Leonardtown, MD

Leonardtown MD Real Estate

82Results

Leonardtown is quaint Maryland community with a vibrant history. Located about 20 mins apart, the homes for sale Leonardtown is located on beautiful, rural lots and in welcoming suburban neighborhoods. Local vineyards and farms are scattered across the rolling landscape and there are many hiking/walking trails and parks, perfect for those who enjoy an active lifestyle.

Newest
New Listing
22373 Enoch Road Leonardtown MD 20650

$3,200/month

Leonardtown, MD

22373 Enoch Road

  • 4 Beds
  • 3 Baths
  • 2,196 SqFt
  • 0 Days on Market
MLS#: MDSM2031194
Open House

$485,000

Leonardtown, MD

21807 Potomac View Drive

NEXT OPEN HOUSE:

Sat 6/6 10:00 AM to 12:00 PM

  • 4 Beds
  • 3 Baths
  • 0.48 Acres
  • 2,019 SqFt
  • 1 Day on Market
MLS#: MDSM2031452
Pending

$449,900

Leonardtown, MD

Lot 130 - 23709 Weeping Willow Way

  • 4 Beds
  • 4 Baths
  • 0.05 Acres
  • 2,571 SqFt
  • 5 Days on Market
MLS#: MDSM2031222
Pending

$449,900

Leonardtown, MD

Lot 129 - 23715 Weeping Willow Way

  • 4 Beds
  • 4 Baths
  • 0.05 Acres
  • 2,554 SqFt
  • 5 Days on Market
MLS#: MDSM2031218
Pending

$479,900

Leonardtown, MD

Lot 154 - 23808 Wisteria Lane

  • 4 Beds
  • 4 Baths
  • 0.08 Acres
  • 2,966 SqFt
  • 5 Days on Market
MLS#: MDSM2031458
Active Under Contract

$395,000

Leonardtown, MD

39944 Lady Baltimore Avenue

  • 5 Beds
  • 3 Baths
  • 0.46 Acres
  • 2,169 SqFt
  • 9 Days on Market
MLS#: MDSM2031394
Active Under Contract

$428,799

Leonardtown, MD

41600 Miss Bessie Drive

  • 3 Beds
  • 2 Baths
  • 0.36 Acres
  • 1,910 SqFt
  • 10 Days on Market
MLS#: MDSM2031384
Active Under Contract

$715,000

Leonardtown, MD

41395 Omaha Court

  • 5 Beds
  • 4 Baths
  • 0.35 Acres
  • 4,367 SqFt
  • 10 Days on Market
MLS#: MDSM2031298
Active Under Contract

$599,900

Leonardtown, MD

40704 Chance Way

  • 4 Beds
  • 3 Baths
  • 3,300 SqFt
  • 13 Days on Market
MLS#: MDSM2030700
New Listing

$449,900

Leonardtown, MD

Lot 156 - 23634 Dragonfly Lane

  • 4 Beds
  • 4 Baths
  • 0.05 Acres
  • 2,554 SqFt
  • 14 Days on Market
MLS#: MDSM2031220
New Listing

$605,000

Leonardtown, MD

43430 Browns Lane

  • 5 Beds
  • 5 Baths
  • 1.36 Acre
  • 2,756 SqFt
  • 17 Days on Market
MLS#: MDSM2031286
Pending

$2,300/month

Leonardtown, MD

41475 Bea Court

  • 3 Beds
  • 2 Baths
  • 1,710 SqFt
  • 18 Days on Market
MLS#: MDSM2031248

Maryland Homes For Sale

Search homes for sale in Mechanicsville and Leonardtown area.  Contact us if you have questions or would like to schedule a showing. You might also be interested in St. Mary's County Real Estate.

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which RE/MAX Realty Group participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated June 1, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.