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Recently Sold Callaway Homes

Section Image
  • 20861 Harlequin Ln, Callaway, MD 20620
    20861 Harlequin Ln, Callaway, MD 20620
    20861 Harlequin Ln, Callaway, MD 20620
    /4

    $249,500 Sold Oct 27, 2025

    20861 Harlequin Ln, Callaway, MD 20620

    • 2 Beds
    • 2.5 Baths
    • 1,693 Sq Ft
    • Built 1988

    Last Sold Summary

    • $147/SF
    • 0 Days On Market

    Current Estimated Value $254,226

    Last Listing Agent Cathy Rose Samson Properties

    20861 Harlequin Ln, Callaway, MD 20620
  • 44913 Widgeon Place, Callaway, MD 20620
    44913 Widgeon Place, Callaway, MD 20620
    44913 Widgeon Place, Callaway, MD 20620
    /49

    $469,900 Sold Mar 27, 2026

    44913 Widgeon Place, Callaway, MD 20620

    • 4 Beds
    • 2.5 Baths
    • 2,430 Sq Ft
    • Built 2000

    Last Sold Summary

    • $193/SF
    • 67 Days On Market

    Current Estimated Value $471,979

    Last Listing Agent Jaye Hercules RE/MAX Realty Group

    44913 Widgeon Place, Callaway, MD 20620
  • 44906 Golden Eye Ct, Callaway, MD 20620
    44906 Golden Eye Ct, Callaway, MD 20620
    44906 Golden Eye Ct, Callaway, MD 20620
    /118

    $610,000 Sold Nov 28, 2025

    44906 Golden Eye Ct, Callaway, MD 20620

    • 6 Beds
    • 5 Baths
    • 6,006 Sq Ft
    • Built 2006

    Last Sold Summary

    • $102/SF
    • 57 Days On Market

    Current Estimated Value $618,533

    Last Listing Agent Kelly Padgett CENTURY 21 New Millennium

    44906 Golden Eye Ct, Callaway, MD 20620
  • 20966 Black Duck Ct, Callaway, MD 20620
    20966 Black Duck Ct, Callaway, MD 20620
    20966 Black Duck Ct, Callaway, MD 20620
    /43

    $420,000 Sold Nov 21, 2025

    20966 Black Duck Ct, Callaway, MD 20620

    • 3 Beds
    • 3.5 Baths
    • 2,264 Sq Ft
    • Built 1998

    Last Sold Summary

    • $186/SF
    • 88 Days On Market

    Current Estimated Value $426,764

    Last Listing Agent Farrah Fuchs Redfin Corp

    20966 Black Duck Ct, Callaway, MD 20620
  • 21549 Point Lookout Rd, Leonardtown, MD 20650
    21549 Point Lookout Rd, Leonardtown, MD 20650
    21549 Point Lookout Rd, Leonardtown, MD 20650
    /43

    $710,000 Sold Jul 24, 2025

    21549 Point Lookout Rd, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 3,153 Sq Ft
    • Built 2001

    Last Sold Summary

    • $225/SF
    • 6 Days On Market

    Current Estimated Value $718,670

    Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, Leonardtown, MD 20650
  • 44892 Golden Eye Ct, Callaway, MD 20620
    44892 Golden Eye Ct, Callaway, MD 20620
    44892 Golden Eye Ct, Callaway, MD 20620
    /48

    $475,000 Sold Feb 16, 2026

    44892 Golden Eye Ct, Callaway, MD 20620

    • 4 Beds
    • 2.5 Baths
    • 2,536 Sq Ft
    • Built 2002

    Last Sold Summary

    • $187/SF
    • 103 Days On Market

    Current Estimated Value $483,069

    Last Listing Agent Dawn Riley RE/MAX One

    44892 Golden Eye Ct, Callaway, MD 20620
  • 20955 Aster Dr, Callaway, MD 20620
    20955 Aster Dr, Callaway, MD 20620
    20955 Aster Dr, Callaway, MD 20620
    /41

