Maryland Waterfront Homes for Sale 21620

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Featured Maryland Waterfront Homes for Sale 21620

Welcome to Fairgale, a tasteful waterfront community located minutes from Historic Chestertown and Rock Hall. This 36.66 total acre property with 1250+/- feet of stable shoreline and 21+/- fertile tillable acres is ideally elevated and positioned to take advantage of the panoramic water views and sunsets across Fairlee Creek.
        The thoughtfully designed residence has the perfect balance to host both casual or formal gatherings, either indoors or outdoors. The exterior of the residence includes a wonderful slate patio, brick sidewalks, beautiful gunite swimming pool, storage building for small watercraft and lawn equipment, and a winding asphalt driveway. The interior includes a chefs eat-in kitchen with cozy gathering area, a formal living room with double patio doors, a formal dining room, an office, and a private first floor primary bedroom suite with two spacious walk-in closets and a large walk-in shower. Upstairs, you will find three additional bedrooms with two spacious full ceramic tiled baths. The finished basement is a grandchild's dream with a marvelous game room area, built-in bunk beds, separate bedroom, full bath and separate outside entrance.
       Other notable interior features include beautiful wood floors (Oak and Heart Pine), designer tile in bathrooms and laundry room, a gourmet kitchen featuring professional grade appliances, expansive butcher block center island, granite counters, and exposed ceiling beams. A large sliding glass door opens onto the lovely, screened porch overlooking the pool and patio. This home is loaded with numerous other tasteful finishes and features for which you must see to appreciate. High speed fiber optic internet at the property!
        Water access is available from the gently sloping lawn to the water's edge or also a short golf cart ride away from the community waterfront area where you will find the property's own deep water boat slip with new 5-ton electric boat lift and community boat ramp.
        This property offers the epitome of true Eastern Shore living, with timeless style and endless possibilities!
22600 Fairgale Farm Lane
Chestertown, Maryland
  • 5 Beds
  • 5 Baths
  • 4,033 SqFt
  • 36.660 Acres
Completely renovated 4 bedroom waterfront condominium located in the heart of historic Chestertown adjacent to Wilmer Park.  Completely new community dock with two deeded boat slips and new boat lifts. Easily walkable to 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 .  The perfect blend of waterfront/in town living.
215 Water Street 1
Chestertown, Maryland
  • 4 Beds
  • 4 Baths
  • 2,800 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
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
This listing offers the unique opportunity to own two waterfront parcels, one improved by a beautiful 3-4 bedroom cape, and an adjacent perc approved lot all located less than a mile from Chestertown.  The addresses are 121 Lyons Ln.  which is 1.9 acres, 118 Lyons Ln. which is 1.2 acres and 117 Lyons Ln. which is .44 for a total of 3.5 acres. They are being sold together and the tax information is for all three lots. The cape is on the 1.9 acre wooded lot and features premium materials and finishes. There are yellow pine floors reclaimed from Camden Yards, crown moulding, wainscoting, panel doors, fireplace, sun room and a master bedroom on the first floor. The second floor has two bedroom and a third room which could be a bedroom, office or 2nd floor family room.  The second floor bathroom is huge and has just been remodeled. There is also a separate studio or home office, also recently remodeled, in the rear yard with AC/Heat. A Williamsburg inspired garden surrounds the studio and the rear yard is partially fenced.  The waterfront is a quiet creek right across the Chester River from the historic district. The owners have a permit for a new dock and it will convey. By the water is a large screened in Gazebo perfect for crab feasts or for enjoying the abundant wildlife. The second waterfront lot is 1.2 acres, not buildable, but it does allow for more water access. The third lot is .44 acres, perc approved, level, cleared but with some mature trees .  A second home could be built for a family compound or a carriage house, guest house or barn. Or,  simply hold on to it as an investment. Lots of options so come take a look!
