$650,000
$30K PRICE DROP
Under Contract
- 2 Beds
- 2.5 Baths
- 2,040 Sq Ft
40461 Old Breton Beach Rd, Leonardtown, MD 20650
Billy Rabbitt
The Southside Group Real Estate
6,994
Homes in ZIP Code 20650
-
40461 Old Breton Beach Rd, Leonardtown, MD 20650
-
$3,075 Per Month
- 3 Beds
- 2.5 Baths
- 2,140 Sq Ft
- House for Rent
23650 Coventry Dr, Leonardtown, MD 20650
23650 Coventry Dr, Leonardtown, MD 20650 -
$655,000
Sold Apr 24, 202641497 Affirmed Way, Leonardtown, MD 20650
- 5 Beds
- 3.5 Baths
- 3,934 Sq Ft
- Built 2008
Last Sold Summary
- $166/SF
- 2 Days On Market
Current Estimated Value $653,952
Last Listing Agent Heather Foster RE/MAX One
41497 Affirmed Way, Leonardtown, MD 20650 -
Est $542,698
Not Listed For Sale41412 Doctors Crossing Rd, Leonardtown, MD 20650
- 4 Beds
- 3.5 Baths
- 2,686 Sq Ft
- Built 2019
Last Sold Summary
- 67 Days On Market
Last Listing Agent Delaney Clarke RE/MAX United Real Estate
-
$635,000
$15K PRICE DROP- 5 Beds
- 2.5 Baths
- 2,601 Sq Ft
40751 Merlin Way, Leonardtown, MD 20650
40751 Merlin Way, Leonardtown, MD 20650
Tracy Trammell
Metro City Realty
-
Starting at $2,275 Per Month
- 2 - 3 Beds
44980 Hamptons Blvd, Leonardtown, MD 20650
44980 Hamptons Blvd, Leonardtown, MD 20650The Newest Apartment Community Serving Pax River. Luxury apartment homes in Leonardtown, MD. A Gated Community within walking distance to the town square, which features many restaurants, shops, entertainment venues and the Wharf Waterfront. Short drive to NAVAIR - Pax River Naval Air Station. 2 and 3 bedroom apartments...all with 2 bathrooms, gourmet kitchens, FREE CLIMATE CONTROLLED STORAGE
The Hamptons at Leonardtown
-
$633,000
Sold Sep 19, 202522272 Orchard Ct, Leonardtown, MD 20650
- 4 Beds
- 3.5 Baths
- 3,745 Sq Ft
- Built 2004
Last Sold Summary
- $169/SF
- 1 Day On Market
Current Estimated Value $646,198
Last Listing Agent Christina Reed RE/MAX One
22272 Orchard Ct, Leonardtown, MD 20650 -
Est $522,892
Not Listed For Sale22542 Landing Way, Leonardtown, MD 20650
- 3 Beds
- 3.5 Baths
- 2,752 Sq Ft
- Built 2005
Last Sold Summary
- 21 Days On Market
Last Listing Agent Trish Brow O'Brien Realty ERA Powered
-
$450,000
$50K PRICE DROP- 2 Beds
- 1 Bath
- 1,018 Sq Ft
20798 Waterside Dr, Leonardtown, MD 20650
20798 Waterside Dr, Leonardtown, MD 20650
Connie Fitzgerald
RE/MAX One
-
$2,000 Per Month
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
- House for Rent
39685 Lady Baltimore Ave, Leonardtown, MD 20650
39685 Lady Baltimore Ave, Leonardtown, MD 20650Welcome to your ideal rental in Leonardtown! This charming property offers a comfortable living experience in a vibrant community, perfect for anyone seeking a cozy space in a flourishing area. Key property features include spacious bedrooms, well-appointed bathrooms, and an inviting layout that maximizes floor space. You’ll find yourself just minutes away from a variety of excellent
-
$1,100,000
Sold May 15, 202620045 Tower Hill Rd, Leonardtown, MD 20650
- 5 Beds
- 7 Baths
- 7,376 Sq Ft
- Built 1973
Last Sold Summary
- 24% Below List Price
- $149/SF
