1,174

Recently Sold Winter Park, FL Homes

Section Image
  • 1034 Wildmeadow Run, Winter Park, FL 32792
    1034 Wildmeadow Run, Winter Park, FL 32792
    /2

    $830,000 Sold Jan 10, 2025

    1034 Wildmeadow Run, Winter Park, FL 32792

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

    Last Sold Summary

    • 2% Below List Price
    • $321/SF
    • 14 Days On Market

    Current Estimated Value $821,231

    Last Listing Agent Brian Hyser THE AGENCY ORLANDO

    1034 Wildmeadow Run, Winter Park, FL 32792
  • 3084 Heartleaf Place, Winter Park, FL 32792
    3084 Heartleaf Place, Winter Park, FL 32792
    /2

    $540,000 Sold Feb 28, 2025

    3084 Heartleaf Place, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,439 Sq Ft
    • Built 1997

    Last Sold Summary

    • 4% Below List Price
    • $221/SF
    • 6 Days On Market

    Current Estimated Value $545,405

    Last Listing Agent Susie Stewart RE/MAX SIGNATURE

    3084 Heartleaf Place, Winter Park, FL 32792
  • 3291 Oak Lake Place Unit 125, Winter Park, FL 32792
    3291 Oak Lake Place Unit 125, Winter Park, FL 32792
    /2

    $150,000 Sold May 07, 2025

    3291 Oak Lake Place Unit 125, Winter Park, FL 32792

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

    Last Sold Summary

    • 32% Below List Price
    • $145/SF
    • 251 Days On Market

    Current Estimated Value $158,315

    Last Listing Agent Greg Vazzana FANNIE HILLMAN & ASSOCIATES

    3291 Oak Lake Place Unit 125, Winter Park, FL 32792
  • 2250 Forrest Rd, Winter Park, FL 32789
    2250 Forrest Rd, Winter Park, FL 32789
    /2

    $1,050,000 Sold Aug 14, 2025

    2250 Forrest Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,492 Sq Ft
    • Built 1950

    Last Sold Summary

    • 12% Below List Price
    • $704/SF
    • 0 Days On Market

    Current Estimated Value $1,056,371

    Last Listing Agent Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

    2250 Forrest Rd, Winter Park, FL 32789
  • 1760 Mondrian Cir, Winter Park, FL 32789
    1760 Mondrian Cir, Winter Park, FL 32789
    /2

    $965,000 Sold Jul 07, 2025

    1760 Mondrian Cir, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,245 Sq Ft
    • Built 2024

    Last Sold Summary

    • 1% Below List Price
    • $430/SF
    • 11 Days On Market

    Current Estimated Value $948,753

    Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

    1760 Mondrian Cir, Winter Park, FL 32789
  • 1137 Oaks Blvd, Winter Park, FL 32789
    1137 Oaks Blvd, Winter Park, FL 32789
    /2

    $575,000 Sold Jan 24, 2025

    1137 Oaks Blvd, Winter Park, FL 32789

    • 2 Beds
    • 1.5 Baths
    • 1,149 Sq Ft
    • Built 1958

    Last Sold Summary

    • 5% Above List Price
    • $500/SF
    • 2 Days On Market

    Current Estimated Value $622,249

    Last Listing Agent Kelly Sue Stonebreaker RE/MAX TOWN & COUNTRY REALTY

    1137 Oaks Blvd, Winter Park, FL 32789
  • 2805 Bongart Rd, Winter Park, FL 32792
    2805 Bongart Rd, Winter Park, FL 32792
    /2

    $370,000 Sold Jun 01, 2025

    2805 Bongart Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,409 Sq Ft
    • Built 1958

    Last Sold Summary

    • 10% Below List Price
    • $263/SF
    • 12 Days On Market

    Current Estimated Value $373,511

    Last Listing Agent Jamie Stolinas Crame CENTURY 21 CARIOTI

    2805 Bongart Rd, Winter Park, FL 32792
  • 901 Palmer Ave, Winter Park, FL 32789
    901 Palmer Ave, Winter Park, FL 32789
    /2

    $975,000 Sold Nov 18, 2025

    901 Palmer Ave, Winter Park, FL 32789

    • Land
    • 0.32 Acre
    • $3,046,875 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 33 Days On Market

