1,127

Recently Sold Winter Park, FL Homes

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  • /2

    $655,000

    Sold Sep 12, 2025

    1640 Cypress Point Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft
    • Built 1980

    Last Sold Summary

    • 8% Below List Price
    • $384/SF
    • 23 Days On Market

    Current Estimated Value $655,637

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    1640 Cypress Point Ln, Winter Park, FL 32792
  • /2

    $428,000

    Sold Jul 02, 2025

    3520 Balsam Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,468 Sq Ft
    • Built 1965

    Last Sold Summary

    • 1% Above List Price
    • $292/SF
    • 22 Days On Market

    Current Estimated Value $425,415

    Last Listing Agent Cece Wong EXP REALTY LLC

    3520 Balsam Dr, Winter Park, FL 32792
  • /2

    $700,000

    Sold Feb 26, 2026

    2002 Karolina Ave, Winter Park, FL 32789

    • Land
    • 19,602 Sq Ft
    • $1,555,556 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 68 Days On Market

    Current Estimated Value $626,772

    Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    2002 Karolina Ave, Winter Park, FL 32789
  • /2

    $7,164,000

    Sold May 15, 2026

    1821 Pinetree Rd, Winter Park, FL 32789

    • 5 Beds
    • 6.5 Baths
    • 5,006 Sq Ft
    • Built 2018

    Last Sold Summary

    • 2% Above List Price
    • $1,431/SF
    • 5 Days On Market

    Current Estimated Value $6,627,754

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    1821 Pinetree Rd, Winter Park, FL 32789
  • /2

    $135,000

    Sold Jun 17, 2026

    144 Lewfield Cir, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 678 Sq Ft
    • Built 1973

    Last Sold Summary

    • 9% Below List Price
    • $199/SF
    • 67 Days On Market

    Current Estimated Value $143,902

    Last Listing Agent Sandra Da Silva KELLER WILLIAMS HERITAGE REALTY

    144 Lewfield Cir, Winter Park, FL 32792
  • /2

    $510,000

    Sold Aug 29, 2025

    2739 Amsden Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,877 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Above List Price
    • $272/SF
    • 6 Days On Market

    Current Estimated Value $503,366

    Last Listing Agent D'Anne Mica ARROWSMITH REALTY, INC

    2739 Amsden Rd, Winter Park, FL 32792
  • /2

    $470,000

    Sold Aug 18, 2025

    4026 Tenita Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,122 Sq Ft
    • Built 1979

    Last Sold Summary

    • 16% Below List Price
    • $221/SF
    • 226 Days On Market

    Current Estimated Value $488,111

    Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

    4026 Tenita Dr, Winter Park, FL 32792
  • /2

    $655,000

    Sold Dec 03, 2025

    2825 Mulford Ave, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,249 Sq Ft
    • Built 1952

    Last Sold Summary

    • 6% Below List Price
    • $524/SF
    • 50 Days On Market

    Current Estimated Value $653,900

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    2825 Mulford Ave, Winter Park, FL 32789
  • /2

    $272,500

    Sold Aug 26, 2025

    2358 Sun Valley Cir, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,295 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $210/SF
    • 24 Days On Market

    Current Estimated Value $271,195

    Last Listing Agent Natalie Kauffman KELLER WILLIAMS CLASSIC

    2358 Sun Valley Cir, Winter Park, FL 32792
  • /2

    $610,000

    Sold Jun 01, 2026

    1489 Aster Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,227 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $274/SF
    • 144 Days On Market

