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St Marys County MD Homes for Sale

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  • /33

    $699,900

    • 5 Beds
    • 3.5 Baths
    • 4,080 Sq Ft

    21345 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21345 Fairwood Court! Back active after brief weather -related pause. Showings now available. Thoughtfully updated and meticulously maintained, this move-in-ready home in the desirable Leonardtown Farms community offers space, layout, and functionality. With 5 bedrooms on the upper level, 3.5 bathrooms, and generous living spaces on every level, there is room to grow, gather, and truly

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    (227) 230-5835

    21345 Fairwood Ct, Leonardtown, MD 20650
  • /14

    $184,000

    • 1 Bed
    • 1.5 Baths
    • 879 Sq Ft

    45521 Westmeath Way Unit 12, Great Mills, MD 20634

    Beautiful First-Floor Condo Offering Comfort, Convenience, and Low-Maintenance LivingDiscover the perfect blend of comfort, style, and easy living in this beautifully maintained first-floor condo. Featuring 1 bedroom, 1.5 baths, and 879 square feet, this home is designed for simplicity and function without sacrificing modern appeal.Step through the secure entryway into a bright,

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    Danielle Sloan

    JPAR Real Estate Professionals

    (240) 628-6899

    45521 Westmeath Way Unit 12, Great Mills, MD 20634
  • /35

    $565,000

    • 4 Beds
    • 3 Baths
    • 2,704 Sq Ft

    38310 Pleasant View Dr, Charlotte Hall, MD 20622

    Welcome to this unique opportunity in a well-established neighborhood, where privacy and potential meet! This home offers a new roof, siding, shutters, & gutters with plenty of space between neighbors and sits on an expansive 3.8 acres, & includes the adjoining 3.5-acre lot next door.The home itself could truly shine with a little cosmetic updating, making it a perfect fit for buyers looking

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    Jimmy Hayden

    RE/MAX One

    (227) 240-6072

    38310 Pleasant View Dr, Charlotte Hall, MD 20622
  • /9

    $800,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 3,744 Sq Ft

    23660 Pine View Ln, Hollywood, MD 20636

    This property is located in a rapidly developing area of central St. Mary’s County very close to the expanding county airport, offering strong potential for future growth and investment.The parcel is currently zoned RL (Residential Low Density), which allows for one dwelling unit per acre, with the potential for up to five homes per acre under the current zoning ordinance. Additionally,

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    Jimmy Hayden

    RE/MAX One

    (227) 230-6304

    23660 Pine View Ln, Hollywood, MD 20636
  • /2

    $25,000

    • Land
    • 0.25 Acre
    • $100,000 per Acre

    0 Sunset Dr, Chaptico, MD 20621

    Mills Point Perfection! Looking for a lot in a water access community? Take a look at this flat, mostly cleared lot in desirable Mills Point in Southern Maryland. Buyer to perform all due diligence.

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    Stephanie Rivers

    The Southside Group Real Estate

    (227) 274-0438

    0 Sunset Dr, Chaptico, MD 20621
  • /44

    $415,000

    • 4 Beds
    • 4 Baths
    • 2,290 Sq Ft

    23771 Myrtle Glen Way, California, MD 20619

    *Full home inspection performed and available to buyers upon request.* Step inside to an impressive open-concept living space, perfect for both entertaining and relaxing. On the main floor, a versatile room awaits—ideal as a private office or guest suite, complete with its own rear entry. Upstairs, soaring ceilings frame a chef-inspired kitchen that flows seamlessly into the family room, with

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    Amy Scott

    OE Realty

    (240) 589-5172

    23771 Myrtle Glen Way, California, MD 20619
  • /33

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,872 Sq Ft

    21364 Sundew Place, Lexington Park, MD 20653

    House is priced to sell! Welcome to Southwoods! Tucked away on a quiet cul-de-sac, this newly painted 3-bedroom, 2.5-bath Colonial offers the perfect blend of comfort and convenience. Features include a spacious kitchen with granite counters, lots of cabinets, Pantry and large island, new LVP flooring installed in select rooms, and a relaxing deck that backs to woods—your own private retreat. The

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    Michele Hagan

    CENTURY 21 New Millennium

    (240) 617-4266

    21364 Sundew Place, Lexington Park, MD 20653
  • /15

    $25,000

    • Land
    • 0.92 Acre
    • $27,174 per Acre

    0 Lake Dr Unit MDSM2028612, Scotland, MD 20687

    Almost 1 acre of raw, wooded land. Use for recreational purposes or contact the county about a perc to build a house. This property includes community beach access on the Chesapeake Bay and is a short distance from Point Lookout State Park Seller financing available.

