Maryland Waterfront Homes for Sale 21619

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Featured Maryland Waterfront Homes for Sale 21619

This home is under construction and will be move in ready by July 2024!
Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis,  the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Photos are of similar home as this home is to be built.
224 Switchgrass Way 1831
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,600 SqFt
Escape from the hustle and bustle of city life to your private wooded 16+ acre Kent Island oasis. Located at the mouth of Cox Creek in Chester, delight in the tranquility with captivating views over the tidal wetlands into the Eastern Bay. Wildlife and outdoor enthusiasts will love the bountiful landscape. This gorgeous and beautifully maintained home exudes charm at first glance as you enter the horseshoe drive. With over 2,600 SQFT of living space, this 3 bed, 2.5 bath home features gorgeous panoramic views, skylights, open floor plan, main level primary suite, upper and main level bonus room/den, walk-in pantry, ample finished storage space, wrap-around deck, and more! The gorgeous wide-plank hardwood floors and hearth with wood-burning stove are reclaimed features from an old schoolhouse in Caroline County. The 2-bay garage has an attached space perfect for a studio or whatever you can dream up! Brand new septic system (2023) New Roof (2022) Home is being sold as-is. Don't wait, schedule a tour today! ***See uploaded documents for information on potential for marsh boardwalk/pier***
121 Gunners Rest Lane
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,686 SqFt
  • 16.280 Acres
This home is under construction and will be move in ready by July 2024!
Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis,  the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Photos are of similar home as this home is to be built.
224 Switchgrass Way 1834
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,600 SqFt
This home is under construction and will be move in ready by July 2024!
Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis,  the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Photos are of similar home as this home is to be built.
224 Switchgrass Way 1843
Chester, Maryland
  • 2 Beds
  • 3 Baths
  • 1,900 SqFt
This home is under construction and will be move in ready by July 2024!
Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis,  the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Photos are of similar home as this home is to be built.
224 Switchgrass Way 1842
Chester, Maryland
  • 2 Beds
  • 3 Baths
  • 1,900 SqFt
Your search is over!! This amazing 4 bedroom waterfront property in coveted Gibson's Grant is going to get lots of attention for a number of reasons: 1- Lot and location - Sprawling views of Macum Creek and the Chester River 2- Lots of updates including a custom on trend kitchen with huge center island, expanded deck and new outdoor bar/grill/kitchen 3-Dual waterside porches including a private covered porch off the primary suite perfect for enjoying your morning coffee or stargazing 4- Detatched heated garage with new epoxy flooring AND fully finished upper level is perfect for a man cave, office, living space or apartment and includes a full bath! Amazing community ammentities including pool, fitness center, playground and more! 
You won't want to miss this one! She is a beauty!!! SF does not include approximately 800SF for he finished space in detached garage***
223 Mchenny Court
Chester, Maryland
  • 4 Beds
  • 4 Baths
  • 3,400 SqFt
  • 0.170 Acres
Welcome to 2802 Cox Neck Road, nestled in the coveted Southwind community. This meticulously maintained home sits on over an acre of well-manicured land and offers picturesque views of the Crab Alley and the Chesapeake Bay.

Step inside to discover over 3,600 square feet of bright, comfortable living space. The main level features an open layout with a welcoming great room, formal living and dining areas, a bright sunroom, and two versatile offices. The well-designed kitchen and dining space also has access to a peaceful patio and the backyard. Upstairs, the spacious primary bedroom boasts a full bathroom, walk-in closet, and dual vanities. In addition to the primary suite, the home offers three additional bedrooms and two full baths and ample closet space. The upstairs landing offers beautiful views of the entryway and great room. 

The unfinished walkout basement provides an additional 1,810 square feet of potential storage or expansion space. The two-car attached garage offers plenty of room for vehicles and a work area. 

Southwind is a waterfront community with gorgeous views and access to the surrounding waters of Cox Neck Creek, Eastern Bay and Crab Alley Bay. Southwind offers residents access to a clubhouse, a small craft boat ramp, tennis courts, a nature trail and a boat storage area. The clubhouse is used for community events and celebrations. This community is conveniently located near Route 50, with easy access to Annapolis, Easton, Washington DC, Baltimore, and Saint Michaels. 

