1,098

Recently Sold Winter Park, FL Homes

Section Image
  • 521 S Phelps Ave, Winter Park, FL 32789
    521 S Phelps Ave, 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 $2,223,005

    Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

    521 S Phelps Ave, Winter Park, FL 32789
  • 2003 Bentwood Dr, Winter Park, FL 32792
    2003 Bentwood Dr, Winter Park, FL 32792
    /2

    $430,000 Sold Jul 25, 2025

    2003 Bentwood Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,675 Sq Ft
    • Built 1981

    Last Sold Summary

    • 1% Above List Price
    • $257/SF
    • 16 Days On Market

    Current Estimated Value $440,434

    Last Listing Agent Heather Kolin PALMANO GROUP RE BROKERAGE LLC

    2003 Bentwood Dr, Winter Park, FL 32792
  • 2151 Conifer Ave, Winter Park, FL 32792
    2151 Conifer Ave, 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 $454,765

    Last Listing Agent Denise Korrey KORR REALTY CORP

    2151 Conifer Ave, Winter Park, FL 32792
  • 2411 Gallery View Dr Unit 5, Winter Park, FL 32792
    2411 Gallery View Dr Unit 5, 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 $286,274

    Last Listing Agent Maria Elena Perez MEP REALTY INVESTMENTS LLC

    2411 Gallery View Dr Unit 5, Winter Park, FL 32792
  • 200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 2302, 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 $183,668

    Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

    200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
  • 1000 S Semoran Blvd Unit 512, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 512, 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 $128,859

    Last Listing Agent Cristina Burgos REALSOURCE PROPERTY MANGNT LLC

    1000 S Semoran Blvd Unit 512, Winter Park, FL 32792
  • 1392 Indiana Ave, Winter Park, FL 32789
    1392 Indiana Ave, Winter Park, FL 32789
    /2

    $580,000 Sold May 16, 2025

    1392 Indiana Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,936 Sq Ft
    • Built 2008

    Last Sold Summary

    • 11% Below List Price
    • $300/SF
    • 123 Days On Market

    Current Estimated Value $556,574

    Last Listing Agent Cody Hancock COLDWELL BANKER REALTY

    1392 Indiana Ave, Winter Park, FL 32789
  • 2028 Sussex Rd, Winter Park, FL 32792
    2028 Sussex Rd, Winter Park, FL 32792
    /2

    $426,000 Sold Jul 03, 2025

    2028 Sussex Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft
    • Built 1973

    Last Sold Summary

    • 6% Below List Price
    • $254/SF
    • 39 Days On Market

    Current Estimated Value $438,699

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    2028 Sussex Rd, Winter Park, FL 32792
  • 765 Via Lugano, Winter Park, FL 32789
    765 Via Lugano, Winter Park, FL 32789
    /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 $4,664,184

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

    765 Via Lugano, Winter Park, FL 32789
  • 731 Williams Dr, Winter Park, FL 32789
    731 Williams Dr, Winter Park, FL 32789
    /2

    $3,100,000 Sold Jun 27, 2025

    731 Williams Dr, Winter Park, FL 32789

    • 5 Beds
    • 6 Baths
    • 4,260 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $728/SF
    • 45 Days On Market

    Current Estimated Value $2,939,252

    Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

    731 Williams Dr, Winter Park, FL 32789
  • 1445 Holts Grove Cir, Winter Park, FL 32789
    1445 Holts Grove Cir, 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 $2,654,470

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

    1445 Holts Grove Cir, Winter Park, FL 32789
  • 3083 Crane Strand Dr, Winter Park, FL 32792
    3083 Crane Strand Dr, Winter Park, FL 32792
    /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 $370,832

    Last Listing Agent Sheri Malin REDFIN CORPORATION

    3083 Crane Strand Dr, Winter Park, FL 32792
  • 1901 Loch Berry Rd, Winter Park, FL 32792
    1901 Loch Berry Rd, 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 $537,712

    Last Listing Agent Monica Tipirneni FOLIO REALTY LLC

    1901 Loch Berry Rd, Winter Park, FL 32792
  • 609 Langholm Dr, Winter Park, FL 32789
    609 Langholm Dr, Winter Park, FL 32789
    /2

