1,127

Recently Sold Winter Park, FL Homes

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  • 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

    Current Estimated Value $428,343

    Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

    690 Osceola Ave Unit 502, Winter Park, FL 32789
  • 950 Aragon Ave, Winter Park, FL 32789
    950 Aragon Ave, Winter Park, FL 32789
    /2

    $1,200,000 Sold Mar 20, 2026

    950 Aragon Ave, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,592 Sq Ft
    • Built 2020

    Last Sold Summary

    • $463/SF
    • 5 Days On Market

    Current Estimated Value $1,006,236

    Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

    950 Aragon Ave, Winter Park, FL 32789
  • 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 $1,183,591

    Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

    4048 Gilder Rose Place, Winter Park, FL 32792
  • 275 N Ranger Blvd, Winter Park, FL 32792
    275 N Ranger Blvd, Winter Park, FL 32792
    /2

    $487,500 Sold Mar 26, 2026

    275 N Ranger Blvd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,864 Sq Ft
    • Built 1965

    Last Sold Summary

    • 2% Below List Price
    • $262/SF
    • 2 Days On Market

    Current Estimated Value $542,268

    Last Listing Agent David Augello ON POINT REALTY LLC

    275 N Ranger Blvd, 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 $75,230

    Last Listing Agent Erin Tompkins COLDWELL BANKER REALTY

    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 $649,458

    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 $693,792

    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

    Current Estimated Value $637,523

    Last Listing Agent Andrew Livingston COLDWELL BANKER REALTY

    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 $398,228

    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

    Current Estimated Value $1,248,370

    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 $467,385

    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 $435,208

    Last Listing Agent Paul Giannotti TERZA REAL ESTATE

    1006 Bradford Dr, Winter Park, FL 32792
  • 1670 Clematis Ln, Winter Park, FL 32792
    1670 Clematis Ln, Winter Park, FL 32792
    /2

    $390,000 Sold Feb 23, 2026

    1670 Clematis Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,401 Sq Ft
    • Built 1962

    Last Sold Summary

    • 11% Below List Price
    • $278/SF
    • 81 Days On Market

    Current Estimated Value $379,231

    Last Listing Agent Gea Gomez LPT REALTY, LLC

    1670 Clematis Ln, 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 $1,576,017

    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 $748,728

    Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

    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 $378,517

    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

    Current Estimated Value $1,080,985

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1450 Chestnut Ave, Winter Park, FL 32789
  • 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

    Current Estimated Value $214,548

    Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    700 Melrose Ave Unit J23, Winter Park, FL 32789
  • 2833 Prince John Rd, Winter Park, FL 32792
    2833 Prince John Rd, Winter Park, FL 32792
    /2

    $400,000 Sold Feb 13, 2026

    2833 Prince John Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,605 Sq Ft
    • Built 1963

    Last Sold Summary

    • 7% Below List Price
    • $249/SF
    • 9 Days On Market

    Current Estimated Value $452,077

    Last Listing Agent Makena Clark EXIT REALTY PREMIER LEGACY

    2833 Prince John Rd, Winter Park, FL 32792
  • 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 $536,032

    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 $278,476

    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 $292,847

    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 $794,536

    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

    Current Estimated Value $562,085

    Last Listing Agent Devin Loh COLDWELL BANKER REALTY

    1010 Aragon Ave, Winter Park, FL 32789
  • 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

    Current Estimated Value $2,115,882

    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 $582,504

    Last Listing Agent Susan Chapin KELLER WILLIAMS WINTER PARK

    777 S Denning Dr Unit B, Winter Park, FL 32789
  • 2009 Cornell Ave, Winter Park, FL 32789
    2009 Cornell Ave, Winter Park, FL 32789
    /2

    $250,000 Sold Mar 11, 2026

    2009 Cornell Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 762 Sq Ft
    • Built 1940

    Last Sold Summary

    • 7% Below List Price
    • $328/SF
    • 95 Days On Market

    Current Estimated Value $255,156

    Last Listing Agent Juliet Saldarriaga ORLANDO HOME DEALER LLC

    2009 Cornell Ave, Winter Park, FL 32789
  • 1007 Early Ave, Winter Park, FL 32789
    1007 Early Ave, Winter Park, FL 32789
    /2

