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Chestertown MD Real Estate & Homes for Sale

35 Properties Found

The median home value in Chestertown, MD is $324,500. This is higher than the county median home value of $249,900. The national median home value is $308,980. The average price of homes sold in Chestertown, MD is $324,500. Approximately 44% of Chestertown homes are owned, compared to 42% rented, while 14% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chestertown real estate agent to arrange a tour today!
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Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
3,355
Status:
NEW LISTING
MLS#:
MDKE2003972
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.18 Acres
Year built:
1936
Courtesy: Doug Ashley Realtors, LLC
View additional info

A stunning renovation in the historic district! This stately brick colonial overlooks the meticulous campus green at Washington College; a view that invites a walk to downtown Chestertown, and a location that gives you a front row seat to college activities and events. It is also one short block to the University of Maryland Shore Medical Center. A desirable rear alley, provides access to the home's private off-street parking space and the carriage-styled garage, which can accommodate a SUV. Located on the first floor off the center hall,Âis the living room, dining room, kitchen, den/office, half bath, all- season sun room, and inside stairs to the full basement, The new custom kitchen showcases an individually handcrafted brick floor and an imported Spanish tiled backsplash. Wrap around natural lighting, open shelving, oversized island and walk in-pantry make this kitchen one of a kind, and completes the first floor. The second floor begins with the original grand stairway and a cozy sitting area in the window nook at the end of the catwalk. The primary bedroom comes with a five piece luxury en-suite bath, while two additional bedrooms share a full bathroom off the landing. The dedicated laundry room, also on the second floor, has storage cabinets, room for ironing and folding and a cleaning supply niche. The third floor garret-studio apartment completes the living areas inside this home. This spacious studio has a full bathroom, dedicated cooking & eating area and independent climate control. A comfortable sitting area and separate sleeping space, and separate desk space round out this studio. There is also a Âfull basement of approximately 1100 square ft with both interior access and a highly coveted exterior access. 7.5 foot high basement ceilings, provide an excellent opportunity to design an additional apartment, fitness studio, family room, wood shop etc. Exterior and mechanical upgrades include: a new roof, gutters & downspouts, a new front landing with oversized walkways and raised brick landscape beds. Significant wiring upgrades include a new electrical service and wiring for new electrical components. Plumbing upgrades include a new main shut off valve and a new water line between the house and street. Replacement of most of the interior plumbing was done to accommodate updated fixtures. The one-car, carriage styled garage has been placed for optimum versatility. It makes a charming extension of the outdoor entertaining space to effortlessly plan for changeable Chesapeake-country weather. Simply move the car, open the barn doors, turn on the the oversized crystal chandelier and the tone is set for gatherings protected from the elements! With the double barn doors opened, Âthe terraced courtyard can be incorporated into any event. This property is fully fenced & gated providing privacy for outdoor activities and security for family pets. This brick center-hall colonial Âhas been extensively renovated and is turn-key! Square footage is estimated: buyer to verify. A complete upgrade record is available upon request. Talk to your agent about possible owner financing on this home.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,376
Status:
NEW LISTING
MLS#:
MDKE2003962
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.26 Acres
Year built:
1956
Courtesy: Doug Ashley Realtors, LLC
View additional info

Clean, classic mid-century style ranch with REAL wood floors. archways, knotty pine kitchen, a big front porch, large yard, off-street parking and bonus alley access in rear with possible room for a detached garage (buyer to verify) New upgraded electrical service and GFCI outlets, fresh paint, floors refinished and more. Walk to conveniences from this move-in ready charmer in upper Chestertown.

Beds:
4
Baths:
5 Full
Sq.Ft.:
3,497
Status:
NEW LISTING
MLS#:
MDKE2003998
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.14 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Price improvement! This building has been converted into 4 apartments. All units are currently rented. Limited interior photos to respect tenant privacy. Landlord pays all utilities. 128 North Queen Street, built in the beautiful Queen Anne style is one of the finest 19th-century houses in the Chestertown Historic District. The house is a block from the Chester River, close to Washington College and two blocks from downtown, shops, and the Chestertown Marina. It was designed by Baltimore Architect ,Benjamin Owens. The building served as the Methodist Parsonage for the Christ Methodist Church on High Street soon after he designed the church in 1887. The multi-gabled house is asymmetrical, filled with light from large double-hung windows, with a three-story turret in one corner large enough for a desk from where you can view the Chester River. Hardwood floors are located throughout. A beautiful original polished staircase with turned and polished wood balustrades rises from the central hall. Original stained glass windows shimmer with color in the main staircase and a second-floor bathroom which retains an amazingly large claw foot bathtub with polished wood surround. A slate surround and carved wood fireplace mantel center the den and living area on the first floor. The building is heated by a one year old boiler and cooled by a one year old heat pump system. Unit 1 is an efficiency. Rent $980 Unit 2 is 2 stories and 2 bedrooms with a washer/dryer. Rent $1850 Unit 3 is a 1 bedroom with a turret. Rent $1300 Unit 4 is a 1 bedroom with a turret. Rent $1200 Last year's electric: $4331 Last year's oil: $3215

