Homes with Pools for Sale in Leonardtown, MD

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ABOUT THIS HOME
Home with a Pool 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 a Pool for sale in Leonardtown, MD:
Welcome to Avenmar, where this spacious home is situated on a beautiful lot of over two acres, offering privacy, mature trees, and a peaceful wooded setting. Built in 2002 and largely in its original condition, the home has been well maintained and is ready for its next owner to bring their own style and updates. The main level offers a spacious, open layout with a formal dining room, formal living room, private office, and full bath. The centerpiece of the home is the impressive two-story family room with a gas fireplace and floor-to-ceiling windows overlooking the trees and woods. The kitchen features Corian countertops, solid hardwood cabinetry, generous workspace, and an easy flow into

$780,000

5 beds4 baths5,484 sq ft

22601 Avenmar Dr, Leonardtown, MD 20650

Corian countertops • Gas fireplace • Two acres

(301) 862-2169

OPEN SAT, 10AM TO 12PM

ABOUT THIS HOME
Home with a Pool for sale in Leonardtown, MD:
Welcome to 41524 Fairwood Ct, Leonardtown, MD 20650! This inviting ranch-style home offers comfortable one-level living with a spacious, open-concept great room, dining area, and kitchen designed for everyday living and entertaining. The kitchen features a generous island and built-in pantry, while the convenient mudroom and first-floor laundry add functionality. The thoughtful layout includes two bedrooms with a shared bath, plus a private owner’s suite featuring a spa-like shower and walk-in closet. The finished partial basement provides additional living space with a recreation room, full bath, and bedroom—perfect for guests, a home office, or additional entertaining space. A

$600,000

4 beds3 baths3,793 sq ft

41524 Fairwood Ct, Leonardtown, MD 20650

Built-in pantry • Generous island • Spa-like shower

(301) 298-2892

ABOUT THIS HOME
Home with a Pool 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 a Pool for sale in Leonardtown, MD:
Welcome to this beautiful brick-front home in the highly sought-after Avenmar Community of historic Leonardtown, Maryland. Situated on over 3 private acres and tucked away on a secluded road shared by only three other homes, this property offers the perfect balance of privacy, nature, and convenience. Freshly updated with a new roof, new carpet throughout, and fresh paint, this move-in-ready home features 4 bedrooms, 2.5 bathrooms, and overflows with charm and comfort. The spacious primary suite includes its own fireplace, a large walk-in closet, and an impressive ensuite bath with a Jacuzzi tub. A second fireplace in the family room creates a warm and inviting gathering space for family an

$650,000

5 beds2.5 baths2,601 sq ft

40751 Merlin Way, Leonardtown, MD 20650

Private acres • Fresh paint • New carpet

(240) 993-9888

Property at 23214 Dairy Barn Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$695,000

5 beds3.5 baths4,084 sq ft

23214 Dairy Barn Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 23760 Coventry Dr, Leonardtown, MD 20650, 5 beds, 4 baths

$714,900

5 beds4 baths4,744 sq ft

23760 Coventry Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 40115 Combs Creek Way, Leonardtown, MD 20650, 5 beds, 3.5 baths

$1,590,000

5 beds3.5 baths2,993 sq ft

40115 Combs Creek Way, Leonardtown, MD 20650

(301) 862-2169

Property at 40611 Merion Ct, Leonardtown, MD 20650, 4 beds, 3.5 baths

$624,990

4 beds3.5 baths2,562 sq ft

40611 Merion Ct, Leonardtown, MD 20650

(240) 925-2224

Property at 23636 Hansel Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$610,000

4 beds2.5 baths4,836 sq ft

23636 Hansel Ct, Leonardtown, MD 20650

(301) 970-2447

Property at Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths— sq ft

Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at 40777 Center 40 Cir, Leonardtown, MD 20650, 4 beds, 2.5 baths

$524,900

4 beds2.5 baths2,370 sq ft

40777 Center 40 Cir, Leonardtown, MD 20650

(301) 862-2169

Property at 23628 Belmar Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$715,000

5 beds3.5 baths4,834 sq ft

23628 Belmar Dr, Leonardtown, MD 20650

(443) 771-8009

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 41462 Culpepper Way, Leonardtown, MD 20650, 4 beds, 3.5 baths

$635,000

4 beds3.5 baths3,314 sq ft

41462 Culpepper Way, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths— sq ft

Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at 23591 Margrave Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$649,000

5 beds3.5 baths4,051 sq ft

23591 Margrave Dr, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths2,604 sq ft

Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$454,900

4 beds3.5 baths2,554 sq ft

Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$454,900

4 beds3.5 baths2,571 sq ft

Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

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Nearby homes that match your criteria

ABOUT THIS HOME
Home with a Pool for sale in Leonardtown, MD:
Welcome to this spacious 4-bedroom, 3.5-bath Colonial tucked away on a quiet cul-de-sac in the sought-after Westbury community. Offering three levels of living space and an attached two-car garage, this home provides the room and flexibility today’s buyers are looking for. The main level features beautiful hardwood floors and an inviting layout with a formal dining room accented by crown molding and chair railing, plus a light-filled living room that could easily serve as a home office. The spacious eat-in kitchen offers abundant cabinetry, stainless steel appliances, and plenty of room for casual dining. It opens to the comfortable family room, making the space ideal for both everyda

