Maryland Waterfront Homes for Sale 20650

Find the best Maryland Waterfront Homes for Sale 20650. Get help from Frank Rosati, a top real estate professional with over 15 years proven track records.

Featured Maryland Waterfront Homes for Sale 20650

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
A Breton Knolls exclusive offering. Be the first to call this to-be-built custom-crafted home yours! Located in the heart of Leonardtown on oversized lots, this new 24-lot subdivision offers an elegantly crafted home by a well-known local builder. The Jackson floor plan perfectly combines the essence of a Colonial Farmhouse with a modern twist to include over 3,000 sqft of living space spread throughout four bedrooms and three levels - ideal for a busy lifestyle and entertaining. Sunlight, hardwood flooring, and coffered/tray ceilings fill the floor plan with endless options for customization available. 

Imagine filling your home with savory scents from the bump-out kitchen with cathedral ceilings and finishes of your choosing. The kitchen gives way to the larger-than-life living room with soaring two-story ceilings and a shiplap and stone surround fireplace with a show-stopping Amish mantle - the perfect spot for mementos. The Jackson floor plan also offers a sophisticated main-level primary suite designed to evoke utter tranquility with a walk-in closet and spa-like bathroom. Additional amenities included at the base price include a water table stone front exterior, black windows, black gutters, stone piers grounding the front porch, an 8-ft front door, and much more. The Jackson floor plan in Breton Knolls starts at $774,000, with a list of customizations and add-ons available upon request.
25265 Ledgewood Way
Leonardtown, Maryland
  • 5 Beds
  • 5 Baths
  • 4,500 SqFt
  • 1.130 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
This Majestic 5 Bedroom, 3.5 bath Colonial located in the prestigious neighborhood of AVENMAR boasts over 4800 square feet of finished living space on over 4 acres of land providing a private park like  outdoor setting. 

Whether you opt to spend time by the fireplace in the open concept kitchen/living area or serving a more formal meal in the private dining room, the gourmet kitchen with pass through Butler's pantry will make entertaining a dream.  The large office is perfect for teleworking, studying or just spending a quiet afternoon with a good book.  The convenience of a main floor half bath, laundry room and entry through the attached garage make this home perfect for a busy household.   This home also had a NEW ROOF installed in 2021.

Upstairs you will find the Primary Owner's suite which features a large personal sitting area and access to a private deck overlooking the rear of the property.   The en suite bath has a large soaking tub, separate shower, water closet and two exceptionally sized walk-in closets.  Three additional large bedrooms are located on this level and share a full bath. 

The lower level of the home boasts a fifth bedroom with a large den, living area and full bath making it  perfect for potential in-law suite.

Spending time outdoors on the deck, grilling on a nice evening or following fairy lights to a secluded sitting area make this property fun and relaxing.  If you like to be active you can either use the trails on your own private 4.11 acres or venture out into the community.  Featuring stables offering both boarding and lessons, playground, volleyball court, tennis courts, walking trails, community dock/boat launch and kayak racks, there is truly something for everyone!  The Community Clubhouse with pool is available for hosting private events and has an attached Condo which owners may rent for short term guests.  If you love to spend an afternoon on the links, Breton Bay Golf Course and Country Club is just down the road. 

