1,143

Recently Sold Winter Park, FL Homes

Section Image
  • 541 Virginia Dr, Winter Park, FL 32789
    541 Virginia Dr, Winter Park, FL 32789
    /2

    $5,400,000 Sold Jul 14, 2025

    541 Virginia Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 4,725 Sq Ft
    • Built 2008

    Last Sold Summary

    • 14% Below List Price
    • $1,143/SF
    • 152 Days On Market

    Current Estimated Value $5,143,011

    Last Listing Agent Keith Moore HOMEVEST REALTY

    541 Virginia Dr, Winter Park, FL 32789
  • 1600 Barcelona Way, Winter Park, FL 32789
    1600 Barcelona Way, Winter Park, FL 32789
    /2

    $1,305,000 Sold Nov 05, 2025

    1600 Barcelona Way, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,014 Sq Ft
    • Built 1972

    Last Sold Summary

    • 12% Below List Price
    • $433/SF
    • 175 Days On Market

    Current Estimated Value $1,351,087

    Last Listing Agent Laura Ascenso LPT REALTY, LLC

    1600 Barcelona Way, Winter Park, FL 32789
  • 1709 Winter Green Blvd, Winter Park, FL 32792
    1709 Winter Green Blvd, Winter Park, FL 32792
    /2

    $284,900 Sold May 01, 2025

    1709 Winter Green Blvd, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 1988

    Last Sold Summary

    • $195/SF
    • 12 Days On Market

    Current Estimated Value $286,359

    Last Listing Agent Allison Day RE/MAX TOWN & COUNTRY REALTY

    1709 Winter Green Blvd, Winter Park, FL 32792
  • 1860 Linden Rd, Winter Park, FL 32792
    1860 Linden Rd, Winter Park, FL 32792
    /2

    $566,000 Sold Mar 25, 2025

    1860 Linden Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1957

    Last Sold Summary

    • 22% Below List Price
    • $311/SF
    • 36 Days On Market

    Current Estimated Value $561,972

    Last Listing Agent Kathy Williams REAL BROKER, LLC

    1860 Linden Rd, Winter Park, FL 32792
  • 1695 Lee Rd Unit C206, Winter Park, FL 32789
    1695 Lee Rd Unit C206, Winter Park, FL 32789
    /2

    $130,000 Sold Nov 05, 2025

    1695 Lee Rd Unit C206, Winter Park, FL 32789

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

    Last Sold Summary

    • 4% Below List Price
    • $148/SF
    • 43 Days On Market

    Current Estimated Value $131,986

    Last Listing Agent Justin Adams EXP REALTY LLC

    1695 Lee Rd Unit C206, Winter Park, FL 32789
  • 4052 Gilder Rose Place, Winter Park, FL 32792
    4052 Gilder Rose Place, Winter Park, FL 32792
    /2

    $1,180,000 Sold Jul 31, 2025

    4052 Gilder Rose Place, Winter Park, FL 32792

    • 4 Beds
    • 5 Baths
    • 4,015 Sq Ft
    • Built 1995

    Last Sold Summary

    • 6% Below List Price
    • $294/SF
    • 37 Days On Market

    Current Estimated Value $1,201,674

    Last Listing Agent Steve Lang HOMEVEST REALTY

    4052 Gilder Rose Place, Winter Park, FL 32792
  • 7841 Georgeann St, Winter Park, FL 32792
    7841 Georgeann St, Winter Park, FL 32792
    /2

    $1,500,000 Sold Nov 14, 2025

    7841 Georgeann St, Winter Park, FL 32792

    • 4 Beds
    • 4 Baths
    • 4,000 Sq Ft
    • Built 1977

    Last Sold Summary

    • 33% Below List Price
    • $375/SF
    • 180 Days On Market

    Last Listing Agent Jerad Withrow SPECTRUM GLOBAL REALTY, INC

    7841 Georgeann St, Winter Park, FL 32792
  • 1821 Windsor Dr, Winter Park, FL 32789
    1821 Windsor Dr, Winter Park, FL 32789
    /2