    Last Listing Agent Sharon Helsby FANNIE HILLMAN & ASSOCIATES

    901 Palmer Ave, Winter Park, FL 32789
  • 2320 High St, Winter Park, FL 32792
    2320 High St, Winter Park, FL 32792
    /2

    $365,000 Sold Nov 05, 2025

    2320 High St, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,071 Sq Ft
    • Built 1971

    Last Sold Summary

    • 9% Below List Price
    • $341/SF
    • 63 Days On Market

    Last Listing Agent Jessica Lee ONE LUXURY INTERNATIONAL LLC

    2320 High St, Winter Park, FL 32792
  • 1915 Stonehurst Rd, Winter Park, FL 32789
    1915 Stonehurst Rd, Winter Park, FL 32789
    /2

    $1,650,000 Sold Oct 09, 2025

    1915 Stonehurst Rd, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,489 Sq Ft
    • Built 1956

    Last Sold Summary

    • $663/SF
    • 0 Days On Market

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    1915 Stonehurst Rd, Winter Park, FL 32789
  • 311 E Morse Blvd Unit 6-7, Winter Park, FL 32789
    311 E Morse Blvd Unit 6-7, Winter Park, FL 32789
    /2

    $362,500 Sold Jul 30, 2025

    311 E Morse Blvd Unit 6-7, Winter Park, FL 32789

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

    Last Sold Summary

    • 19% Below List Price
    • $410/SF
    • 103 Days On Market

    Current Estimated Value $370,925

    Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    311 E Morse Blvd Unit 6-7, Winter Park, FL 32789
  • 7864 Pleasant Pine Cir, Winter Park, FL 32792
    7864 Pleasant Pine Cir, Winter Park, FL 32792
    /2

    $550,000 Sold Oct 23, 2025

    7864 Pleasant Pine Cir, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,182 Sq Ft
    • Built 2016

    Last Sold Summary

    • 2% Above List Price
    • $252/SF
    • 6 Days On Market

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    7864 Pleasant Pine Cir, Winter Park, FL 32792
  • 1819 Shadyhill Terrace, Winter Park, FL 32792
    1819 Shadyhill Terrace, Winter Park, FL 32792
    /2

    $513,000 Sold Aug 22, 2025

    1819 Shadyhill Terrace, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,811 Sq Ft
    • Built 1989

    Last Sold Summary

    • 4% Below List Price
    • $283/SF
    • 16 Days On Market

    Current Estimated Value $515,293

    Last Listing Agent Jonathan Ruiz KELLER WILLIAMS WINTER PARK

    1819 Shadyhill Terrace, Winter Park, FL 32792
  • 345 Sylvan Blvd, Winter Park, FL 32789
    345 Sylvan Blvd, Winter Park, FL 32789
    /2

    $995,000 Sold Jan 21, 2025

    345 Sylvan Blvd, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,011 Sq Ft
    • Built 1988

    Last Sold Summary

    • 13% Below List Price
    • $495/SF
    • 97 Days On Market

    Current Estimated Value $1,016,907

    Last Listing Agent Ben Laube EXP REALTY LLC

    345 Sylvan Blvd, Winter Park, FL 32789
  • 439 N Capen Ave, Winter Park, FL 32789
    439 N Capen Ave, Winter Park, FL 32789
    /2

    $800,000 Sold Feb 06, 2025

    439 N Capen Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,861 Sq Ft
    • Built 2017

    Last Sold Summary

    • 16% Below List Price
    • $430/SF
    • 105 Days On Market

    Current Estimated Value $808,546

    Last Listing Agent Justin Core EXP REALTY LLC

    439 N Capen Ave, Winter Park, FL 32789
  • 5334 Cypress Dr, Winter Park, FL 32792
    5334 Cypress Dr, Winter Park, FL 32792
    /2

    $420,000 Sold Jul 17, 2025

    5334 Cypress Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,734 Sq Ft
    • Built 1976

    Last Sold Summary

    • 1% Above List Price
    • $242/SF
    • 4 Days On Market

    Current Estimated Value $417,152

    Last Listing Agent Jeff Taulbee CHARLES RUTENBERG REALTY ORLANDO

    5334 Cypress Dr, Winter Park, FL 32792
  • 1932 Temple Dr, Winter Park, FL 32789
    1932 Temple Dr, Winter Park, FL 32789
    /2

