25

Piney Point, MD Houses for Sale

Section Image
  • 20098 Piney Point Rd, Callaway, MD 20620
    20098 Piney Point Rd, Callaway, MD 20620
    20098 Piney Point Rd, Callaway, MD 20620
    /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
  • 46461 Porto Bello Ct, Drayden, MD 20630
    46461 Porto Bello Ct, Drayden, MD 20630
    46461 Porto Bello Ct, Drayden, MD 20630
    /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
  • 16242 Thomas Rd, Piney Point, MD 20674
    16242 Thomas Rd, Piney Point, MD 20674
    16242 Thomas Rd, Piney Point, MD 20674
    /75

    $999,900

    New Construction $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
  • 16104 Piney Point Rd, Piney Point, MD 20674
    16104 Piney Point Rd, Piney Point, MD 20674
    16104 Piney Point 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
  • 18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    /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
  • 16101 Piney Point Rd, Piney Point, MD 20674
    16101 Piney Point Rd, Piney Point, MD 20674
    16101 Piney Point Rd, Piney Point, MD 20674
    /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
  • 43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, Leonardtown, MD 20650
    /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
  • 46234 Stasha Ct, Drayden, MD 20630
    46234 Stasha Ct, Drayden, MD 20630
    46234 Stasha Ct, Drayden, MD 20630
    /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
  • 19103 Windsor Ct, Drayden, MD 20630
    19103 Windsor Ct, Drayden, MD 20630
    19103 Windsor 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
  • 19166 N Porto Bello Dr, Drayden, MD 20630
    19166 N Porto Bello Dr, Drayden, MD 20630
    19166 N Porto Bello Dr, Drayden, MD 20630
    /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
  • 17480 Lighthouse Commons Dr, Piney Point, MD 20674
    17480 Lighthouse Commons Dr, Piney Point, MD 20674
    17480 Lighthouse Commons Dr, Piney Point, MD 20674
    /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
  • 46200 Greens Rest Way, Great Mills, MD 20634
    46200 Greens Rest Way, Great Mills, MD 20634
    46200 Greens Rest Way, Great Mills, MD 20634
    /92

    $970,000

    • 3 Beds
    • 2.5 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
  • 17597 Whitestone Dr, Tall Timbers, MD 20690
    17597 Whitestone Dr, Tall Timbers, MD 20690
    17597 Whitestone Dr, Tall Timbers, MD 20690
    /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
  • 19335 Greens Crossing Ct, Great Mills, MD 20634
    19335 Greens Crossing Ct, Great Mills, MD 20634
    19335 Greens Crossing Ct, Great Mills, MD 20634
    /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
  • 17863 2nd St, Tall Timbers, MD 20690
    17863 2nd St, Tall Timbers, MD 20690
    17863 2nd St, Tall Timbers, MD 20690
    /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
  • 47558 Lucas Cove Ln, Lexington Park, MD 20653
    47558 Lucas Cove Ln, Lexington Park, MD 20653
    47558 Lucas Cove Ln, Lexington Park, MD 20653
    /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
  • 18800 McKays Beach Rd, Leonardtown, MD 20650
    18800 McKays Beach Rd, Leonardtown, MD 20650
    18800 McKays Beach Rd, Leonardtown, MD 20650
    /16

    $350,000

    $115K PRICE DROP
    • 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
  • 17266 Larimer St, Piney Point, MD 20674
    17266 Larimer St, Piney Point, MD 20674
    17266 Larimer St, Piney Point, MD 20674
    /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
  • 57 Hazel Dr, Hague, VA 22469
    57 Hazel Dr, Hague, VA 22469
    57 Hazel Dr, Hague, VA 22469
    /15

    $199,500

    • 3 Beds
    • 2 Baths
    • 1,092 Sq Ft

    57 Hazel Dr, Hague, VA 22469

    Bonny M. Townsend Historyland Realty LLC

    57 Hazel Dr, Hague, VA 22469
  • 44939 Shore Dr, Tall Timbers, MD 20690
    44939 Shore Dr, Tall Timbers, MD 20690
    44939 Shore Dr, Tall Timbers, MD 20690
    /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
  • 27 Orange Dr, Hague, VA 22469
    27 Orange Dr, Hague, VA 22469
    27 Orange Dr, Hague, VA 22469
    /38

    $699,000

    • 4 Beds
    • 5 Baths
    • 3,001 Sq Ft

    27 Orange Dr, Hague, VA 22469

    Bonny M. Townsend Historyland Realty LLC

    27 Orange Dr, Hague, VA 22469
  • 19163 N Porto Bello Ln, Drayden, MD 20630
    19163 N Porto Bello Ln, Drayden, MD 20630
    19163 N Porto Bello Ln, Drayden, MD 20630
    /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
  • 45433 Drayden Rd, Valley Lee, MD 20692
    45433 Drayden Rd, Valley Lee, MD 20692
    45433 Drayden Rd, Valley Lee, MD 20692
    /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
  • 16102 Piney Point Rd, Piney Point, MD 20674
    16102 Piney Point Rd, Piney Point, MD 20674
    /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
  • 16386 Ball Point Rd, Piney Point, MD 20674
    16386 Ball Point Rd, Piney Point, MD 20674
    16386 Ball Point Rd, Piney Point, MD 20674
    /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
Maryland St Marys County

Houses for Sale in Piney Point, MD

How to Buy a Home How to Finance a Home How to Sell a Home

In Piney Point, there are currently 25 houses for sale, offering an array of options for potential buyers. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Piney Point, MD and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group