Maryland Waterfront Homes for Sale 20650

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Featured Maryland Waterfront Homes for Sale 20650

Approximately 5700 feet of shoreline on this unique property in St. Mary's County, the Mother County, along the still waters of Herring Creek.  This is the best of both worlds by being country quiet and commuter friendly.   An enchanting 1800 built home needing total rehab.  Imagine keeping the character of the house with all the land to include a very secluded pond, tillable fields, and woods providing for the hobby enthusiast and outdoorsmen alike with waterfoul and wildlife abound.  You can set up a family compound with stunning views or whatever you'd like as your possiblilites are endless.  Maybe a venue for weddings and events or Bed and Breakfast.  Property is approx 12 miles from St. Mary's County Regional Airport, a growing and expanding, airport,  approximately 8 miles to Patuxent River Naval Air Station, and approximately 7 miles from Historic St. Mary's City.
44505 Blake Creek
Leonardtown, Maryland
  • 3 Beds
  • 2 Baths
  • 2,532 SqFt
  • 175 Acres
Looking for elbow room?  Look no further.  OVER 200 acres of land!  Property borders Potomac River & Poplar Hill Creek.  LOTS of farm land and forest land.  Contact the Listing Agent to schedule your private viewing today.
42520 Riverwinds Drive
Leonardtown, Maryland
  • 4 Beds
  • 2 Baths
  • 2,744 SqFt
  • 215.730 Acres
Its not often that a residence like this comes to the market. This exceptional  waterfront estate  offers everything you could imagine and so much more. From boating , Kayaking or jet skiing you can enjoy everything waterfront living provides. Owners have recently remodeled the kitchen, Including new granite countertops, double oven, Gas range & hood, Dishwasher, Sinks and refrigerator. Other additions include Finish lower level to office and exercise room and full bath and storage room. Replace driveway, Front sidewalk and porch, Extended rear patio and added sidewalk connecting to driveway and exterior storage room. New boat lift, Lawn sprinkler system, Replaced two of the three HVAC units. Alarm system with cameras. Full home window treatments with remote control for easy open/close. Shore power and floating additional docking. New architectural roof system and full soffit replacement. Heavy hardscape/landscape. Located on quite cul-de-sac. Stable community, No waterfront transfer on this street in over six years. Enjoy everything that Brenton Bay has to offer.  Just steps to the golf course, Tennis courts pool and private beach. This is truly a one of a kind waterfront estate that is guaranteed to impress.
21689 Pebble Beach Court
Leonardtown, Maryland
  • 5 Beds
  • 6 Baths
  • 6,038 SqFt
  • 0.860 Acres
All rooms have new plank flooring.  Remarkable secluded waterfront property with pier on over 3 acres with beautiful views of the creek!  Very hard to find waterfront with this much land together.  Completely all brick home situated so most rooms have view of the water with the main living area and office having full frontal views.  Two primary bedrooms with attached primary baths and cabinets in bath have lazy susans and pull outs like a kitchen would.  One has jetted tub and all have extra heaters in them.  All other rooms are large with closets to match.  Kitchen has a center island with room for eating and newer stainless appliances.  Large, 16 x 32' workshop set up for a handyman and his power tools with many electric outlets.  Additional shed on the property for a lawn mower and yard tools.  Dual zoned HVAC, 1 unit around 6 yrs young.  Large laundry room with laundry sink and lots of cabinets.  Check out the virtual tour to get a better feel of just how large all rooms are.  Perfect spot for an artist or author.  Let your imagination run.
19633 Tower Hill Road
Leonardtown, Maryland
  • 4 Beds
  • 3 Baths
  • 3,407 SqFt
  • 3.330 Acres
Beautiful Modern Colonial in Big Chestnut - being built in owners lot - Home has 4 spacious bedroom all with their own sitting areas and bathrooms - Owners suite is a getaway space of its own.  Finished basement and detached garage included in this price - Big Chestnut lot lot not included - We can inspire you and you can create your own dream home - call me for more details - 3 lots left!
