47

Drayden, MD Homes for Sale

Section Image Section Image
  • /3

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft

    18866 Russell Rd, Leonardtown, MD 20650

    ***Rare Waterfront Opportunity*** Welcome to 18866 Russell Rd, Valley Lee /Leonardtown, MD, a truly exceptional waterfront property offering a private, peaceful setting on a premium lot with stunning views of the water. Currently a 3-bedroom, 1.5-bath home, this property presents the perfect opportunity to reimagine, renovate, or rebuild into your dream waterfront retreat. Surrounded by natural

    Agent Photo

    Shelly Hibbert

    KW Metro Center

    (227) 997-7054

    18866 Russell Rd, Leonardtown, MD 20650
  • /27

    $515,000

    • 4 Beds
    • 3.5 Baths
    • 3,138 Sq Ft

    20724 Hilton Run Ct, Lexington Park, MD 20653

    BACK TO ACTIVEWelcome 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 carpet, recessed lighting, fresh paint, and updated

    Agent Photo

    Vicki Alvey

    RE/MAX One

    (240) 896-4959

    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
  • /15

    $29,900

    • Land
    • 11,761 Sq Ft
    • $110,741 per Acre

    0 Third St, Piney Point, MD 20690

    Looking for the perfect spot to build your future dream home? This 0.27-acre (12,000 sq. ft.) lot in Tall Timbers, MD offers an excellent buy-and-hold opportunity while awaiting potential sewer availability. With the major OAG project bringing jobs to the area and the Lighthouse development underway nearby, sewer service may be coming sooner rather than later—potentially increasing property

    Krista Depenthal Lands2Love

    0 Third St, Piney Point, MD 20690
  • /7

    $269,998

    $30K PRICE DROP
    • Land
    • 3.36 Acres
    • $80,357 per Acre

    16252 Thomas Rd, Piney Point, MD 20674

    Major Price Improvement- Highly motivated Seller. Bring your best reasonable offer and seize this opportunity.Rare buildable waterfront lot in sought-after Piney Point, Maryland. Located at 16252 Thomas Road, this expansive approximately 3.3-acre parcel offers approximately 348 feet of direct water frontage along a tidal creek, providing a serene setting and excellent potential for a custom

    Payam Bakhaje Realty ONE Group Capital

    16252 Thomas Rd, Piney Point, MD 20674
  • /67

    $1,100,000

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

    20098 Piney Point Rd, Callaway, MD 20620

    Welcome to Ms. Piney Point! 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 room area

    Shanita Kelley Samson Properties

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

    $1,244,998

    New Construction $155K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    16242 Thomas Rd, Piney Point, MD 20674

    MAJOR PRICE IMPROVEMENT – BEST VALUE ON THE WATER!Seller offering up to $20,000 in buyer incentives—use toward closing costs or interest rate buydown to reduce your monthly payment. Welcome to an exceptional opportunity to own a brand-new waterfront home set on over 2 private acres in scenic Piney Point. Designed to capture breathtaking sunrise views and peaceful water surroundings, this home

    Payam Bakhaje Realty ONE Group Capital

    16242 Thomas Rd, Piney Point, MD 20674
  • /42

    $749,000

    • 4 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 4

    Debbie Buckingham Samson Properties

    16104 Piney Point Rd, Piney Point, MD 20674
  • /7

    $79,900

    • Land
    • 3.57 Acres
    • $22,381 per Acre

    18832 Piney Point Rd, Valley Lee, MD 20692

    Welcome to 18832 Piney Point Road! This property spans 3.57 acres and includes two lots within one parcel. Build your dream home in the peaceful waterfront community of Piney Point, Maryland. This exceptional parcel offers a rare opportunity to create a custom residence surrounded by natural beauty, privacy, and coastal charm. Nestled near the Potomac River, the property provides a serene setting

    Jonathan Benya EXP Realty, LLC

    18832 Piney Point Rd, Valley Lee, MD 20692
  • /81

    $625,000

    $25K PRICE DROP
    • 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
  • /3

