1,174

Recently Sold Winter Park, FL Homes

Section Image
  • 1900 W Fawsett Rd, Winter Park, FL 32789
    1900 W Fawsett Rd, Winter Park, FL 32789
    /2

    $3,200,000 Sold Nov 04, 2025

    1900 W Fawsett Rd, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 4,600 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $696/SF
    • 6 Days On Market

    Last Listing Agent Bianca Rey KELLER WILLIAMS WINTER PARK

    1900 W Fawsett Rd, Winter Park, FL 32789
  • 2248 Middleton Ave, Winter Park, FL 32792
    2248 Middleton Ave, Winter Park, FL 32792
    /2

    $1,850,000 Sold Apr 07, 2025

    2248 Middleton Ave, Winter Park, FL 32792

    • 4 Beds
    • 4.5 Baths
    • 3,505 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $528/SF
    • 10 Days On Market

    Current Estimated Value $1,806,733

    Last Listing Agent Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

    2248 Middleton Ave, Winter Park, FL 32792
  • 5142 Tangerine Ave, Winter Park, FL 32792
    5142 Tangerine Ave, Winter Park, FL 32792
    /2

    $428,000 Sold Jan 21, 2025

    5142 Tangerine Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,563 Sq Ft
    • Built 1973

    Last Sold Summary

    • 1% Above List Price
    • $274/SF
    • 5 Days On Market

    Current Estimated Value $423,797

    Last Listing Agent Lorry Robles EXP REALTY LLC

    5142 Tangerine Ave, Winter Park, FL 32792
  • 451 Fairfax Ave, Winter Park, FL 32789
    451 Fairfax Ave, Winter Park, FL 32789
    /2

    $879,000 Sold Nov 14, 2025

    451 Fairfax Ave, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft
    • Built 2003

    Last Sold Summary

    • 2% Below List Price
    • $395/SF
    • 5 Days On Market

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

    451 Fairfax Ave, Winter Park, FL 32789
  • 1792 Killarney Dr, Winter Park, FL 32789
    1792 Killarney Dr, Winter Park, FL 32789
    /2

    $630,000 Sold Aug 11, 2025

    1792 Killarney Dr, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,264 Sq Ft
    • Built 1958

    Last Sold Summary

    • 3% Below List Price
    • $278/SF
    • 1 Day On Market

    Current Estimated Value $633,705

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    1792 Killarney Dr, Winter Park, FL 32789
  • 1909 Edwin Blvd, Winter Park, FL 32792
    1909 Edwin Blvd, Winter Park, FL 32792
    /2

    $382,000 Sold Jul 02, 2025

    1909 Edwin Blvd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,355 Sq Ft
    • Built 1955

    Last Sold Summary

    • 7% Below List Price
    • $282/SF
    • 34 Days On Market

    Last Listing Agent Brian Craib OLDE TOWN BROKERS INC

    1909 Edwin Blvd, Winter Park, FL 32792
  • 1005 Fairway Dr, Winter Park, FL 32792
    1005 Fairway Dr, Winter Park, FL 32792
    /2

    $785,000 Sold Dec 30, 2024

    1005 Fairway Dr, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,584 Sq Ft
    • Built 1973

    Last Sold Summary

    • 13% Below List Price
    • $304/SF
    • 141 Days On Market

    Current Estimated Value $790,711

    Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

    1005 Fairway Dr, Winter Park, FL 32792
  • 3002 George Mason Ave Unit 3, Winter Park, FL 32792
    3002 George Mason Ave Unit 3, Winter Park, FL 32792
    /2

    $89,750 Sold Dec 05, 2025

    3002 George Mason Ave Unit 3, Winter Park, FL 32792

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

    Last Sold Summary

    • 25% Below List Price
    • $83/SF
    • 92 Days On Market

    Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

    3002 George Mason Ave Unit 3, Winter Park, FL 32792
  • 1000 Howell Branch Rd, Winter Park, FL 32789
    1000 Howell Branch Rd, Winter Park, FL 32789
    /2

    $755,000 Sold Jul 18, 2025

    1000 Howell Branch Rd, Winter Park, FL 32789

    • Land
    • 0.55 Acre
    • $1,372,727 per Acre

    Last Sold Summary

    • 30% Below List Price
    • 241 Days On Market

    Current Estimated Value $855,172

    Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1000 Howell Branch Rd, Winter Park, FL 32789
  • 3358 Cedar Springs Place Unit 159, Winter Park, FL 32792
    3358 Cedar Springs Place Unit 159, Winter Park, FL 32792
    /2

