1,107

Recently Sold Winter Park, FL Homes

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  • /2

    $230,000

    Sold Jun 09, 2026

    1250 S Denning Dr Unit 117, Winter Park, FL 32789

    • 2 Beds
    • 1.5 Baths
    • 908 Sq Ft
    • Built 1967

    Last Sold Summary

    • 4% Below List Price
    • $253/SF
    • 11 Days On Market

    Current Estimated Value $231,487

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

    1250 S Denning Dr Unit 117, Winter Park, FL 32789
  • /2

    $625,000

    Sold Jun 11, 2026

    962 Aragon Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1996

    Last Sold Summary

    • 4% Above List Price
    • $372/SF
    • 1 Day On Market

    Current Estimated Value $616,534

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    962 Aragon Ave, Winter Park, FL 32789
  • /2

    $470,000

    Sold Jul 08, 2026

    1511 Gladiolas Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,594 Sq Ft
    • Built 1979

    Last Sold Summary

    • $295/SF
    • 2 Days On Market

    Current Estimated Value $467,189

    Last Listing Agent Richard Aybar KELLER WILLIAMS ADVANTAGE III

    1511 Gladiolas Dr, Winter Park, FL 32792
  • /2

    $285,000

    Sold Jun 29, 2026

    3159 Greenwood St, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,241 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Below List Price
    • $230/SF
    • 4 Days On Market

    Current Estimated Value $286,435

    Last Listing Agent Joe Pietzyk GLOBAL PROPERTIES SALES/MGMT

    3159 Greenwood St, Winter Park, FL 32792
  • /2

    $1,395,000

    Sold Jun 30, 2026

    2408 Lafayette Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,838 Sq Ft
    • Built 2024

    Last Sold Summary

    • 7% Below List Price
    • $492/SF
    • 60 Days On Market

    Current Estimated Value $1,547,410

    Last Listing Agent Matthew Burks CORCORAN PREMIER REALTY

    2408 Lafayette Ave, Winter Park, FL 32789
  • /2

    $103,000

    Sold May 26, 2026

    3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,066 Sq Ft
    • Built 1974

    Last Sold Summary

    • 13% Below List Price
    • $97/SF
    • 145 Days On Market

    Last Listing Agent Amin Abraham FLORIDA REALTY INVESTMENTS

    3057 Aaron Burr Ave Unit 1, 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 $455,463

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

    513 Dunraven Dr, 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
  • /2

    $475,000

    Sold Jun 17, 2026

    1036 Aragon Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,073 Sq Ft
    • Built 1957

    Last Sold Summary

    • 10% Below List Price
    • $443/SF
    • 108 Days On Market

    Current Estimated Value $481,222

    Last Listing Agent Tim Veigle WATSON REALTY CORP

    1036 Aragon 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 $3,215,813

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

    1610 Oakhurst Ave, Winter Park, FL 32789
  • /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 $352,222

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

    3103 Ash Park Loop, Winter Park, FL 32792
  • /2

    $2,650,000

    Sold Jul 31, 2026

    1630 Lasbury Ave, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 4,917 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $539/SF
    • 49 Days On Market

