1,172

Recently Sold Winter Park, FL Homes

Section Image
  • 2003 Bentwood Dr, Winter Park, FL 32792
    2003 Bentwood Dr, Winter Park, FL 32792
    /2

    $430,000 Sold Jul 25, 2025

    2003 Bentwood Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,675 Sq Ft
    • Built 1981

    Last Sold Summary

    • 1% Above List Price
    • $257/SF
    • 16 Days On Market

    Current Estimated Value $429,589

    Last Listing Agent Heather Kolin PALMANO GROUP RE BROKERAGE LLC

    2003 Bentwood Dr, Winter Park, FL 32792
  • 291 Lewfield Cir Unit 291, Winter Park, FL 32792
    291 Lewfield Cir Unit 291, Winter Park, FL 32792
    /2

    $110,000 Sold Mar 14, 2025

    291 Lewfield Cir Unit 291, Winter Park, FL 32792

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

    Last Sold Summary

    • $162/SF
    • 7 Days On Market

    Current Estimated Value $124,384

    Last Listing Agent Christopher Courtney DENIZ REALTY PARTNERS LLC

    291 Lewfield Cir Unit 291, Winter Park, FL 32792
  • 2151 Conifer Ave, Winter Park, FL 32792
    2151 Conifer Ave, Winter Park, FL 32792
    /2

    $450,000 Sold Aug 28, 2025

    2151 Conifer Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,806 Sq Ft
    • Built 1970

    Last Sold Summary

    • 2% Below List Price
    • $249/SF
    • 32 Days On Market

    Current Estimated Value $447,300

    Last Listing Agent Denise Korrey KORR REALTY CORP

    2151 Conifer Ave, Winter Park, FL 32792
  • 2411 Gallery View Dr Unit 5, Winter Park, FL 32792
    2411 Gallery View Dr Unit 5, Winter Park, FL 32792
    /2

    $290,000 Sold Nov 24, 2025

    2411 Gallery View Dr Unit 5, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,004 Sq Ft
    • Built 1985

    Last Sold Summary

    • 9% Below List Price
    • $289/SF
    • 54 Days On Market

    Last Listing Agent Maria Elena Perez MEP REALTY INVESTMENTS LLC

    2411 Gallery View Dr Unit 5, Winter Park, FL 32792
  • 2634 Cayman Way, Winter Park, FL 32792
    2634 Cayman Way, Winter Park, FL 32792
    /2

    $263,999 Sold Jan 31, 2025

    2634 Cayman Way, Winter Park, FL 32792

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1978

    Last Sold Summary

    • 4% Below List Price
    • $244/SF
    • 92 Days On Market

    Current Estimated Value $263,783

    Last Listing Agent Odel Ximinies COLDWELL BANKER RESIDENTIAL RE

    2634 Cayman Way, Winter Park, FL 32792
  • 992 Carnation Dr, Winter Park, FL 32792
    992 Carnation Dr, Winter Park, FL 32792
    /2

    $330,000 Sold May 09, 2025

    992 Carnation Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Built 1959

    Last Sold Summary

    • 8% Below List Price
    • $330/SF
    • 57 Days On Market

    Current Estimated Value $339,190

    Last Listing Agent Bianca Botelho RE/MAX ASSURED

    992 Carnation Dr, Winter Park, FL 32792
  • 1392 Indiana Ave, Winter Park, FL 32789
    1392 Indiana Ave, Winter Park, FL 32789
    /2

    $580,000 Sold May 16, 2025

    1392 Indiana Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,936 Sq Ft
    • Built 2008

    Last Sold Summary

    • 11% Below List Price
    • $300/SF
    • 123 Days On Market

    Current Estimated Value $547,549

    Last Listing Agent Cody Hancock COLDWELL BANKER RESIDENTIAL RE

    1392 Indiana Ave, Winter Park, FL 32789
  • 2028 Sussex Rd, Winter Park, FL 32792
    2028 Sussex Rd, Winter Park, FL 32792
    /2