    $375,000 Sold Mar 06, 2026

    1007 Early Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,721 Sq Ft
    • Built 1956

    Last Sold Summary

    • 12% Below List Price
    • $218/SF
    • 101 Days On Market

    Current Estimated Value $380,832

    Last Listing Agent Eric Gross EXP REALTY LLC

    1007 Early Ave, Winter Park, FL 32789
  • 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 $436,413

    Last Listing Agent Raul Veitia BELMONT REALTY

    1122 Washington Ave Unit 7, Winter Park, FL 32789
  • 465 N Phelps Ave, Winter Park, FL 32789
    465 N Phelps Ave, Winter Park, FL 32789
    /2

    $850,000 Sold Mar 25, 2026

    465 N Phelps Ave, Winter Park, FL 32789

    • Land
    • 0.27 Acre
    • $3,148,148 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $1,017,024

    Last Listing Agent Hircanys Vicioso FIDICITY REALTY INC

    465 N Phelps Ave, 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 $528,592

    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 $251,455

    Last Listing Agent Kristin Vogt PLLC KGV REALTY GROUP

    2309 Sun Valley Cir, 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 $661,924

    Last Listing Agent Skip Juma LEGACY REALTY & BROKERS LLC

    1037 Fairway Dr, Winter Park, FL 32792
  • 609 Gallery Dr Unit 204, Winter Park, FL 32792
    609 Gallery Dr Unit 204, Winter Park, FL 32792
    /2

    $268,000 Sold Feb 24, 2026

    609 Gallery Dr Unit 204, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 893 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Below List Price
    • $300/SF
    • 99 Days On Market

    Current Estimated Value $262,269

    Last Listing Agent Olga Ray A2Z REALTY GROUP

    609 Gallery Dr Unit 204, Winter Park, FL 32792
  • 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 $484,546

    Last Listing Agent Christopher Bauman REVEL REALTY LLC

    541 London Rd, Winter Park, FL 32792
  • 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

    Current Estimated Value $965,003

    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 $1,187,533

    Last Listing Agent Frank Ferrell FERRELL REALTY, INC.

    233 Hampden Place, Winter Park, FL 32789
  • 3251 Oak Lake Place Unit 135, Winter Park, FL 32792
    3251 Oak Lake Place Unit 135, Winter Park, FL 32792
    /2

    $200,000 Sold Sep 13, 2025

    3251 Oak Lake Place Unit 135, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft
    • Built 1984

    Last Sold Summary

    • 11% Below List Price
    • $174/SF
    • 131 Days On Market

    Current Estimated Value $193,170

    Last Listing Agent Nick Nesta, III NESTA REAL ESTATE CONSULTANTS

    3251 Oak Lake Place Unit 135, Winter Park, FL 32792
  • 1900 W Fawsett Rd, Winter Park, FL 32789
    1900 W Fawsett Rd, Winter Park, FL 32789
    /2

    $3,200,000 Sold Nov 04, 2025

    1900 W Fawsett Rd, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 4,600 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $696/SF
    • 6 Days On Market

    Current Estimated Value $3,178,851

    Last Listing Agent Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

    1900 W Fawsett Rd, Winter Park, FL 32789
  • 2248 Middleton Ave, Winter Park, FL 32792
    2248 Middleton Ave, Winter Park, FL 32792
    /2

    $1,850,000 Sold Apr 07, 2025

    2248 Middleton Ave, Winter Park, FL 32792

    • 4 Beds
    • 4.5 Baths
    • 3,505 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $528/SF
    • 10 Days On Market

    Current Estimated Value $1,550,705

    Last Listing Agent Karen Jacobs COLDWELL BANKER REALTY

    2248 Middleton Ave, Winter Park, FL 32792

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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