FL 32789
    700 Melrose Ave Unit J23, Winter Park, FL 32789
    /2

    $220,000 Sold Jan 30, 2026

    700 Melrose Ave Unit J23, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 772 Sq Ft
    • Built 1964

    Last Sold Summary

    • 6% Below List Price
    • $285/SF
    • 107 Days On Market

    Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    700 Melrose Ave Unit J23, Winter Park, FL 32789
  • 2855 Cady Way, Winter Park, FL 32792
    2855 Cady Way, Winter Park, FL 32792
    /2

    $538,500 Sold May 16, 2025

    2855 Cady Way, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Built 1964

    Last Sold Summary

    • 9% Below List Price
    • $310/SF
    • 76 Days On Market

    Current Estimated Value $532,187

    Last Listing Agent Joe Cremonese GLOBAL PROPERTIES SALES & MGMT

    2855 Cady Way, Winter Park, FL 32792
  • 2539 Antilles Dr, Winter Park, FL 32792
    2539 Antilles Dr, Winter Park, FL 32792
    /2

    $284,000 Sold May 23, 2025

    2539 Antilles Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $249/SF
    • 50 Days On Market

    Current Estimated Value $280,034

    Last Listing Agent Allie George CORCORAN PREMIER REALTY

    2539 Antilles Dr, Winter Park, FL 32792
  • 7102 Easter St, Winter Park, FL 32792
    7102 Easter St, Winter Park, FL 32792
    /2

    $290,000 Sold Sep 22, 2025

    7102 Easter St, Winter Park, FL 32792

    • 3 Beds
    • 1 Bath
    • 1,114 Sq Ft
    • Built 1956

    Last Sold Summary

    • 3% Below List Price
    • $260/SF
    • 67 Days On Market

    Current Estimated Value $287,506

    Last Listing Agent Mayken Giraldo THE C SMITH REAL ESTATE GROUP LLC

    7102 Easter St, Winter Park, FL 32792
  • 1795 Walker Ave, Winter Park, FL 32789
    1795 Walker Ave, Winter Park, FL 32789
    /2

    $805,000 Sold Jul 01, 2025

    1795 Walker Ave, Winter Park, FL 32789

    • 5 Beds
    • 3 Baths
    • 1,813 Sq Ft
    • Built 1958

    Last Sold Summary

    • 17% Below List Price
    • $444/SF
    • 143 Days On Market

    Current Estimated Value $784,301

    Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

    1795 Walker Ave, Winter Park, FL 32789
  • 1010 Aragon Ave, Winter Park, FL 32789
    1010 Aragon Ave, Winter Park, FL 32789
    /2

    $567,500 Sold Dec 09, 2025

    1010 Aragon Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,453 Sq Ft
    • Built 1949

    Last Sold Summary

    • 1% Below List Price
    • $391/SF
    • 2 Days On Market

    Last Listing Agent Devin Loh COLDWELL BANKER RESIDENTIAL RE

    1010 Aragon Ave, Winter Park, FL 32789
  • 830 Overspin Dr, Winter Park, FL 32789
    830 Overspin Dr, Winter Park, FL 32789
    830 Overspin Dr, Winter Park, FL 32789
    /32

    $380,000 Sold Mar 07, 2025

    830 Overspin Dr, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,150 Sq Ft
    • Built 1952

    Last Sold Summary

    • 3% Below List Price
    • $330/SF
    • 30 Days On Market

    Current Estimated Value $373,916

    Last Listing Agent Richard Bavec TOLARIS REALTY GROUP LLC

    830 Overspin Dr, Winter Park, FL 32789
  • 223 Page St, Orlando, FL 32806
    223 Page St, Orlando, FL 32806
    /2

    $925,000 Sold Feb 19, 2025

    223 Page St, Orlando, FL 32806

    • 4 Beds
    • 3.5 Baths
    • 2,685 Sq Ft
    • Built 2024

    Last Sold Summary

    • 5% Below List Price
    • $345/SF
    • 143 Days On Market

    Current Estimated Value $895,515

    Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

    223 Page St, Orlando, FL 32806
  • 715 Via Bella, Winter Park, FL 32789
    715 Via Bella, Winter Park, FL 32789
    /2

    $2,078,500 Sold Dec 11, 2025

    715 Via Bella, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 4,328 Sq Ft
    • Built 1976

    Last Sold Summary

    • 12% Below List Price
    • $480/SF
    • 70 Days On Market

    Last Listing Agent Adam Roark COMPASS FLORIDA LLC

    715 Via Bella, Winter Park, FL 32789
  • 777 S Denning Dr Unit B, Winter Park, FL 32789
    777 S Denning Dr Unit B, Winter Park, FL 32789
    /2

    $602,500 Sold May 09, 2025

    777 S Denning Dr Unit B, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 1,762 Sq Ft
    • Built 2004

    Last Sold Summary

    • 6% Below List Price
    • $342/SF
    • 37 Days On Market

    Current Estimated Value $603,584

    Last Listing Agent Susan Chapin KELLER WILLIAMS WINTER PARK

    777 S Denning Dr Unit B, Winter Park, FL 32789
  • 1663 Meadowgold Ct, Winter Park, FL 32792
    1663 Meadowgold Ct, Winter Park, FL 32792
    /2

