1,143

Recently Sold Winter Park, FL Homes

Section Image
  • 643 Balmoral Rd, Winter Park, FL 32789
    643 Balmoral Rd, Winter Park, FL 32789
    /2

    $1,767,500 Sold Mar 21, 2025

    643 Balmoral Rd, Winter Park, FL 32789

    • Land
    • 0.71 Acre
    • $2,489,437 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 17 Days On Market

    Current Estimated Value $1,787,442

    Last Listing Agent Laura Hope COMPASS FLORIDA LLC

    643 Balmoral Rd, Winter Park, FL 32789
  • 260 Orange Terrace Dr, Winter Park, FL 32789
    260 Orange Terrace Dr, Winter Park, FL 32789
    /2

    $475,000 Sold Nov 14, 2025

    260 Orange Terrace Dr, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 1,330 Sq Ft
    • Built 1953

    Last Sold Summary

    • 1% Below List Price
    • $357/SF
    • 6 Days On Market

    Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

    260 Orange Terrace Dr, Winter Park, FL 32789
  • 660 Arjay Way, Winter Park, FL 32789
    660 Arjay Way, Winter Park, FL 32789
    /2

    $1,525,000 Sold Feb 14, 2025

    660 Arjay Way, Winter Park, FL 32789

    • 4 Beds
    • 4 Baths
    • 3,237 Sq Ft
    • Built 1957

    Last Sold Summary

    • 8% Below List Price
    • $471/SF
    • 133 Days On Market

    Current Estimated Value $1,544,887

    Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

    660 Arjay Way, Winter Park, FL 32789
  • 1891 Lake Spier Dr, Winter Park, FL 32789
    1891 Lake Spier Dr, Winter Park, FL 32789
    /2

    $2,800,000 Sold Aug 14, 2025

    1891 Lake Spier Dr, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 3,932 Sq Ft
    • Built 2024

    Last Sold Summary

    • 12% Below List Price
    • $712/SF
    • 57 Days On Market

    Current Estimated Value $2,780,920

    Last Listing Agent Mike Derenthal DERENTHAL REALTY

    1891 Lake Spier Dr, Winter Park, FL 32789
  • 1005 Leeds Ct, Winter Park, FL 32792
    1005 Leeds Ct, Winter Park, FL 32792
    /2

    $499,000 Sold Mar 26, 2025

    1005 Leeds Ct, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,032 Sq Ft
    • Built 1977

    Last Sold Summary

    • $246/SF
    • 13 Days On Market

    Current Estimated Value $499,843

    Last Listing Agent Devonna Craner CRANER AND COMPANY REAL ESTATE GROUP LLC

    1005 Leeds Ct, Winter Park, FL 32792
  • 690 Osceola Ave Unit 410, Winter Park, FL 32789
    690 Osceola Ave Unit 410, Winter Park, FL 32789
    /2

    $425,000 Sold Aug 04, 2025

    690 Osceola Ave Unit 410, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • Built 1969

    Last Sold Summary

    • 3% Below List Price
    • $370/SF
    • 8 Days On Market

    Current Estimated Value $432,533

    Last Listing Agent Catherine Mitchell SANDRONI HOLDINGS REAL ESTATE LLC

    690 Osceola Ave Unit 410, Winter Park, FL 32789
  • 2804 Dike Rd, Winter Park, FL 32792
    2804 Dike Rd, Winter Park, FL 32792
    /2

    $750,000 Sold Jun 09, 2025

    2804 Dike Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,503 Sq Ft
    • Built 1980

    Last Sold Summary

    • 12% Below List Price
    • $300/SF
    • 284 Days On Market

    Current Estimated Value $763,059

    Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

    2804 Dike Rd, Winter Park, FL 32792
  • 2312 Poinciana Rd, Winter Park, FL 32792
    2312 Poinciana Rd, Winter Park, FL 32792
    /2

    $440,000 Sold Jul 10, 2025

    2312 Poinciana Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,806 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Below List Price
    • $244/SF
    • 6 Days On Market

