Recently Sold Winter Park, FL Homes

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  $299,000 Sold Jan 15, 2026

  2804 Whispering Way, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Built 1986

  Last Sold Summary

  • $277/SF
  • 4 Days On Market

  Current Estimated Value $300,993

  Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

  2804 Whispering Way, Winter Park, FL 32792
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  $130,000 Sold May 09, 2025

  1695 Lee Rd Unit E205, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  Last Sold Summary

  • 10% Below List Price
  • $148/SF
  • 25 Days On Market

  Current Estimated Value $131,826

  Last Listing Agent Joseph Pacholski KELLER WILLIAMS HERITAGE REALTY

  1695 Lee Rd Unit E205, Winter Park, FL 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 $2,127,094

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1077 N Pennsylvania Ave, Winter Park, FL 32789
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  $290,000 Sold Feb 06, 2026

  1920 Carrigan Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1954

  Last Sold Summary

  • 14% Below List Price
  • $233/SF
  • 141 Days On Market

  Current Estimated Value $306,967

  Last Listing Agent Virginia Bellhorn WATSON REALTY CORP

  1920 Carrigan Ave, Winter Park, FL 32792
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  $620,000 Sold Jul 21, 2025

  2855 Lion Heart Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,727 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $359/SF
  • 62 Days On Market

  Current Estimated Value $584,472

  Last Listing Agent Kevin Henao LA ROSA REALTY LLC

  2855 Lion Heart Rd, Winter Park, FL 32792
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  $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 $668,030

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1511 Chestnut Ave, Winter Park, FL 32789
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  $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 $977,629

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
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  $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 $275,942

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit A22, Winter Park, FL 32789
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  $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 $1,298,029

  Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

  1500 Mizell Ave, Winter Park, FL 32789
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  $374,900 Sold Oct 10, 2025

  2028 Leanne Ct, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft
  • Built 1968

  Last Sold Summary

  • $244/SF
  • 9 Days On Market

  Last Listing Agent Jamie Ampel ALL SELLERS & BUYERS REALTY INC

  2028 Leanne Ct, Winter Park, FL 32792
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  $750,000 Sold Jun 09, 2025

  2756 Summerfield Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1967

  Last Sold Summary

  • 3% Above List Price
  • $431/SF
  • 4 Days On Market

  Current Estimated Value $739,041

  Last Listing Agent Alexis Davis FANNIE HILLMAN & ASSOCIATES

  2756 Summerfield Rd, Winter Park, FL 32792
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  $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 $2,222,050

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1661 Palm Ave, Winter Park, FL 32789
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  $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 $2,594,633

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  1020 Mayfield Ave, Winter Park, FL 32789
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  $714,000 Sold Mar 12, 2026

  636 Dunblane Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,803 Sq Ft
  • Built 1962

  Last Sold Summary

  • 2% Below List Price
  • $396/SF
  • 7 Days On Market

  Current Estimated Value $710,703

  Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  636 Dunblane Dr, Winter Park, FL 32792
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  $4,100,000 Sold Apr 18, 2025

  1691 Chestnut Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 4,582 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $895/SF
  • 1 Day On Market

  Current Estimated Value $4,040,574

  Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC

  1691 Chestnut Ave, Winter Park, FL 32789
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  $638,250 Sold Sep 02, 2025

  1536 Golfside Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1980

  Last Sold Summary

  • $338/SF
  • 3 Days On Market

  Current Estimated Value $633,355

  Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1536 Golfside Dr, Winter Park, FL 32792
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  $401,000 Sold Oct 15, 2025

  1809 Palmer Ave, Winter Park, FL 32792

  • Land
  • 0.21 Acre
  • $1,909,524 per Acre

  Last Sold Summary

  • 5 Days On Market

  Current Estimated Value $391,440

  Last Listing Agent Christina Munkberg COLDWELL BANKER REALTY

  1809 Palmer Ave, Winter Park, FL 32792
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  $775,000 Sold May 21, 2025

  1818 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $342/SF
  • 189 Days On Market

  Current Estimated Value $797,659

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1818 Mondrian Cir, Winter Park, FL 32789
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  $690,000 Sold Aug 14, 2025

  2433 Whitehall Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Above List Price
  • $375/SF
  • 2 Days On Market

  Current Estimated Value $651,402

  Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  2433 Whitehall Cir, Winter Park, FL 32792
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  $555,000 Sold Apr 25, 2025

  633 London Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft
  • Built 1966

  Last Sold Summary

  • 2% Below List Price
  • $313/SF
  • 15 Days On Market

  Current Estimated Value $552,094

  Last Listing Agent Barry Sanford PA CHARLES RUTENBERG REALTY ORLANDO

  633 London Rd, Winter Park, FL 32792
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  $730,000 Sold Mar 23, 2026

  1213 Lindenwood Ln, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft
  • Built 1960

  Last Sold Summary

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

  Current Estimated Value $726,130

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  1213 Lindenwood Ln, Winter Park, FL 32792
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  $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 $1,580,246

  Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1166 Oaks Blvd, Winter Park, FL 32789
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  $245,000 Sold Jun 26, 2025

