1,127

Recently Sold Winter Park, FL Homes

Section Image
  • /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 $5,249,084

    Last Listing Agent Keith Moore HOMEVEST REALTY

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

    $260,000

    Sold May 27, 2026

    1952 Spring St, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • Built 1983

    Last Sold Summary

    • 5% Below List Price
    • $248/SF
    • 76 Days On Market

    Current Estimated Value $268,479

    Last Listing Agent Bethanne Baer BEAR TEAM REAL ESTATE

    1952 Spring St, Winter Park, FL 32792
  • /2

    $1,655,000

    Sold May 14, 2026

    629 Country Club Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,031 Sq Ft
    • Built 2026

    Last Sold Summary

    • 2% Below List Price
    • $546/SF
    • 58 Days On Market

    Current Estimated Value $1,343,667

    Last Listing Agent Randy Lazarus CLASSIC HOMES

    629 Country Club Dr, 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 $1,346,515

    Last Listing Agent Laura Ascenso CREEGAN GROUP

    1600 Barcelona Way, 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 $126,441

    Last Listing Agent Justin Adams EXP REALTY LLC

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

    $440,000

    Sold May 12, 2026

    3642 Periwinkle Dr, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 1,945 Sq Ft
    • Built 1964

    Last Sold Summary

    • 3% Below List Price
    • $226/SF
    • 218 Days On Market

    Current Estimated Value $431,205

    Last Listing Agent John Hwangbo HONEST REAL ESTATE COMPANY

    3642 Periwinkle Dr, Winter Park, FL 32792
  • /2

    $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 $303,233

    Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

    2804 Whispering Way, 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 $456,595

    Last Listing Agent Jennifer Conrado CHARLES RUTENBERG REALTY ORLANDO

    1422 Tierra Cir, 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 $1,220,797

    Last Listing Agent Steve Lang HOMEVEST REALTY

    4052 Gilder Rose Place, 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 $1,513,053

    Last Listing Agent Jerad Withrow SPECTRUM GLOBAL REALTY, INC

    7841 Georgeann St, Winter Park, FL 32792
  • /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 $1,563,542

    Last Listing Agent Laura Earl CORCORAN PREMIER REALTY

    1871 Taylor Ave, 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 $1,045,120

    Last Listing Agent Chris Creegan CREEGAN GROUP

    1821 Windsor Dr, Winter Park, FL 32789
  • /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 $1,401,179

    Last Listing Agent Maria Huff PORCH LIGHT REALTY, LLC.

    1144 Wading Waters Cir, Winter Park, FL 32792
  • /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
  • /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 $1,293,504

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

    857 Brock St, Winter Park, FL 32789
  • /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 $68,356

    Last Listing Agent Nevelle Chambers LPT REALTY, LLC

    167 Scottsdale Square Unit E167, Winter Park, FL 32792
  • /2

    $650,000

    Sold May 08, 2026

    1098 Wildmeadow Run, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,770 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Above List Price
    • $367/SF
    • 12 Days On Market

    Current Estimated Value $631,329

    Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

    1098 Wildmeadow Run, Winter Park, FL 32792
  • /2

    $190,000

    Sold Jun 12, 2026

    7706 Country Place Unit A8, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,230 Sq Ft
    • Built 1984

    Last Sold Summary

    • 27% Below List Price
    • $154/SF
    • 447 Days On Market

    Current Estimated Value $225,244

    Last Listing Agent Carmen Vazquez REALTY TECH INC

    7706 Country Place Unit A8, 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 $355,816

    Last Listing Agent Julie Boyd-Elrod CHARLES RUTENBERG REALTY ORLANDO

    1690 Viburnum Ln, Winter Park, FL 32792
  • /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 $1,628,947

    Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

    279 Rippling Ln, 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 $9,836,079

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

    2203 Via Tuscany, Winter Park, FL 32789
  • /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 $458,168

    Last Listing Agent Alex Khalil EXP REALTY LLC

    5073 Lake Howell Rd, Winter Park, FL 32792
  • /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 $1,701,177

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

    2915 Parkland Dr, 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 $1,611,657

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

    1541 Chestnut Ave, 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 $685,791

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

    2904 Parkland Dr, Winter Park, FL 32789
  • /2

    $560,000

    Sold May 08, 2026

    218 Orange Terrace Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,618 Sq Ft
    • Built 1955

    Last Sold Summary

    • 12% Below List Price
    • $346/SF
    • 30 Days On Market

    Current Estimated Value $588,815

    Last Listing Agent Arden Magee ANNE ROGERS REALTY GROUP INC

    218 Orange Terrace Dr, Winter Park, FL 32789
  • /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 $87,366

    Last Listing Agent Tyann Huynh JADE KEY REALTY LLC

    110 Scottsdale Square, Winter Park, FL 32792
  • /2

    $610,000

    Sold Apr 13, 2026

    1860 Staunton Ave, Winter Park, FL 32789

    • Land
    • 13,503 Sq Ft
    • $1,967,742 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 9 Days On Market

    Current Estimated Value $636,278

    Last Listing Agent Leighton Hope COMPASS FLORIDA LLC

    1860 Staunton Ave, Winter Park, FL 32789
  • /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 $451,849

    Last Listing Agent Mary Dees CHOICEPOINTE REALTY, INC.

    2648 Amsden Rd, 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 $399,227

    Last Listing Agent Steve Dalton ROYALTY R E BOUTIQUE INC

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

    $277,000

    Sold Jun 24, 2026

    5450 Peaco Place, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • Built 1984

    Last Sold Summary

    • 1% Below List Price
    • $264/SF
    • 21 Days On Market

    Current Estimated Value $274,942

    Last Listing Agent Dean Gonzalez KELLER WILLIAMS ADVANTAGE 2 REALTY

    5450 Peaco Place, 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 $75,986

    Last Listing Agent Laura Hilton CHARLES RUTENBERG REALTY ORLANDO

    304 Scottsdale Square Unit L304, 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 $424,438

    Last Listing Agent Robert Kirkland Simply Real Estate

    2681 Tierra Cir, Winter Park, FL 32792
  • /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 $731,758

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    311 Cortland Ave, 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 $249,588

    Last Listing Agent Alayna Phillips EXP REALTY LLC

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

    $1,500,000

    Sold May 19, 2026

    246 Palmer Ave, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 2,281 Sq Ft
    • Built 1948

    Last Sold Summary

    • $658/SF
    • 2 Days On Market

    Current Estimated Value $1,482,493

    Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

    246 Palmer Ave, Winter Park, FL 32789
  • /2

    $490,000

    Sold Apr 23, 2026

    2126 N Hampton Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,745 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Below List Price
    • $281/SF
    • 6 Days On Market

    Current Estimated Value $489,168

    Last Listing Agent Joseph Sipp KELLER WILLIAMS WINTER PARK

    2126 N Hampton Cir, 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 $583,441

    Last Listing Agent Aaron Mighty MIGHTY REALTY INC

    1985 Japonica Rd, 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 $504,933

    Last Listing Agent Jennifer Draper REAL BROKER, LLC

    382 Perth Ln, Winter Park, FL 32792
  • /2

    $1,600,000

    Sold Apr 22, 2026

    446 Alberta Dr, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 3,263 Sq Ft
    • Built 1968

    Last Sold Summary

    • 12% Below List Price
    • $490/SF
    • 271 Days On Market

    Current Estimated Value $1,597,588

    Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

    446 Alberta Dr, Winter Park, FL 32789

Showing Results 201 - 240, Page 6 of 18

How to Buy a Home How to Finance a Home How to Sell a Home