Chestertown Homes for Sale

Chestertown Homes for Sale

Welcome to Chestertown, Maryland—a picturesque town that beautifully blends history with modern charm. Nestled along the banks of the Chester River, this vibrant community is steeped in rich heritage, featuring well-preserved colonial architecture and a lively arts scene. With its quaint streets, inviting shops, and delightful eateries, Chestertown offers a warm and welcoming atmosphere that makes it a perfect place to call home.

One of the town’s standout features is its commitment to preserving the natural beauty of the area. Residents can enjoy scenic parks, waterfront activities, and the stunning views that come with living near the river. With a strong sense of community, Chestertown hosts numerous festivals and events throughout the year, from the renowned Chestertown Tea Party Festival to art shows and farmers' markets, ensuring there’s always something happening.

For those considering making Chestertown their home, you’ll find a diverse selection of homes for sale that cater to a variety of lifestyles. Whether you're searching for a charming historic home with character, a modern townhouse with contemporary amenities, or a spacious family residence, Chestertown has something for everyone. With its affordable housing market in comparison to larger cities, buyers can discover excellent value in this idyllic setting.

Living in Chestertown means embracing a lifestyle that balances tranquility with vibrancy. With its rich history, beautiful landscapes, and a strong sense of community, it’s no wonder that so many are drawn to this charming town. Explore the homes for sale today and take the first step toward making Chestertown your new home!

Newest Chestertown Homes for Sale

7570 Muirfield Dr, Chestertown
$895,000
4 Beds ⋅ 3 Baths
Elegant Golf Course Living on Maryland’s Eastern shore. Experience the understated elegance of Eastern Shore living in this beautifully crafted, custom-built residence overlooking the 10th tee and fairway of the Chester River Yacht & Country Club. Set on 1.45 acres of thoughtfully landscaped grounds in the desirable Prestwick community, this exceptional property offers privacy, timeless craftsmanship, and the ease of single-level living. Custom-built by Alton Darling, the approximately 2,500-square-foot home features an inviting, open floor plan with hardwood floors, elegant crown molding, and generously proportioned rooms designed for comfortable everyday living and effortless entertaining. The spacious primary suite provides a peaceful retreat with two walk-in closets and a beautifully appointed bath featuring dual vanities with quartz countertops, an oversized walk-in shower. Two additional bedrooms, thoughtfully situated in a separate wing, offer privacy for family and guests. A formal dining room, breakfast room, and versatile office or 4th bedroom space provide flexibility for today’s lifestyles. The kitchen features granite countertops, updated appliances, and convenient access to the home’s gathering spaces. Freshly painted interiors and numerous system improvements further enhance the property’s appeal. Beyond the interiors, the home’s setting truly distinguishes it. A screened porch overlooks mature landscaping and the picturesque golf course, creating an inviting place to enjoy morning coffee, entertain friends, or simply appreciate the peaceful surroundings. A new hot tub and outdoor gathering area offer additional opportunities for relaxation. An attached two-car garage, generous storage, and extensive mechanical and safety improvements complete this thoughtfully maintained residence. Appliances 2024, washer/dryer 2025 More upgrades in the document section.

7570 Muirfield Dr, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

111 Kent St S, Chestertown
$450,000
2 Beds ⋅ 3 Baths
Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this detached home stands as a testament to meticulous craftsmanship and thoughtful design, ensuring an exceptional living experience. Step inside to discover an open floor plan that invites natural light to dance across the spacious interiors. The heart of the home features a cozy gas fireplace, perfect for creating warm, inviting gatherings. The well-appointed kitchen is a culinary enthusiast's dream, equipped with high-end appliances including a built-in range, microwave, and dishwasher, all seamlessly integrated for both functionality and style. The stacked washer and dryer add convenience, making laundry days a breeze. With two generously sized bedrooms and two and a half elegantly designed bathrooms, this home provides ample space for relaxation and rejuvenation. Each bathroom boasts modern fixtures and finishes, ensuring a spa-like experience at home. The attic space while unfinished, has the ability to be finished for additional living space, if desired. The exterior of the property is equally captivating, featuring beautifully maintained sidewalks and exterior lighting that enhances the home's curb appeal. Enjoy serene evenings on the private patio, where you can unwind and soak in the tranquil surroundings. The lot, spanning 1,330 square feet, offers a manageable outdoor space that complements the busy lifestyle of today's homeowner. Located in a vibrant community, this residence is not just a home; it's a lifestyle. The Chestertown Historic District is renowned for its rich history and picturesque streets, providing a unique backdrop for your daily life. Enjoy leisurely strolls through charming neighborhoods, explore local boutiques, or indulge in the culinary delights of nearby restaurants. This property is more than just a dwelling; it's an opportunity to embrace a luxurious lifestyle in a historic setting. With its impeccable condition and high-end features, this home is ready to welcome you into a world of comfort and elegance. Don't miss your chance to own a piece of this exclusive community-schedule your private tour today and experience the allure of this remarkable residence for yourself.

