313

Recently Sold Homes in 21550

Section Image
  • 648 S 3rd St, Oakland, MD 21550
    648 S 3rd St, Oakland, MD 21550
    648 S 3rd St, Oakland, MD 21550
    /61

    $275,000 Sold Sep 05, 2025

    648 S 3rd St, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1940

    Last Sold Summary

    • $185/SF
    • 3 Days On Market

    Current Estimated Value $270,333

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    648 S 3rd St, Oakland, MD 21550
  • 1746 Stockslager Rd, Oakland, MD 21550
    1746 Stockslager Rd, Oakland, MD 21550
    1746 Stockslager Rd, Oakland, MD 21550
    /131

    $2,250,000 Sold Mar 31, 2025

    1746 Stockslager Rd, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 4,713 Sq Ft
    • Built 1983

    Last Sold Summary

    • $477/SF
    • 131 Days On Market

    Current Estimated Value $2,131,761

    Last Listing Agent Jon Bell Railey Realty, Inc.

    1746 Stockslager Rd, Oakland, MD 21550
  • 1220 Broadford Rd, Oakland, MD 21550
    1220 Broadford Rd, Oakland, MD 21550
    1220 Broadford Rd, Oakland, MD 21550
    /52

    $365,000 Sold Aug 12, 2025

    1220 Broadford Rd, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 2,092 Sq Ft
    • Built 1971

    Last Sold Summary

    • $174/SF
    • 58 Days On Market

    Current Estimated Value $367,914

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    1220 Broadford Rd, Oakland, MD 21550
  • 425 Mountainview Dr, Oakland, MD 21550
    425 Mountainview Dr, Oakland, MD 21550
    425 Mountainview Dr, Oakland, MD 21550
    /50

    $739,000 Sold Oct 17, 2025

    425 Mountainview Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 1,586 Sq Ft
    • Built 1998

    Last Sold Summary

    • $466/SF
    • 32 Days On Market

    Current Estimated Value $752,167

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    425 Mountainview Dr, Oakland, MD 21550
  • 1073 George Washington Hwy, Oakland, MD 21550
    1073 George Washington Hwy, Oakland, MD 21550
    1073 George Washington Hwy, Oakland, MD 21550
    /89

    $365,000 Sold Feb 28, 2025

    1073 George Washington Hwy, Oakland, MD 21550

    • 5 Beds
    • 3 Baths
    • 2,910 Sq Ft
    • Built 1876

    Last Sold Summary

    • $125/SF

    Current Estimated Value $369,280

    Last Listing Agent Justin Liller Railey Realty, Inc.

    1073 George Washington Hwy, Oakland, MD 21550
  • Lot 32 Snowshoe Ct, Mc Henry, MD 21541
    Lot 32 Snowshoe Ct, Mc Henry, MD 21541
    Lot 32 Snowshoe Ct, Mc Henry, MD 21541
    /25

    $130,000 Sold Dec 30, 2025

    Lot 32 Snowshoe Ct, Mc Henry, MD 21541

    • Land
    • 0.4 Acre
    • $325,000 per Acre

    Last Sold Summary

    • 281 Days On Market

    Last Listing Agent Lana Roby The KW Collective

    Lot 32 Snowshoe Ct, Mc Henry, MD 21541
  • 3273 Lake Shore Dr, Oakland, MD 21550
    3273 Lake Shore Dr, Oakland, MD 21550
    3273 Lake Shore Dr, Oakland, MD 21550
    /80

    $1,270,000 Sold Oct 16, 2025

    3273 Lake Shore Dr, Oakland, MD 21550

    • 6 Beds
    • 3 Baths
    • 1,714 Sq Ft
    • Built 1930

    Last Sold Summary

    • $741/SF
    • 6 Days On Market

    Current Estimated Value $1,251,911

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    3273 Lake Shore Dr, Oakland, MD 21550
  • 1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    1931 Lake Shore Dr, Oakland, MD 21550
    /93

