Pending Listings in 20627, MD

18 homes

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UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 20627, MD:
Charming Home in Prime Leonardtown Location This inviting home sits in the heart of historic Leonardtown— a highly sought-after community with easy access to schools, the hospital, parks, restaurants, and shops. Inside, an open floor plan with abundant natural light creates a welcoming feel. A flexible main-level room works perfectly as a bedroom, office, or playroom. The separate dining room connects through a butler’s pantry to a full walk-in pantry and flows into a modern kitchen featuring granite counters, upgraded cabinetry, stylish subway tile backsplash, large center island, gas cooktop, double wall ovens, and a premium Samsung Bespoke 4-drawer refrigerator with beverage

$599,900

4 beds3.5 baths3,690 sq ft

41444 Osborne Ln, Leonardtown, MD 20650

6,600 sq ft lot • 2 garage spots • Community pool

(301) 862-2169

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 20627, MD:
Value is in the land. Unique opportunity in the heart of downtown Leonardtown. Property includes the Washington Street parcel with an additional rear parcel on Lawrence Avenue conveying, together forming an assembly of approximately one and a half acres within the Town of Leonardtown limits. Zoned within a residential district and located in an area recognized as part of Leonardtown’s Arts & Entertainment environment, this site offers flexibility for buyers with vision. Prior use history and prime location may support creative redevelopment concepts—buyers are encouraged to submit plans and ideas directly to the Town of Leonardtown for consideration. Ideal for those seekin

$599,950

— beds— baths1,691 sq ft

22615 Washington St, Leonardtown, MD 20650

Custom residence • Rare opportunity • Close to waterfront

(240) 925-2224

PENDING

ABOUT THIS HOME
Pending Listing in 20627, MD:
IMMACULATE & Impressively Upgrades 4 Bed 3.5 Bath End-Unit Townhome w/ a 2- Car Garage & a Screened in Porch in Clark's Rest! Located in the highly sought-after Clark's Rest community in the heart of Leonardtown, this beautifully maintained end-unit townhome offers the perfect blend of space, comfort, and convenience. Just minutes from historic downtown Leonardtown, Leonardtown Wharf, restaurants, boutique shopping, parks, award-winning schools, and an easy commute to NAS Patuxent River, this home combines modern living with an unbeatable location. Featuring three spacious bedrooms, two and a half bathrooms on the upper level, and a versatile lower level currently configured as

$460,000

4 beds3.5 baths2,469 sq ft

41379 Margrove Cir, Leonardtown, MD 20650

Screened in porch • Quartz countertops • Community amenities

(443) 968-9595

PENDINGVIDEO TOUR

ABOUT THIS HOME
Pending Listing in 20627, MD:
Homesite 132 TO BE BUILT 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 expansive 3095 sq ft home offers generous living areas, abundant natural light, and the perfect blend of functionality and style. Photos shown are representative and intended to illustrate a similar finished townhouse. Projected settlement August, 2026. The main level welcomes you with a finished rec room or optional 4th bedroom, complete with a full bath and access to your b

$489,900

4 beds3.5 baths3,095 sq ft

Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650

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

(443) 771-8009

PENDINGVIDEO TOUR

ABOUT THIS HOME
Pending Listing in 20627, MD:
* * * TO BE BUILT * * * * * * Estimated Late November Delivery * * * * * * Choose your color scheme from of our available options * * * Home Site 142 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 expansive 3095 sq ft home offers generous living areas, abundant natural light, and the perfect blend of functionality and style. The main level welcomes you with a finished rec room or optional 4th bedroom, complete with a full bat

$489,900

4 beds3.5 baths3,095 sq ft

Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

Finished rec room • New construction • Granite countertops

(443) 771-8009

Property at Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$479,900

4 beds3.5 baths— sq ft

Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650, 4 beds, 3.5 baths

$479,900

4 beds3.5 baths2,966 sq ft

Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 131 - 23703 Weeping Willow Way Way, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths2,554 sq ft

Lot 131 - 23703 Weeping Willow Way Way, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$487,400

4 beds3.5 baths3,095 sq ft

Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 154 - 23808 Wisteria Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$479,900

4 beds3.5 baths2,966 sq ft

Lot 154 - 23808 Wisteria Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Cedar Lane Rd, Leonardtown, MD 20650

$3,800,000

Land52.18 acres (lot)

Cedar Lane Rd, Leonardtown, MD 20650

(301) 208-2288

Property at 41614 Briarwood Cir, Leonardtown, MD 20650, 4 beds, 3.5 baths

$470,000

4 beds3.5 baths2,816 sq ft

41614 Briarwood Cir, Leonardtown, MD 20650

(301) 862-2169

Property at 25845 Point Lookout Rd, Leonardtown, MD 20650

$1,740,000

Land3.85 acres (lot)

25845 Point Lookout Rd, Leonardtown, MD 20650

(703) 753-7910

Property at Lot 130 - 23709 Weeping Willow Way, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths2,571 sq ft

Lot 130 - 23709 Weeping Willow Way, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 144 - 23635 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths2,604 sq ft

Lot 144 - 23635 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 151 - 23790 Wisteria Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$489,900

4 beds3.5 baths3,095 sq ft

Lot 151 - 23790 Wisteria Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 158 - 23646 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths2,554 sq ft

Lot 158 - 23646 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$479,900

4 beds3.5 baths2,966 sq ft

Lot 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

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UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 20627, MD:
Unlock the potential in this 4-bedroom, 2-bath handyman special located in the highly desirable Brenton Bay community of Leonardtown! Perfect for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features a functional layout with a kitchen, separate dining room, spacious living room, two bedrooms, and a full bathroom. The finished lower level expands the living space with an additional family room, two more bedrooms, and a second full bathroom—ideal for guests, a home office, or multi-generational living. With great bones and endless possibilities, this home is ready for your personal touches and updates. Fantastic locati

$359,777

4 beds2 baths2,474 sq ft

40743 Magee Dr, Leonardtown, MD 20650

Waterfront amenities • Functional layout • Finished lower level

(855) 450-0442

UNDER CONTRACTFLOOR PLAN

ABOUT THIS HOME
Pending Listing in 20627, MD:
This stunning 5 bedroom home sits gracefully at the end of a cul-de-sac on a private lane in Avenmar; a water oriented community on Breton Bay. Its elegant facade overlooks the lovely landscaped yard. From the gourmet kitchen, wander on to the custom covered rear screened porch (almost 600 sq. ft. ) where the morning sun dances across the private backyard and patio. Each spacious bedroom is filled with natural light and overlooks the lush woodland and peaceful yard. The main level welcomes you with gleaming hardwood floors that stretch throughout. Formal living and dining areas are perfect for entertaining plus a dedicated office for quiet work-time. The family room off of the kitchen featu

$989,000

5 beds5 baths5,810 sq ft

22856 White Swan Way, Leonardtown, MD 20650

High-end appliances • Private backyard • Gourmet kitchen

(703) 535-3610

Pending Listings in 20627

There are currently 18 pending listings for sale in 20627. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. This map is refreshed with the newest listings in 20627 every 15 minutes.

Find your dream home in 20627 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 20627 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 20627. If you're looking to sell your home in the 20627 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 20627 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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