Homes with a View for Sale in Leonardtown, MD

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FLOOR PLAN

ABOUT THIS HOME
Home with View for sale in Leonardtown, MD:
Rare Waterfront Estate in Leonardtown! Nestled on 26.62 scenic acres, this charming Cape Cod farmhouse offers an unbeatable blend of pastoral beauty and waterfront living. Enjoy sweeping views of Blake Creek, extensive water frontage, and a private pier—perfect for kayaking, paddle boarding, crabbing, fishing, and peaceful small motor boating on this quiet tidal inlet. Inside, thoughtful additions provide multiple living spaces for relaxing and entertaining. The main level features a welcoming entry sitting room with a brick-surrounded electric fireplace, a spacious family room with a wood stove, and a dramatic sunroom with vaulted beam ceilings and a wall of sliding glass doors showc

$850,000

3 beds3 baths2,731 sq ft

19445 Blake Farms Ln, Leonardtown, MD 20650

Waterfront estate • Private pier • Spacious family room

(301) 863-2400

ABOUT THIS HOME
Home with View for sale in Leonardtown, MD:
2.25% Assumable VA loan & one of the largest lots in Leonard's Grant at . 64 acres! This brilliant Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Lots of fruit trees (Fig, Apple, Mulberry, Dwarf Peach, Pear, Strawberry and Persimmon). Enter to find gorgeous exotic hardwood tigerwood floors flowing seamlessly across the main level into the Kitchen where you will be invited to Andura Max floors. Screened porch to enjoy beautiful sunsets. The finished basement is an entertainer's dream, featuring a dedicated theater area ready for your custom equipment, the spare guest bedroom and a walk-out basement. Enjoy peace of mind with tan

$749,900

5 beds4 baths4,873 sq ft

41402 Omaha Ct, Leonardtown, MD 20650

Finished basement • Screened porch • Andura max floors

(855) 450-0442

ABOUT THIS HOME
Home with View for sale in Leonardtown, MD:
Experience breathtaking panoramic views of Breton Bay and unforgettable sunsets! Cape Cod-style home featuring 3 bedrooms plus a spacious loft. Designed to maximize the water views, the home offers hardwood floors throughout and an inviting floor plan with a living room, family room, dining room, and breakfast room—all overlooking the bay. Enjoy the expansive 37' x 8' front porch or the equally generous 37' x 8' rear porch, where you can relax and take in the peaceful waterfront scenery. Recent updates include new siding, a new roof, and a new gutter system. The side-load garage includes a staircase leading to a large upper-level storage area. Perfectly situated next to the neighborho

$750,000

3 beds2.5 baths2,304 sq ft

40579 Port Pl, Leonardtown, MD 20650

Water views • New siding • Expansive rear porch

(301) 208-2288

ABOUT THIS HOME
Home with View for sale in Leonardtown, MD:
Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year. Perfectly positioned to capture breathtaking water views, this exceptional property offers a rare opportunity to own a private waterfront oasis with an expansive shoreline along both Breton Bay and Combs Creek, extending all the way to the point of its sandy beach peninsula. Enhanced riprap protection, extensive landscaping, and mature surroundings create a truly unforgettable setting. E

$1,590,000

5 beds3.5 baths2,993 sq ft

40115 Combs Creek Way, Leonardtown, MD 20650

Saltwater pool • Panoramic views • Expansive shoreline

(301) 862-2169

ABOUT THIS HOME
Home with View for sale in Leonardtown, MD:
This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal retreat. Nestled on the serene shores of McKays Cove, several major exterior capital improvements are already complete. The structure features a brand-new Amish-built roof, new gutters, and premium new Andersen windows throughout. Personal Boat Ramp: Private ramp for seamless watercraft launching and only one in the community. Private Pier: Sturdy, deep-water access steps from your back door. New Rip Rap: Fresh shoreline reinforcement ensures long-term erosion protection. Large propane tank which is almost full for newly installed gas log fireplace & furnace. All supporting floor beams in the crawl

$350,000

3 beds2 baths1,667 sq ft

18800 Mckays Beach Rd, Leonardtown, MD 20650

New rip rap • Private ramp • Private pier

(443) 295-6123

Property at 22010 Society Hill Rd, Leonardtown, MD 20650, 4 beds, 3 baths

$575,000

4 beds3 baths2,730 sq ft

22010 Society Hill Rd, Leonardtown, MD 20650

(703) 229-8935

Property at 43954 Main Way Rd, Leonardtown, MD 20650, 3 beds, 3 baths

$469,900

3 beds3 baths1,691 sq ft

43954 Main Way Rd, Leonardtown, MD 20650

(410) 729-7700

Property at 19700 Mulberry Fields Rd, Leonardtown, MD 20650, 6 beds, 4.5 baths

$15,000,000

6 beds4.5 baths5,500 sq ft

19700 Mulberry Fields Rd, Leonardtown, MD 20650

(202) 483-6300

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 Bayside Rd, Leonardtown, MD 20650, 4 beds, 2 baths

