1,095

Recently Sold Winter Park, FL Homes

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  • 747 Mcintyre Ave, Winter Park, FL 32789
    747 Mcintyre Ave, Winter Park, FL 32789
    /2

    $1,525,000 Sold Jun 18, 2025

    747 Mcintyre Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,457 Sq Ft
    • Built 1950

    Last Sold Summary

    • 2% Above List Price
    • $1,047/SF
    • 2 Days On Market

    Current Estimated Value $1,438,122

    Last Listing Agent Chuck Massab FANNIE HILLMAN & ASSOCIATES

    747 Mcintyre Ave, Winter Park, FL 32789
  • 3490 Bougainvillea Dr, Winter Park, FL 32792
    3490 Bougainvillea Dr, Winter Park, FL 32792
    /2

    $332,000 Sold Oct 20, 2025

    3490 Bougainvillea Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,461 Sq Ft
    • Built 1960

    Last Sold Summary

    • 12% Below List Price
    • $227/SF
    • 39 Days On Market

    Current Estimated Value $333,121

    Last Listing Agent EJ Jimenez KELLER WILLIAMS ADVANTAGE III

    3490 Bougainvillea Dr, Winter Park, FL 32792
  • 463 Warrenton Rd Unit 463, Winter Park, FL 32792
    463 Warrenton Rd Unit 463, Winter Park, FL 32792
    /2

    $270,000 Sold Jul 17, 2025

    463 Warrenton Rd Unit 463, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,043 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Below List Price
    • $259/SF
    • 20 Days On Market

    Current Estimated Value $250,247

    Last Listing Agent Jenny Lake FANNIE HILLMAN & ASSOCIATES

    463 Warrenton Rd Unit 463, Winter Park, FL 32792
  • 5575 Garden Grove Cir, Winter Park, FL 32792
    5575 Garden Grove Cir, Winter Park, FL 32792
    /2

    $415,000 Sold Jul 17, 2025

    5575 Garden Grove Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,414 Sq Ft
    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • $293/SF
    • 15 Days On Market

    Current Estimated Value $416,711

    Last Listing Agent Torey Eisenman BENCHMARK REAL ESTATE GRP INC

    5575 Garden Grove Cir, Winter Park, FL 32792
  • 2743 Merrie Oaks Rd, Winter Park, FL 32792
    2743 Merrie Oaks Rd, Winter Park, FL 32792
    /2

    $445,000 Sold Jan 22, 2026

    2743 Merrie Oaks Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,661 Sq Ft
    • Built 1966

    Last Sold Summary

    • 1% Above List Price
    • $268/SF
    • 9 Days On Market

    Last Listing Agent Julio Zayas ONE45 REALTY LLC

    2743 Merrie Oaks Rd, Winter Park, FL 32792
  • 1560 Woodland Ave, Winter Park, FL 32789
    1560 Woodland Ave, Winter Park, FL 32789
    /2

    $1,675,000 Sold May 08, 2026

    1560 Woodland Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,851 Sq Ft
    • Built 1990

    Last Sold Summary

    • 9% Below List Price
    • $435/SF
    • 16 Days On Market

    Current Estimated Value $1,823,155

    Last Listing Agent Chris Creegan CREEGAN GROUP

    1560 Woodland Ave, Winter Park, FL 32789
  • 1183 Wildmeadow Run, Winter Park, FL 32792
    1183 Wildmeadow Run, Winter Park, FL 32792
    /2

    $800,000 Sold Apr 13, 2026

    1183 Wildmeadow Run, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,020 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Below List Price
    • $265/SF
    • 43 Days On Market

    Current Estimated Value $822,565

    Last Listing Agent Kara Lushear COLDWELL BANKER REALTY

    1183 Wildmeadow Run, Winter Park, FL 32792
  • 1116 Fairway Dr, Winter Park, FL 32792
    1116 Fairway Dr, Winter Park, FL 32792
    /2

    $455,000 Sold Dec 29, 2025

    1116 Fairway Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,738 Sq Ft
    • Built 1978

    Last Sold Summary

    • 24% Below List Price
    • $262/SF
    • 333 Days On Market

    Current Estimated Value $465,190

    Last Listing Agent Mathew Kelly TURN-KEY MOVES REALTY

    1116 Fairway Dr, Winter Park, FL 32792
  • 660 Osceola Ave Unit 101, Winter Park, FL 32789
    660 Osceola Ave Unit 101, Winter Park, FL 32789
    /2

    $2,232,000 Sold Apr 17, 2026

    660 Osceola Ave Unit 101, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,714 Sq Ft
    • Built 1999

    Last Sold Summary

    • 3% Below List Price
    • $822/SF
    • 145 Days On Market

    Current Estimated Value $2,149,386

    Last Listing Agent Richard Traynor FLORIDA ONE REAL ESTATE LLC

    660 Osceola Ave Unit 101, Winter Park, FL 32789
  • 200 Saint Andrews Blvd Unit 1004, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 1004, Winter Park, FL 32792
    /2

    $250,000 Sold Oct 06, 2025

    200 Saint Andrews Blvd Unit 1004, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,322 Sq Ft
    • Built 1970

    Last Sold Summary

    • 17% Below List Price
    • $189/SF
    • 157 Days On Market

    Current Estimated Value $245,965

    Last Listing Agent Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

    200 Saint Andrews Blvd Unit 1004, Winter Park, FL 32792
  • 1313 S Denning Dr, Winter Park, FL 32789
    1313 S Denning Dr, Winter Park, FL 32789
    /2

    $300,000 Sold Mar 27, 2026

    1313 S Denning Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 1950

    Last Sold Summary

    • $176/SF

    Current Estimated Value $454,086

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

    1313 S Denning Dr, Winter Park, FL 32789
  • 611 Ololu Dr, Winter Park, FL 32789
    611 Ololu Dr, Winter Park, FL 32789
    /2

    $360,000 Sold Nov 20, 2025

    611 Ololu Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,145 Sq Ft
    • Built 1973

    Last Sold Summary

    • 1% Above List Price
    • $314/SF
    • 7 Days On Market

    Current Estimated Value $359,992

    Last Listing Agent Amanda Johnson HOMERUN REALTY, LLC

    611 Ololu Dr, Winter Park, FL 32789
  • 2652 Lake Howell Ln, Winter Park, FL 32792
    2652 Lake Howell Ln, Winter Park, FL 32792
    /2

    $2,500,000 Sold Oct 31, 2025

    2652 Lake Howell Ln, Winter Park, FL 32792

    • 5 Beds
    • 3.5 Baths
    • 3,898 Sq Ft
    • Built 1954

    Last Sold Summary

    • 12% Below List Price
    • $641/SF
    • 64 Days On Market

    Current Estimated Value $2,201,012

    Last Listing Agent Brigitte Elzarki COLDWELL BANKER REALTY

    2652 Lake Howell Ln, Winter Park, FL 32792
  • 2232 Shadowland Loop, Winter Park, FL 32792
    2232 Shadowland Loop, Winter Park, FL 32792
    /2

    $385,000 Sold Apr 21, 2026

    2232 Shadowland Loop, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft
    • Built 2021

    Last Sold Summary

    • 10% Below List Price
    • $219/SF
    • 77 Days On Market

    Current Estimated Value $404,166

    Last Listing Agent He Gao U S GLORY REALTY

    2232 Shadowland Loop, Winter Park, FL 32792
  • 507 Country Club Dr, Winter Park, FL 32789
    507 Country Club Dr, Winter Park, FL 32789
    /2

    $1,535,000 Sold Mar 30, 2026

    507 Country Club Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,985 Sq Ft
    • Built 2020

    Last Sold Summary

    • 1% Below List Price
    • $514/SF
    • 27 Days On Market

    Current Estimated Value $1,535,586

    Last Listing Agent Lianna D'Angelo SOTERA LIVING

    507 Country Club Dr, Winter Park, FL 32789
  • 210 E Rockwood Way, Winter Park, FL 32789
    210 E Rockwood Way, Winter Park, FL 32789
    /2

    $1,000,500 Sold Dec 11, 2025

    210 E Rockwood Way, Winter Park, FL 32789

    • 3 Beds
    • 1.5 Baths
    • 1,431 Sq Ft
    • Built 1950

    Last Sold Summary

    • $699/SF
    • 0 Days On Market

    Current Estimated Value $968,531

    Last Listing Agent Penny Puente DALTON WADE INC

    210 E Rockwood Way, Winter Park, FL 32789
  • 5128 Lake Howell Rd, Winter Park, FL 32792
    5128 Lake Howell Rd, Winter Park, FL 32792
    /2

    $350,000 Sold Oct 22, 2025

    5128 Lake Howell Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,220 Sq Ft
    • Built 1957

    Last Sold Summary

    • $287/SF
    • 12 Days On Market

    Current Estimated Value $342,268

    Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

    5128 Lake Howell Rd, Winter Park, FL 32792
  • 1267 Michigan Ave, Winter Park, FL 32789
    1267 Michigan Ave, Winter Park, FL 32789
    /2

    $555,000 Sold Jan 29, 2026

    1267 Michigan Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,798 Sq Ft
    • Built 2019

    Last Sold Summary

    • 17% Below List Price
    • $309/SF
    • 88 Days On Market

    Current Estimated Value $569,786

    Last Listing Agent Megan Cross FANNIE HILLMAN & ASSOCIATES

    1267 Michigan Ave, Winter Park, FL 32789
  • 700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789
    700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789
    /2

    $330,000 Sold Jul 23, 2025

    700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,074 Sq Ft
    • Built 1964

    Last Sold Summary

    • 16% Below List Price
    • $307/SF
    • 303 Days On Market

    Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789
  • 2819 Scarlet Rd, Winter Park, FL 32792
    2819 Scarlet Rd, Winter Park, FL 32792
    /2

    $515,000 Sold Jun 26, 2025

    2819 Scarlet Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,197 Sq Ft
    • Built 1963

    Last Sold Summary

    • $234/SF
    • 58 Days On Market

    Current Estimated Value $521,384

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    2819 Scarlet Rd, Winter Park, FL 32792
  • 940 Lincoln Cir, Winter Park, FL 32789
    940 Lincoln Cir, Winter Park, FL 32789
    /2

    $2,495,000 Sold Jul 22, 2025

    940 Lincoln Cir, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,551 Sq Ft
    • Built 1995

    Last Sold Summary

    • 26% Below List Price
    • $703/SF
    • 47 Days On Market

    Current Estimated Value $2,514,447

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    940 Lincoln Cir, Winter Park, FL 32789
  • 764 W Comstock Ave, Winter Park, FL 32789
    764 W Comstock Ave, Winter Park, FL 32789
    /2

    $450,000 Sold Mar 31, 2026

    764 W Comstock Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 925 Sq Ft
    • Built 1935

    Last Sold Summary

    • 5% Below List Price
    • $486/SF
    • 17 Days On Market

    Current Estimated Value $465,382

    Last Listing Agent Manny del Valle KELLER WILLIAMS WINTER PARK

    764 W Comstock Ave, Winter Park, FL 32789
  • 3011 Temple Trail, Winter Park, FL 32789
    3011 Temple Trail, Winter Park, FL 32789
    /2

    $900,000 Sold Aug 29, 2025

    3011 Temple Trail, Winter Park, FL 32789

    • 5 Beds
    • 2.5 Baths
    • 2,406 Sq Ft
    • Built 1965

    Last Sold Summary

    • 10% Below List Price
    • $374/SF
    • 83 Days On Market

    Current Estimated Value $889,383

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    3011 Temple Trail, Winter Park, FL 32789
  • 702 Via Bella, Winter Park, FL 32789
    702 Via Bella, Winter Park, FL 32789
    /2

    $4,150,000 Sold Feb 18, 2026

    702 Via Bella, Winter Park, FL 32789

    • 4 Beds
    • 5.5 Baths
    • 3,720 Sq Ft
    • Built 2025

    Last Sold Summary

    • 11% Below List Price
    • $1,116/SF
    • 149 Days On Market

    Current Estimated Value $3,834,802

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

    702 Via Bella, Winter Park, FL 32789
  • 1309 Paradise Ln, Winter Park, FL 32792
    1309 Paradise Ln, Winter Park, FL 32792
    /2

    $360,000 Sold Oct 09, 2025

    1309 Paradise Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,606 Sq Ft
    • Built 1984

    Last Sold Summary

    • 15% Below List Price
    • $224/SF
    • 242 Days On Market

    Current Estimated Value $374,988

    Last Listing Agent Barbara Mills COLDWELL BANKER REALTY

    1309 Paradise Ln, Winter Park, FL 32792
  • 1250 S Denning Dr Unit 104, Winter Park, FL 32789
    1250 S Denning Dr Unit 104, Winter Park, FL 32789
    /2

    $190,000 Sold Mar 20, 2026

    1250 S Denning Dr Unit 104, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 908 Sq Ft
    • Built 1967

    Last Sold Summary

    • 17% Below List Price
    • $209/SF
    • 60 Days On Market

    Current Estimated Value $213,088

    Last Listing Agent John Harbuck SERHANT

    1250 S Denning Dr Unit 104, Winter Park, FL 32789
  • 255 Sandlewood Trail, Winter Park, FL 32789
    255 Sandlewood Trail, Winter Park, FL 32789
    /2

    $243,800 Sold May 30, 2025

    255 Sandlewood Trail, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 960 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Below List Price
    • $254/SF
    • 24 Days On Market

    Last Listing Agent Freddie Crespo INVESTOR'S REAL ESTATE LLC

    255 Sandlewood Trail, Winter Park, FL 32789
  • 958 Dupont Ave, Winter Park, FL 32789
    958 Dupont Ave, Winter Park, FL 32789
    /2

    $368,500 Sold Apr 03, 2026

    958 Dupont Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft
    • Built 1956

    Last Sold Summary

    • 3% Below List Price
    • $234/SF
    • 49 Days On Market

    Current Estimated Value $371,999

    Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

    958 Dupont Ave, Winter Park, FL 32789
  • 3028 George Mason Ave Unit 7, Winter Park, FL 32792
    3028 George Mason Ave Unit 7, Winter Park, FL 32792
    /2

    $60,000 Sold Feb 19, 2026

    3028 George Mason Ave Unit 7, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,088 Sq Ft
    • Built 1974

    Last Sold Summary

    • 50% Above List Price
    • $55/SF
    • 87 Days On Market

    Last Listing Agent David Rollins FLORIDA REALTY INVESTMENTS

    3028 George Mason Ave Unit 7, Winter Park, FL 32792
  • 1016 Howell Branch Rd, Winter Park, FL 32789
    1016 Howell Branch Rd, Winter Park, FL 32789
    /2

    $1,650,000 Sold May 01, 2026

    1016 Howell Branch Rd, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Below List Price
    • $525/SF
    • 7 Days On Market

    Current Estimated Value $1,668,056

    Last Listing Agent Andrew Birr PLAID PROPERTIES, LLC

    1016 Howell Branch Rd, Winter Park, FL 32789
  • 200 Saint Andrews Blvd Unit 1707, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 1707, Winter Park, FL 32792
    /2

    $205,000 Sold Dec 09, 2025

    200 Saint Andrews Blvd Unit 1707, Winter Park, FL 32792

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

    Last Sold Summary

    • 5% Below List Price
    • $168/SF
    • 14 Days On Market

    Current Estimated Value $208,230

    Last Listing Agent Tiffany Yates COMPASS FLORIDA LLC

    200 Saint Andrews Blvd Unit 1707, Winter Park, FL 32792
  • 1314 Canterbury Rd, Winter Park, FL 32789
    1314 Canterbury Rd, Winter Park, FL 32789
    /2

    $810,000 Sold Nov 26, 2025

    1314 Canterbury Rd, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,738 Sq Ft
    • Built 1950

    Last Sold Summary

    • $466/SF

    Current Estimated Value $793,367

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

    1314 Canterbury Rd, Winter Park, FL 32789
  • 5047 Ferncrest Dr, Winter Park, FL 32792
    5047 Ferncrest Dr, Winter Park, FL 32792
    /2

    $325,000 Sold Mar 06, 2026

    5047 Ferncrest Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,242 Sq Ft
    • Built 1969

    Last Sold Summary

    • 7% Below List Price
    • $262/SF
    • 67 Days On Market

    Current Estimated Value $344,827

    Last Listing Agent Wanda Perkins GLOBAL PROPERTIES SALES & MGMT

    5047 Ferncrest Dr, Winter Park, FL 32792
  • 131 Stefanik Rd, Winter Park, FL 32792
    131 Stefanik Rd, Winter Park, FL 32792
    /2

    $485,000 Sold Feb 03, 2026

    131 Stefanik Rd, Winter Park, FL 32792

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • Built 1980

    Last Sold Summary

    • 4% Above List Price
    • $242/SF
    • 154 Days On Market

    Last Listing Agent Thomas McNamara EXP REALTY LLC

    131 Stefanik Rd, Winter Park, FL 32792
  • 7446 Houston Ct E, Winter Park, FL 32792
    7446 Houston Ct E, Winter Park, FL 32792
    /2

    $449,999 Sold Aug 22, 2025

    7446 Houston Ct E, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,795 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Below List Price
    • $251/SF
    • 56 Days On Market

    Current Estimated Value $442,970

    Last Listing Agent Walter Taylor KELLER WILLIAMS REALTY AT THE PARKS

    7446 Houston Ct E, Winter Park, FL 32792
  • 1157 Valley Creek Run, Winter Park, FL 32792
    1157 Valley Creek Run, Winter Park, FL 32792
    /2

    $455,000 Sold Oct 03, 2025

    1157 Valley Creek Run, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,171 Sq Ft
    • Built 1995

    Last Sold Summary

    • 16% Below List Price
    • $210/SF
    • 133 Days On Market

    Current Estimated Value $474,942

    Last Listing Agent Roberta Shoopman CHARLES RUTENBERG REALTY ORLANDO

    1157 Valley Creek Run, Winter Park, FL 32792
  • 1050 Reading Ct, Winter Park, FL 32792
    1050 Reading Ct, Winter Park, FL 32792
    /2

    $349,000 Sold Aug 29, 2025

    1050 Reading Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,637 Sq Ft
    • Built 1983

    Last Sold Summary

    • 8% Below List Price
    • $213/SF
    • 52 Days On Market

    Current Estimated Value $366,321

    Last Listing Agent Carmen Vazquez REALTY TECH INC

    1050 Reading Ct, Winter Park, FL 32792
  • 1690 Palm Ave, Winter Park, FL 32789
    1690 Palm Ave, Winter Park, FL 32789
    /2

    $2,495,000 Sold Jul 21, 2025

    1690 Palm Ave, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 3,967 Sq Ft
    • Built 2020

    Last Sold Summary

    • 12% Below List Price
    • $629/SF
    • 56 Days On Market

    Current Estimated Value $2,501,337

    Last Listing Agent Daniel Robinson HOUWZER INC

    1690 Palm Ave, Winter Park, FL 32789
  • 4887 Seminole Ave, Winter Park, FL 32792
    4887 Seminole Ave, Winter Park, FL 32792
    4887 Seminole Ave, Winter Park, FL 32792
    /52

    $480,000 Sold Jun 05, 2025

    4887 Seminole Ave, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,256 Sq Ft
    • Built 1954

    Last Sold Summary

    • 4% Below List Price
    • $213/SF
    • 28 Days On Market

    Current Estimated Value $484,491

    Last Listing Agent Timothy Oster CHARLES RUTENBERG REALTY ORLANDO

    4887 Seminole Ave, Winter Park, FL 32792
  • 1690 Oneco Ave, Winter Park, FL 32789
    1690 Oneco Ave, Winter Park, FL 32789
    /2

    $1,075,000 Sold Jul 31, 2025

    1690 Oneco Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,703 Sq Ft
    • Built 1967

    Last Sold Summary

    • 10% Below List Price
    • $398/SF
    • 140 Days On Market

    Current Estimated Value $1,114,234

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

    1690 Oneco Ave, Winter Park, FL 32789

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