OFF MARKET

Off Market Nov 2024 for $575K

$621,902

Est. refi paymentEst. refi $4,568/mo

•

2,647

sq ft

44403 Medleys Neck Rd, Leonardtown, MD 20650

About this home

This beautiful, one of a kind, contemporary style home has plenty of character and is awaiting its new owners. Prepare to be wowed upon entering the front door when you’re greeted by a massive great room to the left with gorgeous cathedral ceilings, a brick wood burning fireplace and an abundance of windows with natural lighting. To the right you’ll see the formal living room with a large bay window and window seat overlooking the front yard. Down the hallway, you’ll discover the magnificent kitchen complete with a center island, cook top, wall oven, and a brand new refrigerator and new dishwasher. You’ll love the ample amount of cabinets and the pantry for storage, as well as the open concept layout for cooking and dining. All 3 bedrooms can be found upstairs, including the incredible primary suite with an enormous walk in closet and primary bathroom that has double vanity sinks, a soaking tub and walk in shower. Complete with built in book shelves, a window seat, tall ceilings and recess lighting, this space is sure to impress! The primary bedroom also has a balcony overlooking the back yard, perfect for enjoying a cup of coffee in the morning and listening to the sounds of nature. Additional features include several original wooden pocket doors throughout the home, a central vacuum system, and an original (vintage) intercom/radio. Wait! There’s More! This home also has an attached two car garage with a work bench/ shelving and electric doors with remote access. Step outside and enjoy the amazing deck and gazebo, perfect for entertaining guests and relaxing. The back yard also has a wooden privacy fence, perfect for pets. This property sits on nearly 5 Acres in a highly sought after location in Leonardtown with no HOA. The large 12’ x 16’ lean-to shed conveys and is perfect for the storage of lawn equipment, toys and tools. This home has a brand new roof (2024) and the furnace was replaced approximately 4 years ago and has been maintained regularly, giving the new owner peace of mind for years to come. Make an appointment today and come see it before it’s gone! You don’t want to miss this one!

Single-familyProperty Type

1992Year Built

4.91 acresLot Size

$235Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Chelsey Nelson • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Bought with Jennifer Goddard • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #MDSM2021042

Redfin Estimate

$621,902

$47K since sold in November 2024$2,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 2.9% higher than the average sale price ($604K) of 5 comparable homes.

SOLD MAY 14, 2026
$727,360
A
4 beds2.5 baths2,972 sq ft
43500 Deer Run Ct, Leonardtown, MD 20650
SOLD AUG 10, 2026
$610,000
B
4 beds3 baths2,381 sq ft
19068 Mallard Creek Ct, Valley Lee, MD 20692
SOLD OCT 1, 2025
$600,000
C
4 beds2.5 baths2,946 sq ft
43571 Bayberry Ct, Leonardtown, MD 20650
SOLD MAY 11, 2026
$579,900
D
4 beds2.5 baths3,428 sq ft
43552 Bayberry Ct, Leonardtown, MD 20650
SOLD MAY 15, 2026
$505,000
E
4 beds2.5 baths2,368 sq ft
21027 Hunting Quarter Dr, Callaway, MD 20620

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Earn from this home

Sell

$139,120

Est. take-home

List your home with Redfin and save $6,219

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,626/mo

Redfin rental estimate

List your home for rent

Market trends in 20650, MD

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.2%

+0.4% MoM

Median sale price

$566K

$126 MoM

Avg. days on market

43d

0 days MoM

Recently sold homes

6 MoM

New listings for sale

COMING SOON
$649,900
4 beds2.5 baths3,314 sq ft
22157 Monterey Pl, Leonardtown, MD 20650
(301) 862-2169
COMING SOON
$639,900
4 beds3.5 baths3,340 sq ft
23444 Lindsay Dr, Leonardtown, MD 20650
(443) 771-8009
$850,000
3 beds3 baths2,731 sq ft
19445 Blake Farms Ln, Leonardtown, MD 20650
(301) 863-2400
LISTED BY REDFIN
$435,000
4 beds2.5 baths2,624 sq ft
40717 Lake And Breton View Dr, Leonardtown, MD 20650
OPEN SEP 13, 1:30PM TO 3:30PM
$690,000
4 beds3.5 baths4,066 sq ft
21395 Fairwood Ct, Leonardtown, MD 20650
(888) 860-7369
$695,000
5 beds2.5 baths2,953 sq ft
44450 Schumann Way, Leonardtown, MD 20650
(301) 862-2169
$749,900
5 beds4 baths4,873 sq ft
41402 Omaha Ct, Leonardtown, MD 20650
(855) 450-0442
$550,000
4 beds3.5 baths2,562 sq ft
41888 Jenkins Ct, Leonardtown, MD 20650
(301) 884-9493
$780,000
5 beds4 baths5,484 sq ft
22601 Avenmar Dr, Leonardtown, MD 20650
(301) 862-2169
$600,000
4 beds3 baths3,793 sq ft
41524 Fairwood Ct, Leonardtown, MD 20650
(301) 298-2892
See all