    $541,000 Sold Jul 25, 2025

    20955 Aster Dr, Callaway, MD 20620

    • 4 Beds
    • 2.5 Baths
    • 2,356 Sq Ft
    • Built 1996

    Last Sold Summary

    • $230/SF
    • 17 Days On Market

    Current Estimated Value $553,079

    Last Listing Agent Carol Kalmus-Choporis CENTURY 21 New Millennium

    20955 Aster Dr, Callaway, MD 20620
  • 20314 Brent Ln, Callaway, MD 20620
    20314 Brent Ln, Callaway, MD 20620
    /2

    $345,000 Sold Feb 03, 2026

    20314 Brent Ln, Callaway, MD 20620

    • 3 Beds
    • 2 Baths
    • 1,580 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Above List Price
    • $218/SF
    • 9 Days On Market

    Current Estimated Value $339,441

    Last Listing Agent Steven Carroll Berkshire Hathaway HomeServices PenFed Realty

    20314 Brent Ln, Callaway, MD 20620
  • 44968 Hewitt Rd, Callaway, MD 20620
    44968 Hewitt Rd, Callaway, MD 20620
    44968 Hewitt Rd, Callaway, MD 20620
    /33

    $575,000 Sold Jan 09, 2026

    44968 Hewitt Rd, Callaway, MD 20620

    • 3 Beds
    • 2 Baths
    • 792 Sq Ft
    • Built 1975

    Last Sold Summary

    • $726/SF
    • 5 Days On Market

    Last Listing Agent Florentina Killian CENTURY 21 New Millennium

    44968 Hewitt Rd, Callaway, MD 20620
  • 20903 Jo Marie Way, Callaway, MD 20620
    20903 Jo Marie Way, Callaway, MD 20620
    20903 Jo Marie Way, Callaway, MD 20620
    /29

    $289,900 Sold Sep 15, 2025

    20903 Jo Marie Way, Callaway, MD 20620

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft
    • Built 1998

    Last Sold Summary

    • $220/SF
    • 2 Days On Market

    Current Estimated Value $291,822

    Last Listing Agent DJ Brady EXP Realty, LLC

    20903 Jo Marie Way, Callaway, MD 20620
  • 11800 Point Lookout Rd, Scotland, MD 20687
    11800 Point Lookout Rd, Scotland, MD 20687
    11800 Point Lookout Rd, Scotland, MD 20687
    /7

    $25,000 Sold Jul 03, 2025

    11800 Point Lookout Rd, Scotland, MD 20687

    • Land
    • 37,897 Sq Ft
    • $28,736 per Acre

    Last Sold Summary

    • 62 Days On Market

    Last Listing Agent Trish Wallmark RE/MAX One

    11800 Point Lookout Rd, Scotland, MD 20687
  • 44964 Hewitt Rd, Callaway, MD 20620
    44964 Hewitt Rd, Callaway, MD 20620
    44964 Hewitt Rd, Callaway, MD 20620
    /35

    $329,000 Sold Aug 08, 2025

    44964 Hewitt Rd, Callaway, MD 20620

    • 3 Beds
    • 1 Bath
    • 1,242 Sq Ft
    • Built 2012

    Last Sold Summary

    • $265/SF
    • 60 Days On Market

    Current Estimated Value $340,058

    Last Listing Agent Alan Smith CENTURY 21 New Millennium

    44964 Hewitt Rd, Callaway, MD 20620
  • 45151 Knotts Dr, Callaway, MD 20620
    45151 Knotts Dr, Callaway, MD 20620
    45151 Knotts Dr, Callaway, MD 20620
    /35

    $545,000 Sold Sep 23, 2025

    45151 Knotts Dr, Callaway, MD 20620

    • 5 Beds
    • 4 Baths
    • 2,736 Sq Ft
    • Built 1996

    Last Sold Summary

    • $199/SF
    • 40 Days On Market

    Last Listing Agent Gina Gargeu Century 21 Downtown

    45151 Knotts Dr, Callaway, MD 20620
  • 21034 Aster Dr, Callaway, MD 20620
    21034 Aster Dr, Callaway, MD 20620
    21034 Aster Dr, Callaway, MD 20620
    /65

    $620,000 Sold Jul 15, 2025

    21034 Aster Dr, Callaway, MD 20620

    • 4 Beds
    • 3.5 Baths
    • 3,228 Sq Ft
    • Built 1996

    Last Sold Summary

    • $192/SF
    • 4 Days On Market

    Current Estimated Value $618,827

    Last Listing Agent Cynthia Crispell CENTURY 21 New Millennium

    21034 Aster Dr, Callaway, MD 20620
  • 21027 Hunting Quarter Dr, Callaway, MD 20620
    21027 Hunting Quarter Dr, Callaway, MD 20620
    21027 Hunting Quarter Dr, Callaway, MD 20620
    /56

