Chestertown MD Real Estate & Homes for Sale

A unique opportunity! This charming brick building was originally built in the 1800s as a chapel named Mowbray Chapel, eventually abandoned and then the interior was completely rebuilt in 2021 with electric, utilities, a new well and septic. A SIMPLY STUNNING light filled space that has been used as a residence and entertaining venue. Completed with the highest quality of materials and a brand new kitchen, full bath room and laundry room as well as a gas wood stove yet blended with the large windows, gorgeous brick walls, high ceilings and substantial woodwork. A true blend of old world elegance and modern amenities. Nestled among the mature trees on a 3+ acre property, there is also good outdoor space with a lawn, woods and a pond combined to offer spectacular outdoor areas year round.

Lovely like new all one floor home on extra large level lot with massive rear yard including mature trees and landscaping. Quality finishes throughout include wonderful kitchen with granite countertops, eng hardwood floors, and central air! ABSOLUTE MUST SEE HOME!

Come by this lovely BRAND NEW home in Chestertown. This home features Luxury Vinyl Flooring throughout, White Cabinets, Granite Counters, Spacious Living Room, Eat in Kitchen area, covered patio off the kitchen, spacious bedrooms including a large primary bedroom suite and much more! Only 2 more of these new homes are available, so come by today and take advantage of this opportunity while it lasts. Special financing programs available, including Zero Down payment loans and closing costs assistance programs so you can own this home for less than renting. Please note: the exterior of the home is white

Spectacular sunsets guaranteed with panoramic views of the Chesapeake Bay. Eastern shore waterfront home features gourmet kitchen , outdoor pergola, updated bedrooms and baths, waterside deck , new roofing, outdoor waterfront porch, wet bar, and multiple zones for heating and cooling. Close proximity to Philadelphia and Baltimore/DC metro area make it a perfect weekend get away. Enjoy scenic Chestertown and the quaint town of Rock Hall and the bounties they have to offer. Abundant marinas and restaurants are near by . Relax with your morning cup of coffee watching the cargo ships ply the bay in the comfort of your sunroom. Take a tour of the local art galleries, shops and taste the bays bounty at local culinary establishments. This secluded home offers peace and serenity. Call today to schedule a viewing.

Don't miss your chance to own a piece of Chestertown history! This immaculately restored historic home in downtown Chestertown is only blocks away from the charming shops, fine dining, and gorgeous views of the Chester River. Enjoy spending Saturday mornings at the Farmerâs Market or catch a game at Washington College, which is also a quick walk away. The first level of the home has an open floorplan with tons of natural light. Gorgeous kitchen with brand new stainless steel appliances, marble countertops, and tile backsplash. A beautifully remodeled half bath is perfect for guests. There is also a spacious first floor primary bedroom with full bathroom and walk-in closet. The functionally attractive barn door allows this room to also serve as an additional family/living room. The large rear deck has been completely redone and would make the perfect spot to sip your morning coffee and watch the birds and squirrels, and then to drink your favorite beverage while grilling up dinner looking out at your private backyard. Upstairs are two large bedrooms with brand new wall-to-wall carpet and roomy walk-in closets (a rarity in historic homes). The hall bathroom has an oversized vanity and stylish shiplap and shower with tub. Outside, the original wood siding and windows have been fully restored and help to maintain the homes elegant charm and authenticity. Walking up the front steps you will notice the brick walkway with newly completed landscaping. There is also an unfinished basement for additional storage. This home is a showstopper that you wonât want to miss!

Quality new construction that is very close to completion located in Chester Harbor. Wood floors throughout the living room, kitchen, dining area and mud room. Open floor plan provides cathedral ceiling and a vent-less gas log fireplace. 2" x 6" exterior wall construction with foam insulation. Kitchen offers Corian style counter tops, refrigerator, stove, dishwasher and microwave. Separate laundry room has wash tub and built in shelving. Heat pump supplies heating and cooling. Fire suppression system. Front porch and small rear deck. BAT septic system. 22' x 20' insulated attached garage. Conditioned crawl space. Short distance to Chester Harbor community park and Rosin Creek water access. Minutes to Historic Chestertown. MHBR #1578