    Current Estimated Value $447,679

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    2312 Poinciana Rd, Winter Park, FL 32792
  • 1651 N Park Ave, Winter Park, FL 32789
    1651 N Park Ave, Winter Park, FL 32789
    /2

    $505,000 Sold Jan 05, 2026

    1651 N Park Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,263 Sq Ft
    • Built 1965

    Last Sold Summary

    • $400/SF
    • 0 Days On Market

    Last Listing Agent Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

    1651 N Park Ave, Winter Park, FL 32789
  • 1032 Early Ave, Winter Park, FL 32789
    1032 Early Ave, Winter Park, FL 32789
    /2

    $2,100,000 Sold Apr 15, 2025

    1032 Early Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,894 Sq Ft
    • Built 1999

    Last Sold Summary

    • 9% Below List Price
    • $726/SF
    • 35 Days On Market

    Current Estimated Value $2,087,204

    Last Listing Agent Teresa Corbett KINCAID REALTY

    1032 Early Ave, Winter Park, FL 32789
  • 609 Gallery Dr Unit 2, Winter Park, FL 32792
    609 Gallery Dr Unit 2, Winter Park, FL 32792
    /2

    $270,000 Sold Apr 04, 2025

    609 Gallery Dr Unit 2, Winter Park, FL 32792

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

    Last Sold Summary

    • 5% Below List Price
    • $291/SF
    • 12 Days On Market

    Current Estimated Value $266,353

    Last Listing Agent Kim Oliver NONA LEGACY POWERED BY LA ROSA

    609 Gallery Dr Unit 2, Winter Park, FL 32792
  • 1000 S Semoran Blvd Unit 608, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 608, Winter Park, FL 32792
    /2

    $119,000 Sold Dec 08, 2025

    1000 S Semoran Blvd Unit 608, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,049 Sq Ft
    • Built 1969

    Last Sold Summary

    • 30% Below List Price
    • $113/SF
    • 155 Days On Market

    Last Listing Agent Maria Peralta CHARLES RUTENBERG REALTY ORLANDO

    1000 S Semoran Blvd Unit 608, Winter Park, FL 32792
  • 1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789
    1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789
    /2

    $750,000 Sold Jan 12, 2026

    1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,957 Sq Ft
    • Built 2007

    Last Sold Summary

    • 6% Below List Price
    • $383/SF
    • 84 Days On Market

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

    1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789
  • 2426 Windward Way, Winter Park, FL 32792
    2426 Windward Way, Winter Park, FL 32792
    /2

    $270,000 Sold Aug 28, 2025

    2426 Windward Way, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 932 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $290/SF
    • 50 Days On Market

    Current Estimated Value $272,609

    Last Listing Agent Kim Coburn RE/MAX TOWN & COUNTRY REALTY

    2426 Windward Way, Winter Park, FL 32792
  • 2809 Sanbina St, Winter Park, FL 32789
    2809 Sanbina St, Winter Park, FL 32789
    /2

    $420,000 Sold Jul 11, 2025

    2809 Sanbina St, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 1961

    Last Sold Summary

    • 2% Below List Price
    • $368/SF
    • 4 Days On Market

    Current Estimated Value $424,723

    Last Listing Agent Harry Kazarian STRONG FOUNDATION REALTY LLC

    2809 Sanbina St, Winter Park, FL 32789
  • 1545 Indiana Ave Unit B, Winter Park, FL 32789
    1545 Indiana Ave Unit B, Winter Park, FL 32789
    /2

    $480,000 Sold Jul 28, 2025

    1545 Indiana Ave Unit B, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,598 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $300/SF
    • 3 Days On Market

    Current Estimated Value $486,076

    Last Listing Agent Ron Murray MAGIC REALTY LLC

    1545 Indiana Ave Unit B, Winter Park, FL 32789
  • 1911 Stonehurst Rd, Winter Park, FL 32789
    1911 Stonehurst Rd, Winter Park, FL 32789
    /2

    $2,910,000 Sold Jul 21, 2025

    1911 Stonehurst Rd, Winter Park, FL 32789

    • 4 Beds
    • 6 Baths
    • 5,097 Sq Ft
    • Built 2001

    Last Sold Summary

    • 14% Below List Price
    • $571/SF
    • 82 Days On Market

    Current Estimated Value $2,909,882

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1911 Stonehurst Rd, Winter Park, FL 32789
  • 1871 Winchester Dr, Winter Park, FL 32789
    1871 Winchester Dr, Winter Park, FL 32789
    /2

    $1,685,000 Sold Apr 30, 2025

    1871 Winchester Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,421 Sq Ft
    • Built 1957

    Last Sold Summary

    • $493/SF

    Current Estimated Value $1,663,897

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

    1871 Winchester Dr, Winter Park, FL 32789
  • 513 Dunraven Dr, Winter Park, FL 32792
    513 Dunraven Dr, Winter Park, FL 32792
    /2

    $370,000 Sold Oct 20, 2025

    513 Dunraven Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft
    • Built 1956

    Last Sold Summary

    • $254/SF

    Current Estimated Value $463,344

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

    513 Dunraven Dr, Winter Park, FL 32792
  • 2460 Harbour Way, Winter Park, FL 32792
    2460 Harbour Way, Winter Park, FL 32792
    /2

    $277,000 Sold Feb 28, 2025

    2460 Harbour Way, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,019 Sq Ft
    • Built 1978

    Last Sold Summary

    • 1% Above List Price
    • $272/SF
    • 1 Day On Market

    Current Estimated Value $273,872

    Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

    2460 Harbour Way, Winter Park, FL 32792
  • 1809 Pineview Cir, Winter Park, FL 32792
    1809 Pineview Cir, Winter Park, FL 32792
    /2

    $465,000 Sold Sep 29, 2025

    1809 Pineview Cir, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,631 Sq Ft
    • Built 1956

    Last Sold Summary

    • 15% Below List Price
    • $285/SF
    • 106 Days On Market

    Current Estimated Value $453,822

    Last Listing Agent Eric Trumble II CHARLES RUTENBERG REALTY ORLANDO

    1809 Pineview Cir, Winter Park, FL 32792
  • 1585 Chestnut Ave, Winter Park, FL 32789
    1585 Chestnut Ave, Winter Park, FL 32789
    /2

    $987,500 Sold Jun 10, 2025

    1585 Chestnut Ave, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • Built 1959

    Last Sold Summary

    • 21% Below List Price
    • $445/SF
    • 101 Days On Market

    Current Estimated Value $1,006,224

    Last Listing Agent Ashley Landers KELLER WILLIAMS WINTER PARK

    1585 Chestnut Ave, Winter Park, FL 32789
  • 151 N Orlando Ave Unit 131, Winter Park, FL 32789
    151 N Orlando Ave Unit 131, Winter Park, FL 32789
    /2

    $385,000 Sold Jul 12, 2025

    151 N Orlando Ave Unit 131, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Below List Price
    • $385/SF
    • 355 Days On Market

    Current Estimated Value $376,926

    Last Listing Agent Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

    151 N Orlando Ave Unit 131, Winter Park, FL 32789
  • 7249 Abbey Ln, Winter Park, FL 32792
    7249 Abbey Ln, Winter Park, FL 32792
    /2

    $425,000 Sold Jul 07, 2025

    7249 Abbey Ln, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,508 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $282/SF
    • 42 Days On Market

    Current Estimated Value $432,957

    Last Listing Agent Jackie Criswell RE/MAX TOWN & COUNTRY REALTY

    7249 Abbey Ln, Winter Park, FL 32792
  • 1610 Oakhurst Ave, Winter Park, FL 32789
    1610 Oakhurst Ave, Winter Park, FL 32789
    /2

