Chestertown MD Real Estate & Homes for Sale

One level living! Two bedrooms, one bath, plenty of storage space, open plan living/dining, outside storage, a porch, patio with a privacy fence to separate the neighboring patio. Backs to trees and private location in the community. There is a basketball court and playground for kids. You own the property - this is not a condo. Beautiful location. Come and see!

The moment you drive down Leeds Court you will be mesmerized by the beautiful mature oaks that line the street! There has only been one owner of this amazing property and it is located in the section of Coventry Farms that does not require a HOA membership or deferred water and sewer charges! Current owners purchased brand new in 2004. Since then they have added many upgrades. A 30'x30' 2 car detached garage/workshop with 12.5'+/- ceiling, equipped with 2 car lifts for the do it yourself mechanic, heated and cooled with large storage area over garage and an in-ground pool were added. Two large sheds were added and the entire rear yard is privacy fenced. A large patio area around the pool is perfect for outdoor entertaining during the warm weather months. There is a hookup for a portable generator and the portable generator is also included! The interior has almost completely been freshly painted with new carpet installed on stairs and in the basement. The kitchen, family room and Florida/sun room provide a large area for indoor entertaining. The owners suite is huge with cathedral ceiling and a private sitting room with walk-in closet and a spacious bath with vaulted ceiling, Jacuzzi tub and separate shower and tiled floors. The basement offers a very large bedroom with its own bath and an exercise room and another room that could act as a home office. Arguably the best location in Coventry Farms!!

Nice home with a large deck overlooking a pretty fenced in back yard, and in good condition. Cozy up to a wood burning fireplace this fall in the comfortable great room located just off the kitchen. There is a formal dining room, living room, powder room on the main level, combining hardwood and carpet. Full unfinished basement for storage, or you could finish that area for even more space! Upstairs is a large primary suite with two large closets, one is a walk in. The en-suite bathroom has a double sink and a shower/bath combined. A separate 2nd floor laundry room is convenient for a four-bedroom home! The layout of the house makes for easy living! Located about a 5-minute drive from Historic Chestertown, which offers such a nice quality of life! There are two grocery stores, a nice health food store, coffee shops, two pharmacies, hardwood stores and beautiful boutique shops to explore. Nestled on the Chester River, you have many opportunities to enjoy sports such as pickle ball, bocci, basketball courts, Chester River Yacht and County Club has a golf course, a pool, a dock bar, and so much more. Restaurants choices are varied, and include deli's, the famous "Blue Bird" with amazing crab cakes. New to Chestertown is a state-of-the-art YMCA with every amenity you could want. Washington College has many activities open to the community, a Lifetime Learning Program, sports, music, are just a few of the offerings. There is a strong artist community with music, many mediums of art, lovely shops, vendors of all kinds at the Saturday Farmer's Market located on High Street. Welcome to a great life in Chestertown!

Welcome to 626 High St, she is just adorable. The hardwood floors throughout this 3 level home have withstood the test of time and are gorgeous! You immediately feel at home! Lovely fixtures, which are probably original to this home add to the charm. The dining room is very generous in size. The main level has an office, powder room, a nice kitchen with an eat in breakfast bar. There are four bedrooms, and 1.5 baths all total. This home has been a rental for a few years, but the owners have maintained it very well. There are just a couple of tweaks to be made, and the owners are working on that as well. The owner has explored the possibility of a possible building lot on the Lynchburg side. There may be a possibility of that with local zoning approval. Nothing is set in stone, but the new owner could explore further, if desired. Only four blocks to the historic district, close to Chestertown's Rail for Trails, with a nice path through Chestertown. Enjoy Washington College and all it has to offer to the community, local restaurants, a thriving artists community, music, the farmer's market, artisans, charming shops, and friendly welcoming people! There is a health food store, coffee shops, two grocery stores, hardware store, a local golf course at Chester River Yacht and County Club, bocci and pickle ball teams you can join! Like to kayak and canoe? You can easily do both on the Chester River, or Radcliffe Creek.

