NEW 2 HRS AGO

For sale

$79,900

Est. $557/mo —

—

•

— ba

•

1,542

sq ft

21944 Point Lookout Rd, Leonardtown, MD 20650

About this home

RARE LEONARDTOWN INVESTMENT OPPORTUNITY ON 1.54 ACRES Bring your vision and unlock the incredible potential of this rare 1.54-acre property in one of Southern Maryland's most sought-after locations. The existing home sustained fire damage and is being sold as-is, presenting a unique opportunity for investors, builders, contractors, or buyers looking for the perfect place to renovate or build their dream home. Large parcels this close to the heart of Leonardtown are becoming increasingly difficult to find. With over an acre and a half of land, mature trees, and plenty of space for privacy, the possibilities are endless. Whether you choose to restore the existing home or start fresh, this property offers an exceptional canvas in a location where demand continues to grow. Just minutes from the charming streets of historic downtown Leonardtown, you'll enjoy locally owned restaurants, coffee shops, boutiques, wineries, breweries, waterfront parks, live music, festivals, and the scenic Leonardtown Wharf overlooking Breton Bay. Outdoor enthusiasts will appreciate nearby boating, fishing, kayaking, and hiking, while commuters will love the convenient access to NAS Patuxent River, MedStar St. Mary's Hospital, and the many employers throughout Southern Maryland. Properties with this combination of acreage, location, and investment potential rarely come to market. Whether you're looking for your next renovation project, a custom homesite, or a long-term investment in one of Southern Maryland's fastest-growing and most desirable communities, this is an opportunity you won't want to miss. Bring your imagination and transform this property into something truly exceptional. Seller prefers to use Interstate Title.

Single-familyProperty Type

1930Year Built

1.54 acresLot Size

$52Price/Sq.Ft.

Listed by Mark Frisco Jr. • CENTURY 21 New Millennium

•443-968-9595 (broker)

•tommy.higgins@c21nm.com (broker)

Listing updated: Oct 23, 2026 at 07:03pm

Redfin checked: a minute ago

•Source:BRIGHT MLS #MDSM2032976

Payment calculator

$557 per month

Principal and interest$436

Property taxes

$97

HOA dues

Home insurance

$24

Utilities

Add

5 minutes to get started. No credit impact.

Affordability tools

See this home in person

We'll connect you with a local agent to show you this home, answer your questions, and assist you on your buying journey.

Next available tour time: Tomorrow

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN SAT, 11AM TO 2PM
$384,900
3 beds2.5 baths1,677 sq ft
194 Seagull Ct, Montross, VA 22520
(540) 775-5661
OPEN SAT, 11AM TO 1PM
$550,000
5 beds3.5 baths3,033 sq ft
45962 Blue Jay Ct, Great Mills, MD 20634
(301) 298-2892
OPEN SAT, 11AM TO 1PM
$379,900
3 beds2 baths2,080 sq ft
426 Seagull Ln, Lusby, MD 20657
(410) 535-5050
OPEN SAT, 12PM TO 1:30PM3D WALKTHROUGH
$205,000
2 beds2 baths1,174 sq ft
45482 Westmeath Way Unit H 14, Great Mills, MD 20634
(301) 870-7653
OPEN SAT, 12PM TO 2PM
$375,000
3 beds2.5 baths1,768 sq ft
12162 Catalina Dr, Lusby, MD 20657
(571) 386-1075
OPEN SAT, 1PM TO 3PM
$386,900
3 beds3 baths2,756 sq ft
11640 Mesa Trl, Lusby, MD 20657
(443) 256-3773
OPEN SAT, 1PM TO 3PM
$375,000
3 beds3.5 baths2,165 sq ft
23383 Thuja Ln, California, MD 20619
(410) 535-6291
OPEN SAT, 1PM TO 3PM
$440,000
3 beds3.5 baths2,379 sq ft
41608 Briarwood Cir, Leonardtown, MD 20650
(301) 298-2892
OPEN SUN, 10AM TO 1PM
$559,000
5 beds4.5 baths4,145 sq ft
23423 Canna Ct, California, MD 20619
(301) 862-2169
REDFIN OPEN SUN, 12PM TO 2PM3D WALKTHROUGH
$549,000
4 beds2.5 baths3,418 sq ft
2025 Dasher Dr, Lusby, MD 20657

Around this home

Schools

K - 12
Preschool & daycare

Piney Point Elementary School

Public PreK-5 • Assigned • 5.2mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 3.7mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 3.4mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

21944 Point Lookout Rd · $79,900

DAYS ON MARKET

The average home goes pending in 42 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

LIST PRICE

Median sale price in this area is $459,799. (475% higher than this home)

