37

Drayden, MD Houses for Sale

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  • /21

    $499,999

    $15K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,138 Sq Ft

    20724 Hilton Run Ct, Lexington Park, MD 20653

    Price Improvement Sellers are going to add to rental marketWelcome to this exquisite four-bedroom, three-and-a-half-bath Colonial, where luxury meets comfort. Step inside to discover a beautifully designed interior with high-end finishes throughout. The open-concept main living area is filled with natural light and features engineered wood flooring in the kitchen and dining area, plush

    Agent Photo

    Vicki Alvey

    RE/MAX One

    20724 Hilton Run Ct, Lexington Park, MD 20653
  • /83

    $1,900,000

    • 4 Beds
    • 3.5 Baths
    • 5,747 Sq Ft

    19393 N Snow Hill Manor Rd, Lexington Park, MD 20653

    Welcome to this truly exceptional, one-of-a-kind waterfront estate on the historic St. Mary’s River. Nestled on 1.72 beautifully landscaped acres, this property boasts 150 feet of private water frontage, along with an impressive private pier equipped with three boat lifts, electric, water, and approximately 10 feet of deep water—ideal for accommodating vessels of nearly any size.Designed for

    Sheri Goldman Long & Foster Real Estate, Inc.

    19393 N Snow Hill Manor Rd, Lexington Park, MD 20653
  • /41

    $510,000

    • 3 Beds
    • 2 Baths
    • 1,552 Sq Ft

    17347 Whitaker Ct, Saint Inigoes, MD 20684

    Nestled on over 2 private acres at the end of a quiet cul-de-sac in St. Inigoes, this beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort, functionality, and outdoor enjoyment. Conveniently located just 5 minutes from Webster Field and 15 minutes from Patuxent River Naval Air Station, this property provides both privacy and accessibility. Step inside to an inviting

    Connie Gunn CENTURY 21 New Millennium

    17347 Whitaker Ct, Saint Inigoes, MD 20684
  • /67

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 5,939 Sq Ft

    20098 Piney Point Rd, Callaway, MD 20620

    Want to live near your business?! This beautiful and classic 3 bedroom, 2 and half bathroom rancher has well-maintained curb appeal and the interior to match, beginning with the flower bed enriched porch. From the front door you are greeted with a spacious living room great for relaxing and enjoying the view from the large picturesque windows. This area also includes a separate kitchen/dining

    Shanita Kelley Samson Properties

    20098 Piney Point Rd, Callaway, MD 20620
  • /75

    $680,000

    • 5 Beds
    • 3 Baths
    • 3,430 Sq Ft

    46461 Porto Bello Ct, Drayden, MD 20630

    Welcome to Porto Bello Court, tucked away on a quiet cul-de-sac in the sought after Porto Bello Estates community of Drayden. This beautifully designed two-story home offers an abundance of natural light, creating a warm and inviting atmosphere throughout its spacious floor plan. Thoughtfully designed with versatility in mind, the expansive layout provides endless possibilities for today’s

    Diana Washabaugh CENTURY 21 New Millennium

    46461 Porto Bello Ct, Drayden, MD 20630
  • /75

    $999,900

    New Construction Open Sun 1PM - 4PM $400K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    16242 Thomas Rd, Piney Point, MD 20674

    MAJOR PRICE IMPROVEMENT — NEW CONSTRUCTION WATERFRONT UNDER $1 MILLION! An exceptional opportunity to own a newly constructed waterfront retreat in beautiful Piney Point. Set on approximately 2 acres with expansive waterfront views, this thoughtfully designed home combines luxury, privacy and the relaxed Southern Maryland waterfront lifestyle.Wake up to beautiful SUNRISE VIEWS OVER THE

    Payam Bakhaje Realty ONE Group Capital

    16242 Thomas Rd, Piney Point, MD 20674
  • /43

    $620,000

    $129K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,440 Sq Ft

    16104 Piney Point Rd, Piney Point, MD 20674

    Welcome to your waterfront escape on the point of St. George Island, where the Potomac River meets the Chesapeake Bay.This home was built by the local Amish community for this family.This rare offering features 154 feet of riprapped shoreline, delivering sweeping water views and front-row seats to breathtaking sunrises, passing boats, and endless coastal serenity.The main home offers

    Debbie Buckingham Samson Properties

    16104 Piney Point Rd, Piney Point, MD 20674
  • /74

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    18937 Hodges Ln, Leonardtown, MD 20650

