Save Search

Price

Beds

Baths

Filters 1

Reset

1 Filter Applied

Basic Info

Listing Status

Purchase Type

Days On Site

Advanced

Less Than

Unit Level

City Limits Y/N

Property Details

SqFt

Switch to Acre

Lot Size

Switch to Acre

Price per Sqft

Monthly HOA Fee

Year Built

Stories

Kitchens

Flooring

Special Listing Condition

Pool

HOA Y/N

Amenities

Acceptable Financing

Level(s)

Fence

Property Sub Type

Ownership

Adult Community

Basement

Elevator

Exterior Finish

Financing

Other Rooms

Acres

Style

Water Front Y/N

Association Fee Include

Foundation

Full Bathrooms

Half Bathrooms

Minimum Lease Period

Horse Property

Frontage

Pet Allowed

Property Condition

Water Access

New Construction Y/N

Utilities

Tax Amount

Short Sale(Y/N)

Architectural Style

Sewage Type

Water

Laundry

Roof

Listing Terms

Building Type

Unit Features

Windows

Basement(Y/N)

Outbuilding

Room Type

Land Lease Fee

Fireplace Y/N

Keyword

Foreclosure Y/N

Maintenance Fee

Farm Description

Flood Zone

Assessed Value

Interior Features

Fireplace Type

Heating

Cooling

Interior Lot Features

Appliances

Fireplace Number

Exterior Features

Lot Description

Garage Type

Parking Type

Parking Space

Garage Space

Carport Spaces

Pool Y/N

Garage Y/N

Property Features

Waterfront

Community Features

Water View

Open House

Has Picture

New

Hot

Virtual Tour

3D Tour

Price Reduced

Save Search (2)

