Maryland Waterfront Homes for Sale 21619

Find the best Maryland Waterfront Homes for Sale 21619. Get help from Frank Rosati, a top real estate professional with over 15 years proven track records.

Featured Maryland Waterfront Homes for Sale 21619

Protected waterfront on Cox Creek. Blue Heron II to be built.
Personalize this home to your taste.
3 story with waterfront decks, luxury finishes, and more.
Join us to enjoy the Eastern Shore lifestyle just 10 minutes to the Bay Bridge.
1757 Harbor Drive
Chester, Maryland
  • 4 Beds
  • 3 Baths
  • 0.550 Acres
This special Gibsons Grant Coastal Contemporary backs up to the Community  Open Space and Waterfront.   Perfect!    Awesome double sand bar creates a calm pooling of water to get your toes wet while also creating a sandy beach area. Relax and watch nature change day to day!  Now come enjoy the scenic water views from inside this custom home.  Love this floor plan! Spacious gourmet kitchen and family room are open and connected by the over-sized island with seating.   Both are filled with light and the family room is further enhanced with a gorgeous stack stone gas fireplace.  There is a separate  dining room and a good sized main level office plus 2 covered waterside porches. Fabulous!  Lovely hardwood floors and  moldings run through out most of the main level.  Excellent fit and finish with attention to detail.  Perfect waterside owners suite offers a large walk in closet, a sitting/dressing room with more closet space and provides private access to the 2nd floor waterside porch.  Additionally, the owners bath has a walk in shower, soaking tub and  double sinks.   A separate staircase leads to the private 4th bedroom.  It is a spacious room and a great space for an au paire or guest suite or teenagers get away/moms get away/dads get away, theater room, etc. This versatile room has its own heat and air and access to lower level full bath.  2 car attached garage and  fenced court yard complete this special property.   Gibsons Grant has fabulous community amenities including:  heated pool, clubhouse with party room, fitness center, multiple pavilions, fishing pier and kayak launch.  Convenient to Bay Bridge for easy commute and just minutes from waterfront dining, golf courses, marinas, shopping and all the shore has to offer.
154 Carriage Heath
Chester, Maryland
  • 4 Beds
  • 3 Baths
  • 2,771 SqFt
  • 0.150 Acres
Just in time for summer to enjoy your fresh catch off your private pier! You will love the convenience, location, and waterfront lifestyle of this beautiful Chester home.

Located along Cox Creek, this light-filled custom-built home features hardwood floors, an open main level floorplan, updated kitchen, attached 1.5 car garage, main level laundry, gas fireplace, and five bedrooms on the second level. The primary bedroom is complete with cathedral ceilings, an extra-large walk-in closet and Cox Creek views! The primary bathroom includes double vanities, soaking tub and separate shower. The large fifth bedroom with storage closet could be used as additional family room/rec space or home office.  

Enjoy entertaining on the large waterside deck or take in the peaceful views of Cox Creek while relaxing in the hot tub. The private, well maintained L-shaped pier includes an 8,000lb boat lift, floating jet ski dock, and manual kayak lift. St. Michaels and Annapolis are just a short boat ride away. 

Harbor View is conveniently located to Route 50 and the Bay Bridge, nearby shopping, dining, entertainment, parks and trails, Annapolis (17 miles), BWI Airport (35 miles), and Baltimore (39 miles). Easton/Oxford and St. Michaels are just 30/40 minutes away! 

This home is the complete waterfront package with something for everyone!
2613 Cecil Drive
Chester, Maryland
  • 5 Beds
  • 3 Baths
  • 2,496 SqFt
  • 0.450 Acres
The Seahawk is a stunning waterfront home designed to take advantage of the waterfront views.  Take care of two dreams at once with building a new home and living on the waterfront. You also can build a pier with permit a 108 feet of waterfront.  This home has a open floor plan on the main level and the floor plan, really cant get much better then this one for waterfront.  Great location central to shopping, church, bay bridge and at the same time feel like you got away from it all!