    Current Estimated Value $2,666,969

    Last Listing Agent Teresa Chris Harralson COMPASS FLORIDA, LLC

    1630 Lasbury Ave, Winter Park, FL 32789
  • /2

    $183,000

    Sold Apr 03, 2026

    2529 Windward Way, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Built 1977

    Last Sold Summary

    • 12% Below List Price
    • $166/SF
    • 4 Days On Market

    Current Estimated Value $280,111

    Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

    2529 Windward Way, Winter Park, FL 32792
  • /2

    $1,500,000

    Sold Apr 15, 2026

    132 Burks Cir, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,022 Sq Ft
    • Built 1997

    Last Sold Summary

    • 10% Below List Price
    • $496/SF
    • 130 Days On Market

    Current Estimated Value $1,494,618

    Last Listing Agent Ivey Geisler KELLER WILLIAMS REALTY AT THE PARKS

    132 Burks Cir, Winter Park, FL 32789
  • /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

    Current Estimated Value $1,508,014

    Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

    1460 Via Sangro Place, Winter Park, FL 32792
  • /2

    $234,000

    Sold Feb 24, 2026

    151 N Orlando Ave Unit 204, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 710 Sq Ft
    • Built 1960

    Last Sold Summary

    • 6% Below List Price
    • $330/SF
    • 244 Days On Market

    Current Estimated Value $231,320

    Last Listing Agent Eddie Cooper MAINFRAME REAL ESTATE

    151 N Orlando Ave Unit 204, Winter Park, FL 32789
  • /2

    $167,000

    Sold Jul 02, 2026

    3217 Oak Lawn Place Unit 211, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,117 Sq Ft
    • Built 1984

    Last Sold Summary

    • 14% Below List Price
    • $150/SF
    • 88 Days On Market

    Current Estimated Value $171,880

    Last Listing Agent Abby Yelken SHORES REAL ESTATE

    3217 Oak Lawn Place Unit 211, Winter Park, FL 32792
  • /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

    Current Estimated Value $851,267

    Last Listing Agent Kristen Hamilton LOMBARDO TEAM REAL ESTATE LLC

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

    $425,000

    Sold Aug 29, 2025

    1871 Staunton Ave, Winter Park, FL 32789

    • Land
    • 13,939 Sq Ft
    • $1,328,125 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 3 Days On Market

    Current Estimated Value $425,618

    Last Listing Agent Greg Staker WATSON REALTY CORP.

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

    $475,000

    Sold Sep 19, 2025

    1414 Bessmor Rd, Winter Park, FL 32789

    • Land
    • 6,969 Sq Ft
    • $2,968,750 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 22 Days On Market

    Current Estimated Value $506,032

    Last Listing Agent Miranda Azer PARKVIEW REAL ESTATE

    1414 Bessmor Rd, Winter Park, FL 32789
  • /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

    Current Estimated Value $404,586

    Last Listing Agent Gregory Roberts LPT REALTY LLC

    3214 Lowndes Dr, Winter Park, FL 32792
  • /2

    $395,000

    Sold Feb 11, 2026

    1362 Tierra Cir, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,179 Sq Ft
    • Built 1969

    Last Sold Summary

    • 10% Below List Price
    • $181/SF
    • 107 Days On Market

    Current Estimated Value $405,116

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    1362 Tierra Cir, Winter Park, FL 32792
  • /2

    $215,000

    Sold Jun 01, 2026

    5130 Lazy Oaks Dr, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1982

    Last Sold Summary

    • 12% Below List Price
    • $213/SF
    • 43 Days On Market

    Current Estimated Value $219,673

    Last Listing Agent Jacob Zampella CHARLES RUTENBERG REALTY ORLANDO

    5130 Lazy Oaks Dr, Winter Park, FL 32792
  • /2

    $1,025,000

    Sold Jan 27, 2026

    1840 Shiloh Ln, Winter Park, FL 32789

    • Land
    • 11,761 Sq Ft
    • $3,796,296 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $1,028,361

    Last Listing Agent Gwyn Clark FANNIE HILLMAN & ASSOCIATES

    1840 Shiloh Ln, Winter Park, FL 32789
  • /2

    $570,000

    Sold Jan 02, 2026

    640 Killarney Bay Ct Unit 4, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 1,718 Sq Ft
    • Built 1986

    Last Sold Summary

    • 22% Below List Price
    • $332/SF
    • 231 Days On Market

    Current Estimated Value $494,767

    Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

    640 Killarney Bay Ct Unit 4, 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

    Current Estimated Value $705,884

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    786 Antonette Ave, Winter Park, FL 32789
  • /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