    If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, Leonardtown, MD 20650
  • /3

    $550,000

    Coming Soon Sep 2
    • 4 Beds
    • 3.5 Baths
    • 2,600 Sq Ft

    19201 S King James Pkwy, Lexington Park, MD 20653

    Experience peaceful Southern Maryland living with room to relax, entertain, and enjoy the outdoors. Located in the St. James community, you'll love the large homesites, neighborhood pool, and convenient access to schools, shopping, dining, and NAS Patuxent River. New HVAC systems and a newer roof, new flooring, fresh painting. The basement has a full bath and a room; if you add door, then you can

    Natalya Ford RE/MAX One

    19201 S King James Pkwy, Lexington Park, MD 20653
  • /35

    $599,900

    • 3 Beds
    • 1 Bath
    • 828 Sq Ft

    16101 Piney Point Rd, Piney Point, MD 20674

    Some properties are purchased for the house. Others are purchased for the place. Set on a narrow finger of land between two bodies of water, 16101 Piney Point Road offers an extraordinary waterfront setting with sunrise light on one side and spectacular sunset views on the other. The existing cottage provides an immediate place to enjoy life, watch the sky change, enjoy the water, and begin

    Michelle Camaioni RE/MAX One

    16101 Piney Point Rd, Piney Point, MD 20674
  • /2

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    44911 Buck Redman Rd, Callaway, MD 20620

    Nestled on a serene 2.17-acre lot, this charming ranch-style home offers a perfect blend of comfort and nature. Surrounded by lush trees and partly wooded areas, the property provides a tranquil retreat, ideal for those seeking peace and privacy. Imagine sipping your morning coffee while enjoying views of the garden and woods from your rear yard, where you can create your own outdoor oasis.

    Sheila Milburn Coldwell Banker Premier

    44911 Buck Redman Rd, Callaway, MD 20620
  • /28

    $469,900

    • 3 Beds
    • 3 Baths
    • 1,691 Sq Ft

    43954 Main Way Rd, Leonardtown, MD 20650

    Set on a level, open corner lot with a small view of the Potomac River—and best of all, **NO HOA**—this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features

    Danny Martin Keller Williams Flagship

    43954 Main Way Rd, Leonardtown, MD 20650
  • /32

    $679,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,643 Sq Ft

    46234 Stasha Ct, Drayden, MD 20630

    *** To Be Built *** ONE ACRE Plus Wooded Level LOT *** THE CANTERBURY II Model *** GARAGE ****FABULOUS KITCHEN w/Super Island & GRANITE Counters *** Pantry *** STAINLESS appliances *** Open Concept ** 1st Floor FAMILY ROOM open to the Kitchen *** full BASEMENT w/Rough in for a FULL BATH ** Optional REC ROOM and DEN *** INTERNET Available *** Street LIGHTS ** WARRANTY *** Pick this CANTERBURY II

    Lisa Riggleman RE/MAX One

    46234 Stasha Ct, Drayden, MD 20630
  • /45

    $635,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    19103 Windsor Ct, Drayden, MD 20630

    ** ONE ACRE Plus Wooded Level LOT *** The Stella Model or Select from one of our other Plans ** To Be Built ** Still time to Customize Selections and upgrades *** FABULOUS KITCHEN w/Super Island & Granite Counters *** Huge Pantry *** STAINLESS Appliances *** First Floor Primary Bedroom complete with walk in Closet *** Master Bath with Soak Tub and Walk in Shower *** Tow Additional Main Floor

    Lisa Riggleman RE/MAX One

    19103 Windsor Ct, Drayden, MD 20630
  • /70

    $799,900

    • 5 Beds
    • 3 Baths
    • 2,214 Sq Ft

    16146 Thomas Rd, Piney Point, MD 20674

    Live the Chesapeake Bay lifestyle on historic St. George Island! This beautifully renovated waterfront Colonial sits on 2.2 private acres with 40 feet of waterfront on St. George Creek, offering spectacular sunset views, a private pier (2019), and direct access to boating, fishing, crabbing, and kayaking. Originally built in 1927 and renovated in 2018, the property features a 3BR/2BA main home