111 Kent St S, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

108 N Water St, Chestertown
$1,125,000
5 Beds ⋅ 4 Baths
This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in historic Chestertown. The formal main entry, with dual brick steps approaches a generous landing, faces away from the street. At first a curiosity until you learn that a prominent family discovered the architectural plans for their "dream house" would not fit horizontally to face the prized road. During its' 100-plus years of life, the front porch (or was it the side?) was converted to a remarkable library, with requisite bookcases, and enjoys light from three sides. The formal parlor, with wood-burning fireplace and reclaimed 19th century moldings and mantle, is left of the straight-through center hall with classic black and white porcelain tiles. The intimate, yet well-proportioned dining room enhances the exceptional flow of the first-floor public rooms. A discreetly positioned powder room and butler's pantry with window and original cabinetry is conveniently placed before entering the large and sunny kitchen with premium custom cabinetry, appliances and finishes from a 2012 renovation. Two distinct patios, one screened and accessed from the dining room and the other from kitchen, overlook the large, rear garden with mature trees and landscaping. The center stairs, with a palladium window bathing light onto the steps, takes you to the first of two oversized landings that have served many lifestyle-uses over the years. The water view primary suite was renovated in 2022 by locally acclaimed Taylor Loughry LLC and boasts a timeless, luxurious aesthetic with custom built closets and Waterwork bath fixtures. Two additional bedrooms and refreshed bath with Restoration Hardware finishes, occupy the second floor. The third floor, with its own generous landing gives access to an ensuite bedroom with walk-in windowed closet (perfect for a future cedar lined closet) and a substantial sized fifth bedroom or multi-purpose space facing the Chester River and exquisite neighboring architecture. Rear yard might accommodate a pool.

108 N Water St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

317 Rolling Rd, Chestertown
$229,900
3 Beds ⋅ 2 Baths
Located in the College Heights neighborhood of Chestertown, this 3-bedroom, 2-bath home is situated on a .34± acre lot and is full of potential! Enjoy the convenience of stepping right out your back door to the dog park, all while being within walking distance of downtown Chestertown’s shops, restaurants, and waterfront. With a little TLC and your personal touch, this property is a great opportunity to make a home your own in a fantastic location!

317 Rolling Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

7545 Quaker Neck Rd, Chestertown
$175,000
3 Beds ⋅ 1 Baths
Needs work. Sold as is

7545 Quaker Neck Rd, Chestertown

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact:

8668 Elm Rd, Chestertown
$349,900
4 Beds ⋅ 2 Baths
Brand new construction in water oriented Tolchester Estates located on the Chesapeake Bay. 4 Bedroom, 2 bath Cape Cod on a wooded lot and quiet neighborhood. Community offer private beach and boat ramp access. Rear private deck.

8668 Elm Rd, Chestertown

Listing courtesy of Kevin Dey Realty. Contact:

7655 James Ln, Chestertown
$519,900
3 Beds ⋅ 3 Baths
Enjoy a peaceful country setting at 7655 James Lane. Situated on a two-acre lot along a quiet cul-de-sac street, this well-maintained ranch home offers approximately 2,475 square feet of living space, three bedrooms, and two-and-a-half bathrooms, complemented by mature landscaping and a scenic farmland backdrop. A cozy front porch welcomes you inside to a spacious layout featuring separate living and family rooms, a formal dining area, and an eat-in country-style kitchen with rich wood cabinetry and stainless steel appliances. Flowing through the main living area are hardwood floors leading to a large and bright sunroom. The sunroom, complete with skylights offers an inviting space to relax and enjoy the surroundings, with a dedicated mini-split providing heating and cooling for year-round comfort. Just off the sunroom, a deck extends the living space outdoors, while a fenced portion of the yard offers additional flexibility for outdoor enjoyment. The attached two-car garage provides convenient parking and storage. A standout feature of this property is the large pole building, measuring approximately 40' by 22', with a heated shop and two tall doors—one at the front and another on the side—for RV or boat storage. This versatile building offers valuable space for projects, equipment, and recreational vehicles, along with a mezzanine storage loft above the shop. The rear of the building provides additional unfinished storage space with separate access. Located approximately 10 minutes from Chestertown, Rock Hall, and the public boat launch at Broadneck Landing, this property pairs a peaceful rural setting with convenient access to nearby shops, dining, and boating. Schedule your tour today!

