44445 Medleys Neck Road

Closed 10/11/21

Sold

Last Sold Price

$429,900

3 beds2 baths2,251 sqft$191/sqft

44445 Medleys Neck Rd, Leonardtown, MD 20650

Single FamilyProperty Type

4.99 acresLot Size

1989Year Built

$191/sq ftPrice per sq ft

6 carsParking Spaces

Description

Welcome Home to this lovely unique one story home located on 4.99 secluded park-like acres in Leonardtown, Maryland. Enjoy relaxing on the front porch taking in the wildlife around your very own Pond! Or maybe you prefer to relax in the 16 x 32 heated above ground pool w/ a new liner and includes a 500 gallon underground propane tank; Or would you like to just relax in the hot tub located just off the back deck?! Rest assured whatever your lifestyle, you will enjoy every minute of it here! This 2,251...Welcome Home to this lovely unique one story home located on 4.99 secluded park-like acres in Leonardtown, Maryland. Enjoy relaxing on the front porch taking in the wildlife around your very own Pond! Or maybe you prefer to relax in the 16 x 32 heated above ground pool w/ a new liner and includes a 500 gallon underground propane tank; Or would you like to just relax in the hot tub located just off the back deck?! Rest assured whatever your lifestyle, you will enjoy every minute of it here! This 2,251 sq ft beauty is one story living at its best. Tons of possibility for future expansion or covered entertaining offered in the attached finished carport. Wood flooring, ceramic tile and some fresh new updates that include brand new paint, and some beautiful new luxury vinyl plank flooring. An expansive owner’s suite that includes an en-suite bathroom with a jacuzzi tub, separate shower and dual sinks. Reap the advantages of lower utility bills with the Geothermal heating system. For extra chilly nights there is a fireplace and a wood burning stove in the family room. An impressive large second family room with soaring ceilings and a built-in sauna. They whole house generator will give you the peace of mind of never being without electric. Plenty of storage for personal or business use in the HUGE 30 x 40 metal outbuilding with a concrete floor. Hurry schedule your appointment to see this home soon because it will not last long! This is an As Is Sale.

Listed by: Mary J Chambers 301.659.2440 mary@marychambersrealestate.com • RE/MAX Realty Group

Listing closed: 10/11/2021 12:00 AM • Source: BRIGHT, MLS#: MDSM2001888

Recent comparable sales

Median sold price

$465,000

Avg days on market

Sale-to-list ratio

100.8%

1/37

$465,000

Sold 11/21/25

3
Bedrooms: 2
Bathrooms: 2,304
Square Feet: 2.24
Acres

44504 Watson Lane, Leonardtown, MD 20650

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Sold 01/08/25

3
Bedrooms: 2
Bathrooms: 2,280
Square Feet: 2
Acres

20400 Chingville Road, Leonardtown, MD 20650

1/88

$475,203

Sold 03/02/26

3
Bedrooms: 2
Bathrooms: 2,458
Square Feet: 2.39
Acres

20697 Chingville Road, Leonardtown, MD 20650

1/46

$410,000

Sold 11/27/24

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Bedrooms: 3
Bathrooms: 2,116
Square Feet: 9.66
Acres

20418 Scarlet Tanager Way, Leonardtown, MD 20650

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Bedrooms: 2
Bathrooms: 1,557
Square Feet: 1.37
Acres

20250 Hawks Way, Leonardtown, MD 20650

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Bedrooms: 2
Bathrooms: 1,732
Square Feet: 2.43
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43543 Bayberry Court, Leonardtown, MD 20650

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Bedrooms: 2
Bathrooms: 1,508
Square Feet: 1
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20958 Camp Cosoma Road, Leonardtown, MD 20650

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Bedrooms: 2
Bathrooms: 1,644
Square Feet: 1.4
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44731 Blake Creek Road, Leonardtown, MD 20650

a view of a house with a porch and furniture

1/75

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4
Bedrooms: 2
Bathrooms: 2,400
Square Feet: 0.52
Acres

