Welcome to 23530 Clarissa Road! This well maintained home is established on a beautifully situated lot located within the water access community of Chesapeake Landing. You'll be greeted here by vibrant greens, found flourishing through mature surrounding woods and meticulously cared for landscaping. Find your seat and enjoy peace in nature as an abundance of wildlife can be heard and seen throughout. An asphalt driveway will provide smooth sailing as you come and go. The completely fenced in back yard offers peace of mind as you can allow pets and/or children to play freely. A 16' x 10' shed with electric and additional rear lean-to provides adequate storage for those off season items and e
Welcome to 7488 Poplar Ave in the heart of Chestertown. This charming 3-bedroom, 2-bath rancher nestled in a serene setting, backing onto scenic woods. Built in 2019, this modern home offers a perfect blend of comfort and style. As you step inside, you'll be greeted by a spacious open floor plan illuminated by natural light. The living area features luxurious LVP (Luxury Vinyl Plank) flooring, creating a warm and inviting atmosphere throughout. The kitchen boasts sleek countertops, stainless steel appliances, and ample cabinet space, making it ideal for both everyday cooking and entertaining. The primary bedroom is a peaceful retreat with an en-suite bathroom, offering privacy and convenien
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, f
This Welcoming Ranch-Style Home in Chestertown, MD—Steps from Rosin Creek—is located on the Queen Anne's County side of Chestertown, Maryland. It offers spacious living with practical updates and a warm ambiance. Less than a block from Rosin Creek, the home features large bedrooms, a large basement, and a substantial attached 2-car garage. Recent updates include a new roof, an environmentally friendly nitrogen-reducing septic system, and an updated air handler, ensuring the home remains comfortable and efficient. The house's hardwood floors add a classic touch, while practical spaces like a separate laundry room and an eat-in kitchen enhance everyday living. The screened porch p
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, is the living room, dining room, kitchen, den/office, half bath, all- season sun room, and inside stairs to the full basement, The new custom kitc
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
Extraordinary opportunity to purchase the estate of Clorea Truslow—the cherished namesake of Truslow Rd. For generations, this land has been held dear by the Truslow family, and now, for the first time, it is being offered for sale, presenting a once-in-a-lifetime chance to make it your own. Nestled just across the river from the vibrant events of the Sulatana, Downrigging, Tea Party festivals, and more, you'll enjoy front-row seats to the action from the comfort of your own home. Embrace the charm of yesteryears while immersing yourself in the excitement of contemporary festivities. This timeless home beckons with a flowing floor plan, tall ceilings, and gleaming hardwood floors, off
MOVE IN READY !!! Charming 3/1 ranch home nestled in a water-oriented community of Chester Harbor. Perfect for those who love being close to the Bay and all it has to offer. This recently updated property boasts modern amenities and a cozy atmosphere, offering the ideal blend of comfort and convenience. Embrace the coastal lifestyle with opportunities for boating, fishing, and waterfront dining and shops that are just moments away. Queen Annes County Schools district. Boasting recent updates throughout, this charming residence offers a perfect blend of modern convenience and peaceful surroundings. (see a list of improvements in the documents section) Outside, the property
COMING SOON! 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, fresh paint, floors refinished and more. Details & additional photos coming soon! Walk to conveniences from this move-in ready charmer in upper Chestertown.
Welcome to a captivating opportunity to reside in the idyllic neighborhood of The Grove in picturesque Queen Anne's County. Prepare to be enchanted by this charming abode, where every detail exudes warmth and comfort. Step inside and be greeted by the timeless elegance of hardwood floors and plush carpeting, inviting you to kick off your shoes and make yourself at home. The heart of the main floor boasts a cozy gas fireplace, creating a cozy ambiance perfect for intimate gatherings or quiet evenings curled up with a good book. With four bedrooms and 2.5 baths, there's ample space for your family to spread out and relax. The open floor plan seamlessly connects the living spaces, allowing for
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 commu
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 commu
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 f
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.
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 commu
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 commu
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.
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
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!
Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike. Situated on a generous lot, steeped in the rich history of Chestertown and prominently featured on historic maps as the Laurence Lots, this property offers a canvas brimming with potential. Whether you envision revitalizing it into a majestic single-family residence or retaining its current configuration with a townhouse on one sid
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. .
* * SELLER WILL CONSIDER PAYING BUYER CLOSING COSTS WITH ACCEPTABLE OFFER * * Manufactured Rancher on 1 acre of flat land with wooded lot. New Covering for the front porch and deck porch on rear. Open living room/kitchen combination. Full sized washer/dryer on property. 3 bedroom and 2 full baths. Recently installed water heater, appliances (propane) stove and refrigirator, heating panels. The property is back on the market shortly as we finished a few more items. ASK about the special financing!! It is available through a local lender for these types of properties.
A stately 1800’s 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 i
A stately 1800’s 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 i
A stately 1800’s 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 i
A stately 1800’s 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 i
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
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 *
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 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
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 m
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 t
NEW PICTURES and 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 throu
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 propertie
Prime Location Alert! Nestled along one of Chestertown's bustling thoroughfares, this delightful 3-bedroom, 1-bathroom bungalow exudes charm and possibility. Boasting a coveted Intense Village zoning, this property opens doors to a myriad of opportunities, whether for residential bliss or a variety of commercial endeavors. Step inside to find a generous family room seamlessly connected to the galley kitchen, offering a cozy yet functional layout. Relax and unwind in the screened-in porch or take advantage of the detached 2-car garage, complete with abundant off-street parking. Recent upgrades add to the allure, including a new heat pump with central air in 2021, a fresh roof installment 202
BRING ALL OFFERS! Welcome to this newly renovated home with stunning upgrades throughout! This charming, easy-living home, in Chestertown, MD has all new LVP flooring, paint and drywall, a brand-new kitchen featuring sleek grey cabinets, stainless steel appliances, a deep sink, backsplash, and quarts countertops. The bathroom boasts a beautifully tiled shower. New washer and dryer on the main floor, and beautiful windows to let in an abundance of natural light. Enjoy almost an acre of land with plenty of room to enjoy the quiet outdoors. This home is located in Queen Anne’s County, close to rt 301, making for a short commute 25 minutes to Middletown, DE, 35 minutes to the Chesapeake
SMITH-RINGGOLD HOUSE.ca. 1750 This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of Historic Districtnof Chestertown on Maryland's Eastern Shore. Originally a merchant’s home , the Smith-Ringgold house has been tastefully modified representing four defined periods and enlarged over the course of its 250-year history. William Ringgold added rooms toward the River in about 1759 that doubled the space. (Often, one would find 18th c. additions such as this creating a telescope style design. ) The present owner took two-years to restore the home from foundation to attic. A river-side sun-porch/breakfact room was added. ,T
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 commu
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,
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 Cheste