    $426,000 Sold Jul 03, 2025

    2028 Sussex Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft
    • Built 1973

    Last Sold Summary

    • 6% Below List Price
    • $254/SF
    • 39 Days On Market

    Current Estimated Value $427,174

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    2028 Sussex Rd, Winter Park, FL 32792
  • 1811 Winter Green Blvd, Winter Park, FL 32792
    1811 Winter Green Blvd, Winter Park, FL 32792
    /2

    $288,000 Sold Apr 08, 2025

    1811 Winter Green Blvd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft
    • Built 1994

    Last Sold Summary

    • 9% Below List Price
    • $243/SF
    • 204 Days On Market

    Current Estimated Value $296,594

    Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

    1811 Winter Green Blvd, Winter Park, FL 32792
  • 765 Via Lugano, Winter Park, FL 32789
    765 Via Lugano, Winter Park, FL 32789
    /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 $4,745,878

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

    765 Via Lugano, Winter Park, FL 32789
  • 731 Williams Dr, Winter Park, FL 32789
    731 Williams Dr, Winter Park, FL 32789
    /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 $2,988,516

    Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

    731 Williams Dr, Winter Park, FL 32789
  • 1445 Holts Grove Cir, Winter Park, FL 32789
    1445 Holts Grove Cir, Winter Park, FL 32789
    /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

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

    1445 Holts Grove Cir, Winter Park, FL 32789
  • 1901 Loch Berry Rd, Winter Park, FL 32792
    1901 Loch Berry Rd, Winter Park, FL 32792
    /2

    $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 $548,258

    Last Listing Agent Monica Tipirneni FOLIO REALTY LLC

    1901 Loch Berry Rd, Winter Park, FL 32792
  • 609 Langholm Dr, Winter Park, FL 32789
    609 Langholm Dr, Winter Park, FL 32789
    /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 $902,303

    Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

    609 Langholm Dr, Winter Park, FL 32789
  • 1000 Via Tuscany Oaks Way, Winter Park, FL 32789
    1000 Via Tuscany Oaks Way, Winter Park, FL 32789
    /2

    $2,599,000 Sold Feb 14, 2025

    1000 Via Tuscany Oaks Way, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 4,002 Sq Ft
    • Built 2003

    Last Sold Summary

    • $649/SF
    • 2 Days On Market

    Current Estimated Value $2,550,392

    Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

    1000 Via Tuscany Oaks Way, Winter Park, FL 32789
  • 2421 Summerfield Rd, Winter Park, FL 32792
    2421 Summerfield Rd, Winter Park, FL 32792
    /2

    $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

    Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

    2421 Summerfield Rd, Winter Park, FL 32792
  • 808 Denton Rd, Winter Park, FL 32792
    808 Denton Rd, Winter Park, FL 32792
    /2

    $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 $489,763

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

    808 Denton Rd, Winter Park, FL 32792
  • 2171 Forrest Rd, Winter Park, FL 32789
    2171 Forrest Rd, Winter Park, FL 32789
    /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

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

    2171 Forrest Rd, Winter Park, FL 32789
  • 2040 Venetian Way, Winter Park, FL 32789
    2040 Venetian Way, Winter Park, FL 32789
    /2

    $9,140,000 Sold Jan 15, 2025

    2040 Venetian Way, Winter Park, FL 32789

    • 6 Beds
    • 7.5 Baths
    • 8,082 Sq Ft
    • Built 2002

    Last Sold Summary

    • 9% Below List Price
    • $1,131/SF
    • 45 Days On Market

    Current Estimated Value $9,023,481

    Last Listing Agent Thomas Bonner COLDWELL BANKER RESIDENTIAL RE

    2040 Venetian Way, Winter Park, FL 32789
  • 1944 Bering Ave, Winter Park, FL 32789
    1944 Bering Ave, Winter Park, FL 32789
    /2

    $435,000 Sold Jan 22, 2025

    1944 Bering Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 1,956 Sq Ft
    • Built 1958

    Last Sold Summary

    • 2% Above List Price
    • $222/SF
    • 13 Days On Market

    Current Estimated Value $449,162

    Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES

    1944 Bering Ave, Winter Park, FL 32789
  • 1810 Taylor Ave, Winter Park, FL 32789
    1810 Taylor Ave, Winter Park, FL 32789
    /2

    $520,000 Sold Mar 31, 2025

    1810 Taylor Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,396 Sq Ft
    • Built 1977

    Last Sold Summary

    • 1% Below List Price
    • $372/SF
    • 0 Days On Market

    Current Estimated Value $532,311

    Last Listing Agent Julia Dalessandro FANNIE HILLMAN & ASSOCIATES

    1810 Taylor Ave, Winter Park, FL 32789
  • 207 E Kings Way, Winter Park, FL 32789
    207 E Kings Way, Winter Park, FL 32789
    /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

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    207 E Kings Way, Winter Park, FL 32789
  • 681 Balmoral Rd, Winter Park, FL 32789
    681 Balmoral Rd, Winter Park, FL 32789
    /2

    $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 $1,609,583

    Last Listing Agent Chris Burden EPIC REAL ESTATE ADVISORS LLC

    681 Balmoral Rd, Winter Park, FL 32789
  • 5144 N Orange Ave, Winter Park, FL 32792
    5144 N Orange Ave, Winter Park, FL 32792
    /2

    $335,000 Sold Sep 23, 2025

    5144 N Orange Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 1976

    Last Sold Summary

    • 16% Below List Price
    • $263/SF
    • 128 Days On Market

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    5144 N Orange Ave, Winter Park, FL 32792
  • 7319 Blue Jacket Place W, Winter Park, FL 32792
    7319 Blue Jacket Place W, Winter Park, FL 32792
    7319 Blue Jacket Place W, Winter Park, FL 32792
    /45

    $322,000 Sold Mar 12, 2025

    7319 Blue Jacket Place W, Winter Park, FL 32792

    • 3 Beds
    • 1.5 Baths
    • 1,118 Sq Ft
    • Built 1970

    Last Sold Summary

    • 4% Below List Price
    • $288/SF
    • 5 Days On Market

    Current Estimated Value $320,475

    Last Listing Agent Jennah LeBruno, LLC THE WILKINS WAY LLC

    7319 Blue Jacket Place W, Winter Park, FL 32792
  • 1109 Denton Rd, Winter Park, FL 32792
    1109 Denton Rd, Winter Park, FL 32792
    /2

    $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 $395,719

    Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

    1109 Denton Rd, Winter Park, FL 32792
  • 1833 Loch Berry Rd, Winter Park, FL 32789
    1833 Loch Berry Rd, Winter Park, FL 32789
    /2

    $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 $2,912,426

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    1833 Loch Berry Rd, Winter Park, FL 32789
  • 7352 Swallow Run, Winter Park, FL 32792
    7352 Swallow Run, Winter Park, FL 32792
    /2

    $145,000 Sold Aug 13, 2025

    7352 Swallow Run, Winter Park, FL 32792

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

    Last Sold Summary

    • 39% Below List Price
    • $181/SF
    • 68 Days On Market

    Current Estimated Value $144,914

    Last Listing Agent Ashley Quandt LEERDAM PROPERTIES INC.

    7352 Swallow Run, Winter Park, FL 32792
  • 1979 Staunton Ave, Winter Park, FL 32789
    1979 Staunton Ave, Winter Park, FL 32789
    /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 $234,534

    Last Listing Agent Michael Kara CORBELO LLC

    1979 Staunton Ave, Winter Park, FL 32789
  • 1873 Poinciana Rd, Winter Park, FL 32792
    1873 Poinciana Rd, Winter Park, FL 32792
    /2