    $3,000,000 Sold Dec 02, 2025

    1931 Lake Shore Dr, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 5,100 Sq Ft
    • Built 2009

    Last Sold Summary

    • $588/SF
    • 430 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    1931 Lake Shore Dr, Oakland, MD 21550
  • 267 Woodlands Hill Ln, Oakland, MD 21550
    267 Woodlands Hill Ln, Oakland, MD 21550
    267 Woodlands Hill Ln, Oakland, MD 21550
    /72

    $975,000 Sold Sep 25, 2025

    267 Woodlands Hill Ln, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,232 Sq Ft
    • Built 2021

    Last Sold Summary

    • $437/SF
    • 136 Days On Market

    Current Estimated Value $999,285

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    267 Woodlands Hill Ln, Oakland, MD 21550
  • 1100 S Blakeslee Rd, Oakland, MD 21550
    1100 S Blakeslee Rd, Oakland, MD 21550
    1100 S Blakeslee Rd, Oakland, MD 21550
    /127

    $2,550,000 Sold Aug 01, 2025

    1100 S Blakeslee Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 6,572 Sq Ft
    • Built 1998

    Last Sold Summary

    • $388/SF
    • 0 Days On Market

    Current Estimated Value $2,588,147

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    1100 S Blakeslee Rd, Oakland, MD 21550
  • 29 Fern Loop, Sang Run, MD 21541
    29 Fern Loop, Sang Run, MD 21541
    29 Fern Loop, Sang Run, MD 21541
    /7

    $105,000 Sold Mar 17, 2025

    29 Fern Loop, Sang Run, MD 21541

    • Land
    • 1 Acre
    • $105,000 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Larry Smith Railey Realty, Inc.

    29 Fern Loop, Sang Run, MD 21541
  • 346 Skippers Point Rd, Oakland, MD 21550
    346 Skippers Point Rd, Oakland, MD 21550
    346 Skippers Point Rd, Oakland, MD 21550
    /73

    $530,000 Sold Oct 03, 2025

    346 Skippers Point Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1976

    Last Sold Summary

    • $294/SF
    • 50 Days On Market

    Current Estimated Value $549,723

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    346 Skippers Point Rd, Oakland, MD 21550
  • 735 Winston Rd, Oakland, MD 21550
    735 Winston Rd, Oakland, MD 21550
    735 Winston Rd, Oakland, MD 21550
    /53

    $1,300,000 Sold Apr 30, 2025

    735 Winston Rd, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 2,076 Sq Ft
    • Built 1985

    Last Sold Summary

    • $626/SF
    • 10 Days On Market

    Current Estimated Value $96,000

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    735 Winston Rd, Oakland, MD 21550
  • 18361 Garrett Hwy, Oakland, MD 21550
    18361 Garrett Hwy, Oakland, MD 21550
    18361 Garrett Hwy, Oakland, MD 21550
    /51

    $268,000 Sold Feb 27, 2025

    18361 Garrett Hwy, Oakland, MD 21550

    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft
    • Built 1977

    Last Sold Summary

    • $127/SF
    • 131 Days On Market

    Current Estimated Value $295,332

    Last Listing Agent Jon Bell Railey Realty, Inc.

    18361 Garrett Hwy, Oakland, MD 21550
  • 247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
    /82

    $554,999 Sold Oct 03, 2025

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550

    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft
    • Built 2007

    Last Sold Summary

    • $168/SF
    • 164 Days On Market

    Current Estimated Value $556,617

    Last Listing Agent Jon Bell Railey Realty, Inc.

    247 Winding Trail Ln Unit 6B, Oakland, MD 21550
  • Lot 76 S Blakeslee Rd, Oakland, MD 21550
    Lot 76 S Blakeslee Rd, Oakland, MD 21550
    Lot 76 S Blakeslee Rd, Oakland, MD 21550
    /12

    $380,000 Sold May 30, 2025

    Lot 76 S Blakeslee Rd, Oakland, MD 21550

    • Land
    • 1.06 Acres
    • $358,491 per Acre

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    Lot 76 S Blakeslee Rd, Oakland, MD 21550
  • 1056 Sunrise Dr, Oakland, MD 21550
    1056 Sunrise Dr, Oakland, MD 21550
    1056 Sunrise Dr, Oakland, MD 21550
    /60

