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
A $100,000 decorator allowance offered toward updating and redecorating. Never before on the market, Windswept is a remarkable property with views that celebrate the water.  Built by the owners. Private dock with 5 deep water slips. 5-6ft MLW (buyer to verify). Large deck with gazebo to enjoy the  boats going by.  Geothermal heat and AC.  2 stone wood burning fireplaces.  A breathtaking view from almost every room of the house!  Lots of space in this sprawling home. Primary bedroom has a large sitting room attached with 2 walk in closets. An additional bedroom also on the main floor.  The second floor has a nice family room which is open to the living room below with its own tanning deck.   2 bedrooms with a Jack and Jill bath also on the second floor.  An additional small room could be used as an office or just additional storage. Some updating needed but in overall wonderful condition. Nice landscaping. No flood insurance needed.  High speed internet available. Voluntary civic association is $100 per year. $350 per year for road maintenance.  An easy stroll to Great Oak Marina and golf course.
10108 3Rd Point Road
Chestertown, Maryland
  • 4 Beds
  • 4 Baths
  • 4,285 SqFt
  • 1.480 Acres
This fabulous craftsman style 3 bedroom home, is perfectly situated to enjoy the beauty and tranquility of the East  fork of Langford Creek/Bay with approximately 150' of shoreline and sandy beach.  Great room was added in 2001, with a loft and cat walk to offer added living area. 
 The subject property is one of 5 waterfront properties that belong in the Cacaway Farm Cooperative Housing Corporation, an exclusive farm housing community.  Experience the same benefits of a fee simple ownership but share the cost of expenses.  Enjoy privacy and the use of your own waterfront with sandy beach by way of a gentle slope to the water, launching kayaks or canoes while deep water slip at the community dock is also included.  A south facing direction on the water side offers wonderful & welcoming breezes throughout the summer.  It is improved by 2  car heated garage built in 2006  plus a smaller area for storage with a  bonus area above.  The area above has radiant floor heat.
New BAT septic was installed in last two years, with the county  becoming  the operator  of the new sewage treatment area. 
 Please do not drive down Cacaway Farm Lane without an appointment.  This is a private lane.
23393 Cacaway Farm Lane
Chestertown, Maryland
  • 3 Beds
  • 4 Baths
  • 4,446 SqFt
An Eastern Shore Haven: twenty picturesque acres, 10+/- wooded, with exceptional hunting in a trophy whitetail deer corridor and where wild turkey roam and roost. A gorgeous and classic 1999 custom built home, modeled after a Nantucket fishing Captain's cottage, with nine foot ceilings, solid wood doors, Kolbe&Kolbe windows, a comfortable screened porch, wood burning fireplaces, and a gourmet, open concept kitchen. Above the garage is the caretakers apartment with a private entrance, featuring one bedroom, full bathroom, and kitchenette. Fenced acreage, turn-out sheds, automatic waterers, a three stall barn with connected paddocks, and all the necessary amenities. The idyllic pond and gazebo offer the perfect spot to picnic and relax. The gunite "sport" pool is accompanied by a shaded pergola and a storage shed.
22770 Fairgale Farm Lane
Chestertown, Maryland
  • 4 Beds
  • 3 Baths
  • 2,535 SqFt
  • 20.080 Acres
Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other.  Walk to downtown shops and restaurants, just a few blocks away.
230 Water Street S 1
Chestertown, Maryland
  • 3 Beds
  • 4 Baths
  • 2,490 SqFt
  • 0.090 Acres
Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other.  A short walk to downtown shops and restaurants.
226 Water Street S
Chestertown, Maryland
  • 3 Beds
  • 4 Baths
  • 0.090 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
Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other.  Walk to downtown shops and restaurants, just a few blocks away.
228 Water Street S
Chestertown, Maryland
  • 3 Beds
  • 4 Baths
  • 0.060 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 spacious, well maintained home sitting on a very private road offers 5 bedrooms, gourmet kitchen, sunken living room,  2 stone fireplaces, hardwood flooring, radiant heat, 3 car detached garage/workshop, complete with its own man cave! 
Downstairs there is plenty of room for entertaining, inside and out. Open plan kitchen with doors out onto a covered stone porch which wraps around to the front. On the other side is a large open lawn with mature trees overlooked from the large Living room addition featuring floor to ceiling windows, stone fireplace and 9'+ ceilings. Please no drive-by’s. Located on private road with no turn around.
10258 Mill Hollow Lane
Chestertown, Maryland
  • 5 Beds
  • 3 Baths
  • 3,414 SqFt
  • 5 Acres
GORGEOUS VIEWS OF THE CHESAPEAKE BAY!!  The views from all the living areas and the first floor primary bedroom are stunning.    Year round sunroom and connecting decks with those great views make this a home for all seasons.  Come and see this REMARKABLE MAKEOVER of this spacious home.  You won't want to leave.
9050 Point Lane
Chestertown, Maryland
  • 4 Beds
  • 3 Baths
  • 2,439 SqFt
  • 0.920 Acres
Beautiful home boasting nearly 4000sqft In a great neighborhood located in Queen Anne's Co but conveniently located less then 3 miles from Chestertown for shopping and those quick runs to the store. Highly desired school district area as well. Out back you will find your beautiful Oasis to relax and enjoy your time poolside. This home also offers a Huge walk out basement at 1928Sqft with bathroom rough ins for more flex space. Large open kitchen area with a center island leading in to your living room area. 