Welcome to Fairgale, a tasteful waterfront community located minutes from Historic Chestertown and Rock Hall. This 36.66 total acre property with 1250+/- feet of stable shoreline and 21+/- fertile tillable acres is ideally elevated and positioned to take advantage of the panoramic water views and sunsets across Fairlee Creek. The thoughtfully designed residence has the perfect balance to host both casual or formal gatherings, either indoors or outdoors. The exterior of the residence includes a wonderful slate patio, brick sidewalks, beautiful gunite swimming pool, storage building for small watercraft and lawn equipment, and a winding asphalt driveway. The interior includes a chefs eat-in kitchen with cozy gathering area, a formal living room with double patio doors, a formal dining room, an office, and a private first floor primary bedroom suite with two spacious walk-in closets and a large walk-in shower. Upstairs, you will find three additional bedrooms with two spacious full ceramic tiled baths. The finished basement is a grandchild's dream with a marvelous game room area, built-in bunk beds, separate bedroom, full bath and separate outside entrance. Other notable interior features include beautiful wood floors (Oak and Heart Pine), designer tile in bathrooms and laundry room, a gourmet kitchen featuring professional grade appliances, expansive butcher block center island, granite counters, and exposed ceiling beams. A large sliding glass door opens onto the lovely, screened porch overlooking the pool and patio. This home is loaded with numerous other tasteful finishes and features for which you must see to appreciate. Water access is available from the gently sloping lawn to the water's edge or also a short golf cart ride away from the community waterfront area where you will find the property's own deep water boat slip with new 5-ton electric boat lift and community boat ramp. This property offers the epitome of true Eastern Shore living, with timeless style and endless possibilities!

Welcome to Fairgale, a tasteful waterfront community located minutes from Historic Chestertown and Rock Hall. This 36.66 total acre property with 1250+/- feet of stable shoreline and 21+/- fertile tillable acres is ideally elevated and positioned to take advantage of the panoramic water views and sunsets across Fairlee Creek. The thoughtfully designed residence has the perfect balance to host both casual or formal gatherings, either indoors or outdoors. The exterior of the residence includes a wonderful slate patio, brick sidewalks, beautiful gunite swimming pool, storage building for small watercraft and lawn equipment, and a winding asphalt driveway. The interior includes a chefs eat-in kitchen with cozy gathering area, a formal living room with double patio doors, a formal dining room, an office, and a private first floor primary bedroom suite with two spacious walk-in closets and a large walk-in shower. Upstairs, you will find three additional bedrooms with two spacious full ceramic tiled baths. The finished basement is a grandchild's dream with a marvelous game room area, built-in bunk beds, separate bedroom, full bath and separate outside entrance. Other notable interior features include beautiful wood floors (Oak and Heart Pine), designer tile in bathrooms and laundry room, a gourmet kitchen featuring professional grade appliances, expansive butcher block center island, granite counters, and exposed ceiling beams. A large sliding glass door opens onto the lovely, screened porch overlooking the pool and patio. This home is loaded with numerous other tasteful finishes and features for which you must see to appreciate. Water access is available from the gently sloping lawn to the water's edge or also a short golf cart ride away from the community waterfront area where you will find the property's own deep water boat slip with new 5-ton electric boat lift and community boat ramp. This property offers the epitome of true Eastern Shore living, with timeless style and endless possibilities!

This listing offers the unique opportunity to own two waterfront parcels, one improved by a beautiful 3-4 bedroom cape, and an adjacent perc approved lot all located less than a mile from Chestertown. The addresses are 121 Lyons Ln. which is 1.9 acres, 118 Lyons Ln. which is 1.2 acres and 117 Lyons Ln. which is .44 for a total of 3.5 acres. They are being sold together and the tax information is for all three lots. The cape is on the 1.9 acre wooded lot and features premium materials and finishes. There are yellow pine floors reclaimed from Camden Yards, crown moulding, wainscoting, panel doors, fireplace, sun room and a master bedroom on the first floor. The second floor has two bedroom and a third room which could be a bedroom, office or 2nd floor family room. The second floor bathroom is huge and has just been remodeled. There is also a separate studio or home office, also recently remodeled, in the rear yard with AC/Heat. A Williamsburg inspired garden surrounds the studio and the rear yard is partially fenced. The waterfront is a quiet creek right across the Chester River from the historic district. The owners have a permit for a new dock and it will convey. By the water is a large screened in Gazebo perfect for crab feasts or for enjoying the abundant wildlife. The second waterfront lot is 1.2 acres, not buildable, but it does allow for more water access. The third lot is .44 acres, perc approved, level, cleared but with some mature trees . A second home could be built for a family compound or a carriage house, guest house or barn. Or, simply hold on to it as an investment. Lots of options so come take a look!