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    Sarah Swann

    Baldus Real Estate, Inc.

    (240) 244-4643

    0 Lake Dr Unit MDSM2028612, Scotland, MD 20687
  • /61

    $679,900

    • 2 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    40461 Old Breton Beach Rd, Leonardtown, MD 20650

    Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with a loft on the Potomac River just minutes from historic Leonardtown. Perfectly designed for those who love life on the water, this property features its own private dock complete with a boat lift and fish cleaning station, making it a dream come true for boaters and anglers alike.Inside, you’ll find a

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    Mileah Walker

    Real Broker, LLC

    (227) 240-6440

    40461 Old Breton Beach Rd, Leonardtown, MD 20650
  • /2

    $275,000

    • Land
    • 72.84 Acres
    • $3,775 per Acre

    0 Greens Crossing Way, Great Mills, MD 20634

    73.30 total acres consisting of 2 lots. All wooded. Great for hunting or exploring nature as it gets very close to the St. Mary's River. This is an Open Space parcel so no building permitted. Great price for a LOT of land.

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    Jimmy Hayden

    RE/MAX One

    (240) 262-0566

    0 Greens Crossing Way, Great Mills, MD 20634
  • /43

    $874,900

    • 6 Beds
    • 3 Baths
    • 2,683 Sq Ft

    17203 Piney Point Rd, Piney Point, MD 20674

    The current owners have lovingly maintained this home as their second residence, and it truly shows! Inside, you’ll find formal living and dining rooms, an updated eat-in kitchen with a center island, quartz countertops, and stainless steel appliances. The living room features a cozy wood-burning fireplace, and a great sunroom overlooks the Potomac River.Natural hardwood floors run throughout

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    DANNY LEUNG

    Century 21 Redwood Realty

    (240) 896-5594

    17203 Piney Point Rd, Piney Point, MD 20674
  • /18

    $589,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 2,184 Sq Ft

    43641 Redmond Rd, Leonardtown, MD 20650

    This great 8+ acre property with scenic pasture views. Solid 4 bedroom rambler on full basement. So many possibilities.

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    Jimmy Hayden

    RE/MAX One

    (227) 231-3115

    43641 Redmond Rd, Leonardtown, MD 20650
  • /36

    $299,900

    • 1 Bed
    • 1.5 Baths
    • 1,645 Sq Ft

    44140 Outrigger Way, California, MD 20619

    Step into modern comfort with this beautifully designed 1-bedroom, 1.5-bath condo, featuring an open-concept layout and high-end finishes throughout. The spacious living room boasts dramatic vaulted ceilings, creating a light-filled and airy space perfect for relaxing or hosting. A convenient half bath adds functionality for guests. The impressive kitchen is a true showpiece, complete with

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    Connie Gunn

    CENTURY 21 New Millennium

    (240) 213-7707

    44140 Outrigger Way, California, MD 20619
  • /47

    $825,000

    • 3 Beds
    • 2.5 Baths
    • 2,591 Sq Ft

    38884 Collinwood Dr, Abell, MD 20606

    Stunning Waterfront Rambler! Move-In Ready! Experience the charm of coastal living in this beautifully renovated all-brick rambler perfectly situated on 1.19 acres with 262 feet of waterfront! From sunrise to sunset, enjoy 360-degree panoramic water views in a peaceful, private setting surrounded by mature trees and wildlife. Step inside to discover 3 spacious bedrooms, updated 2.5 bathrooms, and

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    Connie Fitzgerald

    RE/MAX One

    (227) 232-4482

    38884 Collinwood Dr, Abell, MD 20606
  • /55

    $430,000

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft

    23084 Vanda Way, California, MD 20619

    Townhome located in the Orchid Park Neighborhood of the highly desirable Wildewood community! This home offers an abundance of upgrades including recessed lighting throughout; upgraded lighting in all bedrooms, LVP flooring on entry and main levels, upgraded carpet on upper level; gourmet kitchen with upgraded cabinetry, under cabinet lighting, quartz countertops, gas range, double oven, and