    Current Estimated Value $374,957

    Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

    2828 Whispering Way, Winter Park, FL 32792
  • /2

    $2,000,000

    Sold Jul 24, 2026

    1624 Barcelona Way, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 3,818 Sq Ft
    • Built 1972

    Last Sold Summary

    • 16% Below List Price
    • $524/SF
    • 211 Days On Market

    Current Estimated Value $2,163,383

    Last Listing Agent Jan Walker PREMIER SOTHEBY'S INTL. REALTY

    1624 Barcelona Way, Winter Park, FL 32789
  • /2

    $824,500

    Sold Aug 10, 2026

    439 N Capen Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,861 Sq Ft
    • Built 2017

    Last Sold Summary

    • 3% Below List Price
    • $443/SF
    • 3 Days On Market

    Current Estimated Value $861,008

    Last Listing Agent Brian Rotenberger COMPASS FLORIDA LLC

    439 N Capen Ave, Winter Park, FL 32789
  • /2

    $401,000

    Sold Jun 09, 2026

    3330 Coleus Ct, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,988 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Below List Price
    • $202/SF
    • 50 Days On Market

    Current Estimated Value $403,177

    Last Listing Agent Raquel Littlejohn MAINSTAY BROKERAGE LLC

    3330 Coleus Ct, Winter Park, FL 32792
  • /2

    $250,000

    Sold Jan 16, 2026

    1605 Puritan Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,285 Sq Ft
    • Built 1963

    Last Sold Summary

    • 28% Below List Price
    • $195/SF
    • 26 Days On Market

    Current Estimated Value $386,444

    Last Listing Agent Denise San Miguel REALTY LYNK INC

    1605 Puritan Ave, Winter Park, FL 32792
  • /2

    $349,000

    Sold Mar 11, 2026

    5202 Lake Howell Rd, Winter Park, FL 32792

    • 3 Beds
    • 1.5 Baths
    • 1,112 Sq Ft
    • Built 1957

    Last Sold Summary

    • $314/SF
    • 5 Days On Market

    Current Estimated Value $345,956

    Last Listing Agent Crystal Vann CHARLES RUTENBERG REALTY ORLANDO

    5202 Lake Howell Rd, Winter Park, FL 32792
  • /23

    $129,000

    Sold Aug 10, 2026

    283 Lewfield Cir, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 678 Sq Ft
    • Built 1973

    Last Sold Summary

    • 9% Below List Price
    • $190/SF
    • 9 Days On Market

    Current Estimated Value $141,142

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    283 Lewfield Cir, Winter Park, FL 32792
  • /2

    $1,000,000

    Sold Jun 26, 2026

    520 Fitzwalter Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,111 Sq Ft
    • Built 2022

    Last Sold Summary

    • $474/SF
    • 5 Days On Market

    Current Estimated Value $987,891

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    520 Fitzwalter Dr, Winter Park, FL 32792
  • /2

    $470,000

    Sold Jun 05, 2026

    3167 Ash Park Loop, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,906 Sq Ft
    • Built 1988

    Last Sold Summary

    • $247/SF
    • 3 Days On Market

    Current Estimated Value $468,874

    Last Listing Agent Ken Pozek REAL BROKER, LLC

    3167 Ash Park Loop, 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 $186,152

    Last Listing Agent peggy amos FANNIE HILLMAN & ASSOCIATES

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

    $680,000

    Sold Jul 17, 2026

    1701 Goodrich Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • Built 1950

    Last Sold Summary

    • 8% Below List Price
    • $445/SF
    • 46 Days On Market

    Current Estimated Value $711,811

    Last Listing Agent Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

    1701 Goodrich 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

    Current Estimated Value $810,802

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

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

    $2,150,000

    Sold Jul 14, 2026

    800 Juanita Rael, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 4,021 Sq Ft
    • Built 1961

    Last Sold Summary

    • 7% Below List Price
    • $535/SF
    • 56 Days On Market

    Current Estimated Value $2,231,624

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

    800 Juanita Rael, Winter Park, FL 32789
  • /74

    $310,000

    Sold Feb 03, 2026

    1733 Winter Green Blvd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft
    • Built 1987

    Last Sold Summary

    • 11% Below List Price
    • $200/SF
    • 10 Days On Market

    Current Estimated Value $307,141

    Last Listing Agent TJ TAMARA FISHER Compass Florida LLC

    1733 Winter Green Blvd, Winter Park, FL 32792

Showing Results 601 - 640, Page 16 of 18

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