1,107

Recently Sold Winter Park, FL Homes

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    $3,978,550

    Sold May 18, 2026

    2020 Via Tuscany, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 4,665 Sq Ft
    • Built 2026

    Last Sold Summary

    • 5% Below List Price
    • $853/SF
    • 4 Days On Market

    Current Estimated Value $3,969,121

    Last Listing Agent Mauro Costa WILLIAM RAVEIS - FLORIDA LLC

    2020 Via Tuscany, Winter Park, FL 32789
  • /2

    $920,000

    Sold Jul 22, 2026

    250 Cortland Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 2,114 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $435/SF
    • 73 Days On Market

    Current Estimated Value $966,752

    Last Listing Agent James Ferngren CREEGAN GROUP

    250 Cortland Ave, Winter Park, FL 32789
  • /2

    $819,000

    Sold Oct 31, 2025

    734 Maryland Ave, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 1926

    Last Sold Summary

    • 3% Below List Price
    • $655/SF
    • 44 Days On Market

    Current Estimated Value $846,586

    Last Listing Agent Michael Domi COMPASS FLORIDA LLC

    734 Maryland Ave, Winter Park, FL 32789
  • /2

    $715,000

    Sold Sep 26, 2025

    438 W Swoope Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft
    • Built 2014

    Last Sold Summary

    • 9% Below List Price
    • $275/SF
    • 46 Days On Market

    Current Estimated Value $749,774

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    438 W Swoope Ave, Winter Park, FL 32789
  • /2

