1,127

Recently Sold Winter Park, FL Homes

Section Image
  • 631 Symonds Ave, Winter Park, FL 32789
    631 Symonds Ave, Winter Park, FL 32789
    /2

    $475,000 Sold Oct 14, 2025

    631 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

    Current Estimated Value $472,210

    Last Listing Agent Emily Williams FANNIE HILLMAN & ASSOCIATES

    631 Symonds Ave, Winter Park, FL 32789
  • 1268 Preserve Point Dr, Winter Park, FL 32789
    1268 Preserve Point Dr, Winter Park, FL 32789
    /2

    $2,325,000 Sold Nov 10, 2025

    1268 Preserve Point Dr, Winter Park, FL 32789

    • 4 Beds
    • 4 Baths
    • 4,315 Sq Ft
    • Built 2006

    Last Sold Summary

    • 1% Below List Price
    • $539/SF
    • 2 Days On Market

    Current Estimated Value $2,303,080

    Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

    1268 Preserve Point Dr, Winter Park, FL 32789
  • 185 Scottsdale Square Unit F185, Winter Park, FL 32792
    185 Scottsdale Square Unit F185, Winter Park, FL 32792
    /2

    $82,000 Sold Jun 20, 2025

    185 Scottsdale Square Unit F185, Winter Park, FL 32792

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

    Last Sold Summary

    • 25% Below List Price
    • $80/SF
    • 13 Days On Market

    Current Estimated Value $78,285

    Last Listing Agent Erin Baker FANNIE HILLMAN & ASSOCIATES

    185 Scottsdale Square Unit F185, Winter Park, FL 32792
  • 7266 Swallow Run, Winter Park, FL 32792
    7266 Swallow Run, Winter Park, FL 32792
    /2

    $155,000 Sold Jun 30, 2025

    7266 Swallow Run, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 756 Sq Ft
    • Built 1985

    Last Sold Summary

    • 15% Below List Price
    • $205/SF
    • 107 Days On Market

    Current Estimated Value $148,689

    Last Listing Agent Jessica Riccardo TRINITY REAL ESTATE SALES LLC

    7266 Swallow Run, Winter Park, FL 32792
  • 1640 Cypress Point Ln, Winter Park, FL 32792
    1640 Cypress Point Ln, Winter Park, FL 32792
    /2

    $655,000 Sold Sep 12, 2025

    1640 Cypress Point Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft
    • Built 1980

    Last Sold Summary

    • 8% Below List Price
    • $384/SF
    • 23 Days On Market

    Current Estimated Value $644,596

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    1640 Cypress Point Ln, Winter Park, FL 32792
  • 2002 Karolina Ave, Winter Park, FL 32789
    2002 Karolina Ave, Winter Park, FL 32789
    /2

    $700,000 Sold Feb 26, 2026

    2002 Karolina Ave, Winter Park, FL 32789

    • Land
    • 0.45 Acre
    • $1,555,556 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 68 Days On Market

    Current Estimated Value $721,960

    Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    2002 Karolina Ave, Winter Park, FL 32789
  • 3520 Balsam Dr, Winter Park, FL 32792
    3520 Balsam Dr, Winter Park, FL 32792
    /2

    $428,000 Sold Jul 02, 2025

    3520 Balsam Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,468 Sq Ft
    • Built 1965

    Last Sold Summary

    • 1% Above List Price
    • $292/SF
    • 22 Days On Market

    Current Estimated Value $415,553

    Last Listing Agent Cece Wong EXP REALTY LLC

    3520 Balsam Dr, Winter Park, FL 32792
  • 1807 Yorkshire Dr, Winter Park, FL 32792
    1807 Yorkshire Dr, Winter Park, FL 32792
    /2

    $450,000 Sold May 29, 2025

    1807 Yorkshire Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,672 Sq Ft
    • Built 1956

    Last Sold Summary

    • 13% Below List Price
    • $269/SF
    • 26 Days On Market

    Current Estimated Value $1,237,139

    Last Listing Agent Carla Stanton MAINFRAME REAL ESTATE

    1807 Yorkshire Dr, Winter Park, FL 32792
  • 3132 Nicholson Dr, Winter Park, FL 32792
    3132 Nicholson Dr, Winter Park, FL 32792
    /2

    $447,500 Sold Apr 30, 2025

    3132 Nicholson Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,537 Sq Ft
    • Built 1977

    Last Sold Summary

    • 3% Below List Price
    • $291/SF
    • 14 Days On Market

    Current Estimated Value $437,655

    Last Listing Agent Vince Indiveri LIVE FLORIDA NOW LLC

    3132 Nicholson Dr, Winter Park, FL 32792
  • 2739 Amsden Rd, Winter Park, FL 32792
    2739 Amsden Rd, Winter Park, FL 32792
    /2

    $510,000 Sold Aug 29, 2025

    2739 Amsden Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,877 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Above List Price
    • $272/SF
    • 6 Days On Market

    Current Estimated Value $499,528

    Last Listing Agent D'Anne Mica ARROWSMITH REALTY, INC

    2739 Amsden Rd, Winter Park, FL 32792
  • 4026 Tenita Dr, Winter Park, FL 32792
    4026 Tenita Dr, Winter Park, FL 32792
    /2

    $470,000 Sold Aug 18, 2025

    4026 Tenita Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,122 Sq Ft
    • Built 1979

    Last Sold Summary

    • 16% Below List Price
    • $221/SF
    • 226 Days On Market

    Current Estimated Value $473,630

    Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

    4026 Tenita Dr, Winter Park, FL 32792
  • 2712 Cady Way Unit 4, Winter Park, FL 32792
    2712 Cady Way Unit 4, Winter Park, FL 32792
    /2

    $615,000 Sold Jun 02, 2025

    2712 Cady Way Unit 4, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,197 Sq Ft
    • Built 1964

    Last Sold Summary

    • 2% Below List Price
    • $280/SF
    • 5 Days On Market

    Current Estimated Value $631,737

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    2712 Cady Way Unit 4, Winter Park, FL 32792
  • 3021 Little Cypress Cove, Winter Park, FL 32792
    3021 Little Cypress Cove, Winter Park, FL 32792
    /2

    $400,000 Sold May 14, 2025

    3021 Little Cypress Cove, Winter Park, FL 32792

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

    Last Sold Summary

    • 6% Below List Price
    • $239/SF
    • 18 Days On Market

    Current Estimated Value $398,203

    Last Listing Agent Christy Lombard LPT REALTY LLC

    3021 Little Cypress Cove, Winter Park, FL 32792
  • 2825 Mulford Ave, Winter Park, FL 32789
    2825 Mulford Ave, Winter Park, FL 32789
    /2

    $655,000 Sold Dec 03, 2025

    2825 Mulford Ave, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,249 Sq Ft
    • Built 1952

    Last Sold Summary

    • 6% Below List Price
    • $524/SF
    • 50 Days On Market

    Current Estimated Value $645,966

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

    2825 Mulford Ave, Winter Park, FL 32789
  • 2358 Sun Valley Cir, Winter Park, FL 32792
    2358 Sun Valley Cir, Winter Park, FL 32792
    /2

    $272,500 Sold Aug 26, 2025

    2358 Sun Valley Cir, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,295 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $210/SF
    • 24 Days On Market

    Current Estimated Value $250,452

    Last Listing Agent Natalie Kauffman KELLER WILLIAMS CLASSIC

    2358 Sun Valley Cir, Winter Park, FL 32792
  • 835 Antonette Ave, Winter Park, FL 32789
    835 Antonette Ave, Winter Park, FL 32789
    /2

    $1,175,000 Sold Jul 08, 2025

    835 Antonette Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,867 Sq Ft
    • Built 1925

    Last Sold Summary

    • 2% Below List Price
    • $629/SF
    • 7 Days On Market

    Current Estimated Value $1,186,917

    Last Listing Agent Alexis Davis FANNIE HILLMAN & ASSOCIATES

    835 Antonette Ave, Winter Park, FL 32789
  • 600 W Webster Ave, Winter Park, FL 32789
    600 W Webster Ave, Winter Park, FL 32789
    /2

    $300,000 Sold Feb 20, 2026

    600 W Webster Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 754 Sq Ft
    • Built 1950

    Last Sold Summary

    • 2% Above List Price
    • $398/SF
    • 5 Days On Market

    Current Estimated Value $388,544

    Last Listing Agent Nicholas Cadwallader REALTY ONE GROUP MVP

    600 W Webster Ave, Winter Park, FL 32789
  • 8041 Lake Waunatta Dr, Winter Park, FL 32792
    8041 Lake Waunatta Dr, Winter Park, FL 32792
    /2

    $1,422,750 Sold Oct 21, 2025

    8041 Lake Waunatta Dr, Winter Park, FL 32792

    • 5 Beds
    • 4.5 Baths
    • 5,329 Sq Ft
    • Built 1984

    Last Sold Summary

    • 16% Below List Price
    • $267/SF
    • 170 Days On Market

    Current Estimated Value $1,416,608

    Last Listing Agent Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

    8041 Lake Waunatta Dr, Winter Park, FL 32792
  • 2865 Clever Ln, Winter Park, FL 32792
    2865 Clever Ln, Winter Park, FL 32792
    /2

    $430,000 Sold May 19, 2025

    2865 Clever Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft
    • Built 2023

    Last Sold Summary

    • 5% Below List Price
    • $225/SF
    • 140 Days On Market

    Current Estimated Value $425,996

    Last Listing Agent Denise Del Castillo LPT REALTY, LLC

    2865 Clever Ln, Winter Park, FL 32792
  • 2923 Cove Trail, Winter Park, FL 32789
    2923 Cove Trail, Winter Park, FL 32789
    /2

    $1,050,000 Sold Jul 07, 2025

    2923 Cove Trail, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,377 Sq Ft
    • Built 1964

    Last Sold Summary

    • 2% Above List Price
    • $311/SF
    • 9 Days On Market

    Current Estimated Value $1,088,889

    Last Listing Agent Robin Delaney KELLER WILLIAMS ADVANTAGE III

    2923 Cove Trail, Winter Park, FL 32789
  • 7895 Pleasant Pine Cir, Winter Park, FL 32792
    7895 Pleasant Pine Cir, Winter Park, FL 32792
    /2

    $719,000 Sold Nov 19, 2025

    7895 Pleasant Pine Cir, Winter Park, FL 32792

    • 5 Beds
    • 3.5 Baths
    • 3,568 Sq Ft
    • Built 2014

    Last Sold Summary

    • 2% Below List Price
    • $202/SF
    • 115 Days On Market

    Current Estimated Value $730,119

    Last Listing Agent Yvette Hoover ALL REAL ESTATE & INVESTMENTS

    7895 Pleasant Pine Cir, Winter Park, FL 32792
  • 1730 Oneco Ave, Winter Park, FL 32789
    1730 Oneco Ave, Winter Park, FL 32789
    /2

    $705,000 Sold Jul 21, 2025

    1730 Oneco Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1967

    Last Sold Summary

    • 8% Above List Price
    • $501/SF
    • 2 Days On Market

    Current Estimated Value $702,710

    Last Listing Agent John Tremblay THE TEAM REAL ESTATE GROUP INC

    1730 Oneco Ave, Winter Park, FL 32789
  • 1509 Sugarwood Cir, Winter Park, FL 32792
    1509 Sugarwood Cir, Winter Park, FL 32792
    /2

    $278,250 Sold Dec 15, 2025

    1509 Sugarwood Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,706 Sq Ft
    • Built 1983

    Last Sold Summary

    • 47% Above List Price
    • $163/SF
    • 38 Days On Market

    Current Estimated Value $327,667

    Last Listing Agent Heather Unger, PA ACME REAL ESTATE FLORIDA LLC

    1509 Sugarwood Cir, Winter Park, FL 32792
  • 441 N Capen Ave, Winter Park, FL 32789
    441 N Capen Ave, Winter Park, FL 32789
    /2

    $765,000 Sold Nov 21, 2025

    441 N Capen Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,745 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Below List Price
    • $438/SF
    • 183 Days On Market

    Current Estimated Value $771,879

    Last Listing Agent Susan Taliaferro COLDWELL BANKER REALTY

    441 N Capen Ave, Winter Park, FL 32789
  • 851 Georgia Ave, Winter Park, FL 32789
    851 Georgia Ave, Winter Park, FL 32789
    /2

    $3,600,000 Sold May 21, 2025

    851 Georgia Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 4,314 Sq Ft
    • Built 1935

    Last Sold Summary

    • 9% Below List Price
    • $834/SF
    • 24 Days On Market

    Current Estimated Value $3,705,874

    Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

    851 Georgia Ave, Winter Park, FL 32789
  • 3220 Netherwood Dr, Winter Park, FL 32792
    3220 Netherwood Dr, Winter Park, FL 32792
    /2

    $195,000 Sold Oct 17, 2025

    3220 Netherwood Dr, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft
    • Built 1982

    Last Sold Summary

    • 13% Below List Price
    • $188/SF
    • 87 Days On Market

    Current Estimated Value $275,122

    Last Listing Agent Nimrah Ashraf THE FIRM RE

    3220 Netherwood Dr, Winter Park, FL 32792
  • 1448 E Brookshire Ct, Winter Park, FL 32792
    1448 E Brookshire Ct, Winter Park, FL 32792
    /2

    $370,000 Sold Mar 24, 2026

    1448 E Brookshire Ct, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,518 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Below List Price
    • $244/SF
    • 28 Days On Market

    Current Estimated Value $378,507

    Last Listing Agent Antoine Divay FCG REALTY

    1448 E Brookshire Ct, Winter Park, FL 32792
  • 1155 Woodmere Dr, Winter Park, FL 32789
    1155 Woodmere Dr, Winter Park, FL 32789
    /2

    $5,250,000 Sold Oct 06, 2025

    1155 Woodmere Dr, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 5,051 Sq Ft
    • Built 2003

    Last Sold Summary

    • 1% Below List Price
    • $1,039/SF
    • 0 Days On Market

    Current Estimated Value $5,037,558

    Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

    1155 Woodmere Dr, Winter Park, FL 32789
  • 200 St Andrews Blvd Unit 802, Winter Park, FL 32792
    200 St Andrews Blvd Unit 802, Winter Park, FL 32792
    /2

    $185,000 Sold Aug 05, 2025

    200 St Andrews Blvd Unit 802, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 987 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Below List Price
    • $187/SF
    • 7 Days On Market

    Current Estimated Value $184,490

    Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

    200 St Andrews Blvd Unit 802, Winter Park, FL 32792
  • 2739 Riddle Dr, Winter Park, FL 32789
    2739 Riddle Dr, Winter Park, FL 32789
    /2

    $640,000 Sold May 02, 2025

    2739 Riddle Dr, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 1,881 Sq Ft
    • Built 2023

    Last Sold Summary

    • 4% Below List Price
    • $340/SF
    • 19 Days On Market

    Current Estimated Value $662,739

    Last Listing Agent JASON OLD COLDWELL BANKER REALTY

    2739 Riddle Dr, Winter Park, FL 32789
  • 2536 Brookshire Ave, Winter Park, FL 32792
    2536 Brookshire Ave, Winter Park, FL 32792
    /2

    $1,275,000 Sold Jul 08, 2025

    2536 Brookshire Ave, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,140 Sq Ft
    • Built 2018

    Last Sold Summary

    • 9% Below List Price
    • $406/SF
    • 83 Days On Market

    Current Estimated Value $1,238,913

    Last Listing Agent Richard Palmano PALMANO GROUP RE BROKERAGE LLC

    2536 Brookshire Ave, Winter Park, FL 32792
  • 101 S Ranger Blvd, Winter Park, FL 32792
    101 S Ranger Blvd, Winter Park, FL 32792
    /2

    $515,000 Sold Oct 06, 2025

    101 S Ranger Blvd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1963

    Last Sold Summary

    • $322/SF
    • 2 Days On Market

    Current Estimated Value $501,880

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    101 S Ranger Blvd, Winter Park, FL 32792
  • 2042 Yorkshire Dr, Winter Park, FL 32792
    2042 Yorkshire Dr, Winter Park, FL 32792
    /2

    $475,000 Sold Feb 06, 2026

    2042 Yorkshire Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,573 Sq Ft
    • Built 1961

    Last Sold Summary

    • 5% Below List Price
    • $302/SF
    • 32 Days On Market

    Current Estimated Value $489,053

    Last Listing Agent Steven Ritz KELLER WILLIAMS WINTER PARK

    2042 Yorkshire Dr, Winter Park, FL 32792
  • 7888 Pleasant Pine Cir, Winter Park, FL 32792
    7888 Pleasant Pine Cir, Winter Park, FL 32792
    /2

    $625,000 Sold Nov 03, 2025

    7888 Pleasant Pine Cir, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,267 Sq Ft
    • Built 2016

    Last Sold Summary

    • $276/SF
    • 7 Days On Market

    Current Estimated Value $616,083

    Last Listing Agent Todd Schroth EXP REALTY LLC

    7888 Pleasant Pine Cir, Winter Park, FL 32792
  • 2489 Tahoe Cir Unit 2489, Winter Park, FL 32792
    2489 Tahoe Cir Unit 2489, Winter Park, FL 32792
    /2

    $260,000 Sold Jan 20, 2026

    2489 Tahoe Cir Unit 2489, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $198/SF
    • 87 Days On Market

    Current Estimated Value $262,369

    Last Listing Agent Kim James CHARLES RUTENBERG REALTY ORLANDO

    2489 Tahoe Cir Unit 2489, Winter Park, FL 32792
  • 2244 Brookshire Ave, Winter Park, FL 32792
    2244 Brookshire Ave, Winter Park, FL 32792
    /2

    $600,000 Sold Aug 05, 2025

    2244 Brookshire Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft
    • Built 1958

    Last Sold Summary

    • 9% Above List Price
    • $410/SF
    • 26 Days On Market

    Current Estimated Value $567,455

    Last Listing Agent Melissa Johnson EXP REALTY LLC

    2244 Brookshire Ave, Winter Park, FL 32792
  • 3106 Patel Dr, Winter Park, FL 32792
    3106 Patel Dr, Winter Park, FL 32792
    /2

    $230,000 Sold May 20, 2025

    3106 Patel Dr, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 916 Sq Ft
    • Built 1989

    Last Sold Summary

    • 4% Below List Price
    • $251/SF
    • 20 Days On Market

    Current Estimated Value $230,911

    Last Listing Agent Karen Jacobs CHARLES RUTENBERG REALTY ORLANDO

    3106 Patel Dr, Winter Park, FL 32792
  • 1015 Bungalow Ave, Winter Park, FL 32789
    1015 Bungalow Ave, Winter Park, FL 32789
    /2

    $630,000 Sold Oct 03, 2025

    1015 Bungalow Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • Built 2012

    Last Sold Summary

    • $377/SF
    • 2 Days On Market

    Current Estimated Value $632,184

    Last Listing Agent David Francetic COLDWELL BANKER REALTY

    1015 Bungalow Ave, Winter Park, FL 32789
  • 1219 Verdant Glade Place, Winter Park, FL 32792
    1219 Verdant Glade Place, Winter Park, FL 32792
    /2

    $650,000 Sold May 30, 2025

    1219 Verdant Glade Place, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 2,002 Sq Ft
    • Built 2019

    Last Sold Summary

    • 6% Below List Price
    • $325/SF
    • 79 Days On Market

    Current Estimated Value $639,743

    Last Listing Agent Maggie Walas FORTUNE INTERNATIONAL REALTY

    1219 Verdant Glade Place, Winter Park, FL 32792
  • 3383 Hamlet Loop, Winter Park, FL 32792
    3383 Hamlet Loop, Winter Park, FL 32792
    /2

    $389,000 Sold Dec 30, 2025

    3383 Hamlet Loop, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,201 Sq Ft
    • Built 1994

    Last Sold Summary

    • $324/SF
    • 10 Days On Market

    Current Estimated Value $381,245

    Last Listing Agent Jason Asa LPT REALTY, LLC

    3383 Hamlet Loop, Winter Park, FL 32792

Showing Results 561 - 600, Page 15 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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