Refine Search
Sort by
$668,000
5 Beds 5 Baths
Eastern Shore home, c.1890 is located in the heart of Chestertown’s historic district and is just a short stroll from the Chester River Walk, Fountain Park, shops, dining and walking trails. Every modern-day amenity has been incorporated into this lovingly renovated home while preserving the original charm. Skylights and windows let in an abundance of natural light to showcase the lovely heart pine floors and detailed millwork. The home spans three levels and greets owners through a gracious foyer opening to the library with its reading nook bookcase and fireplace. The first floor open design also features a well-appointed kitchen, breakfast room, dining room, living room and two powder rooms. The second floor is designed with two ensuite bedrooms and the top floor offers three bedrooms and a powder room. Adding to the welcoming ambiance of the property is the recently built carriage house used as a workshop/studio and an english gatehouse serving as a potter’s shed. The enchanting garden features a goldfish pond, stone walls, planting beds, and a pergola with climbing rose vines. Founded in 1706, Chestertown is set on the banks of the Chester River and is home to Washington College. Brick sidewalks are lined with lovely period homes, shops, a bakery, galleries, theatre, oyster bar and restaurants. Residents and visitors alike enjoy the river walk, parks, farmers market, walking trails, community activities and annual festivals. River cruises are available on the Chester River Packet and Schooner Sultana. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia and 1-hour from Wilmington.

111 S Mill St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$160,000
2 Beds 1 Baths
Wonderful turn key living in Chestertown. Whether it is year round or long weekends, Tolchester Village makes it easy to enjoy all the area has to offer. There are plenty of fishing and boating options nearby or take a 25 min ride over to visit Eastern Neck Island to enjoy multiple viewing, hiking and water activities. So close to Rock Hall and several Marina's with Tolchester Marina just 1.8 miles away. Maybe a day in town suits you perusing the quaint shops and or dining at one of numerous options. Then there is always the possibility of relaxing on your very own patio which backs up to protected forest land. Once home, you have a fully renovated 2 bed 1 bath on two levels with L shaped kitchen including laundry and Dining/Living combo leading to patio with in ground fire pit and large outdoor storage closet. Let this be your village!!!

21341 Persimmon Dr Unit #17, Chestertown

Listing courtesy of Coldwell Banker Realty. Contact: (703) 471-7220

$329,990
5 Beds 4 Baths
This move-in ready Verona boasting 2,302 square feet is a three-story home that offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, a large corner pantry and a peninsula with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sit in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers the fifth bedroom and a third full bathroom, as well as an option flex or storage room. The Verona includes the exclusive D.R. Horton Smart Home® Package through ADT giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

112 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$299,990
3 Beds 3 Baths
The Paige is a gorgeous 1,646 square foot two-story home, that features three bedrooms, and two and a half bathrooms. You will immediately feel at home as you enter the foyer with a coat closet and make your way into the spacious family room. With its open concept, the family room is open to the dining area and the kitchen. The well-designed kitchen offers stylish white cabinets, stainless steel appliances, a peninsula island with additional room for seating and a large corner pantry. The private powder room is down the hall along with the utility closet. Upstairs you will find the spacious owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The sizeable three secondary bedrooms share a secondary bathroom and allow for everyone in your household to have their own space. The second-floor laundry room comes complete with a washer and dryer and is located near the hall linen closet. The Paige includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

210 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$339,990
4 Beds 3 Baths
The Sidney is a 1,849 square-foot move-in ready two-story home that features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your loved ones to spend quality time together in the spacious family room, casual dining area, and kitchen. The well-appointed kitchen showcases an abundance of sarsaparilla cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

208 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$299,990
3 Beds 3 Baths
This move-in ready Paige is a 1,646 square foot two-story home, that features three bedrooms, and two and a half bathrooms. You will immediately feel at home as you enter the foyer with a coat closet and make your way into the spacious family room. With its open concept, the family room is open to the dining area and the kitchen. The well-designed kitchen offers stainless steel appliances, classic white cabinets, a peninsula island with additional room for seating and a large corner pantry. The private powder room is down the hall along with the utility closet. Upstairs you will find the spacious owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The sizeable three secondary bedrooms share a secondary bathroom and allow for everyone in your household to have their own space. The second-floor laundry room comes complete with a washer and dryer and is located near the hall linen closet. The Paige includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home.