    Conor Loughran CENTURY 21 New Millennium

    16146 Thomas Rd, Piney Point, MD 20674
  • /40

    $550,000

    Open Sun 1PM - 3PM
    • 5 Beds
    • 3 Baths
    • 3,593 Sq Ft

    18361 Matthews Dr, Lexington Park, MD 20653

    This impressive 5BR, 3 BA Colonial is nestled on almost 1 acre in a Lexington Park neighborhood. This home offers an estimated 3,130 square feet of warm, light-filled living space designed for both effortless daily living and easy entertaining. The spacious bedrooms provide flexibility for family, home offices, or guest accommodations. Three full bathrooms ensure no morning rush hour stress. With

    Lisa Van Tassel Home Towne Real Estate

    18361 Matthews Dr, Lexington Park, MD 20653
  • /25

    $776,220

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,253 Sq Ft

    19166 N Porto Bello Dr, Drayden, MD 20630

    The PARKER Model, Elevation One ** Please excuse our mess while construction is underway ** Wonderful Front Porch ** One Acre Plus WOODED Level Lot **FABULOUS KITCHEN w/Super Island & Granite Counters *** Huge PANTRY *** Upgraded STAINLESS Appliances *** First Floor Primary Bedroom complete with Custom Box Ceiling *** Master Bath with CUSTOM Walk in SHOWER w/Custom Seat ** Two Additional Main

    Lisa Riggleman RE/MAX One

    19166 N Porto Bello Dr, Drayden, MD 20630
  • /36

    $629,900

    New Construction $70K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,465 Sq Ft

    17480 Lighthouse Commons Dr, Piney Point, MD 20674

    Brand-New Rambler Near Piney Point Lighthouse! Experience the perfect blend of modern comfort and coastal charm in this beautifully crafted new construction rambler. Featuring luxury vinyl plank flooring, quartz counters, two tone cabinets, stainless appliances & custom tiled shower. This thoughtfully designed home offers a spacious family room, separate dining room, and a large eat-in kitchen

    Carol Kalmus-Choporis Century 21 Redwood Realty

    17480 Lighthouse Commons Dr, Piney Point, MD 20674
  • /92

    $970,000

    • 3 Beds
    • 2 Baths
    • 2,590 Sq Ft

    46200 Greens Rest Way, Great Mills, MD 20634

    Welcome to 46200 Greens Rest Way, a truly special waterfront retreat tucked away on more than 13 acres with approximately 200 feet of frontage along the beautiful St. Mary’s River. Surrounded by mature woodland, tidal marsh and meandering creeks, this peaceful setting offers exceptional privacy, abundant wildlife and a rare connection to nature.Inside, extensive windows and skylights fill

    Robin Errington CENTURY 21 New Millennium

    46200 Greens Rest Way, Great Mills, MD 20634
  • /91

    $875,000

    • 4 Beds
    • 3.5 Baths
    • 3,106 Sq Ft

    17597 Whitestone Dr, Tall Timbers, MD 20690

    The Landings at Piney Point is a highly sought-after waterfront community offering exceptional amenities and a true coastal lifestyle. Residents enjoy one of the most beautiful private beaches in Southern Maryland, along with a community pool, tennis court, playground, harbor with boat slips, boat trailer storage, and more.Whether you enjoy boating, fishing, kayaking, or simply relaxing by

    Dawn Wood O'Brien Realty ERA Powered

    17597 Whitestone Dr, Tall Timbers, MD 20690
  • /62

    $585,000

    $15K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,436 Sq Ft

    19335 Greens Crossing Ct, Great Mills, MD 20634

    **SELLER OFFERING $10,000 FLOORING CREDIT WITH ACCEPTABLE OFFER** Classic colonial in desirable The Crossing at Riverside Farms neighborhood. Feel like you're in the country on this 1+ acre lot but only minutes to shopping, schools, parks and Pax River Base. Nice open floor plan features a generous open floor plan with spacious kitchen that has ample cabinet and counter space, walk-in pantry,

    Jennifer Mullennix CENTURY 21 New Millennium

    19335 Greens Crossing Ct, Great Mills, MD 20634
  • /21

    $349,900

    $45K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    17863 2nd St, Tall Timbers, MD 20690

    Welcome to life in Tall Timbers — where peaceful surroundings, waterfront charm, and everyday comfort come together beautifully.This freshly updated 3-bedroom home is completely move-in ready with brand new carpet, newly refinished hardwood floors, and fresh paint throughout. The light-filled interior creates a warm and inviting feel from the moment you walk in.The spacious layout