    $280,000 Sold Nov 14, 2025

    1056 Sunrise Dr, Oakland, MD 21550

    • 4 Beds
    • 2.5 Baths
    • 1,528 Sq Ft
    • Built 1976

    Last Sold Summary

    • $183/SF
    • 59 Days On Market

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    1056 Sunrise Dr, Oakland, MD 21550
  • 26 Arrowhead Ln, Oakland, MD 21550
    26 Arrowhead Ln, Oakland, MD 21550
    26 Arrowhead Ln, Oakland, MD 21550
    /42

    $675,000 Sold Mar 14, 2025

    26 Arrowhead Ln, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • 2,000 Sq Ft
    • Built 1988

    Last Sold Summary

    • $338/SF
    • 389 Days On Market

    Current Estimated Value $693,442

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    26 Arrowhead Ln, Oakland, MD 21550
  • Lot #5 Swan Meadow Dr, Oakland, MD 21550
    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    Lot #5 Swan Meadow Dr, Oakland, MD 21550
    /5

    $135,000 Sold Jun 25, 2025

    Lot #5 Swan Meadow Dr, Oakland, MD 21550

    • Land
    • 10 Acres
    • $13,500 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Rich Orr Railey Realty, Inc.

    Lot #5 Swan Meadow Dr, Oakland, MD 21550
  • 1087 Pergin Farm Rd, Oakland, MD 21550
    1087 Pergin Farm Rd, Oakland, MD 21550
    1087 Pergin Farm Rd, Oakland, MD 21550
    /149

    $2,975,000 Sold Oct 03, 2025

    1087 Pergin Farm Rd, Oakland, MD 21550

    • 6 Beds
    • 5.5 Baths
    • 4,481 Sq Ft
    • Built 1984

    Last Sold Summary

    • $664/SF
    • 16 Days On Market

    Current Estimated Value $2,965,827

    Last Listing Agent Susan Bell Railey Realty, Inc.

    1087 Pergin Farm Rd, Oakland, MD 21550
  • Lot 9 Birchwood Dr, Oakland, MD 21550
    Lot 9 Birchwood Dr, Oakland, MD 21550
    Lot 9 Birchwood Dr, Oakland, MD 21550
    /23

    $18,000 Sold Jul 03, 2025

    Lot 9 Birchwood Dr, Oakland, MD 21550

    • Land
    • 0.8 Acre
    • $22,500 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    Lot 9 Birchwood Dr, Oakland, MD 21550
  • 30 Village Dr Unit 3, Oakland, MD 21550
    30 Village Dr Unit 3, Oakland, MD 21550
    30 Village Dr Unit 3, Oakland, MD 21550
    /35

    $390,000 Sold Dec 12, 2025

    30 Village Dr Unit 3, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 916 Sq Ft
    • Built 2005

    Last Sold Summary

    • $426/SF
    • 34 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    30 Village Dr Unit 3, Oakland, MD 21550
  • 130 Wisp Adventure Rd, McHenry, MD 21541
    130 Wisp Adventure Rd, McHenry, MD 21541
    130 Wisp Adventure Rd, McHenry, MD 21541
    /63

    $699,900 Sold Sep 26, 2025

    130 Wisp Adventure Rd, McHenry, MD 21541

    • 5 Beds
    • 4 Baths
    • 3,105 Sq Ft
    • Built 2021

    Last Sold Summary

    • $225/SF
    • 76 Days On Market

    Current Estimated Value $726,455

    Last Listing Agent Jon Bell Railey Realty, Inc.

    130 Wisp Adventure Rd, McHenry, MD 21541
  • 0 Maryland Hwy, Swanton, MD 21561
    0 Maryland Hwy, Swanton, MD 21561
    0 Maryland Hwy, Swanton, MD 21561
    /15

    $115,000 Sold Mar 13, 2025

    0 Maryland Hwy, Swanton, MD 21561

    • Land
    • 44.02 Acres
    • $2,612 per Acre

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Dan (Sussan) Duggan 1 Real Estate Source LLC

    0 Maryland Hwy, Swanton, MD 21561
  • 422 Underwood Rd, Oakland, MD 21550
    422 Underwood Rd, Oakland, MD 21550
    422 Underwood Rd, Oakland, MD 21550
    /45

    $195,000 Sold Jul 11, 2025

    422 Underwood Rd, Oakland, MD 21550

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1972

    Last Sold Summary

    • $203/SF
    • 17 Days On Market

    Current Estimated Value $198,482

    Last Listing Agent Larry Smith Railey Realty, Inc.

