Recently Sold Homes in 32789

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  $2,144,000

  Sold Aug 21, 2025

  1077 N Pennsylvania Ave, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,462 Sq Ft
  • Built 2004

  Last Sold Summary

  • $619/SF
  • 0 Days On Market

  Current Estimated Value $2,128,691

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1077 N Pennsylvania Ave, Winter Park, FL 32789
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  /2

  $675,000

  Sold Jul 10, 2025

  1511 Chestnut Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,275 Sq Ft
  • Built 1960

  Last Sold Summary

  • $529/SF
  • 1 Day On Market

  Current Estimated Value $681,645

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1511 Chestnut Ave, Winter Park, FL 32789
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  /2

  $955,000

  Sold Feb 24, 2026

  512 Clarendon Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,824 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $338/SF
  • 21 Days On Market

  Current Estimated Value $965,643

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
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  /2

  $280,000

  Sold Jul 30, 2025

  700 Melrose Ave Unit A22, Winter Park, FL 32789

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

  Last Sold Summary

  • 11% Below List Price
  • $261/SF
  • 130 Days On Market

  Current Estimated Value $285,523

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit A22, Winter Park, FL 32789
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  /2

  $1,300,000

  Sold Aug 28, 2025

  1500 Mizell Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,303 Sq Ft
  • Built 1957

  Last Sold Summary

  • $564/SF
  • 2 Days On Market

  Current Estimated Value $1,279,216

  Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

  1500 Mizell Ave, Winter Park, FL 32789
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  /2

  $2,295,000

  Sold Dec 16, 2025

  1661 Palm Ave, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 3,570 Sq Ft
  • Built 2025

  Last Sold Summary

  • 12% Below List Price
  • $643/SF
  • 26 Days On Market

  Current Estimated Value $2,201,722

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1661 Palm Ave, Winter Park, FL 32789
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  /2

  $2,700,000

  Sold Oct 30, 2025

  1020 Mayfield Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,663 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $1,014/SF
  • 149 Days On Market

  Current Estimated Value $2,787,254

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  1020 Mayfield Ave, Winter Park, FL 32789
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  /2

  $4,250,000

  Sold Jun 01, 2026

  1336 College Point, Winter Park, FL 32789

  • 4 Beds
  • 5 Baths
  • 3,181 Sq Ft
  • Built 1926

  Last Sold Summary

  • 8% Below List Price
  • $1,336/SF
  • 109 Days On Market

  Current Estimated Value $4,442,314

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

  1336 College Point, Winter Park, FL 32789
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  /2

  $1,590,000

  Sold Mar 06, 2026

  1166 Oaks Blvd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft
  • Built 2018

  Last Sold Summary

  • 12% Below List Price
  • $556/SF
  • 153 Days On Market

  Current Estimated Value $1,621,179

  Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1166 Oaks Blvd, Winter Park, FL 32789
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  /2

  $2,050,000

  Sold Apr 30, 2026

  1205 Mayfield Ave, Winter Park, FL 32789

  • Land
  • 23,958 Sq Ft
  • $3,727,273 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 89 Days On Market

  Current Estimated Value $2,208,348

  Last Listing Agent Abby Nelson RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
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  /2

  $1,335,000

  Sold Jul 15, 2025

  1077 Minnesota Ave, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,046 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $438/SF
  • 75 Days On Market

  Current Estimated Value $1,307,945

  Last Listing Agent Jake Johnson SHORES REAL ESTATE

  1077 Minnesota Ave, Winter Park, FL 32789
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  /2

  $261,000

  Sold May 13, 2026

  1500 Gay Rd Unit 8D, Winter Park, FL 32789

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

  Last Sold Summary

  • 2% Below List Price
  • $254/SF
  • 19 Days On Market

  Current Estimated Value $264,210

  Last Listing Agent Trevor Laug. Realtor SOLID OAK REAL ESTATE LLC

  1500 Gay Rd Unit 8D, Winter Park, FL 32789
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  /2

  $800,000

  Sold Apr 30, 2026

  737 N Capen Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,930 Sq Ft
  • Built 2021

  Last Sold Summary

  • 13% Below List Price
  • $415/SF
  • 99 Days On Market

  Current Estimated Value $883,096

  Last Listing Agent Jenn Carlisle LPT REALTY, LLC

  737 N Capen Ave, Winter Park, FL 32789
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  /2

  $640,000

  Sold Jun 05, 2026

  352 Cambridge Blvd, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 1,917 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Below List Price
  • $334/SF
  • 46 Days On Market