43985 Main Way Road, Leonardtown, MD 20650

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Location

Listing Courtesy of RE/MAX Realty Group

Sold By CENTURY 21 New Millennium

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$2,490 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,185

Property Taxes

$305

HOA Dues

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Property Information for 44445 Medleys Neck Road

Property Details

Taxes: $3,659 / year
MLS Type: Residential / Fee Simple
County: St. Mary's County
Tax ID Number: 1902026244
Ownership: Fee Simple
Condo Coop Association: No
HOA: No
Structure Type: Detached
Style: Ranch/Rambler
Levels/Stories: 1
Waterfront: No
Views: Pond
Garage: Yes
Subdivision: NONE AVAILABLE
Subdivision: NONE AVAILABLE (SAINT MARYS MD)
Total Parking Spaces: 6
Central Air: No
Basement: No
Above Grade Finished SQFT: 2,251.00
Above Grade Fin SQFT Source: Assessor
Below Grade Finished SQFT: .00
Below Grade Fin SQFT Source: Assessor
Below Grade Unfinished SQFT: .00
Below Grade Unfin SQFT Source: Assessor
Total Below Grade SQFT: .00
Total Below Grade SQFT Source: Assessor
New Construction: No
Property Condition: Excellent

Building Information

Stories: 1
Year Built: 1989
Lot Size: 4.99 AC / 217,364 SF

Location

In City Limits: No
School District Name: ST. MARY'S COUNTY PUBLIC SCHOOLS

School District County ID: 121138839208
SchoolDistrictSource: 3rd Party
Elementary School: PINEY POINT (SAINT MARYS MD)
ElementarySchoolSource: 3rd Party
Middle Or Junior School: LEONARDTOWN (SAINT MARYS MD)
MiddleSchoolSource: 3rd Party
High School: LEONARDTOWN (SAINT MARYS MD)
HighSchoolSource: 3rd Party
County: SAINT MARYS

Waterfront / Water Access

Water View: Yes
Water Access: No

Water Oriented: No
Navigable Water: No
Tidal Water: No
Riparian Rights Y/N: No

Association / Community Info

Senior Community: No

Taxes and Assessment

Tax Year: 2021
Tax Assessed Value: $357,733

Year Assessed: 2021
County Tax: $3,186
Improvement Assessed Value: $248,600
Land Assessed Value: $134,900
Clean Green Assessed: No
Land Use Code: 010
Section: 2
Zoning: RPD
Tax Lot: 6
Tax Page Number: 42
Automatically Update Tax Values Y/N: Yes
TaxDataUpdatedYN: No

Rooms

Main

# Bedrooms Count Main Level: 3
# Bathrooms Count Main Level: 2

# Bathrooms Full Main Level: 2

Rooms

Room List: Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Laundry, Primary Bathroom, Full Bath
Stories: Main