- 12 Days On Market
Current Estimated Value $1,141,458
Last Listing Agent Barbara Stellway KW Metro Center
20045 Tower Hill Rd, Leonardtown, MD 20650 -
Est $717,719
Not Listed For Sale20620 Laurel Ct, Leonardtown, MD 20650
- 5 Beds
- 3 Baths
- 3,500 Sq Ft
- Built 2001
Last Sold Summary
- 4 Days On Market
Last Listing Agent Amy Gallo RE/MAX One
-
$120,000
- Land
- 20,037 Sq Ft
- $260,870 per Acre
0 Lake Dr Unit MDSM2033374, Valley Lee, MD 20692
0 Lake Dr Unit MDSM2033374, Valley Lee, MD 20692 -
$1,500 Per Month
- 1 Bed
- 1 Bath
- 900 Sq Ft
- Condo for Rent
39725 Lady Baltimore Ave Unit in law apt, Leonardtown, MD 20650
39725 Lady Baltimore Ave Unit in law apt, Leonardtown, MD 20650Property Id: 2750149 One level living ONE large bedroom - one good size completely modernized bathroom. Large breezeway living room Full size eat -in kitchen. New luxury vinyl flooring throughout. Freshly painted Has own laundry room with washer and dryer No shared areas - private entrance Large yard Beach access sticker is provided to
-
$731,084
Sold Dec 04, 202540744 Fawns Rest Way, Leonardtown, MD 20650
- 4 Beds
- 3 Baths
- 3,313 Sq Ft
- Built 2025
Last Sold Summary
- $221/SF
- 0 Days On Market
Last Listing Agent Laura Lee Hefley RE/MAX One
40744 Fawns Rest Way, Leonardtown, MD 20650 -
Est $565,658
Not Listed For Sale22530 Bull Rd, Leonardtown, MD 20650
- 3 Beds
- 3 Baths
- 1,976 Sq Ft
- Built 1971
Last Sold Summary
Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty
-
$435,000
Pending- 4 Beds
- 2.5 Baths
- 2,624 Sq Ft
40717 Lake and Breton View Dr, Leonardtown, MD 20650
40717 Lake and Breton View Dr, Leonardtown, MD 20650Farrah Fuchs Redfin Corp
-
$1,650 Per Month
- 2 Beds
- 1 Bath
- 1,500 Sq Ft
- Condo for Rent
39725 Lady Baltimore Ave Unit main, Leonardtown, MD 20650
39725 Lady Baltimore Ave Unit main, Leonardtown, MD 20650Property Id: 2786281 Renter must : Make 2.5 times the rent Steady employment history No prior evictions or Failure to pay rent court dates Good prior landlord reference Criminal background check performed on all adults on lease Please complete the pre-screening questionnaire before messaging. Applicants who meet the basic requirements will receive a
-
$961,000
Sold May 28, 202640003 Tippit Rd, Leonardtown, MD 20650
- 3 Beds
- 3 Baths
- 2,490 Sq Ft
- Built 1900
Last Sold Summary
- 3% Below List Price
- $386/SF
- 23 Days On Market
Current Estimated Value $930,561
Last Listing Agent Charlotte Long EXP Realty, LLC
40003 Tippit Rd, Leonardtown, MD 20650 -
Est $732,329
Not Listed For Sale22064 Daffodil Ct, Leonardtown, MD 20650
- 6 Beds
- 4.5 Baths
- 5,012 Sq Ft
- Built 2022
Last Sold Summary
- 43 Days On Market
Last Listing Agent Laura Lee Hefley RE/MAX One
-
$449,900
New Construction Pending- 4 Beds
- 3.5 Baths
- 2,554 Sq Ft
Lot 158 - 23646 Dragonfly Ln, Leonardtown, MD 20650
Lot 158 - 23646 Dragonfly Ln, Leonardtown, MD 20650Laura Lee Hefley RE/MAX One
-
$4,000
Total Monthly Price
- 4 Beds
- 4 Baths
- 4,488 Sq Ft
- House for Rent
19968 Tower Hill Rd, Leonardtown, MD 20650
