1,095

Recently Sold Winter Park, FL Homes

Section Image
  • 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 $1,261,823

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

    857 Brock St, Winter Park, FL 32789
  • 1098 Wildmeadow Run, Winter Park, FL 32792
    1098 Wildmeadow Run, 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 $622,346

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

    1098 Wildmeadow Run, Winter Park, FL 32792
  • 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 $354,195

    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 $1,594,198

    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 $9,621,387

    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 $444,490

    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 $1,997,131

    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 $1,580,564

    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 $685,156

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

    2904 Parkland Dr, Winter Park, FL 32789
  • 218 Orange Terrace Dr, Winter Park, FL 32789
    218 Orange Terrace 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 $613,911

    Last Listing Agent Arden Magee ANNE ROGERS REALTY GROUP INC

    218 Orange Terrace 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 $86,385

    Last Listing Agent Tyann Huynh JADE KEY REALTY LLC

    110 Scottsdale Square, Winter Park, FL 32792
  • 1860 Staunton Ave, Winter Park, FL 32789
    1860 Staunton Ave, Winter Park, FL 32789
    /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 $645,285

    Last Listing Agent Leighton Hope COMPASS FLORIDA LLC

    1860 Staunton Ave, Winter Park, FL 32789
  • 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 $437,821

    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 $389,599

    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 $544,815

    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 $75,579

    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 $411,870

    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 $711,409

    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 $251,164

    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 $421,275

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

    693 Minnesota Ave, Winter Park, FL 32789
  • 2126 N Hampton Cir, Winter Park, FL 32792
    2126 N Hampton Cir, Winter Park, FL 32792
    /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 $493,926

    Last Listing Agent Joseph Sipp KELLER WILLIAMS WINTER PARK

    2126 N Hampton Cir, Winter Park, FL 32792
  • 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 $587,316

    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 $496,784

    Last Listing Agent Jennifer Draper REAL BROKER, LLC

    382 Perth Ln, Winter Park, FL 32792
  • 446 Alberta Dr, Winter Park, FL 32789
    446 Alberta Dr, Winter Park, FL 32789
    /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

    Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

    446 Alberta Dr, Winter Park, FL 32789
  • 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

    Last Listing Agent Dean D Nikolic PMI PROPERTY ALLIANCE

    2936 Antique Oaks Cir Unit 71, 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 $522,202

    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 $307,085

    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 $4,739,331

    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 $77,785

    Last Listing Agent Alan Barbosa DALTON WADE INC

    347 Scottsdale Square Unit 347, Winter Park, FL 32792
  • 2152 Conifer Ave, Winter Park, FL 32792
    2152 Conifer Ave, Winter Park, FL 32792
    /2

    $427,500 Sold Mar 26, 2026

    2152 Conifer Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,694 Sq Ft
    • Built 1969

    Last Sold Summary

    • 10% Below List Price
    • $252/SF
    • 134 Days On Market

    Current Estimated Value $443,064

    Last Listing Agent Denise Korrey KORR REALTY CORP

    2152 Conifer Ave, 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 $284,758

    Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

    1727 Winter Green Blvd, Winter Park, FL 32792
  • 667 Dunblane Dr, Winter Park, FL 32792
    667 Dunblane Dr, Winter Park, FL 32792
    /2

    $925,000 Sold Mar 27, 2026

    667 Dunblane Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,017 Sq Ft
    • Built 1962

    Last Sold Summary

    • $459/SF
    • 1 Day On Market

    Current Estimated Value $879,330

    Last Listing Agent Paola Padovan PADOVAN REALTY CORP.

    667 Dunblane Dr, 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 $202,315

    Last Listing Agent Rick Brown KELLER WILLIAMS ADVANTAGE 2 REALTY

    4952 Tangerine Ave, 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

    Current Estimated Value $430,392

    Last Listing Agent Ken Pozek REAL BROKER, LLC

    5122 N Woodcrest Dr, Winter Park, FL 32792
  • 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

    Last Listing Agent Jordan Suglio BALDWIN PARK REALTY LLC

    2838 Wright Ave, Winter Park, FL 32789
  • 2827 Euston Rd, Winter Park, FL 32789
    2827 Euston Rd, Winter Park, FL 32789
    /2

    $341,000 Sold Aug 08, 2025

    2827 Euston Rd, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • Built 1956

    Last Sold Summary

    • 20% Below List Price
    • $217/SF
    • 205 Days On Market

    Current Estimated Value $337,058

    Last Listing Agent Evelyn Tejada REGENCY REAL ESTATE LLC

    2827 Euston Rd, Winter Park, FL 32789
  • 731 Bongart Rd, Winter Park, FL 32792
    731 Bongart Rd, Winter Park, FL 32792
    /2

    $345,000 Sold Nov 03, 2025

    731 Bongart Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft
    • Built 1961

    Last Sold Summary

    • 5% Below List Price
    • $226/SF
    • 3 Days On Market

    Current Estimated Value $479,664

    Last Listing Agent Liz Jones ORANGE SLICE PROPERTIES

    731 Bongart Rd, Winter Park, FL 32792
  • 1602 Alabama Dr Unit 404, Winter Park, FL 32789
    1602 Alabama Dr Unit 404, Winter Park, FL 32789
    /2

    $2,288,215 Sold Dec 19, 2025

    1602 Alabama Dr Unit 404, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,709 Sq Ft
    • Built 1981

    Last Sold Summary

    • 8% Below List Price
    • $845/SF
    • 179 Days On Market

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1602 Alabama Dr Unit 404, Winter Park, FL 32789
  • 326 Fitzhugh Rd, Winter Park, FL 32792
    326 Fitzhugh Rd, Winter Park, FL 32792
    /2

    $502,000 Sold Feb 25, 2026

    326 Fitzhugh Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,835 Sq Ft
    • Built 1966

    Last Sold Summary

    • 6% Above List Price
    • $274/SF
    • 4 Days On Market

    Current Estimated Value $485,843

    Last Listing Agent Rebecca Bininger Junod KELLER WILLIAMS WINTER PARK

    326 Fitzhugh Rd, Winter Park, FL 32792
  • 3060 George Mason Ave Unit 10, Winter Park, FL 32792
    3060 George Mason Ave Unit 10, Winter Park, FL 32792
    /2

    $90,500 Sold Mar 10, 2026

    3060 George Mason Ave Unit 10, Winter Park, FL 32792

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

    Last Sold Summary

    • 14% Below List Price
    • $113/SF
    • 54 Days On Market

    Last Listing Agent John Silva JOHN SILVA REALTY & ASSOCIATES

    3060 George Mason Ave Unit 10, Winter Park, FL 32792

Showing Results 201 - 240, Page 6 of 18

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