$1,750,000

4 beds2 baths2,130 sq ft

Bayside Rd, Leonardtown, MD 20650

(301) 686-0545

Property at Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650

$399,000

Land0.25 acre (lot)

Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650

(888) 860-7369

Property at Ferny Hills Ln, Leonardtown, MD 20650

$840,000

Land10.20 acres (lot)

Ferny Hills Ln, Leonardtown, MD 20650

(301) 862-2169

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COMING SOON

ABOUT THIS HOME
Home with View for sale in Leonardtown, MD:
Welcome to your dream home by the Patuxent River! This stunning 2-bedroom, 2.5-bathroom residence is available for lease, offering a perfect blend of comfort, style, and breathtaking natural surroundings. Step inside and be greeted by an abundance of gorgeous natural light that illuminates the open and spacious living areas. The home is a mix of hardwood and Luxury Vinyl Plank (LVP) flooring that not only adds a touch of modern elegance but also ensures easy maintenance. The coastal decor theme creates a relaxing and inviting atmosphere, making you feel like you're on a perpetual vacation. The house comes fully furnished, so you can move in and start enjoying the serene ambiance right away.

$799,900

2 beds2.5 baths1,871 sq ft

24753-24753 Half Pone Point Rd, Hollywood, MD 20636

Cozy living room • Laundry room • Fireplace

(240) 925-2224

ABOUT THIS HOME
Home with View for sale in Leonardtown, VA:
Nestled in the serene enclave of Glebe Harbor, this exquisite cottage-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an exclusive lifestyle by the water. Major renovations completed in 2020 have elevated this home to a standard of excellence, ensuring modern amenities while preserving its charming character. The lush landscaping and mature trees provide a picturesque backdrop, enhancing the sense of tranquility that permeates this home. A private beach awaits just steps away, offering a personal retreat for sunbathing, swimming, or simply enjoying the soothing sounds of nature. Step inside to discover a thoughtfully designed interior featuring thr

$725,000

3 beds2 baths1,836 sq ft

781 N Glebe Rd, Montross, VA 22520

Community amenities • Private beach • Lush landscaping

(703) 754-1770

ABOUT THIS HOME
Home with View for sale in Leonardtown, MD:
Welcome to waterfront living, right off Saint Clements Bay. Where beautiful views from every room, over an acre of land and direct water access create the perfect Southern Maryland home. Surrounded by water and designed to take full advantage of its incredible setting, this three-bedroom, two-and-a-half-bath home offers the lifestyle waterfront buyers are searching for. Spend your mornings taking in the peaceful views, your afternoons out on the water crabbing, and your evenings relaxing at home surrounded by the scenery. Water lovers will appreciate the private pier with water and electric, approximately 6 to 8 feet of water at high tide, and a concrete boat ramp, making it easy to enjoy b

$775,000

3 beds2.5 baths2,591 sq ft

38884 Collinwood Dr, Abell, MD 20606

Concrete boat ramp • Private pier • Waterfront living

(301) 702-4200

NEW CONSTRUCTION

ABOUT THIS HOME
Home with View for sale in Leonardtown, VA:
New Construction! Estimated Delivery Date 10/1/26. Single-level bliss has arrived. Tucked away on a peaceful cul-de-sac lot in picturesque Westmoreland County, this brand-new construction masterpiece from one of the area’s most prized builders delivers everything you’ve been searching for, introducing 191 Seagull Ct! Following the meticulously designed Huntsman floor plan by Timis Construction, this stunning home features a totally open-concept layout spanning 1,673 square feet of effortless, single-level living. From the moment you arrive, exceptional craftsmanship sets this property apart. Gorgeous accents grace the main front gable and front porch columns, perfectly compleme

$389,900

3 beds2 baths1,673 sq ft

191 Seagull Ct, Montross, VA 22520

Open floor plan • Clubhouse • Tennis courts

(540) 775-5661

NEW CONSTRUCTION

ABOUT THIS HOME
Home with View for sale in Leonardtown, VA:
New Construction! Expected Completion 10/1/26. This stunning new construction, two-story waterfront home offers the ultimate peaceful retreat right here in Montross! Introducing 194 Seagull Ct, Montross! Built by award-winning Timis Construction, this gorgeous residence includes three bedrooms, two and a half baths, 1,677 square feet of modern living space, a two-car garage, covered front and back porches, direct waterfront positioning, and so much more! It sits on a premier waterfront cul-de-sac lot in the Potomac River-Access Cabin Point community in tranquil Westmoreland County. The amenities shine in Cabin Point, featuring access to boating amenities such as two boat ramps, two storage