This wonderful home is ideally located just outside of Chestertown on a corner lot in the desirable neighborhood known as Kent Acres. The home has been lovingly cared for by the same owner since 1978. Location, location, location being only 2 miles to Chestertown, 10 miles to Rock Hall, and only several miles to Chester River and Langford Creek public landings. Highlights of this manageable home include true oak hardwood flooring, wood burning fireplace, tiled baths, separate den/office, screen porch with vaulted ceiling, partially finished dry basement, 3 bedrooms, 2 tiled baths, and lovely front yard with attractive landscaping. Other notable features to mention are a one car attached garage with storage cabinets, an emergency generator, and a completely new roof system in 2019. There is an adjoining half acre lot in the rear that is also available for an additional $59,000 that was perc approved in 1985. Verify perc with Kent County Environmental Health. Available perc documents are available in the documents.

This custom home is one of a kind and perfect for the golf enthusiast! Here you can walk out your back door to holes 14, 15, and 17 of the Chester River Yacht and County Club golf course. This home was built by Darling Construction eight years ago and is in immaculate condition. In this home you'll enjoy cooking and entertaining in the large, upgraded kitchen with a wet bar, granite countertops, soft close cabinets, pot filler over the stove, and stainless-steel appliances. Enjoy your days in the sunroom... full of windows and light and your evenings in the living room by the gas floor to ceiling stone fireplace. This home has a formal dining room with French glass doors, separate office, two guest bedrooms with a Jack and Jill bath and large primary suite. The primary bedroom has two walk-in closets, laundry area, and connected to the primary bath with heated floors, dual sinks, and a walk-in shower with dual showerheads. Park your car in the oversized, side entry three car garage that leads into the house with a guest bath and pantry. A spectacular feature of this home is that it is completely handicap accessible. Wide halls, large doorways, zero steps, roll in shower and handrails. This property has all the upgraded features including, a geothermal system, crown molding and chair railing, recessed lighting, tray ceilings, 9'+ ceilings, tankless hot water heater, full concrete crawlspace, lawn sprinkler system, and so much more! Be sure to schedule your showing right away because this home is hard to find!

Almost complete, finishing touches in progress.....3 bedroom 2 bath contemporary rancher on 1 acre, kitchen with Island, primary bedroom with full bath and walk-in closet, family room overlooking 12x23 back patio and separate laundry room. Upgrades include large primary walk-in closet with built-ins, custom entry storage, floating shelves, pella windows and gutter guards. Beautiful private country setting with lots of wildlife. Estimated completion is end of mid November MHBR #9045...More pictures coming soon

Beautiful home boasting nearly 4000sqft In a great neighborhood located in Queen Anne's Co and conveniently located less then 3 miles from Chestertown for shopping and those quick runs to the store. Located in a highly desired school district area. Standing metal seam covered front porch leads in to your beautiful front foyer as you enter the front door with a set of double steps. Wide open floor plan with a large kitchen and a big center Island that flows right in to the living room, Corian counter tops, tile backsplash. Hardwood floors and tile flooring. 2 - Zone HVAC, New Heat Pumps Installed 2021. Formal front dinning room right off the kitchen, out back you will find your beautiful Oasis to relax and enjoy your time poolside. Large step up master bedroom with tray ceilings, walk in closets, double vanities, deep soaking tub. This home also offers a Huge walk out basement at 1928Sqft with bathroom rough in for more flex space. Peaceful neighborhood on a cul-de-sac lot super safe for kids. Black top drive way, large garage.

Located in the historic district of Chestertown! Well maintained with an open floor plan and currently tenant occupied. The gleaming wood floors on the main level gleam! Amazing 2" x 6" exterior wall construction w/concrete crawl space, fire suppression system, granite kitchen counter tops. Large pantry. Master bedroom on the main level with double vanities and walk in closet. The exterior is finished with Hardiplank siding. Shared driveway. All photos were taken in 2017. New updated photos coming as soon as professional photographer provides.

An Eastern Shore Haven: twenty picturesque acres, 10+/- wooded, with exceptional hunting in a trophy whitetail deer corridor and where wild turkey roam and roost. A gorgeous and classic 1999 custom built home, modeled after a Nantucket fishing Captain's cottage, with nine foot ceilings, solid wood doors, Kolbe&Kolbe windows, a comfortable screened porch, wood burning fireplaces, and a gourmet, open concept kitchen. Above the garage is the caretakers apartment with a private entrance, featuring one bedroom, full bathroom, and kitchenette. Fenced acreage, turn-out sheds, automatic waterers, a three stall barn with connected paddocks, and all the necessary amenities. The idyllic pond and gazebo offer the perfect spot to picnic and relax. The gunite "sport" pool is accompanied by a shaded pergola and a storage shed.

Magnificent Building Site on the Chester River. Being sold together⦠two lots totaling 30+ acres of property along the Chester River in Queen Anneâs County. Private lane with large oak trees towering over the driveway, high (30â+/-) elevation, 1,200â+ of Shoreline. The property is generally surrounded by about 5,500 acres of property that is subject to a conservation easement and includes an easement for recreational use of those 5,500 acres. One of the lots also includes a grandfathered pier and boat house. The property is one of several created as part of the subdivision of what was once referred to as Grasslands Plantation and is subject to some covenants that run in favor of the other property owners. The largest portion of the surrounding land is now owned by Washington College, which conducts migratory bird research there. MLW is 20â at pier!!!!!! That is not a typo. Northwestern Exposure. Outstanding location with rolling farm fields and close proximity to Historic Chestertown MD and easy commute to Wilmington/Philly/NJ/NY as well as Balt/Washington/NOVA.

Lovely rancher on over 3/4 of an acre. Private country settling but only 10 minutes to town. Bedrooms are split with the owner's suite on one side and the two additional bedrooms on the other side. Nice wood stove in the living room for a warm, cozy heat during the winter. Beautiful hardwood floors throughout most of the house. Formal dining room. Deck off the living room with pretty views of the back yard. Large uninished basement. $300 road maintenance fee.

Welcome to the Byford Heights community! This home is comfortable and inviting and offers one floor ease of living . Study with vaulted ceiling and skylights and sliding glass door to the backyard could also be used as a fourth bedroom! Living Room and Dining Room also have sliding glass doors to the backyard where the pool and patio are located. Hardwood floors throughout entire house. Primary bedroom has walk in closet. Dry walled garage with overhead storage. Mature landscaping. Great location - walk to historic downtown Chestertown for shopping and restaurants and the water! It is also Convenient to the Hospital and College.

A unique property for sale, and a rare opportunity in this charming historic town. The building is in the process of renovation. Currently down to the studs, much of the preparation work to rebuild is done, ready for the next phase. Plans have been approved by the city and would be made available to qualified prospective buyers. Located downtown, bordered on one side by the broad lawns and trees of the Kent County Courthouse, and on the other by charming historic homes. 5 minute walk to the Chester River and town amenities, galleries, restaurants, farmerâs market, boutiques, artists studios, parks and nature walks. Up to 3 Bedrooms/2.5 Bathrooms possible.

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. In the historic district, four blocks to downtown, but close to Chestertown's Rail for Trails, which is a nice, paved 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.

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.

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 has a wonderful, large, light filled owner's suite with a large en suite that has plenty of room. The additional bedrooms are terrific sizes, and the one on the end is a perfect bonus room. It could be a den, playroom, large office, game room, it's your choice! 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. Chestertown is a beautiful place to call home. There is so much to do in our beautiful rural setting. Washington College offers a Lifetime Learning Center, along with state of the art amenities including a Fitness Area that offers just about any exercise you could want. There are many activities available in our area, tennis, boccie teams, running/biking groups, sailing, swimming, walking trails that meander through the town. Of course, being located on/near the Chester River is such a thing of beauty! Rowing, skiing, fishing, are at your fingertips. There are many public landings in Kent County along with marinas that offer access to our many water ways. The YMCA opened a world class center that has so much to offer, a pool, ,weight room, basketball, pickle ball, fitness center, classes, personal training, a sauna, and locker rooms for your convenience.