    $445,000 Sold Mar 20, 2025

    1663 Meadowgold Ct, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,851 Sq Ft
    • Built 1987

    Last Sold Summary

    • 11% Below List Price
    • $240/SF
    • 173 Days On Market

    Current Estimated Value $446,346

    Last Listing Agent Dallas Wittish ORLANDO REALTY & PROPERTY MGNT

    1663 Meadowgold Ct, Winter Park, FL 32792
  • 1122 Washington Ave Unit 7, Winter Park, FL 32789
    1122 Washington Ave Unit 7, Winter Park, FL 32789
    /2

    $434,000 Sold Sep 12, 2025

    1122 Washington Ave Unit 7, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 1,556 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Above List Price
    • $279/SF
    • 55 Days On Market

    Current Estimated Value $443,572

    Last Listing Agent Raul Veitia BELMONT REALTY

    1122 Washington Ave Unit 7, Winter Park, FL 32789
  • 715 Roughbeard Rd, Winter Park, FL 32792
    715 Roughbeard Rd, Winter Park, FL 32792
    /2

    $505,000 Sold Aug 01, 2025

    715 Roughbeard Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,250 Sq Ft
    • Built 1968

    Last Sold Summary

    • 12% Below List Price
    • $224/SF
    • 60 Days On Market

    Current Estimated Value $528,542

    Last Listing Agent Christine Gerardi NEXTHOME DIAMOND PROPERTIES

    715 Roughbeard Rd, Winter Park, FL 32792
  • 2309 Sun Valley Cir, Winter Park, FL 32792
    2309 Sun Valley Cir, Winter Park, FL 32792
    /2

    $252,500 Sold Jul 17, 2025

    2309 Sun Valley Cir, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,669 Sq Ft
    • Built 1985

    Last Sold Summary

    • 11% Below List Price
    • $151/SF
    • 65 Days On Market

    Current Estimated Value $257,987

    Last Listing Agent Kristin Vogt CENTURY 21 INTEGRA

    2309 Sun Valley Cir, Winter Park, FL 32792
  • 3455 Athena Dr, Winter Park, FL 32792
    3455 Athena Dr, Winter Park, FL 32792
    /2

    $458,000 Sold Feb 25, 2025

    3455 Athena Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,161 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $212/SF
    • 135 Days On Market

    Current Estimated Value $471,905

    Last Listing Agent Stephanie Kovats KELLER WILLIAMS ADVANTAGE REALTY

    3455 Athena Dr, Winter Park, FL 32792
  • 1037 Fairway Dr, Winter Park, FL 32792
    1037 Fairway Dr, Winter Park, FL 32792
    /2

    $660,000 Sold Apr 14, 2025

    1037 Fairway Dr, Winter Park, FL 32792

    • 3 Beds
    • 3 Baths
    • 2,145 Sq Ft
    • Built 1978

    Last Sold Summary

    • 6% Below List Price
    • $308/SF
    • 29 Days On Market

    Current Estimated Value $656,994

    Last Listing Agent Skip Juma LEGACY REALTY & BROKERS LLC

    1037 Fairway Dr, Winter Park, FL 32792
  • 443 Lakewood Dr, Winter Park, FL 32789
    443 Lakewood Dr, Winter Park, FL 32789
    /2

    $3,550,000 Sold Mar 24, 2025

    443 Lakewood Dr, Winter Park, FL 32789

    • 3 Beds
    • 5 Baths
    • 2,803 Sq Ft
    • Built 1954

    Last Sold Summary

    • 1% Above List Price
    • $1,267/SF
    • 0 Days On Market

    Current Estimated Value $3,313,312

    Last Listing Agent Jenny Lake FANNIE HILLMAN & ASSOCIATES

    443 Lakewood Dr, Winter Park, FL 32789
  • 541 London Rd, Winter Park, FL 32792
    541 London Rd, Winter Park, FL 32792
    /2

    $468,000 Sold Aug 28, 2025

    541 London Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,899 Sq Ft
    • Built 1965

    Last Sold Summary

    • $246/SF
    • 8 Days On Market

    Current Estimated Value $473,728

    Last Listing Agent Christopher Bauman REVEL REALTY LLC

    541 London Rd, Winter Park, FL 32792
  • 350 Carolina Ave Unit 301, Winter Park, FL 32789
    350 Carolina Ave Unit 301, Winter Park, FL 32789
    350 Carolina Ave Unit 301, Winter Park, FL 32789
    /51

    $704,700 Sold Mar 11, 2025

    350 Carolina Ave Unit 301, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • $456/SF
    • 26 Days On Market

    Current Estimated Value $710,123

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    350 Carolina Ave Unit 301, Winter Park, FL 32789
  • 7706 Waunatta Ct, Winter Park, FL 32792
    7706 Waunatta Ct, Winter Park, FL 32792
    /2

    $935,000 Sold Dec 19, 2025

    7706 Waunatta Ct, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 3,858 Sq Ft
    • Built 1978

    Last Sold Summary

    • 11% Below List Price
    • $242/SF
    • 70 Days On Market

    Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

    7706 Waunatta Ct, Winter Park, FL 32792
  • 233 Hampden Place, Winter Park, FL 32789
    233 Hampden Place, Winter Park, FL 32789
    /2

    $1,110,000 Sold Aug 26, 2025

    233 Hampden Place, Winter Park, FL 32789

    • 5 Beds
    • 3 Baths
    • 2,813 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Below List Price
    • $395/SF
    • 7 Days On Market

    Current Estimated Value $1,154,160

    Last Listing Agent Frank Ferrell FERRELL REALTY, INC.

    233 Hampden Place, Winter Park, FL 32789

Showing Results 121 - 160, Page 4 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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