Experience the perfect blend of luxury and convenience at 2802 Cox Neck Road!
2802 Cox Neck Road
Chester, Maryland
  • 4 Beds
  • 4 Baths
  • 3,692 SqFt
  • 1.280 Acres
EXQUISITE comes to mind in this fabulous 3 bdrm, 4bath  Santorini Loft Edition. ALL OF THE UPGRADES that you could imagine PLUS! PREMIUM LOT that backs up to Cox Creek and the Kent Island trail are starters to this EXCEPTIONAL home. Let's start with the UPGRADES: CABINETS thru out the kitchen and baths, COUNTERTOPS, all APPLIANCES , TILEWORK thru out 4  BATHS, LVP FLOORING continuous on first floor, CENTRAL VAC with FLOOR SWEEP, TEN FT CEILINGS,TANKLESS WATER HEATER,WIFI EXTENDER, ALARM SYSTEM.22X11 SCREENED PORCH WITH GAS +TV HOOK UP.
Now let's talk about DESIGNER FEATURES!PLANTATION SHUTTERS Thru out, 7 CUSTOM CLOSETS, CUSTOM OFFICE CABINETRY like no other (beautiful), CEILING FANS, LAUNDRY RM!!!REMOTE CONTROL BLINDS on sliders. Second floor offers a full bath and bdrm along with a 9.5x35 sky basement for storage Finished oversize garage...this home is beautiful! All of this and resort style living featured KHOV.com
158 Sailcloth Way
Chester, Maryland
  • 3 Beds
  • 4 Baths
  • 3,494 SqFt
  • 0.180 Acres
This home is under construction and will be move in ready by July 2024!
Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis,  the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Photos are of similar home as this home is to be built.
224 Switchgrass Way 1833
Chester, Maryland
  • 2 Beds
  • 3 Baths
  • 1,900 SqFt
This home is under construction and will be move in ready by June 2024!
Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis,  the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Photos are of similar home as this home is to be built.
166 Warbler Way 31
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,602 SqFt
This home is under construction and will be move in ready by November 2024!
Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis,  the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Photos are of similar home as this home is to be built.
129 Wheelhouse Way 2021
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,601 SqFt
REDUCED $100k!!  A deep-water Cox Creek fixer with great "bones" isn't a home that comes up very often, but here it is! Do a little, or do a lot, as this is a true 1968 time AS-IS time capsule that feels solid under its beautiful hardwood floors. With 5+' water depth and a beautiful view of the creek, your investment will be solid either way. The home is connected to the original septic system, but a sewer tap with a PAID-FOR tap fee is available on-site. Don't miss this one as it is sure not to last long! Note that there is a plotted view lane on the property designed to protect the view of 310 Benton's Pleasure Rd that is included in the documents available to the Buyer. Two adjacent building lots to the right are also for sale.
306 Benton's Pleasure Rd
Chester, Maryland
  • 4 Beds
  • 3 Baths
  • 2,793 SqFt
  • 1.640 Acres
This home is under construction and will be move in ready by July 2024!
Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis,  the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Photos are of similar home as this home is to be built.
224 Switchgrass Way 1821
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,602 SqFt
Elegance abounds in this fabulous  3 bedroom, 3 full bath home.  Coastal inspired vibes resonate throughout the home with many upgrades that include but are not limited to; quartz countertops in kitchen and baths, 9' sliding glass door at the dining area, screened porch/lanai area, gourmet kitchen layout, upgraded cabinetry, pendant and under counter lighting, upgraded carpet and padding throughout the loft area.

Four Seasons Community offers resort style living right here in Maryland.   Clubhouse, party rooms, fitness center, pool, pickle ball, tennis, bocce courts, marina and much more.  clubhouse is open for tour 9-5 pm daily.