19968 Tower Hill Rd, Leonardtown, MD 20650Feel like you're vacationing every day in this gorgeous house in the serene woods with magnificent lake views from every room. As you step inside this 4500 sq foot house, you'll immediately fall in love with the soaring ceilings and the incredible views. The large windows allow natural light to flood in, and provide daily views of bald eagles, great blue herons, beavers, river otters, foxes,
-
$518,500
Sold Dec 05, 202522539 Landing Way, Leonardtown, MD 20650
- 3 Beds
- 3.5 Baths
- 2,764 Sq Ft
- Built 2005
Last Sold Summary
- $188/SF
- 12 Days On Market
Current Estimated Value $517,622
Last Listing Agent Trish Brow O'Brien Realty ERA Powered
22539 Landing Way, Leonardtown, MD 20650 -
Est $573,088
Not Listed For Sale23330 Lindsay Dr, Leonardtown, MD 20650
- 3 Beds
- 3 Baths
- 1,926 Sq Ft
- Built 2022
Last Sold Summary
- 0 Days On Market
Last Listing Agent Kristen Quinn Realty Navigator
-
$449,900
New Construction Pending- 4 Beds
- 3.5 Baths
- 2,604 Sq Ft
Lot 144 - 23635 Dragonfly Ln, Leonardtown, MD 20650
Lot 144 - 23635 Dragonfly Ln, Leonardtown, MD 20650Laura Lee Hefley RE/MAX One
-
$1,500 Per Month
- 2 Beds
- 1 Bath
- 4,112 Sq Ft
- Townhouse for Rent
44868 Blake Creek Rd, Valley Lee, MD 20692
44868 Blake Creek Rd, Valley Lee, MD 20692Small duplex apartment with Living Room, Den/Study, laundry room, eat-in kitchen, one bath and two bedrooms. Max two occupants. No pets allowed. Still waiting on a few repairs, but available for occupancy.Looking for good credit and background check. Off street parking. Total of four apartments in two building with two units per building. Freshly painted and new carpets.
Jan Barnes CENTURY 21 New Millennium
-
$639,000
Sold Oct 30, 202541474 Charismatic Way, Leonardtown, MD 20650
- 5 Beds
- 3.5 Baths
- 3,647 Sq Ft
- Built 2015
Last Sold Summary
- $175/SF
- 57 Days On Market
Current Estimated Value $650,300
Last Listing Agent Laura Lee Hefley RE/MAX One
41474 Charismatic Way, Leonardtown, MD 20650 -
Est $468,981
Not Listed For Sale40077 Big Chestnut Rd, Clements, MD 20624
- 5 Beds
- 3 Baths
- 2,184 Sq Ft
- Built 2008
Last Sold Summary
- 32 Days On Market
Last Listing Agent Dorothy Bistransin Redfin Corp
-
$85,000
$9K PRICE DROP Pending- Land
- 4.11 Acres
- $20,681 per Acre
00 Saint Andrews Church Rd, Leonardtown, MD 20650
00 Saint Andrews Church Rd, Leonardtown, MD 20650 -
$1,250 Per Month
- 1 Bed
- 1 Bath
- 800 Sq Ft
- House for Rent
23220 Spalding Ln, Leonardtown, MD 20650
23220 Spalding Ln, Leonardtown, MD 20650Basement apartment with one bedrooms, and a den/study, kitchen, dining and living room combo. One full bath, washer/dryer provided. House above is occupied. Max of two tenants with good credit. Yard available for enjoyment. No pets!!! Water.sewer and trash taken care of by owner. Just pay your electric and cable/wifi. $1250 for one person, $1300 for two occupants monthly rent
Jan Barnes CENTURY 21 New Millennium
-
$720,000
Sold Jun 26, 202641395 Omaha Ct, Leonardtown, MD 20650
- 5 Beds
- 3.5 Baths
- 4,367 Sq Ft
- Built 2012
Last Sold Summary
- 1% Above List Price
