1,172

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

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Recently Sold Real Estate & Homes in Winter Park, FL

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