    $995,000 Sold Jul 22, 2025

    1821 Windsor Dr, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,188 Sq Ft
    • Built 2017

    Last Sold Summary

    • 10% Below List Price
    • $455/SF
    • 25 Days On Market

    Current Estimated Value $1,048,300

    Last Listing Agent Chris Creegan CREEGAN GROUP

    1821 Windsor Dr, Winter Park, FL 32789
  • 5049 Lake Howell Rd, Winter Park, FL 32792
    5049 Lake Howell Rd, Winter Park, FL 32792
    /2

    $1,095,000 Sold Feb 19, 2025

    5049 Lake Howell Rd, Winter Park, FL 32792

    • 4 Beds
    • 4.5 Baths
    • 4,462 Sq Ft
    • Built 2014

    Last Sold Summary

    • 9% Below List Price
    • $245/SF
    • 33 Days On Market

    Current Estimated Value $1,129,759

    Last Listing Agent Greg Vazzana FANNIE HILLMAN & ASSOCIATES

    5049 Lake Howell Rd, Winter Park, FL 32792
  • 100 S Interlachen Ave Unit 203D, Winter Park, FL 32789
    100 S Interlachen Ave Unit 203D, Winter Park, FL 32789
    /2

    $750,000 Sold Oct 02, 2025

    100 S Interlachen Ave Unit 203D, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,267 Sq Ft
    • Built 1971

    Last Sold Summary

    • 3% Below List Price
    • $592/SF
    • 0 Days On Market

    Last Listing Agent Michael Ford FANNIE HILLMAN & ASSOCIATES

    100 S Interlachen Ave Unit 203D, Winter Park, FL 32789
  • 167 Scottsdale Square Unit E167, Winter Park, FL 32792
    167 Scottsdale Square Unit E167, Winter Park, FL 32792
    /2

    $65,000 Sold Jul 31, 2025

    167 Scottsdale Square Unit E167, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft
    • Built 1974

    Last Sold Summary

    • 24% Below List Price
    • $83/SF
    • 19 Days On Market

    Current Estimated Value $73,132

    Last Listing Agent Nevelle Chambers LPT REALTY, LLC

    167 Scottsdale Square Unit E167, Winter Park, FL 32792
  • 857 Brock St, Winter Park, FL 32789
    857 Brock St, Winter Park, FL 32789
    /2

    $1,300,000 Sold Oct 02, 2025

    857 Brock St, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,288 Sq Ft
    • Built 1964

    Last Sold Summary

    • $568/SF
    • 0 Days On Market

    Current Estimated Value $1,278,927

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    857 Brock St, Winter Park, FL 32789
  • 279 Rippling Ln, Winter Park, FL 32789
    279 Rippling Ln, Winter Park, FL 32789
    /2

    $1,587,500 Sold Jul 31, 2025

    279 Rippling Ln, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 3,472 Sq Ft
    • Built 1961

    Last Sold Summary

    • 12% Below List Price
    • $457/SF
    • 318 Days On Market

    Current Estimated Value $1,599,171

    Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

    279 Rippling Ln, Winter Park, FL 32789
  • 5073 Lake Howell Rd, Winter Park, FL 32792
    5073 Lake Howell Rd, Winter Park, FL 32792
    /2

    $440,000 Sold Oct 10, 2025

    5073 Lake Howell Rd, Winter Park, FL 32792

    • 5 Beds
    • 2 Baths
    • 2,272 Sq Ft
    • Built 1956

    Last Sold Summary

    • 2% Below List Price
    • $194/SF
    • 2 Days On Market

    Current Estimated Value $453,706

    Last Listing Agent Alex Khalil EXP REALTY LLC

    5073 Lake Howell Rd, Winter Park, FL 32792
  • 2915 Parkland Dr, Winter Park, FL 32789
    2915 Parkland Dr, Winter Park, FL 32789
    /2

    $2,155,000 Sold Aug 23, 2025

    2915 Parkland Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,356 Sq Ft
    • Built 2025

    Last Sold Summary

    • $642/SF

    Current Estimated Value $2,033,626

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

    2915 Parkland Dr, Winter Park, FL 32789
  • 1541 Chestnut Ave, Winter Park, FL 32789
    1541 Chestnut Ave, Winter Park, FL 32789
    /2