- $165/SF
- 1 Day On Market
Current Estimated Value $711,947
Last Listing Agent Andrew Shemeta CENTURY 21 New Millennium
41395 Omaha Ct, Leonardtown, MD 20650 -
Est $702,234
Not Listed For Sale18914 Russell Rd, Valley Lee, MD 20692
- 3 Beds
- 2.5 Baths
- 2,020 Sq Ft
- Built 1999
Last Sold Summary
- 66 Days On Market
Last Listing Agent Michelle Camaioni RE/MAX One
-
$609,900
New Construction- 4 Beds
- 2.5 Baths
- 2,701 Sq Ft
The Mattingly Plan at Meadows at Town Run - Single Family Homes, Leonardtown, MD 20650
23731 Dragonfly Ln Unit 41509706, Leonardtown, MD 20650Quality Built Homes Builder -
$2,000 Per Month
- 2 Beds
- 1.5 Baths
- 1,568 Sq Ft
- House for Rent
39534 Potomac Ave, Leonardtown, MD 20650
39534 Potomac Ave, Leonardtown, MD 20650Enjoy the charm of waterfront living in this cozy cottage nestled in one of Leonardtown’s most desirable water-oriented neighborhoods. Offering beautiful water views and a peaceful setting, this home is perfect for anyone looking to enjoy the relaxed Southern Maryland lifestyle while remaining just minutes from everything downtown Leonardtown has to offer.The home’s comfortable layout
Sean Escobar O'Brien Realty ERA Powered
-
$575,000
Sold Mar 05, 202621060 Woodmere Dr, Leonardtown, MD 20650
- 5 Beds
- 3.5 Baths
- 3,075 Sq Ft
- Built 2001
Last Sold Summary
- 2% Above List Price
- $187/SF
- 18 Days On Market
Current Estimated Value $574,309
Last Listing Agent Sharon Cox Century 21 Redwood Realty
21060 Woodmere Dr, Leonardtown, MD 20650 -
Est $461,637
Not Listed For Sale22605 Calvert St, Leonardtown, MD 20650
- 4 Beds
- 3 Baths
- 2,340 Sq Ft
- Built 2018
Last Sold Summary
- 62 Days On Market
Last Listing Agent kyle Antel Berkshire Hathaway HomeServices PenFed Realty
-
$489,900
New Construction Pending- 4 Beds
- 3.5 Baths
- 3,095 Sq Ft
Lot 151 - 23790 Wisteria Ln, Leonardtown, MD 20650
Lot 151 - 23790 Wisteria Ln, Leonardtown, MD 20650Laura Lee Hefley RE/MAX One
-
$2,500 Per Month
- 2 Beds
- 1.5 Baths
- 1,024 Sq Ft
- House for Rent
41603 Church St, Leonardtown, MD 20650
41603 Church St, Leonardtown, MD 20650Less house. More Leonardtown. Be the first to call this brand-new Leonardtown cottage home. Built by the same builder as 41577 Church Street and finished in the same fresh, modern style, 41603 Church Street offers two bedrooms, 1.5 baths and an easy, thoughtfully designed floor plan right in town. The main level includes comfortable living and dining spaces, a well-planned kitchen and a
Michelle Camaioni RE/MAX One
-
$459,900
Sold Jun 17, 202640810 Meadow Dr, Leonardtown, MD 20650
- 3 Beds
- 2 Baths
- 1,368 Sq Ft
- Built 1963
Last Sold Summary
- $336/SF
- 14 Days On Market
Current Estimated Value $453,935
Last Listing Agent Cheryl Bare CENTURY 21 New Millennium
40810 Meadow Dr, Leonardtown, MD 20650 -
Est $544,401
Not Listed For Sale22301 Bayside Rd, Leonardtown, MD 20650
- 4 Beds
- 2.5 Baths
- 2,368 Sq Ft
- Built 2012
Last Sold Summary
- 63 Days On Market
Last Listing Agent Chad Istvan EXP Realty, LLC
Showing Results 1 - 40, Page 1 of 18
Copyright © 2026 CoStar Group