    $150,000 Sold Mar 18, 2025

    3358 Cedar Springs Place Unit 159, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft
    • Built 1984

    Last Sold Summary

    • 33% Below List Price
    • $145/SF
    • 59 Days On Market

    Current Estimated Value $156,606

    Last Listing Agent Ali Khaku, MBA DALTON WADE INC

    3358 Cedar Springs Place Unit 159, Winter Park, FL 32792
  • 2020 Venetian Way, Winter Park, FL 32789
    2020 Venetian Way, Winter Park, FL 32789
    /2

    $3,845,000 Sold May 16, 2025

    2020 Venetian Way, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 4,188 Sq Ft
    • Built 1979

    Last Sold Summary

    • 4% Below List Price
    • $918/SF
    • 4 Days On Market

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

    2020 Venetian Way, Winter Park, FL 32789
  • 200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
    /2

    $130,000 Sold Nov 25, 2025

    200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 727 Sq Ft
    • Built 1970

    Last Sold Summary

    • 13% Below List Price
    • $179/SF
    • 35 Days On Market

    Last Listing Agent Mary Marwick PREMIUM PROPERTIES R.E SERVICE

    200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
  • 200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
    /2

    $170,000 Sold Sep 24, 2025

    200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft
    • Built 1970

    Last Sold Summary

    • 10% Below List Price
    • $152/SF
    • 74 Days On Market

    Last Listing Agent Evelyn Pilchick RE/MAX 200 REALTY

    200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
  • 200 Saint Andrews Blvd Unit 2502, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 2502, Winter Park, FL 32792
    /2

    $240,000 Sold Mar 03, 2025

    200 Saint Andrews Blvd Unit 2502, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,165 Sq Ft
    • Built 1970

    Last Sold Summary

    • 26% Below List Price
    • $206/SF
    • 217 Days On Market

    Current Estimated Value $236,184

    Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    200 Saint Andrews Blvd Unit 2502, Winter Park, FL 32792
  • 260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
    /2

    $325,000 Sold Oct 03, 2025

    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $285/SF
    • 0 Days On Market

    Last Listing Agent Tyler Gibson LPT REALTY, LLC

    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
  • 3063 Ash Park Loop, Winter Park, FL 32792
    3063 Ash Park Loop, Winter Park, FL 32792
    /2

    $415,000 Sold Jun 10, 2025

    3063 Ash Park Loop, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,673 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Below List Price
    • $248/SF
    • 23 Days On Market

    Current Estimated Value $420,801

    Last Listing Agent Cheryl Anderson ANDERSON INVESTMENT PROPERTIES

    3063 Ash Park Loop, Winter Park, FL 32792
  • 4421 Steed Terrace, Winter Park, FL 32792
    4421 Steed Terrace, Winter Park, FL 32792
    /2

    $385,000 Sold Nov 12, 2025

    4421 Steed Terrace, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,788 Sq Ft
    • Built 1989

    Last Sold Summary

    • 14% Below List Price
    • $215/SF
    • 209 Days On Market

    Last Listing Agent Andrey Bustamante BUSTAMANTE REAL ESTATE INC

    4421 Steed Terrace, Winter Park, FL 32792
  • 2817 Prince John Rd, Winter Park, FL 32792
    2817 Prince John Rd, Winter Park, FL 32792
    /2

    $665,000 Sold Jun 18, 2025

    2817 Prince John Rd, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 2,183 Sq Ft
    • Built 1963

    Last Sold Summary

    • 5% Below List Price
    • $305/SF
    • 37 Days On Market

    Current Estimated Value $655,084

    Last Listing Agent Lori Gilmore LORI GILMORE REAL ESTATE LLC

    2817 Prince John Rd, Winter Park, FL 32792
  • 255 Stirling Ave, Winter Park, FL 32789
    255 Stirling Ave, Winter Park, FL 32789
    /2

    $2,835,000 Sold Nov 24, 2025

    255 Stirling Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,635 Sq Ft
    • Built 1982

    Last Sold Summary

    • 14% Below List Price
    • $780/SF
    • 25 Days On Market

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

    255 Stirling Ave, Winter Park, FL 32789
  • 1011 Mckean Cir, Winter Park, FL 32789
    1011 Mckean Cir, Winter Park, FL 32789
    /2

    $1,430,000 Sold Nov 10, 2025

    1011 Mckean Cir, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,230 Sq Ft
    • Built 1955

    Last Sold Summary

    • $641/SF
    • 0 Days On Market

    Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

    1011 Mckean Cir, Winter Park, FL 32789
  • 1945 Bering Ave, Winter Park, FL 32789
    1945 Bering Ave, Winter Park, FL 32789
    /2

    $439,900 Sold Jul 22, 2025

    1945 Bering Ave, Winter Park, FL 32789

    • 3 Beds
    • 1.5 Baths
    • 1,576 Sq Ft
    • Built 1958

    Last Sold Summary

    • $279/SF
    • 6 Days On Market

    Current Estimated Value $434,268

    Last Listing Agent Carmen Gonzalez, Pa HORIZON WEST REALTY

    1945 Bering Ave, Winter Park, FL 32789
  • Unlisted Address
    Unlisted Address
    /2

    $799,000 Sold Apr 08, 2025

    Unlisted Address

    • 3 Beds
    • 2.5 Baths
    • 2,331 Sq Ft
    • Built 1952

    Last Sold Summary

    • $343/SF
    • 3 Days On Market

    Current Estimated Value $833,747

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

    Unlisted Address
  • 2494 Timberline Dr, Winter Park, FL 32792
    2494 Timberline Dr, Winter Park, FL 32792
    /2

    $227,100 Sold Jan 21, 2025

    2494 Timberline Dr, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Built 1980

    Last Sold Summary

    • 9% Below List Price
    • $173/SF
    • 57 Days On Market

    Current Estimated Value $242,027

    Last Listing Agent Crystal Whitehead CREEGAN GROUP

    2494 Timberline Dr, Winter Park, FL 32792
  • 222 Balfour Dr Unit 14, Winter Park, FL 32792
    222 Balfour Dr Unit 14, Winter Park, FL 32792
    /2

    $299,000 Sold Jan 08, 2025

    222 Balfour Dr Unit 14, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,256 Sq Ft
    • Built 1985

    Last Sold Summary

    • 12% Below List Price
    • $238/SF
    • 206 Days On Market

    Current Estimated Value $301,907

    Last Listing Agent Tricia Ramsby BHHS FLORIDA REALTY

    222 Balfour Dr Unit 14, Winter Park, FL 32792
  • 5173 Lazy Oaks Dr, Winter Park, FL 32792
    5173 Lazy Oaks Dr, Winter Park, FL 32792
    /2

    $285,000 Sold Jan 23, 2025

    5173 Lazy Oaks Dr, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,236 Sq Ft
    • Built 1984

    Last Sold Summary

    • 5% Below List Price
    • $231/SF
    • 107 Days On Market

    Current Estimated Value $281,012

    Last Listing Agent Kathleen Harrison CALL IT CLOSED INTL REALTY

    5173 Lazy Oaks Dr, Winter Park, FL 32792
  • 1847 Azalea Ave, Winter Park, FL 32789
    1847 Azalea Ave, Winter Park, FL 32789
    /2

    $400,000 Sold Dec 31, 2024

    1847 Azalea Ave, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 1,477 Sq Ft
    • Built 1961

    Last Sold Summary

    • 5% Below List Price
    • $271/SF
    • 93 Days On Market

    Last Listing Agent Dylan Pino REALTY HUB

    1847 Azalea Ave, Winter Park, FL 32789
  • 1341 Place Picardy, Winter Park, FL 32789
    1341 Place Picardy, Winter Park, FL 32789
    /2

    $2,575,000 Sold Oct 20, 2025

    1341 Place Picardy, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,469 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $576/SF
    • 95 Days On Market

    Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

    1341 Place Picardy, Winter Park, FL 32789
  • 5134 Lake Howell Rd, Winter Park, FL 32792
    5134 Lake Howell Rd, Winter Park, FL 32792
    /2

    $340,000 Sold Feb 12, 2025

    5134 Lake Howell Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,399 Sq Ft
    • Built 1957

    Last Sold Summary

    • $243/SF
    • 8 Days On Market

    Current Estimated Value $339,719

    Last Listing Agent Dawn Tinder KELLER WILLIAMS WINTER PARK

    5134 Lake Howell Rd, Winter Park, FL 32792
  • 2209 Fairglenn Way, Winter Park, FL 32792
    2209 Fairglenn Way, Winter Park, FL 32792
    /2

    $435,000 Sold Aug 31, 2025

    2209 Fairglenn Way, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,027 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Below List Price
    • $215/SF
    • 54 Days On Market

    Current Estimated Value $443,809

    Last Listing Agent Benjamin Benami HIVE REALTY LLC

    2209 Fairglenn Way, Winter Park, FL 32792
  • 193 Overlook Rd, Winter Park, FL 32789
    193 Overlook Rd, Winter Park, FL 32789
    /2

    $1,000,000 Sold Feb 18, 2025

    193 Overlook Rd, Winter Park, FL 32789

    • 3 Beds
    • 1.5 Baths
    • 2,201 Sq Ft
    • Built 1925

    Last Sold Summary

    • 17% Below List Price
    • $454/SF
    • 44 Days On Market

    Current Estimated Value $1,000,691

    Last Listing Agent Kimberley Gernert BALDWIN PARK REALTY LLC

    193 Overlook Rd, Winter Park, FL 32789
  • 200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
    /2

    $242,000 Sold Oct 15, 2025

    200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792

    • 2 Beds
    • 1.5 Baths
    • 1,219 Sq Ft
    • Built 1970

    Last Sold Summary

    • 9% Below List Price
    • $199/SF
    • 125 Days On Market

    Last Listing Agent Jessica Geer A+ REALTY PROFESSIONALS, INC

    200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
  • 4200 Bear Gully Rd, Winter Park, FL 32792
    4200 Bear Gully Rd, Winter Park, FL 32792
    /2

