1,105

Recently Sold Winter Park, FL Homes

Section Image Section Image
  • /2

    $325,000

    Sold Dec 30, 2025

    520 Killarney Bay Ct Unit 2, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft
    • Built 1986

    Last Sold Summary

    • 7% Below List Price
    • $280/SF
    • 6 Days On Market

    Current Estimated Value $321,938

    Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

    520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
  • /2

    $517,000

    Sold Nov 07, 2025

    1628 Lawndale Cir, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,716 Sq Ft
    • Built 1984

    Last Sold Summary

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

    Current Estimated Value $517,519

    Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

    1628 Lawndale Cir, Winter Park, FL 32792
  • /2

    $2,000,000

    Sold May 11, 2026

    2820 Bear Island Pointe, Winter Park, FL 32792

    • 3 Beds
    • 4.5 Baths
    • 5,138 Sq Ft
    • Built 1998

    Last Sold Summary

    • 5% Below List Price
    • $389/SF
    • 6 Days On Market

    Current Estimated Value $1,987,784

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    2820 Bear Island Pointe, Winter Park, FL 32792
  • /2

    $351,000

    Sold Sep 09, 2025

    1041 Manchester Cir, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • Built 1977

    Last Sold Summary

    • 16% Below List Price
    • $209/SF
    • 147 Days On Market

    Current Estimated Value $386,744

    Last Listing Agent Bob Paulson COLDWELL BANKER REALTY

    1041 Manchester Cir, Winter Park, FL 32792
  • /2

    $720,000

    Sold Jan 20, 2026

    2955 Lolissa Ln, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 3,538 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $204/SF
    • 47 Days On Market

    Current Estimated Value $784,995

    Last Listing Agent Catherine Williams COLDWELL BANKER REALTY

    2955 Lolissa Ln, Winter Park, FL 32789
  • /2

    $2,285,000

    Sold Nov 19, 2025

    521 S Phelps Ave, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,883 Sq Ft
    • Built 2015

    Last Sold Summary

    • 7% Below List Price
    • $588/SF
    • 118 Days On Market

    Current Estimated Value $2,398,900

    Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

    521 S Phelps Ave, Winter Park, FL 32789
  • /2

    $350,000

    Sold May 22, 2026

    989 Eastbrook Blvd, Winter Park, FL 32792

    • 3 Beds
    • 1.5 Baths
    • 1,140 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Below List Price
    • $307/SF
    • 35 Days On Market

    Current Estimated Value $346,077

    Last Listing Agent Jane Pedigree COLDWELL BANKER REALTY

    989 Eastbrook Blvd, Winter Park, FL 32792
  • /2

    $450,000

    Sold Aug 28, 2025

    2151 Conifer Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,806 Sq Ft
    • Built 1970

    Last Sold Summary

    • 2% Below List Price
    • $249/SF
    • 32 Days On Market

    Current Estimated Value $461,821

    Last Listing Agent Denise Korrey KORR REALTY CORP

    2151 Conifer Ave, Winter Park, FL 32792
  • /2

    $290,000

    Sold Nov 24, 2025

    2411 Gallery View Dr Unit 5, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,004 Sq Ft
    • Built 1985

    Last Sold Summary

    • 9% Below List Price
    • $289/SF
    • 54 Days On Market

    Current Estimated Value $298,424

    Last Listing Agent Maria Elena Perez MEP REALTY INVESTMENTS LLC

    2411 Gallery View Dr Unit 5, Winter Park, FL 32792
  • /2

    $180,000

    Sold Feb 27, 2026

    200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792

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

    Last Sold Summary

    • 8% Below List Price
    • $182/SF
    • 11 Days On Market

    Current Estimated Value $184,713

    Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

    200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
  • /2

    $115,000

    Sold May 08, 2026

    1000 S Semoran Blvd Unit 512, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,072 Sq Ft
    • Built 1969

    Last Sold Summary

    • 11% Below List Price
    • $107/SF
    • 41 Days On Market

    Current Estimated Value $120,573

    Last Listing Agent Cristina Burgos REALSOURCE PROPERTY MANGNT LLC

    1000 S Semoran Blvd Unit 512, Winter Park, FL 32792
  • /2

    $4,772,500

    Sold Sep 18, 2025

    765 Via Lugano, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 4,319 Sq Ft
    • Built 2019

    Last Sold Summary

    • $1,105/SF
    • 1 Day On Market

    Current Estimated Value $4,888,049

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

    765 Via Lugano, Winter Park, FL 32789
  • /2

    $2,700,000

    Sold Oct 02, 2025

    1445 Holts Grove Cir, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 4,489 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Above List Price
    • $601/SF
    • 2 Days On Market

