Homes for sale under $500k in Leonardtown, MD

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ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
Unique property : Residential AND Commercial !!! The two story home has 3 bedrooms, one bath, replaced furnace, window AC units, storage, partial unfinished basement. Needs updating. The former Doctor's office has had some updating recently. New heat pump last year. Both are on separate electric meters, heating and cooling systems. Ample parking behind building for both units. Showings by appointments only. Tenant in the Commercial building at present. House is empty.

$497,500

3 beds2 baths2,952 sq ft

25365 Point Lookout Rd, Leonardtown, MD 20650

New heat pump • Ample parking • Replaced furnace

(301) 862-2169

OPEN DEC 2, 9AM TO 10:15AMVIDEO TOUR

ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
* * * HOME IN TIME FOR THE HOLIDAYS, Receive $20,000 in Builder Credit plus $12,500 in Closing Help OR $20,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. (Builder to honor promotional pricing for contracts that close by 12/31/25. Offer valid for Homesite 103 only. Must use preferred lender and title to receive closing assistance. ) New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This ex

$489,900

4 beds3.5 baths— sq ft

Lot 103-23701 Dragonfly Ln, Leonardtown, MD 20650

Finished rec room • Walk-in pantry • $71 HOA

(443) 771-8009

READY TO BUILD

ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
Discover the spacious Cumberland D1 end-unit townhome by Quality Built Homes. This 3-level, 3095 sq ft home blends functionality, natural light, and refined style. The entry level features a finished rec room (or optional 4th bedroom) with a full bath and walkout access to the backyard, perfect for guests, a home office, or second living space. The oversized one-car garage and wide driveway offer ample parking and storage. The main level boasts 9' ceilings, luxury vinyl plank flooring, and an entertainer's kitchen with 42" upgraded maple cabinetry, soft-close drawers, granite countertops, a large center island, walk-in pantry, and stainless GE appliances. The open-concept dining and fa

$479,900

4 beds3.5 baths3,095 sq ft

Cumberland D1 Plan, Leonardtown, MD 20650

Finished rec room • Wide driveway • Walkout access

Listing provided by Zillow

READY TO BUILD

ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
Discover the Oakley D1 end-unit townhome at Meadows at Town Run II, built by Quality Built Homes in the heart of Leonardtown, Maryland. Offering 2,966 sq ft of modern living, this home blends style and functionality with spacious, light-filled rooms. The main level features a finished rec room or optional 4th bedroom with a full bath and backyard access-ideal for guests, a home office, or extra living space. The oversized one-car garage and wide driveway provide ample parking and storage. Upstairs, enjoy 9' ceilings, luxury vinyl plank flooring, and a gourmet kitchen with upgraded 42" maple cabinetry, soft-close drawers, granite countertops, a large island, walk-in pantry, and stainles

$469,900

4 beds3.5 baths2,966 sq ft

Oakley D1 Plan, Leonardtown, MD 20650

Finished rec room • End-unit townhome • Gourmet kitchen

Listing provided by Zillow

ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
This is a large 3 bedrooms, 2 bath, and large sunroom on 2nd level home with large family room with wood stove insert, large laundry room, and accessory area on the lower level. Also has a 2 Car Detached garage built in 2008. Roof of garage and house was re-shingled in 2020 with 50 year shingles. The HVAC was regularly serviced.

$465,000

3 beds2 baths2,527 sq ft

21925 Budds Creek Rd, Leonardtown, MD 20650

1.28 acre lot • 4 garage spots • Built 1970

(301) 884-9493

Property at 20798 Waterside Dr, Leonardtown, MD 20650, 2 beds, 1 bath

$450,000

2 beds1 bath1,018 sq ft

20798 Waterside Dr, Leonardtown, MD 20650

(410) 535-6291

Property at Lot 104- 23695 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths— sq ft

Lot 104- 23695 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 105- 23689 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths— sq ft

Lot 105- 23689 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at lot 106-23683 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths— sq ft

lot 106-23683 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths— sq ft

Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Madison D2 Plan, Leonardtown, MD 20650, 4 beds, 3.5 baths