    Current Estimated Value $634,155

    Last Listing Agent Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

    1489 Aster Ct, Winter Park, FL 32792
  • /2

    $1,175,000

    Sold Jul 08, 2025

    835 Antonette Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,867 Sq Ft
    • Built 1925

    Last Sold Summary

    • 2% Below List Price
    • $629/SF
    • 7 Days On Market

    Current Estimated Value $1,160,022

    Last Listing Agent Alexis Davis FANNIE HILLMAN & ASSOCIATES

    835 Antonette Ave, Winter Park, FL 32789
  • /2

    $300,000

    Sold Feb 20, 2026

    600 W Webster Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 754 Sq Ft
    • Built 1950

    Last Sold Summary

    • 2% Above List Price
    • $398/SF
    • 5 Days On Market

    Current Estimated Value $298,806

    Last Listing Agent Nicholas Cadwallader REALTY ONE GROUP MVP

    600 W Webster Ave, Winter Park, FL 32789
  • /2

    $1,422,750

    Sold Oct 21, 2025

    8041 Lake Waunatta Dr, Winter Park, FL 32792

    • 5 Beds
    • 4.5 Baths
    • 5,329 Sq Ft
    • Built 1984

    Last Sold Summary

    • 16% Below List Price
    • $267/SF
    • 170 Days On Market

    Current Estimated Value $1,452,123

    Last Listing Agent Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

    8041 Lake Waunatta Dr, Winter Park, FL 32792
  • /2

    $985,000

    Sold Jun 05, 2026

    1453 Via Sangro Place, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 3,057 Sq Ft
    • Built 2015

    Last Sold Summary

    • 1% Below List Price
    • $322/SF
    • 3 Days On Market

    Current Estimated Value $987,103

    Last Listing Agent Brian Diaz KELLER WILLIAMS ADVANTAGE REALTY

    1453 Via Sangro Place, Winter Park, FL 32792
  • /2

    $845,000

    Sold Jun 12, 2026

    2208 Howard Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 2,155 Sq Ft
    • Built 1957

    Last Sold Summary

    • $392/SF
    • 0 Days On Market

    Current Estimated Value $776,984

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

    2208 Howard Dr, Winter Park, FL 32789
  • /2

    $1,050,000

    Sold Jul 07, 2025

    2923 Cove Trail, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,377 Sq Ft
    • Built 1964

    Last Sold Summary

    • 2% Above List Price
    • $311/SF
    • 9 Days On Market

    Current Estimated Value $1,111,174

    Last Listing Agent Robin Delaney KELLER WILLIAMS ADVANTAGE III

    2923 Cove Trail, Winter Park, FL 32789
  • /2

    $719,000

    Sold Nov 19, 2025

    7895 Pleasant Pine Cir, Winter Park, FL 32792

    • 5 Beds
    • 3.5 Baths
    • 3,568 Sq Ft
    • Built 2014

    Last Sold Summary

    • 2% Below List Price
    • $202/SF
    • 115 Days On Market

    Current Estimated Value $735,889

    Last Listing Agent Yvette Hoover ALL REAL ESTATE & INVESTMENTS

    7895 Pleasant Pine Cir, Winter Park, FL 32792
  • /2

    $705,000

    Sold Jul 21, 2025

    1730 Oneco Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1967

    Last Sold Summary

    • 8% Above List Price
    • $501/SF
    • 2 Days On Market

    Current Estimated Value $746,587

    Last Listing Agent John Tremblay THE TEAM REAL ESTATE GROUP INC

    1730 Oneco Ave, Winter Park, FL 32789
  • /2

    $278,250

    Sold Dec 15, 2025

    1509 Sugarwood Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,706 Sq Ft
    • Built 1983

    Last Sold Summary

    • 47% Above List Price
    • $163/SF
    • 38 Days On Market

    Current Estimated Value $285,333

    Last Listing Agent Heather Unger, PA ACME REAL ESTATE FLORIDA LLC

    1509 Sugarwood Cir, Winter Park, FL 32792
  • /2

    $765,000

    Sold Nov 21, 2025

    441 N Capen Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,745 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Below List Price
    • $438/SF
    • 183 Days On Market

