Recently Sold Winter Park Homes

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  $2,700,000 Sold Oct 02, 2025

  1445 Holts Grove Cir, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,489 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Above List Price
  • $601/SF
  • 2 Days On Market

  Current Estimated Value $2,654,470

  Last Listing Agent Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

  1445 Holts Grove Cir, Winter Park, FL 32789
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  $560,000 Sold Aug 20, 2025

  1901 Loch Berry Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft
  • Built 1957

  Last Sold Summary

  • 1% Below List Price
  • $394/SF
  • 7 Days On Market

  Current Estimated Value $537,712

  Last Listing Agent Monica Tipirneni FOLIO REALTY LLC

  1901 Loch Berry Rd, Winter Park, FL 32792
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  $916,000 Sold Jul 17, 2025

  609 Langholm Dr, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,981 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $462/SF
  • 8 Days On Market

  Current Estimated Value $904,622

  Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
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  $660,000 Sold Nov 17, 2025

  2421 Summerfield Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $293/SF
  • 6 Days On Market

  Current Estimated Value $650,425

  Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

  2421 Summerfield Rd, Winter Park, FL 32792
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  $498,000 Sold May 28, 2025

  808 Denton Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1961

  Last Sold Summary

  • $286/SF
  • 4 Days On Market

  Current Estimated Value $488,555

  Last Listing Agent Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

  808 Denton Rd, Winter Park, FL 32792
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  $3,485,000 Sold Oct 17, 2025

  2171 Forrest Rd, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,565 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $763/SF
  • 134 Days On Market

  Current Estimated Value $3,358,092

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

  2171 Forrest Rd, Winter Park, FL 32789
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  $420,000 Sold Sep 12, 2025

  1905 Diamond Dr, Orlando, FL 32807

  • 4 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $253/SF
  • 172 Days On Market

  Current Estimated Value $407,569

  Last Listing Agent John Walker, Jr HOUWZER INC

  1905 Diamond Dr, Orlando, FL 32807
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  $970,000 Sold Aug 12, 2025

  207 E Kings Way, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • Built 1951

  Last Sold Summary

  • $618/SF
  • 0 Days On Market

  Current Estimated Value $2,426,211

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  207 E Kings Way, Winter Park, FL 32789
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  $1,645,000 Sold May 20, 2025

  681 Balmoral Rd, Winter Park, FL 32789

  • Land
  • 1.14 Acres
  • $1,442,982 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 55 Days On Market

  Current Estimated Value $1,598,071

  Last Listing Agent Chris Burden EPIC REAL ESTATE ADVISORS LLC

  681 Balmoral Rd, Winter Park, FL 32789
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  $397,000 Sold Jul 01, 2025

  1109 Denton Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $321/SF
  • 83 Days On Market

  Current Estimated Value $389,199

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1109 Denton Rd, Winter Park, FL 32792
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  $3,200,000 Sold Apr 30, 2025

  1833 Loch Berry Rd, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,770 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $671/SF
  • 5 Days On Market

  Current Estimated Value $2,911,426

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1833 Loch Berry Rd, Winter Park, FL 32789
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  $228,000 Sold Jun 27, 2025

  1979 Staunton Ave, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Built 1948

  Last Sold Summary

  • 24% Below List Price
  • $310/SF
  • 16 Days On Market

  Current Estimated Value $226,368

  Last Listing Agent Michael Kara CORBELO LLC

  1979 Staunton Ave, Winter Park, FL 32789
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  $1,905,000 Sold Apr 10, 2026

  501 Henkel Cir, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,746 Sq Ft
  • Built 2009

  Last Sold Summary

  • 4% Above List Price
  • $509/SF
  • 4 Days On Market

  Current Estimated Value $2,182,635

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  501 Henkel Cir, Winter Park, FL 32789
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  $420,000 Sold Jan 15, 2026

  1847 Azalea Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 1,477 Sq Ft
  • Built 1961

  Last Sold Summary

  • $284/SF
  • 1 Day On Market

  Current Estimated Value $414,739

  Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

  1847 Azalea Ave, Winter Park, FL 32789
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  $199,900 Sold Nov 03, 2025

  2500 Lee Rd Unit 134, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Below List Price
  • $310/SF
  • 130 Days On Market