Rooms Information

Room 1

Room Type: Family Room
Room Level: Main

Room Exists: Yes

Room 2

Room Type: Dining Room
Room Level: Main

Room Exists: Yes

Room 3

Room Type: Kitchen
Room Level: Main

Room Exists: Yes

Room 4

Room Type: Family Room
Room Level: Main

Room Exists: Yes

Room 5

Room Type: Primary Bedroom
Room Level: Main

Room Exists: Yes

Room 6

Room Type: Primary Bathroom
Room Level: Main

Room Exists: Yes

Room 7

Room Type: Bedroom 2
Room Level: Main

Room Exists: Yes

Room 8

Room Type: Bedroom 3
Room Level: Main

Room Exists: Yes

Room 9

Room Type: Full Bath
Room Level: Main

Room Exists: Yes

Room 10

Room Type: Laundry
Room Level: Main

Room Exists: Yes

Building Info

Total Finished SQFT: 2,251.00
Total Finished SQFT Source: Assessor

Tax Total Finished SQFT: 2,251.00
Total SQFT: 2,251.00
Total SQFT Source: Assessor
Construction Materials: Brick, Vinyl Siding
Ext Main Mid-res: http://bright-media01.prd.brightmls.com/bright/images/0000/8010/3646/8038/801036468038_512_384_WM_N0ebZWjO3dVA61n8.jpg
Flooring Type: Carpet, Ceramic Tile, Hardwood, Luxury Vinyl Plank
Foundation Details: Crawl Space
Room and Floor: Bedrooms-Main Level-1, Bedrooms-Main Level-2, Bedrooms-Main Level-3, Bathrooms Full-Main Level-1, Bathrooms Full-Main Level-2
# Bathrooms Full: 2
Other Structure: Shed, Garage(s)

Lot / Land Information

Lot Size Source: Assessor
Fencing: Wood

Parcel ID: 14986256
Additional Parcels: No

Parking

Type Of Parking: Attached Carport, Driveway, Detached Garage
Num of Detached Garage Spaces: 4

Total Garage Spaces: 4
Attached Carport - # of Spaces: 2.0
Carport Spaces Count: 2
Garage Features: Garage - Front Entry, Oversized

Interior Features

Fireplace: Yes
Fireplaces Count: 1

Fireplace Features: Brick, Wood
Appliances: Refrigerator, Stove, Dishwasher, Exhaust Fan
Accessibility Features: None
Security Features: Electric Alarm
Laundry Type: Main Floor
Virtual Tour URL Unbranded: https://properties.myhouselens.com/ub/44899/44445%20Medleys%20Neck%20Road,%20Leonardtown,%20MD%2020650

Exterior Features

Exterior Features: Hot Tub
Pool: No Pool

Utilities

Utilities: Propane, Electric Available
Heating: Yes

Cooling Type: Geothermal
Cooling Fuel: Geothermal
Heating Type: Forced Air
Heating Fuel: Geo-thermal
Hot Water: Electric
Water Source: Well
Sewer Septic: Private Septic Tank

Confidential Data

Listing Office

List Agent AOR: Southern Maryland Association of REALTORS
List Agent URL: MaryChambersrealestate.com

Property History for 44445 Medleys Neck Road

Date	Event & Source	Price	Appreciation
Oct 12, 2021	Closed (Public Record) Public Record #1474763303	$429,900	+2.2% / yr
Oct 11, 2021	Closed BRIGHT #MDSM2001888	$429,900	—
Sep 13, 2021	Pending BRIGHT #MDSM2001888		—
Sep 10, 2021	Listed (Active) BRIGHT #MDSM2001888	$429,900	—
Jan 14, 2020	Expired BRIGHT #MDSM164506	$399,900	—
Nov 2, 2019	Withdrawn BRIGHT #MDSM164506	$399,900	—
Aug 24, 2019	Listed (Active) BRIGHT #MDSM164506	$425,000	—
May 15, 2017	Closed (Public Record) Public Record #599638086	$390,000	—
May 15, 2017	Closed BRIGHT #1001113331	$390,000	—
Mar 14, 2017	Pending BRIGHT #1001113331		—
Feb 3, 2017	Listed (Active) BRIGHT #1001113331	$374,900	—

Date	Event & Source	Price
10/12/2021	Closed (Public Record) Public Record #1474763303	$429,900 +2.2% / yr
10/11/2021	Closed BRIGHT #MDSM2001888	$429,900
09/13/2021	Pending BRIGHT #MDSM2001888	—
09/10/2021	Listed (Active) BRIGHT #MDSM2001888	$429,900
01/14/2020	Expired BRIGHT #MDSM164506	$399,900
11/02/2019	Withdrawn BRIGHT #MDSM164506	$399,900
08/24/2019	Listed (Active) BRIGHT #MDSM164506	$425,000
05/15/2017	Closed (Public Record) Public Record #599638086	$390,000
05/15/2017	Closed BRIGHT #1001113331	$390,000
03/14/2017	Pending BRIGHT #1001113331	—
02/03/2017	Listed (Active) BRIGHT #1001113331	$374,900