$445,900

4 beds3.5 baths2,604 sq ft

Madison D2 Plan, Leonardtown, MD 20650

Listing provided by Zillow

Property at Madison D1 Plan, Leonardtown, MD 20650, 4 beds, 3.5 baths

$445,900

4 beds3.5 baths2,571 sq ft

Madison D1 Plan, Leonardtown, MD 20650

Listing provided by Zillow

Property at Madison D3 Plan, Leonardtown, MD 20650, 4 beds, 3.5 baths

$445,900

4 beds3.5 baths2,554 sq ft

Madison D3 Plan, Leonardtown, MD 20650

Listing provided by Zillow

Property at 20959 Redgate Ln, Leonardtown, MD 20650, 3 beds, 1 bath

$219,000

3 beds1 bath1,026 sq ft

20959 Redgate Ln, Leonardtown, MD 20650

(443) 660-9229

Property at 44646 Medleys Neck Rd, Leonardtown, MD 20650, 3 beds, 1 bath

$80,000

3 beds1 bath924 sq ft

44646 Medleys Neck Rd, Leonardtown, MD 20650

(301) 862-4000

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ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
Option of an Assumable Loan! Welcome to 21312 Fox Wood Lane in the sought after Elizabeth Hills neighborhood, a charming 4-bedroom, 2-bath home nestled on a quiet cul-de-sac in California, MD. This beautifully maintained property features an updated kitchen, luxury vinyl plank flooring throughout, and a spacious primary suite with a private bath. The backyard is perfect for entertaining, with a beautiful deck with no maintenance boarding and a serene, private setting. The walk-up basement with 9-foot ceilings offers endless potential for a wet bar, an additional full bath, and more living space. Close to schools, PAX River, parks, and shopping, this home offers comfort, style, and room to g

$500,000

4 beds2.5 baths2,360 sq ft

21312 Fox Wood Ln, California, MD 20619

7,500 sq ft lot • 2 garage spots • Built 2018

(301) 298-2892

ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
FINANCING AVAILABLE! - Imagine waking up each day to breathtaking sunrises over Saint Clements Bay! This delightful cottage offers a tranquil, vacation-like lifestyle with no HOA and prime waterfront access. It also presents income potential as it can sleep six. Meticulous planning has crafted this stunning home, which exudes the elegance of a high-end interior designer. Inside, you'll find a bright and airy living area that effortlessly merges indoor and outdoor spaces, showcasing captivating water views. The cottage boasts 12-foot ceilings, unique metal roof with cupola and weathervane, an upgraded well pressure tank, robust 200-amp service, full-sized washer and dryer, and a beautifully

$499,000

1 bed1 bath392 sq ft

39020 Sonnie Way, Clements, MD 20624

Unique metal roof • Waterfront access • 12 foot ceilings

(888) 860-7369

ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
Spectacular views of the Potomac River from the back yard and house! This 2 cozy 2 bed 1 bath charmer is the dream river home you have been waiting for. One of the best views in the Northern Neck and Coles Point area. Comes with a detached 2 car garage for all your water toys and boat. Across the street is a lot that belongs to the house if you want to build another garage with mother in law suite. New roof put on in 2024.

$495,000

2 beds1 bath840 sq ft

63 Bayview Ln, Hague, VA 22469

Lot for building • Potomac river views • Detached garage

ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
Beautiful home in the Northern Neck situated on 1.11 acres with incredible water views. The main home offers 3 bedrooms, 2 full baths, and a bright open floor plan with lots of windows, crown moulding, and wainscoting throughout. The family room features a propane fireplace with custom hearth and built-in shelving. The spacious kitchen includes new stainless steel appliances, granite countertops, seating at the island, room for a dining table, and a butler’s pantry with a second refrigerator. Additional highlights include a sunroom with water views, ceiling fans throughout, and a primary suite with walk-in closet, large bath with dual vanities, and heated flooring. * * * Outdoor li

$495,000

4 beds3.5 baths2,700 sq ft

4387 Coles Point Rd, Hague, VA 22469

1.11 acre lot • 2 garage spots • Built 2005

(703) 430-9008

NEW CONSTRUCTION

ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
New Construction. Buy it now and pick your own colors and have it completed according to your wishes. Spacious Two Story New House, 6 Bedrooms, 4 upstairs and 2 on main floor. Great room, front porch, large veranda on back, and 2 car garage. This beautiful home is located in Cabin Point, a highly desirable subdivision in Westmoreland County with many amenities. Walking distance to sand beach on the Potomac River. Sanitary District Fee is $215 is due annually with payment of real estate taxes. Construction site, enter at your own risk.