    $916,000 Sold Jul 17, 2025

    609 Langholm Dr, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,981 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Below List Price
    • $462/SF
    • 8 Days On Market

    Current Estimated Value $904,622

    Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

    609 Langholm Dr, Winter Park, FL 32789
  • 2421 Summerfield Rd, Winter Park, FL 32792
    2421 Summerfield 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 $650,425

    Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

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

    $498,000 Sold May 28, 2025

    808 Denton Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft
    • Built 1961

    Last Sold Summary

    • $286/SF
    • 4 Days On Market

    Current Estimated Value $488,555

    Last Listing Agent Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

    808 Denton Rd, Winter Park, FL 32792
  • 2171 Forrest Rd, Winter Park, FL 32789
    2171 Forrest Rd, Winter Park, FL 32789
    /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 $3,358,092

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

    2171 Forrest Rd, Winter Park, FL 32789
  • 207 E Kings Way, Winter Park, FL 32789
    207 E Kings Way, 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 $2,426,211

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

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

    $1,645,000 Sold May 20, 2025

    681 Balmoral Rd, Winter Park, FL 32789

    • Land
    • 1.14 Acres
    • $1,442,982 per Acre

    Last Sold Summary

    • 17% Below List Price
    • 55 Days On Market

    Current Estimated Value $1,598,071

    Last Listing Agent Chris Burden EPIC REAL ESTATE ADVISORS LLC

    681 Balmoral Rd, Winter Park, FL 32789
  • 5144 N Orange Ave, Winter Park, FL 32792
    5144 N Orange Ave, 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 $337,543

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    5144 N Orange Ave, Winter Park, FL 32792
  • 1109 Denton Rd, Winter Park, FL 32792
    1109 Denton Rd, Winter Park, FL 32792
    /2

    $397,000 Sold Jul 01, 2025

    1109 Denton Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,236 Sq Ft
    • Built 1963

    Last Sold Summary

    • 3% Below List Price
    • $321/SF
    • 83 Days On Market

    Current Estimated Value $398,354

    Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

    1109 Denton Rd, Winter Park, FL 32792
  • 7352 Swallow Run, Winter Park, FL 32792
    7352 Swallow Run, 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 $142,632

    Last Listing Agent Ashley Quandt LEERDAM PROPERTIES INC.

    7352 Swallow Run, Winter Park, FL 32792
  • 1979 Staunton Ave, Winter Park, FL 32789
    1979 Staunton Ave, Winter Park, FL 32789
    /2

    $228,000 Sold Jun 27, 2025

    1979 Staunton Ave, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 736 Sq Ft
    • Built 1948

    Last Sold Summary

    • 24% Below List Price
    • $310/SF
    • 16 Days On Market

    Current Estimated Value $226,368

    Last Listing Agent Michael Kara CORBELO LLC

    1979 Staunton Ave, Winter Park, FL 32789
  • 501 Henkel Cir, Winter Park, FL 32789
    501 Henkel Cir, Winter Park, FL 32789
    /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 $1,855,042

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    501 Henkel Cir, Winter Park, FL 32789
  • 7553 Laurel Springs Dr, Winter Park, FL 32792
    7553 Laurel Springs 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 $393,107

    Last Listing Agent Yamila Lopez EMPIRE NETWORK REALTY

    7553 Laurel Springs Dr, Winter Park, FL 32792
  • 1847 Azalea Ave, Winter Park, FL 32789
    1847 Azalea Ave, Winter Park, FL 32789
    /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 $414,739

    Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

    1847 Azalea Ave, Winter Park, FL 32789
  • 2500 Lee Rd Unit 134, Winter Park, FL 32789
    2500 Lee Rd Unit 134, 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 $189,746

    Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

    2500 Lee Rd Unit 134, Winter Park, FL 32789
  • 700 Melrose Ave Unit E24, Winter Park, FL 32789
    700 Melrose Ave Unit E24, Winter Park, FL 32789
    700 Melrose Ave Unit E24, Winter Park, FL 32789
    /19

