1,127

Recently Sold Winter Park, FL Homes

Section Image
  • 1446 Berkshire Ave, Winter Park, FL 32789
    1446 Berkshire Ave, Winter Park, FL 32789
    /2

    $1,877,500 Sold Apr 01, 2025

    1446 Berkshire Ave, Winter Park, FL 32789

    • 5 Beds
    • 6 Baths
    • 4,612 Sq Ft
    • Built 1925

    Last Sold Summary

    • 15% Below List Price
    • $407/SF
    • 5 Days On Market

    Current Estimated Value $1,914,776

    Last Listing Agent Jimmy Hendrickson SERHANT

    1446 Berkshire Ave, Winter Park, FL 32789
  • 637 N Park Ave, Winter Park, FL 32789
    637 N Park Ave, Winter Park, FL 32789
    /2

    $3,800,000 Sold Feb 24, 2026

    637 N Park Ave, Winter Park, FL 32789

    • 3 Beds
    • 5 Baths
    • 4,237 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Below List Price
    • $897/SF
    • 24 Days On Market

    Current Estimated Value $3,375,596

    Last Listing Agent Whitney Johnson COLDWELL BANKER REALTY

    637 N Park Ave, Winter Park, FL 32789
  • 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 $5,223,209

    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 $1,354,502

    Last Listing Agent Laura Ascenso CREEGAN GROUP

    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 $284,447

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

    1709 Winter Green Blvd, 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 $131,234

    Last Listing Agent Justin Adams EXP REALTY LLC

    1695 Lee Rd Unit C206, Winter Park, FL 32789
  • 1422 Tierra Cir, Winter Park, FL 32792
    1422 Tierra Cir, Winter Park, FL 32792
    /2

    $450,000 Sold Mar 10, 2026

    1422 Tierra Cir, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,827 Sq Ft
    • Built 1968

    Last Sold Summary

    • 12% Below List Price
    • $246/SF
    • 132 Days On Market

    Current Estimated Value $484,769

    Last Listing Agent Jennifer Conrado CHARLES RUTENBERG REALTY ORLANDO

    1422 Tierra Cir, Winter Park, FL 32792
  • 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 $1,170,618

    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

    Current Estimated Value $1,487,938

    Last Listing Agent Jerad Withrow SPECTRUM GLOBAL REALTY, INC

    7841 Georgeann St, Winter Park, FL 32792
  • 1871 Taylor Ave, Winter Park, FL 32789
    1871 Taylor Ave, Winter Park, FL 32789
    /2

    $1,500,000 Sold Mar 16, 2026

    1871 Taylor Ave, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,401 Sq Ft
    • Built 2016

    Last Sold Summary

    • 9% Below List Price
    • $441/SF
    • 2 Days On Market

    Current Estimated Value $2,121,289

    Last Listing Agent Laura Earl CORCORAN PREMIER REALTY

    1871 Taylor Ave, Winter Park, FL 32789
  • 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 $1,037,256

    Last Listing Agent Chris Creegan CREEGAN GROUP

    1821 Windsor Dr, Winter Park, FL 32789
  • 1144 Wading Waters Cir, Winter Park, FL 32792
    1144 Wading Waters Cir, Winter Park, FL 32792
    /2

    $1,400,000 Sold Mar 20, 2026

    1144 Wading Waters Cir, Winter Park, FL 32792

    • 5 Beds
    • 4.5 Baths
    • 4,307 Sq Ft
    • Built 2020

    Last Sold Summary

    • 7% Below List Price
    • $325/SF
    • 19 Days On Market

    Current Estimated Value $1,195,516

    Last Listing Agent Maria Huff PORCH LIGHT REALTY, LLC.

    1144 Wading Waters Cir, 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 $71,278

    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 $1,274,299

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

    857 Brock St, Winter Park, FL 32789
  • 1690 Viburnum Ln, Winter Park, FL 32792
    1690 Viburnum Ln, Winter Park, FL 32792
    /2

    $360,000 Sold Mar 10, 2026

    1690 Viburnum Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1960

    Last Sold Summary

    • $234/SF
    • 11 Days On Market

    Current Estimated Value $359,079

    Last Listing Agent Julie Boyd-Elrod CHARLES RUTENBERG REALTY ORLANDO

    1690 Viburnum Ln, Winter Park, FL 32792
  • 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 $1,605,356

    Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

    279 Rippling Ln, Winter Park, FL 32789
  • 2203 Via Tuscany, Winter Park, FL 32789
    2203 Via Tuscany, Winter Park, FL 32789
    /2

    $13,000,000 Sold Feb 24, 2026

    2203 Via Tuscany, Winter Park, FL 32789

    • 6 Beds
    • 9 Baths
    • 12,190 Sq Ft
    • Built 2002

    Last Sold Summary

    • 1% Above List Price
    • $1,066/SF
    • 4 Days On Market

    Current Estimated Value $8,622,657

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

    2203 Via Tuscany, 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 $441,470

    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 $2,024,453

    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 $1,597,304

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

    1541 Chestnut Ave, Winter Park, FL 32789
  • 2904 Parkland Dr, Winter Park, FL 32789
    2904 Parkland Dr, Winter Park, FL 32789
    /2

    $690,000 Sold Feb 20, 2026

    2904 Parkland Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 1952

    Last Sold Summary

    • $456/SF
    • 0 Days On Market

    Current Estimated Value $571,890

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

    2904 Parkland Dr, 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

    Current Estimated Value $84,556

    Last Listing Agent Tyann Huynh JADE KEY REALTY LLC

    110 Scottsdale Square, 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 $436,210

    Last Listing Agent Mary Dees CHOICEPOINTE REALTY, INC.

    2648 Amsden Rd, Winter Park, FL 32792
  • 5547 Garden Grove Cir, Winter Park, FL 32792
    5547 Garden Grove Cir, Winter Park, FL 32792
    /2

    $400,000 Sold Mar 11, 2026

    5547 Garden Grove Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,517 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Above List Price
    • $264/SF
    • 5 Days On Market

    Current Estimated Value $392,070

    Last Listing Agent Steve Dalton ROYALTY R E BOUTIQUE INC

    5547 Garden Grove Cir, 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 $545,572

    Last Listing Agent Meseydi Machado TCA REALTY, LLC

    407 S Lakemont Ave, Winter Park, FL 32792
  • 304 Scottsdale Square Unit L304, Winter Park, FL 32792
    304 Scottsdale Square Unit L304, Winter Park, FL 32792
    /2

    $72,000 Sold Feb 13, 2026

    304 Scottsdale Square Unit L304, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft
    • Built 1974

    Last Sold Summary

    • 10% Below List Price
    • $71/SF
    • 23 Days On Market

    Current Estimated Value $80,393

    Last Listing Agent Laura Hilton CHARLES RUTENBERG REALTY ORLANDO

    304 Scottsdale Square Unit L304, 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 $415,011

    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 $738,075

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    311 Cortland Ave, 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 $322,841

    Last Listing Agent Carlton Watson Listing Spark South Florida

    7561 Laurel Springs Dr, Winter Park, FL 32792
  • 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 $249,115

    Last Listing Agent Alayna Phillips EXP REALTY LLC

    1250 S Denning Dr Unit 111, Winter Park, FL 32789
  • 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 $411,331

    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

    Current Estimated Value $628,157

    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

    Current Estimated Value $494,305

    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 $173,342

    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 $521,850

    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 $524,384

    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 $292,986

    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

    Current Estimated Value $4,728,758

    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 $74,040

    Last Listing Agent Alan Barbosa DALTON WADE INC

    347 Scottsdale Square Unit 347, Winter Park, FL 32792

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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