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
MDKE2003926
Type:
Single Family, Single Family-Detached
Subdivision:
Prestwick
Lot size:
1.83 Acres
Year built:
2024
Courtesy: Gunther-McClary Real Estate
View additional info

Live in Luxury in this brand new home that seamlessly blends indoor-outdoor living with its prime location on nestled just off of the 10th tee box of the Chester River Yacht and Country club. Enjoy the convenience of this 3 bedroom, plus extra room for office, gym or playroom, 2.5 bath home full of light with a modern open floor plan with one floor living. Harwood Oak floors throughout whole house. The kitchen comes complete with stainless steel appliances, hood vent, Large island with ample countertop space and a butler's pantry that adds functionality and organization. Beautiful primary bath and massive walk-in closet with lots of shelving and hanging rods for all those who have a love of fashion. Front porch to have your coffee's and a back screened-in porch to entertain and watch the golfers. Every aspect of this property has been thoughtfully considered to create a living space that is both functional and breathtaking. Note tax record reflects current lot taxes and will be updated once Certificate of Occupancy is issued. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area s finest builders.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,200
Status:
Active
MLS#:
MDKE2003936
Type:
Single Family
Subdivision:
Chester River Landing
Lot size:
0.07 Acres
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional info

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!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,200
Status:
Active
MLS#:
MDKE2003948
Type:
Single Family
Subdivision:
Chester River Landing
Lot size:
0.07 Acres
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional info

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!

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
3,232
Status:
Active
MLS#:
MDKE2003854
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
1.58 Acres
Year built:
2011
Courtesy: Cross Street Realtors LLC, 4434803453
View additional info

Built on a 40-foot bluff overlooking the Chesapeake Bay facing west for nightly sunsets, this is a tour-de-force of design and luxury on the Eastern Shore of Maryland, with truly stunning views from every room. Follow your dreams with this resort-like property as a primary or secondary home. Drive along the maple-lined lighted drive to 1.5 acres of award-winning, irrigated, landscaped grounds designed by South Fork Studio. Walk through the mahogany gate into the courtyard with fountain along the bluestone path around the Gunite pool. The main house on the water (c. 2011 and updated in 2018) has 3 bedrooms and 2 and 1/2 baths, and a wall of large windows with an automatic shade system that follows the sun's path. Open floor plan living with private first-floor owner's suite (double shower, Toto washlet, and custom walk-in closet). Wake up to views of the Bay and Bald Eagles fishing. Custom hand-crafted hardwood flooring, millwork, cabinetry, and New Zealand wool carpeting. Built-in Sub-Zero and Wolf appliances and top-of-the line luxury materials throughout. Automated control for whole-home media and sound, lighting, HVAC, irrigation, swimming pool, alarm system, and window shades. Gas-started wood-burning fireplace in the living room. Ipe decking, 3 outdoor showers, and numerous spaces to entertain friends and family. A custom-lighted staircase and brand-new dock (2023) with boat lift and large Ipe dining table sit above the rip-wrapped shoreline. The guest house and three-car garage, designed by Purple Cherry Architects and built by the acclaimed Taylor-Loughry partnership in 2019, cleverly create the privacy, mystery and architectural stature of the entire four-parcel domain. Currently, the guest house presents 1 bedroom, 1 full bathroom with laundry, a kitchenette and a very large multi-purpose room with cathedral ceiling that overlooks the center core of the gardens, saltwater and heated pool, custom cedar pergola, and Chesapeake Bay. The pool building contains the latest technology in pool filtration, whole-property water filtration system, well pump, irrigation system, pool heater, and storage. There is also on-demand hot water throughout the property and radiant heated flooring in all full bathrooms. This property awaits a most discerning and capable buyer yearning for a discreet and well-designed lifestyle. Only 15 minutes from historic downtown Chestertown.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,045
Status:
Active
MLS#:
MDKE2003778
Type:
Single Family, Single Family-Detached
Subdivision:
Byford Development
Lot size:
0.34 Acres
Year built:
1976
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Lovely Cape Cod in desirable Byford Heights. First-floor Primary Bedroom and Bathroom. 2 large bedrooms with full Bathroom on 2nd floor. Beautiful Hardwood floors. Easy flowing floor plan guides you from bright living room to the dining room and then the kitchen. The Kitchen has lots of quality cabinets and space for a kitchen table. The kitchen overlooks the Family Room with Fireplace for cozy evenings. Want to sit outside, enjoy the extra large screened-in porch. Off the porch is a Fenced- in Dog Run. Plenty of room for tables and lounge furniture.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,964
Status:
Active
MLS#:
MDKE2003932
Type:
Single Family
Subdivision:
Chester River Landing
Lot size:
0.05 Acres
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional info