    $1,100,000 Sold Apr 10, 2025

    1932 Temple Dr, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,432 Sq Ft
    • Built 1952

    Last Sold Summary

    • 15% Below List Price
    • $452/SF
    • 44 Days On Market

    Current Estimated Value $1,087,744

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

    1932 Temple Dr, Winter Park, FL 32789
  • 1778 Mondrian Cir, Winter Park, FL 32789
    1778 Mondrian Cir, Winter Park, FL 32789
    1778 Mondrian Cir, Winter Park, FL 32789
    /46

    $1,250,000 Sold Mar 14, 2025

    1778 Mondrian Cir, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,377 Sq Ft
    • Built 2023

    Last Sold Summary

    • $526/SF
    • 51 Days On Market

    Current Estimated Value $1,208,613

    Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

    1778 Mondrian Cir, Winter Park, FL 32789
  • 2812 Woodside Ave, Winter Park, FL 32789
    2812 Woodside Ave, Winter Park, FL 32789
    /2

    $600,000 Sold Oct 17, 2025

    2812 Woodside Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,842 Sq Ft
    • Built 1952

    Last Sold Summary

    • 4% Below List Price
    • $326/SF
    • 50 Days On Market

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    2812 Woodside Ave, Winter Park, FL 32789
  • 254 Sylvan Blvd, Winter Park, FL 32789
    254 Sylvan Blvd, Winter Park, FL 32789
    /2

    $2,594,550 Sold May 09, 2025

    254 Sylvan Blvd, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 3,653 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $710/SF
    • 8 Days On Market

    Current Estimated Value $2,510,883

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    254 Sylvan Blvd, Winter Park, FL 32789
  • 1405 Auburn Green Loop, Winter Park, FL 32792
    1405 Auburn Green Loop, Winter Park, FL 32792
    1405 Auburn Green Loop, Winter Park, FL 32792
    /59

    $300,000 Sold Dec 23, 2025

    1405 Auburn Green Loop, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,126 Sq Ft
    • Built 1984

    Last Sold Summary

    • 17% Below List Price
    • $266/SF
    • 170 Days On Market

    Last Listing Agent Geannina Mejia-Acevedo Charles Rutenberg Realty Orlan

    1405 Auburn Green Loop, Winter Park, FL 32792
  • 2680 Oglesby Ave, Winter Park, FL 32789
    2680 Oglesby Ave, Winter Park, FL 32789
    /2

    $1,025,000 Sold Jun 27, 2025

    2680 Oglesby Ave, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,546 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Below List Price
    • $403/SF
    • 55 Days On Market

    Current Estimated Value $1,011,445

    Last Listing Agent Kris Kennedy COMPASS FLORIDA LLC

    2680 Oglesby Ave, Winter Park, FL 32789
  • 5346 Cypress Dr, Winter Park, FL 32792
    5346 Cypress Dr, Winter Park, FL 32792
    /2

    $390,000 Sold Oct 27, 2025

    5346 Cypress Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • Built 1976

    Last Sold Summary

    • 7% Below List Price
    • $234/SF
    • 31 Days On Market

    Last Listing Agent Kristy Kesterson KELLER WILLIAMS ADVANTAGE REALTY

    5346 Cypress Dr, Winter Park, FL 32792
  • 178 Scottsdale Square Unit 178, Winter Park, FL 32792
    178 Scottsdale Square Unit 178, Winter Park, FL 32792
    /2

    $112,000 Sold Jan 06, 2025

    178 Scottsdale Square Unit 178, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft
    • Built 1974

    Last Sold Summary

    • 23% Below List Price
    • $110/SF
    • 339 Days On Market

    Current Estimated Value $104,793

    Last Listing Agent Esther Griller FLORIDA REALTY INVESTMENTS

    178 Scottsdale Square Unit 178, Winter Park, FL 32792
  • 8073 Pleasant Pine Cir, Winter Park, FL 32792
    8073 Pleasant Pine Cir, Winter Park, FL 32792
    /2

    $635,000 Sold Feb 21, 2025

    8073 Pleasant Pine Cir, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,319 Sq Ft
    • Built 2014

    Last Sold Summary

    • 1% Below List Price
    • $274/SF
    • 14 Days On Market

    Current Estimated Value $630,709

    Last Listing Agent Justin Adams EXP REALTY LLC

    8073 Pleasant Pine Cir, Winter Park, FL 32792
  • 3651 N Goldenrod Rd Unit 210, Winter Park, FL 32792
    3651 N Goldenrod Rd Unit 210, Winter Park, FL 32792
    /2

    $170,000 Sold Sep 04, 2025

    3651 N Goldenrod Rd Unit 210, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Built 1990

    Last Sold Summary

    • 15% Below List Price
    • $202/SF
    • 176 Days On Market

    Last Listing Agent Elenice Pereira WRA BUSINESS & REAL ESTATE

    3651 N Goldenrod Rd Unit 210, Winter Park, FL 32792
  • 210 Chelton Cir, Winter Park, FL 32789
    210 Chelton Cir, Winter Park, FL 32789
    /2

    $5,250,000 Sold Mar 31, 2025

    210 Chelton Cir, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 5,264 Sq Ft
    • Built 2024

    Last Sold Summary

    • 8% Below List Price
    • $997/SF
    • 125 Days On Market

    Current Estimated Value $1,309,179

    Last Listing Agent Laura Earl CORCORAN PREMIER REALTY

    210 Chelton Cir, Winter Park, FL 32789
  • 1010 N Pennsylvania Ave, Winter Park, FL 32789
    1010 N Pennsylvania Ave, Winter Park, FL 32789
    /2

    $2,400,000 Sold Mar 28, 2025

    1010 N Pennsylvania Ave, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 4,074 Sq Ft
    • Built 2017

    Last Sold Summary

    • 14% Below List Price
    • $589/SF
    • 94 Days On Market

    Current Estimated Value $2,391,923

    Last Listing Agent Dana Laing BHHS FLORIDA REALTY

    1010 N Pennsylvania Ave, Winter Park, FL 32789
  • 795 W Canton Ave, Winter Park, FL 32789
    795 W Canton Ave, Winter Park, FL 32789
    /2

    $1,050,000 Sold Jul 14, 2025

    795 W Canton Ave, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,374 Sq Ft
    • Built 2017

    Last Sold Summary

    • 9% Below List Price
    • $442/SF
    • 23 Days On Market

    Current Estimated Value $1,028,561

    Last Listing Agent Margo Rochelle WEICHERT REALTORS HALLMARK PROPERTIES

    795 W Canton Ave, Winter Park, FL 32789
  • 1612 Eastbrook Blvd, Winter Park, FL 32792
    1612 Eastbrook Blvd, Winter Park, FL 32792
    /2

    $360,000 Sold Aug 08, 2025

    1612 Eastbrook Blvd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,240 Sq Ft
    • Built 1961

    Last Sold Summary

    • 3% Below List Price
    • $290/SF
    • 104 Days On Market

    Current Estimated Value $357,708

    Last Listing Agent Justin Adams EXP REALTY LLC

    1612 Eastbrook Blvd, Winter Park, FL 32792
  • 1742 Barcelona Way, Winter Park, FL 32789
    1742 Barcelona Way, Winter Park, FL 32789
    /2

    $1,480,000 Sold Sep 19, 2025

    1742 Barcelona Way, Winter Park, FL 32789

    • 5 Beds
    • 8 Baths
    • 3,626 Sq Ft
    • Built 1973

    Last Sold Summary

    • 18% Below List Price
    • $408/SF
    • 81 Days On Market

    Current Estimated Value $1,500,180

    Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

    1742 Barcelona Way, Winter Park, FL 32789
  • 1541 Florentino Ln, Winter Park, FL 32792
    1541 Florentino Ln, Winter Park, FL 32792
    /2

    $350,000 Sold Jul 21, 2025

    1541 Florentino Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,682 Sq Ft
    • Built 2004

    Last Sold Summary

    • $208/SF
    • 70 Days On Market

    Current Estimated Value $351,522

    Last Listing Agent Jeffrey Friedman FANNIE HILLMAN & ASSOCIATES

    1541 Florentino Ln, Winter Park, FL 32792
  • 1741 Pine Ave, Winter Park, FL 32789
    1741 Pine Ave, Winter Park, FL 32789
    /2

    $1,500,000 Sold May 14, 2025

    1741 Pine Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 3,297 Sq Ft
    • Built 2002

    Last Sold Summary

    • $455/SF
    • 7 Days On Market

    Current Estimated Value $1,524,280

    Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

    1741 Pine Ave, Winter Park, FL 32789
  • 1339 Orchid Ave, Winter Park, FL 32789
    1339 Orchid Ave, Winter Park, FL 32789
    /2

    $560,000 Sold Aug 19, 2025

    1339 Orchid Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 789 Sq Ft
    • Built 1953

    Last Sold Summary

    • 12% Below List Price
    • $710/SF
    • 46 Days On Market

    Current Estimated Value $546,480

    Last Listing Agent Barbara Allen ABIDE REALTY

    1339 Orchid Ave, Winter Park, FL 32789
  • 4960 Tangerine Ave Unit 4960, Winter Park, FL 32792
    4960 Tangerine Ave Unit 4960, Winter Park, FL 32792
    /2

    $140,000 Sold Nov 17, 2025

    4960 Tangerine Ave Unit 4960, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 763 Sq Ft
    • Built 1973

    Last Sold Summary

    • 10% Below List Price
    • $183/SF
    • 72 Days On Market

    Last Listing Agent Stacy Chen KELLER WILLIAMS ADVANTAGE III

    4960 Tangerine Ave Unit 4960, Winter Park, FL 32792
  • 621 Symonds Ave, Winter Park, FL 32789
    621 Symonds Ave, Winter Park, FL 32789
    /2

    $475,000 Sold Oct 14, 2025

    621 Symonds Ave, Winter Park, FL 32789

    • Land
    • 0.13 Acre
    • $3,653,846 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 147 Days On Market

    Last Listing Agent Emily Williams FANNIE HILLMAN & ASSOCIATES

    621 Symonds Ave, Winter Park, FL 32789
  • 1827 Blaine Terrace, Winter Park, FL 32792
    1827 Blaine Terrace, Winter Park, FL 32792
    /2

    $250,000 Sold Jun 27, 2025

    1827 Blaine Terrace, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,114 Sq Ft
    • Built 1990

    Last Sold Summary

    • 11% Below List Price
    • $224/SF
    • 8 Days On Market

    Last Listing Agent Kerry Jeffcoat-Squeteri COMPASS FLORIDA LLC

    1827 Blaine Terrace, Winter Park, FL 32792
  • 2762 Hilda Cove, Winter Park, FL 32792
    2762 Hilda Cove, Winter Park, FL 32792
    /2

    $299,000 Sold Jun 17, 2025

    2762 Hilda Cove, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,493 Sq Ft
    • Built 1981

    Last Sold Summary

    • 15% Below List Price
    • $200/SF
    • 119 Days On Market

    Current Estimated Value $290,979

    Last Listing Agent Thomas Weclew THE REALTY MEDICS

    2762 Hilda Cove, Winter Park, FL 32792
  • 7336 Daniel Webster Dr Unit 9, Winter Park, FL 32792
    7336 Daniel Webster Dr Unit 9, Winter Park, FL 32792
    /2

    $115,000 Sold Jul 31, 2025

    7336 Daniel Webster Dr Unit 9, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,090 Sq Ft
    • Built 1974

    Last Sold Summary

    • 15% Below List Price
    • $106/SF
    • 89 Days On Market

    Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

    7336 Daniel Webster Dr Unit 9, Winter Park, FL 32792
  • 1500 Gay Rd Unit 10C, Winter Park, FL 32789
    1500 Gay Rd Unit 10C, Winter Park, FL 32789
    /2

    $230,000 Sold May 30, 2025

    1500 Gay Rd Unit 10C, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft
    • Built 1972

    Last Sold Summary

    • 7% Below List Price
    • $224/SF
    • 75 Days On Market

    Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 10C, Winter Park, FL 32789

Showing Results 321 - 360, Page 9 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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