4 Bedroom 2 Bath homes for sale & real estate in Leonardtown, MD

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ABOUT THIS HOME
4 Bedroom 2 Bath Homes for Sale in Leonardtown, MD
Nestled within one of the most desirable subdivisions, this classic two-story Colonial welcomes you home with charm and a sense of privacy on two wooded acres Step inside and feel the warmth of meticulously cared-for details : gleaming hardwood floors through the main level, a spacious separate dining room into a beautifully updated kitchen. Corian countertops, stainless steel appliances, and center island make it a joy to cook and gather Kitchen opens into a cozy family room anchored by a wood-burning fireplace and a light-filled sunroom with lots of windows inviting the outside in. Connecting deck overlooking your own peaceful woods Upstairs, four generous bedrooms offer restful retr

$574,900

4 beds2.5 baths2,594 sq ft

20753 Chestnut Ridge Dr, Leonardtown, MD 20650

2 acre lot • 2 garage spots • Built 1994

(301) 862-2169

ABOUT THIS HOME
4 Bedroom 2 Bath Homes for Sale in Leonardtown, MD
COMING SOON! Beautiful 4 bedroom, 2 1/2 bathroom colonial on over half an acre lot in Breton Bay! This home has has everything you could want with formal living & dining rooms, kitchen w/ upgraded counter tops and appliances. The kitchen has bar style seating, a breakfast nook with built in bench and a seating area perfect for morning coffee and enjoying views of the back yard and pool. The back yard is landscaped with various flowering plants & bushes. The salt water pool provides endless opportunities to relax and entertain in this outdoor oasis. The entire yard has 6 ft. vinyl fencing and ample storage with several sheds. Close to schools, shopping, and area amenities. Jus

$550,000

4 beds2.5 baths2,328 sq ft

22338 White Oak Rd, Leonardtown, MD 20650

0.66 acre lot • 2 garage spots • Pool

(301) 862-2169

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ABOUT THIS HOME
4 Bedroom 2 Bath Homes for Sale in Leonardtown, MD
Classic Private Colonial offers the perfect blend of tranquility and convenience, nestled on a generous 1.25-acre lot that backs to mature trees for ultimate shade and privacy. Outdoor Living: Enjoy entertaining or quiet mornings on the large vinyl deck, overlooking a great yard. The circular paved driveway provides easy access and added convenience. The Home: Featuring a traditional layout, you can enter through the covered front porch or the attached 2-car garage that features plenty of built-in shelves. The main level is designed for living with a family room, kitchen, a separate dining room, and a cozy living room with a gas fireplace. A half bath on the main level adds convenience. Pri

$520,000

4 beds2.5 baths1,920 sq ft

42611 Wilderness Rd, Leonardtown, MD 20650

1.25 acre lot • 2 garage spots • Built 1997

(443) 771-8009

ABOUT THIS HOME
4 Bedroom 2 Bath Homes for Sale in Leonardtown, MD
Welcome to 21920 Newtowne Neck Road! Step inside this inviting Colonial home offering 2,291 sq. ft. of comfortable living space, 4 bedrooms, and 2.5 bathrooms, perfectly situated on a . 55-acre lot in Leonardtown. Inside, you’ll find a bright and spacious layout designed for both everyday living and entertaining. The heart of the home features an eat-in kitchen with stainless steel appliances, a center island, and plenty of natural light, opening to a warm and welcoming family room. Step right out onto the deck off the kitchen, ideal for morning coffee, grilling, or hosting gatherings that flow easily into the fenced backyard. Upstairs, the generously sized bedrooms include a relaxing

$510,000

4 beds2.5 baths2,291 sq ft

21920 Newtowne Neck Rd, Leonardtown, MD 20650

Deck off the kitchen • Primary suite • Eat-in kitchen

(443) 771-8009

ABOUT THIS HOME
4 Bedroom 2 Bath Homes for Sale in Leonardtown, MD
Beautiful colonial home in the Meadows of Town Run neighborhood in Leonardtown. This home has large 6 ft. windows on the entire main level to allow tons of natural light! A beautiful front porch is a great place to sit and chat with your neighbors and enjoy the peaceful community. The upstairs has 4 large bedrooms, the laundry room, and two bathrooms. The main bedroom suite features a large walk-in closet and a luxury bathroom featuring a soaking tub, huge shower, and two vanities featuring gorgeous decorative tile. The kitchen and family room on the main floor offer a large welcoming space for family and friends with a sliding glass door that goes out to the patio to enjoy the firepit and

$655,000

4 beds2.5 baths2,888 sq ft

43018 Bluejay Ln, Leonardtown, MD 20650

Large windows • Main bedroom suite • Walk-in closet

(443) 771-8009

Property at Undisclosed address, Leonardtown, MD 20650, 4 beds, 2 baths

$1,750,000

4 beds2 baths2,130 sq ft

Undisclosed address, Leonardtown, MD 20650

(301) 686-0545

Property at 40533 Breton Knolls Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$859,900

4 beds2.5 baths— sq ft

40533 Breton Knolls Ct, Leonardtown, MD 20650

(301) 843-5100

Property at 42520 Riverwinds Dr, Leonardtown, MD 20650, 4 beds, 2 baths

$1,999,999

4 beds2 baths2,744 sq ft

42520 Riverwinds Dr, Leonardtown, MD 20650

(301) 862-2169

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COMING SOON

ABOUT THIS HOME
4 Bedroom 2 Bath Homes for Sale in Leonardtown, MD
Welcome to 44913 Widgeon Place, a beautifully maintained colonial tucked away on a quiet cul-de-sac just minutes from Naval Air Station Patuxent River. This home delivers the best of Southern Maryland living, surrounded by the Patuxent and Potomac Rivers with convenient access to the Chesapeake Bay. The charming front porch sets the stage, offering a warm welcome and the perfect place to relax and take in the peaceful surroundings. Inside, the home opens to gleaming hardwood floors, an elegant staircase, and an airy layout designed for comfort and flow. The spacious kitchen offers gently used appliances, ample counter space, and a pantry ideal for everyday cooking and entertaining. The adjo