    $287,500

    Sold Jun 12, 2026

    119 Oak Grove Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,134 Sq Ft
    • Built 1994

    Last Sold Summary

    • 1% Above List Price
    • $254/SF
    • 2 Days On Market

    Current Estimated Value $291,044

    Last Listing Agent Lorena Ortega INT'L PROFESSIONAL REALTY INC

    119 Oak Grove Rd, Winter Park, FL 32789
  • /2

    $410,000

    Sold Dec 02, 2025

    2464 Lotafun Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 1,804 Sq Ft
    • Built 1951

    Last Sold Summary

    • 9% Below List Price
    • $227/SF
    • 112 Days On Market

    Current Estimated Value $429,664

    Last Listing Agent Irina Paul FUTURE HOME REALTY INC

    2464 Lotafun Ave, Winter Park, FL 32789
  • /2

    $755,000

    Sold Dec 30, 2025

    2074 Laurelwood Way, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,192 Sq Ft
    • Built 2019

    Last Sold Summary

    • 4% Below List Price
    • $344/SF
    • 8 Days On Market

    Current Estimated Value $767,247

    Last Listing Agent Janki Thakkar DJ & LINDSEY REAL ESTATE

    2074 Laurelwood Way, Winter Park, FL 32792
  • /2

    $415,000

    Sold Dec 25, 2025

    1921 Taylor Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,322 Sq Ft
    • Built 1956

    Last Sold Summary

    • 1% Above List Price
    • $314/SF
    • 167 Days On Market

    Current Estimated Value $417,333

    Last Listing Agent Brianna Perez Montalvo EXP REALTY LLC

    1921 Taylor Ave, Winter Park, FL 32792
  • /2

    $1,000,000

    Sold May 21, 2026

    101 S New York Ave Unit 302, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 3,174 Sq Ft
    • Built 2009

    Last Sold Summary

    • 39% Below List Price
    • $315/SF
    • 36 Days On Market

    Current Estimated Value $1,291,073

    Last Listing Agent Julie Scott COLDWELL BANKER REALTY

    101 S New York Ave Unit 302, Winter Park, FL 32789
  • /2

    $415,000

    Sold Jul 10, 2026

    1354 Tierra Cir, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,827 Sq Ft
    • Built 1969

    Last Sold Summary

    • 14% Below List Price
    • $227/SF
    • 512 Days On Market

    Current Estimated Value $441,732

    Last Listing Agent Carl Mataushek REAL ESTATE FIRM OF ORLANDO

    1354 Tierra Cir, Winter Park, FL 32792
  • /2

    $270,000

    Sold Oct 15, 2025

    1871 Casselwood St, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,616 Sq Ft
    • Built 1988

    Last Sold Summary

    • 16% Below List Price
    • $167/SF
    • 33 Days On Market

    Current Estimated Value $410,721

    Last Listing Agent Nicholas Zervos LPT REALTY, LLC

    1871 Casselwood St, Winter Park, FL 32792
  • /2

    $1,100,000

    Sold Jun 16, 2026

    2922 Reef Knot Place, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,153 Sq Ft
    • Built 2019

    Last Sold Summary

    • 23% Below List Price
    • $349/SF
    • 328 Days On Market

    Current Estimated Value $1,163,775

    Last Listing Agent Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO

    2922 Reef Knot Place, Winter Park, FL 32792
  • /2

    $455,000

    Sold Oct 27, 2025

    2405 Firstlight Way, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft
    • Built 2019

    Last Sold Summary

    • 3% Below List Price
    • $232/SF
    • 91 Days On Market

    Current Estimated Value $455,850

    Last Listing Agent Carmen Acosta BP REALTY

    2405 Firstlight Way, Winter Park, FL 32792
  • /2

    $412,000

    Sold Aug 22, 2025

    535 N Interlachen Ave Unit 107, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,088 Sq Ft
    • Built 1972

    Last Sold Summary

    • 18% Below List Price
    • $379/SF
    • 127 Days On Market

    Current Estimated Value $438,171

    Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

    535 N Interlachen Ave Unit 107, Winter Park, FL 32789
  • /2

    $1,785,000

    Sold Sep 11, 2025

    1640 Mayfield Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,907 Sq Ft
    • Built 1953

    Last Sold Summary

    • 1% Below List Price
    • $614/SF
    • 29 Days On Market

    Current Estimated Value $1,793,206

    Last Listing Agent Beverly Brown RE/MAX PRIME PROPERTIES

    1640 Mayfield Ave, Winter Park, FL 32789
  • /2

    $2,490,000

    Sold Jul 30, 2026

    1300 Mayfield Ave, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,389 Sq Ft
    • Built 1958

    Last Sold Summary

    • 13% Below List Price
    • $567/SF
    • 88 Days On Market

    Current Estimated Value $2,509,580

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1300 Mayfield Ave, Winter Park, FL 32789
  • /2

