1,143

Recently Sold Winter Park, FL Homes

Section Image
  • 300 Carolina Ave Unit 304, Winter Park, FL 32789
    300 Carolina Ave Unit 304, Winter Park, FL 32789
    /2

    $672,000 Sold Jun 27, 2025

    300 Carolina Ave Unit 304, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft
    • Built 1982

    Last Sold Summary

    • 2% Below List Price
    • $498/SF
    • 4 Days On Market

    Current Estimated Value $674,444

    Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

    300 Carolina Ave Unit 304, Winter Park, FL 32789
  • 1261 Burning Tree Ln, Winter Park, FL 32792
    1261 Burning Tree Ln, Winter Park, FL 32792
    /2

    $806,000 Sold Jul 21, 2025

    1261 Burning Tree Ln, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,223 Sq Ft
    • Built 1979

    Last Sold Summary

    • $363/SF
    • 4 Days On Market

    Current Estimated Value $787,783

    Last Listing Agent Adrienne Kane REAL BROKER, LLC

    1261 Burning Tree Ln, Winter Park, FL 32792
  • 524 Byron Rd, Winter Park, FL 32792
    524 Byron Rd, Winter Park, FL 32792
    /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 $422,976

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    524 Byron Rd, Winter Park, FL 32792
  • 2073 Shadyhill Terrace, Winter Park, FL 32792
    2073 Shadyhill Terrace, Winter Park, FL 32792
    /2

    $465,000 Sold Apr 17, 2025

    2073 Shadyhill Terrace, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,647 Sq Ft
    • Built 1988

    Last Sold Summary

    • 11% Below List Price
    • $282/SF
    • 80 Days On Market

    Current Estimated Value $472,307

    Last Listing Agent Holly Kroll KROLL REALTY GROUP

    2073 Shadyhill Terrace, Winter Park, FL 32792
  • 700 Melrose Ave Unit D21, Winter Park, FL 32789
    700 Melrose Ave Unit D21, Winter Park, FL 32789
    /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

    Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

    700 Melrose Ave Unit D21, Winter Park, FL 32789
  • 1422 Via Sangro Place, Winter Park, FL 32792
    1422 Via Sangro Place, 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 $1,294,617

    Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

    1422 Via Sangro Place, Winter Park, FL 32792
  • 3520 Wilde Ave, Winter Park, FL 32792
    3520 Wilde Ave, Winter Park, FL 32792
    /2

    $310,000 Sold Jul 17, 2025

    3520 Wilde Ave, Winter Park, FL 32792

    • Land
    • 1.01 Acres
    • $306,931 per Acre

    Last Sold Summary

    • 94 Days On Market

    Current Estimated Value $309,230

    Last Listing Agent Gwendolen Flynn COLDWELL BANKER RESIDENTIAL RE

    3520 Wilde Ave, Winter Park, FL 32792
  • 4029 Cool Water Ct Unit 2, Winter Park, FL 32792
    4029 Cool Water Ct Unit 2, Winter Park, FL 32792
    /2

    $525,000 Sold Jul 23, 2025

    4029 Cool Water Ct Unit 2, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 2,733 Sq Ft
    • Built 1979

    Last Sold Summary

    • 8% Below List Price
    • $192/SF
    • 104 Days On Market

    Current Estimated Value $536,780

    Last Listing Agent Cedrick Williams MAGNUS REALTY GROUP LLC

    4029 Cool Water Ct Unit 2, Winter Park, FL 32792
  • 141 S Phelps Ave, Winter Park, FL 32789
    141 S Phelps Ave, Winter Park, FL 32789
    /2

    $3,200,000 Sold Jul 31, 2025

    141 S Phelps Ave, Winter Park, FL 32789

    • 6 Beds
    • 5.5 Baths
    • 5,878 Sq Ft
    • Built 2006

    Last Sold Summary

    • 20% Below List Price
    • $544/SF
    • 63 Days On Market

    Current Estimated Value $3,193,541

    Last Listing Agent Donna Bryant COLDWELL BANKER RESIDENTIAL RE

    141 S Phelps Ave, Winter Park, FL 32789
  • 200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 2306, 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

    Last Listing Agent Lucy Gonzalez Zabala CHARLES RUTENBERG REALTY ORLANDO

    200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792
  • 200 Saint Andrews Blvd Unit 2206, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 2206, Winter Park, FL 32792
    /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 $173,519

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    200 Saint Andrews Blvd Unit 2206, Winter Park, FL 32792
  • 7783 Country Place Unit J2, Winter Park, FL 32792
    7783 Country Place Unit J2, Winter Park, FL 32792
    /2

    $260,000 Sold Apr 21, 2025

    7783 Country Place Unit J2, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,230 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Below List Price
    • $211/SF
    • 102 Days On Market

    Current Estimated Value $259,802

    Last Listing Agent Patty Munsey FANNIE HILLMAN & ASSOCIATES

    7783 Country Place Unit J2, Winter Park, FL 32792
  • 7344 Swallow Run Unit 7344, Winter Park, FL 32792
    7344 Swallow Run Unit 7344, Winter Park, FL 32792
    /2

    $125,000 Sold Jul 14, 2025

    7344 Swallow Run Unit 7344, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 802 Sq Ft
    • Built 1983

    Last Sold Summary

    • $156/SF
    • 5 Days On Market

    Current Estimated Value $127,929

    Last Listing Agent Merigan Barton DON HARKINS REALTY LLC

    7344 Swallow Run Unit 7344, Winter Park, FL 32792
  • 4309 Enright Ct, Winter Park, FL 32792
    4309 Enright Ct, Winter Park, FL 32792
    /2

    $500,000 Sold Apr 11, 2025

    4309 Enright Ct, Winter Park, FL 32792

    • 3 Beds
    • 3 Baths
    • 2,204 Sq Ft
    • Built 1985

    Last Sold Summary

    • $227/SF
    • 23 Days On Market

    Current Estimated Value $506,587

    Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

    4309 Enright Ct, Winter Park, FL 32792
  • 1021 Mare Bello Dr, Winter Park, FL 32792
    1021 Mare Bello Dr, 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 $398,081

    Last Listing Agent Lori Hutchinson THE WILKINS WAY LLC

    1021 Mare Bello Dr, Winter Park, FL 32792
  • 1835 Jessica Ct, Winter Park, FL 32789
    1835 Jessica Ct, Winter Park, FL 32789
    /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

    Last Listing Agent Melissa Johnson EXP REALTY LLC

    1835 Jessica Ct, Winter Park, FL 32789
  • 5110 N Woodcrest Dr, Winter Park, FL 32792
    5110 N Woodcrest Dr, Winter Park, FL 32792
    /2

    $350,000 Sold Dec 30, 2025

    5110 N Woodcrest Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,220 Sq Ft
    • Built 1969

    Last Sold Summary

    • 5% Below List Price
    • $287/SF
    • 26 Days On Market

    Last Listing Agent DANIELLE RICHARDSON LPT REALTY, LLC

    5110 N Woodcrest Dr, Winter Park, FL 32792
  • 5338 Tangerine Ave, Winter Park, FL 32792
    5338 Tangerine Ave, Winter Park, FL 32792
    /2

    $425,000 Sold Jan 08, 2026

    5338 Tangerine Ave, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,195 Sq Ft
    • Built 1976

    Last Sold Summary

    • 17% Below List Price
    • $194/SF
    • 224 Days On Market

    Last Listing Agent Mystique Barba CENTURY 21 CARIOTI

    5338 Tangerine Ave, Winter Park, FL 32792
  • 1915 S Lakemont Ave, Winter Park, FL 32792
    1915 S Lakemont Ave, Winter Park, FL 32792
    /2

    $800,000 Sold Mar 07, 2025

    1915 S Lakemont Ave, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 2,104 Sq Ft
    • Built 2024

    Last Sold Summary

    • 9% Below List Price
    • $380/SF
    • 149 Days On Market

    Current Estimated Value $809,960

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    1915 S Lakemont Ave, Winter Park, FL 32792
  • 490 Shoreview Ave, Winter Park, FL 32789
    490 Shoreview Ave, Winter Park, FL 32789
    /2

    $599,000 Sold Jul 25, 2025

    490 Shoreview Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 2,266 Sq Ft
    • Built 1935

    Last Sold Summary

    • $264/SF
    • 20 Days On Market

    Current Estimated Value $609,058

    Last Listing Agent Justin Harvey FLORIDA HOME TEAM REALTY LLC

    490 Shoreview Ave, Winter Park, FL 32789
  • 3310 Royal St, Winter Park, FL 32792
    3310 Royal St, Winter Park, FL 32792
    /2

    $265,000 Sold Sep 11, 2025

    3310 Royal St, Winter Park, FL 32792

    • 2 Beds
    • 1.5 Baths
    • 1,036 Sq Ft
    • Built 1982

    Last Sold Summary

    • 2% Below List Price
    • $256/SF
    • 116 Days On Market

    Current Estimated Value $266,209

    Last Listing Agent Kevin Schudel BUY IT INC

    3310 Royal St, Winter Park, FL 32792
  • 220 N Ranger Blvd, Winter Park, FL 32792
    220 N Ranger Blvd, Winter Park, FL 32792
    /2

    $530,000 Sold May 28, 2025

    220 N Ranger Blvd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft
    • Built 1963

    Last Sold Summary

    • $333/SF

    Current Estimated Value $522,486

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

    220 N Ranger Blvd, Winter Park, FL 32792
  • 801 Audubon Ln, Winter Park, FL 32789
    801 Audubon Ln, Winter Park, FL 32789
    /2

    $850,000 Sold Jan 08, 2026

    801 Audubon Ln, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 1952

    Last Sold Summary

    • $644/SF
    • 0 Days On Market

    Last Listing Agent Benjamin Cole, IV SOTERA LIVING

    801 Audubon Ln, Winter Park, FL 32789
  • 2498 Timberline Dr Unit 2498, Winter Park, FL 32792
    2498 Timberline Dr Unit 2498, Winter Park, FL 32792
    /2

    $230,000 Sold Apr 15, 2025

    2498 Timberline Dr Unit 2498, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,295 Sq Ft
    • Built 1980

    Last Sold Summary

    • 4% Below List Price
    • $178/SF
    • 52 Days On Market

    Current Estimated Value $233,820

    Last Listing Agent Melissa Woodman FANNIE HILLMAN & ASSOCIATES

    2498 Timberline Dr Unit 2498, Winter Park, FL 32792
  • 200 Saint Andrews Blvd Unit 601, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 601, Winter Park, FL 32792
    /2

    $165,000 Sold Oct 27, 2025

    200 Saint Andrews Blvd Unit 601, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 727 Sq Ft
    • Built 1970

    Last Sold Summary

    • 6% Below List Price
    • $227/SF
    • 106 Days On Market

    Current Estimated Value $160,445

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    200 Saint Andrews Blvd Unit 601, Winter Park, FL 32792
  • 624 Dunraven Dr, Winter Park, FL 32792
    624 Dunraven Dr, Winter Park, FL 32792
    /2

    $618,900 Sold Jul 11, 2025

    624 Dunraven Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,762 Sq Ft
    • Built 1963

    Last Sold Summary

    • 13% Below List Price
    • $351/SF
    • 65 Days On Market

    Current Estimated Value $621,274

    Last Listing Agent Brian Rotenberger COMPASS FLORIDA LLC

    624 Dunraven Dr, Winter Park, FL 32792
  • 1627 Elizabeths Walk, Winter Park, FL 32789
    1627 Elizabeths Walk, Winter Park, FL 32789
    /2

    $1,850,000 Sold Mar 14, 2025

    1627 Elizabeths Walk, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 3,846 Sq Ft
    • Built 2001

    Last Sold Summary

    • 7% Below List Price
    • $481/SF
    • 0 Days On Market

    Current Estimated Value $1,868,743

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1627 Elizabeths Walk, Winter Park, FL 32789
  • 1729 Golfside Dr, Winter Park, FL 32792
    1729 Golfside Dr, Winter Park, FL 32792
    /2

    $700,000 Sold Oct 20, 2025

    1729 Golfside Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,372 Sq Ft
    • Built 1981

    Last Sold Summary

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

    Current Estimated Value $700,986

    Last Listing Agent Rebecca Bininger Junod KELLER WILLIAMS WINTER PARK

    1729 Golfside Dr, Winter Park, FL 32792
  • 631 Symonds Ave, Winter Park, FL 32789
    631 Symonds Ave, Winter Park, FL 32789
    /2

    $475,000 Sold Oct 14, 2025

    631 Symonds Ave, Winter Park, FL 32789

    • Land
    • 0.13 Acre
    • $3,653,846 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 147 Days On Market

    Current Estimated Value $474,833

    Last Listing Agent Emily Williams FANNIE HILLMAN & ASSOCIATES

    631 Symonds Ave, Winter Park, FL 32789
  • 1268 Preserve Point Dr, Winter Park, FL 32789
    1268 Preserve Point Dr, Winter Park, FL 32789
    /2

    $2,325,000 Sold Nov 10, 2025

    1268 Preserve Point Dr, Winter Park, FL 32789

    • 4 Beds
    • 4 Baths
    • 4,315 Sq Ft
    • Built 2006

    Last Sold Summary

    • 1% Below List Price
    • $539/SF
    • 2 Days On Market

    Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

    1268 Preserve Point Dr, Winter Park, FL 32789
  • 185 Scottsdale Square Unit F185, Winter Park, FL 32792
    185 Scottsdale Square Unit F185, Winter Park, FL 32792
    /2

    $82,000 Sold Jun 20, 2025

    185 Scottsdale Square Unit F185, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft
    • Built 1974

    Last Sold Summary

    • 25% Below List Price
    • $80/SF
    • 13 Days On Market

    Current Estimated Value $83,401

    Last Listing Agent Erin Baker FANNIE HILLMAN & ASSOCIATES

    185 Scottsdale Square Unit F185, Winter Park, FL 32792
  • 7266 Swallow Run, Winter Park, FL 32792
    7266 Swallow Run, Winter Park, FL 32792
    /2

