Maryland Waterfront Homes for Sale 21620

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Featured Maryland Waterfront Homes for Sale 21620

Completely renovated 4 bedroom waterfront condominium located in the heart of historic Chestertown.  2 boat slips, adjacent to Wilmer Park and a few block from the main commerce area of the town including shopping and restaurants.  Condominium renovations include but not limited to new kitchen, new baths, hardwood floors throughout, new dock, recently replaced roof, new HVAC systems just to name a few.
215 Water Street 1
Chestertown, Maryland
  • 4 Beds
  • 4 Baths
  • 2,800 SqFt
Gliding Gander is a marvelous waterfront property overlooking the Chesapeake Bay offering endless unobstructed views across and up and down the Bay. This 9+ acre property features 675 +/- feet of substantially rip-rapped shoreline gently sloping to the water's edge, open land with approximately 2+ acres of tillable ground for horses, micro farming or gardening, and a large waterfowl pond serviced with a well. Included is a large, heated pole barn, perfect for a workshop and storage of equipment and country toys. The newly painted, one-level main house is perched on an elevated site near the water’s edge. Included is 3000 +/- sq. ft. of fully finished living space. Rooms include a spacious heated waterside sunroom, dining area, open kitchen, living room with fireplace, attractive library, master waterside bedroom, two guest bedrooms and a 2-car garage converted into a large party/gathering room. A spacious basement houses the mechanics for the home but also offers room for additional activities. The waterside deck, off of the master bedroom and living room is a perfect place to enjoy a cocktail and see the incredible sunsets. Rarely do properties like this one come available, especially with the location, privacy, and excellent waterfowl hunting. Situated centrally to both Historic Chestertown and Festive Rock Hall. Marinas nearby to keep your boat. A true Eastern Shore Property! Shared driveway please see documents. Please do not enter property without an appointment.
7280 Swan Creek
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 2,896 SqFt
  • 9 Acres
This circa 2011, white brick house was built to celebrate the expansive views over the  Chester River Yacht &Country Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The landscaping around the circular driveway is lovely; the garage is set on an angle as to be unobtrusive from the road and the house entrance. Inside, all the rooms enjoy the views; the glassed in sun room being the most spectacular. Beautiful flooring, oversize crown molding, chair rails, accent & recessed lighting and painted paneling throughout. New A/C handler, Rinnai system with boosters (to reach around this 4,000+ sq. ft. house), foam insulation underground and up the walls, crawl space encapsulated, 3 temperature zones and audio wired surround sound. The kitchen and owner's suite are too great to try to describe, for instance, the marble came directly from Italy and no longer available. Laundry and "mud kitchen" are between the owner's suite and garage. Take a golf cart to the club, ride a bike into town or just sit and watch the tall ships go by.
7755 Waterview Lane
Chestertown, Maryland
  • 4 Beds
  • 3 Baths
  • 4,730 SqFt
  • 0.610 Acres
Water, water everywhere! This incredibly unique property is situated on a sheltered deep-water creek offering a westerly, southwesterly exposure with uncompromised sunsets. Fairlee Creek offers one of the most convenient boating accesses on the upper Chesapeake Bay. This 1.9 acre property comes improved with 2 homes, a deep water dock with 5-6' depth, an outdoor barbeque patio overlooking the creek, and 575+/- feet of secure shoreline. One of the two homes on this spectacular property is conte-levered above the water offering the feeling of being on a yacht with panoramic views from every room. The second home is a three bedroom, comfortable, one floor rambler with lovely screen porch overlooking the creek. The location of this property is notable in that it is centrally located in unspoiled Kent County and convenient to both historic Chestertown and the bayfront town of Rock Hall. Great Oak Marina and Resort is a short stroll of golf cart ride away where the residents of Great Oak Estates may share in the use of the establishment's facilities including the pool, restaurant, beach, and 9-hole golf course. Great Oak Estates is a fun-filled neighborhood where the residents interact well together and the spirits are active in the summertime and peaceful in the wintertime!