    Current Estimated Value $2,761,734

    Last Listing Agent Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

    1445 Holts Grove Cir, Winter Park, FL 32789
  • /2

    $375,000

    Sold Dec 30, 2025

    3083 Crane Strand Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1972

    Last Sold Summary

    • $312/SF
    • 12 Days On Market

    Current Estimated Value $385,394

    Last Listing Agent Sheri Malin REDFIN CORPORATION

    3083 Crane Strand Dr, Winter Park, FL 32792
  • /2

    $560,000

    Sold Aug 20, 2025

    1901 Loch Berry Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft
    • Built 1957

    Last Sold Summary

    • 1% Below List Price
    • $394/SF
    • 7 Days On Market

    Current Estimated Value $560,009

    Last Listing Agent Monica Tipirneni FOLIO REALTY LLC

    1901 Loch Berry Rd, Winter Park, FL 32792
  • /2

    $660,000

    Sold Nov 17, 2025

    2421 Summerfield Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,256 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Above List Price
    • $293/SF
    • 6 Days On Market

    Current Estimated Value $676,054

    Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

    2421 Summerfield Rd, Winter Park, FL 32792
  • /2

    $610,000

    Sold Jun 12, 2026

    1174 Wildmeadow Run, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft
    • Built 2021

    Last Sold Summary

    • 9% Below List Price
    • $345/SF
    • 54 Days On Market

    Current Estimated Value $615,213

    Last Listing Agent Kara Lushear COLDWELL BANKER REALTY

    1174 Wildmeadow Run, Winter Park, FL 32792
  • /2

    $3,485,000

    Sold Oct 17, 2025

    2171 Forrest Rd, Winter Park, FL 32789

    • 5 Beds
    • 6 Baths
    • 4,565 Sq Ft
    • Built 2016

    Last Sold Summary

    • 9% Below List Price
    • $763/SF
    • 134 Days On Market

    Current Estimated Value $3,521,934

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

    2171 Forrest Rd, Winter Park, FL 32789
  • /2

    $970,000

    Sold Aug 12, 2025

    207 E Kings Way, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,570 Sq Ft
    • Built 1951

    Last Sold Summary

    • $618/SF
    • 0 Days On Market

    Current Estimated Value $1,482,253

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    207 E Kings Way, Winter Park, FL 32789
  • /2

    $390,000

    Sold May 28, 2026

    1036 Manchester Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Below List Price
    • $248/SF
    • 22 Days On Market

    Current Estimated Value $390,900

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    1036 Manchester Cir, Winter Park, FL 32792
  • /2

    $335,000

    Sold Sep 23, 2025

    5144 N Orange Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 1976

    Last Sold Summary

    • 16% Below List Price
    • $263/SF
    • 128 Days On Market

    Current Estimated Value $343,669

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    5144 N Orange Ave, Winter Park, FL 32792
  • /2

    $145,000

    Sold Aug 13, 2025

    7352 Swallow Run, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 802 Sq Ft
    • Built 1983

    Last Sold Summary

    • 39% Below List Price
    • $181/SF
    • 68 Days On Market

    Current Estimated Value $148,524

    Last Listing Agent Ashley Quandt LEERDAM PROPERTIES INC.

    7352 Swallow Run, Winter Park, FL 32792
  • /2

    $1,905,000

    Sold Apr 10, 2026

    501 Henkel Cir, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,746 Sq Ft
    • Built 2009

    Last Sold Summary

    • 4% Above List Price
    • $509/SF
    • 4 Days On Market

    Current Estimated Value $1,956,262

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    501 Henkel Cir, Winter Park, FL 32789
  • /2