    $172,000 Sold May 23, 2025

    700 Melrose Ave Unit E24, Winter Park, FL 32789

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

    Last Sold Summary

    • 14% Below List Price
    • $219/SF
    • 164 Days On Market

    Current Estimated Value $180,280

    Last Listing Agent Susan Dering HOMEVEST REALTY

    700 Melrose Ave Unit E24, Winter Park, FL 32789
  • 7580 Aloma Pines Ct, Winter Park, FL 32792
    7580 Aloma Pines Ct, Winter Park, FL 32792
    /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 $348,697

    Last Listing Agent Simon Colak USCO CAPITAL GROUP

    7580 Aloma Pines Ct, Winter Park, FL 32792
  • 1823 Maywood Rd, Winter Park, FL 32792
    1823 Maywood Rd, 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 $220,273

    Last Listing Agent Abby Nelson RE/MAX 200 REALTY

    1823 Maywood Rd, Winter Park, FL 32792
  • 1500 Gay Rd Unit 9B, Winter Park, FL 32789
    1500 Gay Rd Unit 9B, Winter Park, FL 32789
    /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 $262,699

    Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 9B, Winter Park, FL 32789
  • 3319 Ellwood Ct, Winter Park, FL 32792
    3319 Ellwood Ct, Winter Park, FL 32792
    /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 $466,549

    Last Listing Agent Elena Sanchez BALDWIN PARK REALTY LLC

    3319 Ellwood Ct, Winter Park, FL 32792
  • 195 Sandlewood Trail Unit 2, Winter Park, FL 32789
    195 Sandlewood Trail Unit 2, Winter Park, FL 32789
    /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 $253,849

    Last Listing Agent Matt Merdian MERDIAN REALTY LLC

    195 Sandlewood Trail Unit 2, Winter Park, FL 32789
  • 1570 Grove Terrace, Winter Park, FL 32789
    1570 Grove Terrace, Winter Park, FL 32789
    /2

    $725,000 Sold May 13, 2025

    1570 Grove Terrace, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,663 Sq Ft
    • Built 1991

    Last Sold Summary

    • $436/SF

    Current Estimated Value $753,538

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

    1570 Grove Terrace, Winter Park, FL 32789
  • 1371 Lyndale Blvd, Winter Park, FL 32789
    1371 Lyndale Blvd, Winter Park, FL 32789
    /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 $1,261,078

    Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

    1371 Lyndale Blvd, Winter Park, FL 32789
  • 1189 Lazy Hollow Place, Winter Park, FL 32792
    1189 Lazy Hollow Place, Winter Park, FL 32792
    /2

    $421,700 Sold May 29, 2025

    1189 Lazy Hollow Place, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,525 Sq Ft
    • Built 1984

    Last Sold Summary

    • $277/SF
    • 7 Days On Market

    Current Estimated Value $427,900

    Last Listing Agent Virginia Silberstein ORLANDO EXPERT REALTY LLC

    1189 Lazy Hollow Place, Winter Park, FL 32792
  • 3425 Ferndell Dr, Winter Park, FL 32792
    3425 Ferndell Dr, Winter Park, FL 32792
    /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 $391,495

    Last Listing Agent Ivanhoe Alvarez LOKATION

    3425 Ferndell Dr, Winter Park, FL 32792
  • 613 Orange Tree Ct Unit 507, Maitland, FL 32751
    613 Orange Tree Ct Unit 507, Maitland, FL 32751
    /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 $234,240

    Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

    613 Orange Tree Ct Unit 507, Maitland, FL 32751
  • 2206 Bonanza Ave, Winter Park, FL 32792
    2206 Bonanza Ave, Winter Park, FL 32792
    /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 $424,901

    Last Listing Agent Hannah Evans FLORIDA REALTY INVESTMENTS

    2206 Bonanza Ave, Winter Park, FL 32792
  • Unlisted Address
    Unlisted Address
    /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 $272,936

    Last Listing Agent Adriana Gonzalez PERFECT INVESTMENT REALTY

    Unlisted Address

Showing Results 41 - 80, Page 2 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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