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234 N Kent St, Chestertown
$325,000
5 Beds ⋅ 2 Baths
Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones… remarkable. Solid construction, generous proportions, and historic detail at every turn — the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home — a true owner's retreat, a guest wing, or a quiet work-from-home floor of its own. Outside, a fully fenced backyard is ready for pets, play, and entertaining, a large shed could easily become a garage, studio, or workshop. The driveway provides off-street parking, a definite bonus for Chestertown. And the location is the whole point. You're roughly three blocks from everything Chestertown offers — the shops, restaurants and galleries along High Street, the Chester River waterfront, the farmers market, and the historic charm of one of the Eastern Shore's best-loved small towns. Bring your contractor, or be your own. Come see the possibility.

234 N Kent St, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

8820 Cumberland St, Chestertown
$312,500
3 Beds ⋅ 2 Baths
Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in the peaceful water-privileged community of Tolchester Beach. Built in 2006, this inviting residence combines a comfortable floor plan, desirable outdoor space, and an attached two-car garage with a setting that encourages you to slow down and enjoy the best of Maryland's Eastern Shore. The thoughtfully designed interior provides an easy flow for everyday living, with three well-proportioned bedrooms and two full baths all conveniently located on one level. Whether you're entertaining, working from home, or simply enjoying a quiet evening, the home's practical layout offers flexibility for a variety of lifestyles. Step outside to the rear deck, where a wooded backdrop creates a tranquil setting for morning coffee, outdoor dining, or relaxing at the end of the day. The surrounding natural scenery adds a welcome sense of privacy and peacefulness. The community's water-oriented amenities add to the appeal, with opportunities to enjoy the community beach, fishing, local marina, and the laid-back lifestyle that makes the Eastern Shore so desirable. Ideally positioned between historic Chestertown and waterfront Rock Hall, the home places shopping, dining, marinas, boating, and local recreation within convenient reach. Whether you're seeking a full-time residence, weekend retreat, or low-maintenance Eastern Shore escape, 8820 Cumberland Street offers an appealing blend of comfort, convenience, and coastal lifestyle. This property is being sold as-is, property is lender-owned and U.S. Bank National Association is making no representations or warranties. U.S. Bank National Association may have financing options available.

8820 Cumberland St, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

103 Metcalf Rd, Chestertown
$259,900
3 Beds ⋅ 3 Baths
Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month — even more on lower-down-payment financing. This is real payment relief in today's market — often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

103 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

331 Devon Dr, Chestertown
$499,999
4 Beds ⋅ 4 Baths
Welcome to 331 Devon Drive in Family friendly Coventry Farms. With 4 bedrooms and 3.5 bathrooms, this recently updated and meticulously maintained Colonial home offers enough space for the whole family and a harmonious blend of convenience and elegant living. The well-designed first floor - featuring tall ceilings, new dimmable recessed lighting and a wood burning fireplace - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the exterior deck. The upgraded gourmet kitchen is a chef's dream, featuring upgraded countertops, stainless steel appliances, and a spacious island that invites culinary creativity. The kitchen flows effortlessly into the family room, where a cozy fireplace serves as the focal point, perfect for gathering with loved ones. The back of the house flows easily through sliding glass doors to the large back deck overlooking a large community open space with trees and a rolling field. A formal dining room off the kitchen and a large office space complete the first floor. Moving upstairs, there is brand new carpet throughout all four bedrooms. The master suite is a true retreat, complete with a walk-in closet and an en-suite bathroom. The attached garage accommodates two vehicles, while the paved driveway provides additional parking for guests. An electric vehicle charging station is great for those with an EV. The finished walkout basement with a full bathroom is a large open space offering possibilities for a second living room, home gym, entertainment area, etc. A Sunrun Solar system has significantly reduced the home's electric bill. Recent upgrades include: GE Profile SS kitchen appliances, deep farm-style sink, Trane heating / air air system, recessed lighting, fans, second floor carpet, interior and exterior paint throughout and more. Coventry Farms is just a couple minutes from downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Home to many festivals, an award-winning weekly Farmer's Market, Chestertown has a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. More photos and information to come!

331 Devon Dr, Chestertown

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

10 Cedar Chase Ct, Chestertown
$495,000
3 Beds ⋅ 3 Baths
Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on .53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating could transform the existing spaces into a home that takes full advantage of the setting. Within a short walk or bike ride to Chestertown's Historic District for dinner, shopping, galleries, and Annual Festivals, while the Chester River provides a beautiful backdrop to everyday life. Bring your vision and create a truly special waterview home and experience the Eastern Shore Lifestyle at its finest!

10 Cedar Chase Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

22974 Bay Shore Rd, Chestertown
$329,900
2 Beds ⋅ 2 Baths
Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm. Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home and features beautiful finishes and newer appliances, making it a great space for cooking and gathering. The home features two bedrooms, including a spacious primary bedroom, and two full bathrooms that have both been nicely updated. The spacious laundry room/mudroom provides plenty of room and adds everyday convenience. Enjoy your morning coffee or unwind at the end of the day on the inviting front porch, a great spot to sit back and enjoy the peaceful surroundings. Outside, you’ll find a large half-acre lot that backs to farmland, offering a beautiful setting. There’s plenty of room to enjoy the outdoors, garden, or let the kids and pets play. The gravel driveway provides parking for up to four vehicles. If you’re looking for a home that has been beautifully updated while still keeping that cozy farmhouse feel, this one is worth a look. Come see everything this Fairlee home has to offer!

22974 Bay Shore Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

105 N Water St Unit 3, Chestertown
$489,000
2 Beds ⋅ 2 Baths
Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunning view of the Chester River. One of the most coveted streets in historic Chestertown!

105 N Water St Unit 3, Chestertown

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

8732 Elm Rd, Chestertown
$289,000
3 Beds ⋅ 2 Baths
Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining and living room area. The back deck with a built in bench is just perfect for relaxing, entertaining and watching the abundant wildlife. This water oriented, water access community offers a community beach on the Chesapeake Bay, a boat ramp and a community hall for gatherings and events. Tolchester Marina, a full service operation, and The Shanty Beach Bar, "Best Kept Secret on the Bay", are just a short walk or golf cart ride away. This low maintenance home can easily be a primary resident, second home or investment property. Enjoy the easy pace and the stunning sunsets this community has to offer (some interior images were virtually staged using AI - these images do not represent the property's current furnishings or decor).

8732 Elm Rd, Chestertown

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

7415 Wilkins Ln, Chestertown
$229,000
3 Beds ⋅ 1 Baths
This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly increase rental income or resale value. The spacious 0.34-acre lot provides ample outdoor space, while off-street and driveway parking enhances convenience for residents. A shed on the property offers additional storage options, appealing to renters seeking practicality. With no pool maintenance costs and a straightforward layout, this property is low-maintenance, making it an attractive option for investors looking to maximize returns. The combination of location, features, and potential for appreciation makes this property a compelling addition to any real estate portfolio.

7415 Wilkins Ln, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

24775 Langford Rd, Chestertown
$315,000
3 Beds ⋅ 1 Baths
Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas.

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

104 Lincoln Dr, Chestertown
$285,000
3 Beds ⋅ 1 Baths
**OPEN HOUSE Saturday October 3rd 10AM-12PM** This adorable rancher combines a fresh, updated interior with plenty of outdoor space to enjoy. Come step inside to a bright and welcoming home filled with natural light, LVP flooring and a modern, neutral color palette that flows throughout. The crisp white kitchen keeps things light and timeless, while the spacious living room offers plenty of room to relax, gather and make the space your own. Three comfortably sized bedrooms provide flexibility for sleeping, working from home or creating a dedicated hobby space. The updated full bathroom continues the fresh aesthetic with tile flooring and a coordinating white vanity. Even the everyday necessities have been thoughtfully considered with a dedicated laundry closet featuring a full-size washer and dryer plus shelving for additional storage. Outside, the large corner lot gives you room to spread out without sacrificing that familiar neighborhood feel. Step through the rear entry onto the newer paver patio, perfect for grilling, outdoor dining or relaxing while overlooking the playset and backyard. Vinyl privacy fencing, a storage shed, long driveway and plenty of usable outdoor space round out the property. With main level living, thoughtful updates and neighborhood vibes without the community HOA, this home offers an easy, comfortable lifestyle with plenty of opportunity to make it your own.

104 Lincoln Dr, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

212 Washington Ave, Chestertown
$675,000
5 Beds ⋅ 3 Baths
This charming American Four Square has been meticulously maintained and is located 1 block from Washington College’s campus and near Chestertown’s Historic District’s shops and restaurants. All of the key features of this architectural style are evident - two and a half stories high, hipped slate roof with a distinctive dormer at the front of the house, spacious four-room plan and full front porch with mahogany flooring with a depth that makes it a wonderful outdoor room. The American Four-Square was designed for narrow urban lots and this property’s bonus is its deep lot that easily accommodated an addition of a kitchen-family room opening onto a deck and a deep rear fully fenced back yard that offers safe play for children and pets. Another bonus is a two-car garage. From the foyer, the “U” shaped artisan stair rises to the third floor and the main floor’s living room, dining room, bathroom and library are seamlessly connected to maximize the rooms’ sizes. The rear addition of an open plan kitchen-family room has easy indoor-outdoor flow to the adjacent deck. The second floor contains 3 bedrooms and 2 full baths as well as the laundry. The third floor contains two additional bedrooms. Throughout the house, details of original wood floors, moldings and trim, corner guards and bespoke millwork evoke an earlier era of gracious living. A uniquely American architectural style, with an addition and updates for today’s family lifestyle; freshly painted exterior, meticulous mature landscaping, fenced rear yard that is a verdant oasis, two-car garage - who could ask for anything more?

212 Washington Ave, Chestertown

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

217 Edmore Rd, Chestertown
$335,000
3 Beds ⋅ 2 Baths
Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then. Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings. Updated laminate plank floors throughout entire home with SS appliances and kitchen breakfast bar, plus separate dining area. Stackable laundry and half bath conveniently located just off dining area. The sun room, over looking the back garden makes a great sitting room, office, or flex space. Down the hall you'll find 3 good sized bedrooms, all with double closets, a good sized bathroom with modern vanity, laminate floors and tub shower. Outside is a gardener's oasis with mature specimen plantings, just waiting for you to make it your own!

217 Edmore Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

23208 Buck Neck Rd, Chestertown
$349,900
3 Beds ⋅ 3 Baths
SELLER-PAID PERMANENT RATE BUYDOWN available on this brand-new home. The builder is buying down your interest rate — and the preferred lender is adding a credit toward closing costs — to put a significantly lower monthly payment within reach, saving you hundreds of dollars a month for the life of your loan. In a market where every point matters, this is a rare chance to own new construction at a payment that actually works. Quality finishes, modern systems, and a builder-backed warranty throughout. Buydown applies when financing with the preferred lender; contact agent for full details. Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout — the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room — tucked away from the main living space so the first floor stays yours. The lot is a third of an acre with a private driveway, giving you real yard on all sides rather than a strip of grass between neighbors. Chesapeake Landing is a waterfront community with a clubhouse, walking trails and community water access. Membership in the community association is voluntary and carries a modest annual fee. Historic Chestertown — the shops, the restaurants, the riverfront — is a short drive away. Everything here is new. New systems, new surfaces, new appliances. Nothing deferred, nothing to renovate, nothing waiting to break in year two. Schedule your private tour today. Photos are of a previously built and sold home in the area and are shown for representation only. Exact finishes, colors, and features of this home may differ.

23208 Buck Neck Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

1003 Twin Ct, Chestertown
$499,900
3 Beds ⋅ 3 Baths
Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and easy maintenance in all bathrooms and the laundry room. The heart of the home is the impressive gourmet kitchen, featuring quartz countertops, a granite-topped island, 5-burner propane range, double wall ovens, built-in microwave, pot filler, farmhouse sink, beautiful backsplash, and abundant cabinetry for exceptional storage. Open to the spacious great room, the kitchen creates an inviting gathering space highlighted by a propane fireplace with a beautiful mantel. The living room features Anderson sliding glass doors that open to the deck, creating an easy connection between indoor and outdoor living. The spacious primary suite is a true retreat, featuring Anderson sliding glass doors leading directly to the deck, a walk-in closet, and an updated primary bath with double vanity and a large tiled shower enclosed by glass doors. The third bedroom offers clever versatility with a Murphy bed that maximizes the space while providing a comfortable guest room when needed. Step outside to enjoy the deck and partially fenced backyard, complete with a storage shed and peaceful views of the open common area behind the property. An attached two-car garage and paved driveway add convenience and functionality. Meticulously maintained and beautifully updated, this home offers a wonderful opportunity to enjoy turnkey living in a highly desirable Chestertown location, close to the town's shops, restaurants, waterfront, and amenities. Don't miss the opportunity to make this exceptional home your own!

1003 Twin Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

123 Trafford Dr, Chestertown
$370,000
4 Beds ⋅ 3 Baths
All reasonable offers considered! Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

123 Trafford Dr, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

115 Chester Arms Dr, Chestertown
$259,000
3 Beds ⋅ 2 Baths
Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities. Some listing photos have been digitally enhanced for presentation purposes. Certain furnishings and décor may have been virtually modified or added. No material structural features of the property have been altered

115 Chester Arms Dr, Chestertown

Listing courtesy of Samson Properties. Contact:

101 S College Ave, Chestertown
$359,000
2 Beds ⋅ 2 Baths
This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space. Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled floors, shiplap walls, and a laundry/half bath just off kitchen. From the kitchen step straight into the private fenced courtyard, your own peaceful retreat. With a large brick patio, privacy plantings, and ample garden space to create your own haven. Upstairs you'll find two nice sized bedrooms, re-finished hardwood floors and a good size full bath with walk in shower. If you're looking for that quiet oasis in a downtown location, this is it!

101 S College Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

7982 Radcliffe Rd, Chestertown
$399,000
2 Beds ⋅ 2 Baths
Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed off. Outside, you can enjoy the nice-sized yard with the views of a crop field and beautiful sunsets. Located right outside of Chestertown, the home puts shops, restaurants, and the local farmers market close by and is also walking distance to a view of the Chester River! An amazing opportunity to enjoy small-town living convenience, space & character!

7982 Radcliffe Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

124 Wilton Rd, Chestertown
$299,900
3 Beds ⋅ 1 Baths
MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor and Queen Anne’s County school district. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis water system in the kitchen. Numerous updates have been completed recently, including new LVP flooring, carpet, light fixtures, a new roof in 2020, new windows in 2021, new exterior and entry doors in 2023. Perfect location for dog lovers with a recently added split-rail fence enclosing the backyard. Walking distance to Round Top Park and minutes from Downtown Chestertown where you can enjoy local restaurants, shops, waterfront attractions, the dog park and the popular farmers market every Saturday! Don't miss this opportunity to make this wonderful property your new home!

124 Wilton Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

216 Birch Run Rd, Chestertown
$750,000
3 Beds ⋅ 3 Baths
Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranquil wooded views. * The generous primary suite features an en-suite bath, while two additional bedrooms makes for flexible bedroom accommodations for family, guests, or a quiet work-from-home office space. A convenient half bath and main-floor laundry round out the practical layout. A full basement offers abundant storage and endless potential for an artist’s studio, workshop, recreation room, or finished expansion. * With its pristine landscaping, mature plantings, and verdant views, this exceptional home is a rare find. And the location is second to none—just minutes from historic downtown Chestertown. Stroll tree-lined streets to discover specialty shops, art galleries, restaurants, and the Saturday Farmers Market at Fountain Park. Washington College, the nation’s tenth-oldest college, anchors the community with year-round cultural events, lectures, and performances. Outdoor enthusiasts will love the nearby Rail Trail, Sultana Lawrence Wetlands Preserve, marinas, and public boat launches providing easy access to the Chester River and Chesapeake Bay. First Friday celebrations, waterfront festivals, and a vibrant arts scene make Chestertown one of the Eastern Shore’s most beloved places to call home.

216 Birch Run Rd, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

8630 Elm Rd, Chestertown
$424,900
5 Beds ⋅ 3 Baths
Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Maryland’s Eastern Shore. Set in a waterfront community, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. Start the day with a quiet moment on the furnished front porch, then enjoy a layout with room to work from home, welcome guests, and spend time together. The fifth bedroom can serve as a home office separate from the main living area, a guest room, or a hobby space. Attractive ceiling fans throughout the home add both comfort and style. The updated kitchen features bright white cabinetry, a French-door refrigerator, and stainless-steel appliances. A new white porcelain herringbone backsplash is scheduled for installation on October 8. The spacious kitchen and dining area offer room to gather and enjoy a meal. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. Adjustable fireplace settings add to the cozy atmosphere. Step outside to the expanded deck, unwind in the hot tub, or gather around the fire pit. Imagine sharing hot chocolate and s’mores on a crisp fall evening, or taking a quiet moment to enjoy the setting and watch for local wildlife. Boating enthusiasts will appreciate the nearby seasonal marina, with restaurants and a dive bar about three blocks away, and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. The expansive driveway offers parking for up to eight vehicles, with room for multiple cars, larger vehicles, and weekend guests. The partially finished one-car garage can become a game room, hobby area, home gym, or extra gathering space. Additional features include an approximately two-year-old water heater and a private well with a water-treatment and softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Furnishings throughout the home, including the porch furniture, are included. Though built in 2006, the home has been gently enjoyed primarily as a second home or vacation getaway and has received updates and improvements, including stainless-steel appliances, a built-in electric fireplace, and the newer water heater. This home could be a great fit if you’re: Looking for a second home or vacation getaway you can enjoy yourself and explore renting part-time when you’re away. Looking for an investment property with a history of income from both traditional and short-term rentals. Certain loan programs may consider rental income when evaluating an investment property; eligibility depends on lender guidelines. Looking for a primary residence with flexible living space and convenient access to the marina. Qualified buyers may be eligible for 0% down financing. Preferred Lender Credit: Eligible buyers may receive a lender credit when using the preferred lender. Financing programs and credits are subject to eligibility, underwriting, and lender approval. Whether you’re looking for a primary residence, a weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package. Ready to see it in person? Schedule your private showing today through the listing’s appointment link!

8630 Elm Rd, Chestertown

Listing courtesy of Save 6, Incorporated. Contact:

129 Trafford Dr, Chestertown
$480,000
3 Beds ⋅ 3 Baths
PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light. The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space to enjoy your morning coffee or unwind while overlooking the backyard. You'll also find a formal dining room for hosting special occasions, a welcoming living room, and a cozy family room that provides plenty of space for everyday living. Downstairs, the finished basement offers versatile additional living space ideal for a recreation room, home theater, fitness area, playroom, or home office. There is enough space to do all of it. The unfinished area has full laundry and ample storage. Upstairs, the expansive owner's suite serves as a private retreat, complete with a generous walk-in closet and an ensuite bathroom featuring a soaking tub. Two additional bedrooms each offer large closets and ample space for family, guests, or a home office. A full bathroom conveniently located off the second-floor sitting area completes the upper level. Step outside to your own private backyard oasis. The landscaped yard features a refreshing in-ground swimming pool with a new tile finish and a new filtration system, making it ready for years of enjoyment. A new deck with a privacy wall extends from the home, providing the perfect setting for outdoor dining, entertaining, or relaxing poolside. Additional highlights include a large storage shed and a newly installed rock bed surrounding the pool deck that enhances both beauty and low-maintenance landscaping. For added peace of mind, the home also features a roof that is only two years old. Combining spacious living areas, thoughtful updates, exceptional outdoor amenities, and a desirable location in historic Chestertown, this home truly has something for everyone. Don't miss the opportunity to make this exceptional property your next home!

