1,172

Recently Sold Winter Park, FL Homes

Section Image
  • 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

    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 $997,668

    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 $375,996

    Last Listing Agent Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

    151 N Orlando Ave Unit 131, Winter Park, FL 32789
  • 1571 Oneco Ave, Winter Park, FL 32789
    1571 Oneco Ave, Winter Park, FL 32789
    /2

    $1,129,000 Sold Jan 31, 2025

    1571 Oneco Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,510 Sq Ft
    • Built 2009

    Last Sold Summary

    • 5% Below List Price
    • $450/SF
    • 41 Days On Market

    Current Estimated Value $1,129,695

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    1571 Oneco Ave, 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 $425,392

    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

    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 $851,777

    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 $222,365

    Last Listing Agent Chris Creegan CREEGAN GROUP

    7468 Swallow Run Unit 38, Winter Park, FL 32792
  • 100 S Virginia Ave Unit 201, Winter Park, FL 32789
    100 S Virginia Ave Unit 201, Winter Park, FL 32789
    /2

    $1,099,717 Sold Dec 30, 2024

    100 S Virginia Ave Unit 201, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 2,756 Sq Ft
    • Built 2008

    Last Sold Summary

    • 8% Below List Price
    • $399/SF
    • 51 Days On Market

    Current Estimated Value $1,129,469

    Last Listing Agent Tiffany Grindstaff KELLY PRICE & COMPANY LLC

    100 S Virginia Ave Unit 201, Winter Park, FL 32789
  • 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

    Last Listing Agent Eileen Winfrey LPT REALTY, 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 $572,774

    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 $414,667

    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 $1,450,470

    Last Listing Agent Jonathan Minerick HOMECOIN.COM

    1716 Palmer Ave, Winter Park, FL 32789
  • 1190 Village Forest Place, Winter Park, FL 32792
    1190 Village Forest Place, Winter Park, FL 32792
    /2

    $420,000 Sold Jan 31, 2025

    1190 Village Forest Place, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,525 Sq Ft
    • Built 1985

    Last Sold Summary

    • 7% Below List Price
    • $275/SF
    • 135 Days On Market

    Current Estimated Value $414,963

    Last Listing Agent Laura Petersen YOUR HOME SOLD GUARANTEED REALTY

    1190 Village Forest Place, Winter Park, FL 32792
  • 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 $343,793

    Last Listing Agent Amanda Binns STRICKLAND REALTY GROUP INC

    3131 Ash Park Loop, Winter Park, FL 32792
  • 786 Antonette Ave, Winter Park, FL 32789
    786 Antonette Ave, Winter Park, FL 32789
    /2

    $600,000 Sold Oct 31, 2025

    786 Antonette Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,146 Sq Ft
    • Built 1925

    Last Sold Summary

    • 25% Below List Price
    • $524/SF
    • 200 Days On Market

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    786 Antonette Ave, Winter Park, FL 32789
  • 2828 Whispering Way, Winter Park, FL 32792
    2828 Whispering Way, Winter Park, FL 32792
    /2

    $379,000 Sold Oct 01, 2025

    2828 Whispering Way, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $289/SF
    • 99 Days On Market

    Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

    2828 Whispering Way, Winter Park, FL 32792
  • 2313 Loch Lomond Dr, Winter Park, FL 32792
    2313 Loch Lomond Dr, Winter Park, FL 32792
    /2

    $500,000 Sold Feb 04, 2025

    2313 Loch Lomond Dr, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 1,570 Sq Ft
    • Built 1948

    Last Sold Summary

    • 9% Below List Price
    • $318/SF
    • 298 Days On Market

    Current Estimated Value $483,304

    Last Listing Agent Brian Mitnik RE/MAX 200 REALTY

    2313 Loch Lomond Dr, Winter Park, FL 32792
  • 2009 Nottingdale Ln, Winter Park, FL 32792
    2009 Nottingdale Ln, Winter Park, FL 32792
    /2

    $386,000 Sold Jul 09, 2025

    2009 Nottingdale Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,582 Sq Ft
    • Built 1980

    Last Sold Summary

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

    Current Estimated Value $391,169

    Last Listing Agent Wendy Calvet OLDE TOWN BROKERS INC

    2009 Nottingdale Ln, Winter Park, FL 32792
  • 821 Carver St, Winter Park, FL 32789
    821 Carver St, Winter Park, FL 32789
    /2

    $320,000 Sold Feb 18, 2025

    821 Carver St, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 904 Sq Ft
    • Built 1949

    Last Sold Summary

    • 6% Below List Price
    • $354/SF
    • 168 Days On Market

    Current Estimated Value $339,986

    Last Listing Agent Alec Boe INNOVATIVE REALTY, LLC

    821 Carver St, Winter Park, FL 32789
  • 1470 Place Picardy, Winter Park, FL 32789
    1470 Place Picardy, Winter Park, FL 32789
    /2

    $1,625,000 Sold Jun 12, 2025

    1470 Place Picardy, Winter Park, FL 32789

    • 5 Beds
    • 6 Baths
    • 4,227 Sq Ft
    • Built 2003

    Last Sold Summary

    • 17% Below List Price
    • $384/SF
    • 95 Days On Market

    Current Estimated Value $1,723,329

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

    1470 Place Picardy, Winter Park, FL 32789
  • 764 Baffie Ave, Winter Park, FL 32789
    764 Baffie Ave, Winter Park, FL 32789
    /2

