Chestertown Real Estate

Chestertown Real Estate

Welcome to Chestertown, Maryland—a hidden gem nestled along the picturesque banks of the Chester River. This charming town, steeped in rich history and vibrant culture, offers a unique blend of small-town charm and modern amenities, making it a perfect place to call home.

Founded in the 18th century, Chestertown is known for its well-preserved historical architecture and quaint waterfront. Stroll down its tree-lined streets, where you’ll find an array of boutique shops, art galleries, and delightful eateries that reflect the town's artistic spirit. The annual Chestertown Tea Party Festival celebrates the town’s revolutionary heritage, drawing visitors from near and far to partake in lively festivities and local crafts.

Outdoor enthusiasts will revel in the natural beauty that surrounds Chestertown. With the Chester River at its heart, the area provides ample opportunities for kayaking, fishing, and sailing. Nearby parks and nature reserves offer scenic trails for hiking and birdwatching, ensuring that residents can enjoy the great outdoors year-round.

Chestertown is also home to Washington College, a liberal arts institution that enriches the community with cultural events, lectures, and performances. The college’s presence fosters a vibrant, youthful atmosphere, making it an ideal spot for families, young professionals, and retirees alike.

With its charming ambiance, rich history, and strong sense of community, Chestertown is more than just a place to live—it's a lifestyle. Discover the warmth and beauty of this delightful town, where every day feels like a step back in time, yet is filled with modern conveniences and opportunities. Your dream home awaits in Chestertown!

Newest Listings in Chestertown

2 Beds ⋅ 2 Baths

Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cabinetry, an electric range, built-in microwave, dishwasher, and plenty of space for casual dining. The primary bedroom includes two closets and a private half bath, while the second bedroom features convenient washer and dryer hookups. Upstairs, the spacious loft boasts beautiful wood flooring and access to a second-story deck overlooking the wooded backyard. Stay comfortable year-round with central air conditioning, electric baseboard heat, and the cozy warmth of a wood stove that serves as an excellent supplemental heat source during the cooler months. Additional updates include a newer central A/C system (approximately 6 years old), a new water heater, and a new water softener. Need extra space for hobbies, storage, or projects? The detached 20' x 24' outbuilding with electricity, wood flooring, and a garage door offers endless possibilities as a workshop, studio, or storage for your outdoor gear. Enjoy everything Tolchester Estates has to offer, including exclusive resident access to a private community beach and boat ramp. Just a short walk or golf cart ride away, you'll also find Tolchester Marina and The Shanty Beach Bar, where you can enjoy waterfront dining, live music, boating, and breathtaking Chesapeake Bay sunsets. Whether you're searching for a full-time residence, weekend getaway, or vacation home, this property offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle while adding your own personal touches. Being sold as-is.

21146 Montana Ave, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

List Price is opening bid. Online Auction Only! Bidding begins Saturday, August 15 and ends Thursday, August 20, 2026 at 1:00 PM. Exceptional Multi-Family Investment Opportunity in Chestertown! Introducing 104 Maple Avenue, a beautifully updated 6-unit apartment building ideally located in Kent County's desirable Chestertown area. Thoughtfully renovated, this income-producing property seamlessly blends modern finishes with practical functionality, making it an outstanding addition to any investment portfolio. Each unit has been carefully improved to provide attractive, comfortable living spaces designed to appeal to today's renters. The extensive updates enhance both the property's aesthetic appeal and long-term value while helping to minimize future maintenance concerns. Upon full occupancy, the property offers an impressive Gross Annual Rent of $129,300±, presenting an exceptional opportunity for investors seeking strong cash flow and long-term appreciation. Conveniently situated near Washington College, University of Maryland Medical Center, & downtown Chestertown's restaurants, shops, waterfront, and local amenities, the location further enhances its desirability for tenants. Whether you're expanding your real estate portfolio or acquiring a high-performing multi-family asset, 104 Maple Avenue represents a rare opportunity to own a updated six-unit building in one of Kent County's most charming and sought-after communities. Features and Highlights: • (6) Apartments • Thoughtfully Updated & Beautifully Maintained Building • Stabilized Asset in a Prime Location • Gross Annual Rent of $129,300± • 7 Electric Meters • 7 Electric Panels • 3 Forced Hot Air Units • 7,296± SF Building • 8± Onsite Parking Spaces Property Breakdown: Main Level -Central A/C -Forced Hot Air Heat Unit 1 Rented for $2,225/ mo 2 Bedrooms, 1 Full Bathroom Unit 2 Rented for $1,890/ mo 2 Bedrooms, 1 Full Bathroom Second Level -Mini Split A/C & Heating System(s) Unit 3 Rented for $1,520/ mo 2 Bedrooms, 1 Full Bathroom Unit 4 Rented for $1,820/ mo 2 Bedrooms, 1 Full Bathroom Note: tenant vacating at end of August. Third Level -Central A/C -Forced Hot Air Heat Unit 5 Rented for $1,400/ mo 2 Bedrooms, 1 Full Bathroom Unit 6 Rented for $1,920/ mo 2 Bedrooms, 2 Full Bathrooms Lower Level Unfinished Basement housing utilities & storage space. The information contained herein was obtained from sources deemed to be reliable, but is offered for informational purposes only. Neither the auctioneer or the owner make any representations or warranties with respect to the accuracy of information.