121 Lyons Lane
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 2,327 SqFt
  • 1.900 Acres
This custom home is one of a kind and perfect for the golf enthusiast! Here you can walk out your back door to holes 14, 15, and 17 of the Chester River Yacht and County Club golf course. This home was built by Darling Construction eight years ago and is in immaculate condition. In this home you'll enjoy cooking and entertaining in the large, upgraded kitchen with a wet bar, granite countertops, soft close cabinets, pot filler over the stove, and stainless-steel appliances. Enjoy your days in the sunroom... full of windows and light and your evenings in the living room by the gas floor to ceiling stone fireplace. This home has a formal dining room with French glass doors, separate office, two guest bedrooms with a Jack and Jill bath and large primary suite. The primary bedroom has two walk-in closets, laundry area, and connected to the primary bath with heated floors, dual sinks, and a walk-in shower with dual showerheads.  Park your car in the oversized, side entry three car garage that leads into the house with a guest bath and pantry. A spectacular feature of this home is that it is completely handicap accessible. Wide halls, large doorways, zero steps, roll in shower and handrails. This property has all the upgraded features including, a geothermal system, crown molding and chair railing, recessed lighting, tray ceilings, 9'+ ceilings, tankless hot water heater, full concrete crawlspace, lawn sprinkler system, and so much more! Be sure to schedule your showing right away because this home is hard to find!
25731 Collins Avenue
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 2,751 SqFt
  • 1.010 Acres
Celebrating the water on Langford Creek! This rare offering is conveniently situated in a highly sought-after location within a short country drive to Historic Downtown Chestertown or a several minute ride to Rock Hall. The property offers breathtaking southwestern unobstructed views of Langford Bay and the Chester River. The property comes complete with a multi slip, deep water dock (6+ feet depth) with one slip covered and two slips with lifts. The cozy cottage has 3 full bedrooms and a sleeping loft along with two full baths. Notable features include a first-floor primary suite with sliding doors leading to water's edge, a waterside shaded screened porch, living room with wood-burning fireplace, separate dining room, upgraded eat-in kitchen, and separate laundry room. The home is situated with gorgeous views, across the rarely utilized adjoining community open space, of Horner Cove. Also included is a shaded waterside elevated patio, an emergency generator, a partial basement, a state-of-the-art Advantax Septic Treatment System and waterside bulkheading. $50.00 HOA initiation fee, $100.00 yearly HOA fee.
5598 Langford Bay Road
Chestertown, Maryland
  • 3 Beds
  • 2 Baths
  • 1,736 SqFt
  • 0.230 Acres
Eastern Shore home, c.1890 is located in the heart of Chestertown’s historic district and is just a short stroll from the Chester River Walk, Fountain Park, shops, dining and walking trails. Every modern-day amenity has been incorporated into this lovingly renovated home while preserving the original charm. Skylights and windows let in an abundance of natural light to showcase the lovely heart pine floors and detailed millwork. 
The home spans three levels and greets owners through a gracious foyer opening to the library with its reading nook bookcase and fireplace. The first floor open design also features a well-appointed kitchen, breakfast room, dining room, living room and two powder rooms. The second floor is designed with two ensuite bedrooms and the top floor offers three bedrooms and a powder room. Adding to the welcoming ambiance of the property is the recently built carriage house used as a workshop/studio and an english gatehouse serving as a potter’s shed. The enchanting garden features a goldfish pond, stone walls, planting beds, and a pergola with climbing rose vines. 
Founded in 1706, Chestertown is set on the banks of the Chester River and is home to Washington College. Brick sidewalks are lined with lovely period homes, shops, a bakery, galleries, theatre, oyster bar and restaurants. Residents and visitors alike enjoy the river walk, parks, farmers market, walking trails, community activities and annual festivals. River cruises are available on the Chester River Packet and Schooner Sultana. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia and 1-hour from Wilmington.
111 Mill Street S
Chestertown, Maryland
  • 5 Beds
  • 5 Baths
  • 2,776 SqFt
  • 0.130 Acres
You will appreciate peaceful living in this waterfront community on the Chester River just  minutes from historic Chestertown.. A light-filled and spacious open floor plan is wonderful for enjoying the elegant interior amenities. You will also want to sun bathe or swim at the lovely pool, stroll the shell walking paths throughout the community and along the shoreline, go kayaking from the community dock, or just sit back and relax while enjoying the  Eastern Shore lifestyle.
209 Landing Lane
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 2,400 SqFt
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
Newly listed! This lovely 3 or 4 bedroom, remodeled  home in Country Club Estates with a glimpse of the Chester River sits on an acre of prime land overlooking the 15th fairway of the Chester River Golf & Yacht/Country Club. There is no HOA. Approximately 3000 square feet of living space and an additional very large basement offers the possibility to expand.  Family room has terrific built-ins and wood burning fireplace. Primary bedroom has large sitting area, walk-in closet and en suite bath with separate soaking tub. Inviting and spacious, light-filled rooms throughout bring the outdoors in.  Outdoor spaces to enjoy and entertain include covered front patio, rear deck with spa, and small pool with deck for cooling off. Plenty of storage with two attics and oversized two car garage. Energy efficient home and whole-house generator. Underground dog fence and propane tank included. Just a few minutes from large waterfront park and pavilion, boat ramp and launch area, as well as entertainment and fine restaurants in downtown historic Chestertown. Schedule a showing today.
25819 Collins Avenue
Chestertown, Maryland
  • 4 Beds
  • 3 Baths
  • 2,952 SqFt
  • 1.010 Acres
A unique opportunity!  This charming brick building was originally built in the 1800s as a chapel named Mowbray Chapel, eventually abandoned and then the interior was completely rebuilt in 2021 with electric, utilities, a new well and septic.  A SIMPLY STUNNING light filled space that has been used as a residence and entertaining venue.  Completed with the highest quality of materials and a brand new kitchen, full bath room and laundry room  as well as a gas wood stove yet blended with the large windows, gorgeous brick walls, high ceilings and substantial woodwork.  A true blend of old world elegance and modern amenities.    Nestled among the mature trees on a 3+ acre property, there is also good outdoor space with a lawn, woods and a pond combined to offer spectacular outdoor areas year round.
5179 Quaker Neck Road
Chestertown, Maryland
  • 1 Baths
  • 1,148 SqFt
  • 3.220 Acres
Gleaming hardwood floors throughout this light filled home makes mornings a peaceful pleasure.  The family room is especially comfortable with a gas fireplace to cozy up to and open to the dining area.  Enchanting light spills in from windows overlooking a brick floored screened porch and a fenced in yard for your four-legged friends.    The kitchen offers every convenience with upgraded counter tops, plenty of cabinet space, a breakfast area, and also overlooks the dining area.   There is a laundry room with a double sink, and plenty of storage with built in cabinets and countertops.  The two- car garage is immaculate and perfect for that handy person in your home! 

Amenities continue into the bedroom areas with separate closets in the main bedroom and a large walk-in shower in the nicely appointed private bath.  The other two bedrooms have tons of room and storage as well.    Some of the closets throughout the home are cedar lined closets.  

The yard has some beautiful established beds, a fenced back yard and there is a small greenhouse for the serious gardener to get started on spring seedlings!  Just a ton to love about this home!   The current owner has maintained the home meticulously and replaced the furnace approximately 7 years ago and the well pump 5 years ago.  There is scheduled yearly maintenance done on the HVAC systems. 

Heather Heights is a welcoming neighborhood for biking, walking, running, or rollerblading.  So much to love in this home, which is a quick drive from Chestertown and near the Chester River Yacht and Country Club.
7898 Radcliffe Road
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 2,264 SqFt
  • 0.950 Acres
Rare waterfront residence/"pied-e-terre"  in historic downtown Chestertown situated within in an iconic late 1800s Georgian brick beauty. Built as one of the towns' first prominent apartment buildings, it was restored and converted to a six-unit condominium in the early 2000s. This second-floor gem is like a multi-carat diamond with wonderful clarity and cut.  Featuring two bedrooms and two hallway baths, the Water Street side (front) living room provides a newly upgraded gas fireplace and is perfect for warm welcoming of guests, cozy reading, quiet relaxation, and perhaps the occasional sleep over with the right sofa bed. The Chester River side (rear), with its set of French doors opening to a fully screened-in porch is a most inviting space for cooking, eating, mixing of cocktails, watching movies, gazing at the incredible sunrises or moon-lit water.  The shared dock provides access to a boat slip and even some Adirondack chairs to enjoy the many community events and water activities. Or just simply relax. The recently re-landscaped backyard provides for outdoor grilling, lounging, and a place for your bicycles and kayaks.
105 Water Street N 4
Chestertown, Maryland
  • 2 Beds
  • 2 Baths
  • 1,011 SqFt
Lovely rancher on over 3/4 of an acre.  Private country settling but only 10 minutes to town. Bedrooms are split with the owner's suite on one side and the two additional bedrooms on the other side.   Nice wood stove in the living room for a warm, cozy heat during the winter.  Beautiful hardwood floors throughout most of the house. Formal dining room.  Deck off the living room with pretty views of the back yard.  Large uninished basement.   $300 road maintenance fee.
27336 Preston Lane
Chestertown, Maryland
  • 3 Beds
  • 2 Baths
  • 1,770 SqFt
  • 0.840 Acres
Welcome to 335 Devon Dr in the coveted Coventry Farms community.  Sitting on a large corner lot, backing to open space, this home does NOT disappoint.  As you walk into this home and stand in the foyer, you have a view of every room.  This wide open floor plan is boasting over 3300 sq ft, 2 car garage, freshly painted,  and a surround sound system throughout the entire home!! To the left of the foyer is the large main level office with double glass doors.  To the right of the foyer you have the formal living room and dining room combo.  This space is large and brings in a ton of natural light. As you come back to the foyer and walk down the hall you enter into the main living space.  The home opens up to a massive family room, gorgeous kitchen and a bright and open sunroom.  The family room is large, with plush carpet, fireplace and is surrounded by gorgeous windows offering the beautiful view of the backyard. The kitchen is stunning.  Huge kitchen island, cooktop, double wall ovens and an abundance of cabinet and counter space.  The bonus of this space is the large sunroom with vaulted ceilings, large windows bringing in that natural light and it is overlooking the gorgeous backyard.  Finishing off the main level is the half bathroom and large laundry room.  Moving upstairs you have 4 bedrooms and 2 full bathrooms.  The secondary bedrooms are all massive and offer large double door closets.  The hallway full bathroom boasts double sinks, tile floor and a shower/tub combo.  Moving into the owner's suite.  WOW is the word you will say.  This room is beyond MASSIVE! So many upgrades.  Boasting custom tray ceiling, sitting space, 2 HUGE walk in closets and an owner's bathroom you have been looking for.  Soaking tub, tile stand up shower, double vanity, and tile floors.  You will fall in LOVE with this space!  Moving all the way downstairs you have a fully finished basement with brand new carpet and LVP flooring.  This space also offers a possible 5th bedroom!  The basement is large, open and offers a HUGE storage room.  This space just keeps on going!  Finishing off the basement is the sliding glass door to  the backyard.  Outback you have a large deck with stairs going down to the yard, a fully fenced in back yard with wrought iron fence, and it all sits on a large corner lot and backs to the open space!  No houses directly behind you!!! The location is prime, convenient to all shopping, restaurants, and minutes to downtown Chestertown.  Put this one your list of houses to see TODAY!!! You will NOT want to miss this one.
335 Devon Drive
Chestertown, Maryland
  • 4 Beds
  • 3 Baths
  • 4,874 SqFt
  • 0.260 Acres

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