Movoto Real Estate

Leonardtown High School Zone Homes For Sale | Page 3

214 Homes
 
42163 Blacksmith Shop Rd, Leonardtown, MD 20650
  • $299,500
  • 3Bd
  • 2Ba
  • 1,218 Sq Ft
43410 Old Wharf Ln, Hollywood, MD 20636
  • $1,299,000
  • 4Bd
  • 3Ba
  • 2,748 Sq Ft
$51K
25397 Allston Ln, Hollywood, MD 20636
  • $434,900
  • 3Bd
  • 2Ba
  • 1,497 Sq Ft
$10K
41462 Culpepper Way, Leonardtown, MD 20650
  • $624,900
  • 4Bd
  • 4Ba
  • 3,314 Sq Ft
$10.1K
24715 Half Pone Point Rd, Hollywood, MD 20636
  • $1,450,000
  • 1Bd
  • 1Ba
  • 1,000 Sq Ft
24730 Half Pone Point Rd, Hollywood, MD 20636
  • $4,595,000
  • 4Bd
  • 7Ba
  • 13,665 Sq Ft
19335 Greens Crossing Ct, Great Mills, MD 20634
  • $569,900
  • 4Bd
  • 4Ba
  • 3,436 Sq Ft
$15.1K
lot7 42084 Wildflower Dr, Leonardtown, MD 20650
  • $629,900
  • 4Bd
  • 3Ba
  • 3,072 Sq Ft
Parcel 323 Tract 2 Washington Street, Leonardtown, MD 20650
  • $399,000
  • 0.25 Acre
24301 Old Hollywood Rd, Hollywood, MD 20636
  • $459,900
  • 3Bd
  • 2Ba
  • 2,365 Sq Ft
$15.1K
44911 Buck Redman Rd, Callaway, MD 20620
  • $325,000
  • 3Bd
  • 1Ba
  • 1,040 Sq Ft
45025 Nolan Ct, Hollywood, MD 20636
  • $149,900
  • 0.81 Acre
Whirlwind Road, Leonardtown, MD 20650
  • $279,000
  • 23.44 Acre
$9.9K
20275 Jackson Rd, Callaway, MD 20620
  • $250,000
  • 2Bd
  • 2Ba
  • 924 Sq Ft
Ewell Lane, Hollywood, MD 20636
  • $175,000
  • 3.16 Acre
23423 Canna Ct, California, MD 20619
  • $569,000
  • 5Bd
  • 5Ba
  • 4,145 Sq Ft
$10K
42700 Moll Dyer Rd, Leonardtown, MD 20650
  • $240,000
  • 15 Acre
$50K
23955 Hollywood Rd, Hollywood, MD 20636
  • $275,000
  • 3Bd
  • 2Ba
  • 1,192 Sq Ft
$25K
lot156 23634 Dragonfly Ln, Leonardtown, MD 20650
  • $454,900
  • 4Bd
  • 4Ba
  • 2,554 Sq Ft
Open SUN 11-3
Cottonwood Parkway, California, MD 20619
  • $775,000
  • 4.7 Acre
20098 Piney Point Rd, Callaway, MD 20620
  • $1,100,000
  • 3Bd
  • 3Ba
  • 5,939 Sq Ft
lot140 23659 Dragonfly Ln, Leonardtown, MD 20650
  • $454,900
  • 4Bd
  • 4Ba
  • 2,604 Sq Ft
Open SUN 11-3
Cottonwood Parkway, California, MD 20619
  • $16,000,000
  • 141.46 Acre
$6M
25675 Southwell Ln, Hollywood, MD 20636
  • $100,000
  • 2.17 Acre
$15K
16104 Piney Point Rd, Piney Point, MD 20674
  • $620,000
  • 5Bd
  • 2Ba
  • 1,440 Sq Ft
$29.9K
42249 Saint Johns Rd, Leonardtown, MD 20650
  • $364,900
  • 3Bd
  • 2Ba
  • 1,161 Sq Ft
$10K
41708 Fenwick St, Leonardtown, MD 20650
  • $300,000
  • 1.51 Acre
41620 Church St, Leonardtown, MD 20650
  • $389,000
  • 3Bd
  • 2Ba
  • 1,728 Sq Ft
$10K
44405 5 Lots K R Way, Hollywood, MD 20636
  • $1,300,000
  • 3.69 Acre
24040 Hollywood Rd, Hollywood, MD 20636
  • $320,000
  • 3Bd
  • 1Ba
  • 1,000 Sq Ft
$15K
18832 Piney Point Rd, Valley Lee, MD 20692
  • $79,900
  • 3.57 Acre
20798 Waterside Dr, Leonardtown, MD 20650
  • $450,000
  • 2Bd
  • 1Ba
  • 1,018 Sq Ft
$50K
17377 Piney Point Rd, Piney Point, MD 20674
  • $99,000
  • 0.52 Acre
Holly Street, Piney Point, MD 20674
  • $60,000
  • 0.28 Acre
44029 Fieldstone Way, California, MD 20619
  • $299,000
  • 2Bd
  • 2Ba
  • 1,381 Sq Ft
$11K
St. Andrews Church Road, Leonardtown, MD 20650
  • $175,000
  • 6.24 Acre
20265 Hawks Way, Leonardtown, MD 20650
  • $149,900
  • 1.44 Acre
Piney Point Road, Callaway, MD 20620
  • $85,000
  • 1.5 Acre
$10K
Saint Johns Road, Hollywood, MD 20636
  • $200,000
  • 1.2 Acre
$25K
19163 Porto Bello, Drayden, MD 20630
  • $599,900
  • 4Bd
  • 3Ba
  • 2,343 Sq Ft
46234 Stasha, Drayden, MD 20630
  • $679,900
  • 4Bd
  • 3Ba
  • 2,643 Sq Ft
24984 Sotterley Rd, Hollywood, MD 20636
  • $125,000
  • 1.19 Acre
Saint Georges Park Road, Piney Point, MD 20674
  • $35,000
  • 0.25 Acre
Saint Georges Park Road, Piney Point, MD 20674
  • $45,000
  • 0.38 Acre
19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • $15,000,000
  • 6Bd
  • 5Ba
  • 5,500 Sq Ft
$5M
23794 23790 Saint Clair Rd, California, MD 20619
  • $1,070,000
  • 6Bd
  • 6Ba
  • 3,170 Sq Ft
$30K
24250 N Patuxent Beach Rd, California, MD 20619
  • $100,000
  • 0.23 Acre
$10K
26188 Skyview Dr, Hollywood, MD 20636
  • $399,000
  • 3Bd
  • 2Ba
  • 2,150 Sq Ft
$100K
46175 Greens Rst, Great Mills, MD 20634
  • $249,700
  • 1.63 Acre
$20K
45252 Happyland Rd, Valley Lee, MD 20692
  • $150,000
  • 1.75 Acre
101 - 150 of 214 Homes for sale in Leonardtown, MD
1 2 3 4 5
By entering my info and clicking Submit below, I am providing my e-signature and express written consent to receive marketing emails, calls, and texts (including via automatic telephone dialing systems, AI generative, artificial or pre-recorded voice technology) relating to my inquiry from Movoto (and parties calling/messaging on their behalf) even if my number appears on the company, state, or national Do Not Call Registry. You also agree to ourTerms and Conditions and Privacy Policy. Consent not required to receive services (call 1-844-420-1270 to be connected without providing consent).