Quiet and peaceful Eastern Shore living. 4 Bedroom 2 Full baths. Wonderful price to get what you want.. Very open floor plan with upgraded kitchen including stainless steel appliances and granite countertops. Lot conveniently located to all the major routes, only minutes away from Downtown Chestertown and Centreville. A short easy commute to Middletown, Dover, Annapolis, DC, and the beaches. Located in QA County school district. Granite, carpet, flooring, siding, and roof color can all be selected by buyer if you hurry in!

Picture perfect, stunning colonial in Chestertown, Maryland! Nestled on a gorgeous, landscaped, corner lot that you will enjoy throughout the year, in the established Coventry Farms Community. Lush, landscaped gardens lead to the stately stone front entry door accentuated with crosshead, pilasters, and pediment, framed by side light surrounds that bathe the 2-story foyer with natural light, welcoming you into this gorgeous, impeccably maintained home. Architectural details of crown moldings, chair rail, wainscotting, turned handrails and hardwood floors are showcased throughout, all further accentuated by the freshly painted, neutral paint palette. The foyer, sided by the formal living and dining rooms, graciously unfolds into the main living area. Prepare gourmet meals in the substantial gourmet kitchen, complete with a suite of stainless appliances including French door refrigerator, custom cabinetry, a pantry, island with breakfast bar, and ample granite covered counter spaces for preparing chef inspired delights. Adjacent to the kitchen is the breakfast room, framed in picture windows, and adorned with a cathedral ceiling, the ideal spot for your morning coffee, and large enough for your next holiday celebration, or host a dinner party in the formal dining room, the options are endless! The family room adjacent to the kitchen displays a floor to ceiling, raised hearth, stone, wood burning fireplace with a handsome stone cut mantle, that makes this sizable room, a very cozy place to gather with the family. The formal living room waits behind French doors, and the perfect powder bath completes this level. Ascend the foyer staircase to the upper-level sleeping quarters, behind double entry doors the primary bedroom boasts a spacious ensuite with a dual vanity, soaking tub, stall shower, and two closets â one is a walk-in, affording plenty of space for any wardrobe. Down the hall are three additional bedrooms and a hall bath. The finished lower level has a massive main living space with a full walk out to the rear yard, a full bath with a stall shower, a finished bonus room which could be a fitness area or media room, and a huge laundry, utility, and storage area. Sliders off the breakfast room lead you to the fenced outdoor living space, offering multiple zones to entertain and play while enjoying the outdoors. The brick paver patio hosts a beautiful pergola covered lounge space, and plenty of room for the kids and furry family members to play safely. The community of Coventry Farms is just minutes from shopping and local favorite dining spots, and just a short drive to Historic Chestertown Maryland along the banks of the Chester River. The cobblestone streets of Chestertown offer abundant unique boutiques, dining, galleries & studios, lodging, and historical & cultural sites like Washington College, the first chartered college in the United States of America. Come see 218 Camelot today, this extraordinary residence could be your ideal forever home â Simply Perfect!

SFH with 2 bedrooms, 1 bath, one level living situated on .40 acres of land, Living/Dining room combo, Table pace kitchen, Den off living room, screened porch off back, the home has room for improvements or expansion

A $100,000 decorator allowance offered toward updating and redecorating. Never before on the market, Windswept is a remarkable property with views that celebrate the water. Built by the owners. Private dock with 5 deep water slips. 5-6ft MLW (buyer to verify). Large deck with gazebo to enjoy the boats going by. Geothermal heat and AC. 2 stone wood burning fireplaces. A breathtaking view from almost every room of the house! Lots of space in this sprawling home. Primary bedroom has a large sitting room attached with 2 walk in closets. An additional bedroom also on the main floor. The second floor has a nice family room which is open to the living room below with its own tanning deck. 2 bedrooms with a Jack and Jill bath also on the second floor. An additional small room could be used as an office or just additional storage. Some updating needed but in overall wonderful condition. Nice landscaping. No flood insurance needed. High speed internet available. Voluntary civic association is $100 per year. $350 per year for road maintenance. An easy stroll to Great Oak Marina and golf course.

Buying a new home in historic Chestertown continues to be the best option on the Eastern Shore for those looking to retire or start a new family surrounded by the tranquility of upper shore living. This is a unique opportunity to buy an affordable, yet brand new home located centrally in town a short walking distance to local stores, restaurants and the new YMCA. Your new home is a short drive from Washington College and Chestertown's historic waterfront district. This NEW CONSTRUCTION two story 3 BR duplex style townhome is complete and ready to move-in with no HOA fees or regulations. This end unit home has a private front, back and side yard with off street driveway. Inside, a modern open concept floor plan, upgraded stainless steel appliances, granite countertops and bright white cabinetry are a welcome invitation to comfortable living. There are multiple linen and storage closets to keep your living area organized. All living areas have easy to clean and maintain durable vinyl plank flooring. This townhome has 3 generous bedrooms and 1 full bathrooms upstairs and a 1/2 bathroom on the main floor. All bathrooms have matching granite countertops in modern design which coordinate with the main living area. This private lot offers a back porch with oversized private storage closet.

3 bedroom/2 bath rancher with a 2 car garage, front porch and full basement located on Tamarack Road which is not a thru road meaning not much traffic. Home offers a large eat-in kitchen with a fireplace and a six foot sliding glass door that accesses the spacious rear deck. The rear deck is quite private with the back yard being bordered with a wooded area inviting the pleasure of bird watching. The family room also has a fireplace.. The full basement could be finished off for additional living space. Home is located only a few minutes from Historic Chestertown and convenient to waterways for boating, fishing and water sports. Roof is one year old.

Investor Alert! Property being Sold in "AS IS Condition" Clean out is buyers responsibility. Offers on this property require $5,000 Earnest. Money Deposit. Renovation loan, Hard Money or Cash Offers.

Early Victorian in Chestertown that is simply oozing with charm. Lots of attention to detail. Private garden in the back. Lovely screened in porch on the side. Family room off the kitchen with brick flooring. 2 staircases. 2 separate attic spaces each with stairs. One is climate controlled. Approximately 1 block from the heart of downtown. 2 bedrooms and 1 full bath upstairs. A half bath on the main floor. A shared driveway on the side of the house gives you access to park behind the house. Fix a gourmet meal while your guests are on the patio.

Instant investment opportunity! Tenants have been given notice to vacate, but would like to stay. Less than one year old duplex within walking distance to the new YMCA. One level living with an open floorpan, 3 large bedrooms, and 2 full baths. The open concept kitchen features stainless steel appliance and granite countertops, with direct access to a private patio with an oversized storage closet. The three bedrooms have ample closet space, and the primary bedroom includes an en suite bathroom. Tenant occupied and requires 24 hour notice for showings.

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants.

This Colonial has had a kitchen update 4+/- years ago with granite counters, breakfast bar and a propane gas stove and lots of cabinets. The main floor bath was updated 3+/- years ago with handicap toilet and walk-in shower. Having a main floor bedroom is a huge plus! Most of the main level has bamboo flooring installed. There are 3 additional bedrooms on the second floor, two of which are quite large. The interior has been freshly repainted. All screens have been replaced. A rear deck a with ramp and patio overlook a fenced backyard and there is outdoor lighting! There is even electric hookup for your motor home. Add the fact that Chesapeake Landing has community water access, then what else could you ask for?

Only a few minutes drive to Deep Landing boat ramp on the Chester River, this lovely location nestled among the trees provides a wonderful backdrop for your new home. Sitting on a block foundation and strapped to piers, this just finished total renovation contains great room sizes & a floor plan that is smart and functional. A blank palette just waiting for you to personalize and make it absolutely charming!

Back on the market due to a buyer financing problem. Move in ready home! On the main level, there are formal living and dining rooms and a kitchen that is adjacent to a beautiful breakfast room. You will enjoy lots of light streaming into the first floor. The kitchen has loads of storage with pantry and lots of upper and lower cabinets. The dining room offers a tray ceiling, and plenty of room for your dining room furniture. Upper level boasts of 4 large bedrooms and two full size bathrooms. The backyard has a freshly painted fence, and lots of room for your furry friends. The house has freshly painted exteriors and is nicely landscaped. The basement is large and a clean slate, that you can certainly finish. The two car garage has lots of space for storage. The home overlooks the main park and is centrally located.