$455,000

4 beds3.5 baths2,084 sq ft

21564 Gordon Ct, Lexington Park, MD 20653

Community amenities • Finished basement • Pool

(443) 771-8009

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Leonardtown, MD:
Wselcome to 22995 Wedgewood Lane, a truly one-of-a-kind home located in the highly sought-after Wildewood community. Offering an impressive combination of space, character, and indoor-outdoor living, this home provides a layout designed for both comfortable everyday living and entertaining. The spacious main level is highlighted by an abundance of natural light and a large sunroom, creating the perfect place to relax, gather with friends and family, or simply enjoy views of the surrounding property. Generous living spaces throughout the home provide flexibility for a variety of lifestyles. Downstairs, the large finished and highly functional basement adds tremendous usable living space with

$474,900

3 beds3 baths3,090 sq ft

22995 Wedgewood Ln, California, MD 20619

Large sunroom • Hardscaping • Finished basement

(240) 925-2224

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Leonardtown, MD:
Welcome to convenient condominium living in Great Mills! This spacious 1-bedroom, 1.5-bath main-level condo offers an open-concept floor plan, abundant storage, and a location just minutes from PAX, shopping, dining, and major commuter routes. The inviting living and dining area provides plenty of room to relax or entertain, while the adjoining kitchen features oak cabinetry, stainless-steel appliances, and a pantry closet. Step outside to the balcony for a breath of fresh air, with an additional storage/utility closet conveniently located just off the outdoor space. The spacious bedroom offers a private en-suite bathroom with dual sinks and two walk-in closets, providing exceptional storag

$174,999

1 bed1.5 baths879 sq ft

45522 Westmeath Way Unit A12, Great Mills, MD 20634

Oak cabinetry • Balcony • Main-level condo

(240) 737-5000

ABOUT THIS HOME
Home with a Pool for sale in Leonardtown, MD:
Beautiful, spacious Colonial ideally located near the back entrance of sought-after Wildewood! From the moment you arrive, this home makes an impression with its welcoming front porch, beautifully maintained landscaping, and peaceful setting overlooking trees rather than another home. Step inside to a spacious foyer and gleaming hardwood floors that flow throughout the main living areas. The thoughtful floor plan offers a private home office with French doors, a large formal dining room, butler’s pantry, and an inviting great room that opens to the eat-in kitchen. The gourmet kitchen is truly the heart of the home, featuring upgraded appliances, abundant cabinetry, and plenty of space

$645,000

4 beds4.5 baths3,800 sq ft

43693 Wild Iris St, California, MD 20619

0.25 acre lot • 2 garage spots • Community pool

(443) 771-8009

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Leonardtown, VA:
Whether you're looking for a peaceful vacation getaway or a full-time waterfront residence, this home truly checks all of the boxes. With direct access to the water, you can enjoy kayaking, fishing, boating, or simply relaxing and taking in the beauty of your surroundings. Located in the sought-after Glebe Harbor/Cabin Point community, you'll have access to an outdoor pool, beaches, tennis courts, picnic areas, and a boat ramp-so there's always something to enjoy right outside of your door. This is more than just a home; it's a lifestyle. Offering the perfect blend of comfort, recreation, and natural beauty, this property gives you the opportunity to enjoy waterfront living where every day

$679,900

4 beds3 baths2,467 sq ft

780 S Glebe Rd, Montross, VA 22520

Outdoor pool • Tennis courts • Waterfront living

(301) 870-7653

$438,000

3 beds3 baths2,054 sq ft

44569 Nolani Way, California, MD 20619

2 garage spots • Community pool • Built 2022

(301) 934-9985

Property at 781 N Glebe Rd, Montross, VA 22520, 3 beds, 2 baths

$725,000

3 beds2 baths1,836 sq ft

781 N Glebe Rd, Montross, VA 22520

(703) 754-1770

Property at 191 Seagull Ct, Montross, VA 22520, 3 beds, 2 baths

$389,900

3 beds2 baths1,673 sq ft

191 Seagull Ct, Montross, VA 22520

(540) 775-5661

Property at 45 Jaws Ct, Montross, VA 22520, 3 beds, 2 baths

$297,000

3 beds2 baths1,408 sq ft

45 Jaws Ct, Montross, VA 22520

(540) 775-6555

Property at 352 North Glebe Rd, Montross, VA 22520, 3 beds, 2 baths

$329,900

3 beds2 baths1,258 sq ft

352 North Glebe Rd, Montross, VA 22520

(540) 373-2000

Property at 23192 Mountain Laurel Ln, California, MD 20619, 4 beds, 3.5 baths

$389,900

4 beds3.5 baths2,100 sq ft

23192 Mountain Laurel Ln, California, MD 20619

(301) 609-9000

Property at 23116 Foxglove Way, California, MD 20619, 3 beds, 3 baths

$349,900

3 beds3 baths1,640 sq ft

23116 Foxglove Way, California, MD 20619

(240) 925-2224

Property at 23134 Marble Way, California, MD 20619, 2 beds, 2 baths

$425,000

2 beds2 baths1,905 sq ft

23134 Marble Way, California, MD 20619

(443) 771-8009

Property at 23080 Vanda Way, California, MD 20619, 4 beds, 3.5 baths

$440,000

4 beds3.5 baths2,220 sq ft

23080 Vanda Way, California, MD 20619

(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 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 45455 Concord Way, California, MD 20619, 4 beds, 3.5 baths

$445,000

4 beds3.5 baths2,766 sq ft

45455 Concord Way, California, MD 20619

(888) 860-7369

Homes with Pools for Sale in Leonardtown

There are currently 20 homes with pools 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 39 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, 10 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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