22153 1St Point Road
Chestertown, Maryland
  • 3 Beds
  • 2 Baths
  • 3,153 SqFt
  • 1.910 Acres
You will be in Awe!  This property, improved with a spacious Contemporary "Deck House," is designed for the water enthusiast interested in little property maintenance.  Pictures speak a thousand words so let's get right to it:   Dual Zone HVAC (age - 5 years), Rhinnai Tankless Water Heater (age - 5 years), Roof (age - 13 +/- years), BAT septic system (age - 2016), Whole House Generator (20KW), Culligan Water Treatment System, .65 acres, 139' of protected shoreline, 100' pier with water, electric, @20,000 lb boat lift and 6.5' MLW, and more than enough storage for all the water toys.  Yes, ALL Meticulously Maintained! 12 nautical miles to the Chesapeake Bay, 9 driving miles to Downtown Chestertown.
There is No HOA, it's a voluntary Neighborhood Association.  Initiation fee is $45 and annual dues of $100 cover the cost of spraying for mosquitoes throughout the season and maintaining the community park with 3-slip pier (not deep water), insurance for the park, park taxes, & the park's ground maintenance) + the annual community picnic.
FIBER OPTIC HIGH SPEED INTERNET AVAILABLE THROUGH TALKIE FIBER.  Installation Flat Fee - $99.00.  3 tiers of speed.
Decking over sand mound system is permitted.
5712 Langford Bay Road
Chestertown, Maryland
  • 4 Beds
  • 2 Baths
  • 2,652 SqFt
  • 0.650 Acres
This historically designated home, situated on High Street with a refreshing gaze of the Chester River as you enter, receives many a pause by passers-by as they meander the brick sidewalks of downtown Chestertown. The 1790 residence was completely renovated and expanded in 2004 with an eye for both formal entertainment and comfortable living. The gracious foyer with front staircase and ample coat closet leads to a large parlor with original crown moldings and a fireplace.  The generously sized dining room has an adjacent wet bar, powder room and storage closet. A rear staircase leads to the primary suite on the second floor. An open floorplan emerges beyond with large island kitchen, a second dining space and sun-soaked living room with built-in cabinets and bookshelves. A wall of paned windows and French doors overlook a beautiful garden with brick pathways and mature plantings. While this beautiful property is recorded as a four-bedroom house, it currently features the entire middle to rear second floor as a primary suite with office, graciously accessed by a back staircase. The south-facing bedroom, with large walk-in closet, has a pair of French-doors leading to a nicely sized roof with wood railings and copper-topped pilasters waiting for a deck and perhaps pergola.  A marbled bath includes soaking tub, glass enclosed shower, pair of sinks and full-sized washer and dryer.  The office (or 4th bedroom) completes the primary suite. The front staircase leads to a nicely proportioned bedroom with fireplace and ensuite bath. Finally, another paneled door sparks curiosity until it is opened and a solidly built staircase with landing is revealed. An enchanting bedroom with two built-in beds, gabled roof, walk-in closet and ensuite bath awaits. This floor makes a perfect hideaway. The basement is 2/3 concrete slab and 1/3 wood planked lighted crawl space offering plenty of storage. A hobby/workshop room has a laundry sink. All mechanicals are easily accessed and well labeled.
117 High Street
Chestertown, Maryland
  • 3 Beds
  • 4 Baths
  • 3,226 SqFt
  • 0.090 Acres
Beautiful, elevated views of Fairlee Creek from this enjoyable home, situated out of the flood zone, in a quiet country setting. The private dock has deeper-water,  plus there is a very convenient public  boat ramp very close to the property.  From this protected location, you can boat out to the Chesapeake Bay in just minutes.  Gourmet kitchen with an over-sized quartz island and countertops, open to both the dining and living area, as well as the water views, perfect for entertaining. There are two bedroom suites on the first floor,  as well as a third bedroom and bonus room on the second. Hardwood floors throughout.  Brick-floored porch faces the water to enjoy the view.  A delightful screened porch on the other side of the house will become another favorite spot. Just minutes to downtown Rock Hall and Chestertown.  Under two hours from Philadelphia, South Jersey, DE or DC;.  Don't miss this comfortable waterfront property, perfect as a family retreat or retirement destination.