40080 Greentree
Leonardtown, Maryland
  • 4 Beds
  • 4 Baths
  • 7,194 SqFt
  • 1.350 Acres
Other lots in the area, call us to discuss
TBB - Custom Home - Many other floor plans and locations - call to discuss
44798 Medleys Neck Road
Leonardtown, Maryland
  • 4 Beds
  • 5 Baths
  • 3,000 SqFt
  • 4.420 Acres
Charming Waterfront Cape Cod on Half Acre in sought after McKays Beach. Two (2) Piers with Water, Electric and Fish Cleaning Station, Private Boat Ramp, Boathouse/Covered Slip, Grandfathered Gazebo over the Water, Several Large Boat Slips and DEEP WATER on Herring Creek.  The Enchanting Cottage was built in 1946 and has Original Hardwood Floors throughout.  Stylish Kitchen with Silestone Countertops, Huge Island with Prep Sink, Gas Range and a Large Pantry. Cozy Living Room with Original Knotty Pine Walls and Wood Burning Fireplace.  Bright Sunroom with Incredible Views.  Two (2) Bedrooms on the Main Level and a Lovely Primary Suite on the 2nd Level with Walk-In Closet.  Huge Family Room on 2nd Level could be 4th Bedroom/Den/Office if needed.   Watch the Sunrise over the Creek on the Tranquil Veranda  with Custom Boat Curtains for Three Season use that convey.  Large Deck, One (1) Car Garage and a HUGE 70’ Workshop/Outbuilding.  You will fall in love with this Whimsical Property.  Serene and Peaceful.
18858 Mckays Beach Road
Leonardtown, Maryland
  • 3 Beds
  • 2 Baths
  • 2,682 SqFt
  • 0.460 Acres
A rare waterfront with 4 bedrooms 2 baths Amazing Waterview's and Sunsets with Pier and bulkhead 
an open feel and plenty of room with a sunroom and art room.  Detached storage shed.  You will have to see for yourself.
42025 White Point Beach Road
Leonardtown, Maryland
  • 4 Beds
  • 2 Baths
  • 2,558 SqFt
  • 0.280 Acres
Waterfront Paradise in St. Mary’s County!
Presenting 22273 St. Clements Ave. in Leonardtown, Maryland.  This one-story western facing waterfront property on St. Clements Bay is a refurbished, move-in ready 2,250 square foot three-bedroom, two bath home on ¾ acre with expansive vistas of the Bay and stunning sunset views. The home is just 7 miles from the historic downtown Leonardtown square, with its cafes, restaurants and quaint shops or travel to town by boat!  The property is only 60 miles from Washington, DC.  With everything on one level, the property is the perfect family home, vacation getaway or home for empty-nesters or retirees.  The home has 180-degree views from the recently renovated large open floor plan with combined living, kitchen and dining rooms.  The modern combined kitchen and dining room with granite countertops, stainless steel appliances including a double oven and new tile flooring and is great for parties.  There is a large recreation room with plenty of potential that can be used as a 4th bedroom or home office.  There is new flooring throughout the majority of the home and crown molding in the living room and master suite. The refurbished living room has a beautiful marble fireplace. The waterfront facing side of the house has new windows and new sliding doors.
The outside has been recently re-sided in premium white vinyl shaker style siding and has multiple decks, both shaded and by the water with covered Tiki Bar for watching the sunsets.  It is perfect for entertaining or watching the children or grandchildren play on the beautiful lawn overlooking the Bay. The landscaping has been designed and installed by an award-winning Landscape Architect and includes well established plantings, flower beds, Japanese maples, crape myrtles and mature trees providing lovely shade during those hot summer months.  There are pavers stairs winding down to the white sand beach and the recently refinished 60-foot pier.  There is deep water and an electric10,000 lb. boatlift that was refurbished in 2021 as well as running water.  There are also two electric jet-ski lifts for water sports.  Crabs and fish are caught off the dock and oysters are currently grown in cages.  Bring your binoculars for the abundant waterfowl including bald eagles, osprey and blue herons.
22273 Saint Clements Avenue
Leonardtown, Maryland
  • 3 Beds
  • 2 Baths
  • 2,250 SqFt
  • 0.560 Acres
Under Contract-To Be Built: Quality Built Homes, Inc, The Fairfax 