Explore nearby locations

The prices shown are the median list prices.

Narrow your search

Leonardtown, MD real estate market trends

Statistics as of October 2026
$560K
Avg. list price
$200/Sqft
Avg. price/sqft
75
Homes for sale
2,730 Sqft
Avg. home size
66 Days
Avg. days on market
Movoto makes it easy to track market trends in Leonardtown, MD. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Leonardtown, MD?
Schools
Leonardtown, MD Schools. Ratings provided by great school See all…

Frequently Asked Questions about Leonardtown, MD

Meet with a real estate agent today (844) 417-0593
  • Movoto Logo
  • Download IOS APP Download Android APP
The multiple listing information is provided by BRIGHT MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Buyer to verify all information. The information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing information updated every 15 minutes. Terms of use & Privacy Policy, California Privacy Info. Copyright © 2005 - 2026 Movoto, Inc. All rights reserved. Equal Housing Opportunity CalDRE CalDRE #01517281
Movoto Real Estate is committed to ensuring accessibility for individuals with disabilities. We are continuously working to improve the accessibility of our web experience for everyone. We welcome feedback and accommodation requests, please submit them here.
© 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 Movoto 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: 10/6/2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closedor are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHTMLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually solddue to reporting errors.
Requests for information regarding mortgage products will be directed to Movoto.com affiliate, Lower, LLC - a licensed Mortgage Lender (NMLS #1124061), or, based on your location, may be redirected to a participating mortgage marketing partner that may pay Lower, LLC for any consumer contact information provided through this site.