    422 Underwood Rd, Oakland, MD 21550
  • 2360 Garrett Rd, Oakland, MD 21550
    2360 Garrett Rd, Oakland, MD 21550
    /2

    $285,000 Sold Sep 05, 2025

    2360 Garrett Rd, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 0 Days On Market

    Current Estimated Value $290,858

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    2360 Garrett Rd, Oakland, MD 21550
  • 722 Winding Estates Dr, Mc Henry, MD 21541
    722 Winding Estates Dr, Mc Henry, MD 21541
    722 Winding Estates Dr, Mc Henry, MD 21541
    /86

    $770,000 Sold Sep 15, 2025

    722 Winding Estates Dr, Mc Henry, MD 21541

    • 4 Beds
    • 2.5 Baths
    • 2,962 Sq Ft
    • Built 2017

    Last Sold Summary

    • $260/SF
    • 380 Days On Market

    Current Estimated Value $787,021

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    722 Winding Estates Dr, Mc Henry, MD 21541
  • 2805 Shady Dell Rd, Oakland, MD 21550
    2805 Shady Dell Rd, Oakland, MD 21550
    2805 Shady Dell Rd, Oakland, MD 21550
    /47

    $208,550 Sold Sep 26, 2025

    2805 Shady Dell Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1966

    Last Sold Summary

    • $143/SF
    • 42 Days On Market

    Current Estimated Value $221,632

    Last Listing Agent Laura Newhall Taylor Made Deep Creek Vacations & Sales

    2805 Shady Dell Rd, Oakland, MD 21550
  • 197 Black Angus Dr, Oakland, MD 21550
    197 Black Angus Dr, Oakland, MD 21550
    197 Black Angus Dr, Oakland, MD 21550
    /111

    $2,600,000 Sold Oct 20, 2025

    197 Black Angus Dr, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 4,156 Sq Ft
    • Built 1975

    Last Sold Summary

    • $626/SF
    • 15 Days On Market

    Current Estimated Value $2,559,289

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    197 Black Angus Dr, Oakland, MD 21550
  • 19956 Garrett Hwy Unit 6, Oakland, MD 21550
    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    19956 Garrett Hwy Unit 6, Oakland, MD 21550
    /81

    $1,200,000 Sold Jan 16, 2026

    19956 Garrett Hwy Unit 6, Oakland, MD 21550

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft
    • Built 2007

    Last Sold Summary

    • $400/SF
    • 162 Days On Market

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    19956 Garrett Hwy Unit 6, Oakland, MD 21550
  • 4 Laurel Brook Dr, Oakland, MD 21550
    4 Laurel Brook Dr, Oakland, MD 21550
    4 Laurel Brook Dr, Oakland, MD 21550
    /22

    $212,000 Sold Dec 05, 2025

    4 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 166 Days On Market

    Last Listing Agent Eric Crawford Taylor Made Deep Creek Vacations & Sales

    4 Laurel Brook Dr, Oakland, MD 21550
  • 264 Marsh Hill Rd, Mc Henry, MD 21541
    264 Marsh Hill Rd, Mc Henry, MD 21541
    264 Marsh Hill Rd, Mc Henry, MD 21541
    /43

    $324,900 Sold Feb 28, 2025

    264 Marsh Hill Rd, Mc Henry, MD 21541

    • 3 Beds
    • 2.5 Baths
    • 1,897 Sq Ft
    • Built 1991

    Last Sold Summary

    • $171/SF
    • 71 Days On Market

    Current Estimated Value $353,779

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    264 Marsh Hill Rd, Mc Henry, MD 21541
  • 273 Glendale Rd, Oakland, MD 21550
    273 Glendale Rd, Oakland, MD 21550
    273 Glendale Rd, Oakland, MD 21550
    /74

