Chestertown MD Real Estate & Homes for Sale

Welcome to your Eastern Shore haven! This charming property boasts recent updates and in a prime location, offering the perfect blend of modern comfort and public water access to Fairlee Creek & the Chesapeake Bay!Enjoy the 6ft privacy fence that enhances the privacy and security, allowing a safe haven for pets and family or easily store your boat with the double gate entrance. Enjoy the convenience of stainless steel appliances, all updated around 2020! Year-Round Comfort with central HVAC, furnace, and heat pump that were upgraded in 2021, ensuring optimal comfort in every season. A new roof and plywood were installed in 2022, providing durability and peace of mind for years to come. A new sump pump was added in 2022, offering enhanced protection against water damage. Step into style with a new storm door installed in 2023, adding both aesthetic appeal and practical functionality all while going hand in had with new garage doors and openers, all installed in 2024! Upgraded bathrooms and a renovated kitchen make this home truly move-in ready, allowing you to start living your Eastern Shore dream immediately. Whether you're seeking a permanent residence or a weekend getaway, this property offers a tranquil retreat from the hustle and bustle of city life.

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, offering a canvas for your imagination to flourish. With spacious rooms, ample storage, and an elevator, convenience meets elegance at every turn. Breathtaking views serve as a backdrop to daily life, with 3 out of 4 bedrooms offering sprawling views of the river's beauty.While the home may require some tender loving care, its inherent value shines through, promising a rewarding renovation journey. Imagine waking up to the gentle lapping waves and retiring to the rooftop deck or screened in porch, a tranquil oasis awaiting restoration. The dock, though in need of replacement, boasts ample water depth, inviting you to dock your boat and enjoy at your leisure.Don't miss the chance to make this piece of history your own. Schedule a showing today and experience the allure of this timeless home firsthand. It's an opportunity not to be missed. Sold "as is."

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.

Chestertown Rancher in Country Club Estates! This rancher overlooks the golf course with distant water views. Amenities include fireplace, 2 car detached garage, storage building, wood floors, dining room, circular driveway, and laundry room. This is a Fannie Mae Homepath property. Submit all offers on Homepath site. Downtown Chestertown with restaurants and shops is a short drive away.

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 showcases a lovely outdoor area, perfect for enjoying the picturesque surroundings and the beauty of the community. Whether you're relaxing in the back yard with a morning cup of coffee or hosting a barbecue with friends, this home offers a wonderful setting for creating lasting memories. Don't miss your chance to own this updated ranch home in a prime location, offering the perfect combination of modern comfort and a peaceful waterfront setting. Come experience the beauty and tranquility of this unique property - your new oasis awaits!"

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!

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!

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.

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!

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!

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.

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 $980Unit 2 is 2 stories and 2 bedrooms with a washer/dryer. Rent $1850Unit 3 is a 1 bedroom with a turret. Rent $1300Unit 4 is a 1 bedroom with a turret. Rent $1200Last year's electric: $4331Last year's oil: $3215

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 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.

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 side and two apartments on the other, the possibilities are boundless.While the property stands as a testament to enduring charm and character, it's essential to note that significant settling has occurred over the years. As such, unlocking its full potential will necessitate considerable renovation efforts. This property is a bona fide fixer-upper and is exclusively offered in its current "as is" condition, awaiting the transformative touch of its next custodian.With its prime location , this property represents not only an investment opportunity but a chance to become part of Chestertown's storied legacy. Seize the chance to breathe new life into this home and craft a future brimming with possibility. Embrace the challenge, unleash your creativity, and make your mark on Chestertown's captivating tapestry of history and culture. Schedule your viewing today and prepare to embark on an unforgettable journey of restoration and renewal!

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!

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 $980Unit 2 is 2 stories and 2 bedrooms with a washer/dryer. Rent $1850Unit 3 is a 1 bedroom with a turret. Rent $1300Unit 4 is a 1 bedroom with a turret. Rent $1200Last year's electric: $4331Last year's oil: $3215

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 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 Maryland's 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.

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 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 Maryland's 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.

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 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 Maryland's 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.

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 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 Maryland's 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.

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..

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*

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.

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 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.