1,172

Recently Sold Winter Park, FL Homes

Section Image
  • 4048 Gilder Rose Place, Winter Park, FL 32792
    4048 Gilder Rose Place, Winter Park, FL 32792
    /2

    $1,206,400 Sold Oct 15, 2025

    4048 Gilder Rose Place, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,321 Sq Ft
    • Built 1992

    Last Sold Summary

    • $363/SF
    • 101 Days On Market

    Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

    4048 Gilder Rose Place, Winter Park, FL 32792
  • 273 Scottsdale Square Unit 273, Winter Park, FL 32792
    273 Scottsdale Square Unit 273, Winter Park, FL 32792
    /2

    $72,000 Sold Jun 24, 2025

    273 Scottsdale Square Unit 273, Winter Park, FL 32792

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

    Last Sold Summary

    • 24% Below List Price
    • $92/SF
    • 4 Days On Market

    Current Estimated Value $79,788

    Last Listing Agent Erin Tompkins COLDWELL BANKER RESIDENTIAL RE

    273 Scottsdale Square Unit 273, Winter Park, FL 32792
  • 2732 Lion Heart Rd, Winter Park, FL 32792
    2732 Lion Heart Rd, Winter Park, FL 32792
    /2

    $660,000 Sold May 23, 2025

    2732 Lion Heart Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,975 Sq Ft
    • Built 1962

    Last Sold Summary

    • $334/SF
    • 2 Days On Market

    Current Estimated Value $648,867

    Last Listing Agent Sue Grafton FANNIE HILLMAN & ASSOCIATES

    2732 Lion Heart Rd, Winter Park, FL 32792
  • 1321 Medinah Ct, Winter Park, FL 32792
    1321 Medinah Ct, Winter Park, FL 32792
    /2

    $685,000 Sold May 27, 2025

    1321 Medinah Ct, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,446 Sq Ft
    • Built 1979

    Last Sold Summary

    • 9% Below List Price
    • $280/SF
    • 53 Days On Market

    Current Estimated Value $684,050

    Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

    1321 Medinah Ct, Winter Park, FL 32792
  • 5144 Goldenrod Place Rd, Winter Park, FL 32792
    5144 Goldenrod Place Rd, Winter Park, FL 32792
    /2

    $400,000 Sold May 29, 2025

    5144 Goldenrod Place Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Below List Price
    • $273/SF
    • 36 Days On Market

    Current Estimated Value $404,201

    Last Listing Agent Rebecca Sparks C. APOLLO REALTY INC

    5144 Goldenrod Place Rd, Winter Park, FL 32792
  • 1026 Manchester Cir, Winter Park, FL 32792
    1026 Manchester Cir, Winter Park, FL 32792
    /2

    $468,470 Sold Jun 20, 2025

    1026 Manchester Cir, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,724 Sq Ft
    • Built 1977

    Last Sold Summary

    • 3% Below List Price
    • $272/SF
    • 25 Days On Market

    Current Estimated Value $474,621

    Last Listing Agent David Miller KELLER WILLIAMS HERITAGE REALTY

    1026 Manchester Cir, Winter Park, FL 32792
  • 1006 Bradford Dr, Winter Park, FL 32792
    1006 Bradford Dr, Winter Park, FL 32792
    /2

    $430,000 Sold Aug 08, 2025

    1006 Bradford Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,130 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Above List Price
    • $202/SF
    • 7 Days On Market

    Current Estimated Value $431,297

    Last Listing Agent Paul Giannotti TERZA REAL ESTATE

    1006 Bradford Dr, Winter Park, FL 32792
  • 335 W Welbourne Ave Unit 103, Winter Park, FL 32789
    335 W Welbourne Ave Unit 103, Winter Park, FL 32789
    /2

    $1,242,000 Sold Feb 07, 2025

    335 W Welbourne Ave Unit 103, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 2,734 Sq Ft
    • Built 2008

    Last Sold Summary

    • 14% Below List Price
    • $454/SF
    • 184 Days On Market

    Current Estimated Value $1,241,199

    Last Listing Agent Gernelle Bokuniewicz LIVELY REAL ESTATE

    335 W Welbourne Ave Unit 103, Winter Park, FL 32789
  • 2235 Coldstream Dr, Winter Park, FL 32792
    2235 Coldstream Dr, Winter Park, FL 32792
    /2