    $1,607,160 Sold Aug 01, 2025

    1541 Chestnut Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,840 Sq Ft
    • Built 2018

    Last Sold Summary

    • 4% Above List Price
    • $566/SF
    • 2 Days On Market

    Current Estimated Value $1,579,657

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    1541 Chestnut Ave, Winter Park, FL 32789
  • 110 Scottsdale Square, Winter Park, FL 32792
    110 Scottsdale Square, Winter Park, FL 32792
    /2

    $85,000 Sold Nov 13, 2025

    110 Scottsdale Square, Winter Park, FL 32792

    • 2 Beds
    • 1.5 Baths
    • 1,085 Sq Ft
    • Built 1974

    Last Sold Summary

    • $78/SF
    • 0 Days On Market

    Last Listing Agent Tyann Huynh JADE KEY REALTY LLC

    110 Scottsdale Square, Winter Park, FL 32792
  • 2100 Shirewood Ct, Winter Park, FL 32792
    2100 Shirewood Ct, Winter Park, FL 32792
    /2

    $370,000 Sold Feb 28, 2025

    2100 Shirewood Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,427 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $259/SF
    • 7 Days On Market

    Current Estimated Value $388,261

    Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    2100 Shirewood Ct, Winter Park, FL 32792
  • 2648 Amsden Rd, Winter Park, FL 32792
    2648 Amsden Rd, Winter Park, FL 32792
    /2

    $450,000 Sold Oct 31, 2025

    2648 Amsden Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,623 Sq Ft
    • Built 1959

    Last Sold Summary

    • 8% Below List Price
    • $277/SF
    • 113 Days On Market

    Current Estimated Value $432,783

    Last Listing Agent Mary Dees CHOICEPOINTE REALTY, INC.

    2648 Amsden Rd, Winter Park, FL 32792
  • 407 S Lakemont Ave, Winter Park, FL 32792
    407 S Lakemont Ave, Winter Park, FL 32792
    /2

    $475,000 Sold Jun 06, 2025

    407 S Lakemont Ave, Winter Park, FL 32792

    • 3 Beds
    • 1 Bath
    • 1,314 Sq Ft
    • Built 1957

    Last Sold Summary

    • $361/SF
    • 3 Days On Market

    Current Estimated Value $551,161

    Last Listing Agent Meseydi Machado TCA REALTY, LLC

    407 S Lakemont Ave, Winter Park, FL 32792
  • 2681 Tierra Cir, Winter Park, FL 32792
    2681 Tierra Cir, Winter Park, FL 32792
    2681 Tierra Cir, Winter Park, FL 32792
    /52

    $415,000 Sold Sep 24, 2025

    2681 Tierra Cir, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft
    • Built 1969

    Last Sold Summary

    • $221/SF
    • 5 Days On Market

    Current Estimated Value $419,412

    Last Listing Agent Robert Kirkland Simply Real Estate

    2681 Tierra Cir, Winter Park, FL 32792
  • 311 Cortland Ave, Winter Park, FL 32789
    311 Cortland Ave, Winter Park, FL 32789
    /2

    $750,000 Sold Sep 25, 2025

    311 Cortland Ave, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,382 Sq Ft
    • Built 1952

    Last Sold Summary

    • 6% Below List Price
    • $543/SF
    • 48 Days On Market

    Current Estimated Value $751,161

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    311 Cortland Ave, Winter Park, FL 32789
  • 1250 S Denning Dr Unit 111, Winter Park, FL 32789
    1250 S Denning Dr Unit 111, Winter Park, FL 32789
    /2

    $259,000 Sold Aug 29, 2025

    1250 S Denning Dr Unit 111, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 908 Sq Ft
    • Built 1967

    Last Sold Summary

    • $285/SF
    • 76 Days On Market

    Current Estimated Value $256,565

    Last Listing Agent Alayna Phillips EXP REALTY LLC

    1250 S Denning Dr Unit 111, Winter Park, FL 32789
  • 7561 Laurel Springs Dr, Winter Park, FL 32792
    7561 Laurel Springs Dr, Winter Park, FL 32792
    7561 Laurel Springs Dr, Winter Park, FL 32792
    /28