With close proximity to local shopping, schools, and  restaurants, including the Port of Leonardtown Winery,  Downtown Leonardtown Shopping, Dining and Entertainment District, PAX River NAS, College of Southern Maryland and St. Mary's College of Maryland, this home is a MUST SEE!  Call to schedule a showing today!
22676 Chickadee Lane
Leonardtown, Maryland
  • 5 Beds
  • 4 Baths
  • 4,804 SqFt
  • 4.110 Acres
Big and Beautiful home in Leonard's Grant!  Located in the back of the neighborhood with the house backing up to trees.  Enter inside to the 2 story ceiling with huge windows that look out to the trees and bring in natural light.  This 5 bedroom home has nice size bedrooms and a very large primary suite.  It is upgraded with a custom bath and a custom closet.  Laundry is situated outside of the primary bedroom and has built ins to stay organized.  The main floor has an office, dining room, bedroom , 1/2 bath and a great room that opens to the gourmet kitchen.  The basement has a lot of space and a bedroom with a full bath.  It is set up as a theater room and walks out to a patio on the same level as the pool.  
Gorgeous screened in composite deck with attached uncovered deck that heads down to the AMAZING pool. Salt water Pool and Composite Deck installed in 2019.    The pool is 3 ft in the shallow end and reaches 6'3inches in the deep end.  It is fiber glass and has a custom pool cover that is very strong.  Take some time to check this beautiful, spacious home out!
23761 Coventry Drive
Leonardtown, Maryland
  • 5 Beds
  • 4 Baths
  • 4,293 SqFt
  • 0.290 Acres
Welcome home to this lovely cape cod which sits on 3 secluded acres of land. The expansive covered porch extends the length of the house in the front to greet you upon arrival. Multiple entries to include "mudroom" off garage with 1/2 bath and large pantry.  The foyer is inviting and warm and showcases a beautiful staircase. The dining room and formal living room/office flank the foyer in the front of the home.  Hardwood flooring  throughout most of main level to include foyer, dining, formal living/office, great room and primary bedroom. High ceilings continue the expansive feel of this sprawling first floor.  Not shy on cabinetry as it goes to the ceiling, this kitchen is just wonderful, oversized with island and breakfast area and open to nearby great room. The great room is filled with natural light and the warmth of a stone fireplace.   Large  primary bedroom on main floor with a large walk-in closet. Primary bath has dual vanities, separate water closet, stand alone shower and large tub. The laundry room is located just outside the primary bedroom for ease and convenience., as well as a full bath.  The upstairs is home to two large bedrooms and another full bath, as well as the balcony, overlooking the main level. Don't miss the two additional storage areas upstairs. Either or both could be finished for a playroom or craft area? The  garage is huge, with two separate bays and a large inside work area, as well as additional storage closets.  Perhaps the hidden treasure can be found above the garage. A mother-in-law apartment/guest quarters fills the entire area above the garage. Separate living/kitchen combo with private bedroom and bath. Apartment also has its own washer and dryer and large closet. Apartment furniture can convey with sale.  The very private backyard offers the opportunity to entertain on covered  expansive back porch or spill over to the large patio.  This is the spot to sip morning coffee and unwind after a hectic day. 
Know the big ticket items have been taken care of-new roof in 2017, new heat/ac in apartment and house in 2019,  crawlspace just completed in 2023.  Did I mention the driveway is paved?! The shed will convey as well as its gardening contents. No HOA so bring all your toys. Simply not enough great words to describe this property. You'll want to schedule to see this one!
20102 Whippoorwill Lane
Leonardtown, Maryland
  • 4 Beds
  • 5 Baths
  • 3,785 SqFt
  • 3 Acres
Here's a chance to live in popular Breton Bay - across the street from the Breton Bay golf course/country club, just steps away from the community association beach/pier ($75/year) and around the corner from a private marina.  Wonderful corner lot with mature weeping willow & crape myrtle trees, seasonal water view of Cherry Cove, and a stately brick front colonial with plenty of room to spread out.  The home features 5 bedrooms/5 full baths (5th bedroom on main level optionally used as private library/study), finished walk-out basement, Trex deck off kitchen w/hot tub, wood and new carpet flooring, and spacious main level living space.  You'll find the family, living, dining rooms + remodeled eat-in kitchen, 5th bedroom/study, full bath and laundry on main level.  Upper level features an enormous primary en Suite bedroom plus 3 additional large bedrooms and 2 full baths.  The lower level has large a rec/game room,  additional flex room and full bath, and sliders opening to the back yard with shed.  HSA Home Warranty. 
 This is a great place to call home!
21715 Pebble Beach Court
Leonardtown, Maryland
  • 5 Beds
  • 5 Baths
  • 4,437 SqFt
  • 0.700 Acres
Under Contract-To Be Built: Quality Built Homes, Inc, The Fairfax 
Fairfax A1 Model, , 16x12 Built-in porch, Additional windows through out, coffered ceiling, hardwood stairs, first floor in-law suite; full bath & walk-in closet,  Upstairs 4 bedrooms, primary bedroom includes angle trayceling, sitting room, two walk-in closets, and large 7x4.5 tiled shower with two shower heads, recessed lights, seat, ledge & shelf.  Huge laundry room.  Hall bath has double vanities and tub/shower combo with rec'd light & addt'l window.  Lower Level Finished Basement with LL Bedroom and large bathroom.  

***Meadows at Town Run is in the Town of Leonardtown, Special Tax Rate***
23086 Town Run Drive
Leonardtown, Maryland
  • 6 Beds
  • 5 Baths
  • 0.210 Acres
This is a to-be-built planned homesite and purchaser will have the ability to customize their interior finishes in our Home Gallery design center! All structural options are included in the price and cannot be changed. Features of this Yorktown home include: great Room with fireplace, spacious kitchen with 16'x12' sunroom that walks out to a covered deck, a fully finished basement with 5th Bedroom and full bath with walk out basement ground level. Enjoy the 2nd level loft, the owner's suite has an upgraded deluxe shower with walk in closet. A 3-car garage is also included. Clark's Rest boasts a range of resort-style amenities, including a clubhouse, pools, sports courts, playgrounds, walking trails and more. The neighborhood’s prime location also offers close proximity to the notable schools, unique shops, art galleries, dining and waterfront attractions of historic Leonardtown, as well as convenient commutes to Washington D.C., Alexandria, Waldorf and major employers such as Pax Naval Base. Sales centers are OPEN but visitors are encouraged to call ahead to be guaranteed a dedicated appointment. Virtual appointments are available as well. Photos are of similar model home. Contact builder for current incentives. Final price contingent on options & subject to change.
41444 Heritage Lane
Leonardtown, Maryland
  • 5 Beds
  • 4 Baths
  • 4,779 SqFt
  • 0.150 Acres
Welcome to Leonard's Grant!  This Quality Built home has all the bells and whistles including those you didn't even know you wanted! With over 3700 sqft of living 5 bedrooms, 3.5 baths on 3 finished levels.  The foyer with hardwood floors invites you in where you'll find the formal living room and dining room well lit with windows all around, the kitchen boasts a large island, soft close cabinetry with double ovens and a cooktop also a new fridge, microwave and dishwasher.  The family room is cozy with a gas fireplace and room for everyone.  You'll appreciate the mudroom that attaches to the garage to store shoes and coats before entering the home too.  Upstairs are 4 spacious bedrooms, walk in closet and spa like bathroom in the primary and the finished basement has that 5th bedroom and full bath for guests.  Entertaining is easy with the theater room and doors to the backyard.  Once outside you'll marvel at the 3-5.5 foot deep inground pool, deck, cornhole area and shed for extra storage.  The solar panels are leased but your payment is worth every penny you save on your electric bill, hundreds a month! December's electric bill was less than 10 dollars!  And as if that isn't enough the community offers it's own pool and recreation area, walking distance to a newer school and just minutes to fun and historical Leonardtown.
23608 Margrave Drive
Leonardtown, Maryland
  • 5 Beds
  • 4 Baths
  • 3,712 SqFt
  • 0.230 Acres
This beautiful, like new  home is ready for your family to call their own. Hardwood flooring throughout much of the main level. Lovely kitchen with huge kitchen island and loads of cabinetry. Stainless appliances, granite counters and large pantry round out the space. Separate dining room off kitchen allow for more formal gatherings, while the breakfast area and living room provide open concept living to kitchen. The primary bedroom and bath are on one wing of the house while two other bedrooms and full bath fill the opposite wing. Enjoy the privacy of the screened porch overlooking the backyard while you catch your breath from a busy day.  The garage is two car, front load and brings you to the large laundry room and drop zone complete with bench and hooks. Newly finished basement has a large living area, bedroom and large full bath. A wonderful unfinished space in the basement allows room for holiday decorations, suitcases and workout equipment to round out this hard-to-find rambler. Professional photos to follow this week as well as professional cleaning.
43011 Bluejay Lane
Leonardtown, Maryland
  • 4 Beds
  • 3 Baths
  • 2,306 SqFt
  • 0.210 Acres