    $3,200,000 Sold Oct 20, 2025

    1610 Oakhurst Ave, Winter Park, FL 32789

    • 5 Beds
    • 7 Baths
    • 4,255 Sq Ft
    • Built 2021

    Last Sold Summary

    • 2% Below List Price
    • $752/SF
    • 3 Days On Market

    Current Estimated Value $3,139,889

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

    1610 Oakhurst Ave, Winter Park, FL 32789
  • 1791 Spruce Ave, Winter Park, FL 32789
    1791 Spruce Ave, Winter Park, FL 32789
    /2

    $849,900 Sold Jun 10, 2025

    1791 Spruce Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,776 Sq Ft
    • Built 1956

    Last Sold Summary

    • $479/SF
    • 8 Days On Market

    Current Estimated Value $870,440

    Last Listing Agent Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

    1791 Spruce Ave, Winter Park, FL 32789
  • 3103 Ash Park Loop, Winter Park, FL 32792
    3103 Ash Park Loop, Winter Park, FL 32792
    /2

    $335,000 Sold Sep 17, 2025

    3103 Ash Park Loop, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Below List Price
    • $238/SF
    • 20 Days On Market

    Current Estimated Value $339,297

    Last Listing Agent Pam Hagood Ryan PREMIER SOTHEBY'S INTL. REALTY

    3103 Ash Park Loop, Winter Park, FL 32792
  • 7468 Swallow Run Unit 38, Winter Park, FL 32792
    7468 Swallow Run Unit 38, Winter Park, FL 32792
    /2

    $215,000 Sold Jun 13, 2025

    7468 Swallow Run Unit 38, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,578 Sq Ft
    • Built 1974

    Last Sold Summary

    • 12% Below List Price
    • $136/SF
    • 52 Days On Market

    Current Estimated Value $219,164

    Last Listing Agent Chris Creegan CREEGAN GROUP

    7468 Swallow Run Unit 38, Winter Park, FL 32792
  • 215 E Canton Ave Unit 215, Winter Park, FL 32789
    215 E Canton Ave Unit 215, Winter Park, FL 32789
    /2

    $464,000 Sold May 01, 2025

    215 E Canton Ave Unit 215, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,057 Sq Ft
    • Built 1971

    Last Sold Summary

    • 7% Below List Price
    • $439/SF
    • 78 Days On Market

    Last Listing Agent Harris Ganey HARRISS M GANEY REALTY

    215 E Canton Ave Unit 215, Winter Park, FL 32789
  • 2105 Fosgate Dr, Winter Park, FL 32789
    2105 Fosgate Dr, Winter Park, FL 32789
    /2

    $1,186,200 Sold Oct 30, 2025

    2105 Fosgate Dr, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 3,068 Sq Ft
    • Built 1956

    Last Sold Summary

    • 18% Below List Price
    • $387/SF
    • 145 Days On Market

    Current Estimated Value $1,190,615

    Last Listing Agent Eileen Winfrey IAD FLORIDA LLC

    2105 Fosgate Dr, Winter Park, FL 32789
  • 1460 Via Sangro Place, Winter Park, FL 32792
    1460 Via Sangro Place, Winter Park, FL 32792
    /2

    $1,500,000 Sold Dec 23, 2025

    1460 Via Sangro Place, Winter Park, FL 32792

    • 7 Beds
    • 4 Baths
    • 5,111 Sq Ft
    • Built 2015

    Last Sold Summary

    • 6% Below List Price
    • $293/SF
    • 18 Days On Market

    Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

    1460 Via Sangro Place, Winter Park, FL 32792
  • 1424 Cavendish Rd, Winter Park, FL 32789
    1424 Cavendish Rd, Winter Park, FL 32789
    /2

    $585,000 Sold Apr 07, 2025

    1424 Cavendish Rd, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,132 Sq Ft
    • Built 1949

    Last Sold Summary

    • 1% Below List Price
    • $517/SF
    • 38 Days On Market

    Current Estimated Value $578,292

    Last Listing Agent Lisa Grey KEYSEEKERS REAL ESTATE

    1424 Cavendish Rd, Winter Park, FL 32789
  • 2804 Mulford Ave, Winter Park, FL 32789
    2804 Mulford Ave, Winter Park, FL 32789
    /2