104 Maple Ave, Chestertown

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

3 Beds ⋅ 2 Baths

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment. A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business, storage, agricultural use, or hobby space. A recently installed new roof helps reduce renovation costs and provides a great head start on your restoration project. Whether you're looking to renovate the existing home, create a private country retreat, or capitalize on the property's versatile amenities, this is a rare opportunity with tremendous potential. Property is being sold as-is

8312 Broad Neck Rd, Chestertown

Listing courtesy of Pearson Smith Realty, LLC. Contact: 5713861075

4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Chestertown, this charming church of a little over 3,500 square feet offers a unique opportunity for continued use as a place of worship, community gathering space, or potential conversion. The property features wheelchair accessibility, on-site parking, and a layout ideal for a variety of uses. With its peaceful setting and classic structure, this building is ready to serve its next purpose. Also available with mls MDKE2006846 additionally

201 N Lynchburg St, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

5 Beds ⋅ 4 Baths

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort. Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sunbeams flood the adjoining sunroom, creating a seamless transition to the outdoors while mirroring the warmth of the home’s main-floor primary suite. This private retreat features a spacious walk-in closet and a newly remodeled, spa-inspired bath complete with new quartz double vanities, sleek updated fixtures, a large walk-in shower, and an exquisite standalone soaking tub. Offering unmatched independence and comfort, a fully self-contained ground-level suite on the lowest level serves as the ultimate in-law or guest quarters. Complete with its own private ground-level entrance, open-concept kitchen and living area, dedicated laundry, and an accessible bath with a walk-in shower, this wing ensures total convenience without sacrificing style. A new addition to the lower level unlocks movie-theater magic with a fully furnished screening room ready for immediate enjoyment. Upstairs, four generously proportioned bedrooms accompany a beautifully refreshed hall bath. The exterior grounds are nothing short of a resort-style paradise. Step out onto the back porch to take in sweeping views of the lush landscape and expansive partially fenced yard. The sparkling inground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. Surrounding the water, extensive custom hardscaping leads to a fireside gathering area, while an oversized gazebo with an outdoor fan offers a shady retreat on warm afternoons. With a brand-new roof installed in 2026, a newly resurfaced driveway, and space remaining for future additions, this estate represents a rare opportunity to experience sophisticated countryside living at its finest and, less than 5 minutes from Chestertown's restaurants, shopping, and Farmer's Market. Updates to the home are available in Documents

8999 Orchard Dr, Chestertown

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

3 Beds ⋅ 2 Baths

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: 8554500442

3 Beds ⋅ 1 Baths

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable location just minutes from local shops, restaurants, grocery stores, the YMCA, and everything Chestertown has to offer. Step inside to find a beautifully updated interior featuring fresh paint throughout and durable oak luxury vinyl plank flooring that creates a warm and inviting feel. The living area opens up to the dining area and flows into the completely remodeled kitchen that showcases crisp white soft close cabinetry, elegant quartz countertops, and stainless steel appliances; perfect for everyday living and entertaining. The home also features a renovated full bathroom, in-unit washer and dryer, and a convenient one story layout designed for comfort and accessibility. Enjoy your morning coffee or unwind at the end of the day on the covered back porch. Additional peace of mind comes with a brand new roof installed in May 2026. Whether you’re a first time homebuyer searching for a stylish, affordable, move in ready home, looking to downsize into a low maintenance property, or an investor seeking a rental opportunity in a desirable location, this home offers incredible potential. Don’t miss the chance to own a beautifully renovated home in one of Kent County’s most charming communities! Disclosure: Listing agent has an ownership interest in the entity that owns the subject property.

107 Conley Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

3 Beds ⋅ 3 Baths

Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room showcasing vaulted, beamed ceilings, a fireplace, and sweeping views of the expansive rear yard. Rich hickory hardwood flooring runs throughout the kitchen, breakfast area, living room, office, and formal dining room, creating a warm and cohesive flow across the main living spaces. The formal dining room is enhanced with elegant crown molding, offering a refined setting ideal for both everyday living and entertaining. The updated gourmet kitchen features granite countertops, abundant cabinetry, and a seamless connection to the breakfast area and main living spaces, making it both functional and inviting. The private primary suite is generously sized and offers two walk-in closets along with a beautifully appointed en-suite bath featuring a luxury soaking tub, double vanity, travertine tile flooring, and a tiled walk-in shower. Two additional bedrooms provide ample closet space and share a well-appointed full bath, also finished with travertine tile flooring and a tiled shower. Outdoor living is equally impressive with extensive mature landscaping that enhances privacy and natural beauty. A stone patio and a combination of brick and Trex decks provide multiple spaces for relaxing or entertaining while enjoying the serene surroundings. Additional features include an attached two-car garage as well as a detached one-car garage, offering exceptional storage and flexibility. Ideally located just minutes from historic Chestertown and only a golf cart ride to the Chester River Yacht and Country Club and the Chester River, this exceptional home blends privacy, convenience, and luxury Eastern Shore living at its finest.

7828 Country Club Ln, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

3 Beds ⋅ 2 Baths

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

123 Heath Rd, Chestertown

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

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: 4106733344

Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure, recording is in process. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

305 Roosevelt Dr, Chestertown

Listing courtesy of Taylor Properties. Contact:

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