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
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
10 acre private home with pool on the Chesapeake Bay and western sunsets! 3 bedroom 4 bath home with private sauna, heated pool with electric pool cover, home generator, wood burning fireplace and separate wood stove. Just finished painting inside and out. All hardwood floors have been refinished too. This home is move in ready and a great value for under 1 million!
Don't let this waterfront home with big water views get away!
9556 Chantilly Farm Lane
Chestertown, Maryland
  • 3 Beds
  • 4 Baths
  • 2,276 SqFt
  • 10.160 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
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
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
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
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
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
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
Here's a sweet spot on historic Queen Street... not only a great location within a block or two of everything Chestertown, but also a sweet spot to call home with front and rear porches, a garden patio, and cozy sun-filled living spaces that say "stay awhile!"   After a major rehab in 2006, this beauty has since been gently used on a part time basis and well maintained by a caring owner. Agents, please read additional agent info.   It's entirely move-in ready!The owner has completed a pre-sale home inspection to share with potential buyers. From the front porch, enter onto original wood floors into the living room with a gas fireplace featuring a uniquely beautiful salvaged mantle that provides a focal point for the conversation area. The entire home is light and bright from numerous windows and wide side alleys that allow the sun in from all angles. The dining room features the original fireplace (non-working) which adds architectural interest and makes a great dry bar when entertaining. The kitchen in the rear of the home has a half bath next to the rear door, a laundry room with a window, a coat closet, a cooking island/breakfast bar, and room for a table. The ceiling over the table space is pre-wired for a pendant lamp or chandelier. Enjoy stainless appliances, granite countertops, ceramic tile flooring, a double sink with a window, and a dual fuel Jenn Air range with a downdraft exhaust fan, a gas cooktop and an electric oven: preferred for even baking! Upstairs, you'll find three bedrooms and two full baths. The front bath has a stall shower. The rear bath has a massive cast iron claw-foot soaking tub to stretch out in and features optional extra heat from a ceiling fixture to make it luxuriantly toasty while soaking in the tub! Both full baths are generously sized with a window and ceramic tile.  The hall to the front bedroom has a door to enclose the nearest bath and make it en-suite-or-not, giving you flexibility to adapt for guests or family as you like. The rear bedroom has a vaulted ceiling, a window seat, a view of the garden, and is adjacent to the hall bath with the clawfoot tub.  The third bedroom, currently used as a music room,  has a window and a cute bookcase style closet. It would make a nice office, a generous walk-in closet, or hold a single bed. The third floor is unfinished attic space providing generous storage which is easily accessible via a staircase behind a door in the front bedroom. The attic is floored and has old plaster walls, two windows and has access through a wall panel to an additional lighted attic area that houses the AC ductwork. This home has street parking and the added convenience of a shared off-street parking space to the left of the front porch in the deed! Walk to the Saturday Farmer's Market, restaurants, shops, the Chester River waterfront, marina, natural foods, neighborhood groceries & convenience stores, bread shops, coffee shops, pizza, ice cream, numerous parks including a brand new playground at Wilmer Park, and even some professional services, all easily walkable from this fabulous historic district location, N  Queen Street!
123 Queen Street N
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 1,659 SqFt
  • 0.070 Acres
Beautiful and quiet setting. Lots of grass, fields, privacy and all the natural life Eastern Shore has to offer. Don't miss this opportunity to own this unique 4 bedroom, 2 bathroom home with over 2,600 sqft. of living space that sits on 4.5 acres of land. The home features a central vacuum system, a whole house generator, attached 3 car garage with hydraulic auto lift and oil pit. Paved driveway with plenty of space for parking. This property has endless opportunities! Minutes from downtown Chestertown. Close to local waterfront dining, entertaining, parks and schools.
300 Gatling Drive
Chestertown, Maryland
  • 4 Beds
  • 2 Baths
  • 2,619 SqFt
  • 4.540 Acres
Handsome custom built  3 Bedroom /2.5 bath Brick Rancher on 1.3 beautifully landscaped acres in the highly desirable water oriented community of Great Oak Estates offers the ultimate combination of  gracious in-home  living plus low cost access to a full suite of  fabulous community amenities including a 9 hole golf course, community pool, restaurant, Bay front beach  and marina and boat launch facility.  This immaculately maintained  home offers the convenience of all on one floor living and features a spacious primary bedroom with attached full bathroom  with walk-in shower;   an attractive updated eat-in kitchen that opens to a large private screened in porch overlooking the backyard;  a high tech induction cooktop, ample closet space including four walk-in closets; Hickory flooring in the foyer and living and formal dining rooms and hallways; an outdoor deck with hot-tub; an oversized garage;  fiber optic internet service; a satellite powered security system;  central A/C and more.   Come see for yourself today.  This  rare opportunity to own a great home in a unique  waterfront community  in easy driving distance to Chestertown won't last long!
10165 John Carvill Road
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 2,774 SqFt
  • 1.330 Acres
Look no further - Single level living on beautiful corner lot in sought-after Orchard Hill.  Well maintained, 3 bedroom, 2.5 bath custom home. Have your coffee in the sunroom or large kitchen with island and spent hours creating in your large workshop with outside entry.  The over-sized 2 car garage will check all the boxes for the car enthusiast or active owner for their toys.  The unfinished space over the garage can be easily turned into a FROG - family room over the garage used for entertaining and fun for all. Come see for yourself. Professional photos are coming Monday.
8616 Orchard Drive
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 2,422 SqFt
  • 1.660 Acres

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