    $335,000 Sold Mar 04, 2025

    764 Baffie Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft
    • Built 1954

    Last Sold Summary

    • 12% Below List Price
    • $310/SF
    • 70 Days On Market

    Current Estimated Value $342,591

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    764 Baffie Ave, Winter Park, FL 32789
  • 1151 Wildmeadow Run, Winter Park, FL 32792
    1151 Wildmeadow Run, Winter Park, FL 32792
    /2

    $750,000 Sold Jun 27, 2025

    1151 Wildmeadow Run, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,196 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Below List Price
    • $342/SF
    • 22 Days On Market

    Current Estimated Value $749,452

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

    1151 Wildmeadow Run, Winter Park, FL 32792
  • 200 Saint Andrews Blvd Unit 1901, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 1901, Winter Park, FL 32792
    /2

    $180,000 Sold Sep 18, 2025

    200 Saint Andrews Blvd Unit 1901, Winter Park, FL 32792

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

    Last Sold Summary

    • 10% Below List Price
    • $182/SF
    • 8 Days On Market

    Current Estimated Value $183,750

    Last Listing Agent peggy amos FANNIE HILLMAN & ASSOCIATES

    200 Saint Andrews Blvd Unit 1901, Winter Park, FL 32792
  • 1681 Woodland Ave, Winter Park, FL 32789
    1681 Woodland Ave, Winter Park, FL 32789
    /2

    $750,000 Sold Nov 19, 2025

    1681 Woodland Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 2,422 Sq Ft
    • Built 1953

    Last Sold Summary

    • $310/SF

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

    1681 Woodland Ave, Winter Park, FL 32789
  • 1937 Eland Ave, Winter Park, FL 32789
    1937 Eland Ave, Winter Park, FL 32789
    /2

    $460,000 Sold Mar 18, 2025

    1937 Eland Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1957

    Last Sold Summary

    • 3% Below List Price
    • $295/SF
    • 22 Days On Market

    Current Estimated Value $462,347

    Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

    1937 Eland Ave, Winter Park, FL 32789
  • 660 Osceola Ave Unit 104, Winter Park, FL 32789
    660 Osceola Ave Unit 104, Winter Park, FL 32789
    /2

    $2,250,000 Sold Jan 02, 2025

    660 Osceola Ave Unit 104, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 2,632 Sq Ft
    • Built 1999

    Last Sold Summary

    • 6% Below List Price
    • $855/SF
    • 21 Days On Market

    Current Estimated Value $2,175,955

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

    660 Osceola Ave Unit 104, Winter Park, FL 32789
  • 2100 Suffield Dr, Winter Park, FL 32792
    2100 Suffield Dr, Winter Park, FL 32792
    /2

    $550,000 Sold May 02, 2025

    2100 Suffield Dr, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,807 Sq Ft
    • Built 1960

    Last Sold Summary

    • 15% Below List Price
    • $304/SF
    • 67 Days On Market

    Current Estimated Value $540,808

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    2100 Suffield Dr, Winter Park, FL 32792
  • 2024 Linden Rd, Winter Park, FL 32792
    2024 Linden Rd, Winter Park, FL 32792
    /2

    $420,000 Sold May 20, 2025

    2024 Linden Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 1972

    Last Sold Summary

    • 1% Above List Price
    • $224/SF
    • 3 Days On Market

    Current Estimated Value $425,902

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

    2024 Linden Rd, Winter Park, FL 32792
  • 1840 Laurel Rd, Winter Park, FL 32789
    1840 Laurel Rd, Winter Park, FL 32789
    /2

    $705,000 Sold Jul 03, 2025

    1840 Laurel Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 2,245 Sq Ft
    • Built 1957

    Last Sold Summary

    • 9% Below List Price
    • $314/SF
    • 13 Days On Market

    Current Estimated Value $733,346

    Last Listing Agent Julie Glass KEYSEEKERS REAL ESTATE

    1840 Laurel Rd, Winter Park, FL 32789
  • 955 Minnesota Ave, Winter Park, FL 32789
    955 Minnesota Ave, Winter Park, FL 32789
    /2

    $458,000 Sold Jul 31, 2025

    955 Minnesota Ave, Winter Park, FL 32789

    • 3 Beds
    • 1 Bath
    • 1,349 Sq Ft
    • Built 1940

    Last Sold Summary

    • 4% Below List Price
    • $340/SF
    • 4 Days On Market

    Current Estimated Value $460,972

    Last Listing Agent Cora Johnson WYNNMORE REALTY LLC

    955 Minnesota Ave, Winter Park, FL 32789
  • 1030 N Lakemont Ave, Winter Park, FL 32792
    1030 N Lakemont Ave, Winter Park, FL 32792
    /2

    $418,000 Sold Dec 22, 2025

    1030 N Lakemont Ave, Winter Park, FL 32792

    • 3 Beds
    • 1.5 Baths
    • 1,050 Sq Ft
    • Built 1959

    Last Sold Summary

    • 2% Below List Price
    • $398/SF
    • 3 Days On Market

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

    1030 N Lakemont Ave, Winter Park, FL 32792
  • 1181 Via Capri, Winter Park, FL 32789
    1181 Via Capri, Winter Park, FL 32789
    /2

    $1,700,000 Sold Oct 29, 2025

    1181 Via Capri, Winter Park, FL 32789

    • Land
    • 0.3 Acre
    • $5,666,667 per Acre

    Last Sold Summary

    • 16 Days On Market

    Last Listing Agent Brad Grosberg PHIL KEAN REAL ESTATE LLC

    1181 Via Capri, Winter Park, FL 32789

Showing Results 641 - 680, Page 17 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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