Leonardtown, MD Real Estate Listings

13 real estate listings match this search criteria near Leonardtown.

Active
75 photos
$624,900
4 bd, 3.5 ba, 3,314 Sq Ft
41462 Culpepper WayLeonardtown, MD 20650#MDSM2031988
Single Family Residence
Active
70 photos
$389,000
3 bd, 2 ba, 1,728 Sq Ft
41620 Church StreetLeonardtown, MD 20650#MDSM2030446
Single Family Residence
Active
9 photos
$454,900
4 bd, 3.5 ba, 2,554 Sq Ft
Lot 156 - 23634 Dragonfly LaneLeonardtown, MD 20650#MDSM2031220
Townhouse
Active
45 photos
$449,900
4 bd, 3.5 ba, 2,604 Sq Ft
Lot 140 - 23659 Dragonfly LaneLeonardtown, MD 20650#MDSM2031072
Townhouse
Active
61 photos
$535,000
4 bd, 3.5 ba, 2,562 Sq Ft
41888 Jenkins CourtLeonardtown, MD 20650#MDSM2033062
Single Family Residence
Active
33 photos
$590,000
4 bd, 3 ba, 3,793 Sq Ft
41524 Fairwood CourtLeonardtown, MD 20650#MDSM2033246
Single Family Residence
Active
85 photos
$620,000
5 bd, 2.5 ba, 4,836 Sq Ft
23636 Hansel CourtLeonardtown, MD 20650#MDSM2033984
Single Family Residence
Active
43 photos
$629,900
4 bd, 3.5 ba, 3,340 Sq Ft
23444 Lindsay DriveLeonardtown, MD 20650#MDSM2033554
Single Family Residence
Active
66 photos
$474,900
3 bd, 2 ba, 1,710 Sq Ft
41495 Garrett CourtLeonardtown, MD 20650#MDSM2033936
Single Family Residence
Active
42 photos
$449,900
4 bd, 3.5 ba
Lot 139 - 23665 Dragonfly LaneLeonardtown, MD 20650#MDSM2033224
Townhouse
Active
42 photos
$449,900
4 bd, 3.5 ba
Lot 143 - 23641 Dragonfly LaneLeonardtown, MD 20650#MDSM2033226
Townhouse
Active
102 photos
$650,000
4 bd, 3.5 ba, 3,344 Sq Ft
23513 Sly Fox WayLeonardtown, MD 20650#MDSM2033928
Single Family Residence
Active
53 photos
$599,900
4 bd, 3.5 ba, 2,736 Sq Ft
23354 Lindsay DriveLeonardtown, MD 20650#MDSM2033334
Single Family Residence

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 EXIT Realty 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. 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. Information Deemed Reliable But Not Guaranteed. Copyright ©2026 Bright MLS. All rights reserved.

13 real estate listings match this search criteria near Leonardtown.

Active
75 photos
$624,900
4 bd, 3.5 ba, 3,314 Sq Ft
41462 Culpepper WayLeonardtown, MD 20650#MDSM2031988
Single Family Residence
Active
70 photos
$389,000
3 bd, 2 ba, 1,728 Sq Ft
41620 Church StreetLeonardtown, MD 20650#MDSM2030446
Single Family Residence
Active
9 photos
$454,900
4 bd, 3.5 ba, 2,554 Sq Ft
Lot 156 - 23634 Dragonfly LaneLeonardtown, MD 20650#MDSM2031220
Townhouse
Active
45 photos
$449,900
4 bd, 3.5 ba, 2,604 Sq Ft
Lot 140 - 23659 Dragonfly LaneLeonardtown, MD 20650#MDSM2031072
Townhouse
Active
61 photos
$535,000
4 bd, 3.5 ba, 2,562 Sq Ft
41888 Jenkins CourtLeonardtown, MD 20650#MDSM2033062
Single Family Residence
Active
33 photos
$590,000
4 bd, 3 ba, 3,793 Sq Ft
41524 Fairwood CourtLeonardtown, MD 20650#MDSM2033246
Single Family Residence
Active
85 photos
$620,000
5 bd, 2.5 ba, 4,836 Sq Ft
23636 Hansel CourtLeonardtown, MD 20650#MDSM2033984
Single Family Residence
Active
43 photos
$629,900
4 bd, 3.5 ba, 3,340 Sq Ft
23444 Lindsay DriveLeonardtown, MD 20650#MDSM2033554
Single Family Residence
Active
66 photos
$474,900
3 bd, 2 ba, 1,710 Sq Ft
41495 Garrett CourtLeonardtown, MD 20650#MDSM2033936
Single Family Residence
Active
42 photos
$449,900
4 bd, 3.5 ba
Lot 139 - 23665 Dragonfly LaneLeonardtown, MD 20650#MDSM2033224
Townhouse
Active
42 photos
$449,900
4 bd, 3.5 ba
Lot 143 - 23641 Dragonfly LaneLeonardtown, MD 20650#MDSM2033226
Townhouse
Active
102 photos
$650,000
4 bd, 3.5 ba, 3,344 Sq Ft
23513 Sly Fox WayLeonardtown, MD 20650#MDSM2033928
Single Family Residence
Active
53 photos
$599,900
4 bd, 3.5 ba, 2,736 Sq Ft
23354 Lindsay DriveLeonardtown, MD 20650#MDSM2033334
Single Family Residence