    $725,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 4,588 Sq Ft

    19305 Greens Crossing Ct, Great Mills, MD 20634

    Experience luxury and comfort in this stunning 4-bedroom, 3.5-bath home built in 2015, offering exceptional space, elegant upgrades, and resort-style outdoor living in beautiful Saint Mary's County. From the moment you enter, you’ll love the beautiful hardwood flooring, open-concept layout, and fresh new paint throughout. The heart of the home is the oversized gourmet kitchen featuring a gas

    Heather Heath Deep Roots Real Estate

    19305 Greens Crossing Ct, Great Mills, MD 20634
  • /61

    $799,900

    • 4 Beds
    • 2 Baths
    • 2,322 Sq Ft

    16460 Sayre Point Ln, Piney Point, MD 20674

    Waterfront property on Saint George Island - Original owners are offering this rare opportunity to own a beautifully maintained waterfront home on sought-after St. George Island. Situated on a combined 1.4-acre parcel that includes both the waterfront lot and house lot. This property offers serene views, and direct access to St. George's Creek via a private pier with easy access by boat to ST.

    Carol Kalmus-Choporis Century 21 Redwood Realty

    16460 Sayre Point Ln, Piney Point, MD 20674
  • /7

    $250,000

    • Land
    • 1.55 Acres
    • $161,290 per Acre

    Lot 3 Seaside Ln, Ridge, MD 20680

    Waterfront living on your bucket list? Start now! Bring your ideas, build plans and lawn chairs. You will not want to miss the sunsets over the creek. Lot subdivision restrictions will not allow trailer/mobile homes. There are chickens on the neighbors lot, so be mindful of bringing your pets on the tour. I suggest you park and take the short walk back to the lot and not drive.

    Sheila Milburn Coldwell Banker Premier

    Lot 3 Seaside Ln, Ridge, MD 20680
  • /3

    $125,000

    • Land
    • 2.58 Acres
    • $48,450 per Acre

    46080 Usher Ln, Valley Lee, MD 20692

    If you’re looking for a manageable homesite that still gives you breathing room, this 2.58-acre wooded lot in Valley Lee is a standout. Tucked into a quiet, natural setting, it offers the kind of privacy and space that’s getting harder to find—without feeling overwhelming. The parcel is partially cleared, making it easier to visualize your future home placement, driveway approach, and outdoor

    Robert Gauger EXP Realty, LLC

    46080 Usher Ln, Valley Lee, MD 20692
  • /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
  • /3

    $50,000

    • Land
    • 23,522 Sq Ft
    • $92,593 per Acre

    48574 Smith Dr, Ridge, MD 20680

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group Website Bidding Platform. Bidding begins 5/12/2026 @ 10:00 AM. Bidding ends 5/14/2026 @ 12:20 PM. List Price is Suggested Opening Bid. Deposit: $10,000. This lot of land is located in Ridge, Maryland within St. Mary's County. The property is in close proximity to the Seaside View Recreation Park, located along Jutland Creek,

    Adam Shpritz Ashland Auction Group LLC

    48574 Smith Dr, Ridge, MD 20680
  • /8

    $269,700

    $29K PRICE DROP
    • Land
    • 1.63 Acres
    • $165,460 per Acre

    46175 N Greens Rest Dr, Great Mills, MD 20634

    One of the few remaining pristine lots left in Riverside Farms! 1.63 acre lot with permits, approved site plan, grading, and foundation in for 4BR, 3-4 BA 3500+ sq. ft. custom rambler with basement. Handicap accessible! This desirable neighborhood offers a community park, ball fields, walking trails, picnic areas, and community pier.Conveniently, located close to Leonardtown and Pax River

    Joe and Judi Limerick CENTURY 21 New Millennium

    46175 N Greens Rest Dr, Great Mills, MD 20634
  • /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
  • /2

    $699,900

    New Construction Coming Soon
    • 3 Beds
    • 2 Baths

    17480 Lighthouse Commons Dr, Piney Point, MD 20674

    Carol Kalmus-Choporis Century 21 Redwood Realty

    17480 Lighthouse Commons Dr, Piney Point, MD 20674
  • /2

    $200,000

    • Land
    • 5.41 Acres
    • $36,969 per Acre

    18665 Hebb Way, Drayden, MD 20630

    Dorothy Bistransin Redfin Corp

    18665 Hebb Way, Drayden, MD 20630
  • /2

    $99,000

    • Land
    • 22,651 Sq Ft
    • $190,385 per Acre

    17377 Piney Point Rd, Piney Point, MD 20674

    Discover the opportunity to create your ideal home on this 22,782 square foot parcel (just over half an acre) located on Piney Point in scenic St. Mary's County. Identified as Adjusted Parcel 174, this property offers a peaceful setting with convenient access to the waterfront lifestyle that makes Piney Point such a desirable destination. With no existing improvements, the lot provides a blank