    $510,000 Sold Jul 22, 2025

    2804 Mulford Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft
    • Built 1953

    Last Sold Summary

    • $335/SF

    Current Estimated Value $511,288

    Last Listing Agent Megan Lowe FANNIE HILLMAN & ASSOCIATES

    2804 Mulford Ave, Winter Park, FL 32789
  • 2573 Madeline Ave, Winter Park, FL 32789
    2573 Madeline Ave, Winter Park, FL 32789
    /2

    $850,000 Sold Dec 05, 2025

    2573 Madeline Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,035 Sq Ft
    • Built 2023

    Last Sold Summary

    • 5% Below List Price
    • $418/SF
    • 5 Days On Market

    Last Listing Agent Kristen Hamilton LOMBARDO TEAM REAL ESTATE LLC

    2573 Madeline Ave, Winter Park, FL 32789
  • 1871 Staunton Ave, Winter Park, FL 32789
    1871 Staunton Ave, Winter Park, FL 32789
    /2

    $425,000 Sold Aug 29, 2025

    1871 Staunton Ave, Winter Park, FL 32789

    • Land
    • 0.32 Acre
    • $1,328,125 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 3 Days On Market

    Current Estimated Value $423,333

    Last Listing Agent Greg Staker WATSON REALTY CORP.

    1871 Staunton Ave, Winter Park, FL 32789
  • 1414 Bessmor Rd, Winter Park, FL 32789
    1414 Bessmor Rd, Winter Park, FL 32789
    /2

    $475,000 Sold Sep 19, 2025

    1414 Bessmor Rd, Winter Park, FL 32789

    • Land
    • 0.16 Acre
    • $2,968,750 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 22 Days On Market

    Current Estimated Value $469,819

    Last Listing Agent Miranda Azer PARKVIEW REAL ESTATE

    1414 Bessmor Rd, Winter Park, FL 32789
  • 1716 Palmer Ave, Winter Park, FL 32789
    1716 Palmer Ave, Winter Park, FL 32789
    /2

    $1,500,000 Sold Mar 04, 2025

    1716 Palmer Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 3,270 Sq Ft
    • Built 1951

    Last Sold Summary

    • 14% Below List Price
    • $459/SF
    • 92 Days On Market

    Current Estimated Value $1,464,207

    Last Listing Agent Jonathan Minerick HOMECOIN.COM

    1716 Palmer Ave, Winter Park, FL 32789
  • 3214 Lowndes Dr, Winter Park, FL 32792
    3214 Lowndes Dr, Winter Park, FL 32792
    /2

    $395,000 Sold Dec 09, 2025

    3214 Lowndes Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1965

    Last Sold Summary

    • 1% Below List Price
    • $329/SF
    • 53 Days On Market

    Last Listing Agent Gregory Roberts LPT REALTY LLC

    3214 Lowndes Dr, Winter Park, FL 32792
  • 3131 Ash Park Loop, Winter Park, FL 32792
    3131 Ash Park Loop, Winter Park, FL 32792
    /2

    $335,000 Sold Jun 26, 2025

    3131 Ash Park Loop, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1986

    Last Sold Summary

    • 16% Below List Price
    • $238/SF
    • 120 Days On Market

    Current Estimated Value $346,133

    Last Listing Agent Amanda Binns STRICKLAND REALTY GROUP INC

    3131 Ash Park Loop, Winter Park, FL 32792
  • 1840 Shiloh Ln, Winter Park, FL 32789
    1840 Shiloh Ln, Winter Park, FL 32789
    /2

    $1,025,000 Sold Jan 27, 2026

    1840 Shiloh Ln, Winter Park, FL 32789

    • Land
    • 0.27 Acre
    • $3,796,296 per Acre

    Last Sold Summary

    • 2 Days On Market

    Last Listing Agent Gwyn Clark FANNIE HILLMAN & ASSOCIATES

    1840 Shiloh Ln, Winter Park, FL 32789

Showing Results 601 - 640, Page 16 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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