Affordable investment opportunity in Downtown Chestertown! Great layout with large room sizes, hardwood floors, private backyard and off street parking via rear alleyway. Home may need some updates, but still very habitable. May not qualify for all loan types, cash or conventional financing will work. Walking distance of everything going on in Downtown, come check it out!

Conveniently located within walking distance to downtown Chestertown and the water. Tenant in place - need 24 hour notice to show.

Buying a new home in historic Chestertown continues to be the best option on the Eastern Shore for those looking to retire or start a new family surrounded by the tranquility of upper shore living. This is a unique opportunity to buy an affordable, yet brand new home located centrally in town a short walking distance to local stores, restaurants and the new YMCA. Your new home is a short drive from Washington College and Chestertown's historic waterfront district. This NEW CONSTRUCTION single story 3 BR duplex style townhome is complete and ready to move-in with no HOA fees or regulations. This end unit home has a private front, back and side yard with off street driveway. Inside, a modern open concept floor plan, upgraded stainless steel appliances, granite countertops and bright white cabinetry are a welcome invitation to comfortable living. There is a separate laundry room and multiple linen and storage closets to keep your living area organized. All living areas have easy to clean and maintain durable vinyl plank flooring. This single story townhome has 3 generous bedrooms and 2 full bathrooms including a master bath. Both bathrooms have matching granite countertops in modern design which coordinate with the main living area. This private end lot offers a back porch with oversized private storage closet.

Water, water everywhere! This incredibly unique property is situated on a sheltered deep-water creek offering a westerly, southwesterly exposure with uncompromised sunsets. Fairlee Creek offers one of the most convenient boating accesses on the upper Chesapeake Bay. This 1.9 acre property comes improved with 2 homes, a deep water dock with 5-6' depth, an outdoor barbeque patio overlooking the creek, and 575+/- feet of secure shoreline. One of the two homes on this spectacular property is conte-levered above the water offering the feeling of being on a yacht with panoramic views from every room. The second home is a three bedroom, comfortable, one floor rambler with lovely screen porch overlooking the creek. The location of this property is notable in that it is centrally located in unspoiled Kent County and convenient to both historic Chestertown and the bayfront town of Rock Hall. Great Oak Marina and Resort is a short stroll of golf cart ride away where the residents of Great Oak Estates may share in the use of the establishment's facilities including the pool, restaurant, beach, and 9-hole golf course. Great Oak Estates is a fun-filled neighborhood where the residents interact well together and the spirits are active in the summertime and peaceful in the wintertime!

Don't want the hassle of going up & down stairs but still want house space? This is not your ordinary rancher - it's oversized 30ft wide with over 2700sqft of living space and there's no other like it in the sought after Coventry Farms. This home is one of the larger lots from the original building development sitting on just over a half acre. Hardwood floors & 9ft ceilings. New roof in 2019. Energy efficient 22-seer dual-stage hybrid-heat pump HVAC system. Never run out of hot water with the Navian tankless hot water heater. Always wash with clean water from the whole-house water filtration system. Always drink clean water from the reverse osmosis system at the kitchen sink. Oversized 2 car garage, 25x30 with 12 ft ceilings that can fit a car lift. Lofts for extra storage space. Attic can be used as storage OR can be finished to add another 1,000+ of living space. Living space includes a Great Room with lots of natural light. Kitchen includes stainless steel appliances. Master bedroom with large walk-in closet. Sunroom & back deck lead out to a wide open backyard. Low maintenance landscaping. No HOA. Only minutes to downtown Chestertown, restaurants, shopping and marinas. Room Measurements Garage 25'x30' ceiling 11' Kitchen 17'x 15' Dining room 13'x15' Living room 17'x 19' Front sitting room 13'x15' Master bedroom 17'x15' Bedroom 2 13'x11' Bedroom 3 13'x11' Sunroom 16'x17'

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.