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Chestertown MD Real Estate & Homes for Sale30 Properties Found
The median home value in Chestertown, MD is $269,990.
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 $269,990.
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!
1–25 of 30 properties displayed
Courtesy: Chesapeake Real Estate Associates, LLC
View additional infoWelcome 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. Seller is offering 4k towards buyers closing costs for choice of carpet / paint.
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional infoThis 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.
Courtesy: Village Real Estate Company LLC
View additional infoWonderful 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!
Courtesy: Gunther-McClary Real Estate
View additional infoA 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.
Courtesy: Gunther-McClary Real Estate
View additional infoA 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.
Courtesy: Gunther-McClary Real Estate
View additional infoA 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.
Courtesy: Gunther-McClary Real Estate
View additional infoA 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.
Courtesy: Gunther-McClary Real Estate
View additional infoBeautifully 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..
Courtesy: TTR Sotheby's International Realty, (410) 673-3344
View additional infoEvery 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.
Courtesy: Cross Street Realtors LLC, 4434803453
View additional infoNew 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*
Courtesy: Doug Ashley Realtors, LLC
View additional infoStep 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.
Courtesy: Taylor Properties
View additional infoWow - Major Price Change - Hurry! Enjoy over 3 acres to play, hunt, ride 4 wheelers, have horses, chickens & more. Owner has wonderfully updated almost everything about this house and there is home warranty for peace of mind. Relax in the morning on the front porch and watch nature from every window. Gorgeous spacious kitchen with granite counters and including an eat in one that will seat at least four. All brand new appliances convey including washer and dryer. Cozy up by the wood burning fireplace or explore your little piece of heaven. This property used to be 2 lots and county says its zoned for several lots that can be potentially taken off. Explore the possibilities. Shown by Appointment only.
Courtesy: RE/MAX Executive, (443) 274-1900
View additional infoPrice Reduced $20k!!! Buyers got cold feet! Their loss is your win! Discovery your sanctuary on this 6 plus acre property, nestled on the outskirts of Chestertown. The property houses an abundance of wildlife such as deer, turkey, fox, and ducks! You might even find a beaver swimming up the creek. Thoughtfully updated, you wonât want to miss this a little over 1600 sq ft 3 bedroom 3 bath home, which includes two en-suites. A 420 sq. ft addition was completed in 2023, which boasts white oak flooring, high end bathroom finishes and a tranquil master bedroom. Additionally, you will find a brand-new kitchen where modern elegance meets farmhouse charm. Adorned with shiplap accents, a farmhouse sink, and stunning two-tone cabinets, this culinary haven is as stylish as it is functional, including new stainless steel appliances. It doesnât stop there, the remainder of the home includes refinished hardwood floors, new tile throughout the kitchen and hall bathroom, all new baseboard, window and door trim, updated light fixtures as well as finishes. In 2022, the exterior received a complete makeover with a new deck, sheathing, vinyl siding, upgraded soffits, and exterior doors, while brand new Jeld Wen windows adorned with sleek black trim enhance both style and functionality. New insulation was added to the attic to create an efficient home. Utilize the unfinished basement (1200 sq ft), located within the footprint of the original home, for plenty of storage space to accommodate your belongings and keep your living areas clutter-free. Stay connected to the world with access to two fiber internet services, ThinkBig and Talkie. Whether you're working from home or streaming your favorite shows, lightning-fast connectivity is always at your fingertips. Centrally located, this property is just 42 miles to Dover, Delaware, and 53 miles to Annapolis, Maryland. For boat enthusiasts, it's a mere 4 miles to Jellyfish Joel's or Tolchester Beach, and less than 10 miles to Rock Hall, providing easy access to some of the area's most popular waterfront destinations.
Courtesy: Berkshire Hathaway Homeservice Homesale Realty, (800) 383-3535
View additional infoPrice Reductions!!! This deal just got a good bit sweeter...Escape to the Country! This home is perfect for the outdoor enthusiast. Bring the horses, dogs, chickens, hunters, hobbyist,...you name it. 15 acres, with small pond and open areas for your animals, sports field, fire pit or huge gardens. Chicken coop, air rifle only shooting range, basketball court, wooded acreage with walking or biking trail and hunting possible all part of what makes this place a dream come true. In the home enjoy large family room with propane fireplace, beautiful kitchen with stainless steel appliances and granite counters. Custom cabinets and built-ins, wood, laminate, and tile floors throughout. Entry level and second level bedrooms. Ready to relax head to the screened porch for quiet evenings. Hot tub hookup in place. Shed and outbuilding provide endless hobby, farm, or craft options. The 30 x 36 metal building has a large open space with multiple smaller rooms with electric and heat. Working at home? Talkie WiFi is available. RV hook-up at both the house and the outbuilding. Underground dog fence and 2 collars will stay . Metal building is in good shape but being sold âas isâ. Abandoned underground oil tank on site. This type of property does not often come to market. DONT MISS IT! Home is on a shared R-O-W. No drive-bys. Pets on site so please provide as much notice for showings as possible.
Courtesy: Blackwell Real Estate, LLC, (443) 221-4120
View additional infoWell 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!
Courtesy: Taylor Properties
View additional infoNEW PICTURES! 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.
Courtesy: Chesapeake Real Estate Associates, LLC
View additional infoWelcome 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.