50 Properties

50 Properties Available In Leonardtown

Default

MD >Leonardtown >

Market Insights

41115 PAW PAW HOLLOW LN, Leonardtown, MD 20650

New

$775,000

41115 PAW PAW HOLLOW LN, Leonardtown, MD 20650

4 Beds6 Baths6,116 SqFt

MLS# MDSM2025074

Listed by CENTURY 21 New Millennium

23278 APPLEWOOD LN, Leonardtown, MD 20650

New

$650,000

23278 APPLEWOOD LN, Leonardtown, MD 20650

4 Beds4 Baths4,306 SqFt

MLS# MDSM2025020

Listed by EXP Realty, LLC

21549 POINT LOOKOUT, Leonardtown, MD 20650

New

$700,000

21549 POINT LOOKOUT, Leonardtown, MD 20650

5 Beds4 Baths3,153 SqFt

MLS# MDSM2024990

Listed by O'Brien Realty ERA Powered

44646 MEDLEYS NECK RD, Leonardtown, MD 20650

New

$125,000

44646 MEDLEYS NECK RD, Leonardtown, MD 20650

3 Beds1 Bath924 SqFt

MLS# MDSM2024652

Listed by Home Towne Real Estate

44114 WOODMONT DR, Leonardtown, MD 20650

Active

$615,000

44114 WOODMONT DR, Leonardtown, MD 20650

5 Beds4 Baths3,635 SqFt

MLS# MDSM2023726

Listed by RE/MAX Realty Group

Active

$5,950,000

41505 KNIGHT RD, Leonardtown, MD 20650

5 Beds8 Baths12,113 SqFt

MLS# MDSM2023270

Listed by Engel & Volkers Annapolis

40461 OLD BRETON BEACH RD, Leonardtown, MD 20650

Active

$750,000

40461 OLD BRETON BEACH RD, Leonardtown, MD 20650

3 Beds3 Baths2,040 SqFt

MLS# MDSM2023928

Listed by RE/MAX One

22626 CHICKADEE LN, Leonardtown, MD 20650

Active

$649,900

22626 CHICKADEE LN, Leonardtown, MD 20650

4 Beds4 Baths2,948 SqFt

MLS# MDSM2024686

Listed by JPAR Real Estate Professionals

41430 WHIMSICAL CT, Leonardtown, MD 20650

Active

$649,999

41430 WHIMSICAL CT, Leonardtown, MD 20650

5 Beds4 Baths3,907 SqFt

MLS# MDSM2023560

Listed by Realty Navigator

Price Dropped by $15K

$634,900

23275 JENIFER CT, Leonardtown, MD 20650

5 Beds5 Baths6,311 SqFt

MLS# MDSM2023552

Listed by CENTURY 21 New Millennium

Active

$699,900

18937 HODGES LN, Leonardtown, MD 20650

3 Beds2 Baths1,834 SqFt

MLS# MDSM2023654

Listed by CENTURY 21 New Millennium

41402 SILVER CHARM CT, Leonardtown, MD 20650

Price Dropped by $10K

$655,000

41402 SILVER CHARM CT, Leonardtown, MD 20650

5 Beds4 Baths4,046 SqFt

MLS# MDSM2023568

Listed by CENTURY 21 New Millennium

Price Dropped by $6K

$419,500

23730 HICKS DR, Leonardtown, MD 20650

3 Beds2 Baths1,992 SqFt

MLS# MDSM2023542

Listed by EXP Realty, LLC

23266 CLARKS REST RD, Leonardtown, MD 20650

Price Dropped by $10K

$665,000

23266 CLARKS REST RD, Leonardtown, MD 20650

4 Beds4 Baths3,858 SqFt

MLS# MDSM2022494

Listed by CENTURY 21 New Millennium

Price Dropped by $24K

$624,900

21897 FAIRWAY DR, Leonardtown, MD 20650

5 Beds3 Baths3,664 SqFt

MLS# MDSM2022878

Listed by Infinitas Realty Group

Price Dropped by $10K

$659,000

23534 BELMAR DR, Leonardtown, MD 20650

5 Beds4 Baths4,738 SqFt

MLS# MDSM2022692

Listed by CENTURY 21 New Millennium

41536 FAIRWOOD CT, Leonardtown, MD 20650

Price Dropped by $12K

$637,000

41536 FAIRWOOD CT, Leonardtown, MD 20650

4 Beds4 Baths3,080 SqFt

MLS# MDSM2022852

Listed by CENTURY 21 New Millennium

Price Dropped by $10K

$625,000

23348 LINDSAY DR, Leonardtown, MD 20650

5 Beds4 Baths3,540 SqFt

MLS# MDSM2022602

Listed by Fairfax Realty Premier

22362 ARMSTRONG DR, Leonardtown, MD 20650

Price Dropped by $5K

$444,900

22362 ARMSTRONG DR, Leonardtown, MD 20650

3 Beds3 Baths2,028 SqFt

MLS# MDSM2023036

Listed by CENTURY 21 New Millennium

20798 WATERSIDE DR, Leonardtown, MD 20650

Active

$450,000

20798 WATERSIDE DR, Leonardtown, MD 20650

2 Beds1 Bath1,018 SqFt

MLS# MDSM2022922

Listed by RE/MAX Closers

19700 MULBERRY FIELDS RD, Leonardtown, MD 20650

Active

$20,000,000

19700 MULBERRY FIELDS RD, Leonardtown, MD 20650

6 Beds5 Baths13,458 SqFt

MLS# MDSM2022614

Listed by Long & Foster Real Estate, Inc.

Price Dropped by $35K

$340,000

20959 REDGATE LN, Leonardtown, MD 20650

3 Beds1 Bath1,026 SqFt

MLS# MDSM2022416

Listed by Keller Williams Legacy

23773 MEREDITH CT, Leonardtown, MD 20650

Price Dropped by $40K

$699,900

23773 MEREDITH CT, Leonardtown, MD 20650

3 Beds3 Baths3,478 SqFt

MLS# MDSM2022554

Listed by Coldwell Banker Jay Lilly Real Estate

25365 POINT LOOKOUT RD, Leonardtown, MD 20650

Price Dropped by $37K

$497,500

25365 POINT LOOKOUT RD, Leonardtown, MD 20650

3 Beds3 Baths2,952 SqFt

MLS# MDSM2022468

Listed by CENTURY 21 New Millennium

explore listings in Leonardtown

Save Snapshot

View Results

MARKET SNAPSHOT

(APR 28, 2025 - MAY 28, 2025)

?

Sold Listings
?

Average Sales Price
?

Average Days on Market

LISTINGS

$1,244,999

7 Beds3 Baths2,697 SqFt

6 Timothy Ave, Everett, MA 02149

Listed by Tek Yadav of oNest Real Estate
$2,300

2 Beds1 Bath1,100 SqFt

65 Concord Ave #2, Norwood, MA 02062

Listed by Maheshwar Pant of oNest Real Estate
$675,000

7 Beds2 Baths2,171 SqFt

25 Franklin St, Lynn, MA 01902

Listed by Suman Mahara of oNest Real Estate
$1,870,000

6 Beds3.5 Baths3,754 SqFt

6 Garfield St, Lexington, MA 02421

Listed by Jason Jeon of Compass