    $520,000

    Sold Nov 24, 2025

    3025 Northwood Blvd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft
    • Built 1953

    Last Sold Summary

    • 5% Below List Price
    • $336/SF
    • 2 Days On Market

    Current Estimated Value $541,915

    Last Listing Agent Alie Gattis MAINFRAME REAL ESTATE

    3025 Northwood Blvd, Winter Park, FL 32789
  • /2

    $612,500

    Sold Jun 16, 2026

    259 E Canton Ave Unit 259, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft
    • Built 1971

    Last Sold Summary

    • 6% Below List Price
    • $589/SF
    • 45 Days On Market

    Current Estimated Value $616,277

    Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

    259 E Canton Ave Unit 259, Winter Park, FL 32789
  • /2

    $398,000

    Sold Nov 24, 2025

    3529 Australian Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,255 Sq Ft
    • Built 1963

    Last Sold Summary

    • $317/SF
    • 8 Days On Market

    Current Estimated Value $391,124

    Last Listing Agent Lori Hoover EXP REALTY LLC

    3529 Australian Cir, Winter Park, FL 32792
  • /2

    $405,000

    Sold Sep 12, 2025

    5234 Ohio St, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,226 Sq Ft
    • Built 1973

    Last Sold Summary

    • 6% Above List Price
    • $330/SF
    • 15 Days On Market

    Current Estimated Value $385,728

    Last Listing Agent Emily Nickley MARKET CONNECT REALTY LLC

    5234 Ohio St, Winter Park, FL 32792
  • /2

    $502,000

    Sold Oct 30, 2025

    2308 Mulbry Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft
    • Built 1952

    Last Sold Summary

    • 9% Below List Price
    • $352/SF
    • 4 Days On Market

    Current Estimated Value $519,138

    Last Listing Agent Daniel Sposato BALDWIN PARK REALTY LLC

    2308 Mulbry Dr, Winter Park, FL 32789
  • /2

    $1,318,000

    Sold Oct 31, 2025

    1741 Palmer Ave, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 2,351 Sq Ft
    • Built 2013

    Last Sold Summary

    • 17% Below List Price
    • $561/SF
    • 143 Days On Market

    Current Estimated Value $1,351,429

    Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1741 Palmer Ave, Winter Park, FL 32789
  • /2

    $630,000

    Sold Feb 25, 2026

    2805 Northwood Blvd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft
    • Built 1953

    Last Sold Summary

    • 4% Below List Price
    • $503/SF
    • 6 Days On Market

    Current Estimated Value $649,424

    Last Listing Agent Daniel Francoforte LIVE OAK EQUITIES

    2805 Northwood Blvd, Winter Park, FL 32789
  • /2

    $255,000

    Sold Aug 21, 2025

    2398 Dominica Run, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • Built 1979

    Last Sold Summary

    • 4% Below List Price
    • $198/SF
    • 7 Days On Market

    Current Estimated Value $262,225

    Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

    2398 Dominica Run, Winter Park, FL 32792
  • /2

    $68,000

    Sold Mar 18, 2026

    282 Scottsdale Square Unit 282, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 756 Sq Ft
    • Built 1974

    Last Sold Summary

    • 14% Below List Price
    • $90/SF
    • 2 Days On Market

    Current Estimated Value $70,534

    Last Listing Agent Karina Mendez CHARLES RUTENBERG REALTY ORLANDO

    282 Scottsdale Square Unit 282, Winter Park, FL 32792
  • /2

    $189,900

    Sold Apr 15, 2026

    102 Lewfield Cir Unit 102, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 953 Sq Ft
    • Built 1973

    Last Sold Summary

    • $199/SF
    • 11 Days On Market

    Current Estimated Value $186,990

    Last Listing Agent Jennifer Thompson UNITED REALTY GROUP INC

    102 Lewfield Cir Unit 102, Winter Park, FL 32792
  • /2

    $315,000

    Sold Jan 27, 2026

    5475 Bracken Ct, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 1,499 Sq Ft
    • Built 1984

    Last Sold Summary

    • $210/SF
    • 11 Days On Market

    Current Estimated Value $317,631

    Last Listing Agent Jean Scott KELLER WILLIAMS ADVANTAGE REALTY

    5475 Bracken Ct, Winter Park, FL 32792
  • /2

    $510,000

    Sold Oct 29, 2025

    8136 Lazy Bear Ln, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,843 Sq Ft
    • Built 2013

    Last Sold Summary

    • 3% Below List Price
    • $277/SF
    • 53 Days On Market

    Current Estimated Value $510,030

    Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    8136 Lazy Bear Ln, Winter Park, FL 32792
  • /2

    $382,575

    Sold Nov 03, 2025

    1001 Early Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,222 Sq Ft
    • Built 1956

    Last Sold Summary

    • 4% Below List Price
    • $313/SF
    • 37 Days On Market

    Current Estimated Value $397,139

    Last Listing Agent John Neusaenger COLDWELL BANKER REALTY

    1001 Early Ave, Winter Park, FL 32789
  • /2

    $425,000

    Sold Oct 06, 2025

    524 Byron Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,469 Sq Ft
    • Built 1957

    Last Sold Summary

    • 6% Below List Price
    • $289/SF
    • 21 Days On Market

    Current Estimated Value $436,448

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    524 Byron Rd, Winter Park, FL 32792
  • /2