9831 Breezecroft Lane
Chestertown, Maryland
  • 3 Beds
  • 4 Baths
  • 2,352 SqFt
  • 1.360 Acres
This lovely Victorian, with peeks of the Chester River, has been updated and remodeled while keeping many of the original features. These include stunning parquet floors, hardwood floors, bulls eye moldings, wainscoting, built-ins and more. The front parlor has a gas fireplace and there are pocket doors between the generous size dinning room, parlor and the hallway. The gourmet kitchen has granite counter tops, stainless appliances and loads of storage. The family room has a wet bar, built in bookcases and a gas fireplace. The staircase to the second floor is simply beautiful. The master bedroom is huge and boasts a lovely master bathroom and walk in closet. The 2nd bedroom faces the water and is bright and sunny. The 3rd bedroom could be an office and has access to the 2nd floor balcony. The 3rd floor with its angles and great views has been used as an apartment. It has a kitchen, bathroom and separate outside entrance along with an inside entrance. The property is nicely landscaped and includes a back yard shed and raised beds for a garden. This is a real Water Street gem!
114 Water Street N
Chestertown, Maryland
  • 4 Beds
  • 4 Baths
  • 3,640 SqFt
  • 0.180 Acres
In c1750 this iconic property was known as Bedingfield Hands House and has enjoyed a storied life with many prominent Chestertown residents. Today, this well-maintained historic gem with enchanting curb appeal has hosted many an event for some of the most beloved non-profit organizations that give our town a very special sense of community. Before even entering the front door, visitors are welcomed by its' large, brick-pathed and picketed fence terraces and irrigated garden beds. One side path leads to a mudroom entrance, another side path guides you to a nicely sized private brick patio and screened porch. The foyer includes a full-size bath and hanging closet. To the right is an intimate library (possible 4th bedroom) with built-in bookshelves. To the left, the large living room with fireplace (currently gas) leads to a formal dining room with another fireplace and corner cabinet. Further on is a most inviting country island kitchen with hand-painted wood cabinets, stainless appliances (new in 2016), breakfast area and powder room. Access to the garage is through an ample mudroom/laundry room. The breakfast room door gives way to the rear patio and screened porch.  Upstairs hosts the primary bedroom with ensuite bath with unique ceramic floor tiles. Two additional bedrooms share an end-of-hall bath. The overhead attic with pull-down steps is insulated and suitable for storage. The crawlspace below was also recently insulated along with a complete caulking of its' wood siding as part of an energy efficiency initiative. Please notice that this Realtor waited until the very end of remarks to use the word "charming" ... but it is a must to state.
106 Queen Street S
Chestertown, Maryland
  • 3 Beds
  • 4 Baths
  • 2,296 SqFt
  • 0.140 Acres
Splish Splash! Just in time for summer of '22. Every day will be vacation with the 16x32 in-ground sparkling salt-water pool that comes with this 5 BR, 3.5 BA sprawling Craftsman set amidst flowering shrubs and colorful plantings in the sought after Orchard Hill neighborhood. You will love the large open gourmet kitchen with granite countertops - under cabinet lighting - heated tile flooring - cherry cabinets - 5 burner propane cooktop - wine chiller - double wall oven with warming drawer - large island w/prep sink & overhang for stools - sunroom facing the backyard overlooking the pool area w/heated tile flooring - large open living room with cathedral ceiling, hardwood floors and propane fireplace - sitting room or formal dining room with hardwood floors - office or music room with hardwood floors - Main Level Master En-Suite with a stunning white subway tile shower - soaking tub - shiplap walls - double vanity - walk-in closet -front porch for your rocking chairs and morning coffee - Zoned heat & air - on-demand hot water - beautiful paver sidewalks - 2 car attached garage - partially finished walkout basement with kitchen, full bathroom & living room - tons of storage space throughout the house & in basement - trex decking - 12x16 pool shed - heated pool - sunshade system - 14x14 pavilion w/epoxy flooring. A spectacular residence that demands your immediate attention!