***Meadows at Town Run is in the Town of Leonardtown, Special Tax Rate***
22064 Daffodil Court
Leonardtown, Maryland
  • 6 Beds
  • 5 Baths
  • 4,116 SqFt
  • 0.220 Acres
Under contract Lexington #3 (The Clarks Rest Model Home) which features over 3200sq. ft of above grade living space, including 5 bedrooms and 3 full baths above grade, with a large dining room, huge kitchen that opens right into the family room,  an in law suite/office on the 1st floor, plus a front porch to relax on with a stone watertable and partial stone front.   2nd floor provides nice size secondary bedrooms, plus a very welcoming owners suite, owners bath and owners closet. There is also a 2nd floor walk in laundry room featured with cabinets and built in linen. Basement is also fully finished, that will include a large rec room and full bath as well as an extra bedroom/den rea, plus a sliding glass door with concrete pad. Upgrades are throughout this previous model home with hardwood floor, quartz counters, tiled bathrooms, stainless steel gourmet appliance package, etc.. plus all kinds of electrical and low voltage add ones such as security system, surround sound, tv's, etc.. A large composite deck is also featured off the rear of the kitchen. 


Clarks Rest community features community pool, playground, basketball court, tennis courts, sidewalks and community clubhouse which can be rented out for private events. Community amenities are just a short walk away from the location of this home.
41309 Chestnut Hill Street
Leonardtown, Maryland
  • 6 Beds
  • 4 Baths
  • 4,280 SqFt
  • 0.180 Acres
Welcome to your dream home! Relax and enjoy breathtaking sunsets to help you relax and
unwind from your own deck. Did we mention sun, Solar Panels (PAID IN FULL) installed in 2018 that will cover 95% of your annual electric bill.  This impeccable home has five bedrooms, four full and 2 half baths in the highly sought-after Clarks Rest community in Leonardtown. An artistic touched well-maintained home with open concept layout, upgrades throughout and a soaring ceiling in the family room allowing for tons of natural light. The kitchen offers tons of cabinetry, granite countertops, and a large pantry! A full-size dining area with a panoramic view of the woods for peace and tranquility. An oversized backyard offers a screened in porch and open deck with minimal maintenance composite decking, and green grass for your family entertainment. The the first floor has your Owner's Suite with a complete spa-like bathroom featuring a large corner soaking tub, a shower with dual shower heads and two separate vanities. All bedrooms are sound proofed! Finished basement with natural sunlight flowing, rec room and a mother-in-law suite. Suite has a kitchen, full bath, and separate entrances to the inside as well as a rear entrance with patio. Tankless water heater, providing on demand hot water. Neighborhood amenities include community pool, playgrounds, basketball, tennis and volleyball courts, soccer fields, walking trails, tons of neighborhood events, & so much more! Excellent location in the highly sought-after Leonardtown schools. Close to amenities and a short bike ride to the downtown Leonardtown Wharf, restaurants, and shops. Do not miss this gorgeous 3,700+ fiinished sq ft home! You must see it to believe it.
23267 Clarks Rest Road
Leonardtown, Maryland
  • 5 Beds
  • 6 Baths
  • 3,700 SqFt
  • 0.300 Acres
** TO BE BUILT !!! *** Looking to build your dream home on a gorgeous lot? Here it is! Semi flat and over two and a half acres! The sunrises that you will see from your back yard will take your breath away! 
New construction home by Brooke Built Homes. Builder does NOT own this piece of property! Main picture of Boston model has upgraded brick front and other upgrades. Photos shown in listing are of previous builds and offer two different models by Brooke Built: The Boston and The Vegas.  The Boston offers a main level office or bedroom #5 with full bath. The Vegas offers a two story beautiful foyer.  Both floor plans offer a spacious Family Room and separate Dining Room.  Photos may display upgrades and additional features that are not included in this list price. Pictures shown do not reflect exactly the final product. Price may vary with different elevations. Finished square footage is approximate and may vary depending on customizations made by the purchaser. Price shown INCLUDES base house price with the lot. ** TO BE BUILT **
23920 Susies Lane
Leonardtown, Maryland
  • 5 Beds
  • 3 Baths
  • 2,800 SqFt
  • 2.640 Acres
This beautiful QBHI Preston model has all the best upgrades and is located on a rare pond view lot in the highly sought-out Leonard's Grant Community. This home was built for entertaining with more than 5000 finished square feet! Gourmet kitchen, with a stunning wood range hood, gas cooktop, large island, and updated appliances is open to the family room with gas fireplace.  In addition to the formal living and dining rooms, you can enjoy morning coffee, craft time, or private office/school space in the light-filled sunroom with tile flooring just steps off the kitchen.  This room adds substantial square footage to both the main level and lower level of the home.  The main level also boasts a massive mud room/laundry room off the 2 car garage that doubles as a pantry.  

When you’re ready to retire for the evening, head upstairs where the upper level boasts the primary suite with grand shower and soaking tub, a secondary suite with private bath, and two additional generously sized bedroom that share a full bath. If you’re not quite ready for bed, but looking to unwind then take a trip downstairs where you can enjoy some of the biggest basement spaces in the entire community – all boasting 9’ ceilings.  Plenty of room for everyone to play, watch TV, exercise, or just relax. Large rec room with wet bar and mini fridge, lead you toward your own private pre-wired movie room!  There is an additional bedroom suite, the biggest in the house actually, and full bath on this level as well.  Don't forget about storage - the owner's left plenty of space in the unfinished storage room with shelving.

Like new flooring throughout includes gorgeous acacia wood and tile on the main level, carpet on upper and lower levels.  All flooring has been replaced in the last few years and shoes were not worn in the house. Tankless gas water heater ensures nearly instant hot water access without wasting energy!

If you’re looking to enjoy the outdoors, this is the lot for you!  Large deck off the sunroom, stamped concrete patio from the lower-level basement entrance, fully fenced, raised planter beds, small firepit, backs to trees and pond.  Privacy, entertaining, play time – what more could you ask for?

Neighborhood amenities include community center, swimming pool, tennis/basketball courts, playground and large village green space. There are many community activities including a 5K fun run, food truck nights, movie nights at the pool, and many many more. Walking distance to Duke Elementary School and the new Leonardtown Library and Senior Center. No Front Foot/Deferred Water and Sewer Fee in this neighborhood! Great Leonardtown location close to historic Downtown Leonardtown of restaurants, shops and the Leonardtown Wharf. Short 25 minute commute to Pax River NAS.

Why wait on new construction when you can have this gorgeous home in no time!
23628 Belmar Drive
Leonardtown, Maryland
  • 5 Beds
  • 5 Baths
  • 5,451 SqFt
  • 0.240 Acres
Big, Bright and Beautiful Belmont model in Leonard's Grant Neighborhood.   This particular model was built with 2' rear and side extensions allowing for over 5000 sqft of finished living space with the full finished lower level.  Upon entering you will find the grand spiral staircase with open foyer, office or formal living area, formal dining room, gourmet kitchen and spacious family room.  There is a nice mud room/laundry room area off of the garage and a half bath.  Kitchen has beautiful maple cabinetry, granite countertops and stainless appliances.  Upper level boasts a huge primary bedroom with two large walk-in closets and deluxe primary bath with soaking tub and walk-in shower.  Three very generous sized bedrooms and full bath complete the upper level.  Lower level has 9' ceilings, media room pre-wires, 5th bedroom, full bath, play room/gym and walks out to a beautiful paver patio.  Combine the patio with the deck off the kitchen /family room, makes for great outdoor entertaining areas.   Neighborhood amenities include community center, swimming pool, tennis/basketball courts, playground and large village green space.  Just outside the neighborhood is Duke Elementary School and the new Leonardtown Library and Senior Center.  No Front Foot Fee in this neighborhood! Great Leonardtown location close to historic Downtown Leonardtown of restaurants, shops and the Leonardtown Wharf.  This home has so much to offer, you won't be disappointed.  Tenant occupied thru mid-June.
41437 Whimsical Court
Leonardtown, Maryland
  • 5 Beds
  • 4 Baths
  • 5,246 SqFt
  • 0.220 Acres
Under Contract-To Be Built: Quality Built Homes, Inc, The Ashland, Elevation A2 with 2.5 Car Front Load Garage in Meadows at Town Run.
22040 Daffodil Court
Leonardtown, Maryland
  • 4 Beds
  • 3 Baths
  • 0.410 Acres
A modern craftsman home with bonus room above! No Lot Included in this price (Add $170K for the Preserves lot)
buyers own the lot.  House has 4 bedrooms 3.5 baths - home has large kitchen, pantry, conditioned crawl space but large bonus room in upper level - 3 lots left in Big Chestnut - Call me and ask how we can build your dream home too!
40070 Green Tree Drive
Leonardtown, Maryland
  • 4 Beds
  • 4 Baths
  • 3,856 SqFt
  • 3 Acres
23522 Watervale Drive
Leonardtown, Maryland
  • 5 Beds
  • 4 Baths
  • 3,793 SqFt
  • 0.210 Acres

Maryland Waterfront ZIP Code List