$399,900

3 beds2.5 baths1,677 sq ft

194 Seagull Ct, Montross, VA 22520

Boating amenities • New construction • Two boat ramps

(540) 775-5661

ABOUT THIS HOME
Home with View for sale in Leonardtown, MD:
Some properties are defined by the home, others by the land, and some by the water. .. 44742 Three Coves Road is one of those rare places where you truly get it ALL. Set on 3.4+ acres of flat and private land with 256 ft of deep-water frontage on a protected cove off Cuckold Creek, this custom brick estate offers over 5,800 sqft of living space, a 2-stall horse stable, multiple garages, and a private pier with electric and plumbing. Just minutes by boat to the Patuxent River, Chesapeake Bay, Solomons, and the surrounding area, this is Southern Maryland waterfront living at its best. Inside, a spacious foyer welcomes you before opening to the family room, where panoramic water views through

$1,100,000

4 beds6 baths5,029 sq ft

44742 Three Coves Rd, Hollywood, MD 20636

2-stall horse stable • Multiple garages • Private pier

(410) 535-6291

Property at 20824 Flour Mill Ct, Great Mills, MD 20634, 5 beds, 4.5 baths

$559,000

5 beds4.5 baths2,968 sq ft

20824 Flour Mill Ct, Great Mills, MD 20634

(443) 771-8009

Property at 17295 Oakwood Lodge Ln #6, Piney Point, MD 20674, 3 beds, 2.5 baths

$735,000

3 beds2.5 baths3,507 sq ft

17295 Oakwood Lodge Ln #6, Piney Point, MD 20674

(301) 862-2169

Property at 44908 Hickory Landing Way, Hollywood, MD 20636, 5 beds, 3 baths

$799,000

5 beds3 baths2,727 sq ft

44908 Hickory Landing Way, Hollywood, MD 20636

(410) 394-0990

Property at 45525 Coosan Ct, Great Mills, MD 20634, 2 beds, 3 baths

$395,000

2 beds3 baths1,936 sq ft

45525 Coosan Ct, Great Mills, MD 20634

(301) 862-2169

Property at 809 Salisbury Park Rd, Hague, VA 22469, 3 beds, 1 bath

$289,000

3 beds1 bath993 sq ft

809 Salisbury Park Rd, Hague, VA 22469

(804) 436-1150

Property at 45433 Drayden Rd, Valley Lee, MD 20692, 4 beds, 3 baths

$2,250,000

4 beds3 baths4,228 sq ft

45433 Drayden Rd, Valley Lee, MD 20692

(301) 208-2288

Property at 392 South Glebe Rd, Montross, VA 22520, 3 beds, 2 baths

$475,000

3 beds2 baths1,555 sq ft

392 South Glebe Rd, Montross, VA 22520

(540) 373-2000

Property at 1247 S Glebe Rd, Montross, VA 22520, 3 beds, 2.5 baths

$349,900

3 beds2.5 baths1,560 sq ft

1247 S Glebe Rd, Montross, VA 22520

(540) 775-5661

Property at 24730 Half Pone Point Rd, Hollywood, MD 20636, 4 beds, 6 baths

$4,595,000

4 beds6 baths13,665 sq ft

24730 Half Pone Point Rd, Hollywood, MD 20636

(855) 885-4663

Property at 196 Matthews Cove Dr, Montross, VA 22520, 3 beds, 2 baths

$599,000

3 beds2 baths2,229 sq ft

196 Matthews Cove Dr, Montross, VA 22520

(804) 529-7020

Property at Mirfield Ln Lexington Park Md, Lexington Park, MD 20653

$579,000

Land24.35 acres (lot)

Mirfield Ln Lexington Park Md, Lexington Park, MD 20653

(301) 645-1700

Property at 0 Hickory Point Dr, Cople, VA 22520

$250,000

Land1.98 acres (lot)

0 Hickory Point Dr, Cople, VA 22520

(540) 775-5661

Property at 20767 Abell Rd, Abell, MD 20606

$199,999

Land2.99 acres (lot)

20767 Abell Rd, Abell, MD 20606

(443) 771-8009

Property at Lot 14 Warner Ln, Hague, VA 22469

$20,000

Land4,356 sq ft (lot)

Lot 14 Warner Ln, Hague, VA 22469

(540) 625-8100

Homes with a View for Sale in Leonardtown

There are currently 12 homes with a view homes for sale in Leonardtown at a median listing price of $610K. 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 56 days. This map is refreshed with the newest listings in Leonardtown every 15 minutes.

In the past month, 9 homes have been sold in Leonardtown. In addition to houses in Leonardtown, there was also 1 condo, 9 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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