8999 Orchard Drive
Chestertown, Maryland
  • 5 Beds
  • 4 Baths
  • 3,478 SqFt
  • 2.230 Acres
WOW!  THIS HOME  HAS SPACE FOR EVERYONE!  It features over 5000 sf of living space, with a  guest bedroom and  a bathroom on the first floor, and on the second floor is an extraordinary primary bedroom suite that has a walk in closet, sitting area, and an impressive bath. Plus, there are 4 more bedrooms  with 2 full baths.  The full walkout basement  has over 2000 sf of unfinished space.  There are tons of possibilities here, and all on  1.25 acres on a quiet cul de sac about 4 miles  outside of Chestertown, in Queen Anne's County.
106 Goose Roost Lane
Chestertown, Maryland
  • 6 Beds
  • 4 Baths
  • 5,366 SqFt
  • 1.250 Acres
This gorgeous pond is stocked, home to beautiful waterfowl, and nestled in rolling terrain in your private oasis you will be happy to call home.  This Cape Cod style home has a main level bedroom en-suite, with lots of closet space.   The living room has a gas fireplace and is open to the kitchen with plenty of cabinetry space.  Step out on the front porch to some farm field views.  There is a slider to a deck, but the deck needs work.    The location is awesome, and there are many possibilities!   You can fish, hunt, or photograph wildlife to your heart's content.  You are very close to a public landing on Fairlee Creek for the serious boaters.  Chestertown and Rock Hall are both a quick drive away! 

  The current owner is selling the property "as is" and is not interested in being involved in development plans.  Correct acreage is 18.969.  The road is an easement, owned by this property, and there are five homes that are responsible for the road maintenance.  Two more homes could be built, with county approval, and the public water/sewer hookup fees paid.  

Walk out basement is clean, dry and there is a pellet stove heating system compliments the existing HVAC system.  Plenty of room for a workshop.  Upstairs are two large bedrooms and a full bath. This is a beautiful country setting.
22911 Bay Shore Road
Chestertown, Maryland
  • 3 Beds
  • 2 Baths
  • 2,016 SqFt
  • 18.970 Acres
Don't miss this special location on Queen Street with 3 off street parking spaces and a rear bonus room that could easily be converted to a first floor master suite!  A major renovation in 2015 brought modern infrastructure underlying the historic details AND added living space including a new kitchen with a roomy screened-in side porch, and a vaulted bonus room with cork flooring which is perfectly situated to suit a variety of needs. This flexible space was built with a potential master suite in mind and is currently being used as a family room and formal dining area.  A full view of the fenced courtyard garden expands the feel of the bonus room while preserving privacy. It is conveniently adjacent to a full bath and laundry, making it nicely situated for conversion for one floor living, or for use as a family room, game room, beautiful office, studio, huge formal dining room, or anything else to suit your situation. This house is built to adapt and flex with your needs!  The eat-in kitchen is truly in the heart of this home. Enjoy cozy cork flooring and a matching suite of stainless GE appliances. The kitchen has three doorways: One to the screened porch & the outdoors, one to the formal living room in front, and one to the laundry, bath, and bonus room to the rear. You may find that entering from the screened porch from your private parking is most convenient, while the front porch entry may be your choice after walking around town. The front porch is the place to socialize with neighbors and to enjoy the beautiful street-side gardens for which historic Queen Street is known.  From the front door, invite your guests into the formal entry hall featuring a coat closet, and stairs to the second floor which leads the eye to a peek of the upstairs hall overlook. The living room is to the left in the front of the home with a gas fireplace and a handy office nook tucked under the stair. The second floor leads to two private bedroom suites both with ensuite full baths! The third floor does double duty in its current use as an artist's studio with a sink on the left and also the third bedroom with a twin bed to the right of the stairs.  Right in the beating heart of historic Chestertown, this home is within a  block of fine dining, an artisan bread bakery/coffee shop, a clay studio, art galleries, the Garfield Center for performing arts, the County Court house and just about two to three blocks to an ice cream store and Luncheonette, the Saturday Farmer's Market at Fountain Park, the Chester River front, the new playground at Wilmer Park, the rail- trail, post office, Cross Street shopping, Natural Food Store, and more! Home to Washington College and  many festivals, Chestertown also has a brand new YMCA and is within one and a half to two hours of Baltimore, Washington, and Philadelphia airports!