    $155,000 Sold Jun 30, 2025

    7266 Swallow Run, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 756 Sq Ft
    • Built 1985

    Last Sold Summary

    • 15% Below List Price
    • $205/SF
    • 107 Days On Market

    Current Estimated Value $151,821

    Last Listing Agent Jessica Riccardo TRINITY REAL ESTATE SALES LLC

    7266 Swallow Run, Winter Park, FL 32792
  • 1640 Cypress Point Ln, Winter Park, FL 32792
    1640 Cypress Point Ln, Winter Park, FL 32792
    /2

    $655,000 Sold Sep 12, 2025

    1640 Cypress Point Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft
    • Built 1980

    Last Sold Summary

    • 8% Below List Price
    • $384/SF
    • 23 Days On Market

    Current Estimated Value $658,991

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    1640 Cypress Point Ln, Winter Park, FL 32792
  • 3520 Balsam Dr, Winter Park, FL 32792
    3520 Balsam Dr, Winter Park, FL 32792
    /2

    $428,000 Sold Jul 02, 2025

    3520 Balsam Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,468 Sq Ft
    • Built 1965

    Last Sold Summary

    • 1% Above List Price
    • $292/SF
    • 22 Days On Market

    Current Estimated Value $427,217

    Last Listing Agent Cece Wong EXP REALTY LLC

    3520 Balsam Dr, Winter Park, FL 32792
  • 1807 Yorkshire Dr, Winter Park, FL 32792
    1807 Yorkshire Dr, Winter Park, FL 32792
    /2

    $450,000 Sold May 29, 2025

    1807 Yorkshire Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,672 Sq Ft
    • Built 1956

    Last Sold Summary

    • 13% Below List Price
    • $269/SF
    • 26 Days On Market

    Last Listing Agent Carla Stanton MAINFRAME REAL ESTATE

    1807 Yorkshire Dr, Winter Park, FL 32792
  • 26 Stymie Place, Winter Park, FL 32789
    26 Stymie Place, Winter Park, FL 32789
    /2

    $1,379,900 Sold Feb 10, 2025

    26 Stymie Place, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,252 Sq Ft
    • Built 2025

    Last Sold Summary

    • $424/SF
    • 38 Days On Market

    Current Estimated Value $1,355,878

    Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

    26 Stymie Place, Winter Park, FL 32789
  • 3132 Nicholson Dr, Winter Park, FL 32792
    3132 Nicholson Dr, Winter Park, FL 32792
    /2

    $447,500 Sold Apr 30, 2025

    3132 Nicholson Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,537 Sq Ft
    • Built 1977

    Last Sold Summary

    • 3% Below List Price
    • $291/SF
    • 14 Days On Market

    Current Estimated Value $450,039

    Last Listing Agent Vince Indiveri LIVE FLORIDA NOW LLC

    3132 Nicholson Dr, Winter Park, FL 32792
  • 1904 Houndslake Dr, Winter Park, FL 32792
    1904 Houndslake Dr, Winter Park, FL 32792
    /2

    $485,000 Sold Mar 03, 2025

    1904 Houndslake Dr, Winter Park, FL 32792

    • 3 Beds
    • 3 Baths
    • 1,840 Sq Ft
    • Built 1982

    Last Sold Summary

    • 3% Below List Price
    • $264/SF
    • 11 Days On Market

    Current Estimated Value $474,876

    Last Listing Agent Anna Lohr URBANISTA BROKERS

    1904 Houndslake Dr, Winter Park, FL 32792
  • 2739 Amsden Rd, Winter Park, FL 32792
    2739 Amsden Rd, Winter Park, FL 32792
    /2

    $510,000 Sold Aug 29, 2025

    2739 Amsden Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,877 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Above List Price
    • $272/SF
    • 6 Days On Market

    Current Estimated Value $502,187

    Last Listing Agent D'Anne Mica FANNIE HILLMAN & ASSOCIATES

    2739 Amsden Rd, Winter Park, FL 32792
  • 4026 Tenita Dr, Winter Park, FL 32792
    4026 Tenita Dr, Winter Park, FL 32792
    /2

    $470,000 Sold Aug 18, 2025

    4026 Tenita Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,122 Sq Ft
    • Built 1979

    Last Sold Summary

    • 16% Below List Price
    • $221/SF
    • 226 Days On Market

    Current Estimated Value $478,540

    Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

    4026 Tenita Dr, Winter Park, FL 32792

Showing Results 521 - 560, Page 14 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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