Maryland Waterfront Homes for Sale 21620

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Featured Maryland Waterfront Homes for Sale 21620

Welcome to paradise! This incredible estate, situated on a bluff overlooking the Fairlee River will take your breath away. Situated in a peaceful, private setting, this masterpiece of a home is graced by soaring ceilings and abundant windows, incredible new renovations throughout such as the gourmet kitchen and spa-like baths, all thoughtfully designed to maximize it's best feature, the glorious water views. The finishes by Colebrook Designs (who you can find on Instagram) are some of the best you'll ever see The entryway draws you into the thoughtfully designed living area, created to delight the most descriminating host. The beautifully appointed great room adjacent to the chefs kitchen creates a dramatic focal point on the main level, accompanied by an elegant formal dining room and a secondary living area, which features another fireplace to create those cozy evening settings. The fully customized kitchen features amazing amenities such as luxury Cafe' appliances, many upgrades in the soft close cabinetry, the island that seats 7+ people, all with expansive water views. Upstairs, you'll find an open lounge area which opens to a spacious second floor balcony, one of many glorious outdoor spaces. Moving on to the bedrooms, if you desire easy one floor living this home provides a great opportunity featuring the most amazing first floor suite. With a soaking tub and walk in shower in the bathroom that's graced by skylights, and expansive water views from the bedroom, this is a space that you'll never want to leave. Dual walk in closets and a seperate seating area rounds out this magical space. Upstairs you'll find the two spacious guest bedrooms, served by another gorgeous full bath featuring a soaking tub of its own to round out the second floor. Back downstairs before you head outside you'll find a spacious laundry area, and a thoughfully designed first floor guest bath that also features a walk in shower for your convenience to clean up after enjoying watersports in the river. And through the breezeway to the 2 car garage, where you'll find a separate room that's set up as a gym, featuring it's own handbuild sauna! And finally outside, you'll adore the spacious cedar deck that's perfectly positioned to enjoy the broad water views. Besides the deck, this space features a custom outdoor kitchen and a covered patio area perfectly positioned for cool breezes to flow through on hot summer days, all set in the beautiful, mature landscaping that bursts into a riot of color in the spring and summertime. The newly rebuild dock features 5 boat slips as well as multiple lifts for jet skis and a boat, and super easy access to the great expanse of the Chesapeake, with 5-6 feet MLW depth at the dock. All of this is set in the beautiful neighborhood of Great Oak Landing, which features access to a 350 slip marina, restaurants, a community pool, beach, and a 9 hole executive golf course, all of which are a short walk or golf cart ride away, all for an annual membership fee of only $350! This will make an amazing home for its next owners, and would also make an amazing vacation rental for those who would choose to not live here full time. Make the most of your summers to come in this glorious home, come take a tour while it's still available!
10108 3rd Point Road
Chestertown, Maryland
  • 5 Beds
  • 4 Baths
  • 4,221 SqFt
  • 1.480 Acres
$1,995,000
Eastern Shore secluded waterfront home perched on the banks of the East Fork of Langford Creek offers commanding water views and encompasses 4.42 Acres and 235-feet of waterfront. This extraordinary waterfront property takes optimum advantage of its coveted setting offering vast water views from most rooms. Renovated in 2018-2019, the open design blends simple elegance and relaxing ambience with the latest luxury amenities. Pine wood flooring from a Vermont barn lends an inviting, casual feeling to the living areas. Thoughtfully designed, the 5-Bedroom, 3 and ½ Bath home features a first floor primary suite with a walk-in closet and a separate dressing room with vanity. Water views are also enjoyed from the first floor office library with pocket door. The flexible second floor design offers a central open sitting area overlooking the family room with two bedrooms and a full bath on each side. Expansive water views are a highlight of the kitchen. Opening to the family room and dining area, it features a generously sized island and high-end appliances including a 6-burner Viking Stove and Sub Zero under counter units. Inviting outdoor living and entertaining, the living spaces open to a large patio overlooking a 6-person hot tub, fire pit and a refreshing 24 x 45 heated salt water pool. The dock is just a short walk away to enjoy water activities and head out in your boat, while the outdoor shower is a popular stop on the way back to the house. The dock has a 15,000# boat lift and has accommodated a 31’ Grady White. There is also an additional fire pit down by the water. The screened porch is a perfect place to relax and spot wildlife. The privately sited home has additional amenities including HVAC with two zones, new roof, full house generator and a three car garage with one bay heated with storage above it. This property is a relaxing haven in perfect harmony with the enchanting eastern shore setting, The rural setting in the highly-desirable Pentridge Community is just a 10-minute pastoral drive from the historic riverfront town of Chestertown. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia, and 1-hour from Wilmington. Founded in 1706, Chestertown is set on the banks of the Chester River and is home to Washington College. Brick sidewalks are lined with period homes, shops, galleries, the Garfield Center for the Arts, restaurants, Stam’s Luncheonette, and The Retriever Oyster Bar. Enjoy the Sultana Education Center, the Chester River Walk, or experience a river cruise on the Chester River Packet. Residents and visitors alike enjoy the vibrant arts community, farmers market, parks, rails-to-trails and water activities. Annual events include the Chestertown Tea Party and the Sultana Tall Ship Downrigging Weekend.