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    Edward Tully

    RE/MAX One

    (301) 507-1977

    23084 Vanda Way, California, MD 20619
  • /30

    $425,000

    • 3 Beds
    • 3 Baths
    • 1,304 Sq Ft

    45227 Nats Creek Rd, Hollywood, MD 20636

    Estate Sale – Being Sold As-Is. Welcome to this charming all-brick rambler offering 3 bedrooms and 3 full baths, beautifully situated along Nats Creek. Priced below assessed value, this is an exceptional opportunity to enjoy peaceful waterfront living where mornings begin with water views and evenings are perfect for unwinding in a serene natural setting. The open kitchen is ideal for gathering

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    Connie Fitzgerald

    RE/MAX One

    (227) 231-0887

    45227 Nats Creek Rd, Hollywood, MD 20636
  • /48

    $449,000

    • 4 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    23272 Hickory Hollow Ln, California, MD 20619

    Back on the market, through no fault of the sellers! 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,

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    Deanna Rothstein

    RE/MAX One

    (240) 237-9515

    23272 Hickory Hollow Ln, California, MD 20619
  • /16

    $100,000

    • Land
    • 1.26 Acres
    • $79,365 per Acre

    22453 Macarthur Blvd, California, MD 20619

    Discover the perfect canvas for your next home on this pristine, level 1+ acre parcel. Thoughtfully center your home to quick and accessible amenities in the county. This buildable lot offers a rare combination of natural beauty and modern convenience. Fruit trees were planted just a couple of years ago, (9 apple trees, varying types and 2 mature plum trees) This can add charm and the promise of

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    Connie Gunn

    CENTURY 21 New Millennium

    (240) 262-3802

    22453 Macarthur Blvd, California, MD 20619
  • /3

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,456 Sq Ft

    22685 Maddox Rd, Bushwood, MD 20618

    A perfect opportunity for buyers looking to build equity while making a home their own. This solid, well-maintained home features a newer roof and an upgraded heat pump system with central air. Set on a spacious, level lot, the heavy lifting is already done—just bring your vision and style. A great chance to turn good bones into something truly special.

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    Connie Gunn

    CENTURY 21 New Millennium

    (227) 238-2455

    22685 Maddox Rd, Bushwood, MD 20618
  • /42

    $615,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    38819 Morris Point Rd, Abell, MD 20606

    Wake to a beautiful sun rise and doze to a beautiful sunset. Beautiful 3BR/2BA one-level waterfront home with boathouse, 6’x40’ pier w/ boat lift, and newer bulkhead with 6’ MLW. Enjoy an all-season sunroom with water views, brand new roof, newer windows, and updated systems including a 6-yr HVAC, new washer/dryer, and microwave. Two sheds provide extra storage. Primary bedroom has private

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    Jimmy Hayden

    RE/MAX One

    (227) 229-2593

    38819 Morris Point Rd, Abell, MD 20606
  • /48

    $520,000

    • 3 Beds
    • 3.5 Baths
    • 2,764 Sq Ft

    22547 Landing Way, Leonardtown, MD 20650

    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

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    Trish Brow

    EXP Realty, LLC

    (227) 230-5778

    22547 Landing Way, Leonardtown, MD 20650
  • /21

    $379,900 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,348 Sq Ft

    46783 Bryan Rd, Lexington Park, MD 20653

    Main level primary suite in this beauty. Plus 2 more good size bedrooms on 2nd level. 2.5 baths with a finished walkout basement with waterproof LVP flooring and huge laundry room. Freshly painted, newer stainless appliances, and newer ceiling fans (5). Large fenced in back yard with a shed plus a quaint front porch. This home is conveniently located minutes from shopping, Pax River, Exploration

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    Jimmy Hayden

    RE/MAX One

    (240) 608-6964

    46783 Bryan Rd, Lexington Park, MD 20653
  • /2

    $499,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,631 Sq Ft

    24931 Sotterley Rd, Hollywood, MD 20636

    TO BE BUILT. Brand New Construction. NO School Excise Tax! Floor Plans to be uploaded soon. Plans to break ground Jan/Feb 2026 with a projected completion date of June/Aug 2026 or sooner. Front of the home will showcase Board & Batten vinyl siding, black framed Double-Hung, Low-E windows, a 6x24' covered front porch with black metal roofing. Rear and sides of the home with Vinyl Lap Siding and