Market Overview — Leonardtown, MD

Showing Leonardtown, MD

Property type

ResidentialCommercial

Transaction

For SaleFor Lease

Area Average

Median over the active for-sale listings

$615,000
Median Listing Price: 72
Median Days on EXIT Realty: 2,730
Median Sq Ft: $214
Median Price per Sq Ft

Compare

Compare Leonardtown, MD to another area

Median price, days on market and size comparison by area
Area	Median Listing Price	Median Days on EXIT Realty	Median Sq Ft	Median Price per Sq Ft	Actions
Leonardtown, MD	$615,000	72	2,730	$214

Market Composition

What's on the market

69%Residential57 active
16%Land13 active
11%For Lease9 active
5%Commercial Lease4 active

Active listings by price

$200K-$400K12% · 7
$400K-$600K33% · 19
$600K-$800K44% · 25
$800K-$1M4% · 2
Over $1M7% · 4

Median Price Trend

Sep 2026: $599,000 -18.6%Oct 2026: $487,400

Thinking of selling?

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Nearby Schools

Elementary 6

Father Andrew White School
Leonardtown, MD · 0.3 mi away
Leonardtown Elementary School
Leonardtown, MD · 0.4 mi away
Captain Walter Francis Duke Elementary School
Leonardtown, MD · 1.4 mi away
Benjamin Banneker Elementary
Loveville, MD · 3.4 mi away
Evergreen Elementary School
California, MD · 4.0 mi away
Hollywood Elementary School
Hollywood, MD · 6.0 mi away

Secondary 6

St Mary's Ryken High School
Leonardtown, MD · 0.8 mi away
Dr. James A. Forrest Career and Technology Center
Leonardtown, MD · 1.9 mi away
Leonardtown High School
Leonardtown, MD · 2.0 mi away
Starmaker School
California, MD · 5.2 mi away
Chopticon High School
Clements, MD · 6.0 mi away
Chopticon High School
Morganza, MD · 6.2 mi away

Other schools 8

Boundless Expectations
Leonardtown, MD · 0.2 mi away
Lhjna
Leonardtown, MD · 0.8 mi away
St. Mary's County Public Schools
Leonardtown, MD · 0.9 mi away
Board of Education of St Mry's Cnty
Loveville, MD · 3.4 mi away
MS. Hamm's First Grade Funland
Loveville, MD · 3.4 mi away
Leonardtown Middle School Annex
Loveville, MD · 3.4 mi away
Piedmont Flight Center
California, MD · 4.8 mi away
Mechanicville Mennonite School
Mechanicsville, MD · 5.1 mi away

Leonardtown, MD Real Estate Listings

Leonardtown, MD Real Estate Listings

41462 Culpepper WayLeonardtown, MD 20650#MDSM2031988

41620 Church StreetLeonardtown, MD 20650#MDSM2030446

Lot 156 - 23634 Dragonfly LaneLeonardtown, MD 20650#MDSM2031220

Lot 140 - 23659 Dragonfly LaneLeonardtown, MD 20650#MDSM2031072

41888 Jenkins CourtLeonardtown, MD 20650#MDSM2033062

41524 Fairwood CourtLeonardtown, MD 20650#MDSM2033246

23636 Hansel CourtLeonardtown, MD 20650#MDSM2033984

23444 Lindsay DriveLeonardtown, MD 20650#MDSM2033554

41495 Garrett CourtLeonardtown, MD 20650#MDSM2033936

Lot 139 - 23665 Dragonfly LaneLeonardtown, MD 20650#MDSM2033224

Lot 143 - 23641 Dragonfly LaneLeonardtown, MD 20650#MDSM2033226

23513 Sly Fox WayLeonardtown, MD 20650#MDSM2033928

23354 Lindsay DriveLeonardtown, MD 20650#MDSM2033334

41462 Culpepper WayLeonardtown, MD 20650#MDSM2031988

41620 Church StreetLeonardtown, MD 20650#MDSM2030446

Lot 156 - 23634 Dragonfly LaneLeonardtown, MD 20650#MDSM2031220

Lot 140 - 23659 Dragonfly LaneLeonardtown, MD 20650#MDSM2031072

41888 Jenkins CourtLeonardtown, MD 20650#MDSM2033062

41524 Fairwood CourtLeonardtown, MD 20650#MDSM2033246

23636 Hansel CourtLeonardtown, MD 20650#MDSM2033984

23444 Lindsay DriveLeonardtown, MD 20650#MDSM2033554

41495 Garrett CourtLeonardtown, MD 20650#MDSM2033936

Lot 139 - 23665 Dragonfly LaneLeonardtown, MD 20650#MDSM2033224

Lot 143 - 23641 Dragonfly LaneLeonardtown, MD 20650#MDSM2033226

23513 Sly Fox WayLeonardtown, MD 20650#MDSM2033928

23354 Lindsay DriveLeonardtown, MD 20650#MDSM2033334

Market Overview — Leonardtown, MD

Area Average

Compare

Market Composition

What's on the market

Active listings by price

Median Price Trend

Nearby Schools

Elementary 6

Secondary 6

Other schools 8