Provided by Redfin

Redfin agents who toured

Excellent Rehab in sought after Leonardtown. First level needs drywall and flooring. Great location, private.
11 years ago• May not reflect the current state of the home
Farrah Fuchs
Redfin Premier agent

Sale history for 44403 Medleys Neck Rd

Date

Event

Price

BRIGHT MLS #MDSM2021042

Nov 18, 2024

Sold

$575,000

$217/sq ft

Oct 14, 2024

Contingent

—

Oct 11, 2024

Listed

$575,000

$217/sq ft

Oct 1, 2024

Coming Soon

$575,000

$217/sq ft

BRIGHT MLS #1001108121

Mar 11, 2016

Sold

$275,000

$104/sq ft

+14

MRIS #SM9553126

Mar 17, 2016

Delisted

—

Mar 11, 2016

Sold

$275,000

$104/sq ft

Feb 8, 2016

Pending

—

Jan 15, 2016

Listed

$104/sq ft

+14

MRIS #SM8137701

Jan 1, 2015

Delisted

—

Jul 25, 2014

Relisted

—

Apr 9, 2014

Contingent

—

Feb 7, 2014

Relisted

—

Feb 1, 2014

Delisted

—

Jan 2, 2014

Relisted

—

Jan 1, 2014

Delisted

—

Nov 14, 2013

Price Changed

Jul 19, 2013

Listed

BRIGHT MLS #1007014790

Jan 1, 2015

Listing Removed

—

Jul 19, 2013

Listed

$448,000

$169/sq ft

BRIGHT MLS #1004421410

Jul 27, 2011

Sold

$430,000

$162/sq ft

Jun 9, 2011

Listing Removed

—

May 8, 2011

Listed

$439,900

$166/sq ft

MRIS #SM7596723

Jun 10, 2011

Pending

—

May 8, 2011

Listed

$166/sq ft

Public Records

Sep 20, 1990

Sold

$45,000

$17/sq ft

Public Records

Nov 30, 1987

Sold

$20,000

$8/sq ft

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$4,830 (+15.8%)

2024

$4,172 (+3.4%)

$128,700 + $312,800

$441,500

2023

$4,034 (+3.5%)

2022

$3,898 (+2.8%)

2021

$3,793 (+2.9%)

$134,500 + $219,400

$353,900

2020

$3,686 (+2.9%)

2019

$3,581 (+1.4%)

2018

$3,531 (+3.9%)

2017

$3,397 (+5.5%)

2015

$3,220 (−11.1%)

$129,500 + $181,100

$310,600

2014

$3,621

$124,500 + $213,200

$337,700

2013

$3,622 (+101.7%)

2012

$1,796 (−50.2%)

2011

$3,606

2010

$3,606 (+21.2%)

2009

$2,975

Tax history for 44403 Medleys Neck Rd

Year

Property tax

Land + Additions

Assessment*

2025

$4,830 (+15.8%)

2024

$4,172 (+3.4%)

$128,700 + $312,800

$441,500

2023

$4,034 (+3.5%)

2022

$3,898 (+2.8%)

2021

$3,793 (+2.9%)

$134,500 + $219,400

$353,900

2020

$3,686 (+2.9%)

2019

$3,581 (+1.4%)

2018

$3,531 (+3.9%)

2017

$3,397 (+5.5%)

2015

$3,220 (−11.1%)

$129,500 + $181,100

$310,600

2014

$3,621

$124,500 + $213,200

$337,700

2013

$3,622 (+101.7%)

2012

$1,796 (−50.2%)

2011

$3,606

2010

$3,606 (+21.2%)

2009

$2,975

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning
Permits

Beds

—

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

4.91 Acres

Year renovated

—

Sq. Ft.

2,647

Year built

1992

Style

Single Family Residential

County

St. Mary's County

APN

02 026252

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 14, 2026.

RPD

Rural Preservation District

The regulations of Rural Preservation Districts are intended to foster agricultural, forestry, mineral resource extraction, and aquacultural uses and protect the land base necessary to support these activities. Low density residential development in this type of district is permitted subject to performance standards that maintain the rural character of the district in recognition of the fact that a full range of public facilities is not provided or planned. The farmer has the right to farm without being restricted by neighboring residential areas. Restricted hours of operation for farm equipment, restricted odor-producing fertilizers, or mandatory noise reductions may not be imposed on farmers in an RPD zoning district. The general intent of the district is to encourage farming without undue burden on the landowner. In accordance with these intentions, the following provisions for the protection of agricultural uses will apply: (1) Any farm use of land is permitted. (2) Operation, at any time, of machinery used in farm production or the primary processing of agricultural products is permitted. (3) Normal agricultural activities and operations in accordance with good husbandry practices, which do not cause bodily injury or directly endanger human health, are permitted and preferred activities, including activities that may produce normal agriculture related noise and odors. (4) The sale of farm products produced on the farm where the sales are made is permitted.