  Current Estimated Value $631,911

  Last Listing Agent Karen Jacobs COLDWELL BANKER REALTY

  352 Cambridge Blvd, Winter Park, FL 32789
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  /2

  $1,575,000

  Sold Aug 14, 2025

  1394 Grove Terrace, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,958 Sq Ft
  • Built 2002

  Last Sold Summary

  • $532/SF
  • 5 Days On Market

  Current Estimated Value $1,595,861

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1394 Grove Terrace, Winter Park, FL 32789
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  /2

  $325,000

  Sold Dec 30, 2025

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $280/SF
  • 6 Days On Market

  Current Estimated Value $324,182

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
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  /2

  $720,000

  Sold Jan 20, 2026

  2955 Lolissa Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,538 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $204/SF
  • 47 Days On Market

  Current Estimated Value $812,250

  Last Listing Agent Catherine Williams COLDWELL BANKER REALTY

  2955 Lolissa Ln, Winter Park, FL 32789
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  /2

  $2,285,000

  Sold Nov 19, 2025

  521 S Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,883 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $588/SF
  • 118 Days On Market

  Current Estimated Value $2,276,166

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  521 S Phelps Ave, Winter Park, FL 32789
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  /2

  $3,100,000

  Sold Jun 27, 2025

  731 Williams Dr, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,260 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $728/SF
  • 45 Days On Market

  Current Estimated Value $2,885,321

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  731 Williams Dr, Winter Park, FL 32789
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  /2

  $4,772,500

  Sold Sep 18, 2025

  765 Via Lugano, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,319 Sq Ft
  • Built 2019

  Last Sold Summary

  • $1,105/SF
  • 1 Day On Market

  Current Estimated Value $4,778,066

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

  765 Via Lugano, Winter Park, FL 32789
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  /2

  $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 $2,704,546

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

  1445 Holts Grove Cir, Winter Park, FL 32789
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  /2

  $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 $911,312

  Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
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  /2

  $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 $3,426,438

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

  2171 Forrest Rd, Winter Park, FL 32789
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  /2

  $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 $1,709,521

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  207 E Kings Way, Winter Park, FL 32789
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  /2

  $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 $242,411

  Last Listing Agent Michael Kara CORBELO LLC

  1979 Staunton Ave, Winter Park, FL 32789
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  /2

  $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 $1,924,828

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  501 Henkel Cir, Winter Park, FL 32789
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  /2

  $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 $421,722

  Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

  1847 Azalea Ave, Winter Park, FL 32789
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  /2

  $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 $192,989

  Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

  2500 Lee Rd Unit 134, Winter Park, FL 32789
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  /2

  $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 $258,285

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 9B, Winter Park, FL 32789
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  /2

  $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 $251,521

  Last Listing Agent Matt Merdian MERDIAN REALTY LLC

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789
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  /2

  $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 $1,287,836

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
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  /2

  $235,000

  Sold Jan 29, 2026

  613 Orange Tree Ct Unit 507, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Below List Price
  • $187/SF
  • 10 Days On Market

  Current Estimated Value $234,369

  Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

  613 Orange Tree Ct Unit 507, Maitland, FL 32751
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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 $658,000

  David Weekley Homes Central Living - Downtown

  2304 Depauw Ave, Orlando, FL 32804
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  /2

  $500,000

  Sold May 27, 2026

  720 W Webster Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Below List Price
  • $369/SF
  • 54 Days On Market

  Current Estimated Value $515,477

  Last Listing Agent Vincent Cordaro SERHANT

  720 W Webster Ave, Winter Park, FL 32789
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  /2

  $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

  Current Estimated Value $232,398

  Last Listing Agent Sean McCartney PRISTINE FLORIDA PROPERTIES LLC

  1500 Gay Rd Unit 7A, Winter Park, FL 32789
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  /2

  $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 $2,938,183

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  182 N Phelps Ave, Winter Park, FL 32789
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  /2

  $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 $1,979,738

  Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

  141 Oakwood Way, Winter Park, FL 32789
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  /2

  $160,000

  Sold Jun 05, 2026

  2500 Lee Rd Unit 122, Winter Park, FL 32789

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

  Last Sold Summary

  • 11% Below List Price
  • $248/SF
  • 60 Days On Market

  Current Estimated Value $176,362

  Last Listing Agent Andrea Aylett-Hosch PINEAPPLE PLACE REALTY, LLC

  2500 Lee Rd Unit 122, Winter Park, FL 32789
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  /2

  $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

  Current Estimated Value $156,952

  Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

  2500 Lee Rd Unit 243, Winter Park, FL 32789
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  /2

  $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 $861,186

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  1929 S Lakemont Ave, Winter Park, FL 32792

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