    $385,000 Sold Apr 03, 2025

    1873 Poinciana Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,904 Sq Ft
    • Built 1970

    Last Sold Summary

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

    Current Estimated Value $403,451

    Last Listing Agent Benondre Cerezo COLDWELL BANKER REALTY

    1873 Poinciana Rd, Winter Park, FL 32792
  • 7553 Laurel Springs Dr, Winter Park, FL 32792
    7553 Laurel Springs Dr, Winter Park, FL 32792
    /2

    $399,900 Sold Oct 08, 2025

    7553 Laurel Springs Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 1973

    Last Sold Summary

    • $338/SF
    • 20 Days On Market

    Last Listing Agent Yamila Lopez EMPIRE NETWORK REALTY

    7553 Laurel Springs Dr, Winter Park, FL 32792
  • 2500 Lee Rd Unit 134, Winter Park, FL 32789
    2500 Lee Rd Unit 134, Winter Park, FL 32789
    /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

    Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

    2500 Lee Rd Unit 134, Winter Park, FL 32789
  • 700 Melrose Ave Unit E24, Winter Park, FL 32789
    700 Melrose Ave Unit E24, Winter Park, FL 32789
    700 Melrose Ave Unit E24, Winter Park, FL 32789
    /19

    $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 $179,813

    Last Listing Agent Susan Dering HOMEVEST REALTY

    700 Melrose Ave Unit E24, Winter Park, FL 32789
  • 1500 Gay Rd Unit 9B, Winter Park, FL 32789
    1500 Gay Rd Unit 9B, Winter Park, FL 32789
    /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

    Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 9B, Winter Park, FL 32789
  • 7531 Lodge Pole Trail, Winter Park, FL 32792
    7531 Lodge Pole Trail, Winter Park, FL 32792
    /2

    $600,000 Sold Apr 10, 2025

    7531 Lodge Pole Trail, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,141 Sq Ft
    • Built 1972

    Last Sold Summary

    • 1% Below List Price
    • $280/SF
    • 20 Days On Market

    Current Estimated Value $584,509

    Last Listing Agent Austin Cummings NEXTDWELL

    7531 Lodge Pole Trail, Winter Park, FL 32792
  • 195 Sandlewood Trail Unit 2, Winter Park, FL 32789
    195 Sandlewood Trail Unit 2, Winter Park, FL 32789
    /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 $250,811

    Last Listing Agent Matt Merdian MERDIAN REALTY LLC

    195 Sandlewood Trail Unit 2, Winter Park, FL 32789
  • 1570 Grove Terrace, Winter Park, FL 32789
    1570 Grove Terrace, Winter Park, FL 32789
    /2

    $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 $732,584

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

    1570 Grove Terrace, Winter Park, FL 32789
  • 1781 Goodrich Ave, Winter Park, FL 32789
    1781 Goodrich Ave, Winter Park, FL 32789
    1781 Goodrich Ave, Winter Park, FL 32789
    /49

    $1,650,000 Sold Mar 12, 2025

    1781 Goodrich Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,701 Sq Ft
    • Built 2024

    Last Sold Summary

    • 15% Below List Price
    • $611/SF
    • 88 Days On Market

    Current Estimated Value $1,662,226

    Last Listing Agent Laura Hope COMPASS FLORIDA LLC

    1781 Goodrich Ave, Winter Park, FL 32789
  • 1371 Lyndale Blvd, Winter Park, FL 32789
    1371 Lyndale Blvd, Winter Park, FL 32789
    /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 $1,283,867

    Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

    1371 Lyndale Blvd, Winter Park, FL 32789
  • 5111 Lake Howell Rd, Winter Park, FL 32792
    5111 Lake Howell Rd, Winter Park, FL 32792
    /2

    $525,000 Sold Dec 26, 2024

    5111 Lake Howell Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,278 Sq Ft
    • Built 1957

    Last Sold Summary

    • 12% Below List Price
    • $230/SF
    • 94 Days On Market

    Current Estimated Value $531,348

    Last Listing Agent Don Sprenkel 1ST CLASS REAL ESTATE LEGACY GROUP

    5111 Lake Howell Rd, Winter Park, FL 32792

Showing Results 41 - 80, Page 2 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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