Maryland Waterfront Homes for Sale 21620

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Featured Maryland Waterfront Homes for Sale 21620

Beautiful Dutch Colonial on 3 Acres with 500 +/- feet of waterfront overlooking Worton Creek. Near Worton Creek Marina and only a short drive to Historic Chestertown or Rock Hall. Enjoy the wildlife, rural setting, and inground pool. Native plants create a very nicely landscaped home. All wall paneling is Western Red Cedar and the wood floors are 150+ years old heart pine. The game room could be used as bedroom #5. The family room has a brick wood burning fireplace, table space , breakfast bar, and exposed wood beams. Sign posted.

22900 Handy Point Road Handy Point Road

Chestertown, Maryland

5 Beds
5 Baths
4,885 SqFt
3.130 Acres

SMITH-RINGGOLD HOUSE.
This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort. Originally a merchant’s home in the heart of historic Chestertown, the Smith-Ringgold house has been modified representing four defined periods and enlarged over the course of its 250-year history. The present owner took two years to restore the home’s structural integrity from the foundation to the attic, adding a river-side addition and porch, replacing the cedar shingle roof, and completely redoing the plumbing, wiring, heat and A/C systems. The wood floors throughout the house have been beautifully restored. Modern storm windows are energy efficient and all but eliminate street noise. Aside from your own personal touches, this house is move-in-ready.

The ground floor has a large double parlor, cozy sitting room, formal dining room, breakfast room, and a stunning chef’s kitchen. An important feature is the hand painted dining room mural by noted artist Jack Schroeder. The front hall, redesigned in about 1860, replaced a steep stairway with a grand and gracefully curving staircase. The second floor contains three large en-suite bedrooms and a laundry room that is also accessible from the kitchen via a “secret” staff stairway. The third floor has a large sitting room, bathroom, and bedroom, with part of the home’s original c. 1759 roof forming a unique design element. The backyard was extensively terraced, probably in the late 1700s, in descending levels down to the Chester River. The free-standing brick garage dates from the early 20th century, when car garages replaced horse barns. This structure could easily be repurposed as an artist’s studio or home workshop. A wide driveway area provides additional off-street parking.

Truly an inviting residence for intimate family evenings or grand parties. Perfect setting for one's collection of antiques or for the simplicity of contemporary furniture which emphasizes the wonderful architecture.

CHESTERTOWN IN THE COUNTY OF KENT

Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities. Chestertown is home to a surprisingly large number of elegant, historical Georgian homes as well as Victorian “painted ladies.” With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City.

Centrally located Washington College (founded in 1782 with the personal support of George Washington) provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers. The town boasts a weekly Farmers Market, excellent coffee bars, restaurants, and art galleries—but no big box stores. The Chester River Yacht & Country Club offers an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party, commemorating a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. Today Chestertown is a vibrant mix of old families, newcomers, college students, full time residents with children, and involved weekenders.

201 Water Street N

Chestertown, Maryland

4 Beds
5 Baths
5,195 SqFt
0.390 Acres

Introducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester River Landing. Hands down, one of the best lots in the community! The Schooner model is an exquisite three-bedroom, three-and-a-half-bath home that offers luxurious living and breathtaking, panoramic views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Little Harbor Way 1

Chestertown, Maryland

3 Beds
4 Baths
2,315 SqFt
0.030 Acres

"Strawboard Mill" offers 2 brick, townhomes (each townhouse has 2 units), with metal roofs, 1 efficiency apartment and a 3 bedroom, 2 bath residence. The brick townhomes were built in 1902+/- and were used as housing for mill factory workers. There are two, 2 bedroom, 1 bath units in each townhome. Each townhome unit has washer and dryer. The efficiency unit also has a washer and dryer. All units are leased on a month to month basis. All townhome units have Lead Free Certificates from MDE. The main house, which houses the efficiency unit over the garage, was built in 2005. Current monthly rental income is $5,225 with the potential to increase to market level of about $6,500+/- and even more if you rent out the main house. The owners live in a well appointed Cape Cod that offers the possibility of a 1st floor bedroom, kitchen and family room as well as office space, 2 additional bedrooms on the second level with a "Jack n Jill" bathroom setup. There are laminate floors throughout most of the house as well as wood ceilings in most rooms. There are actually 2 garage spaces however one has been transformed into an exercise room. The rear deck overlooks the private backyard and offers a gazebo on the deck. Do you need a separate office? You are in luck! There is an attached office space with a mini split system for heating and cooling. The sellers live in the Cape Cod however you could easily rent the house to gain more income. There is potential to increase the current rent rolls to meet current rental market values. This is a rare opportunity to own, arguably, one of the finest rental properties in Chestertown!

131, 133 and 129 Flatland Road

Chestertown, Maryland

3 Beds
2 Baths
4,684 SqFt
0.510 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

226 Water Street S

Chestertown, Maryland

3 Beds
4 Baths
0.090 Acres

This remarkable 4BR/3.5BA waterfront home boasts historic elegance and beautiful water views! The best of both worlds, this property is located on the Chester River, offering the relaxing water-oriented lifestyle while also being walkable to all the great restaurants and shops that downtown Chestertown has to offer! This historic gem, built in 1900, sits on a .22-acre lot, offering you space and privacy in the heart of Chestertown. Step inside and be awestruck by the expansive foyer leading to the great room with its soaring ceilings, creating an open and inviting atmosphere. Stained glass doors and windows, 2 fireplaces with Quimper and Delft tiled surrounds, and original hardwood flooring are some of notable details throughout this special home. With over 5,400 square feet of living space, there's room for everyone to enjoy and endless potential! An unexpected treat, the home has an indoor pool for year-round relaxation and entertainment. Additionally there is an attached 2-car garage, a very rare find in downtown. The large covered brick patio is ideal for outdoor entertaining overlooking the lawn and Chester River.

205 Water Street N

Chestertown, Maryland

4 Beds
4 Baths
5,426 SqFt
0.220 Acres

228 Water Street S

Chestertown, Maryland

3 Beds
4 Baths
0.060 Acres

Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. The Sultana model is an exquisite four-bedroom, two-and-a-half-bath home that offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Lane 25

Chestertown, Maryland

4 Beds
4 Baths
2,784 SqFt
0.070 Acres

This contemporary waterfront property offers the perfect blend of modern living and waterfront serenity. The open floor plan affords views of Mill Creek from every room. The first floor features a three sided fireplace, a gorgeous great room with floor to ceiling windows/doors, gourmet kitchen which opens to the dining area, plus two bedrooms and two full baths. Upstairs you have a cozy loft area perfect for curling up with a book or for tv. There's also another bedroom and full bath and an office with a balcony looking over Mill Creek. Most of the furniture will convey!

If you enjoy outdoor living this property is for you. There's a screened porch - the perfect setting for a crab feast! Plus a wrap around deck for relaxing and entertaining. The property includes private access to Mill Creek, making it perfect for boating, kayaking, and other water activities. And for those needing deeper water you will find Worton Creek Marina right around the bend!

10761 Kasota Road

Chestertown, Maryland

3 Beds
3 Baths
2,382 SqFt
0.840 Acres

Check out Chester River Landing's newest construction! This middle unit, three bedroom, three and a half bath townhouse is spacious and has incredible views of the Chester River. Built with the finest finishes, the main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln 12

Chestertown, Maryland

3 Beds
4 Baths
2,200 SqFt
0.030 Acres

Check out Chester River Landing's newest construction! This three bedroom, three and a half bath, townhouse is a spacious end unit with incredible views of the Chester River and is built with the finest finishes. The main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln 11

Chestertown, Maryland

3 Beds
4 Baths
2,200 SqFt
0.030 Acres

This pre-1900 rowhouse over-looking the Chester River and situated on South Water Street was expanded in 2013 to maximize its water-view living, both indoors and outdoors. Featuring four bedrooms, two and one-half baths, attached garage, the first floor features a traditional parlor with gas fireplace with original mantel and built in bookcases, traditional dining room, nice sized galley kitchen transitioning to an open-spaced great room, eating area and island seating. A large two-story deck that has hosted many fireworks parties and the occasional concert on the riverfront is accessed from the great room and second floor primary suite. Primary suite includes office space or nursery, dressing room, and walk-in closet. Primary bathroom houses full size washer and dryer encased with beautiful cherrywood cabinetry. This small row of houses is often photographed and admired by Chestertown visitors, similar to the colorful and well-preserved row houses in Charleston SC

105 Water Street

Chestertown, Maryland

4 Beds
3 Baths
2,565 SqFt
0.050 Acres

This former horse barn was converted in 1990 into a well-crafted personal residence. In early 2018, the current stewards retained acclaimed contractors Taylor Loughry to apply their craftsmanship to a large portion of the house. The most delightfully unique characteristic of this 4-5 bedroom, 3 and 1/2 bath home with attached two car garage is its' private, landscaped lot accessed by a gravel driveway on North Water Street. A pair of new wood gates define the entry to the oasis. The redesigned flow of the first floor provides well for the intended purpose of both entertaining and home comfort. A den, powder room, and elevator adjoin the two-story, sun-filled foyer. A large living room with gas fireplace and separate dining room (with doors to the rear brick patio and raised beds) provide the pathway to a beautifully designed large island kitchen with breakfast area with bay window. Mudroom with sink, full sized washer and dryer and storage is adjacent to a side entry and double garage with EV charging station. Floor two comprises mostly a primary suite that includes bath, large office and exercise space with access to a very large, insulated and conditioned storage space (easily repurposed to a games room or home theatre), a guest bedroom and hall bath. The third-floor features two additional bedrooms and bath with large amounts of closet space. Recently installed solar panels, discreetly positioned, have resulted in nearly net zero energy expense.

106 Water Street N 1/2

Chestertown, Maryland

4 Beds
4 Baths
2,866 SqFt
0.140 Acres

This incredible home with seasonal water views of the Chester River is positioned on a private lot on Aldan Dr in Chestertown. Inside the beautiful foyer are gleaming hardwood floors with the formal dining room on the left, and a living room on the right. The architectural detail with crown molding, columns and beautiful light streaming in continues throughout this gorgeous home. This custom kitchen is a cook's dream, with a five-burner gas Thermador stove, two wall ovens, a warming oven, all stainless-steel appliances. There is a breakfast room that overlooks the gorgeous back yard, which has a deck, and a screened in porch for outdoor living. Just beautiful! The great room has 19' ceilings, a gas fireplace and multiple built-in cabinets that will showcase your treasures. There is a terrific owner's suite with a large bathroom, featuring a walk-in shower complete with a convenient bench, a separate bathtub, and two sinks for even more convenience. The walk-in closet is off the bathroom and has a very nice California closet system for maximum storage. There is an on demand hot water system and coded garage doors in the two-car garage. Amenities include an alarm system, pocket doors, and a nice pantry. There is plenty of storage throughout this home. Upstairs, the hardwood floors continue with three bedrooms, one of which is an ensuite, and two of the bedrooms have a jack and jill bathroom with double sinks. The bedrooms have walk-in closets. There is also a bonus room with walk in access to storage room that is floored. Yard has automatic zoned sprinkler system with drip in most beds. Of note, a portion of the back yard is in a flood zone.

7996 Aldan Drive

Chestertown, Maryland

4 Beds
4 Baths
3,743 SqFt
1.110 Acres

Welcome to the former historic HILLTOP HOTEL! A charming estate which underwent significant renovations in 2021 while preserving many of the original characteristics the home has to offer. This property is unlike any other - offering historic charm, tranquil atmosphere, ample privacy, outdoor living & entertaining as well as turnkey amenities. The property sits perched high above the hillside of the Eastern Shore providing for stunning sunsets as you relax on the wraparound porch feeling the gentle breeze from the Chesapeake Bay. As you enter and proceed up the gravel driveway you are greeted by a large circular drive, beautifully manicured lawn, 4.74 acres of mature landscaping and the grandeur of the 3 story historic home. The first and second floors have been updated to include bright new paint throughout, remodeled kitchen offering an abundance of natural light, all new appliances, french doors were installed off the kitchen and study leading out to a new beautiful brick terrace overlooking scenic countryside views, updated powered room on the first floor, primary second floor bath has been completely remodeled to include updated amenities. The second floor offers 3 bedrooms, 2 full baths along with a spacious laundry room. As you make your way up to the third floor you immediately noticed the extensive renovations. Every aspect of the third floor was meticulously remodeled and redesigned including new insulation, new plumbing, new electric, new drywall, new commercial grade HVAC system and all 14 windows throughout the third floor were replaced. The third floor offers 3 bedrooms, 1 full bath and large beautiful living area.

All hardwood floors throughout the home were refinished to their original beauty. New commercial grade water treatment system was installed. The wraparound porch was completely painted and all porch columns were wrapped. The exterior back of the home was sealed and painted. New roof installed. Both chimneys were repointed. Dual zone HVAC.

This is a COMMERCIALLY ZONED property - Zoned Crossroads Commercial. Perfect for B&B or commercial use.

Centrally located between historic Chestertown, MD and Rock Hall, MD.

Owners are open to selling property furnished with the exception of several items.

7979 Sandy Bottom Road

Chestertown, Maryland

6 Beds
4 Baths
3,696 SqFt
4.740 Acres

This cottage on Fairlee Creek is simpy adorable!!In a protected cove with a quick run to the Bay. Love the feel of this open home with a huge back screened in porch. This home has been a gathering place for three generations and the family is ready to pass this on to the next lucky owners. Tons of sleeping space with two bedrooms on the first floor and an open loft with multiple space to sleep or have an additional family room. Walk out to a well maintained pier, and dock your boats, or jet skis and stay a while. It is down a private road with only a few other homes and an expansive water view. This home was added on in 1998-2000 along with the septic, central AC and the porch, roof and pier. Very recent improvements are painting throughout, new fence, new french drain, newly refinished wood floor on back porch , new screens on back porch. Don't miss your chance to own this piece of tranquility .

9762 Vogeler Drive

Chestertown, Maryland

2 Beds
2 Baths
1,521 SqFt
0.460 Acres

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln 37

Chestertown, Maryland

3 Beds
3 Baths
1,964 SqFt
0.060 Acres

Maryland Waterfront Communities

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