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    Sandi Foraci

    RE/MAX One

    (227) 234-0860

    24931 Sotterley Rd, Hollywood, MD 20636
  • /68

    $779,900

    • 4 Beds
    • 4 Baths
    • 2,097 Sq Ft

    22393 Saint Clements Ave, Leonardtown, MD 20650

    Experience refined waterfront living in this completely renovated rancher overlooking Saint Clements Bay. Originally built in 1966, this residence has been thoughtfully reimagined from top to bottom with extensive structural, electrical, and plumbing upgrades, blending modern luxury with effortless coastal charm. Situated on a waterfront lot, the property offers its own private L-shaped

    Ralph Harvey ListWithFreedom.com

    22393 Saint Clements Ave, Leonardtown, MD 20650
  • /55

    $900,000

    • 3 Beds
    • 2.5 Baths
    • 3,021 Sq Ft

    48800 Spring Ridge Rd, Lexington Park, MD 20653

    Start 2026 exactly the way you deserve—by making this extraordinary all-brick modern Tudor your own. Tucked behind a private gated drive, this nearly 21⁄2-acre retreat immediately sets the tone for a life of serenity, privacy, and refined coastal living. As you arrive, the escape begins: a sparkling pool welcomes you home, while a tranquil inland pond—shaped by the gentle tides of the Chesapeake

    Dorothy Bistransin Redfin Corp

    48800 Spring Ridge Rd, Lexington Park, MD 20653
  • /38

    $489,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,169 Sq Ft

    23175 Whistlewood Ln, California, MD 20619

    Details coming soon — you won’t want to miss this beautiful home!

    Rich Thomas Redfin Corp

    23175 Whistlewood Ln, California, MD 20619
  • /20

    $249,000

    • Land
    • 1 Acre
    • $249,000 per Acre

    25895 Point Lookout Rd, Leonardtown, MD 20650

    Position your business for success with this 1.00-acre commercial lot in Leonardtown, MD, zoned Commercial Highway (C-H). Located next to PNC Bank and across from a storage facility, this property boasts great visibility and easy access, making it ideal for a variety of commercial uses.Zoning allows for flexible development options such as: Retail and Business Establishments

    Krista Depenthal Lands2Love

    25895 Point Lookout Rd, Leonardtown, MD 20650
  • /11

    $485,500

    • 4 Beds
    • 2 Baths
    • 1,456 Sq Ft

    40265 Beach Dr, Mechanicsville, MD 20659

    Time to enjoy the beautiful views of this 4 Bedroom 2 Bath rambler that has a 2 car garage. HUD MAKES NO REPAIRS. HUD CASE#241-931775). EQUAL HOUSING OPPORTUNITY. GROUND RENT/HOA/CONDO FEES/FF Fees if any to be verified by purchaser. All offers submitted to HUDHOMESTORE for bid status and availability visit HUDHOMESTORE.

    Christopher White Classic Select Inc

    40265 Beach Dr, Mechanicsville, MD 20659
  • /35

    $430,000

    • 3 Beds
    • 3.5 Baths
    • 2,548 Sq Ft

    45429 Englewood Way, California, MD 20619

    Luxury Living in Style describes this stunning end unit townhome with 2,548 finished sq ft in a premium location close to schools, shopping, restaurants and commuter routes in California, Maryland. This beautifully maintained 3-level end-unit of superb living space including a fully finished basement. With 3 spacious bedrooms, 3 full bathrooms, and a convenient half bath, there’s room for

    Mary Chambers JPAR Real Estate Professionals

    45429 Englewood Way, California, MD 20619
  • /30

    $479,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650

    Homesite 102 Oakley D1***March Delivery***Builder Incentive $12,500 in Closing Help with use of preferred lender and title company. New Construction – Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown,

    Laura Bernth RE/MAX One

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
  • /52

    $595,000

    • 5 Beds
    • 3.5 Baths
    • 3,526 Sq Ft

    21117 Catnip Ct, Leonardtown, MD 20650

    Seller is offering a $4,000 concession with an accepted full-price offer!Use it for an interest-rate buy-down, closing costs, or to add your own personal touches. Get ready to fall in love with this wonderful 5BR/3.5BA home in the Leonardtown's Kingston Estates! Set on a peaceful, no-through street and perched on a gentle hill, this home offers great privacy with mature trees and plenty of

    Melissa Rodriguez RE/MAX One

    21117 Catnip Ct, Leonardtown, MD 20650
  • /9

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,150 Sq Ft

    26188 Skyview Dr, Hollywood, MD 20636

    JUST REDUCED WHAT A DEAL = HOME NEEDS SOME WORK = VACANT = WATERFRONT ON COLES CREEK. SELLER WILL PAY $40,000.00 TOWARD HOME IMPROVEMENTS IF SETTLEMENT CAN BE WITHIN 30 DAYS.