  Current Estimated Value $189,746

  Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

  2500 Lee Rd Unit 134, Winter Park, FL 32789
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  $172,000 Sold May 23, 2025

  700 Melrose Ave Unit E24, Winter Park, FL 32789

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

  Last Sold Summary

  • 14% Below List Price
  • $219/SF
  • 164 Days On Market

  Current Estimated Value $180,280

  Last Listing Agent Susan Dering HOMEVEST REALTY

  700 Melrose Ave Unit E24, Winter Park, FL 32789
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  $266,000 Sold Nov 19, 2025

  1500 Gay Rd Unit 9B, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $259/SF
  • 5 Days On Market

  Current Estimated Value $262,699

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 9B, Winter Park, FL 32789
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  $245,900 Sold Aug 11, 2025

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,132 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $217/SF
  • 2 Days On Market

  Current Estimated Value $253,849

  Last Listing Agent Matt Merdian MERDIAN REALTY LLC

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789
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  $725,000 Sold May 13, 2025

  1570 Grove Terrace, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft
  • Built 1991

  Last Sold Summary

  • $436/SF

  Current Estimated Value $753,538

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

  1570 Grove Terrace, Winter Park, FL 32789
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  $1,300,000 Sold Sep 22, 2025

  1371 Lyndale Blvd, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,714 Sq Ft
  • Built 1949

  Last Sold Summary

  • 4% Below List Price
  • $479/SF
  • 8 Days On Market

  Current Estimated Value $1,261,078

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
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  $400,000 Sold May 07, 2025

  2292 Hawick Ln, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,322 Sq Ft
  • Built 1958

  Last Sold Summary

  • $303/SF
  • 3 Days On Market

  Current Estimated Value $409,310

  Last Listing Agent Jason Alderman KELLER WILLIAMS ADVANTAGE REALTY

  2292 Hawick Ln, Winter Park, FL 32792
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  $1,002,000 Sold May 31, 2025

  1265 Park Pointe Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,295 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Above List Price
  • $437/SF
  • 4 Days On Market

  Current Estimated Value $1,006,067

  Last Listing Agent Frances Speights KELLER WILLIAMS ADVANTAGE III

  1265 Park Pointe Ln, Winter Park, FL 32789
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  $649,000 Sold Oct 17, 2025

  2304 Depauw Ave, Orlando, FL 32804

  • 3 Beds
  • 2.5 Baths
  • 1,668 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $389/SF
  • 199 Days On Market

  Current Estimated Value $652,000

  David Weekley Homes Central Living - Downtown

  2304 Depauw Ave, Orlando, FL 32804
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  $230,000 Sold Aug 29, 2025

  1500 Gay Rd Unit 7A, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Below List Price
  • $224/SF
  • 205 Days On Market

  Last Listing Agent Sean McCartney PRISTINE FLORIDA PROPERTIES LLC

  1500 Gay Rd Unit 7A, Winter Park, FL 32789
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  $3,450,000 Sold Jul 25, 2025

  182 N Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 5 Baths
  • 4,812 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $717/SF
  • 61 Days On Market

  Current Estimated Value $3,181,636

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  182 N Phelps Ave, Winter Park, FL 32789
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  $180,000 Sold Jan 06, 2026

  2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 8 Days On Market

  Current Estimated Value $181,621

  Last Listing Agent Chris Bessette KELLER WILLIAMS CLASSIC

  2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792
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  $1,950,000 Sold Sep 16, 2025