    $320,000 Sold May 08, 2025

    7561 Laurel Springs Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,094 Sq Ft
    • Built 1973

    Last Sold Summary

    • 5% Below List Price
    • $293/SF
    • 18 Days On Market

    Current Estimated Value $325,955

    Last Listing Agent Carlton Watson Listing Spark South Florida

    7561 Laurel Springs Dr, Winter Park, FL 32792
  • 693 Minnesota Ave, Winter Park, FL 32789
    693 Minnesota Ave, Winter Park, FL 32789
    /2

    $435,000 Sold Jun 06, 2025

    693 Minnesota Ave, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,038 Sq Ft
    • Built 2000

    Last Sold Summary

    • $419/SF

    Current Estimated Value $434,497

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

    693 Minnesota Ave, Winter Park, FL 32789
  • 1985 Japonica Rd, Winter Park, FL 32792
    1985 Japonica Rd, Winter Park, FL 32792
    /2

    $391,250 Sold Aug 13, 2025

    1985 Japonica Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,096 Sq Ft
    • Built 1972

    Last Sold Summary

    • 13% Below List Price
    • $187/SF
    • 71 Days On Market

    Last Listing Agent Aaron Mighty MIGHTY REALTY INC

    1985 Japonica Rd, Winter Park, FL 32792
  • 382 Perth Ln, Winter Park, FL 32792
    382 Perth Ln, Winter Park, FL 32792
    /2

    $500,000 Sold Nov 26, 2025

    382 Perth Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,277 Sq Ft
    • Built 1958

    Last Sold Summary

    • 3% Below List Price
    • $392/SF
    • 6 Days On Market

    Last Listing Agent Jennifer Draper REAL BROKER, LLC

    382 Perth Ln, Winter Park, FL 32792
  • 2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792
    2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792
    /2

    $175,000 Sold Sep 08, 2025

    2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792

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

    Last Sold Summary

    • 15% Below List Price
    • $172/SF
    • 165 Days On Market

    Current Estimated Value $178,330

    Last Listing Agent Dean D Nikolic PMI PROPERTY ALLIANCE

    2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792
  • 1307 Lindenwood Ln, Winter Park, FL 32792
    1307 Lindenwood Ln, Winter Park, FL 32792
    1307 Lindenwood Ln, Winter Park, FL 32792
    /40

    $525,000 Sold May 09, 2025

    1307 Lindenwood Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,612 Sq Ft
    • Built 1960

    Last Sold Summary

    • $326/SF
    • 16 Days On Market

    Current Estimated Value $522,801

    Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1307 Lindenwood Ln, Winter Park, FL 32792
  • 1409 Sunset Dr, Winter Park, FL 32789
    1409 Sunset Dr, Winter Park, FL 32789
    /2

    $530,000 Sold Oct 02, 2025

    1409 Sunset Dr, Winter Park, FL 32789

    • 2 Beds
    • 1.5 Baths
    • 1,107 Sq Ft
    • Built 1930

    Last Sold Summary

    • 2% Above List Price
    • $479/SF
    • 4 Days On Market

    Current Estimated Value $525,110

    Last Listing Agent Ahmad Karain R MICHAELS REALTY LLC

    1409 Sunset Dr, Winter Park, FL 32789
  • 5588 Garden Grove Cir, Winter Park, FL 32792
    5588 Garden Grove Cir, Winter Park, FL 32792
    /2

    $285,123 Sold Jul 15, 2025

    5588 Garden Grove Cir, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,310 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $218/SF
    • 24 Days On Market

    Current Estimated Value $295,034

    Last Listing Agent Joyce Sanders FLORIDA REAL ESTATE PROPERTIES LLC

    5588 Garden Grove Cir, Winter Park, FL 32792
  • 641 Bonita Dr, Winter Park, FL 32789
    641 Bonita Dr, Winter Park, FL 32789
    /2

    $4,800,000 Sold Jan 02, 2026

    641 Bonita Dr, Winter Park, FL 32789

    • 5 Beds
    • 6 Baths
    • 6,699 Sq Ft
    • Built 1948

    Last Sold Summary

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

    Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

    641 Bonita Dr, Winter Park, FL 32789
  • 347 Scottsdale Square Unit 347, Winter Park, FL 32792
    347 Scottsdale Square Unit 347, Winter Park, FL 32792
    /2