    Robin Cavallaro RE/MAX Realty Group

    17863 2nd St, Tall Timbers, MD 20690
  • /43

    $529,000

    • 3 Beds
    • 2 Baths
    • 1,371 Sq Ft

    47558 Lucas Cove Ln, Lexington Park, MD 20653

    Welcome to 47558 Lucas Cove Lane, where peaceful waterfront living meets endless potential. Tucked away on a private, wooded double lot overlooking scenic Lucas Cove, just off the beautiful St. Mary's River, this charming 3-bedroom, 2-bath home offers a rare opportunity to enjoy the best of Southern Maryland's waterfront lifestyle. Designed to maximize its exceptional setting, the home is

    Matthew Burgan Infinitas Realty Group

    47558 Lucas Cove Ln, Lexington Park, MD 20653
  • /16

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    18800 McKays Beach Rd, Leonardtown, MD 20650

    This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal retreat. Nestled on the serene shores of McKays Cove, several major exterior capital improvements are already complete. The structure features a brand-new Amish-built roof, new gutters, and premium new Andersen windows throughout. Personal Boat Ramp: Private ramp for seamless watercraft launching and only one

    Chris Coughlan RE/MAX One

    18800 McKays Beach Rd, Leonardtown, MD 20650
  • /7

    $95,000

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft

    17266 Larimer St, Piney Point, MD 20674

    This property will be sold at ONLINE AUCTION. LIST PRICE REPRESENTS OPENING BID. Opportunity knocks in Piney Point at 17266 Larimer St! This 2bd/1ba rancher offers a blank slate for investors or handy homeowners to customize. Since utilities are already in place, the renovation is mostly cosmetic and allows for multiple exit strategies. This water-oriented community has a history of strong sales

    Ben Garner Cummings & Co. Realtors

    17266 Larimer St, Piney Point, MD 20674
  • /4

    $100,000

    $60K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    47923 Beachville Rd, Saint Inigoes, MD 20684

    Welcome to 47923 Beachville Road in St. Inigoes, Maryland, an opportunity for the buyer or investor ready to bring their vision to life. Situated on approximately .34 acres in Southern Maryland, this property offers the chance to renovate, reimagine, and create something of your own. The home is a true fixer-upper and is being sold in its current condition, with substantial repairs and

    Anita Graham Realty One Group Performance, LLC

    47923 Beachville Rd, Saint Inigoes, MD 20684
  • /19

    $379,900

    $30K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 2,912 Sq Ft

    16320 Point Lookout Rd, Lexington Park, MD 20653

    Nestled in a peaceful Southern Maryland setting, this private property offers the perfect blend of space, serenity, and convenience. Surrounded by open farmland, the home provides a quiet retreat while still being just minutes from St. Mary’s College.Major system updates offer true peace of mind, including a new roof, updated septic and well, replacement windows, and an upgraded heating

    Billy Rabbitt The Southside Group Real Estate

    16320 Point Lookout Rd, Lexington Park, MD 20653
  • /46

    $299,000

    $51K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,086 Sq Ft

    15240 Point Lookout Rd, Saint Inigoes, MD 20684

    A RARE FIND! Vintage Historic 1920 Victorian Styled Home on a terrific level 1.5-acre lot minutes from NESEA and just south of Saint Mary's City. All systems go! Newer roof, 2-year-old updated septic, 2-year-old heating/ac system. Extra-large rooms. Pleasantly Liveable but available for 21st Century updates and restoration. Three original Chimneys are blocked but easily revived. Beautiful lot

    Carl Franzen Franzen Realtors, Inc.

    15240 Point Lookout Rd, Saint Inigoes, MD 20684
  • /40

    $334,900

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft

    17367 Mount Zion Church Rd, Saint Inigoes, MD 20684

    Completely renovated from top to bottom, this beautifully updated 3-bedroom, 2-bath home offers the perfect blend of modern finishes and peaceful Southern Maryland living. Thoughtfully upgraded throughout, the home features a brand-new kitchen with quartz countertops, new cabinetry, stainless steel appliances, updated bathrooms, luxury vinyl plank flooring, new windows, new siding, updated

    Emily Watts Real Broker, LLC

    17367 Mount Zion Church Rd, Saint Inigoes, MD 20684
  • /59

    $482,000

    $33K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,108 Sq Ft

    44939 Shore Dr, Tall Timbers, MD 20690

    One level living with waterfront views are ready for you to move right in! This one story home includes 4 bedrooms and 2 full bathrooms. The home was renovated in 2016. As you enter the home, the open concept kitchen and main living area are perfect for hosting gatherings or entertaining. The kitchen has quartz counters, upgraded cabinets, stainless appliances, tile backsplash, upgraded lighting,

    Kelly Padgett Century 21 Redwood Realty

    44939 Shore Dr, Tall Timbers, MD 20690
  • /31

    $599,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,343 Sq Ft

    19163 N Porto Bello Ln, Drayden, MD 20630

    *** To Be Built *** ONE ACRE Plus Wooded Level LOT *** THE ARUNDEL Model, Elevation II*** 2 CAR GARAGE ****FABULOUS KITCHEN w/Super Island & GRANITE Counters *** Pantry *** STAINLESS appliances *** Open Concept ** 1st Floor FAMILY ROOM open to the Kitchen *** full BASEMENT w/Rough in for a FULL BATH ** Optional REC ROOM and DEN *** INTERNET Available *** Street LIGHTS ** WARRANTY *** Pick this

    Lisa Riggleman RE/MAX One

    19163 N Porto Bello Ln, Drayden, MD 20630
  • /28

    $2,250,000

    Coming Soon Sep 30
    • 4 Beds
    • 4 Baths
    • 4,228 Sq Ft

    45433 Drayden Rd, Valley Lee, MD 20692

    Welcome to Mount Olive Farm! A breathtaking 39-acre horse farm featuring a beautifully restored manor home originally built in 1880. Rich in history and thoughtfully updated over the years, this exceptional estate seamlessly blends timeless character with modern amenities.The home features a stunning gourmet kitchen addition equipped with a commercial-grade range, Viking double ovens, a

    Carol Kalmus-Choporis Century 21 Redwood Realty

    45433 Drayden Rd, Valley Lee, MD 20692
  • /2

    $399,900

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    16102 Piney Point Rd, Piney Point, MD 20674

    Opportunity meets waterfront potential at 16102 Piney Point Road. Set in a distinctive coastal location, this property offers buyers the chance to create something truly special along the water. The existing structure is in need of substantial renovation and may also be considered a candidate for removal and replacement. This is not a cosmetic project. Buyers should expect a serious undertaking

    Michelle Camaioni RE/MAX One

    16102 Piney Point Rd, Piney Point, MD 20674
  • /8

    $85,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,956 Sq Ft

    19980 Courtneyville Rd, Park Hall, MD 20667

    Property is being sold strictly as-is. Utilities are on and working, please feel free to reach out to the listing agent with any questions!

    Justin Mika The Southside Group Real Estate

    19980 Courtneyville Rd, Park Hall, MD 20667
  • /2

    $425,000

    Coming Soon Aug 28
    • 7 Beds
    • 3 Baths
    • 2,530 Sq Ft

    48448 Mattapany Rd, Lexington Park, MD 20653

    Spacious and versatile home offering 7 bedrooms and 3 full baths in a convenient Lexington Park location. With 4 bedrooms upstairs and 3 on the lower level, this home provides plenty of room for multi-generational living, guests, or flexible work-from-home space. Enjoy an oversized attached two-car garage and a huge, flat backyard perfect for outdoor entertaining, recreation, or future

    Billy Rabbitt The Southside Group Real Estate

    48448 Mattapany Rd, Lexington Park, MD 20653
  • /56

    $495,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft

    17248 Gum Landing Rd, Saint Inigoes, MD 20684

    Waterfront on Smith Creek! Just in time for summer fun, this waterfront rambler, with private pier, will have you fishing and crabbing from morning until night. Hardwood flooring greets you upon entering and flows throughout most of the main level. Tilt-out windows and a screened porch ideal for relaxing and enjoying all the sights and sounds of living on the water. New paint and ceiling fans

    Robin Errington CENTURY 21 New Millennium

    17248 Gum Landing Rd, Saint Inigoes, MD 20684
  • /74

    $609,900

    • 3 Beds
    • 2.5 Baths
    • 2,142 Sq Ft

    16386 Ball Point Rd, Piney Point, MD 20674

    Wake up to breathtaking, mile long views of the St. Mary’s River, the Potomac River, and St. George’s Creek from this beautiful three-level waterfront home. Designed with a bright, open floor plan, this residence offers a great floorplan for everyday living and effortless entertaining.Step outside onto the expansive 42-foot Trex deck overlooking the water — an ideal setting for gatherings,

    Jennifer Goddard CENTURY 21 New Millennium

    16386 Ball Point Rd, Piney Point, MD 20674
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