7655 James Ln, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

24607 Chestertown Rd, Chestertown
$365,000
3 Beds ⋅ 3 Baths
Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country living while remaining just minutes from downtown amenities, this 3-bedroom, 2.5-bath home has plenty to offer. **A brand-new well and septic system have just been installed**, providing an important recent improvement for the next owner. Inside, you'll find a welcoming entryway, formal dining room, and spacious kitchen featuring an island, gas cooktop, and cozy breakfast nook. The dedicated laundry room offers convenient access to the side yard, while the comfortable living room provides a warm gathering space centered around a working fireplace. A mix of wood, tile, and carpet flooring adds character throughout the home, and two bathrooms have been recently updated. Outside, enjoy the expansive backyard with room to relax, entertain, or simply take in the extra space. The detached two-car garage offers additional flexibility with a separate area ideal for a workshop, home office, or hobby space, along with a loft ready for your ideas. With a new well and septic system and a convenient location just outside of town, this property offers space, versatility, and the opportunity to enjoy Eastern Shore living close to everything Chestertown has to offer!

24607 Chestertown Rd, Chestertown

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

8901 S Bayview Dr, Chestertown
$525,000
3 Beds ⋅ 3 Baths
The Perfect Maryland Retreat with Chesapeake Bay Views Close By. Experience the quality of a custom-built Cape Cod crafted by a reputable local builder. Lovingly maintained by its original owner, this home is completely move-in ready and features a freshly painted interior throughout. Whether you are looking for a full-time residence, a weekend getaway, or a holiday retreat, this property offers a peaceful escape. The home features a Chestertown address but sits closer to Rock Hall, giving you the absolute best of both worlds. You are perfectly positioned to enjoy the vibrant Rock Hall festivities and marinas, while still being just a short drive from the famous Chestertown Farmers Market and Historic Downtown, with their variety of Festivals and events throughout the Year. Arrive via the welcoming, roomy front porch, an inviting space to sit, relax, and take in the quiet surroundings. Inside, the main level features an open floor plan where the living room, anchored by a cozy propane fireplace, flows beautifully into the dining area to make the space feel inviting and roomy. The eat-in kitchen opens directly onto a back deck, making outdoor grilling and relaxation easy. The highly sought-after primary bedroom is conveniently located on the main level for easy first-floor living. Upstairs includes additional bedrooms, plenty of easy-access storage space, and a versatile, fully finished bonus room over the garage with a convenient interior entrance—ideal for a home office, hobby room, or guest suite. For hobbies and storage, the property excels. The oversized garage offers ample room for parking plus a dedicated project/workshop space. Below, a partial walk-out basement provides exterior access, making it incredibly easy to store gear or access the home's systems. Situated in a desirable water-oriented community, you will enjoy peekaboo views of the Chesapeake Bay right from the house. Best of all, the neighborhood features its own small private beach for easy enjoyment, making it effortless to relax by the water and perfect for collecting sea glass, beachcombing, and watching the sunset. This classic, beautifully refreshed home is ready for its next chapter!