$494,000

6 beds3 baths2,421 sq ft

1017 Royal Way, Montross, VA 22520

0.5 acre lot • 2 garage spots • Built 2023

REDFIN COMING SOON3D WALKTHROUGH

ABOUT THIS HOME
Homes for sale under $500k in Leonardtown, MD
Details coming soon — you won’t want to miss this beautiful home!

$489,900

4 beds2.5 baths2,169 sq ft

23175 Whistlewood Ln, California, MD 20619

0.33 acre lot • 2 garage spots • Built 2002

Property at 17850 4th St, Tall Timbers, MD 20690, 4 beds, 3.5 baths

$489,000

4 beds3.5 baths2,495 sq ft

17850 4th St, Tall Timbers, MD 20690

(888) 860-7369

Property at 44892 Golden Eye Ct, Callaway, MD 20620, 4 beds, 2.5 baths

$485,000

4 beds2.5 baths2,536 sq ft

44892 Golden Eye Ct, Callaway, MD 20620

(410) 535-6291

Property at 20932 Sawgrass Dr, Lexington Park, MD 20653, 4 beds, 3.5 baths

$485,000

4 beds3.5 baths3,490 sq ft

20932 Sawgrass Dr, Lexington Park, MD 20653

(833) 335-7433

Property at TBD Lot 28 South Glebe Rd, Montross, VA 22520, 3 beds, 2 baths

$475,000

3 beds2 baths1,200 sq ft

TBD Lot 28 South Glebe Rd, Montross, VA 22520

(540) 373-2000

Property at 23015 Wedgewood Ln, California, MD 20619, 3 beds, 2.5 baths

$474,900

3 beds2.5 baths1,728 sq ft

23015 Wedgewood Ln, California, MD 20619

(240) 925-2224

Property at 45890 Skipjack Dr, Lexington Park, MD 20653, 4 beds, 4 baths

$470,000

4 beds4 baths3,402 sq ft

45890 Skipjack Dr, Lexington Park, MD 20653

(240) 737-5000

Property at 44913 Widgeon Pl, Callaway, MD 20620, 4 beds, 2.5 baths

$469,900

4 beds2.5 baths2,430 sq ft

44913 Widgeon Pl, Callaway, MD 20620

(301) 843-5100

Property at 19809 Point Lookout Rd, Lexington Park, MD 20653, 4 beds, 2.5 baths

$469,000

4 beds2.5 baths3,268 sq ft

19809 Point Lookout Rd, Lexington Park, MD 20653

(301) 884-9493

Property at 44183 Goldenzelle Way, California, MD 20619, 4 beds, 3.5 baths

$464,900

4 beds3.5 baths2,232 sq ft

44183 Goldenzelle Way, California, MD 20619

(240) 925-2224

Property at 23609 Crosswinds Way, California, MD 20619, 4 beds, 3.5 baths

$450,800

4 beds3.5 baths2,452 sq ft

23609 Crosswinds Way, California, MD 20619

Property at 45429 Englewood Way, California, MD 20619, 3 beds, 3.5 baths

$450,000

3 beds3.5 baths2,548 sq ft

45429 Englewood Way, California, MD 20619

(301) 684-4895

Property at 45301 Foghorn Way, California, MD 20619, 3 beds, 3.5 baths

$450,000

3 beds3.5 baths2,772 sq ft

45301 Foghorn Way, California, MD 20619

(610) 363-4300

Property at Barbados Isle Plan, 3q6m1e California, MD 20619, 3 beds, 2 baths

$449,990

3 beds2 baths1,369 sq ft

Barbados Isle Plan, 3q6m1e California, MD 20619

Listing provided by Zillow

Property at 23272 Hickory Hollow Ln, California, MD 20619, 4 beds, 2.5 baths

$449,000

4 beds2.5 baths2,072 sq ft

23272 Hickory Hollow Ln, California, MD 20619

(443) 771-8009

Homes for sale under $500k in Leonardtown

There are currently 15 homes for sale under $500k in Leonardtown. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Leonardtown stay on the market for 53 days. This map is refreshed with the newest listings in Leonardtown every 15 minutes.

In the past month, 11 homes have been sold in Leonardtown. In addition to houses in Leonardtown, there was also 1 condo, 11 townhouses, and 0 multi-family units for sale in Leonardtown last month. Find your dream home in Leonardtown using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Leonardtown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Leonardtown. Our Leonardtown real estate stats and trends will give you more information about home buying and selling trends in Leonardtown. If you're looking to sell your home in the Leonardtown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Leonardtown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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