    Current Estimated Value $787,389

    Last Listing Agent Susan Taliaferro COLDWELL BANKER REALTY

    441 N Capen Ave, Winter Park, FL 32789
  • /2

    $440,000

    Sold Mar 27, 2026

    1028 Princess Gate Blvd, Winter Park, FL 32792

    • 5 Beds
    • 2 Baths
    • 2,044 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $215/SF
    • 46 Days On Market

    Current Estimated Value $438,324

    Last Listing Agent Jose Hernandez LA ROSA REALTY CW PROPERTIES L

    1028 Princess Gate Blvd, Winter Park, FL 32792
  • /2

    $195,000

    Sold Oct 17, 2025

    3220 Netherwood Dr, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft
    • Built 1982

    Last Sold Summary

    • 13% Below List Price
    • $188/SF
    • 87 Days On Market

    Current Estimated Value $260,978

    Last Listing Agent Nimrah Ashraf THE FIRM RE

    3220 Netherwood Dr, Winter Park, FL 32792
  • /2

    $1,700,000

    Sold May 07, 2026

    633 Balmoral Rd, Winter Park, FL 32789

    • Land
    • 23,086 Sq Ft
    • $3,207,547 per Acre

    Last Sold Summary

    • 13% Below List Price
    • 152 Days On Market

    Current Estimated Value $1,737,982

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

    633 Balmoral Rd, Winter Park, FL 32789
  • /2

    $370,000

    Sold Mar 24, 2026

    1448 E Brookshire Ct, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,518 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Below List Price
    • $244/SF
    • 28 Days On Market

    Current Estimated Value $371,989

    Last Listing Agent Antoine Divay FCG REALTY

    1448 E Brookshire Ct, Winter Park, FL 32792
  • /2

    $5,250,000

    Sold Oct 06, 2025

    1155 Woodmere Dr, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 5,051 Sq Ft
    • Built 2003

    Last Sold Summary

    • 1% Below List Price
    • $1,039/SF
    • 0 Days On Market

    Current Estimated Value $4,986,782

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

    1155 Woodmere Dr, Winter Park, FL 32789
  • /2

    $630,000

    Sold Jun 15, 2026

    3018 Northwood Blvd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,761 Sq Ft
    • Built 1954

    Last Sold Summary

    • 16% Below List Price
    • $358/SF
    • 216 Days On Market

    Current Estimated Value $670,548

    Last Listing Agent Joel Bornstein ROCK SPRINGS REALTY, LLC

    3018 Northwood Blvd, Winter Park, FL 32789
  • /2

    $185,000

    Sold Aug 05, 2025

    200 St Andrews Blvd Unit 802, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 987 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Below List Price
    • $187/SF
    • 7 Days On Market

    Current Estimated Value $190,428

    Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

    200 St Andrews Blvd Unit 802, Winter Park, FL 32792
  • /2

    $218,000

    Sold Jun 10, 2026

    7117 Swallow Run Unit G-1, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,565 Sq Ft
    • Built 2011

    Last Sold Summary

    • 15% Below List Price
    • $139/SF
    • 93 Days On Market

    Current Estimated Value $242,811

    Last Listing Agent Greg Traub COMPLETE FLORIDA REALTY LLC

    7117 Swallow Run Unit G-1, Winter Park, FL 32792
  • /2

    $1,005,000

    Sold Apr 01, 2026

    244 Osceola Ct, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 1,837 Sq Ft
    • Built 1940

    Last Sold Summary

    • 23% Below List Price
    • $547/SF
    • 41 Days On Market

    Current Estimated Value $1,018,105

    Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    244 Osceola Ct, Winter Park, FL 32789
  • /2