    Matthew Burgan Infinitas Realty Group

    17377 Piney Point Rd, Piney Point, MD 20674
  • /30

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    17282 Crab Pot Ln, Piney Point, MD 20674

    17282 Crab Pot Lane offers an exceptional opportunity to enjoy the waterfront lifestyle you've always dreamed of. Nestled along the shores of the Potomac River in picturesque Piney Point, this beautifully maintained waterfront duplex combines breathtaking views, private beach access, and maintenance-free living in one incredible package. MAIN LEVEL LIVING with some accessibility features in

    Charlotte Long EXP Realty, LLC

    17282 Crab Pot Ln, Piney Point, MD 20674
  • /32

    $419,000

    $21K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,160 Sq Ft

    20166 Manor Dr, Park Hall, MD 20667

    Discover the charm of this beautiful Cape Cod home with NO HOA, nestled in the peaceful community of Park Hall Estates. With 4 oversized bedrooms and 3 full bathrooms, this home is designed for comfortable living and effortless entertaining.The cozy living area, complete with a gas fireplace, is perfect for relaxing on chilly evenings. The well-appointed kitchen is designed for convenience

    Rita Jones The Southside Group Real Estate

    20166 Manor Dr, Park Hall, MD 20667
  • /2

    $69,900

    • Land
    • 3 Acres
    • $23,300 per Acre

    Lot 2 Grayson Rd, Saint Inigoes, MD 20684

    Large wooded 3.00 acre parcel that no perc has been attempted. Located near the gate to Naval base. There is also another 3 acre lot and a 1.6 acre lot.

    Gloria Abell Coldwell Banker Premier

    Lot 2 Grayson Rd, Saint Inigoes, MD 20684
  • /2

    $60,000

    • Land
    • 12,196 Sq Ft
    • $214,286 per Acre

    0 Holly St, Piney Point, MD 20674

    Build a new home on this 12000 Sg ft lot located in Piney Point. Maryland. Public sewer available for hookup.

    Mike Jordan CENTURY 21 New Millennium

    0 Holly St, Piney Point, MD 20674
  • /2

    $65,000

    • Land
    • 1.6 Acres
    • $40,625 per Acre

    0 Grayson Rd, Saint Inigoes, MD 20684

    Large wooded 1.6 acre parcel that no perc has been attempted. Located near the main gate to Naval base. There are two additional lots for sale. Lot 2 and 4 are 3 acres each.

    Gloria Abell Coldwell Banker Premier

    0 Grayson Rd, Saint Inigoes, MD 20684
  • /21

    $395,000

    • 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 offers the

    Robin Cavallaro RE/MAX Realty Group

    17863 2nd St, Tall Timbers, MD 20690
  • /5

    $150,000

    • Land
    • 1.75 Acres
    • $85,714 per Acre

    45252 Happyland Rd, Valley Lee, MD 20692

    1.75 cleared acres zoned commercial. The address of 45252 Happyland Rd was assigned afterCommercial Outparcel C had an approved Perc. St. Mary’s County zoning is Rural Commercial Limited(RCL). Find information on uses of an RCL lot online at St. Mary's County comprehensive zoning ordinance. Excerpt from ordinance (RCL Jul 24, 2007... By the enactment of County Commissioners Ordinance No.

    Lawrence Lessin Save 6, Incorporated

    45252 Happyland Rd, Valley Lee, MD 20692
  • /4

    $125,000

    $35K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    47923 Beachville Rd, Saint Inigoes, MD 20684

    Nestled in the peaceful countryside of St. Inigoes, this unique Beachville Road property offers the perfect blend of privacy, space, and opportunity in Southern Maryland. Surrounded by natural beauty and open skies, the setting provides the calm, relaxed lifestyle while still remaining within reach of local conveniences, waterfront recreation, and major commuter routes. The property presents an

    Anita Graham Realty One Group Performance, LLC

    47923 Beachville Rd, Saint Inigoes, MD 20684
  • /2

    $85,000

    $10K PRICE DROP
    • Land
    • 1.5 Acres
    • $56,667 per Acre

    0 Piney Point Rd, Callaway, MD 20620

    Discover the perfect canvas for your dream home on this 1.5-acre parcel of land, nestled in a vibrant community that offers both tranquility and convenience. Imagine waking up each day surrounded by nature, with ample space to create your own private oasis while still being just moments away from local amenities. This prime piece of land is situated in an area known for its friendly atmosphere

    Jessica Raley CENTURY 21 New Millennium

    0 Piney Point Rd, Callaway, MD 20620
  • /2

    $99,900

    • Land
    • 1 Acre
    • $99,900 per Acre

    17475 Mount Zion Church Rd, Saint Inigoes, MD 20684

    Beautiful lot close to base and St Mary's college in beautiful St Mary's city. only a few minutes to restaurants and shopping. This lot has a Dug well and septic on property. Trailor on property is a tear down.

    Gloria Abell Coldwell Banker Premier

    17475 Mount Zion Church Rd, Saint Inigoes, MD 20684
  • /16

    $399,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,912 Sq Ft

    16320 Point Lookout Rd, Saint Marys City, MD 20686

    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 system.

    Billy Rabbitt The Southside Group Real Estate

    16320 Point Lookout Rd, Saint Marys City, MD 20686
  • /12

    $175,000

    $51K PRICE DROP
    • Land
    • 8.93 Acres
    • $19,597 per Acre

    0 Snowhill Way, Lexington Park, MD 20653

    Discover the perfect opportunity to build your dream property on this 8.93-acre agricultural-zoned parcel, nestled in the picturesque and highly sought-after area of St. Mary’s City. Located at the end of a quiet cul-de-sac, this lot offers unparalleled privacy and tranquility, surrounded by nature and the charm of Southern Maryland. With ample space for farming, gardening, or simply enjoying the

    Matthew Burgan Infinitas Realty Group

    0 Snowhill Way, Lexington Park, MD 20653
  • /46

    $349,900

    • 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
  • /57

    $889,900

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

    16146 Thomas Rd, Piney Point, MD 20674

    Experience the timeless charm of Chesapeake Bay living at this beautifully renovated waterfront Colonial on historic St. George Island. Built in 1927 and updated in 2018, this 4BR/3BA property sits on 2.2 private acres along St. George Creek with 40 feet of waterfront, stunning sunset views, and a private pier (2019) ready for embracing SOUTHERN MARYLAND ISLAND LIFE—boating, fishing, crabbing,

    Conor Loughran CENTURY 21 New Millennium

    16146 Thomas Rd, Piney Point, MD 20674
  • /6

    $74,000

    • Land
    • 40,075 Sq Ft
    • $80,435 per Acre

    18390 Matthews Dr, Lexington Park, MD 20653

    Peaceful Coastal Lot Near the Beach — Just Under One Acre! Discover the perfect blend of privacy and convenience with this beautiful vacant lot, nestled in a quiet, partially cleared setting just under one acre. Located less than a mile from the waterfront and Elm’s Beach Park, and just seven minutes from the Patuxent River Naval Base, this property offers endless possibilities. Whether you’re

    Christine Chatmon Dudley Pro Homes

    18390 Matthews Dr, Lexington Park, MD 20653
  • /2

    $59,000

    • Land
    • 1.8 Acres
    • $32,778 per Acre

    0 Sea Side View Rd Unit MDSM2025850, Ridge, MD 20680

    Katherine Dean RE/MAX One

    0 Sea Side View Rd Unit MDSM2025850, Ridge, MD 20680
  • /59

    $505,000

    $10K 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

Showing Results 1 - 40, Page 1 of 2

Frequently Asked Questions

What are the most popular zip codes in Drayden, MD?
The most popular zip codes in Drayden, MD include 20630, 20692, 20674, 20634 and 20653.
What are the most popular neighborhoods near Drayden, MD?
The most popular neighborhoods near Drayden, MD are Piney Point, Saint George Island and Mechanicsville.
How to Buy a Home How to Finance a Home How to Sell a Home