Leonardtown, MD - homes for sale

35 of 35 results displayed

Coming Soon
$715,000Coming Soon
5 beds 4 baths
41389 Holiday Ct, LEONARDTOWN, MD 20650
MLS# MDSM2030306Listed by: RE/MAX ONE
Open Sat, 10am to 12pm

$679,900Pending
5 beds 4 baths4,168 sq. ft.
23324 Lindsay Dr, LEONARDTOWN, MD 20650
MLS# MDSM2030244Listed by: CENTURY 21 NEW MILLENNIUM
Coming Soon
$590,000Coming Soon
5 beds 4 baths
23282 Lindsay Dr, LEONARDTOWN, MD 20650
MLS# MDSM2030258Listed by: SAMSON PROPERTIES
Coming Soon
$520,000Coming Soon
3 beds 3 baths
23207 Moakley St, LEONARDTOWN, MD 20650
MLS# MDSM2030226Listed by: RE/MAX ONE
$479,900Pending
4 beds 4 baths2,966 sq. ft.
Lot 128 - 23721 Weeping Willow Way, LEONARDTOWN, MD 20650
MLS# MDSM2029480Listed by: RE/MAX ONE
Coming Soon
$639,000Coming Soon
4 beds 4 baths
23621 Margrave Dr, LEONARDTOWN, MD 20650
MLS# MDSM2030144Listed by: EXP REALTY, LLC
$449,900Pending
4 beds 4 baths
Lot 109 - 23672 Weeping Willow Way, LEONARDTOWN, MD 20650
MLS# MDSM2030112Listed by: RE/MAX ONE
New
$449,900Active
4 beds 4 baths2,604 sq. ft.
Lot 135 - 23679 Weeping Willow Way, LEONARDTOWN, MD 20650
MLS# MDSM2030032Listed by: RE/MAX ONE
$635,000Active
4 beds 4 baths3,736 sq. ft.
23590 Margrave Dr, LEONARDTOWN, MD 20650
MLS# MDSM2030104Listed by: RE/MAX ONE
Coming Soon
$680,000Coming Soon
4 beds 3 baths
23592 Belmar Dr, LEONARDTOWN, MD 20650
MLS# MDSM2030098Listed by: RE/MAX ONE
$550,000Pending
5 beds 3 baths3,482 sq. ft.
23299 Jenifer Ct, LEONARDTOWN, MD 20650
MLS# MDSM2029912Listed by: CENTURY 21 NEW MILLENNIUM
$650,000Pending
4 beds 4 baths3,299 sq. ft.
23563 Belmar Dr, LEONARDTOWN, MD 20650
MLS# MDSM2029898Listed by: RE/MAX ONE
Coming Soon
$680,000Coming Soon
5 beds 4 baths
41488 Pensive St, LEONARDTOWN, MD 20650
MLS# MDSM2029900Listed by: RE/MAX ONE
$495,000Active
4 beds 3 baths2,507 sq. ft.
22394 White Oak Rd, LEONARDTOWN, MD 20650
MLS# MDSM2029800Listed by: KW METRO CENTER
$639,999Active
5 beds 4 baths3,724 sq. ft.
41377 Doctors Crossing Rd, LEONARDTOWN, MD 20650
MLS# MDSM2029722Listed by: KELLER WILLIAMS REALTY/LEE BEAVER & ASSOC.
$655,000Pending
5 beds 4 baths3,934 sq. ft.
41497 Affirmed Way, LEONARDTOWN, MD 20650
MLS# MDSM2029650Listed by: RE/MAX ONE
Coming Soon
$725,000Coming Soon
5 beds 2 baths
41655 Church St, LEONARDTOWN, MD 20650
MLS# MDSM2029620Listed by: TOPSIDE REALTY
$479,900Pending
4 beds 4 baths
Lot 113 - 23696 Weeping Willow Way, LEONARDTOWN, MD 20650
MLS# MDSM2029482Listed by: RE/MAX ONE
Open Sat, 1 to 4pm
$449,900Active
4 beds 4 baths
Lot 101 - 23713 Dragonfly Ln, LEONARDTOWN, MD 20650
MLS# MDSM2029486Listed by: RE/MAX ONE
Open Sat, 1 to 4pm
$449,900Active
4 beds 4 baths
Lot 99 - 23725 Dragonfly Ln, LEONARDTOWN, MD 20650
MLS# MDSM2029488Listed by: RE/MAX ONE
$437,000Pending
3 beds 4 baths2,402 sq. ft.
41516 Marwood Cir, LEONARDTOWN, MD 20650
MLS# MDSM2029470Listed by: CENTURY 21 NEW MILLENNIUM
$489,900Pending
4 beds 4 baths3,095 sq. ft.
Lot 117 - 23720 Weeping Willow Way, LEONARDTOWN, MD 20650
MLS# MDSM2029218Listed by: RE/MAX ONE
$449,900Pending
4 beds 4 baths2,571 sq. ft.
Lot 100 - 23719 Dragonfly Ln, LEONARDTOWN, MD 20650
MLS# MDSM2029208Listed by: RE/MAX ONE
$479,900Pending
4 beds 4 baths
Lot 102 - 23707 Dragonfly Ln, LEONARDTOWN, MD 20650
MLS# MDSM2029202Listed by: RE/MAX ONE
$175,000Active
6.24 Acres
St. Andrews Church Road, LEONARDTOWN, MD 20650
MLS# MDSM2029070Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
$435,000Pending
3 beds 4 baths2,308 sq. ft.
23369 Marview Ct, LEONARDTOWN, MD 20650
MLS# MDSM2028828Listed by: CENTURY 21 NEW MILLENNIUM
$599,950Pending
-- beds -- baths1,691 sq. ft.
22615 Washington St, LEONARDTOWN, MD 20650
MLS# MDSM2028632Listed by: INFINITAS REALTY GROUP
$487,400Pending
4 beds 4 baths3,095 sq. ft.
Lot 138 - 23671 Dragonfly Ln, LEONARDTOWN, MD 20650
MLS# MDSM2028534Listed by: RE/MAX ONE
$479,900Pending
4 beds 4 baths2,966 sq. ft.
Lot 137- 23667 Weeping Willow Way, LEONARDTOWN, MD 20650
MLS# MDSM2028536Listed by: RE/MAX ONE
$515,000Pending
3 beds 4 baths2,764 sq. ft.
22547 Landing Way, LEONARDTOWN, MD 20650
MLS# MDSM2029148Listed by: EXP REALTY, LLC
$635,000Pending
4 beds 3 baths2,888 sq. ft.
43018 Bluejay Ln, LEONARDTOWN, MD 20650
MLS# MDSM2027792Listed by: RE/MAX ONE
$569,000Pending
4 beds 4 baths3,308 sq. ft.
41536 Fairwood Ct, LEONARDTOWN, MD 20650
MLS# MDSM2027022Listed by: RE/MAX REALTY GROUP
$599,000Pending
3 beds 2 baths2,824 sq. ft.
23264 Lindsay Dr, LEONARDTOWN, MD 20650
MLS# MDSM2027806Listed by: RE/MAX REALTY GROUP
$1,740,000Pending
3.85 Acres
25845 Point Lookout Rd, LEONARDTOWN, MD 20650
MLS# MDSM2020046Listed by: CENTURY 21 COMMERCIAL NEW MILLENNIUM
$3,800,000Pending
52.18 Acres
Cedar Lane Rd, LEONARDTOWN, MD 20650
MLS# MDSM2019494Listed by: CENTURY 21 NEW MILLENNIUM

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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.

©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.