116 Queen Street N
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 2,110 SqFt
  • 0.140 Acres
Spacious rancher on nearly 5 acres. 3 bedrooms and 3 full baths.  2 of the bedrooms have en suite baths. Open floor plan with great kitchen. Vaulted ceilings in the living room.   Large laundry room off the kitchen with washer, dryer, utility sink and pantry. Den with vaulted ceilings could be used as a 4th bedroom or craft room.  Partially finished basement with another room that could also be used as an additional bedroom or hobby room. Large unfinished area in basement with plenty of room for storage and has an additional washer and dryer.  Screened in porch off the kitchen and owner's suite. Small green house for the aspiring gardener. Lovely view of the surrounding farmland.  Peaceful country living but less than 10 minutes to Chestertown.  Interior pictures coming soon!
24354 Langford Road
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 2,266 SqFt
  • 4.980 Acres
Wonderful Chester River get-a-way with extensive accessible river frontage. Private setting with approximately 3-4 acres of solid ground with 12-14 acres of marshland which offers excellent waterfowl hunting! Included is a 2 bedroom, 1 1/2 bath elevated, (over a 3-car garage) ranch style home.  Views of unspoiled farmland across the river. These types of properties are hard to find and rarely come on the market! Deep Landing public boat ramp located is just down the road. Located in Queen Anne County just minutes to downtown Chestertown and easy access to Rt 301. Waterfowl shoreline permit in documents.
115 Pintail Road
Chestertown, Maryland
  • 2 Beds
  • 2 Baths
  • 1,144 SqFt
  • 18.100 Acres
Look no further, 1,820 square foot home on the most desired, Queen Street, to your dream, Rose Cottage.  Rock on the front porch or eat in the enclosed back porch with large picture windows looking out onto the brick patio into the pond, and through the attached arbor to the secret garden, all fenced in.  This place is a RARE FIND!  Inside, a welcoming fireplace in the living room, built-in hutches/cupboards, shelves over the doorways, crystal chandelier from Vienna, professional library off the dining room, large country kitchen, propane range, huge closets throughout, plus a large cedar closet - so much space, lots of lights.  The third bedroom boasts exposed beams, with cottage windows with view into the trees, exposed chimney brick in 2 of the rooms.  Romantic, come and see...  See documents for R-3 Zoning Permitted Uses on Accessory Dwelling Units.
117 Queen Street N
Chestertown, Maryland
  • 3 Beds
  • 2 Baths
  • 1,820 SqFt
  • 0.110 Acres
Why wait for new construction? This Home is MOVE IN READY!  Rare find on the Queen Anne's County side of Chestertown! Only 50 Minutes to the Annapolis Mall, 30 Minutes to Middletown DE!
  You 'll be delighted with this beautiful spacious light filled home!  Located on a quiet Cul-de-sac with  over 3,400 square feet of finished living space. Tax records do not reflect the correct finished square feet of space!!  Open concept Living features soaring vaulted ceilings and a gorgeous stacked stone fireplace in the Living room. Fireplace has been outfitted with a wood burning stove insert for efficiency and added heat for the house. Hardwood floors bring warmth and beauty to the main level. Kitchen is spacious and outfitted with newer stainless steel appliances , all appliances are less than four years old and stove is brand new! Granite counters, under cabinet lighting and decorative tile backsplash. There is a separate Wine bar with Granite counter, seating and storage! The laundry is just off the Kitchen and provides additional pantry storage, cabinets and wine racks! An eat in breakfast area holds a table large enough for six! This is an entertaining dream!  Open floor plan flows into the Living room and through to the Den. (Which can also be a Formal dining area... Make it suit your needs!) The Large cabinet bookcase is included in the sale! This fabulous home features a Main Level Primary Bedroom suite!  Primary bedroom is filled with light and has door out to the rear deck and hot tub for your enjoyment! Spacious primary bath has separate tub and shower stall, double vanities and tons of counter space! Large walk in closet holds all your clothes with ease! Upstairs find 3 large bedrooms with spacious closets and ceiling fans. A Jack and Jill 4 piece bath with separate sinks and shower rooms! Also an Upper level bonus room /office with vaulted ceilings, fan and attached 3 piece bathroom!  All new carpet on the entire upper level and Fresh paint in most rooms!  Dramatic catwalk balcony overlooks the main living area! Did I mention the basement? Also a rare find, there is an additional 1300 square feet of room down below! Walls in basement are sealed  with UGL dry lock paint,  A large workshop with workbench, Shelving,  storage and cabinets will be included and has stairs and bulkhead doors to the backyard!  a few extra bits... House has been wired for "Smart Home " use! Rough in plumbing exists in the basement for a bathroom! Washer and dryer only 4 years young! Home has on demand tankless hot water system! Central Vacuum system!  Brand new Water Softener system! Brand new main level HVAC!  Outdoors you will find a spectacular summer paradise featuring a large above ground pool (with new in 2021 updated filter system), spacious deck and Hot tub!   The .46 Acres has a fully fenced backyard and mature landscaping across the front yard.  Plenty of pictures here for you to enjoy and see how this spacious home can fulfill all your needs!  A home warranty will be provided to the buyers of this well loved home to ensure it's next owners are well cared for! No HOA, covenants or restrictions! 

Chestertown is just a short drive across the Chester River Bridge and you will find an exciting array of restaurants, shops and entertainment. The Garfield Center for the Arts and Washington College are also located here and make for diverse cultural and educational opportunities. There is a local Farmers Market every Saturday morning right downtown where you can purchase local vendors wares and enjoy the camaraderie of friends and neighbors. Many annual events fill the calendar and bring tourism and an economic boost to the area. The Chester River is a focus of the life and history of the town. 
Queen Anne's County Schools are top Rated! Call for your showing today!
108 Garland Avenue
Chestertown, Maryland
  • 4 Beds
  • 4 Baths
  • 3,407 SqFt
  • 0.460 Acres
Don't want the hassle of going up & down stairs but still want house space? This is not your ordinary rancher - it's oversized 30ft wide with over 2700sqft of living space and there's no other like it in the sought after Coventry Farms. This home is one of the larger lots from the original building development sitting on just over a half acre. Hardwood floors & 9ft ceilings. New roof in 2019. Energy efficient 22-seer dual-stage hybrid-heat pump HVAC system. Never run out of hot water with the Navian tankless hot water heater. Always wash with clean water from the whole-house water filtration system. Always drink clean water from the reverse osmosis system at the kitchen sink. Oversized 2 car garage, 25x30 with 12 ft ceilings that can fit a car lift. Lofts for extra storage space. Attic can be used as storage OR can be finished to add another 1,000+ of living space. Living space includes a Great Room with lots of natural light. Kitchen includes stainless steel appliances. Master bedroom with large walk-in closet. Sunroom & back deck lead out to a wide open backyard. Low maintenance landscaping. No HOA. Only minutes to downtown Chestertown, restaurants, shopping and marinas.

Room Measurements
Garage 
25'x30' ceiling 11'
Kitchen
17'x 15'
Dining room
13'x15'
Living room
17'x 19'
Front sitting room
13'x15'
Master bedroom
17'x15'
Bedroom 2
13'x11'
Bedroom 3
13'x11'
Sunroom
16'x17'
311 Mayfair Drive
Chestertown, Maryland
  • 3 Beds
  • 2 Baths
  • 2,700 SqFt
  • 0.580 Acres

Maryland Waterfront ZIP Code List