  141 Oakwood Way, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 3,909 Sq Ft
  • Built 2015

  Last Sold Summary

  • 14% Below List Price
  • $499/SF
  • 170 Days On Market

  Current Estimated Value $1,959,270

  Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

  141 Oakwood Way, Winter Park, FL 32789
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  $640,000 Sold Oct 22, 2025

  1922 Rowena Ave, Orlando, FL 32803

  • 3 Beds
  • 2 Baths
  • 1,490 Sq Ft
  • Built 1951

  Last Sold Summary

  • 3% Above List Price
  • $430/SF
  • 2 Days On Market

  Current Estimated Value $623,096

  Last Listing Agent William Snyder, II WILLIAM WHITE SNYDER II, PA

  1922 Rowena Ave, Orlando, FL 32803
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  $145,000 Sold Apr 23, 2026

  2500 Lee Rd Unit 243, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  Last Sold Summary

  • 28% Below List Price
  • $225/SF
  • 286 Days On Market

  Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

  2500 Lee Rd Unit 243, Winter Park, FL 32789
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  $850,000 Sold Mar 31, 2026

  1929 S Lakemont Ave, Winter Park, FL 32792

  • 3 Beds
  • 3.5 Baths
  • 2,160 Sq Ft
  • Built 2023

  Last Sold Summary

  • 10% Below List Price
  • $394/SF
  • 91 Days On Market

  Current Estimated Value $907,218

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  1929 S Lakemont Ave, Winter Park, FL 32792
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  $890,000 Sold Jul 23, 2025

  1849 Oak Ln, Orlando, FL 32803

  • Land
  • 23,522 Sq Ft
  • $1,648,148 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 12 Days On Market

  Current Estimated Value $876,670

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

  1849 Oak Ln, Orlando, FL 32803
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  $1,100,000 Sold May 29, 2025

  708 Balmoral Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,786 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $395/SF
  • 130 Days On Market

  Current Estimated Value $1,133,199

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  708 Balmoral Rd, Winter Park, FL 32789
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  $699,000 Sold Jun 30, 2025

  1632 Haven Dr, Orlando, FL 32803

  • 3 Beds
  • 2.5 Baths
  • 1,772 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $394/SF
  • 110 Days On Market

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  1632 Haven Dr, Orlando, FL 32803
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  $689,500 Sold Jul 19, 2025

  1129 Golfside Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $394/SF
  • 21 Days On Market

  Current Estimated Value $673,583

  Last Listing Agent Tess Muccigrosso RE/MAX 200 REALTY

  1129 Golfside Dr, Winter Park, FL 32792
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  $3,020,000 Sold Oct 02, 2025

  1820 Englewood Rd, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,263 Sq Ft
  • Built 2015

  Last Sold Summary

  • 8% Below List Price
  • $708/SF
  • 70 Days On Market

  Current Estimated Value $3,004,771

  Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

  1820 Englewood Rd, Winter Park, FL 32789
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  $799,000 Sold Apr 30, 2025

  2320 Janice Ave, Winter Park, FL 32789

  • Land
  • 12,196 Sq Ft
  • $2,853,571 per Acre

  Last Sold Summary

  • 2 Days On Market

  Current Estimated Value $785,667

  Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  2320 Janice Ave, Winter Park, FL 32789
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  $389,900 Sold Mar 18, 2026

  700 Melrose Ave Unit M4, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • Built 1964

  Last Sold Summary

  • 1% Below List Price
  • $363/SF
  • 7 Days On Market

  Current Estimated Value $383,763

  Last Listing Agent Mary Harmening ROAM FLORIDA REALTY LLC

  700 Melrose Ave Unit M4, Winter Park, FL 32789
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  $605,000 Sold Dec 22, 2025

  2478 Whitehall Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 1965

  Last Sold Summary

  • 19% Below List Price
  • $268/SF
  • 123 Days On Market

  Current Estimated Value $612,149

  Last Listing Agent Erica Magtira LPT REALTY, LLC

  2478 Whitehall Cir, Winter Park, FL 32792
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  $417,100 Sold Nov 24, 2025

  690 Osceola Ave Unit 502, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1969

  Last Sold Summary

  • 26% Below List Price
  • $298/SF
  • 196 Days On Market

  Current Estimated Value $437,105

  Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

  690 Osceola Ave Unit 502, Winter Park, FL 32789
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  $1,200,000 Sold Mar 20, 2026

  950 Aragon Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 2020

  Last Sold Summary

  • $463/SF
  • 5 Days On Market

  Current Estimated Value $1,184,514

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  950 Aragon Ave, Winter Park, FL 32789

Showing Results 41 - 80, Page 2 of 18