    $1,275,000

    Sold Jul 08, 2025

    2536 Brookshire Ave, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,140 Sq Ft
    • Built 2018

    Last Sold Summary

    • 9% Below List Price
    • $406/SF
    • 83 Days On Market

    Current Estimated Value $1,266,339

    Last Listing Agent Richard Palmano PALMANO GROUP RE BROKERAGE LLC

    2536 Brookshire Ave, Winter Park, FL 32792
  • /2

    $515,000

    Sold Oct 06, 2025

    101 S Ranger Blvd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1963

    Last Sold Summary

    • $322/SF
    • 2 Days On Market

    Current Estimated Value $503,868

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    101 S Ranger Blvd, Winter Park, FL 32792
  • /2

    $475,000

    Sold Feb 06, 2026

    2042 Yorkshire Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,573 Sq Ft
    • Built 1961

    Last Sold Summary

    • 5% Below List Price
    • $302/SF
    • 32 Days On Market

    Current Estimated Value $475,530

    Last Listing Agent Steven Ritz KELLER WILLIAMS WINTER PARK

    2042 Yorkshire Dr, Winter Park, FL 32792
  • /2

    $625,000

    Sold Nov 03, 2025

    7888 Pleasant Pine Cir, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,267 Sq Ft
    • Built 2016

    Last Sold Summary

    • $276/SF
    • 7 Days On Market

    Current Estimated Value $625,161

    Last Listing Agent Todd Schroth EXP REALTY LLC

    7888 Pleasant Pine Cir, Winter Park, FL 32792
  • /2

    $260,000

    Sold Jan 20, 2026

    2489 Tahoe Cir Unit 2489, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $198/SF
    • 87 Days On Market

    Current Estimated Value $261,181

    Last Listing Agent Kim James CHARLES RUTENBERG REALTY ORLANDO

    2489 Tahoe Cir Unit 2489, Winter Park, FL 32792
  • /2

    $600,000

    Sold Aug 05, 2025

    2244 Brookshire Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft
    • Built 1958

    Last Sold Summary

    • 9% Above List Price
    • $410/SF
    • 26 Days On Market

    Current Estimated Value $579,657

    Last Listing Agent Melissa Johnson EXP REALTY LLC

    2244 Brookshire Ave, Winter Park, FL 32792
  • /2

    $1,201,000

    Sold Jun 18, 2026

    1723 Chestnut Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,608 Sq Ft
    • Built 1962

    Last Sold Summary

    • 7% Above List Price
    • $461/SF
    • 1 Day On Market

    Current Estimated Value $1,129,430

    Last Listing Agent Anne Rogers ANNE ROGERS REALTY GROUP INC

    1723 Chestnut Ave, Winter Park, FL 32789
  • /2

    $420,000

    Sold Jun 11, 2026

    1611 Little Wren Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft
    • Built 2020

    Last Sold Summary

    • 1% Above List Price
    • $239/SF
    • 3 Days On Market

    Current Estimated Value $447,882

    Last Listing Agent Chris Winn BLOOM HOME GROUP REALTY LLC

    1611 Little Wren Ln, Winter Park, FL 32792
  • /2

    $630,000

    Sold Oct 03, 2025

    1015 Bungalow Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • Built 2012

    Last Sold Summary

    • $377/SF
    • 2 Days On Market

    Current Estimated Value $708,847

    Last Listing Agent David Francetic COLDWELL BANKER REALTY

    1015 Bungalow Ave, Winter Park, FL 32789
  • /2

    $455,500

    Sold Oct 16, 2025

    1317 Medinah Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,015 Sq Ft
    • Built 1979

    Last Sold Summary

    • 9% Below List Price
    • $226/SF

    Current Estimated Value $736,636

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    1317 Medinah Ct, Winter Park, FL 32792
  • /2

    $389,000

    Sold Dec 30, 2025

    3383 Hamlet Loop, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,201 Sq Ft
    • Built 1994

    Last Sold Summary

    • $324/SF
    • 10 Days On Market

    Current Estimated Value $383,860

    Last Listing Agent Jason Asa LPT REALTY, LLC

    3383 Hamlet Loop, Winter Park, FL 32792

Showing Results 561 - 600, Page 15 of 18

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