    $535,000 Sold May 28, 2025

    4200 Bear Gully Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,945 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $275/SF
    • 35 Days On Market

    Current Estimated Value $534,619

    Last Listing Agent Renee Killiri RED BIRD REALTY OF FLORIDA INC

    4200 Bear Gully Rd, Winter Park, FL 32792
  • 4991 Tangerine Ave, Winter Park, FL 32792
    4991 Tangerine Ave, Winter Park, FL 32792
    /2

    $528,000 Sold Nov 25, 2025

    4991 Tangerine Ave, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,124 Sq Ft
    • Built 1972

    Last Sold Summary

    • $249/SF
    • 5 Days On Market

    Last Listing Agent Edwin Ayala, Jr EXP REALTY LLC

    4991 Tangerine Ave, Winter Park, FL 32792
  • 830 W Canton Ave, Winter Park, FL 32789
    830 W Canton Ave, Winter Park, FL 32789
    /2

    $900,000 Sold Feb 18, 2025

    830 W Canton Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,965 Sq Ft
    • Built 2018

    Last Sold Summary

    • 6% Below List Price
    • $458/SF
    • 14 Days On Market

    Current Estimated Value $919,350

    Last Listing Agent Claudia Kester FOLIO REALTY LLC

    830 W Canton Ave, Winter Park, FL 32789
  • 927 Mare Bello Dr, Winter Park, FL 32792
    927 Mare Bello Dr, Winter Park, FL 32792
    /2

    $250,000 Sold Dec 27, 2024

    927 Mare Bello Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,327 Sq Ft
    • Built 1965

    Last Sold Summary

    • 17% Below List Price
    • $188/SF
    • 14 Days On Market

    Current Estimated Value $386,206

    Last Listing Agent Patricia Sierra EXP REALTY LLC

    927 Mare Bello Dr, Winter Park, FL 32792
  • 151 N Orlando Ave Unit 142, Winter Park, FL 32789
    151 N Orlando Ave Unit 142, Winter Park, FL 32789
    /2

    $140,000 Sold Apr 14, 2025

    151 N Orlando Ave Unit 142, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 582 Sq Ft
    • Built 1960

    Last Sold Summary

    • 33% Below List Price
    • $241/SF
    • 152 Days On Market

    Current Estimated Value $159,574

    Last Listing Agent TOM NOELKE EXP REALTY LLC

    151 N Orlando Ave Unit 142, Winter Park, FL 32789
  • 419 W Morse Blvd, Winter Park, FL 32789
    419 W Morse Blvd, Winter Park, FL 32789
    /2

    $1,850,000 Sold Dec 15, 2025

    419 W Morse Blvd, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 3,027 Sq Ft
    • Built 2018

    Last Sold Summary

    • 5% Below List Price
    • $611/SF
    • 0 Days On Market

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

    419 W Morse Blvd, Winter Park, FL 32789
  • 2259 Minnesota Ave, Winter Park, FL 32789
    2259 Minnesota Ave, Winter Park, FL 32789
    /2

    $375,000 Sold Apr 28, 2025

    2259 Minnesota Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,015 Sq Ft
    • Built 1948

    Last Sold Summary

    • 10% Below List Price
    • $369/SF
    • 11 Days On Market

    Current Estimated Value $375,453

    Last Listing Agent Kayla Barnes LPT REALTY, LLC

    2259 Minnesota Ave, Winter Park, FL 32789
  • 2172 Temple Dr, Winter Park, FL 32789
    2172 Temple Dr, Winter Park, FL 32789
    /2

    $2,300,000 Sold Feb 04, 2025

    2172 Temple Dr, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 3,467 Sq Ft
    • Built 2024

    Last Sold Summary

    • 3% Above List Price
    • $663/SF
    • 0 Days On Market

    Current Estimated Value $2,281,569

    Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

    2172 Temple Dr, Winter Park, FL 32789
  • 2920 Abbey Ct, Winter Park, FL 32792
    2920 Abbey Ct, Winter Park, FL 32792
    /2

    $470,000 Sold Aug 21, 2025

    2920 Abbey Ct, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,035 Sq Ft
    • Built 1964

    Last Sold Summary

    • 6% Below List Price
    • $231/SF
    • 2 Days On Market

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    2920 Abbey Ct, Winter Park, FL 32792

Showing Results 161 - 200, Page 5 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group