    $2,450,000 Sold Oct 30, 2025

    273 Glendale Rd, Oakland, MD 21550

    • 5 Beds
    • 5.5 Baths
    • 5,141 Sq Ft
    • Built 2008

    Last Sold Summary

    • $477/SF
    • 7 Days On Market

    Current Estimated Value $2,478,468

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    273 Glendale Rd, Oakland, MD 21550
  • 101 Sunset Dr, Oakland, MD 21550
    101 Sunset Dr, Oakland, MD 21550
    101 Sunset Dr, Oakland, MD 21550
    /66

    $499,000 Sold Jul 15, 2025

    101 Sunset Dr, Oakland, MD 21550

    • 3 Beds
    • 2.5 Baths
    • 3,024 Sq Ft
    • Built 1987

    Last Sold Summary

    • $165/SF
    • 11 Days On Market

    Current Estimated Value $484,234

    Last Listing Agent Rich Orr Railey Realty, Inc.

    101 Sunset Dr, Oakland, MD 21550
  • Lot 31 Fawn Dr, Oakland, MD 21550
    Lot 31 Fawn Dr, Oakland, MD 21550
    Lot 31 Fawn Dr, Oakland, MD 21550
    /24

    $17,000 Sold Aug 22, 2025

    Lot 31 Fawn Dr, Oakland, MD 21550

    • Land
    • 0.69 Acre
    • $24,638 per Acre

    Last Sold Summary

    • 19 Days On Market

    Last Listing Agent Nick Fratz-Orr Railey Realty, Inc.

    Lot 31 Fawn Dr, Oakland, MD 21550
  • 0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
    /4

    $115,000 Sold Sep 26, 2025

    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550

    • Land
    • 0.52 Acre
    • $221,154 per Acre

    Last Sold Summary

    • 32 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    0 Paradise Heights Rd Unit MDGA2010024, Oakland, MD 21550
  • 170 Tannery Rd, Oakland, MD 21550
    170 Tannery Rd, Oakland, MD 21550
    170 Tannery Rd, Oakland, MD 21550
    /28

    $174,500 Sold Oct 30, 2025

    170 Tannery Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft
    • Built 1974

    Last Sold Summary

    • $94/SF
    • 96 Days On Market

    Current Estimated Value $176,086

    Last Listing Agent Jonathan Minerick Homecoin.com

    170 Tannery Rd, Oakland, MD 21550
  • 202 Penelacre Ln, Oakland, MD 21550
    202 Penelacre Ln, Oakland, MD 21550
    202 Penelacre Ln, Oakland, MD 21550
    /85

    $975,000 Sold Nov 24, 2025

    202 Penelacre Ln, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • Built 1985

    Last Sold Summary

    • $592/SF
    • 12 Days On Market

    Last Listing Agent Justin Liller Railey Realty, Inc.

    202 Penelacre Ln, Oakland, MD 21550
  • 870 Holy Cross Dr, Oakland, MD 21550
    870 Holy Cross Dr, Oakland, MD 21550
    870 Holy Cross Dr, Oakland, MD 21550
    /93

    $3,375,000 Sold Nov 13, 2025

    870 Holy Cross Dr, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 5,681 Sq Ft
    • Built 2007

    Last Sold Summary

    • $594/SF
    • 5 Days On Market

    Last Listing Agent Russell Bounds Railey Realty, Inc.

    870 Holy Cross Dr, Oakland, MD 21550
  • 5 Warnick Way, Oakland, MD 21550
    5 Warnick Way, Oakland, MD 21550
    5 Warnick Way, Oakland, MD 21550
    /10

    $30,000 Sold Apr 21, 2025

    5 Warnick Way, Oakland, MD 21550

    • Land
    • 0.84 Acre
    • $35,714 per Acre

    Last Sold Summary

    • 590 Days On Market

    Last Listing Agent Nicole Jackson Railey Realty, Inc.

    5 Warnick Way, Oakland, MD 21550

Showing Results 241 - 280, Page 7 of 8

Maryland Garrett County Oakland 21550

Recently Sold Real Estate & Homes in 21550

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