Permitted uses

Include but are not limited to:

Equestrian facility
Greenhouse / nursery
Livestock production
Winery & vineyard
Housing-Single unit
Manufacturing
Bed & breakfast
Agriculture-Cropland
Agriculture-Grove / orchard
Timberland

Property details

Parking

Parking Information
# of Attached Garage Spaces: 2
Garage Features: Additional Storage Area, Covered Parking, Garage Door Opener, Oversized
# of Total Garage and Parking Spaces: 4
Has Garage
# of Garage Spaces: 2
Driveway - # of Spaces: 2
Attached Garage, Driveway

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 3

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 2
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 2
# of Bathrooms (Half): 1
# of Bathrooms (Full): 2

Interior Information
Living Area Sq.Ft. Source: Assessor

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Brick, Wood

Basement Information
Basement: No

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $312,800
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Construction Materials: Concrete, Vinyl Siding
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Structure Type: Detached

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $128,700

Above Grade Information
Finished Sq.Ft.: 2,647
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
County Tax: $3,957
Tax Assessed Value: $412,300
Tax Year: 2024
Tax Annual Amount: $3,957

Assessments Information
Year Assessed: 2024

Utilities

Utilities Information
Central Air
Cooling Type: Multi Units, Heat Pump(s), Central A/C
Cooling Fuel: Electric, Other
Heat Pump(s)
Heating Fuel: Oil
Hot Water: Electric
Sewer Septic: Private Septic Tank
Water Source: Well

Location

School Information
School District Name: ST. MARYS COUNTY PUBLIC SCHOOLS
School District Source: 3rd Party

Location Information
Outside City Limits
Directions: Take Route 5 in Leonardtown to Chingville Road. Go all the way to the stop sign. Driveway is directly across from Chingville Road intersection, where Chingville Road meets Medley's Neck Road. Driveway is split. Stay to the left where it's paved.

Public facts

Beds: —
Baths: 2.5
Sq. Ft.: 2,647
Stories: 2.0
Lot Size: 4.91 acres
Style: Single Family Residential
Year Built: 1992
Year Renovated: —
County: St. Mary's County
APN: 02 026252

Home facts updated by county records on Aug 14, 2026

Around this home

Schools

Piney Point Elementary School

Public PreK-5 • Assigned • 3.9mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 5.2mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 4.9mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

9/10 Heat Factor

7 days above 101° expected this year, 17 days in 30 years

6/10 Wind Factor

41% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Leonardtown, MD • 20650

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.5 hours in June and 4.9 hours in December, which is comparable to the U.S. average for solar exposure.

9.5 hrs

4.9 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$591,000 – $716,000

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40717 Lake And Breton View Dr, Leonardtown, MD 20650

OPEN SEP 13, 1:30PM TO 3:30PM

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21395 Fairwood Ct, Leonardtown, MD 20650

(888) 860-7369

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44450 Schumann Way, Leonardtown, MD 20650

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41402 Omaha Ct, Leonardtown, MD 20650

(855) 450-0442

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4 beds3.5 baths2,562 sq ft

41888 Jenkins Ct, Leonardtown, MD 20650

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22601 Avenmar Dr, Leonardtown, MD 20650

(301) 862-2169

Home values near 44403 Medleys Neck Rd

Data from public records.

Address	Redfin Estimate
44445 Medleys Neck Road, Leonardtown, MD 3 Beds \| 2 Baths \| 2251 Sq. Ft.	$549,550
44484 Medleys Neck Road, Leonardtown, MD - Beds \| 2 Baths \| 1504 Sq. Ft.	$382,152

Address	Redfin Estimate
44495 Medleys Neck Road, Leonardtown, MD - Beds \| 2 Baths \| 1560 Sq. Ft.	$494,581
44313 Medleys Neck Road, Leonardtown, MD - Beds \| 2 Baths \| 2772 Sq. Ft.	$586,940

Address	Redfin Estimate
44450 Medleys Neck Road, Leonardtown, MD - Beds \| 1.5 Baths \| 1440 Sq. Ft.	$365,554
20280 Natures Way, Leonardtown, MD - Beds \| 3.5 Baths \| 4324 Sq. Ft.	$714,270

Property information provided by BRIGHT MLS when last listed in 2024. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 20650, MD

Redfin agents who toured

Sale history for 44403 Medleys Neck Rd

Tax history for 44403 Medleys Neck Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 20650

Home values near 44403 Medleys Neck Rd

More real estate resources