  2471 Tahoe Cir, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $189/SF
  • 84 Days On Market

  Current Estimated Value $228,902

  Last Listing Agent Kevin Wilhelm MLSB THE BUREAU POWERED BY CAROM REALTY

  2471 Tahoe Cir, Winter Park, FL 32792
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  $400,000 Sold Jul 16, 2025

  3443 Arnel Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $266/SF
  • 15 Days On Market

  Current Estimated Value $388,810

  Last Listing Agent Lana More KELLER WILLIAMS WINTER PARK

  3443 Arnel Dr, Winter Park, FL 32792
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  $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 $1,312,562

  Last Listing Agent Jake Johnson SHORES REAL ESTATE

  1077 Minnesota Ave, Winter Park, FL 32789
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  $580,000 Sold Apr 21, 2025

  3006 Northwood Blvd, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,710 Sq Ft
  • Built 1953

  Last Sold Summary

  • 2% Below List Price
  • $339/SF
  • 1 Day On Market

  Current Estimated Value $656,461

  Last Listing Agent Chris Creegan CREEGAN GROUP

  3006 Northwood Blvd, Winter Park, FL 32789
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  $890,000 Sold Jun 12, 2025

  1762 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $393/SF
  • 114 Days On Market

  Current Estimated Value $922,502

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1762 Mondrian Cir, Winter Park, FL 32789
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  $440,000 Sold Jan 29, 2026

  1621 Puritan Ave, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,765 Sq Ft
  • Built 1963

  Last Sold Summary

  • 12% Below List Price
  • $249/SF
  • 342 Days On Market

  Current Estimated Value $440,258

  Last Listing Agent Alejandro Colon PREFERRED REAL ESTATE BROKERS

  1621 Puritan Ave, Winter Park, FL 32792
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  $1,088,000 Sold Jan 30, 2026

  1092 Wading Waters Cir, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 3,057 Sq Ft
  • Built 2019

  Last Sold Summary

  • 9% Below List Price
  • $356/SF
  • 60 Days On Market

  Current Estimated Value $1,103,120

  Last Listing Agent Tara Haefner KELLER WILLIAMS HERITAGE REALTY

  1092 Wading Waters Cir, Winter Park, FL 32792
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  $420,000 Sold May 06, 2025

  627 Carvell Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 1957

  Last Sold Summary

  • 6% Below List Price
  • $312/SF
  • 152 Days On Market

  Current Estimated Value $407,552

  Last Listing Agent Ray Al-Malt EXP REALTY LLC

  627 Carvell Dr, Winter Park, FL 32792
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  $223,000 Sold Oct 30, 2025

  1378 Chilean Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1960

  Last Sold Summary

  • $168/SF

  Current Estimated Value $350,528

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

  1378 Chilean Ln, Winter Park, FL 32792
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  $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 $1,577,588

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1394 Grove Terrace, Winter Park, FL 32789
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  $379,990 Sold Feb 27, 2026

  1378 Chilean Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1960

  Last Sold Summary

  • $267/SF
  • 13 Days On Market

  Current Estimated Value $350,528

  Last Listing Agent Constantin Florean FUTURE HOME REALTY INC

  1378 Chilean Ln, Winter Park, FL 32792
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  $625,000 Sold Sep 29, 2025

  3759 Kinsley Place, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,251 Sq Ft
  • Built 1988

  Last Sold Summary

  • 11% Below List Price
  • $278/SF
  • 50 Days On Market

  Current Estimated Value $623,389

  Last Listing Agent Drew Belani COMPASS FLORIDA LLC

  3759 Kinsley Place, Winter Park, FL 32792
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  $285,000 Sold Sep 24, 2025

  7777 Fernbrook Way, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Above List Price
  • $261/SF
  • 3 Days On Market

  Current Estimated Value $278,208

  Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  7777 Fernbrook Way, Winter Park, FL 32792
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  $675,000 Sold Mar 16, 2026

  620 Darcey Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,075 Sq Ft
  • Built 1967

  Last Sold Summary

  • 9% Below List Price
  • $325/SF
  • 14 Days On Market

  Current Estimated Value $709,827

  Last Listing Agent Jason Asa LPT REALTY, LLC

  620 Darcey Dr, Winter Park, FL 32792
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  $315,000 Sold Jan 01, 2026

  615 Warrenton Rd, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Below List Price
  • $258/SF
  • 50 Days On Market

  Current Estimated Value $312,189

  Last Listing Agent Bryan Burns RE/MAX DOWNTOWN

  615 Warrenton Rd, Winter Park, FL 32792
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  $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 $323,555

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
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  $790,000 Sold Jun 05, 2025

  600 Brechin Dr, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,360 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Below List Price
  • $335/SF
  • 12 Days On Market

  Current Estimated Value $781,081

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  600 Brechin Dr, Winter Park, FL 32792
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  $517,000 Sold Nov 07, 2025

  1628 Lawndale Cir, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 1984

  Last Sold Summary

  • 6% Below List Price
  • $301/SF
  • 6 Days On Market

  Current Estimated Value $520,042

  Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

  1628 Lawndale Cir, Winter Park, FL 32792

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