    $715,000 Sold Jan 24, 2025

    2235 Coldstream Dr, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,347 Sq Ft
    • Built 2003

    Last Sold Summary

    • 13% Below List Price
    • $305/SF
    • 120 Days On Market

    Current Estimated Value $744,624

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    2235 Coldstream Dr, Winter Park, FL 32792
  • 1733 Harmon Ave, Winter Park, FL 32789
    1733 Harmon Ave, Winter Park, FL 32789
    /2

    $1,595,000 Sold Sep 02, 2025

    1733 Harmon Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,267 Sq Ft
    • Built 2025

    Last Sold Summary

    • $488/SF
    • 27 Days On Market

    Current Estimated Value $1,568,298

    Last Listing Agent Jordan Freeland SOUTH REALTY, INC

    1733 Harmon Ave, Winter Park, FL 32789
  • 627 Darcey Dr, Winter Park, FL 32792
    627 Darcey Dr, Winter Park, FL 32792
    /2

    $749,000 Sold Aug 13, 2025

    627 Darcey Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,509 Sq Ft
    • Built 1967

    Last Sold Summary

    • 6% Below List Price
    • $299/SF
    • 52 Days On Market

    Current Estimated Value $750,569

    Last Listing Agent Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

    627 Darcey Dr, Winter Park, FL 32792
  • 350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
    350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
    /2

    $380,000 Sold May 02, 2025

    350 Killarney Bay Ct Unit 5, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 1,428 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $266/SF
    • 42 Days On Market

    Current Estimated Value $390,177

    Last Listing Agent Dora Siler FOLIO REALTY LLC

    350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
  • 1450 Chestnut Ave, Winter Park, FL 32789
    1450 Chestnut Ave, Winter Park, FL 32789
    /2

    $1,095,000 Sold Dec 01, 2025

    1450 Chestnut Ave, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 1,942 Sq Ft
    • Built 2009

    Last Sold Summary

    • 16% Below List Price
    • $564/SF
    • 49 Days On Market

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1450 Chestnut Ave, Winter Park, FL 32789
  • 5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792
    5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792
    /2

    $260,000 Sold Feb 27, 2025

    5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1982

    Last Sold Summary

    • 5% Below List Price
    • $258/SF
    • 1 Day On Market

    Current Estimated Value $259,121

    Last Listing Agent Natalia Moege PARK 26 REALTY LLC

    5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792
  • 2855 Cady Way, Winter Park, FL 32792
    2855 Cady Way, Winter Park, FL 32792
    /2

    $538,500 Sold May 16, 2025

    2855 Cady Way, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Built 1964

    Last Sold Summary

    • 9% Below List Price
    • $310/SF
    • 76 Days On Market

    Current Estimated Value $533,536

    Last Listing Agent Joe Cremonese GLOBAL PROPERTIES SALES & MGMT

    2855 Cady Way, Winter Park, FL 32792
  • 2539 Antilles Dr, Winter Park, FL 32792
    2539 Antilles Dr, Winter Park, FL 32792
    /2

    $284,000 Sold May 23, 2025

    2539 Antilles Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $249/SF
    • 50 Days On Market

    Current Estimated Value $284,112

    Last Listing Agent Allie George CORCORAN PREMIER REALTY

    2539 Antilles Dr, Winter Park, FL 32792
  • 1102 Wildmeadow Run, Winter Park, FL 32792
    1102 Wildmeadow Run, Winter Park, FL 32792
    /2

    $730,000 Sold Dec 27, 2024

    1102 Wildmeadow Run, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 2,589 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Below List Price
    • $282/SF
    • 55 Days On Market

    Current Estimated Value $749,156

    Last Listing Agent Richard Palmano PALMANO GROUP RE BROKERAGE LLC

    1102 Wildmeadow Run, Winter Park, FL 32792
  • 7102 Easter St, Winter Park, FL 32792
    7102 Easter St, Winter Park, FL 32792
    /2