PRICE DROP

23% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Interior features
Fireplace

Sale and tax history for 21944 Point Lookout Rd

Sale History
Tax History

Date

Event

Price

BRIGHT MLS #MDSM2032976

Oct 23, 2026

Listed

$79,900

$52/sq ft

Public Records

Jul 28, 2022

Sold

$252,000

$163/sq ft

BRIGHT MLS #MDSM2006640

Jun 15, 2022

Sold

$252,000

$163/sq ft

May 26, 2022

Relisted

—

Apr 25, 2022

Pending

—

Apr 25, 2022

Listing Removed

—

Apr 22, 2022

Listed

$249,900

$162/sq ft

+39

1930's Cape Cod on 1.5 acres located in Leonardtown. Roof replaced in 2019, New septic system installed in 2020 and updated electric panel in 2020. Eat in kitchen with large bay window, first floor primary bedroom and bathroom, formal dining room with built in corner cabinet, and large living room with wood burning stove and beautiful heart of pine floors. 3 additional bedrooms upstairs along with a full bathroom and loft area. Screened in porch overlooking the patio area with fire pit is just off the kitchen. Home is being sold AS IS.

Public Records

Oct 8, 2014

Sold

$160,000

$104/sq ft

MRIS #SM8362167

Oct 1, 2014

Delisted

—

Sep 30, 2014

Sold

$160,000

$104/sq ft

Jun 27, 2014

Pending

—

Jun 27, 2014

Price Changed

$107/sq ft

May 30, 2014

Listed

$117/sq ft

BRIGHT MLS #1003026892

Sep 30, 2014

Sold

$160,000

$104/sq ft

Jul 9, 2014

Listing Removed

—

May 29, 2014

Listed

$164,900

$107/sq ft

BRIGHT MLS #1009802516

Sep 17, 2013

Listing Removed

—

Apr 26, 2013

Listed

$349,900

$227/sq ft

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$1,369 (−41.8%)

2024

$2,350 (+3.6%)

$112,600 + $8,900

$121,500

2023

$2,269 (+15.1%)

2022

$1,971 (+1.1%)

2021

$1,949 (+1.1%)

$118,400 + $53,100

$171,500

2020

$1,928 (+1.1%)

2019

$1,906

2018

$1,904 (+2.9%)

$113,400 + $52,500

$165,900

2017

$1,850 (+7.5%)

$113,400 + $52,500

$165,900

2015

$1,721 (−9.7%)

$114,300 + $53,300

$167,600

2014

$1,905

$109,300 + $62,900

$172,200

2013

$1,906 (+1.2%)

2012

$1,883 (−8.3%)

2011

$2,053

2010

$2,053 (+24.6%)

2009

$1,647

Public record

Public record
Zoning
Permits

Beds

—

Baths

Stories

1.5

Lot width

—

Lot depth

—

Lot size

1.54 Acres

Year renovated

—

Finished Sq. Ft.

1,542

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,542

Year built

1930

Style

Single Family Residential

County

St. Mary's County

APN

02 002604

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 16, 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

Jul 28, 2025 • Final

Residential accessory structure renov

Renovate the property and connect to the existing septic system. Work also includes parking improvements.

ADU

Plumbing

Jul 22, 2021 • Final

Electrical

Install a new electrical circuit for a sewage system.

Electrical

Plumbing

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

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

52% chance of strong winds in next 30 years

2/10 Air Factor

0 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

93/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.1 hrs

6.6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 21944 Point Lookout Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $293,000 and $599,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $293K to $599K.

SOLD APR 30, 2026
$365,000 Last sold price
3 beds2 baths1,644 sq ft
44731 Blake Creek Rd, Leonardtown, MD 20650
$170/sq ft
46 years newer
SOLD APR 15, 2026
$340,000 Last sold price
2 beds2 baths1,056 sq ft
23311 Point Lookout Rd, Leonardtown, MD 20650
$270/sq ft
smaller lot
65 years newer
SOLD SEP 23, 2026
$390,000 Last sold price
3 beds2 baths1,456 sq ft
22508 Old Rolling Rd, California, MD 20619
$216/sq ft
smaller lot
35 years newer
SOLD MAR 31, 2026
21982 Brigantine Ct, Great Mills, MD 20634
$293,000 Last sold price
3 beds2.5 baths1,526 sq ft
21982 Brigantine Ct, Great Mills, MD 20634
$140/sq ft
smaller lot
66 years newer
SOLD SEP 29, 2026
$599,000 Last sold price
3 beds2 baths1,415 sq ft
42065 White Point Beach Rd, Leonardtown, MD 20650
$371/sq ft
smaller lot
SOLD AUG 14, 2026
$349,990 Last sold price
3 beds2 baths1,440 sq ft
22518 Garrison Dr, California, MD 20619
$191/sq ft
smaller lot
38 years newer