This beautiful 2018 Lexington model has a 2 car rear load garage with a 12' extension, and was built to impress.  You cannot help but notice the beautiful lawn when you drive up. The grass is lush and the home shows pride of ownership.  Lovely hardwood flooring throughout the entire main level, with the exception of vinyl flooring in the half bath.  The great room is huge and provides the coziness and warmth of a gas fireplace. The expansive kitchen with upgraded cabinetry will not disappoint. Graphite appliances, granite counters, gas cooktop, a beautiful deep farm sink and  a huge island make this lovely kitchen a chef's delight.  Enjoy the benefit of the separate coffee bar and very large pantry just around the corner. The guest suite with private bath on the main level offer the perfect spot for your in-law suite or private study.  The upstairs is home to four bedrooms and a hall full bath with two sinks. The primary bedroom has its own sitting area. The primary bath is  large with a rounded wall of glass at the shower. Two sinks and a large walk in closet are the finishing touches on this great space.  No need to lug laundry up and down the steps, as the oversize laundry room is on the bedroom level, and includes a laundry sink. All bedrooms are prewired for fans and the home has a central vacuum system. There is loads of room in the basement to spread out and enjoy the  large family room. The sixth and final bedroom and full bath are located in the basement as well.  9' ceilings on the 1st and 2nd floors with 8' ceilings in the basement. The mechanical room  provides additional great overflow storage. The maintenance free deck with vinyl railings is host to the ideal entertainment area. This home's fully fenced backyard adds both privacy and safety for children and pets alike. The stamped concrete patio under the deck is yet another great outside spot to enjoy. To the right of the driveway you will find the storage shed wired with electric. Know the home has also had a generator switch installed and is prewired for a hot-tub, should you choose.  Also, washer, dryer and pool table can convey.  There is simply not much these owners have left undone. Why wait for new construction when this lovely home can be yours before the new year is rung in! Community center with pool, playgrounds and basketball hoops make this an ideal family destination! Come give us a look! 
Seeking Veterans....this home has a VA assumable loan with a 2.875 rate!  Additionally, sellers are offering $10k painting/carpet allowance with acceptable offer.
41435 Osborne Lane
Leonardtown, Maryland
  • 6 Beds
  • 5 Baths
  • 4,145 SqFt
  • 0.180 Acres
Spacious one level Living open floor plan, with 3 Bedroom and 2 full Baths, upgraded Gourmet kitchen with Luxury Vinyl Planks flooring through out the first floor, kitchen has upgraded quartz counter tops and oversize kitchen island with upgraded kitchen cabinet and lighting through out the home,  owner bath has Deluxe Shower with upgraded tile on wall and floor. Walk out the Great Room to a 16'x10' Composite Covered Deck with stairs to grade. 2 Car Garage with openers, alarm system and much more.. unfinished full basement with 3 pc rough in -
23278 Applewood Lane
Leonardtown, Maryland
  • 4 Beds
  • 4 Baths
  • 3,900 SqFt
Beautiful new listing in Leonard‘s Grant!  You’re not going to want to miss this home with a fabulous layout, on the corner lot! Location is a prime spot! This house has an extremely large, first floor primary bedroom that is located off of the kitchen. The bathroom is equipped with two separate sinks, a garden tub and a large, upgraded shower with glass doors. This gourmet kitchen is one that people dream of…Upgraded stainless steel appliances, including a Bosch dishwasher! Take your food to eat at the bar, the patio, right off the kitchen or the dining room! Dining room is spacious with gorgeous pillars. The main floor also boasts a study surrounded by two sets of double French doors, head out of the study and you’ll see the powder room and the first floor laundry. The second floor of this home has another living area and three bedrooms. In between two of the bedrooms, you will see the buddy bathroom. The basement of this home is absolutely enormous and has unlimited potential! It is currently unfinished, but has a rough in for a bathroom. This can easily be finished with a bedroom, bathroom, hang out area and still has room for an unfinished storage area!
41429 Challedon Way
Leonardtown, Maryland
  • 4 Beds
  • 4 Baths
  • 3,660 SqFt
  • 0.220 Acres
UNDER CONTRACT***TO BE BUILT***Ashland Elevation A1, Finished LL, Screen Porch, & Deluxe Kitchen
22070 Daffodil Court
Leonardtown, Maryland
  • 3 Beds
  • 2 Baths
  • 0.210 Acres
Looking for a great home on a great lot in a high desired school district?  At Five beds , three full and one half baths and just over 3800 square feet sitting on almost 5.5 acres of private  land this home will allow you to escape the the daily grind and relax.  

Enter into the home from the covered front porch into the bright foyer.  Flanking the foyer is the formal dining room and cozy library.  Follow the hallway back to the family room, open kitchen and the breakfast room overlooking the wooded back yard.   The rear of the home also accesses the back deck and the rear yard of the home.   Additionally on this level you will find the owner's suite with double vanity large owner's closet, and a separate soaking tub and shower.  

The upper level of the home features 4 bedrooms all with a shared hall bath.  These bedrooms were utilized by the owner's family while they were growing and provide ample space for growth.  

The basement level provides wide open spaces with a full bathroom and is currently set up in a pub style for entertaining.  This is the perfect place for all your celebrations.  

The community offers large lots for privacy and a great community playground. Also there are community fields for community members and guests to play all their favorite sports and game. 

Centrally located in Leonardtown this home is just minutes from Pax NAS, downtown Leonardtown, Solomons Island, and various state and local parks.
20488 Deer Wood Park Drive
Leonardtown, Maryland
  • 5 Beds
  • 4 Baths
  • 2,774 SqFt
  • 5.400 Acres
***House to be built**Under Contract**Lancaster House Style****  Located in Leonardtown, Maryland, The Meadows at Town Run offers 107 homesites and a variety of one and two-story floor plans to choose from.  This community provides easy access to Pax River Naval Air Station, and is conveniently situated for commuters traveling Route 301, Route 4, and Route 5. A quaint wharf town with rich colonial history, Leonardtown has undergone a remarkable revitalization over the past two decades. Shopping, dining, and recreation options abound in the Arts & Entertainment District, with numerous family-friendly events throughout the year. Meadows at Town Run is in the Town of Leonardtown, Special Tax Rate Applies.  QBHI is an Energy Star Builder.  $7,500 in closing help with use of one of QBHI’s preferred lenders and title company. On-site Model Home Open Tuesday to Saturday, 11-5 (Closed Sunday & Monday).  Call to schedule an appointment to tour today or stop on by…lots are going quickly.
22076 Daffodil Court
Leonardtown, Maryland
  • 4 Beds
  • 3 Baths
  • 3,055 SqFt
  • 0.210 Acres
LOVINGLY UPDATED COLONIAL NESTLED IN A BEAUTIFUL PARK-LIKE SETTING ON .65 ACRES IN DESIRABLE BRETON BAY!  COMMUNITY AMENITIES AVAILABLE POOL, TENNIS COURTS, GOLF COURSE, BEACH, MARINA ALL AVAILABLE AT REASONABLE RATES.   AWESOME FIRE PIT AREA WITH BUILT-IN GRILL.  RECENT UPDATES/IMPROVEMENTS INCLUDE ALL BATHROOMS, FLOORING, PAINT, SS APPLIANCES, ROOF AND MORE!  SPACIOUS OPEN FLOOR PLAN WITH HUGE KITCHEN AND PLENTY OF CABINETS AND COUNTER SPACE, LOVELY PANTRY AND NEW SS APPLIANCES.  SEPARATE BREAKFAST AREA, SUN ROOM AND LARGE LIVING ROOM WITH BUILT-IN ENTERTAINMENT/STORAGE AND BREATHTAKING WOOD-BURNING FIREPLACE.  1ST FLOOR OWNER SUITE HAS DOUBLE CLOSET AND FULL BATH.  THERE IS A HUGE OFFICE/DEN/PLAY ROOM; HOWEVER YOU WANT TO USE IT!  2ND FLOOR HAS A SECOND OWNERS SUITE WITH A WALK-IN CLOSET AND FULL BATH, A HALL BATH, 2 MORE BEDROOM, PLAY ROOM/OFFICE AND A LARGE FLEX SPACE.  SO MANY OPTIONS!
40794 Lake And Breton View Drive
Leonardtown, Maryland
  • 4 Beds
  • 4 Baths
  • 2,854 SqFt
  • 0.650 Acres

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