$469,900

4 beds2.5 baths2,430 sq ft

44913 Widgeon Pl, Callaway, MD 20620

0.24 acre lot • 2 garage spots • Built 2000

(301) 843-5100

COMING SOON

$279,999

4 beds2.5 baths1,693 sq ft

20801 Harlequin Ln, Callaway, MD 20620

$33 HOA • Built 1987 • Listed 4 days

(888) 889-5764

ABOUT THIS HOME
4 Bedroom 2 Bath Homes for Sale in Leonardtown, MD
Welcome to this beautifully renovated 4-bedroom, 2-bath home offering 1,400 sq. ft. of comfortable one-level living. Step inside to an inviting open-concept layout, centered around a stunning oversized kitchen island that can easily seat up to 12 guests—perfect for gatherings, meals, and entertaining. The spacious living room features floor-to-ceiling bay windows, flooding the space with natural light and creating the perfect spot for this year’s Christmas tree. You'll also enjoy the new, stylish modern fireplace, adding warmth and charm on chilly nights. The kitchen showcases stainless steel appliances, an oversized stainless sink, and fresh modern finishes designed to impress

$308,999

4 beds2 baths1,400 sq ft

45851 N Poteat Ct, California, MD 20619

8,200 sq ft lot • Built 1989 • Listed 9 days

(301) 862-4000

ABOUT THIS HOME
4 Bedroom 2 Bath Homes for Sale in Leonardtown, MD
OPEN HOUSE, SUNDAY 11/23 12pm-2pm Welcome home to this beautifully maintained property that truly shows pride of ownership at every turn. Step inside to find thoughtful updates throughout, including brand-new carpet, gleaming hardwood and porcelain floors, and a spacious, inviting layout perfect for both relaxing and entertaining. The kitchen is the heart of this home, showcasing rich cherry cabinetry, granite countertops, stainless steel appliances, and under-cabinet lighting that highlights every detail. Whether hosting a dinner or enjoying a quiet meal, this space blends style and function effortlessly. The cozy family room with a wood-burning fireplace is perfect for chilly evenings, w

$449,000

4 beds2.5 baths2,072 sq ft

23272 Hickory Hollow Ln, California, MD 20619

0.24 acre lot • 2 garage spots • Built 1990

(443) 771-8009

ABOUT THIS HOME
4 Bedroom 2 Bath Homes for Sale in Leonardtown, MD
Tucked away at the end of a quiet cul-de-sac in the Greenview Knolls neighborhood, this spacious four-level split-level home offers both character and convenience—with no HOA! Featuring four bedrooms and two and one half baths, the home provides a comfortable layout with room for everyone. The main level showcases hardwood flooring, a welcoming foyer, a formal living room with a wood-burning fireplace (utensils convey), a separate dining room, and a bright eat-in kitchen that was beautifully replaced in 2021. A sliding glass door leads to a large rear deck—newly replaced in 2025—perfect for outdoor entertaining. Upstairs, the primary bedroom includes a private ensuite bath

$399,000

4 beds2.5 baths2,662 sq ft

45869 Belvoir Rd, Great Mills, MD 20634

0.47 acre lot • Garage • Built 1968

(410) 394-0990

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ABOUT THIS HOME
4 Bedroom 2 Bath Homes for Sale 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 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 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 21312 Fox Wood Ln, California, MD 20619, 4 beds, 2.5 baths

$500,000

4 beds2.5 baths2,360 sq ft

21312 Fox Wood Ln, California, MD 20619

(301) 298-2892

Property at 924 Blackbeard Pond Rd, Hague, VA 22469, 4 beds, 2 baths

$850,000

4 beds2 baths1,900 sq ft

924 Blackbeard Pond Rd, Hague, VA 22469

(540) 299-6001

Property at 78 Cypress Dr, Montross, VA 22520, 4 beds, 2.5 baths

$424,900

4 beds2.5 baths2,400 sq ft

78 Cypress Dr, Montross, VA 22520

(540) 371-5220

Property at 826 S Glebe Rd, Montross, VA 22520, 4 beds, 2 baths

$315,000

4 beds2 baths1,536 sq ft

826 S Glebe Rd, Montross, VA 22520

(540) 373-2000

Property at 17490 Lighthouse Commons Dr, Piney Point, MD 20674, 4 beds, 2.5 baths

$559,900

4 beds2.5 baths2,400 sq ft

17490 Lighthouse Commons Dr, Piney Point, MD 20674

(301) 862-2169

Property at Lot 42 S Glebe Rd, Montross, VA 22520, 4 beds, 2.5 baths

$384,900

4 beds2.5 baths2,200 sq ft

Lot 42 S Glebe Rd, Montross, VA 22520

(540) 371-5220

Property at Lot 8 Royal Way, Montross, VA 22520, 4 beds, 2.5 baths

$399,900

4 beds2.5 baths2,250 sq ft

Lot 8 Royal Way, Montross, VA 22520

(540) 371-5220

4 Bedroom 2 Bath Homes for Sale in Leonardtown

There are currently 8 4 bedroom 2 bath homes 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, 13 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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