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!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,964
Status:
Active
MLS#:
MDKE2003934
Type:
Single Family
Subdivision:
Chester River Landing
Lot size:
0.06 Acres
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional info

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!

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE2003862
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.05 Acres
Year built:
1955
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Welcome home to Tolchester Village. This 2 bedroom 1 bathroom townhome is short distance to Rock Hall or Chestertown. This efficient townhome offers a tranquil setting with an abundance of wildlife in a park like setting just of the back patio area for entertaining. Plenty of parking in this 18 unit community.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
4,730
Status:
Active
MLS#:
MDKE2003814
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.61 Acres
Year built:
2011
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
2
Baths:
2 Full
Sq.Ft.:
864
Status:
Active
MLS#:
MDQA2009482
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.5 Acres
Year built:
1930
Courtesy: Village Real Estate Company LLC
View additional info

Wonderful renovation, modern, efficient, and move in ready! Home features vaulted ceilings with open flexible floorplan and 2 brand new luxury bathrooms. Energy efficient instant hot water heater. Large side deck, plenty of parking, small storage shed, and updated BAT system septic. Spacious yard for a garden and family events. Can't pass up this AFFORDABLE price point for like new construction, but not a townhouse!

Beds:
2
Baths:
1 Full
Sq.Ft.:
729
Status:
Active
MLS#:
MDKE2003730
Type:
Condo
Subdivision:
Chestertown Historic District
Year built:
1886
Courtesy: Gunther-McClary Real Estate
View additional info

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 2 Bed 1 bath has a brand new kitchen and upgraded bathroom along with broad southeast river views.

Beds:
1
Baths:
1 Full
Sq.Ft.:
850
Status:
Active
MLS#:
MDKE2003732
Type:
Condo
Subdivision:
Chestertown Historic District
Year built:
1886
Courtesy: Gunther-McClary Real Estate
View additional info

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 1 Bed 1 bath has a brand new kitchen, with island, and upgraded bathroom along with up and down river views.

Beds:
2
Baths:
1 Full
Sq.Ft.:
787
Status:
Active
MLS#:
MDKE2003742
Type:
Condo
Subdivision:
Chestertown Historic District
Year built:
1886
Courtesy: Gunther-McClary Real Estate
View additional info

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views.

Beds:
1
Baths:
1 Full
Sq.Ft.:
652
Status:
Active
MLS#:
MDKE2003722
Type:
Condo
Subdivision:
Chestertown Historic District
Year built:
1886
Courtesy: Gunther-McClary Real Estate
View additional info

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 1 Bed 1 bath has a brand new kitchen, with island, and upgraded bathroom along with up and down river views.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,660
Status:
Active
MLS#:
MDKE2003760
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
1.25 Acres
Year built:
1945
Courtesy: Gunther-McClary Real Estate
View additional info

Beautifully renovated waterfront on the Chester River, located between historic downtown Chestertown and the Chester River Yacht and Country Club. Renovations include including new kitchen and bathrooms. This property boasts a deep water dock with lift for your boating, swimming and fishing pleasures. Come and enjoy all the Chestertown has to offer with just a short walk to down town shops, restaurants and parks..