6880 Pentridge Lane
Chestertown, Maryland
  • 5 Beds
  • 4 Baths
  • 3,931 SqFt
  • 4.420 Acres
$1,895,000
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! This exquisite three-bedroom, three-and-a-half-bath home 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
  • 2,700 SqFt
  • 0.030 Acres
$1,499,000
Sportsmans Paradise..... 3 Bed 2.5 Bath Cape Cod nestled on 36 acres, Granite kitchen counters, stainless appliances, hard wood flooring, Open floor plan concept, mud/laundry room off the side entrance. First floor Primary bedroom, 2 bedrooms upstairs with walk in closets and a jack & jill bathroom. Spare office room on 2nd floor as well. Out back a nice patio area & fire pit overlooking your Large 40'x60'x17' pole barn with 2 lean toos and a additional storage shed. On to the rest of the 36 Acres there is a trail running back to the main wooded area, 4 different access points to the property from both roads. There is 2 stocked fishing ponds, a waterfowl impoundment, theres been lots of time, money and effort spent here improving the habitat for for wildlife, including multiple food plots of clover a fruit orchard, buffer grasses & cypress trees. This property offers great deer, turkey, and waterfowl hunting and is a sportsmans dream come true. " Buy land, there not making it anymore "
411 Pine Tree Road
Chestertown, Maryland
  • 3 Beds
  • 3 Baths
  • 1,844 SqFt
  • 36 Acres
$1,099,999
Welcome to the Esau Watkins House (circa 1739), believed to be the earliest remaining dwelling on the Chester River in Historic Chestertown, the capitol of Kent County, Maryland. Rarely does a home of this significance become available in the heart of Chestertown’s famed Water Street district. This five-bedroom, three-and-one-half-bath historic gem offers captivating, unobstructed views of the unspoiled Chester River. Notable features of this home include extensive random width wood plank flooring, proportionally balanced trim work, gorgeous scalloped built-in corner cupboards, a sun-filled riverside enclosed porch, a living room with wood burning fireplace, spacious second-floor primary suite, adequate “step-in” closets, and storage, walk out full basement, lush waterside garden, and sea-walled frontage with pier deck for water access. This highly sought-after location is within a short, pet-friendly, walking distance to several well-reviewed restaurants, two delicious bakeries, intriguing boutique shops/galleries, and the highly acclaimed Downtown Chestertown Farmer’s Market. The Chester River offers endless watersports, world-class crabbing, fishing, kayaking, and undisturbed shoreline exploration. Chestertown is home to Washington College, the Chestertown Tea Party, and the sailing ship “Sultana.” Come Enjoy! Please note that the property history and previous listing information is incorrect!
109 Water Street N
Chestertown, Maryland
  • 5 Beds
  • 4 Baths
  • 3,030 SqFt
  • 0.090 Acres
$998,500
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
$995,000
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
$995,000
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
$950,000
Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite four-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 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
  • 2,720 SqFt
  • 0.070 Acres
$949,900
18th century historic home in downtown Chestertown with a separate carriage house! The main home features 3 bedrooms all with en-suite baths. The carriage house has an additional 2 bedrooms and 2 baths with separate laundry and a brick patio. Entrances to the property from Queen St. and Horsey Lane, 2 driveways with plenty of parking spaces. Original wood flooring throughout much of the house. The first floor features a living room, dining room, kitchen, and half bath. New owner to add vanity and toilet to one of the upstairs baths. Second-floor laundry room. Lovely landscaping and fenced-in yard between the main house and the carriage house. Just a short walk to the heart of downtown Chestertown. Definitely a rare find.