(See current builders plans for price out and up grades, Lot to be purchased separately see Bright for listing) Upgrades are available throughout the home including a gourmet kitchen, sunroom, a flexible room that could be a home office, first floor master, or in-law suite, and decks on every level. The plan starts at 2,755 sq. ft. with options to expand up to 4,425 sq. ft. up to 5 bedroom and 5 baths possible. The Seahawk  allows you to choose from multiple second floor layouts to personalize the home for your family. An optional 3rd floor loft and deck provides even more space for entertaining or just enjoying a quiet sunset or nature on the river.
Lot 31F Parks Road
Chester, Maryland
  • 4 Beds
  • 4 Baths
  • 2,775 SqFt
  • 0.680 Acres
109 John Gibson Drive
Chester, Maryland
  • 6 Beds
  • 5 Baths
  • 4,165 SqFt
  • 0.170 Acres
IN-LAW SUITE/COMMERCIAL!!! 4,227 sq feet Residential/Commercial Mixed Use Town Center.  Public Sewer. A must see!! The main house has 5 bedrooms and 2.5 full bathrooms and 1 bedroom 1 bath full kitchen separate.  Front rental is separately metered, currently rented residentially,  is zoned for commercial use (TC Zoning). Great opportunity for a business or for someone looking for an in-law suite. From granite and stainless steel appliances in kitchen to upgraded bathrooms this open floor plan provides multiple living areas. Master bedroom has its own private full bath with soaking tub and separate shower. The third level has its own bedroom and living room!! Two car side load garage and extremely private deck. Vinyl fully fenced side yard and large front porch!! Don't miss this opportunity to purchase a property where you can offset your mortgage with a tenant or have your small business.
1618 Postal Road
Chester, Maryland
  • 6 Beds
  • 4 Baths
  • 4,227 SqFt
  • 0.270 Acres
Under construction and move in ready in 2022!
The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony.  The building has elevator access, 1 car garage and secure storage room per unit. Just a short walk or drive to the incredible 24,000 square foot owner's clubhouse opening summer 2022! 
Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, resort-style experience less than 25 miles from Annapolis and within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse, indoor and outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site, Four Seasons at Kent Island also features a well-maintained calendar of activities and classes from yoga sessions, to paddle boarding  or walking club. 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. Four Seasons at Kent Island 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. Call today to find out the details and start living the life you want. *Pictures represent a model home as this current home is under construction.
170 Harrier Way 44
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,600 SqFt
This quick move in home will be available in Spring 2022. This luxurious home will sit on a premium homesite backing to trees and features many designer upgrades. The centerpiece of the home is a gourmet kitchen with gas cooking, tile backsplash and quartz countertops. The adjoining  great room includes a cozy fireplace and the flooring has been upgraded throughout the first floor and all baths. Call today to to visit and learn more. 

Welcome to the premier active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and luxury condominiums. Discover an amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents will soon be able to take advantage of the community's 24,000 sq. ft. clubhouse with, indoor and outdoor pools, billiards, ballroom, a state-of-the-art fitness center, and yoga studio, and multiple tennis & pickleball courts. With a full-time lifestyle director already on site, there is always something for you to enjoy along with neighbors, friends and family. The community lifestyle is designed into a well-maintained calendar of activities such as outdoor yoga sessions, pickleball lessons, kayaking, paddleboard, mahjong tournaments, virtual book club and other socially distanced activities.  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, Four Seasons at Kent Island 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.
193 Spinnaker Way
Chester, Maryland
  • 4 Beds
  • 3 Baths
  • 2,862 SqFt
  • 0.120 Acres
IMMEDIATE MOVE-IN HOME - No waiting on new construction to move into this popular community. Please schedule a walk-through to learn more.

Two bedrooms, two baths and half, plus an office/rec room or bedroom usage if needed, two-car garage, masonry/stone fenced backyard with stainless steel built-in grill. This open floor plan formal dining room, kitchen with eat-in kitchen area and family room allow for fun entertaining with a large island and plenty of counter space. This space opens to a sitting area on the screened-in patio to the masonry/stone-fenced backyard... great for entertaining. Enjoy this gourmet kitchen with gas cooking, a tile backsplash and granite countertop, and a spa walk-in shower.

It's located in the well sought-after active adult 55+ community and within walking distance to the popular Maryland Chesapeake Bay.  You will be within 45 miles of Washington DC and Baltimore. The charming atmosphere of the Four Seasons at Kent Island is perfect for tranquil evening walks,  a casual bike ride, local shopping, and Maryland's best seafood restaurants. This resort home is family and pet-friendly and full of fun amenities. You will soon be able to take advantage of the community's 24,000 sq. ft. clubhouse with, indoor and outdoor pools, billiards, a ballroom, and a state-of-the-art fitness center.