Tour for free, no strings attached

Instant answers, or connect with a local agent

Start an offer

Early Access listings

EARLY ACCESSCOMPASS COMING SOON

$665,000

3 beds2 baths1,344 sq ft

6815 Westlawn Dr, Falls Church, VA 22042

EARLY ACCESSCOMPASS COMING SOON

$1,295,000

5 beds4 baths3,467 sq ft

21901 New Hampshire Ave, Brookeville, MD 20833

EARLY ACCESSCOMPASS COMING SOON

$1,500,000

4 beds3 baths3,116 sq ft

5415 22nd St N, Arlington, VA 22205

EARLY ACCESSCOMPASS COMING SOON

$1,595,000

7 beds4 baths3,810 sq ft

4422 Q St NW, Washington, DC 20007

EARLY ACCESSREDFIN COMING SOON

$689,000

3 beds2.5 baths1,851 sq ft

1232 Sharon Acres Rd, Forest Hill, MD 21050

EARLY ACCESSREDFIN OPEN NOV 8, 1PM TO 3PM

$395,000

3 beds3.5 baths1,892 sq ft

133 Streamview Dr, Fredericksburg, VA 22405

Nearby similar homes

$929,900

4 beds3.5 baths4,248 sq ft

20945 Greenwell Way, Leonardtown, MD 20650

(301) 863-2400

OPEN OCT 31, 11AM TO 3PM

$1,050,000

3 beds2.5 baths5,939 sq ft

20098 Piney Point Rd, Callaway, MD 20620

(240) 724-6550

$299,995

3 beds1.5 baths960 sq ft

21514 Forest Run Dr, Lexington Park, MD 20653

(410) 429-7425

$680,000

4 beds3.5 baths4,066 sq ft

21395 Fairwood Ct, Leonardtown, MD 20650

(888) 860-7369

$325,000

3 beds1 bath1,040 sq ft

44911 Buck Redman Rd, Callaway, MD 20620

(301) 645-1700

NEW CONSTRUCTION

$776,220

4 beds3.5 baths2,253 sq ft

19166 N Porto Bello Dr, Drayden, MD 20630

(443) 771-8009

New listings for sale in 20650

LISTED BY REDFIN3D WALKTHROUGH

$489,900

3 beds2.5 baths1,976 sq ft

22301 White Oak Rd, Leonardtown, MD 20650

NEW 2 HRS AGO

$79,900

— beds— baths1,542 sq ft

21944 Point Lookout Rd, Leonardtown, MD 20650

(443) 968-9595

COMING SOON

$467,000

3 beds2.5 baths1,568 sq ft

22630 Quiet Ln, Leonardtown, MD 20650

(301) 884-9493

COMING SOON

$2,200,000

4 beds3 baths4,395 sq ft

22395 Newtowne Neck Rd, Leonardtown, MD 20650

(443) 975-7555

$650,000

4 beds3.5 baths3,264 sq ft

41427 Osborne Ln, Leonardtown, MD 20650

(443) 771-8009

OPEN SAT, 1PM TO 3PM

$440,000

3 beds3.5 baths2,379 sq ft

41608 Briarwood Cir, Leonardtown, MD 20650

(301) 298-2892

COMING SOON

$685,000

5 beds3.5 baths4,271 sq ft

23603 Margrave Dr, Leonardtown, MD 20650

(888) 860-7369

$590,000

4 beds4 baths3,750 sq ft

22220 Bull Rd, Leonardtown, MD 20650

(301) 855-8600

$299,500

3 beds1.5 baths1,218 sq ft

42163 Blacksmith Shop Rd, Leonardtown, MD 20650

(301) 862-2169

Details provided by BRIGHT MLS and may not match the public record. Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Leonardtown	Agents near me	Frederick, MD homes for sale	Leonardtown Housing Market
Houses for sale near me	Baltimore, MD homes for sale	Rockville, MD homes for sale
Land for sale near me	Bethesda, MD homes for sale	Columbia, MD homes for sale
Open Houses near me	Bowie, MD homes for sale	Leonardtown Property Records
Condos for sale near me	Silver Spring, MD homes for sale	MD New Listings

20650 homes for sale
20627 homes for sale
20636 homes for sale

Lusby homes for sale
Mechanicsville homes for sale
Colonial Beach homes for sale

About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Lifestyle

Market insights

Property details

Sale and tax history for 21944 Point Lookout Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 21944 Point Lookout Rd

Early Access listings

Nearby similar homes

New listings for sale in 20650

More real estate resources