Please see movie camera icon for video and please see the paper icon for documents inclusive of floor plan, cable and internet upgrades and upgraded features of this home.
316 Bayberry Drive
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 3,274 SqFt
  • 0.170 Acres
This home is under construction and will be move in ready by June 2024!
Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis,  the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Photos are of similar home as this home is to be built.
166 Warbler Way 44
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,602 SqFt
PRICE DROP!!!  A must see in the sought after community of Four Seasons at Kent Island on the Eastern Shore of Maryland.  Why wait for new construction when this fabulous Santorini w/Loft model is awaiting it's next owner.  Located just minutes from the Chesapeake Bay Bridge with easy commutes to Annapolis, DC, Baltimore or beaches on the Atlantic ocean, you don't want to miss this home.
This 3 bedroom,4 bath home with many desirable features was enhanced with the meticulous desires of the current owner.  Among the normal expectations of a quality built home including upgraded counters, stainless appliances, upgraded cabinets, upgraded flooring, tankless water heater and gas cooktop, the current owners have also enhanced the kitchen with additional shelving in the cabinets, added ceiling fans through the home including a 60" ceiling fan in the loft, added shelving to the owner suite and second bedroom closets, added matching cabinets and counter to the Great Room along with shiplap and shelving and added a 7' closet to the laundry room. The Garage was upgraded with insulated walls & ceilings, finished walls and paint, 9' cabinets and bases, pegboard and additional electrical outlets.  The Sky Basement measuring 10'x40' for additional storage was also upgraded with insulated walls and ceiling along with finished walls and paint and baseboards and trim.
For additional entertaining and enjoyment, a 15'x32' patio was added to the rear of the home along with railings and electrical outlet for a grill.
Upgrades in this home total over $60,000 and will definitely be seen and felt and you tour and eventually live in this home.
103 Spinnaker Way
Chester, Maryland
  • 3 Beds
  • 4 Baths
  • 3,299 SqFt
  • 0.280 Acres
This budget-friendly waterfront ranch-style home on Crab Alley Bay in Kent Island offers stunning views of diverse wildlife, including ducks, swans, and geese. The residence showcases an open floor plan with three distinct living spaces. Upon entering, you'll find a formal dining or living room adorned with a bow window. The journey continues into the kitchen with tile floors and table space overlooking the water, seamlessly connecting to the family room and sunroom. The family room boasts new carpeting, a gas masonry fireplace with a raised hearth, mantel, and built-in shelving. The 20x20 sunroom is designed with floor-to-ceiling glass to maximize waterfront views and features its own heating and air system, along with white burber carpeting. The spacious primary bedroom suite, along with two additional bedrooms, also showcases new carpeting. Completing the property is an oversized 2-car garage and a shed. Marling Farms, the community in which the home is located, provides residents with four beaches, three boat ramps, two piers, two kayak racks, a fishing pier, playground, ball fields, picnic pavilion, and various community gatherings. The home has a choice of oil heat or heat pump.
1518 Saint Marys Road
Chester, Maryland
  • 3 Beds
  • 2 Baths
  • 2,000 SqFt
  • 0.460 Acres
This gorgeous Santorini model is Move In Ready and located in the amenity rich 55+ community of Four Seasons. Built in 2019, this home provides a spacious floor plan offering approximately 3200' of living space.  The Awesome Gourmet Kitchen provides an oversized island with plenty of seating and Quartz Countertops, lots of cabinet space with under cabinet lighting, lovely walk-in pantry, top of the line appliances including a 5-burner gas cooktop, a counter depth refrigerator and double (His & Her?) ovens.  Generously sized family room is crowned by an elegant gas fireplace that is not just a pretty focal point but an effective heat source with blower to keep you toasty warm. This Santorini model features dual primary bedrooms on the main floor.  Both with private baths and large walk-in closets.  There is a 3rd full bath on the main level with a jetted walk-in tub!  Upstairs the 2nd level provides a 3rd bedroom, a 4th full bath plus a 2nd Family room that could be the optional space you seek.   Glass French doors give privacy to the downstairs office. There is also a separate formal dining room and the Laundry is on the main level too. Love the screened porch and Trex deck.  Both are great options for relaxing or entertaining.  An oversized garage will park 2 cars with space to spare.  This community offers a Resort-style, amenity rich experience. Residents @ Four Seasons can take advantage of the community's spectacular 24,000' clubhouse.  There are 2 pools, one inside and one outside, a state-of-the-art fitness center, multiple tennis and pickleball courts, a reading room, a party room, a Billiards room plus more.  A full-time lifestyle director is on site.  The Kent Island Four Seasons also features a well-maintained calendar of activities and has a full-time lifestyle director on site.  Located steps from the water and has quick access to Rt. 50.
119 Cavalier Court
Chester, Maryland
  • 3 Beds
  • 4 Baths
  • 3,200 SqFt
  • 0.170 Acres

Maryland Waterfront ZIP Code List