8901 S Bayview Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

21338 Virginia Ave, Chestertown
$400,000
2 Beds ⋅ 2 Baths
Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-style residence offers a harmonious blend of modern living space and coastal charm, perfectly situated approximately 800 feet from the breathtaking Chesapeake Bay. Step inside to discover an open-concept layout that seamlessly integrates the kitchen, dining, and living areas, creating an inviting space ideal for both entertaining and everyday living. The interior features luxury vinyl plank flooring that exudes sophistication while ensuring durability and ease of maintenance. The thoughtfully designed kitchen is a cook's dream, equipped with new appliances including a built-in microwave, dishwasher, stove, and refrigerator, all complemented by a sleek exhaust fan. The combination of functionality and style makes this kitchen the heart of the home. With two spacious bedrooms , and two fully appointed bathrooms, this residence offers comfort and privacy. The main floor laundry adds convenience to your daily routine, while the attached side-entry garage provides easy access and additional storage options. Step outside onto the expansive deck, where you can bask in the serene views of the bay, perfect for morning coffee or evening gatherings under the stars. The outdoor space is an extension of the easy lifestyle this home offers, allowing you to enjoy the tranquility of nature right at your doorstep. The property is not just a home; it's a lifestyle. Living in Tolchester Estates means embracing a community that values both privacy and connection, with the Chesapeake Bay as your backdrop. Enjoy leisurely strolls along the water, or indulge in water-oriented activities that the bay has to offer. This home is designed for those who appreciate easy living, with a commitment to quality evident in every detail. From the excellent condition of the property to the thoughtful selection of materials, this residence is a jewel. Don't miss the opportunity to own a piece of paradise in this exclusive bay block location. Experience the luxury, comfort, and lifestyle that await you in this remarkable home. Your dream of coastal living starts here. Within 5 minutes of a full-service marina and "The Shanty" for fun entertainment located on a beach right in front of the Chesapeake Bay. There are also community beaches, one is about two minutes from this cottage!

21338 Virginia Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

106 Harlan Loop, Chestertown
$425,000
4 Beds ⋅ 3 Baths
Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the finer things in life. Built in 2009, this stunning home boasts 3,165 square feet of meticulously designed living space, ensuring ample room for both relaxation and entertainment. Step inside to discover an inviting interior adorned with high-end finishes and thoughtful details. The spacious family room, seamlessly connected to the kitchen, is perfect for gatherings, while the formal dining room sets the stage for elegant dinner parties. The gourmet kitchen is a chef's dream, featuring a generous island, stainless steel appliances, and a convenient pantry, all bathed in natural light from the double-pane windows. Enjoy casual meals in the cozy breakfast area, where morning sunlight creates a warm ambiance. Retreat to the luxurious primary suite, complete with a walk-in closet with an additional closet and a spa-like bathroom featuring a walk-in shower and double sinks. Each of the additional three bedrooms offers generous space and comfort and large closets, ensuring everyone has their own sanctuary. Recessed lighting and ceiling fans throughout enhance the home's inviting atmosphere, while plush carpeting and laminate flooring provide a perfect balance of style and practicality. The partially finished basement offers endless possibilities, whether you envision a home theater, gym, or additional living space. The basement even has a rough in for an additional bathroom. With interior access and heating, this area is ready to be transformed into your personal oasis. Outside, the property sits on a 0.28-acre lot that backs to serene trees, while the front over looks the large common area providing a tranquil backdrop for outdoor living. The expansive deck invites you to unwind and entertain, while the attached garage and ample driveway space accommodate all your vehicles with ease. This home is not just a residence; it's a lifestyle. Enjoy the peace of mind that comes with living in a well-established community, where every detail has been considered for your comfort and enjoyment. Experience the perfect blend of luxury, convenience, and nature in this exceptional Coventry Farms II gem that is "Move In Ready". Enjoy a walk in Downtown Historical Chestertown which is on the Chester River. Explore many events that the town has such as Saturday morning Farmers Markets, The Annual Tea Party, Downrigging Festival, Fourth of July Fireworks, tours on the Sultana and River Packet and Dickens of a Christmas or just relax on a bench by the River or Wilmer Park. Don't miss the opportunity to make this dream home your reality! Chestertown is a great place to call Home!

106 Harlan Loop, Chestertown

Listing courtesy of Douglas Realty LLC. Contact:

8986 Orchard Dr, Chestertown
$679,900
3 Beds ⋅ 4 Baths
Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level living with 3 bedrooms, 2 bathrooms, and a partially finished basement with endless possibilities. Enjoy a spacious living room with recessed ceilings, an inviting primary suite with a jetted soaking tub, and updates throughout, including a new roof in 2025 and an efficient HVAC system upgraded in 2022. The partially finished basement features a private, ground-level walkout entrance, studio-style living space with a pool table, an efficient mini-split system, and plenty of additional storage or workshop space. French drains and an automatic sump pump add peace of mind. Outside, enjoy multiple spaces to relax and entertain, including a screened-in porch, open deck, patio with a hot tub that conveys, and a partially fenced backyard surrounded by beautiful crepe myrtles. Additional highlights include a two-car garage, a large floored attic for extra storage, and a solar system installed in August 2025. Conveniently located within 10 minutes of Chestertown's everyday amenities, shopping, dining, and more, this property offers the perfect blend of comfort, flexibility, and convenience. Come see all that this home has to offer! *Sellers offering credit towards painting*

8986 Orchard Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

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