More Info and Pictures coming Soon!
121 Bass Track Court
Chestertown, Maryland
  • 4 Beds
  • 4 Baths
  • 3,904 SqFt
  • 1.270 Acres
Beautiful home in Orchard Hill set on 2 acres, featuring 3 bedrooms, 2.5 baths. Large office could easily become a 4th bedroom.   Gleaming hardwood floors.  Many more details and pictures coming soon!
8930 Orchard Drive
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 3,147 SqFt
  • 2 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
Need Space??? Well here it is! Bring Your family and bring you Boat, RV, Collector Cars...Golf Cart...etc.... Home features 4 Bedrooms 2.5 bath. 2 Car Attached Garage PLUS a Detached Pole Building  30x48 with 12' Doors! Inside the home is plenty of room also. Eat-in kitchen with Breakfast bar and lots of Cabinets! Separate Dining Room, Living Room and Large Family Room. Upstairs you will find a Spacious Primary Bedroom with Full bath and Walk-in Closet.  3 extra generous size rooms and another Full Bath. Nice level lot with extensive landscaping. Within Minutes to the Chester River and Historial Chestertown and Centreville. Eastern Shore Living at its Best!
329 Union Church Road
Chestertown, Maryland
  • 4 Beds
  • 3 Baths
  • 2,464 SqFt
  • 1.030 Acres
The moment you drive down Leeds Court you will be mesmerized by the beautiful mature oaks that line the street!  There has only been one owner of this amazing property and it is located in the section of Coventry Farms that does not require a HOA membership or deferred water and sewer charges!  Current owners purchased brand new in 2004.  Since then they have added many upgrades.  A 30'x30'  2 car detached garage/workshop with 12.5'+/- ceiling, equipped with 2 car lifts for the do it yourself mechanic, heated and cooled with large storage area over garage and an in-ground pool were added.  Two large sheds were added and the entire rear yard is privacy fenced.  A large patio area around the pool is perfect for outdoor entertaining during the warm weather months.  There is a hookup for a portable generator and the portable generator is also included!  The interior has almost completely been freshly painted with new carpet installed on stairs and in the basement.  The kitchen, family room and Florida/sun room provide a large area for indoor entertaining.   The owners suite is huge with cathedral ceiling and a private sitting room with walk-in closet and a spacious bath with vaulted ceiling, Jacuzzi tub and separate shower and tiled floors.  The basement offers a very large bedroom with its own bath and an exercise room and another room that could act as a home office.  Arguably the best location in Coventry Farms!!
206 Leeds Court
Chestertown, Maryland
  • 4 Beds
  • 4 Baths
  • 2,693 SqFt
  • 0.510 Acres
Eastern Shore Victorian home set in Chestertown’s Historic District has been thoughtfully updated and is well cared for.  This lovely traditional home spans three levels and greets owners with an elegant entry hall that opens to the living room with fireplace. Just off the kitchen is the family room offering additional living space. Bright with natural light, the kitchen invites entertaining with a spacious dining area opening to a large deck and landscaped fenced-in yard. 

Conveniently located on a corner lot, the home offers lovely views of the Washington College campus and is just a walk away from the hospital, library, walking trail, the Chester River waterfront and downtown historic area. Another sought-after amenity includes a separate 2-car garage. The home offers 4 bedrooms and 3 full baths, as well as a separate 3rd floor living area, perfect for guests and family. 

Founded in 1706, Chestertown is set on the banks of the Chester River. Brick sidewalks are lined with period homes, shops, a theatre, cafes, galleries, an oyster bar and restaurants. Activities and places to explore include the River Walk, weekly farmers market, Fountain Park, annual festivals and river cruises on the Chester River Packet. Visitors and residents alike are attracted to the area’s natural beauty and its quiet, small town lifestyle combined with the convenience of being about 90-minutes from Washington, D.C. and Philadelphia and about 1-hour from Wilmington.
225 Washington Avenue
Chestertown, Maryland
  • 5 Beds
  • 3 Baths
  • 2,536 SqFt
  • 0.220 Acres

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