    $489,000

    Sold Jun 17, 2026

    5236 Albert Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,843 Sq Ft
    • Built 1979

    Last Sold Summary

    • $265/SF
    • 3 Days On Market

    Current Estimated Value $488,813

    Last Listing Agent Cody Hancock COLDWELL BANKER REALTY

    5236 Albert Dr, Winter Park, FL 32792
  • /2

    $399,900

    Sold Oct 08, 2025

    7553 Laurel Springs Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 1973

    Last Sold Summary

    • $338/SF
    • 20 Days On Market

    Current Estimated Value $404,058

    Last Listing Agent Yamila Lopez EMPIRE NETWORK REALTY

    7553 Laurel Springs Dr, Winter Park, FL 32792
  • /2

    $420,000

    Sold Jan 15, 2026

    1847 Azalea Ave, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 1,477 Sq Ft
    • Built 1961

    Last Sold Summary

    • $284/SF
    • 1 Day On Market

    Current Estimated Value $424,431

    Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

    1847 Azalea Ave, Winter Park, FL 32789
  • /2

    $199,900

    Sold Nov 03, 2025

    2500 Lee Rd Unit 134, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft
    • Built 1969

    Last Sold Summary

    • 5% Below List Price
    • $310/SF
    • 130 Days On Market

    Current Estimated Value $185,870

    Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

    2500 Lee Rd Unit 134, Winter Park, FL 32789
  • /2

    $340,000

    Sold Feb 26, 2026

    7580 Aloma Pines Ct, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 1,872 Sq Ft
    • Built 2016

    Last Sold Summary

    • 7% Below List Price
    • $182/SF
    • 94 Days On Market

    Current Estimated Value $349,920

    Last Listing Agent Simon Colak USCO CAPITAL GROUP

    7580 Aloma Pines Ct, Winter Park, FL 32792
  • /2

    $250,000

    Sold Apr 10, 2026

    1823 Maywood Rd, Winter Park, FL 32792

    • 3 Beds
    • 1.5 Baths
    • 1,232 Sq Ft
    • Built 1956

    Last Sold Summary

    • $203/SF
    • 1 Day On Market

    Current Estimated Value $244,436

    Last Listing Agent Abby Nelson RE/MAX 200 REALTY

    1823 Maywood Rd, Winter Park, FL 32792
  • /2

    $266,000

    Sold Nov 19, 2025

    1500 Gay Rd Unit 9B, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft
    • Built 1972

    Last Sold Summary

    • 1% Below List Price
    • $259/SF
    • 5 Days On Market

    Current Estimated Value $255,091

    Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 9B, Winter Park, FL 32789
  • /2

    $470,000

    Sold Jan 15, 2026

    3319 Ellwood Ct, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 1,546 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Above List Price
    • $304/SF
    • 78 Days On Market

    Current Estimated Value $471,829

    Last Listing Agent Elena Sanchez BALDWIN PARK REALTY LLC

    3319 Ellwood Ct, Winter Park, FL 32792
  • /2

    $245,900

    Sold Aug 11, 2025

    195 Sandlewood Trail Unit 2, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 1,132 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $217/SF
    • 2 Days On Market

    Current Estimated Value $244,673

    Last Listing Agent Matt Merdian MERDIAN REALTY LLC

    195 Sandlewood Trail Unit 2, Winter Park, FL 32789
  • /2

    $165,000

    Sold Jun 01, 2026

    200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 793 Sq Ft
    • Built 1970

    Last Sold Summary

    • 6% Below List Price
    • $208/SF
    • 77 Days On Market

    Current Estimated Value $164,046

    Last Listing Agent Eric Zimmerman RE/MAX ADVANTAGE

    200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792
  • /2

    $425,000

    Sold Jun 26, 2026

    1923 Linden Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,117 Sq Ft
    • Built 1955

    Last Sold Summary

    • 15% Below List Price
    • $201/SF
    • 57 Days On Market

    Current Estimated Value $441,025

    Last Listing Agent Milton James COLDWELL BANKER REALTY

    1923 Linden Rd, Winter Park, FL 32792
  • /2

    $1,300,000

    Sold Sep 22, 2025

    1371 Lyndale Blvd, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,714 Sq Ft
    • Built 1949

    Last Sold Summary

    • 4% Below List Price
    • $479/SF
    • 8 Days On Market

    Current Estimated Value $1,309,890

    Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

    1371 Lyndale Blvd, Winter Park, FL 32789
  • /2

    $405,000

    Sold Jan 09, 2026

    3425 Ferndell Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,516 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $267/SF
    • 164 Days On Market

    Current Estimated Value $402,852

    Last Listing Agent Ivanhoe Alvarez LOKATION

    3425 Ferndell Dr, Winter Park, FL 32792
  • /2

    $235,000

    Sold Jan 29, 2026

    613 Orange Tree Ct Unit 507, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,256 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Below List Price
    • $187/SF
    • 10 Days On Market

    Current Estimated Value $232,163

    Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

    613 Orange Tree Ct Unit 507, Maitland, FL 32751
  • /2

    $298,000

    Sold Aug 15, 2025

    2206 Bonanza Ave, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,776 Sq Ft
    • Built 1971

    Last Sold Summary

    • 15% Below List Price
    • $168/SF
    • 9 Days On Market

    Current Estimated Value $425,920

    Last Listing Agent Hannah Evans FLORIDA REALTY INVESTMENTS

    2206 Bonanza Ave, Winter Park, FL 32792
  • /2

    $279,000

    Sold Aug 11, 2025

    Unlisted Address

    • 2 Beds
    • 2.5 Baths
    • 1,186 Sq Ft
    • Built 1981

    Last Sold Summary

    • $235/SF
    • 4 Days On Market

    Current Estimated Value $278,262

    Last Listing Agent Adriana Gonzalez PERFECT INVESTMENT REALTY

    Unlisted Address
  • /24

    $649,000

    Sold Oct 17, 2025

    2304 Depauw Ave, Orlando, FL 32804

    • 3 Beds
    • 2.5 Baths
    • 1,668 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $389/SF
    • 199 Days On Market

    Current Estimated Value $648,000

    David Weekley Homes Central Living - Downtown

    2304 Depauw Ave, Orlando, FL 32804

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home