The community lifestyle is designed into a well-maintained calendar of activities such as outdoor yoga sessions, pickleball lessons, kayaking, paddleboard, mahjong tournaments, virtual book club, and other activities. 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. Schedule an appointment tour today!
112 Saltworks Drive
Chester, Maryland
  • 2 Beds
  • 3 Baths
  • 2,438 SqFt
  • 0.170 Acres
This quick move in home will be available in Spring 2022. This luxurious home will sit on a premium homesite backing to trees and features many designer upgrades. The centerpiece of the home is a gourmet kitchen with gas cooking, tile backsplash and quartz countertops. The adjoining  great room includes a cozy fireplace and the flooring has been upgraded throughout the first floor and all baths. Call today to to visit and learn more. 

Welcome to the premier active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and luxury condominiums. Discover an amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents will soon be able to take advantage of the community's 24,000 sq. ft. clubhouse with, indoor and outdoor pools, billiards, ballroom, a state-of-the-art fitness center, and yoga studio, and multiple tennis & pickleball courts. With a full-time lifestyle director already on site, there is always something for you to enjoy along with neighbors, friends and family. The community lifestyle is designed into a well-maintained calendar of activities such as outdoor yoga sessions, pickleball lessons, kayaking, paddleboard, mahjong tournaments, virtual book club and other socially distanced activities.  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, Four Seasons at Kent Island 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.
190 Sailcloth Way
Chester, Maryland
  • 4 Beds
  • 3 Baths
  • 2,862 SqFt
  • 0.120 Acres
HURRY to This OVER 2800 SQFT 3 Level BEAUTY!! She will not disappoint! Full of Updates and Upgrades to include Spacious Deck overlooking the Fenced in Backyard which surrounds the Inground Heated Saltwater Pool! Move right in and enjoy the POOL NOW!! Lots of FUN Memories to be had here! Boasting 5 Large Bedrooms (inclusive of MASSIVE BONUS ROOM), 2.5 Baths and walk in closets! WIDE OPEN EAT-IN KITCHEN has Cafe' Classic Dual Convection & Gas Oven for the Gourmet Chef at heart! Upgraded Kitchen has WINE Frig, Bosch Dishwasher, custom Tile backsplash, Granite countertops, Bar area, Desk area and a Sprawling Island overlooking the Family Room complete with Gas Fireplace and stunning Custom Surround Mantel!  Extra bonuses are a nice size Formal Dining Room, Separate Laundry Room with folding table and cabinets and an Oversized 2 Car garage with TONS of Storage space! Be graciously Welcomed Home every time with the extensive Covered porch... just bring those Rocking Chairs!  Superb location with walking distance to Shopping, Restaurants, Boat Landing, Grocery Store and more! Come see what Eastern Shore living is all about! Bike and Walking Trails, Beaches, Outlets, Marina's, Fishing and Crabbing Piers Playgrounds, Sports Fields, Parks, Seafood Restaurants and so much more! Easy commute to DC, Baltimore, Annapolis and Easton. Short trip to St. Michaels, Delaware Beaches and DE Shopping and Ocean City MD.  NO HOA!!
1620 Postal Road
Chester, Maryland
  • 5 Beds
  • 3 Baths
  • 2,818 SqFt
  • 0.320 Acres
Under construction and move in ready in 2022!
The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony.  The building has elevator access, 1 car garage and secure storage room per unit. Just a short walk or drive to the incredible 24,000 square foot owner's clubhouse opening summer 2022! 
Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, resort-style experience less than 25 miles from Annapolis and within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse, indoor and outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site, Four Seasons at Kent Island also features a well-maintained calendar of activities and classes from yoga sessions, to paddle boarding  or walking club. 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. Four Seasons at Kent Island 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. Call today to find out the details and start living the life you want. *Pictures represent a model home as this current home is under construction.
190 Harrier Way 31
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,600 SqFt
Under construction and move in ready in 2022!
The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony.  The building has elevator access, 1 car garage and secure storage room per unit. Just a short walk or drive to the incredible 24,000 square foot owner's clubhouse opening summer 2022! 
Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, resort-style experience less than 25 miles from Annapolis and within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse, indoor and outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site, Four Seasons at Kent Island also features a well-maintained calendar of activities and classes from yoga sessions, to paddle boarding  or walking club. 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. Four Seasons at Kent Island 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. Call today to find out the details and start living the life you want. *Pictures represent a model home as this current home is under construction.
190 Harrier Way 24
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,600 SqFt
Under construction and move in ready in 2022!
The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony.  The building has elevator access, 1 car garage and secure storage room per unit. Just a short walk or drive to the incredible 24,000 square foot owner's clubhouse opening summer 2022! 
Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, resort-style experience less than 25 miles from Annapolis and within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse, indoor and outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site, Four Seasons at Kent Island also features a well-maintained calendar of activities and classes from yoga sessions, to paddle boarding  or walking club. 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. Four Seasons at Kent Island 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. Call today to find out the details and start living the life you want. *Pictures represent a model home as this current home is under construction.
170 Harrier Way 34
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,600 SqFt
Welcome Home to 142 Winchester Street in the sought after neighborhood of Waters Edge in Gibson's Grant. This Coastal Cape Cod is the Ashford model featuring a first floor owners suite built by Koch Homes in 2020.