    $505,000 Sold May 30, 2025

    21027 Hunting Quarter Dr, Callaway, MD 20620

    • 4 Beds
    • 2.5 Baths
    • 2,368 Sq Ft
    • Built 1999

    Last Sold Summary

    • $213/SF
    • 2 Days On Market

    Current Estimated Value $515,313

    Last Listing Agent Connie Gunn CENTURY 21 New Millennium

    21027 Hunting Quarter Dr, Callaway, MD 20620
  • 20801 Harlequin Ln, Callaway, MD 20620
    20801 Harlequin Ln, Callaway, MD 20620
    20801 Harlequin Ln, Callaway, MD 20620
    /25

    $280,000 Sold Feb 13, 2026

    20801 Harlequin Ln, Callaway, MD 20620

    • 4 Beds
    • 2.5 Baths
    • 1,693 Sq Ft
    • Built 1987

    Last Sold Summary

    • $165/SF
    • 37 Days On Market

    Current Estimated Value $278,216

    Last Listing Agent Ben Kessie RE/MAX Galaxy

    20801 Harlequin Ln, Callaway, MD 20620
  • 44895 Canvas Back Dr, Callaway, MD 20620
    44895 Canvas Back Dr, Callaway, MD 20620
    44895 Canvas Back Dr, Callaway, MD 20620
    /30

    $289,900 Sold Jan 15, 2026

    44895 Canvas Back Dr, Callaway, MD 20620

    • 3 Beds
    • 1.5 Baths
    • 1,488 Sq Ft
    • Built 1991

    Last Sold Summary

    • $195/SF
    • 8 Days On Market

    Current Estimated Value $284,773

    Last Listing Agent Michelle Camaioni RE/MAX One

    44895 Canvas Back Dr, Callaway, MD 20620
  • 20035 Piney Point Rd, Callaway, MD 20620
    20035 Piney Point Rd, Callaway, MD 20620
    20035 Piney Point Rd, Callaway, MD 20620
    /35

    $340,000 Sold Nov 21, 2025

    20035 Piney Point Rd, Callaway, MD 20620

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1970

    Last Sold Summary

    • $228/SF
    • 13 Days On Market

    Current Estimated Value $350,765

    Last Listing Agent Connie Gunn CENTURY 21 New Millennium

    20035 Piney Point Rd, Callaway, MD 20620
  • 20903 Hunting Quarter Dr, Callaway, MD 20620
    20903 Hunting Quarter Dr, Callaway, MD 20620
    20903 Hunting Quarter Dr, Callaway, MD 20620
    /61

    $429,900 Sold May 30, 2025

    20903 Hunting Quarter Dr, Callaway, MD 20620

    • 4 Beds
    • 3 Baths
    • 2,728 Sq Ft
    • Built 1994

    Last Sold Summary

    • $158/SF
    • 27 Days On Market

    Current Estimated Value $441,009

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    20903 Hunting Quarter Dr, Callaway, MD 20620
  • 44504 Watson Ln, Leonardtown, MD 20650
    44504 Watson Ln, Leonardtown, MD 20650
    44504 Watson Ln, Leonardtown, MD 20650
    /36

    $465,000 Sold Nov 21, 2025

    44504 Watson Ln, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,304 Sq Ft
    • Built 2003

    Last Sold Summary

    • $202/SF
    • 17 Days On Market

    Current Estimated Value $474,991

    Last Listing Agent Danny Morris O'Brien Realty ERA Powered

    44504 Watson Ln, Leonardtown, MD 20650
  • 20904 Hunting Quarter Dr, Callaway, MD 20620
    20904 Hunting Quarter Dr, Callaway, MD 20620
    /2

    $399,000 Sold Sep 19, 2025

    20904 Hunting Quarter Dr, Callaway, MD 20620

    • 3 Beds
    • 3 Baths
    • 1,222 Sq Ft
    • Built 1994

    Last Sold Summary

    • $327/SF
    • 0 Days On Market

    Current Estimated Value $405,826

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    20904 Hunting Quarter Dr, Callaway, MD 20620
  • 21500 Point Lookout Rd, Callaway, MD 20620
    21500 Point Lookout Rd, Callaway, MD 20620
    21500 Point Lookout Rd, Callaway, MD 20620
    /97