129 Trafford Dr, Chestertown

Listing courtesy of Elevated Real Estate Solutions. Contact:

10540 Tonopah Rd, Chestertown
$269,000
3 Beds ⋅ 2 Baths
Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

10540 Tonopah Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

1010 Twin Ct, Chestertown
$349,900
4 Beds ⋅ 2 Baths
Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but outside the town limits so no town tax or water/sewer bill! Come make this home yours today, immediate occupancy.

1010 Twin Ct, Chestertown

Listing courtesy of Kevin Dey Realty. Contact:

115 Metcalf Rd, Chestertown
$259,900
3 Beds ⋅ 2 Baths
*Open Every Tuesdy and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Priced at $259,900, this home also comes with a $5,000 builder incentive plus ½% ($1,299) through our lender partnership—making it possible to own for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

115 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

200 Manor Ave, Chestertown
$325,000
4 Beds ⋅ 2 Baths
A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and the quiet character that comes from decades of careful ownership. Step inside and the home tells its story with original trim, classic proportions and timeless architectural touches. The two-story split-level floor plan offers a thoughtful separation of living and sleeping spaces, with a sun-filled sunroom that works beautifully as a screened porch when the doors are all open or as extra living space during the shoulder seasons. Two of the bedrooms sit on the upper level, while two large bedrooms flow comfortably below. Out back, the large, gently sloped corner lot offers privacy, mature trees, and room to garden, entertain, or simply enjoy a quiet afternoon. The setting feels tucked away, while the rest of Chestertown is just a short jaunt from the front door. The two-bay carport keeps your vehicles safe from the elements in the wide stone driveway. What truly sets this home apart is its condition. It has been maintained impeccably — spotlessly clean, carefully tended, and gently lived in. The HVAC system is new, and the kitchen and laundry appliances are all young as well, giving the next owner the best of both worlds: classic character on the outside, modern mechanicals where it counts. The remaining finishes offer a thoughtful canvas for the next owner to put their own stamp on it, with the confidence that the bones and the care have already been handled. Classic character, pristine condition, and convenience to it all.

200 Manor Ave, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

121 Metcalf Rd, Chestertown
$264,900
3 Beds ⋅ 2 Baths
*Open Every Tuesday and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations.

121 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

7680 Country Club Ln, Chestertown
$825,000
5 Beds ⋅ 4 Baths
Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

7680 Country Club Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

9126 Fairlee Rd, Chestertown
$314,000
3 Beds ⋅ 2 Baths
Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and ample cabinet space. A new HVAC system, brand-new roof, and a ONE-YEAR HOME WARRANTY provide peace of mind, allowing you to move in and enjoy your new home from day one. Outside, the expansive 1.66-acre lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provides additional space for tools, lawn equipment, or outdoor hobbies. Whether you're a first-time homebuyer, someone looking for convenient one-level living, or looking for a move-in-ready home with room to spread out, this property checks all the boxes! Conveniently located just minutes from historic downtown Chestertown, Rock Hall, nearby marinas, dining, shopping, and waterfront activities - with convenient access to major routes into Delaware and Pennsylvania - this property offers the ideal balance of peaceful rural living and easy travel. This is a rare combination of acreage, versatility, and affordability. In addition, this property has public water and sewer. The property is priced below the appraised value, giving the new owner built-in value from day one! Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape!

9126 Fairlee Rd, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact: