1,095

Recently Sold Winter Park, FL Homes

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  • 2312 Poinciana Rd, Winter Park, FL 32792
    2312 Poinciana Rd, Winter Park, FL 32792
    /2

    $440,000 Sold Jul 10, 2025

    2312 Poinciana Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,806 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Below List Price
    • $244/SF
    • 6 Days On Market

    Current Estimated Value $448,330

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    2312 Poinciana Rd, Winter Park, FL 32792
  • 639 Friar Rd, Winter Park, FL 32792
    639 Friar Rd, Winter Park, FL 32792
    /2

    $795,000 Sold May 08, 2026

    639 Friar Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,950 Sq Ft
    • Built 1967

    Last Sold Summary

    • $408/SF
    • 17 Days On Market

    Current Estimated Value $465,387

    Last Listing Agent Dianne Moore FLORIDA REALTY INVESTMENTS

    639 Friar Rd, Winter Park, FL 32792
  • 1651 N Park Ave, Winter Park, FL 32789
    1651 N Park Ave, Winter Park, FL 32789
    /2

    $505,000 Sold Jan 05, 2026

    1651 N Park Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,263 Sq Ft
    • Built 1965

    Last Sold Summary

    • $400/SF
    • 0 Days On Market

    Current Estimated Value $518,836

    Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

    1651 N Park Ave, Winter Park, FL 32789
  • 1000 S Semoran Blvd Unit 608, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 608, Winter Park, FL 32792
    /2

    $119,000 Sold Dec 08, 2025

    1000 S Semoran Blvd Unit 608, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,049 Sq Ft
    • Built 1969

    Last Sold Summary

    • 30% Below List Price
    • $113/SF
    • 155 Days On Market

    Current Estimated Value $125,739

    Last Listing Agent Maria Peralta CHARLES RUTENBERG REALTY ORLANDO

    1000 S Semoran Blvd Unit 608, Winter Park, FL 32792
  • 1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789
    1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789
    /2

    $750,000 Sold Jan 12, 2026

    1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,957 Sq Ft
    • Built 2007

    Last Sold Summary

    • 6% Below List Price
    • $383/SF
    • 84 Days On Market

    Current Estimated Value $761,159

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

    1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789
  • 2426 Windward Way, Winter Park, FL 32792
    2426 Windward Way, Winter Park, FL 32792
    /2

    $270,000 Sold Aug 28, 2025

    2426 Windward Way, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 932 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $290/SF
    • 50 Days On Market

    Current Estimated Value $268,209

    Last Listing Agent Kim Coburn RE/MAX TOWN & COUNTRY REALTY

    2426 Windward Way, Winter Park, FL 32792
  • 2809 Sanbina St, Winter Park, FL 32789
    2809 Sanbina St, Winter Park, FL 32789
    /2

    $420,000 Sold Jul 11, 2025

    2809 Sanbina St, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 1961

    Last Sold Summary

    • 2% Below List Price
    • $368/SF
    • 4 Days On Market

    Current Estimated Value $428,085

    Last Listing Agent Harry Kazarian STRONG FOUNDATION REALTY LLC

    2809 Sanbina St, Winter Park, FL 32789
  • 1695 Lee Rd Unit E211, Winter Park, FL 32789
    1695 Lee Rd Unit E211, Winter Park, FL 32789
    /2

    $110,000 Sold Apr 15, 2026

    1695 Lee Rd Unit E211, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Built 1966

    Last Sold Summary

    • 24% Below List Price
    • $125/SF
    • 117 Days On Market

    Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1

    1695 Lee Rd Unit E211, Winter Park, FL 32789
  • 1545 Indiana Ave Unit B, Winter Park, FL 32789
    1545 Indiana Ave Unit B, Winter Park, FL 32789
    /2

    $480,000 Sold Jul 28, 2025

    1545 Indiana Ave Unit B, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,598 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $300/SF
    • 3 Days On Market

    Current Estimated Value $473,631

    Last Listing Agent Ron Murray MAGIC REALTY LLC

    1545 Indiana Ave Unit B, Winter Park, FL 32789
  • 1911 Stonehurst Rd, Winter Park, FL 32789
    1911 Stonehurst Rd, Winter Park, FL 32789
    /2

    $2,910,000 Sold Jul 21, 2025

    1911 Stonehurst Rd, Winter Park, FL 32789

    • 4 Beds
    • 6 Baths
    • 5,097 Sq Ft
    • Built 2001

    Last Sold Summary

    • 14% Below List Price
    • $571/SF
    • 82 Days On Market

    Current Estimated Value $2,848,918

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1911 Stonehurst Rd, Winter Park, FL 32789
  • 513 Dunraven Dr, Winter Park, FL 32792
    513 Dunraven Dr, Winter Park, FL 32792
    /2

    $370,000 Sold Oct 20, 2025

    513 Dunraven Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft
    • Built 1956

    Last Sold Summary

    • $254/SF

    Current Estimated Value $455,697

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

    513 Dunraven Dr, Winter Park, FL 32792
  • 1809 Pineview Cir, Winter Park, FL 32792
    1809 Pineview Cir, Winter Park, FL 32792
    /2

    $465,000 Sold Sep 29, 2025

    1809 Pineview Cir, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,631 Sq Ft
    • Built 1956

    Last Sold Summary

    • 15% Below List Price
    • $285/SF
    • 106 Days On Market

    Current Estimated Value $454,400

    Last Listing Agent Eric Trumble II CHARLES RUTENBERG REALTY ORLANDO

    1809 Pineview Cir, Winter Park, FL 32792
  • 1585 Chestnut Ave, Winter Park, FL 32789
    1585 Chestnut Ave, Winter Park, FL 32789
    /2

    $987,500 Sold Jun 10, 2025

    1585 Chestnut Ave, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • Built 1959

    Last Sold Summary

    • 21% Below List Price
    • $445/SF
    • 101 Days On Market

    Current Estimated Value $998,015

    Last Listing Agent Ashley Landers KELLER WILLIAMS WINTER PARK

    1585 Chestnut Ave, Winter Park, FL 32789
  • 151 N Orlando Ave Unit 131, Winter Park, FL 32789
    151 N Orlando Ave Unit 131, Winter Park, FL 32789
    /2

    $385,000 Sold Jul 12, 2025

    151 N Orlando Ave Unit 131, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Below List Price
    • $385/SF
    • 355 Days On Market

    Current Estimated Value $367,260

    Last Listing Agent Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

    151 N Orlando Ave Unit 131, Winter Park, FL 32789
  • 7249 Abbey Ln, Winter Park, FL 32792
    7249 Abbey Ln, Winter Park, FL 32792
    /2

    $425,000 Sold Jul 07, 2025

    7249 Abbey Ln, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,508 Sq Ft
    • Built 1983

    Last Sold Summary

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

    Current Estimated Value $431,083

    Last Listing Agent Jackie Criswell RE/MAX TOWN & COUNTRY REALTY

    7249 Abbey Ln, Winter Park, FL 32792
  • 1610 Oakhurst Ave, Winter Park, FL 32789
    1610 Oakhurst Ave, Winter Park, FL 32789
    /2

    $3,200,000 Sold Oct 20, 2025

    1610 Oakhurst Ave, Winter Park, FL 32789

    • 5 Beds
    • 7 Baths
    • 4,255 Sq Ft
    • Built 2021

    Last Sold Summary

    • 2% Below List Price
    • $752/SF
    • 3 Days On Market

    Current Estimated Value $3,098,532

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

    1610 Oakhurst Ave, Winter Park, FL 32789
  • 1791 Spruce Ave, Winter Park, FL 32789
    1791 Spruce Ave, Winter Park, FL 32789
    /2

    $849,900 Sold Jun 10, 2025

    1791 Spruce Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,776 Sq Ft
    • Built 1956

    Last Sold Summary

    • $479/SF
    • 8 Days On Market

    Current Estimated Value $872,188

    Last Listing Agent Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

    1791 Spruce Ave, Winter Park, FL 32789
  • 3103 Ash Park Loop, Winter Park, FL 32792
    3103 Ash Park Loop, Winter Park, FL 32792
    /2

    $335,000 Sold Sep 17, 2025

    3103 Ash Park Loop, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Below List Price
    • $238/SF
    • 20 Days On Market

    Current Estimated Value $342,028

    Last Listing Agent Pam Hagood Ryan PREMIER SOTHEBY'S INTL. REALTY

    3103 Ash Park Loop, Winter Park, FL 32792
  • 7468 Swallow Run Unit 38, Winter Park, FL 32792
    7468 Swallow Run Unit 38, Winter Park, FL 32792
    /2

    $215,000 Sold Jun 13, 2025

    7468 Swallow Run Unit 38, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,578 Sq Ft
    • Built 1974

    Last Sold Summary

    • 12% Below List Price
    • $136/SF
    • 52 Days On Market

    Current Estimated Value $222,048

    Last Listing Agent Chris Creegan CREEGAN GROUP

    7468 Swallow Run Unit 38, Winter Park, FL 32792
  • 2529 Windward Way, Winter Park, FL 32792
    2529 Windward Way, Winter Park, FL 32792
    /2

    $183,000 Sold Apr 03, 2026

    2529 Windward Way, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Built 1977

    Last Sold Summary

    • 12% Below List Price
    • $166/SF
    • 4 Days On Market

    Current Estimated Value $249,090

    Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

    2529 Windward Way, Winter Park, FL 32792
  • 132 Burks Cir, Winter Park, FL 32789
    132 Burks Cir, Winter Park, FL 32789
    /2

    $1,500,000 Sold Apr 15, 2026

    132 Burks Cir, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,022 Sq Ft
    • Built 1997

    Last Sold Summary

    • 10% Below List Price
    • $496/SF
    • 130 Days On Market

    Current Estimated Value $1,523,649

    Last Listing Agent Ivey Geisler KELLER WILLIAMS REALTY AT THE PARKS

    132 Burks Cir, Winter Park, FL 32789
  • 2105 Fosgate Dr, Winter Park, FL 32789
    2105 Fosgate Dr, Winter Park, FL 32789
    /2

    $1,186,200 Sold Oct 30, 2025

    2105 Fosgate Dr, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 3,068 Sq Ft
    • Built 1956

    Last Sold Summary

    • 18% Below List Price
    • $387/SF
    • 145 Days On Market

    Current Estimated Value $1,173,854

    Last Listing Agent Eileen Winfrey IAD FLORIDA LLC

    2105 Fosgate Dr, Winter Park, FL 32789
  • 1460 Via Sangro Place, Winter Park, FL 32792
    1460 Via Sangro Place, Winter Park, FL 32792
    /2

    $1,500,000 Sold Dec 23, 2025

    1460 Via Sangro Place, Winter Park, FL 32792

    • 7 Beds
    • 4 Baths
    • 5,111 Sq Ft
    • Built 2015

    Last Sold Summary

    • 6% Below List Price
    • $293/SF
    • 18 Days On Market

    Current Estimated Value $1,483,330

    Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

    1460 Via Sangro Place, Winter Park, FL 32792
  • 151 N Orlando Ave Unit 204, Winter Park, FL 32789
    151 N Orlando Ave Unit 204, Winter Park, FL 32789
    /2

    $234,000 Sold Feb 24, 2026

    151 N Orlando Ave Unit 204, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 710 Sq Ft
    • Built 1960

    Last Sold Summary

    • 6% Below List Price
    • $330/SF
    • 244 Days On Market

    Current Estimated Value $231,843

    Last Listing Agent Eddie Cooper MAINFRAME REAL ESTATE

    151 N Orlando Ave Unit 204, Winter Park, FL 32789
  • 2804 Mulford Ave, Winter Park, FL 32789
    2804 Mulford Ave, Winter Park, FL 32789
    /2

    $510,000 Sold Jul 22, 2025

    2804 Mulford Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft
    • Built 1953

    Last Sold Summary

    • $335/SF

    Current Estimated Value $522,704

    Last Listing Agent Megan Lowe FANNIE HILLMAN & ASSOCIATES

    2804 Mulford Ave, Winter Park, FL 32789
  • 2573 Madeline Ave, Winter Park, FL 32789
    2573 Madeline Ave, Winter Park, FL 32789
    /2

    $850,000 Sold Dec 05, 2025

    2573 Madeline Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,035 Sq Ft
    • Built 2023

    Last Sold Summary

    • 5% Below List Price
    • $418/SF
    • 5 Days On Market

    Current Estimated Value $846,993

    Last Listing Agent Kristen Hamilton LOMBARDO TEAM REAL ESTATE LLC

    2573 Madeline Ave, Winter Park, FL 32789
  • 1871 Staunton Ave, Winter Park, FL 32789
    1871 Staunton Ave, Winter Park, FL 32789
    /2

    $425,000 Sold Aug 29, 2025

    1871 Staunton Ave, Winter Park, FL 32789

    • Land
    • 13,939 Sq Ft
    • $1,328,125 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 3 Days On Market

    Current Estimated Value $422,127

    Last Listing Agent Greg Staker WATSON REALTY CORP.

    1871 Staunton Ave, Winter Park, FL 32789
  • 1414 Bessmor Rd, Winter Park, FL 32789
    1414 Bessmor Rd, Winter Park, FL 32789
    /2

    $475,000 Sold Sep 19, 2025

    1414 Bessmor Rd, Winter Park, FL 32789

    • Land
    • 6,969 Sq Ft
    • $2,968,750 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 22 Days On Market

    Current Estimated Value $476,076

    Last Listing Agent Miranda Azer PARKVIEW REAL ESTATE

    1414 Bessmor Rd, Winter Park, FL 32789
  • 3214 Lowndes Dr, Winter Park, FL 32792
    3214 Lowndes Dr, Winter Park, FL 32792
    /2

    $395,000 Sold Dec 09, 2025

    3214 Lowndes Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1965

    Last Sold Summary

    • 1% Below List Price
    • $329/SF
    • 53 Days On Market

    Current Estimated Value $395,515

    Last Listing Agent Gregory Roberts LPT REALTY LLC

    3214 Lowndes Dr, Winter Park, FL 32792
  • 1362 Tierra Cir, Winter Park, FL 32792
    1362 Tierra Cir, Winter Park, FL 32792
    /2

    $395,000 Sold Feb 11, 2026

    1362 Tierra Cir, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,179 Sq Ft
    • Built 1969

    Last Sold Summary

    • 10% Below List Price
    • $181/SF
    • 107 Days On Market

    Current Estimated Value $400,995

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    1362 Tierra Cir, Winter Park, FL 32792
  • 3131 Ash Park Loop, Winter Park, FL 32792
    3131 Ash Park Loop, Winter Park, FL 32792
    /2

    $335,000 Sold Jun 26, 2025

    3131 Ash Park Loop, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • Built 1986

    Last Sold Summary

    • 16% Below List Price
    • $238/SF
    • 120 Days On Market

    Current Estimated Value $345,173

    Last Listing Agent Amanda Binns STRICKLAND REALTY GROUP INC

    3131 Ash Park Loop, Winter Park, FL 32792
  • 1840 Shiloh Ln, Winter Park, FL 32789
    1840 Shiloh Ln, Winter Park, FL 32789
    /2

    $1,025,000 Sold Jan 27, 2026

    1840 Shiloh Ln, Winter Park, FL 32789

    • Land
    • 11,761 Sq Ft
    • $3,796,296 per Acre

    Last Sold Summary

    • 2 Days On Market

    Last Listing Agent Gwyn Clark FANNIE HILLMAN & ASSOCIATES

    1840 Shiloh Ln, Winter Park, FL 32789
  • 640 Killarney Bay Ct Unit 4, Winter Park, FL 32789
    640 Killarney Bay Ct Unit 4, Winter Park, FL 32789
    /2

    $570,000 Sold Jan 02, 2026

    640 Killarney Bay Ct Unit 4, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 1,718 Sq Ft
    • Built 1986

    Last Sold Summary

    • 22% Below List Price
    • $332/SF
    • 231 Days On Market

    Current Estimated Value $531,925

    Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

    640 Killarney Bay Ct Unit 4, Winter Park, FL 32789
  • 786 Antonette Ave, Winter Park, FL 32789
    786 Antonette Ave, Winter Park, FL 32789
    /2

    $600,000 Sold Oct 31, 2025

    786 Antonette Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,146 Sq Ft
    • Built 1925

    Last Sold Summary

    • 25% Below List Price
    • $524/SF
    • 200 Days On Market

    Current Estimated Value $599,150

    Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

    786 Antonette Ave, Winter Park, FL 32789
  • 2828 Whispering Way, Winter Park, FL 32792
    2828 Whispering Way, Winter Park, FL 32792
    /2

    $379,000 Sold Oct 01, 2025

    2828 Whispering Way, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $289/SF
    • 99 Days On Market

    Current Estimated Value $371,947

    Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

    2828 Whispering Way, Winter Park, FL 32792
  • 1605 Puritan Ave, Winter Park, FL 32792
    1605 Puritan Ave, Winter Park, FL 32792
    /2

    $250,000 Sold Jan 16, 2026

    1605 Puritan Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,285 Sq Ft
    • Built 1963

    Last Sold Summary

    • 28% Below List Price
    • $195/SF
    • 26 Days On Market

    Current Estimated Value $292,598

    Last Listing Agent Denise San Miguel REALTY LYNK INC

    1605 Puritan Ave, Winter Park, FL 32792
  • 5202 Lake Howell Rd, Winter Park, FL 32792
    5202 Lake Howell Rd, Winter Park, FL 32792
    /2

    $349,000 Sold Mar 11, 2026

    5202 Lake Howell Rd, Winter Park, FL 32792

    • 3 Beds
    • 1.5 Baths
    • 1,112 Sq Ft
    • Built 1957

    Last Sold Summary

    • $314/SF
    • 5 Days On Market

    Current Estimated Value $346,260

    Last Listing Agent Crystal Vann CHARLES RUTENBERG REALTY ORLANDO

    5202 Lake Howell Rd, Winter Park, FL 32792
  • 2009 Nottingdale Ln, Winter Park, FL 32792
    2009 Nottingdale Ln, Winter Park, FL 32792
    /2

    $386,000 Sold Jul 09, 2025

    2009 Nottingdale Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,582 Sq Ft
    • Built 1980

    Last Sold Summary

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

    Current Estimated Value $399,243

    Last Listing Agent Wendy Calvet OLDE TOWN BROKERS INC

    2009 Nottingdale Ln, Winter Park, FL 32792
  • 1470 Place Picardy, Winter Park, FL 32789
    1470 Place Picardy, Winter Park, FL 32789
    /2

    $1,625,000 Sold Jun 12, 2025

    1470 Place Picardy, Winter Park, FL 32789

    • 5 Beds
    • 6 Baths
    • 4,227 Sq Ft
    • Built 2003

    Last Sold Summary

    • 17% Below List Price
    • $384/SF
    • 95 Days On Market

    Current Estimated Value $1,765,410

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

    1470 Place Picardy, Winter Park, FL 32789
  • 1151 Wildmeadow Run, Winter Park, FL 32792
    1151 Wildmeadow Run, Winter Park, FL 32792
    /2

    $750,000 Sold Jun 27, 2025

    1151 Wildmeadow Run, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,196 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Below List Price
    • $342/SF
    • 22 Days On Market

    Current Estimated Value $748,438

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

    1151 Wildmeadow Run, Winter Park, FL 32792

Showing Results 601 - 640, Page 16 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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