    $262,500

    Sold Apr 09, 2026

    200 Saint Andrews Blvd Unit 2504, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,322 Sq Ft
    • Built 1970

    Last Sold Summary

    • 6% Below List Price
    • $199/SF
    • 25 Days On Market

    Current Estimated Value $264,495

    Last Listing Agent Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

    200 Saint Andrews Blvd Unit 2504, Winter Park, FL 32792
  • /2

    $195,000

    Sold Jan 02, 2026

    700 Melrose Ave Unit D21, Winter Park, FL 32789

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

    Last Sold Summary

    • 2% Below List Price
    • $224/SF
    • 57 Days On Market

    Current Estimated Value $195,869

    Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

    700 Melrose Ave Unit D21, Winter Park, FL 32789
  • /2

    $360,000

    Sold Apr 14, 2026

    1552 Florentino Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,682 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $214/SF
    • 76 Days On Market

    Current Estimated Value $356,612

    Last Listing Agent Nohora Gomez COLDWELL BANKER REALTY

    1552 Florentino Ln, Winter Park, FL 32792
  • /2

    $1,295,000

    Sold Aug 22, 2025

    1422 Via Sangro Place, Winter Park, FL 32792

    • 6 Beds
    • 4 Baths
    • 4,161 Sq Ft
    • Built 2015

    Last Sold Summary

    • $311/SF
    • 8 Days On Market

    Current Estimated Value $1,323,923

    Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

    1422 Via Sangro Place, Winter Park, FL 32792
  • /2

    $475,000

    Sold Mar 16, 2026

    2748 Lion Heart Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,502 Sq Ft
    • Built 1963

    Last Sold Summary

    • 5% Below List Price
    • $316/SF
    • 1 Day On Market

    Current Estimated Value $483,740

    Last Listing Agent Jean Scott KELLER WILLIAMS ADVANTAGE REALTY

    2748 Lion Heart Rd, Winter Park, FL 32792
  • /2

    $200,000

    Sold Dec 29, 2025

    200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,015 Sq Ft
    • Built 1970

    Last Sold Summary

    • 20% Below List Price
    • $197/SF
    • 218 Days On Market

    Current Estimated Value $197,823

    Last Listing Agent Lucy Gonzalez Zabala CHARLES RUTENBERG REALTY ORLANDO

    200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792
  • /2

    $200,000

    Sold Apr 10, 2026

    1996 Indiana Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 818 Sq Ft
    • Built 1938

    Last Sold Summary

    • 20% Below List Price
    • $244/SF
    • 78 Days On Market

    Current Estimated Value $253,952

    Last Listing Agent Mike Rance RE/MAX 200 REALTY

    1996 Indiana Ave, Winter Park, FL 32789
  • /2

    $170,000

    Sold Oct 13, 2025

    200 Saint Andrews Blvd Unit 2206, Winter Park, FL 32792

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

    Last Sold Summary

    • 15% Below List Price
    • $172/SF
    • 53 Days On Market

    Current Estimated Value $179,496

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    200 Saint Andrews Blvd Unit 2206, Winter Park, FL 32792
  • /2

    $370,000

    Sold Aug 29, 2025

    1021 Mare Bello Dr, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,730 Sq Ft
    • Built 1965

    Last Sold Summary

    • 10% Below List Price
    • $214/SF
    • 151 Days On Market

    Current Estimated Value $404,550

    Last Listing Agent Lori Hutchinson THE WILKINS WAY LLC

    1021 Mare Bello Dr, Winter Park, FL 32792
  • /2

    $622,500

    Sold Jan 06, 2026

    1835 Jessica Ct, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,637 Sq Ft
    • Built 1980

    Last Sold Summary

    • 4% Above List Price
    • $380/SF
    • 1 Day On Market

    Current Estimated Value $631,258

    Last Listing Agent Melissa Johnson EXP REALTY LLC

    1835 Jessica Ct, Winter Park, FL 32789

Showing Results 481 - 520, Page 13 of 18

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