    $80,000 Sold Jun 30, 2025

    347 Scottsdale Square Unit 347, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 756 Sq Ft
    • Built 1974

    Last Sold Summary

    • 27% Below List Price
    • $106/SF
    • 10 Days On Market

    Current Estimated Value $79,865

    Last Listing Agent Alan Barbosa DALTON WADE INC

    347 Scottsdale Square Unit 347, Winter Park, FL 32792
  • 1727 Winter Green Blvd, Winter Park, FL 32792
    1727 Winter Green Blvd, Winter Park, FL 32792
    1727 Winter Green Blvd, Winter Park, FL 32792
    /18

    $280,000 Sold May 15, 2025

    1727 Winter Green Blvd, Winter Park, FL 32792

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

    Last Sold Summary

    • 4% Below List Price
    • $236/SF
    • 64 Days On Market

    Current Estimated Value $283,305

    Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

    1727 Winter Green Blvd, Winter Park, FL 32792
  • 8413 Commander Cove, Winter Park, FL 32792
    8413 Commander Cove, Winter Park, FL 32792
    /2

    $430,000 Sold Mar 21, 2025

    8413 Commander Cove, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,634 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $263/SF
    • 15 Days On Market

    Current Estimated Value $428,868

    Last Listing Agent Tim Boon CREEGAN GROUP

    8413 Commander Cove, Winter Park, FL 32792
  • 4952 Tangerine Ave, Winter Park, FL 32792
    4952 Tangerine Ave, Winter Park, FL 32792
    /2

    $200,000 Sold Jul 25, 2025

    4952 Tangerine Ave, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,281 Sq Ft
    • Built 1973

    Last Sold Summary

    • $156/SF
    • 22 Days On Market

    Current Estimated Value $203,890

    Last Listing Agent Rick Brown KELLER WILLIAMS ADVANTAGE 2 REALTY

    4952 Tangerine Ave, Winter Park, FL 32792
  • 104 Moyses Rd, Winter Park, FL 32792
    104 Moyses Rd, Winter Park, FL 32792
    /2

    $467,000 Sold Feb 10, 2025

    104 Moyses Rd, Winter Park, FL 32792

    • 4 Beds
    • 4 Baths
    • 1,872 Sq Ft
    • Built 1985

    Last Sold Summary

    • 21% Below List Price
    • $249/SF
    • 43 Days On Market

    Last Listing Agent Georgina O'Bryan SIGNATURE BROKERS REALTY LLC

    104 Moyses Rd, Winter Park, FL 32792
  • 5122 N Woodcrest Dr, Winter Park, FL 32792
    5122 N Woodcrest Dr, Winter Park, FL 32792
    /2

    $430,000 Sold Nov 10, 2025

    5122 N Woodcrest Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,499 Sq Ft
    • Built 1969

    Last Sold Summary

    • $287/SF
    • 5 Days On Market

    Last Listing Agent Ken Pozek REAL BROKER, LLC

    5122 N Woodcrest Dr, Winter Park, FL 32792
  • 567 Osceola Ave, Winter Park, FL 32789
    567 Osceola Ave, Winter Park, FL 32789
    /2

    $1,100,000 Sold Mar 28, 2025

    567 Osceola Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,651 Sq Ft
    • Built 1912

    Last Sold Summary

    • 12% Below List Price
    • $415/SF
    • 42 Days On Market

    Current Estimated Value $1,116,234

    Last Listing Agent Susannah Dance COLDWELL BANKER RESIDENTIAL RE

    567 Osceola Ave, Winter Park, FL 32789
  • 2838 Wright Ave, Winter Park, FL 32789
    2838 Wright Ave, Winter Park, FL 32789
    /2

    $760,000 Sold Jun 09, 2025

    2838 Wright Ave, Winter Park, FL 32789

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft
    • Built 1952

    Last Sold Summary

    • 5% Below List Price
    • $674/SF
    • 2 Days On Market

    Current Estimated Value $743,488

    Last Listing Agent Jordan Suglio BALDWIN PARK REALTY LLC

    2838 Wright Ave, Winter Park, FL 32789

Showing Results 201 - 240, Page 6 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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