Courtesy: The Hogans Agency, (410) 778-1665
View additional infoBe sure to check out the photos - this home has real charm and character! This well-maintained house has been home to the same family since 1975: blacktopped driveway resealed in 2022, new roof 2017, new well 2016, quarterly Pest Service and mature landscaping with a fenced backyard. New washer and dryer and a full tank of propane for use of the attractive oak fireplace. Both bathrooms completely updated 2024. Both large upstairs bedrooms have double windows which allow for maximum light during the day. The property sits on four lots for a total of .69 acres. The quiet community of Chester Harbor has a voluntary HOA which allows for Chester River water access and use of the community area located at the end of Fairview Drive. Round Top Park is close by - ball courts, playground and a pavilion. Close to historic Chestertown and just 45 minutes to Middletown and tax-free shopping!
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional infoPrice 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!
Courtesy: Cross Street Realtors LLC, 4434803453
View additional infoPrime 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 2022, and plush new carpetingâeach enhancing both comfort and aesthetics. Location-wise, convenience reigns supreme, with proximity to Chestertown's treasures such as Washington College, the hospital, local boutiques, the newest marina, eclectic dining options, and much moreâall just a stone's throw away, promising a lifestyle of ease and accessibility. Overflowing with potential, this property beckons for visionaries and dreamers alike. Please take note, there's an existing lease in place, expiring on December 31, 2024. Don't miss out on this golden opportunity!
Courtesy: Cross Street Realtors LLC, 4434803453
View additional infoThis former horse barn was converted in 1990 into a well-crafted personal residence. In early 2018, the current stewards retained acclaimed contractors Taylor Loughry to apply their craftsmanship to a large portion of the house. The most delightfully unique characteristic of this 4-5 bedroom, 3 and 1/2 bath home with attached two car garage is its' private, landscaped lot accessed by a gravel driveway on North Water Street. A pair of new wood gates define the entry to the oasis. The redesigned flow of the first floor provides well for the intended purpose of both entertaining and home comfort. A den, powder room, and elevator adjoin the two-story, sun-filled foyer. A large living room with gas fireplace and separate dining room (with doors to the rear brick patio and raised beds) provide the pathway to a beautifully designed large island kitchen with breakfast area with bay window. Mudroom with sink, full sized washer and dryer and storage is adjacent to a side entry and double garage with EV charging station. Floor two comprises mostly a primary suite that includes bath, large office and exercise space with access to a very large, insulated and conditioned storage space (easily repurposed to a games room or home theatre), a guest bedroom and hall bath. The third-floor features two additional bedrooms and bath with large amounts of closet space. Recently installed solar panels, discreetly positioned, have resulted in nearly net zero energy expense.
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional infoBRING 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 Anneâs County, close to rt 301, making for a short commute 25 minutes to Middletown, DE, 35 minutes to the Chesapeake Bay Bridge, and lots of local amenities near by. $1,725,000201 N Water Street Chestertown, MD 21620
Courtesy: Maryland Heritage Properties, (443) 480-7342
View additional infoSMITH-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 merchantâs 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. ,The cedar shingle roof, , plumbing, wiring, heat and A/C systems were added or replaced. Wood floors throughout the house have been beautifully restored. Modern storm windows are energy efficient and all but eliminate street sounds. Aside from your own personal touches, this house awaits our arrival anf iss prepared for the next century. The ground floor has a large double parlor, serene sitting room, formal dining room, breakfast room, and a stunning Chefâs kitchen. An important feature is the hand painted dining room mural by noted artist Jack Schroeder. The front hall, redesigned in about 1860, replaced a steep stairway with a grand and gracefully curving staircase. The second floor contains three large en-suite bedrooms and a laundry room that is also accessible from the kitchen via a âsecretâ staff stairway. The third floor has a large sitting room, bathroom, and fourth bedroom. A setion of the homeâs original c. 1750 roof has been restored forming a unique design element. The backyard was extensively terraced, probably in the late 1700s, in descending levels down to the Chester River eliminating the fear of flooding. The free-standing brick garage dates from the early 20th century, when car garages replaced horse barns. This structure could easily be repurposed as an artistâs studio or home workshop. A wide driveway area provides additional off-street parking. Truly an inviting residence for intimate family evenings or grand parties. Perfect setting for one's collection of antiques or for the simplicity of contemporary furniture which emphasizes the wonderful architecture. CHESTERTOWN IN THE COUNTY OF KENT Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities. Chestertown is home to a surprisingly large number of elegant, historical Georgian homes as well as Victorian âpainted ladies.â With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City. Chestertown in the County of Kent is "a place where one would rather be". Centrally located Washington College (founded in 1782 with the personal support of George Washington) provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers. The town boasts a weekly Farmers Market, excellent coffee bars, restaurants, and art galleriesâbut no big box stores. The Chester River Yacht & Country Club offers an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party, commemorating a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. Today, Chestertown, is a vibrant mix of old families, newcomers, college students, full time residents with children, and involved weekenders. Open House: Saturday, 5/4 11:00-2:00PM
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional infoWelcome 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! Open House: Saturday, 5/4 11:00-2:00PM
Courtesy: Benson & Mangold, LLC, (410) 822-6665
View additional infoIntroducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester River Landing. Hands down, one of the best lots in the community! The Schooner model is an exquisite three-bedroom, three-and-a-half-bath home that offers luxurious living and breathtaking, panoramic views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!
1–25 of 30 properties displayed
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