    $290,000 Sold Sep 22, 2025

    7102 Easter St, Winter Park, FL 32792

    • 3 Beds
    • 1 Bath
    • 1,114 Sq Ft
    • Built 1956

    Last Sold Summary

    • 3% Below List Price
    • $260/SF
    • 67 Days On Market

    Current Estimated Value $287,506

    Last Listing Agent Mayken Giraldo THE C SMITH REAL ESTATE GROUP LLC

    7102 Easter St, Winter Park, FL 32792
  • 1795 Walker Ave, Winter Park, FL 32789
    1795 Walker Ave, Winter Park, FL 32789
    /2

    $805,000 Sold Jul 01, 2025

    1795 Walker Ave, Winter Park, FL 32789

    • 5 Beds
    • 3 Baths
    • 1,813 Sq Ft
    • Built 1958

    Last Sold Summary

    • 17% Below List Price
    • $444/SF
    • 143 Days On Market

    Current Estimated Value $785,487

    Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

    1795 Walker Ave, Winter Park, FL 32789
  • 1010 Aragon Ave, Winter Park, FL 32789
    1010 Aragon Ave, Winter Park, FL 32789
    /2

    $567,500 Sold Dec 09, 2025

    1010 Aragon Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,453 Sq Ft
    • Built 1949

    Last Sold Summary

    • 1% Below List Price
    • $391/SF
    • 2 Days On Market

    Last Listing Agent Devin Loh COLDWELL BANKER RESIDENTIAL RE

    1010 Aragon Ave, Winter Park, FL 32789
  • 830 Overspin Dr, Winter Park, FL 32789
    830 Overspin Dr, Winter Park, FL 32789
    830 Overspin Dr, Winter Park, FL 32789
    /32

    $380,000 Sold Mar 07, 2025

    830 Overspin Dr, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,150 Sq Ft
    • Built 1952

    Last Sold Summary

    • 3% Below List Price
    • $330/SF
    • 30 Days On Market

    Current Estimated Value $371,986

    Last Listing Agent Richard Bavec TOLARIS REALTY GROUP LLC

    830 Overspin Dr, Winter Park, FL 32789
  • 223 Page St, Orlando, FL 32806
    223 Page St, Orlando, FL 32806
    /2

    $925,000 Sold Feb 19, 2025

    223 Page St, Orlando, FL 32806

    • 4 Beds
    • 3.5 Baths
    • 2,685 Sq Ft
    • Built 2024

    Last Sold Summary

    • 5% Below List Price
    • $345/SF
    • 143 Days On Market

    Current Estimated Value $875,485

    Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

    223 Page St, Orlando, FL 32806
  • 114 Scottsdale Square Unit 114, Winter Park, FL 32792
    114 Scottsdale Square Unit 114, Winter Park, FL 32792
    /2

    $118,000 Sold Dec 30, 2024

    114 Scottsdale Square Unit 114, Winter Park, FL 32792

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

    Last Sold Summary

    • 9% Below List Price
    • $109/SF
    • 7 Days On Market

    Current Estimated Value $113,399

    Last Listing Agent Jeffrey Filegar VIVA ORLANDO REALTY INC.

    114 Scottsdale Square Unit 114, Winter Park, FL 32792
  • 715 Via Bella, Winter Park, FL 32789
    715 Via Bella, Winter Park, FL 32789
    /2

    $2,078,500 Sold Dec 11, 2025

    715 Via Bella, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 4,328 Sq Ft
    • Built 1976

    Last Sold Summary

    • 12% Below List Price
    • $480/SF
    • 70 Days On Market

    Last Listing Agent Adam Roark COMPASS FLORIDA LLC

    715 Via Bella, Winter Park, FL 32789
  • 777 S Denning Dr Unit B, Winter Park, FL 32789
    777 S Denning Dr Unit B, Winter Park, FL 32789
    /2

    $602,500 Sold May 09, 2025

    777 S Denning Dr Unit B, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 1,762 Sq Ft
    • Built 2004

    Last Sold Summary

    • 6% Below List Price
    • $342/SF
    • 37 Days On Market

    Current Estimated Value $601,937

    Last Listing Agent Susan Chapin KELLER WILLIAMS WINTER PARK

    777 S Denning Dr Unit B, Winter Park, FL 32789
  • 1663 Meadowgold Ct, Winter Park, FL 32792
    1663 Meadowgold Ct, Winter Park, FL 32792
    /2

    $445,000 Sold Mar 20, 2025

    1663 Meadowgold Ct, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,851 Sq Ft
    • Built 1987

    Last Sold Summary

    • 11% Below List Price
    • $240/SF
    • 173 Days On Market

    Current Estimated Value $441,402

    Last Listing Agent Dallas Wittish ORLANDO REALTY & PROPERTY MGNT

    1663 Meadowgold Ct, Winter Park, FL 32792
  • 1122 Washington Ave Unit 7, Winter Park, FL 32789
    1122 Washington Ave Unit 7, Winter Park, FL 32789
    /2

    $434,000 Sold Sep 12, 2025

    1122 Washington Ave Unit 7, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 1,556 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Above List Price
    • $279/SF
    • 55 Days On Market

    Current Estimated Value $440,038

    Last Listing Agent Raul Veitia BELMONT REALTY

    1122 Washington Ave Unit 7, Winter Park, FL 32789
  • 2612 Parkland Dr, Winter Park, FL 32789
    2612 Parkland Dr, Winter Park, FL 32789
    /2

    $1,895,000 Sold Jan 22, 2025

    2612 Parkland Dr, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,282 Sq Ft
    • Built 2006

    Last Sold Summary

    • $577/SF
    • 9 Days On Market

    Current Estimated Value $1,896,821

    Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

    2612 Parkland Dr, Winter Park, FL 32789
  • 715 Roughbeard Rd, Winter Park, FL 32792
    715 Roughbeard Rd, Winter Park, FL 32792
    /2

    $505,000 Sold Aug 01, 2025

    715 Roughbeard Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,250 Sq Ft
    • Built 1968

    Last Sold Summary

    • 12% Below List Price
    • $224/SF
    • 60 Days On Market

    Current Estimated Value $520,478

    Last Listing Agent Christine Gerardi NEXTHOME DIAMOND PROPERTIES

    715 Roughbeard Rd, Winter Park, FL 32792
  • 2309 Sun Valley Cir, Winter Park, FL 32792
    2309 Sun Valley Cir, Winter Park, FL 32792
    /2

    $252,500 Sold Jul 17, 2025

    2309 Sun Valley Cir, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,669 Sq Ft
    • Built 1985

    Last Sold Summary

    • 11% Below List Price
    • $151/SF
    • 65 Days On Market

    Current Estimated Value $259,070

    Last Listing Agent Kristin Vogt CENTURY 21 INTEGRA

    2309 Sun Valley Cir, Winter Park, FL 32792
  • 3455 Athena Dr, Winter Park, FL 32792
    3455 Athena Dr, Winter Park, FL 32792
    /2

    $458,000 Sold Feb 25, 2025

    3455 Athena Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,161 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $212/SF
    • 135 Days On Market

    Current Estimated Value $462,398

    Last Listing Agent Stephanie Kovats KELLER WILLIAMS ADVANTAGE REALTY

    3455 Athena Dr, Winter Park, FL 32792
  • 1037 Fairway Dr, Winter Park, FL 32792
    1037 Fairway Dr, Winter Park, FL 32792
    /2

    $660,000 Sold Apr 14, 2025

    1037 Fairway Dr, Winter Park, FL 32792

    • 3 Beds
    • 3 Baths
    • 2,145 Sq Ft
    • Built 1978

    Last Sold Summary

    • 6% Below List Price
    • $308/SF
    • 29 Days On Market

    Current Estimated Value $656,043

    Last Listing Agent Skip Juma LEGACY REALTY & BROKERS LLC

    1037 Fairway Dr, Winter Park, FL 32792
  • 443 Lakewood Dr, Winter Park, FL 32789
    443 Lakewood Dr, Winter Park, FL 32789
    /2

    $3,550,000 Sold Mar 24, 2025

    443 Lakewood Dr, Winter Park, FL 32789

    • 3 Beds
    • 5 Baths
    • 2,803 Sq Ft
    • Built 1954

    Last Sold Summary

    • 1% Above List Price
    • $1,267/SF
    • 0 Days On Market

    Current Estimated Value $3,401,343

    Last Listing Agent Jenny Lake FANNIE HILLMAN & ASSOCIATES

    443 Lakewood Dr, Winter Park, FL 32789
  • 541 London Rd, Winter Park, FL 32792
    541 London Rd, Winter Park, FL 32792
    /2

    $468,000 Sold Aug 28, 2025

    541 London Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,899 Sq Ft
    • Built 1965

    Last Sold Summary

    • $246/SF
    • 8 Days On Market

    Current Estimated Value $476,047

    Last Listing Agent Christopher Bauman REVEL REALTY LLC

    541 London Rd, Winter Park, FL 32792
  • 350 Carolina Ave Unit 301, Winter Park, FL 32789
    350 Carolina Ave Unit 301, Winter Park, FL 32789
    350 Carolina Ave Unit 301, Winter Park, FL 32789
    /51

    $704,700 Sold Mar 11, 2025

    350 Carolina Ave Unit 301, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • $456/SF
    • 26 Days On Market

    Current Estimated Value $706,914

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    350 Carolina Ave Unit 301, Winter Park, FL 32789
  • 7706 Waunatta Ct, Winter Park, FL 32792
    7706 Waunatta Ct, Winter Park, FL 32792
    /2

    $935,000 Sold Dec 19, 2025

    7706 Waunatta Ct, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 3,858 Sq Ft
    • Built 1978

    Last Sold Summary

    • 11% Below List Price
    • $242/SF
    • 70 Days On Market

    Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

    7706 Waunatta Ct, Winter Park, FL 32792
  • 233 Hampden Place, Winter Park, FL 32789
    233 Hampden Place, Winter Park, FL 32789
    /2

    $1,110,000 Sold Aug 26, 2025

    233 Hampden Place, Winter Park, FL 32789

    • 5 Beds
    • 3 Baths
    • 2,813 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Below List Price
    • $395/SF
    • 7 Days On Market

    Current Estimated Value $1,161,867

    Last Listing Agent Frank Ferrell FERRELL REALTY, INC.

    233 Hampden Place, Winter Park, FL 32789
  • 3251 Oak Lake Place Unit 135, Winter Park, FL 32792
    3251 Oak Lake Place Unit 135, Winter Park, FL 32792
    /2

    $200,000 Sold Sep 13, 2025

    3251 Oak Lake Place Unit 135, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft
    • Built 1984

    Last Sold Summary

    • 11% Below List Price
    • $174/SF
    • 131 Days On Market

    Current Estimated Value $201,614

    Last Listing Agent Nick Nesta, III NESTA REAL ESTATE CONSULTANTS

    3251 Oak Lake Place Unit 135, Winter Park, FL 32792
  • 2435 Chantilly Ave, Winter Park, FL 32789
    2435 Chantilly Ave, Winter Park, FL 32789
    /2

    $1,575,000 Sold Dec 27, 2024

    2435 Chantilly Ave, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,055 Sq Ft
    • Built 2023

    Last Sold Summary

    • 5% Below List Price
    • $516/SF
    • 42 Days On Market

    Current Estimated Value $1,580,443

    Last Listing Agent Aleksey Volchek FLORIDA REALTY INVESTMENTS

    2435 Chantilly Ave, Winter Park, FL 32789
  • 2690 Granada Run, Winter Park, FL 32792
    2690 Granada Run, Winter Park, FL 32792
    /2

    $292,000 Sold Feb 28, 2025

    2690 Granada Run, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Below List Price
    • $199/SF
    • 33 Days On Market

    Current Estimated Value $294,845

    Last Listing Agent Jacquie Sosa EXP REALTY LLC

    2690 Granada Run, Winter Park, FL 32792

Showing Results 121 - 160, Page 4 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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