    Glen Elrod Elrod & Associates Real Estate, Inc

    26188 Skyview Dr, Hollywood, MD 20636
  • /30

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,600 Sq Ft

    38624 Woodwind Way, Mechanicsville, MD 20659

    Private single family home in great condition with 2600 square feet of living space, nestled on 15 acres of wooded land (.5 acres cleared) located in a small development with a paved driveway. - 3 Bedrooms (Master BR with en suite full bath)- 2 Full bathrooms- Large laundry room, kitchen and family room- Full walkout basement (half finished with 9 foot ceilings)- Artisan well

    Thomas Hennerty NetRealtyNow.com, LLC

    38624 Woodwind Way, Mechanicsville, MD 20659
  • /71

    $580,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 2,940 Sq Ft

    23593 Mitchell Dr, Leonardtown, MD 20650

    Welcome to your new home! This impressive 5-bedroom, 3.5-bathroom residence is a masterpiece of design, offering a spacious and well-thought-out layout. Nestled in a prime location with access to top-rated schools, this property caters to both practicality and beauty. Both HVAC systems have been replaced, roof is only 5 years old, new paint throughout and a new BEAUTIFUL patio!!Key Features:

    Heather Foster RE/MAX One

    23593 Mitchell Dr, Leonardtown, MD 20650
  • /89

    $650,000

    • 4 Beds
    • 2.5 Baths
    • 2,632 Sq Ft

    27245 Cat Creek Rd, Mechanicsville, MD 20659

    Here's your opportunity to own a water-oriented property!!! Just off the Patuxent River located on Cat Creek that offers a peaceful, natural setting surrounded by a tranquility. While the creek is not visible from the home, the property includes direct water access with a private pier, making it ideal for kayaking, nature watching, sipping a warm or cold beverage and enjoying the waterfront

    Tina Marie Biggs EXP Realty, LLC

    27245 Cat Creek Rd, Mechanicsville, MD 20659
  • /45

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650

    Homesite 100 Madison D1: ***March Delivery***Builder Incentive $12,500 in Closing Help with use of Preferred Lender & Title. Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 sq ft of beautifully finished living space. This interior unit features an

    Laura Bernth RE/MAX One

    Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650
  • /4

    $690,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 4,180 Sq Ft

    41438 Silver Charm Ct, Leonardtown, MD 20650

    Heather Foster RE/MAX One

    41438 Silver Charm Ct, Leonardtown, MD 20650
  • /29

    $599,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    20260 Hawks Way, Leonardtown, MD 20650

    IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and

    Mark Frisco CENTURY 21 New Millennium

    20260 Hawks Way, Leonardtown, MD 20650
  • /62

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 2,540 Sq Ft

    48836 Park Pines Dr, Lexington Park, MD 20653

    Well maintained and thoughtfully prepared for the market, this home sits on nearly 2.5 private, wooded acres with exceptional outdoor living. The backyard features a custom greenhouse, fenced raised-bed gardens, chicken coop, a small storage shed, and a large shed with electric service. A wraparound composite deck is wired for a hot tub and includes a fire pit and screened enclosure—ideal for

    Heather Foster RE/MAX One

    48836 Park Pines Dr, Lexington Park, MD 20653
  • /35

    $470,000

    • 4 Beds
    • 2.5 Baths
    • 2,147 Sq Ft

    23104 Sweetbay Ln, California, MD 20619

    Updated 4-bedroom, 2.5-bath home on a tree-lined corner lot in the desirable Wildewood community. Custom interior shutters, new luxury vinyl flooring, and thoughtful design details elevate the home, including a geometric accent wall, hand-stenciled half bath, and a board-and-batten feature wall in the primary suite. The floor plan offers an easy, natural flow with a kitchen that includes table

    Colin McHugh O'Brien Realty ERA Powered

    23104 Sweetbay Ln, California, MD 20619

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