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
4,804
Status:
Active
MLS#:
MDQA2009012
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
9.58 Acres
Year built:
2010
Courtesy: TTR Sotheby's International Realty, (410) 673-3344
View additional info

Every so often a property like 240 Round Top Landing Road, Chestertown hits the market that checks all the boxes. This Chester River waterfront estate is situated on 10 acres , offering deep water, pier, 25' x 50 ' in-ground pool, screened porch , 3 bedroom/3.5 bath main house and a carriage house. The architectural design and the superb craftsmanship are evident as soon as you enter the driveway. Beautiful trees(Peach,Pear, Pines, Poplars, Sycamores, Magnolias' Crepe Myrtles) enhance the park-like setting. Notable features are geo-thermal heat; gas and wood burning fireplaces, chef's kitchen; first floor spacious primary bedroom suite , and open living areas. As far as the exterior, the stucco siding is either over brick or block so no stucco is over frame. Some poplar siding on main house and cedar siding on carriage house.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,512
Status:
Active
MLS#:
MDQA2009262
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.39 Acres
Year built:
2024
Courtesy: Cross Street Realtors LLC, 4434803453
View additional info

New construction, almost done! Updated pictures coming soon!! Anticipated completion May 1st. This 3-bedroom, 2.5-bathroom Cape Cod boasts water views of the Chester River. Featuring an open-concept layout, stainless steel appliances, and a main-level master with walk-in closet, and ensuite. Upstairs, discover two generously sized bedrooms accompanied by an additional full bathroom. Located at the end of a quiet, private street. *Current interior photos are of another home built by the same builder - for informational purposes only*

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
6,459
Status:
Active
MLS#:
MDKE2003704
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale Properties
Lot size:
3.95 Acres
Year built:
2000
Courtesy: Doug Ashley Realtors, LLC
View additional info

Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road, creating a sense of grandeur and privacy. Nestled on the shores of an oversized pond, this exquisite home offers not only stunning views but also exclusive access to a community dock and dedicated boat slip with a lift onto Fairlee Creek. Originally built in 2000 and impeccably maintained and updated, this home welcomes you with a beautifully designed foyer that sets the bar for living beautifully. The living room, open to a gracious dining area, exudes warmth and hospitality, making it the perfect setting for gatherings with loved ones. French doors beckon you to the covered patio, where you can bask in the serene ambiance and enjoy the sights and sounds of nature. Below, the guinite pool invites you to relax and unwind, surrounded by ample space for poolside lounging and entertaining. The main level boasts four bedrooms, including a luxurious owner's suite complete with a cozy gas fireplace and direct access to the pool area. The master bath is a sanctuary in itself, featuring separate vanities, a spacious walk-in shower, a soothing soaking tub, and generous storage space. The second bathroom, versatile in its design, offers built-in bookshelves and two closets, making it ideal for use as an office or guest suite. A convenient half bath, with access to the pool, adds to the home's functionality and convenience. The recently updated kitchen is a Cook's delight, equipped with an island, ample storage, and all the necessary appliances. Adjacent to the kitchen, the family room beckons with built-ins, a fireplace, and abundant natural light, creating a cozy yet inviting atmosphere. The Florida Room, bathed in sunlight, offers a perfect spot for plants and relaxation, with seamless access to the pool area. Two additional bedrooms, one with an attached sitting room, and a full bath complete the main level, ensuring comfort and convenience for all. Downstairs, a newly added bedroom and bathroom, along with a spacious great room, provide endless possibilities for entertainment and recreation. The expansive storage room offers potential for additional living space or customization to suit your needs. Upstairs, the attic boasts a large cedar room for storage, with even more space available if needed. The quality of construction is evident throughout, ensuring durability and longevity for years to come. Don't miss this opportunity to experience the beauty and serenity of waterfront living at its finest. Schedule a viewing today and make this exquisite property your own slice of paradise in this great neighborhood.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,408
Status:
Active
MLS#:
MDQA2009122
Type:
Single Family, Single Family-Detached
Subdivision:
Queen Annes County
Lot size:
0.69 Acres
Year built:
1900
Courtesy: Blackwell Real Estate, LLC, (443) 221-4120
View additional info

Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek! Features Include: Screened Porch * 1-Car Attached Garage * Tilt-in Insulated Double Pane Windows * Large Living / Dining Room Combo with Brick Accented Gas Fireplace * Updated Kitchen with Stainless Steel Appliances * Separate Laundry Room off Kitchen * 2 Generous Sized Upper Level Bedrooms + a Large Bathroom with Separate Make-Up Table. * Dual Zone Central Air, Dual Zone Hot Water Baseboard Heat * Full RV Hookup with Water, Sewer & Electric in Back Yard. *As Per 2021 Listing, 2011 BAT System Upgrade Allows For The Addition of a 3rd Bedroom* Conveniently located just minutes from all the shops and restaurants Chestertown has to offer, this quaint property offers a little rural lifestyle without the isolation!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,128
Status:
Active
MLS#:
MDQA2008806
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.2 Acres
Year built:
1954
Courtesy: Taylor Properties
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Price Improvement! Welcome to this cozy 3 bedroom, 1 bath remodeled Swiss cottage with views of the Chester River and a lovely yard full of mature gardens. Located in Queen Anne's County, Chestertown, MD, the sounds of geese and local birds fill the air on this quiet private road. New Mitsubishi heating/air conditioning mini splits, new Thompson Creek-50 year warranty siding with upgraded insulation. New windows and doors with the exception of antique glass. New Stiebel Eltron electric tankless hot water heater, new Maytag washer & dryer, new Frigidaire stainless-steel appliances, LVP floors, new carpet in bedrooms and living room, fresh paint and new lighting throughout, plantation shutters and new window treatments throughout, solar panels to help absorb energy costs, and high speed internet. Home has new front steps, new seamless gutters, 12 x 16 treated lumber deck at rear entry, and 10 x 12 shed with new siding, windows, and tin roof. Enjoy peaceful days and nights at this beautifully remodeled, highly efficient home, with the masterfully planned mature gardens with slate walkways and stone boarders. The yard is abundant with perennial flowers, shrubs, Dogwoods, and Cherry Blossom, perfect to enjoy your morning coffee or evening sunsets. Some of the annual events and festivals include the Chestertown Tea Party and Tall Ship Down Rigging. Residents and visitors alike enjoy the vibrant arts community, restaurants, shopping, the Saturday Farmers/Artisan Market, parks, railsto-trails and water activities. Just 2 miles to Deep Landing Boat Ramp and 25 minutes to the Chesapeake Bay Bridge or Middletown, DE. This home has it all! Must See! Owners offering $4,000 cabinet painting credit and willing to help on closing costs.

Open House:

Friday, 5/24 3:00-5:00PM

Beds:
2
Baths:
2 Full/1 Half
Sq.Ft.:
2,210
Status:
Active
MLS#:
MDKE2003556
Type:
Single Family, Single Family-Detached
Subdivision:
Orchard Hill
Lot size:
1.89 Acres
Year built:
1992
Courtesy: Chesapeake Real Estate Associates, LLC
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Welcome to your tranquil retreat at Orchard Hill, where modern sophistication meets peaceful living on 1.89 acres of beautifully landscaped grounds. This stunning Cape Cod style home offers an abundance of amenities and thoughtful details throughout. As you step inside, you're greeted by the grandeur of vaulted ceilings that create an open and airy atmosphere. The ground floor primary bedroom provides convenience and luxury, complete with a upgraded kitchen featuring granite countertops, quality stainless steel appliances, an island with a gas cooktop, and a built-in wine refrigerator. The primary bedroom is a true sanctuary, featuring a luxury primary bath with a jetted tub and a stylish tile shower with glass doors. The main level's open layout is perfect for entertaining, with the added convenience of a bar with a sink. The second floor offers a guest bedroom, a full bath, and a loft that could easily be converted into a third bedroom or utilized as a versatile space according to your needs. Outdoor living is equally impressive, with a screened porch, large composite deck with a retractable canopy, a gazebo, and beautiful English cottage gardens featuring many native plants. The expansive outdoor space is perfect for gardening, outdoor activities, or simply enjoying the serene surroundings. Backing to trees and farmland, this property provides a peaceful backdrop and ample privacy. It's truly a must-see for those seeking a blend of modern luxury and peaceful countryside living. Schedule a showing today to experience the beauty and serenity of this exceptional property at Orchard Hill.

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,150
Status:
Active
MLS#:
MDKE2003374
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.46 Acres
Year built:
1949
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Price improvement! Two perfectly adorable cottages in Tolchester. Both were completely remodeled. The cottages sit on 3 lots totaling about .46 acres. Each has one bedroom, a full bath, kitchen and living areas. The front cottage also has an additional "sleeping loft". Tolchester Beach is located on the Chesapeake Bay and has a beautiful beach and boat ramp. Walking distance to The Shanty Beach Bar and the Tolchester Marina. A great place to enjoy live music, great food and drinks. Each unit has new mini-split systems for heating and cooling. These would be a perfect vacation home or you could live in one and rent out the other. These would also make good airbnb or vrbo properties. The front cottage is approximately 400 sq ft. The back cottage is approximately 750 sq ft. Come check them out!

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