View Lot 158 - 23646 Dragonfly Lane Leonardtown, MD MLS# MDSM2031014
  • New Construction with Virtual Tour
1 of 34
$449,900
4

Beds

3.1

Baths

2,554

Sq.Ft.

Lot 158 - 23646 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 131 - 23703 Weeping Willow Way Way Leonardtown, MD MLS# MDSM2031070
  • New Construction with Virtual Tour
1 of 34
$449,900
4

Beds

3.1

Baths

2,554

Sq.Ft.

Lot 131 - 23703 Weeping Willow Way Way

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 140 - 23659 Dragonfly Lane Leonardtown, MD MLS# MDSM2031072
  • Recently Listed with Virtual Tour
1 of 45
$449,900
4

Beds

3.1

Baths

2,604

Sq.Ft.

Lot 140 - 23659 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
The time to sell is now! THE TIME TO SELL IS NOW!
View Lot 156 - 23634 Dragonfly Lane Leonardtown, MD MLS# MDSM2031220
  • Recently Listed with Virtual Tour
1 of 7
$449,900
4

Beds

3.1

Baths

2,554

Sq.Ft.

Lot 156 - 23634 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 40295 Busy Corner Road Leonardtown, MD MLS# MDSM2030516
$439,900
4

Beds

3.0

Baths

1,624

Sq.Ft.

40295 Busy Corner Road

Leonardtown, MD

Bright
Courtesy of HOME TOWNE REAL ESTATE
View 41600 Miss Bessie Drive Leonardtown, MD MLS# MDSM2031384
  • Recently Listed with Virtual Tour
1 of 33
OPEN HOUSE: Saturday 5/23 1:00 PM - 4:00 PM
$428,799
3

Beds

2.0

Baths

1,910

Sq.Ft.

41600 Miss Bessie Drive

Leonardtown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 41620 Church Street Leonardtown, MD MLS# MDSM2030446
$399,000
3

Beds

2.0

Baths

1,728

Sq.Ft.

41620 Church Street

Leonardtown, MD

Bright
Courtesy of EVERGREEN PROPERTIES
View 39944 Lady Baltimore Avenue Leonardtown, MD MLS# MDSM2031394
$395,000
5

Beds

2.1

Baths

2,169

Sq.Ft.

39944 Lady Baltimore Avenue

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 21983 Point Lookout Road Leonardtown, MD MLS# MDSM2031060
$389,900
3

Beds

2.0

Baths

1,144

Sq.Ft.

21983 Point Lookout Road

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 22281 Nomoni Street Leonardtown, MD MLS# MDSM2030234
$355,000
3

Beds

2.0

Baths

1,152

Sq.Ft.

22281 Nomoni Street

Leonardtown, MD

Bright
Courtesy of COLDWELL BANKER PREMIER
View 22381 Cedar Street Leonardtown, MD MLS# MDSM2031080
$329,900
3

Beds

2.0

Baths

1,287

Sq.Ft.

22381 Cedar Street

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 22175 Bayside Road Leonardtown, MD MLS# MDSM2029056
$315,000
2

Beds

2.0

Baths

1,192

Sq.Ft.

22175 Bayside Road

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 41708 Fenwick Street Leonardtown, MD MLS# MDSM2030598
$300,000
Studio

Beds

0.0

Baths

41708 Fenwick Street

Leonardtown, MD

Bright
Courtesy of REDFIN CORP
View 43488 Medleys Neck Road Leonardtown, MD MLS# MDSM2027738
$190,000
Studio

Beds

0.0

Baths

43488 Medleys Neck Road

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 24645 Springhill Lane Leonardtown, MD MLS# MDSM2009842
$175,000
Studio

Beds

0.0

Baths

24645 Springhill Lane

Leonardtown, MD

Bright
Courtesy of GREENMARK REAL ESTATE
View 22501 Bull Road Leonardtown, MD MLS# MDSM2009850
$175,000
Studio

Beds

0.0

Baths

22501 Bull Road

Leonardtown, MD

Bright
Courtesy of GREENMARK REAL ESTATE
View St. Andrews Church Road Leonardtown, MD MLS# MDSM2029070
$175,000
Studio

Beds

0.0

Baths

St. Andrews Church Road

Leonardtown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View 20265 Hawks Way Leonardtown, MD MLS# MDSM2028774
$149,900
Studio

Beds

0.0

Baths

20265 Hawks Way

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 19921 Tower Hill Road Leonardtown, MD MLS# MDSM2026598
$130,000
Studio

Beds

0.0

Baths

19921 Tower Hill Road

Leonardtown, MD

Bright
Courtesy of RE/MAX REALTY GROUP
View 40412 B Somerville Lane Leonardtown, MD MLS# MDSM2027980
$99,000
Studio

Beds

0.0

Baths

40412 B Somerville Lane

Leonardtown, MD

Bright
Courtesy of TOPSIDE REALTY

About Leonardtown

Listings in Leonardtown, MD

92

Estimated median home price

$489,900
Leonardtown MD Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Leonardtown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Leonardtown, MD.

Homes for Sale by Price in Leonardtown, MD

PriceCount
$0 - 100K3
$100K - 200K6
$200K - 300K1
$300K - 400K6
$400K - 500K32
$500K - 600K12
$600K - 700K14
$700K - 800K9
$800K - 900K3
$900K - 1M1
$1M - Max5

Homes for Sale by Type in Leonardtown, MD

Property TypeCount
Single Family53
Townhouse24
Condo0
Commercial1
Rental18
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 5/23/2026)

Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

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 sold or are no longer being offered for sale.

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