212 Queen Street N
Chestertown, Maryland
  • 3 Beds
  • 4 Baths
  • 3,756 SqFt
  • 0.530 Acres
$859,900
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 13
Chestertown, Maryland
  • 3 Beds
  • 4 Baths
  • 2,200 SqFt
  • 0.030 Acres
$855,000
Waterfront and low maintenance located less than 1 mile from Historic Chestertown! The home is thoughtfully designed with an attached garage and first floor ensuite to allow for main level living (present or future). The abundance of natural light that fills the interior highlights the architectural detail throughout and is further balanced by the neutral paint scheme and hardwood flooring. **Open floor plan, soft close cabinetry, 2 propane fireplaces, expansive unobstructed water views of the Chester, and more...
318 Landing Lane 30
Chestertown, Maryland
  • 2 Beds
  • 3 Baths
  • 0.030 Acres
$850,000
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
$815,000
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
$805,000
New price! Wait until you see this beautiful renovation! No detail has been overlooked in this open-concept historic Chestertown gem. The owners were able to achieve the perfect balance of updating the living space while maintaining the charm and character of the original house. Tall ceilings and thick moldings with high-end modern amenities give this property a one-of-a-kind feel. New kitchen with a large island, quartz countertops, gorgeous GE Cafe appliances. Both baths have been renovated and are some of the most beautiful we've seen. New HVAC, new roof and flashing. off-street parking with a garage/shed. The first floor features a living room, an open kitchen and dining area, a full bath, and a huge laundry/mud room. Doors lead out to the fenced-in yard and new patio. Behind the yard is an alley with off-street parking and the renovated garage/shed. The second floor has 3 bedrooms, an additional room that could be a bedroom if desired, and another stunning full bath. An additional bedroom or bonus room on the finished 3rd floor. Much of the original hardwood flooring remains. Fireplaces are non-functional but gas inserts could be added. Walking distance to all that historic Chestertown has to offer.
207 Queen Street N
Chestertown, Maryland
  • 4 Beds
  • 2 Baths
  • 2,244 SqFt
  • 0.100 Acres
$799,000
Welcome to 121 Lyons Lane in Chestertown! This stunning property offers the best of both worlds, a waterfront private wooded setting on 3.5 acres AND located within walking distance to the quaint shops and restaurants of Chestertown! Watch the sunset over Fishing Creek from the wrap-around front porch with the Chester River and downtown in the distance. The home offers 4 bedrooms, 2.5 bathrooms and a detached studio. The living room features hardwood floors made from reclaimed wood from Camden Yards baseball stadium in Baltimore, fireplace with pretty wood mantel, crown molding and beautiful water views. The dining room features crown molding and chair rail molding, providing an elegant space for gatherings. The sunroom, with its wrap-around windows, allows you to immerse yourself in the beauty of the outdoors. The kitchen features newer stainless steel appliances, new tile flooring, and a spacious Williams Sonoma marble top island with seating. The pantry closet offers ample storage space, and the laundry mudroom area from the garage provides added convenience. The main level also includes a powder room and a primary bedroom with an en-suite bathroom, ideal for one floor living! Upstairs, you'll find three spacious bedrooms, and generously sized closets. The bathroom has recently been gorgeously remodeled and showcases a large glass shower with a picture window overlooking the water, a separate soaking tub, a dual sink vanity and designer tile. Outside, you'll discover a screened-in gazebo, perfect for enjoying outdoor dining while taking in the tranquil surroundings. A separate fully-finished studio, equipped with its own climate system, offers endless possibilities as a home office, gym, or art studio. Situated on a private lot, this home also features outdoor sheds for additional storage, in addition to the large two-car garage with storage systems. The circular driveway provides convenience and ample parking. Three separate parcels combine to make the 3.5 acres, including one perc approved lot, which offers flexibility and potential for future expansion, guest house, etc. Just under a mile away is historic Chestertown with its quaint shops, delightful restaurants, vibrant Farmer's Market, and waterfront parks - all within walking distance. The sellers have an approved permit for pier that is valid until 2024 and can convey with the property. Chestertown Marina is also approximately 1 mile away. Don’t miss this incredibly special waterfront property!