    $600,000 Sold May 06, 2025

    21500 Point Lookout Rd, Callaway, MD 20620

    • 3 Beds
    • 3 Baths
    • 3,605 Sq Ft
    • Built 1955

    Last Sold Summary

    • $166/SF
    • 253 Days On Market

    Current Estimated Value $595,393

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    21500 Point Lookout Rd, Callaway, MD 20620
  • 44968 Hewitt Rd, Callaway, MD 20620
    44968 Hewitt Rd, Callaway, MD 20620
    44968 Hewitt Rd, Callaway, MD 20620
    /6

    $74,200 Sold May 02, 2025

    44968 Hewitt Rd, Callaway, MD 20620

    • Land
    • 1 Acre
    • $74,200 per Acre

    Last Sold Summary

    • 13 Days On Market

    Last Listing Agent Carley Cooper Alex Cooper Auctioneers, Inc.

    44968 Hewitt Rd, Callaway, MD 20620
  • 44889 Mallard Place, Callaway, MD 20620
    44889 Mallard Place, Callaway, MD 20620
    44889 Mallard Place, Callaway, MD 20620
    /37

    $450,000 Sold Jul 11, 2025

    44889 Mallard Place, Callaway, MD 20620

    • 4 Beds
    • 3 Baths
    • 2,154 Sq Ft
    • Built 1999

    Last Sold Summary

    • $209/SF
    • 51 Days On Market

    Current Estimated Value $464,291

    Last Listing Agent Jesieryl Hartzer CENTURY 21 New Millennium

    44889 Mallard Place, Callaway, MD 20620
  • 44871 Rickle Dr, Callaway, MD 20620
    44871 Rickle Dr, Callaway, MD 20620
    44871 Rickle Dr, Callaway, MD 20620
    /62

    $465,000 Sold Aug 12, 2025

    44871 Rickle Dr, Callaway, MD 20620

    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft
    • Built 1996

    Last Sold Summary

    • $302/SF
    • 41 Days On Market

    Current Estimated Value $473,961

    Last Listing Agent Charlotte Long EXP Realty, LLC

    44871 Rickle Dr, Callaway, MD 20620
  • 44826 Wood Duck Ln, Callaway, MD 20620
    44826 Wood Duck Ln, Callaway, MD 20620
    44826 Wood Duck Ln, Callaway, MD 20620
    /21

    $261,000 Sold Apr 17, 2026

    44826 Wood Duck Ln, Callaway, MD 20620

    • 3 Beds
    • 1.5 Baths
    • 1,188 Sq Ft
    • Built 1990

    Last Sold Summary

    • 2% Below List Price
    • $220/SF
    • 3 Days On Market

    Current Estimated Value $263,411

    Last Listing Agent Clara Cretsinger CENTURY 21 New Millennium

    44826 Wood Duck Ln, Callaway, MD 20620
  • 44646 Medleys Neck Rd, Leonardtown, MD 20650
    44646 Medleys Neck Rd, Leonardtown, MD 20650
    /2

    $50,000 Sold Jan 23, 2026

    44646 Medleys Neck Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 924 Sq Ft
    • Built 1999

    Last Sold Summary

    • $54/SF
    • 229 Days On Market

    Last Listing Agent Ron Lord Home Towne Real Estate

    44646 Medleys Neck Rd, Leonardtown, MD 20650
Maryland St Marys County Leonardtown Callaway

Recently Sold Real Estate & Homes in Callaway, Leonardtown

Learn more about living in Callaway

Frequently Asked Questions

What is the average time to sell a house in Callaway, MD?
The houses for sale in Callaway, MD spend an average of 45 days on the market.
What is the number of active homes for sale in Callaway, MD?
There are 0 active homes for sale in Callaway, MD.

Home Trends in Callaway, MD

On average, homes in Callaway, Leonardtown sell after 45 days on the market compared to the national average of 56 days. The median sale price for homes in Callaway, Leonardtown over the last 12 months is $457,500, up 29% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$457,500
Median Single Family Sale Price
$467,450
Median Townhouse Sale Price
$280,000
Average Price Per Sq Ft
$211
Number of Homes for Sale
0
Last 12 months Home Sales
24
Months of Supply
0.00
Median List Price
$457,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
29%
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