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 44445 Medleys Neck Road

Taxable ValueLand-Additions-Total-

Tax Record2025$4,672 ($389 / month)

Home Facts

Beds0Baths2Total Finished SqFt2,251 SqFtAbove Grade Finished SqFt2,251 SqFtStories1Lot Size217,364 SqFtStyleSingle Family ResidenceYear Built1989Year Renovated1989ZoningRPDCountyST. MARY'SAPN02-026244

Schools near 44445 Medleys Neck Road

This home is within St. Mary's County Public Schools.


Rating	School	Type	Grades	Distance
7/10	Piney Point Elementary School	Public - Serves this home	PK to 5	3.9 mi
9/10	Leonardtown Middle School	Public - Serves this home	6 to 8	5.3 mi
8/10	Leonardtown High School	Public - Serves this home	9 to 12	5.0 mi
9/10	Chesapeake Charter School	Charter - Choice school	K to 8	2.9 mi
NR	Dr. James A. Forrest Career And Technology Center	Public - Nearby school	9 to 12	5.1 mi
NR	The Kings Christian Academy	Private - Nearby school	PK to 12	1.5 mi
NR	Little Flower School	Private - Nearby school	PK to 8	2.1 mi


Rating	School	Distance
7/10	Piney Point Elementary School PublicPK to 5 Serves this home	3.9 mi
9/10	Leonardtown Middle School Public6 to 8 Serves this home	5.3 mi
8/10	Leonardtown High School Public9 to 12 Serves this home	5.0 mi
9/10	Chesapeake Charter School CharterK to 8 Choice school	2.9 mi
NR	Dr. James A. Forrest Career And Technology Center Public9 to 12 Nearby school	5.1 mi
NR	The Kings Christian Academy PrivatePK to 12 Nearby school	1.5 mi
NR	Little Flower School PrivatePK to 8 Nearby school	2.1 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

Address	Sold price	Beds	Baths	Sqft	Lot (Sqft)
This home: 44445 Medleys Neck Road, Leonardtown, MD 20650	$429,900	3	2	2,251	217,364
44465 Mane Pooh Lane, Leonardtown, MD 20650	–	–	2	1,652	719,611
44403 Medleys Neck Road, Leonardtown, MD 20650	$575,000	3	3	2,647	213,880
44471 Hawks Nest Estate Lane, Leonardtown, MD 20650	$200,000	3	1	1,824	217,364
20250 Hawks Way, Leonardtown, MD 20650	$519,900	3	2	1,557	59,677
20280 Natures Way, Leonardtown, MD 20650	–	–	3.5	4,324	217,800
44450 Medleys Neck Road, Leonardtown, MD 20650	–	–	1.5	1,440	53,143
44447 Watson Lane, Leonardtown, MD 20650	–	–	2	1,339	87,120
44484 Medleys Neck Road, Leonardtown, MD 20650	–	–	2	1,504	145,055
44074 Medleys Neck Road, Leonardtown, MD 20650	$675,000	4	3	3,830	102,366
20306 Chingville Road, Leonardtown, MD 20650	–	–	2	1,768	98,010
44455 Watson Lane, Leonardtown, MD 20650	–	–	2	1,848	87,120
20275 Natures Way, Leonardtown, MD 20650	–	–	3	3,280	217,800
44461 Mane Pooh Lane, Leonardtown, MD 20650	–	–	2	1,352	130,680
44485 Watson Lane, Leonardtown, MD 20650	$50,000	–	2	1,286	131,116
44456 Watson Lane, Leonardtown, MD 20650	–	–	2	1,728	151,589

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Listing Courtesy of RE/MAX Realty Group

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 07/20/2026 06:00 PM

Leonardtown, MD

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