121 Lyons Lane
Chestertown, Maryland
  • 4 Beds
  • 3 Baths
  • 2,327 SqFt
  • 3.500 Acres
$775,000
Prime location plus Guest house! This beautiful historic home boasts one of the most elegant modern interiors in town. It was completely gutted, rebuilt, and expanded in 2008. Top-of-the-line fit & finish includes mahogany decking, hardwood flors, new heat/AC in guest house, two on-demand hot water systems, pex plumbing, plus recent updates! Inside the front door, tall ceilings, cozy fireplace, and a peek of beautiful stained glass in the hall welcome you home! Step in further to reveal a truly breathtaking gourmet kitchen open to a sunny dining and family room area with a beautiful gas fireplace, covered brick patio and views of the charming guest cottage through colorful perennials! Upstairs, indulge in a spacious primary suite with an opulent ensuite bathroom, screened porch and plenty of closet space! Two more bedrooms, laundry, and another full bath complete the second floor of the main house. The fourth bedroom is the guest cottage nestled in the rear of the garden which beckons you outside! Stroll the brick walk through an established multi-season garden to this inviting destination! The turn-key guest quarters in the second floor of the cottage include a full bath, kitchenette, and full furnishings. An attractive outdoor spiral staircase, and balcony provide access to the guest quarters. The designer thoughtfully built in a removable railing section and a hoist beam that overhangs the balcony to assist in moving large items in case you ever want to refurnish. It's also just a fun way to send up a basket of goodies! The ground floor of the carriage house is a handy workshop fitted with lights & electrical outlets and a large double work sink. It has glass french doors that fully open to the garden. What a delightful versatile space for an art studio, man-cave / she-shed, or even expanded party space! It's enjoyed by the current owners as a potting shed and workshop. There is walk-in access from the street to the garden along the side of the house through a private gated alley. A few more highlights : Kitchen features: Thermador professional kitchen appliance suite. Premium granite island and counters. Custom cherry cabinetry. Huge custom stained glass window. Hall across from stained glass window leads to walk in pantry and a half bath with window. Rear great room open concept living. French doors to large covered brick patio downstairs and also to screened porch in master suite upstairs. Ingenious use of window placement to accentuate views and light while preserving privacy. incredible large master bath with clawfoot soaking tub, shower stall, double sinks, large counter, storage space, window with garden view and premium tile flooring. Front bedroom has a large closet and lots of western light. The third (middle) bedroom is currently configured as an office. It includes a corner armoire that conveys and a desk nook that might easily convert to a closet if desired. Partial basement provides standing headroom. It's accessed from an exterior staircase and has lighting, electrical outlets, easy mechanicals access, and a sump pump with a municipal-water-powered backup in case of power outage. The attic provides additional ample storage, accessible from pull-down stairs and has standing headroom , and is partially floored. LOCATION! Quiet, tree-lined Queen St is known for a friendly residential atmosphere, and lovely curbside gardens. This home is within a block of fine dining, artisan bread/coffee shop, clay studio, art galleries, performing arts, the County Court house, Ice cream/Luncheonette, the Saturday Farmer's Market, and just 2-3 blocks to 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
115 Queen Street N
Chestertown, Maryland
  • 4 Beds
  • 4 Baths
  • 2,496 SqFt
  • 0.090 Acres
$760,000
Escape to the Country!! Cedar-sided contemporary situated on 15 mostly wooded acres, with small pond and open areas for your animals, soccer field, or huge gardens. Home features large family room with gas fireplace, beautiful kitchen with stainless steel appliances and granite counters. Custom cabinets and built-ins, wood, laminate, and tile floors throughout. Screened porch for quiet evenings with hot tub hookup. Shed and outbuilding provide for endless options. RV hook-up at both the house and the 30 x 36 metal building (large open space with multiple smaller rooms with electric and heat). Chicken coop, air rifle only shooting range, basketball court, wooded acreage with walking or biking trail. Hunting is possible. Talkie Fiber WiFi is available. Metal building in good shape but being sold “as is”. Abandoned underground oil tank on site. This type of property does not often come to market… don’t miss out… Open House Saturday 4/22 (11am – 2pm). Home is on a shared R-O-W. No drive-bys.
118 Westwood Lane
Chestertown, Maryland
  • 3 Beds
  • 2 Baths
  • 2,248 SqFt
  • 15 Acres
$649,000
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