116 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$299,990
4 Beds 3 Baths
Ready for a January move-in, the Sidney is a 1,849 square-foot two-story home that features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your loved ones to spend quality time together while in the spacious family room, casual dining area and kitchen. The well-appointed kitchen showcases an abundance of beautiful white cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room with included washer and dryer is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

114 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$329,990
5 Beds 4 Baths
Available move-in ready home in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stylish gray cabinets, stainless steel appliances, a large corner pantry and a peninsula with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers a fifth bedroom and a third full bathroom, as well as a flex room that could be used for storage. The Verona includes a washer and dryer, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

110 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$349,990
5 Beds 4 Baths
This move-in ready Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, beautiful white cabinets, a large corner pantry and a peninsula with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows you to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers the fifth bedroom and a third full bathroom, as well as a finished flex room. The Verona includes a washer and dryer, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

104 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$289,900
3 Beds 3 Baths
Come by this lovely BRAND NEW home in quaint Waterfront Community of Chesapeake Landing. This home features Luxury Vinyl & Carpet Flooring throughout, White Shaker Style Cabinets, Granite Counters, Spacious Living Room, Dining Area, Kitchen, Mud room, spacious bedrooms including a large primary bedroom suite with attached full bath on the main level and much more! The Chesapeake Landing Community offers so much including a Clubhouse, Dock and Boat Slips. Special financing programs available, including Zero Down Payment loans and closing costs assistance programs so you can own this home for less than renting. House will be complete and ready to occupancy by Spring 2023. Hurry and secure your new home today, these homes are selling within days of being released, only a few left after this until much later in 2023 / early 2024. ***House is To Be Built, contact Realtor for site plan, spec sheet and full details on this home. ***

Tonopah Rd, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

$495,000
1 Baths
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.

5179 Quaker Neck Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$369,900
3 Beds 2 Baths
**REDUCED $30k!!** This spacious 3 bedroom, 2 bath rancher has all of the makings of a terrific home! Well-situated at the end of a cul-de-sac, the back yard has room to spread out and play or enjoy the open view of it from the screened porch. Built by well-regarded local builder, Buzzy Lane, the vaulted ceilings give the home an airy, spacious feeling. The large Main Bedroom is placed on the opposite side of the home from the other two generously-sized bedrooms for extra privacy in a layout that will accommodate a variety of living needs. The Great Room has a cozy gas fireplace and connects to both the Kitchen and Dining Room. An oversized garage offers ample storage for all of your stuff. The location is on the edge of Chestertown but close to everything this historic college town has to offer. The area is a boater's dream as well. You will love living here!

1005 Twin Ct, Chestertown

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$750,000
3 Beds 3 Baths
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!

25731 Collins Ave, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$319,000
4 Beds 2 Baths
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.

626 High St, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$260,000
3 Beds 3 Baths
Nestled on a little over 2 acres, this charming home has had many wonderful updates throughout! The large, screened-in front porch will be the perfect spot to entertain guests or drink your first cup of coffee each morning. The main level of the home is bright & airy, and features a living room, full bathroom with shower, laundry/mud room, bedroom and gorgeous kitchen. The kitchen updates include modern cabinetry, upgraded stone countertops, stainless steel appliances and large island. The primary suite is just up the stairs, and has a cathedral ceiling, office area (or maybe your new walk-in closet!), and stunning bathroom. Also located on the 2nd level is a fully updated hallway bathroom and additional bedroom. The top floor features a large bonus space, just waiting for you to design for your family room, craft/hobby room, or office. The Chestertown area feels tucked away from it all, with beautiful farm and forest views along with your commute home. Looking for a delicious meal or sweet treat? Consider visiting Get the Scoop for a sundae, Waterman’s Crab House for your crab fix, Java Rock for a coffee, or maybe enjoy the outdoor dining at Harbor Shack. There are plenty of marinas nearby if you are an avid boater, or maybe take classes at the Delmarva Sailing School if it is a hobby you have been wanting to get into! THE SELLER JUST REPLACED THE WHOLE ROOF AND MORE. Sale is As-IS,

8891 Georgetown Rd, Chestertown

Listing courtesy of Caprika Realty. Contact: