Pending Listings in 20627, MD

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UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 20627, MD:
This Colonial in the sought-after Estates at Singletree offers 5 bedrooms, 3.5 baths, and three finished levels in one of Leonardtown’s most convenient locations are just behind St. Mary’s Hospital. The fully finished basement is a highlight, featuring a home theater room, a rec room, a large bedroom with a walk-in closet, and a full bath. Upstairs, you will find four additional bedrooms, including a spacious primary suite with a soaking tub, a separate shower, and double sinks. New carpet has been installed throughout this level. The main floor includes a formal living and dining room with built-ins, an office, and a large family room with a stone front fireplace and hardwood f

$580,000

5 beds3.5 baths3,575 sq ft

23261 Jenifer Ct, Leonardtown, MD 20650

0.32 acre lot • $15 HOA • 2 garage spots

(301) 855-8600

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 20627, MD:
Welcome to your coastal retreat in the highly sought-after Leonard’s Grant community in Leonardtown, MD. This beautifully updated home features fresh Sherwin Williams coastal paint, new plush carpet, crisp ivory trim, and abundant natural light throughout, creating a breezy, beach-inspired feel. The chef’s kitchen boasts granite countertops, black stainless appliances, a Bosch quiet dishwasher, and a new gas cooktop. Exterior highlights include brand-new James Hardie fiber cement siding in deep ocean blue with white shutters, a fenced backyard with garden beds, a newly refinished deck, and an automatic sprinkler system. Enjoy top-notch community amenities including a pool, tenni

$650,000

5 beds3.5 baths4,046 sq ft

41402 Silver Charm Ct, Leonardtown, MD 20650

9,100 sq ft lot • $81 HOA • 2 garage spots

(301) 298-2892

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 20627, MD:
Live in this lovely waterfront community. Enjoy Kayaking, Paddle boarding whatever your hobbies are. There is even yoga on the wharf, You can walk to weekend concerts on the square. Leonardtown is a wonderful place to live. How about an elevator? This home has one. Send your groceries up in the elevator. Send you laundry down in the elevator, 5 decks/porches to enjoy outdoor living. Walk to the community park. Everything is right where you need it in this lovely home. A must see.

$520,000

3 beds3.5 baths2,764 sq ft

22539 Landing Way, Leonardtown, MD 20650

2,638 sq ft lot • $67 HOA • 2 garage spots

(888) 860-7369

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 20627, MD:
Built in 2022, this stunning QBH Adelina floor plan shows like brand new, complete with every feature you would want if you designed it yourself. Thoughtful upgrades and stylish finishes flow throughout, making this home truly move-in ready. The main level features a 4 ft rear extension, gorgeous LVP flooring, and timeless trim details including crown molding, shadow boxes, and a full front door trim package. A designated office with glass doors is the perfect work-from-home space, while the dining room offers a classic setting for gatherings. The grand kitchen is a showstopper with a pot filler, tile backsplash, stunning quartz countertops, stainless steel appliances, and a charming built-

$685,000

5 beds3.5 baths3,642 sq ft

23098 Town Run Dr, Leonardtown, MD 20650

9,226 sq ft lot • $45 HOA • 2 garage spots

(301) 702-4200

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 20627, MD:
Welcome home to 41535 Singletree Dr. This beautiful colonial offers 4 bedrooms and 2.5 baths with laminate hardwood floors throughout the first level. New carpet has been installed throughout the second level. The kitchen features quartz countertops and opens to a living room with a cozy gas fireplace, as well as a formal dining room and sitting area, perfect for gatherings and everyday living. Upstairs, you’ll find four spacious bedrooms, while outside, a level lot and deck provide space for cooking out and private entertaining. Located within walking distance to Leonardtown’s shops, restaurants, waterfront, and hospital, and served by sought-after Leonardtown schools. This pro

$530,000

4 beds2.5 baths2,262 sq ft

41535 Singletree Dr, Leonardtown, MD 20650

0.26 acre lot • $33 HOA • 2 garage spots

(301) 684-4895

Property at 41536 Fairwood Ct, Leonardtown, MD 20650, 4 beds, 3.5 baths

$569,000

4 beds3.5 baths3,308 sq ft

41536 Fairwood Ct, Leonardtown, MD 20650

(301) 843-5100

Property at 25845 Point Lookout Rd, Leonardtown, MD 20650

$1,740,000

— beds— baths— sq ft

25845 Point Lookout Rd, Leonardtown, MD 20650

(703) 753-7910

Property at Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$445,900

4 beds3.5 baths— sq ft

Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at 41650 Matthew Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$520,000

4 beds2.5 baths2,230 sq ft

41650 Matthew Ct, Leonardtown, MD 20650

(301) 862-0008

Property at Lot 92-23700 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$445,900

4 beds3.5 baths— sq ft

Lot 92-23700 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at 23534 Belmar Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$639,000

5 beds3.5 baths4,738 sq ft

23534 Belmar Dr, Leonardtown, MD 20650

(301) 862-2169

Property at Lot 91-23694 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$445,900

4 beds3.5 baths— sq ft

Lot 91-23694 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$469,900

4 beds3.5 baths2,966 sq ft

Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at 41435 Osborne Ln, Leonardtown, MD 20650, 6 beds, 4.5 baths

$665,000

6 beds4.5 baths4,145 sq ft

41435 Osborne Ln, Leonardtown, MD 20650

(301) 702-4200

Property at Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$479,900

4 beds3.5 baths— sq ft

Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 97-23730 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$469,900

4 beds3.5 baths— sq ft

Lot 97-23730 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$447,400

4 beds3.5 baths2,604 sq ft

Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 90 - 23688 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$469,900

4 beds3.5 baths— sq ft

Lot 90 - 23688 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Cedar Lane Rd, Leonardtown, MD 20650

$3,800,000

— beds— baths— sq ft

Cedar Lane Rd, Leonardtown, MD 20650

(301) 862-2169

Property at Lot 94 - 23712 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$479,900

4 beds3.5 baths— sq ft

Lot 94 - 23712 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

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UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in 20627, MD:
BACK ON THE MARKET!! Get it while you can!! Charming Home with a Rare Double Lot in Society Hill, Leonardtown, MD Seller is wiling to Offer Some Seller Paid Closing Help! Nestled in the desirable Society Hill neighborhood of Leonardtown, this one-of-a-kind property offers a rare opportunity with its expansive double lot—a true gem in the community. While the home retains a timeless charm, it presents an exciting chance to add your personal touch and modern updates. Inside, you'll find character-filled spaces, including spacious living areas, and an inviting layout that exudes warmth. The home’s unique charm shines through in its craftsmanship, offering a perfect blend of nost

$429,900

3 beds3 baths2,028 sq ft

22362 Armstrong Dr, Leonardtown, MD 20650

1.06 acre lot • 2 garage spots • Community pool

(301) 862-2169

PENDING

ABOUT THIS HOME
Pending Listing in 20627, MD:
Welcome to your ideal home in the sought-after Hanover at Breton Bay! This beautiful, spacious home shines with thoughtful design, featuring hardwood floors that flow through a bright, open-concept layout and a striking two-story foyer. The well-appointed kitchen is a cook’s dream, with ample cabinetry, generous countertops, a spacious center island, and a cozy breakfast nook, effortlessly connecting to a warm family room with a gas fireplace and large windows that invite natural light. The elegant dining room, accented with crown molding, sets the stage for memorable gatherings. On the main level there is also flex room with an attached full bath serves as a perfect guest bedroom or

$639,900

4 beds3 baths3,404 sq ft

22305 Hanover Dr, Leonardtown, MD 20650

0.56 acre lot • $50 HOA • 3 garage spots

(301) 862-2169

PENDING

ABOUT THIS HOME
Pending Listing in 20627, MD:
The LAST BUILDING SITE in Avenmar! You won't want to miss this opportunity to purchase the last builder developed parcel in one of Leonardtown's most sought after communities! With over 3.5 wooded acres, this property offers a flat, private, wooded setting like no other. Community features pier, boat ramp, stables, pool, community center and so much more! Contact us for more info, or to set up a private tour, today! This sale is offered in tandem with 40801 Kiskadee Ln (seller prefers to sell both properties together). * The building site (and future home) is located off of the private street Kiskadee Ln *

$200,000

— beds— baths— sq ft

Kiskadee Ln, Leonardtown, MD 20650

3.53 acre lot • $200 HOA • Car-dependent

(410) 535-6291

Pending Listings in 20627

There are currently 20 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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