As you walk up to this home you will find a private covered full porch with ceiling fans, recessed lighting and views of the tranquil ponds, walking bridge and resident blue herons.

Step inside to find beautiful hardwood floors and plantation shutters throughout with ceiling fans in every room.  The main floor has a great room with a gas stone fireplace, solid double doors with transom open to a study, or guest bedroom. You will love entertaining in your gourmet kitchen with white shaker style cabinets with soft close doors and drawers, stainless steel appliances and a large kitchen island with gas cooktop and quartz countertops. The dining room opens onto a pavered patio with a backyard retreat.

Open the custom-installed barn door into the featured first floor owners suite with hardwood floors, a walk in closet with custom built in's, owners bath with double bowl granite countertops, a soaking tub and frameless shower with built in seat.

Craftsman features in this home include two-panel doors, crown molding and trim with oak stairs and handrails that lead up to the second floor featuring a sitting area with a custom wet bar, granite countertops, and pantry. A guest bathroom with upgraded shower features and furnishings. The two large bedrooms have their own roomy dormer that will accomodate a queen bed, and large room-width walk-in closets for storage and wardrobes.

Wait until you see the backyard oasis that has been custom landscaped. Two Ponds each with a waterfall in this private-fenced backyard that has two gates for front and rear access. And the finished, two-car attached garage is accessed by an expanded driveway.

This home has custom upgrades throughout and steps away from the nearby Chester River shoreline and ponds that will surround you with the atmosphere of the signature Gibsons Grant “Water’s Edge”.
The Community features include a private fishing and crabbing pier, community clubhouse with fitness center, a swimming pool, picnic pavilion, play area, and kayak storage and launch to accessible Macum's Creek.

You will love living in Gibson's Grant surrounded by acres of conservation areas, ponds, and home to the blue heron, osprey and deer.
Do not miss out on 142 Winchester Street you will love living the Coastal lifestyle.
142 Winchester Street
Chester, Maryland
  • 4 Beds
  • 3 Baths
  • 2,275 SqFt
  • 0.140 Acres
Under construction and move in ready in 2022!
The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony.  The building has elevator access, 1 car garage and secure storage room per unit. Just a short walk or drive to the incredible 24,000 square foot owner's clubhouse opening summer 2022! 
Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, resort-style experience less than 25 miles from Annapolis and within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse, indoor and outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site, Four Seasons at Kent Island also features a well-maintained calendar of activities and classes from yoga sessions, to paddle boarding  or walking club. 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. Four Seasons at Kent Island 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. Call today to find out the details and start living the life you want. *Pictures represent a model home as this current home is under construction.
170 Harrier Way 31
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,600 SqFt
Under construction and move in ready in 2022!
The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony.  The building has elevator access, 1 car garage and secure storage room per unit. Just a short walk or drive to the incredible 24,000 square foot owner's clubhouse opening summer 2022! 
Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, resort-style experience less than 25 miles from Annapolis and within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse, indoor and outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site, Four Seasons at Kent Island also features a well-maintained calendar of activities and classes from yoga sessions, to paddle boarding  or walking club. 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. Four Seasons at Kent Island 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. Call today to find out the details and start living the life you want. *Pictures represent a model home as this current home is under construction.
190 Harrier Way 21
Chester, Maryland
  • 3 Beds
  • 3 Baths
  • 2,600 SqFt
Gorgeous 2 story open foyer and family room. Owners suites on first and second floors. Kitchen boasts 42" maple cabinets with center island.  New carpet in Living , Dining and Family room. This home shows very well and will not last long in this market.
104 Woods Road
Chester, Maryland
  • 5 Beds
  • 4 Baths
  • 3,065 SqFt
  • 0.530 Acres

Maryland Waterfront ZIP Code List