Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor features a huge open-concept kitchen and living/dining room space which naturally flows onto the unmatched second-story wrap-around deck; perfect for crab feasts, bbq, and watching summer sunsets. Perched on the second floor is the primary suite with private Romeo and Juliet style balcony high above. Ensuite bath is unfinished but is plumbed and ready for tile and final fixtures. Walk down the sunroom to the oversized two-car garage with workshop behind and the massive unfinished loft above. With electric and insulation already in place, this space is a blank canvas ready to be turned into a fantastic rec room or 4th bedroom. Finishing the loft and primary bath would make the home over 3,000 square feet of finished space and 3/4 bedrooms and 3 fun baths. Add the final touches to make this space your own. Walkout basement has tons of storage for outdoor equipment and has a bedroom and full bath. Open House Saturday October 18, 10:00 - 2:00. Come join us.
Live in the heart of Chestertown’s Historic District—see your boat from your front porch! Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story waterview deck—built strong enough to support a hot tub or additional living area (double 2x8 joists per owner). Andersen composite dual-pane windows with plantation shutters offer energy efficiency and easy operation. Ample storage includes two walk-in closets plus a walk-in attic. Located on desirable Water Street, you’re just steps from the waterfront, Wilmer Park, shops, restaurants, bakeries, pubs, Farmer’s Market, arts district, and more. Cook and entertain in style with Heartland appliances and handcrafted cabinetry in the kitchen. 206 S. Water Street—a “feels-like-new” historic home in Chestertown’s most walkable location. Note The vacant lot next door is not part of this property. Separate owner.
Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another great feature of this home. Call today for your showing appointment.
Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front yard provides a polished experience with tasteful landscaping. The rear yard is quite large for a house in town and includes a raised bed garden and tidy shed. Experience the relaxed lifestyle of Chestertown with the Historic District's shops, Washington College, and the Margo Bailey park just a short walk away.
Price Improvement = Even More Value! Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bedroom, 2-bath, 1,900 square foot home, situated on a full acre with public water and sewer, no HOA, and a detached garage with electric! With the recent price change, this property now offers an exceptional opportunity—whether you’re looking for a primary residence, a weekend retreat, or a vacation home on Maryland’s Eastern Shore. The flexible layout and generous acreage make this home ideal for a relaxing getaway, with plenty of room for outdoor entertaining, hobbies, or storing boats, bikes, or recreational gear. Inside, enjoy an open-concept design with easy one-level living—perfect for hosting guests. Outside, a wide blacktop driveway provides ample parking for multiple vehicles, an RV, or a boat. The expansive yard offers space to garden, gather with family and friends, or unwind under the stars after a day on the water or exploring the area. Located just minutes from historic downtown Chestertown, 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. A rare combination of acreage, versatility, and affordability—now at an even better price. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape. FHA, VA, USDA, and conventional financing welcome.
Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on an 2.66 acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located just minutes from Fairlee Creek’s public landing for easy water access, and a short drive to downtown Chestertown and Rock Hall, this home combines comfort, convenience, and Chesapeake charm. PROPERTY CAN BE PURCHASED FOR $314,000 with .39 acres after recordation this acreage will be subdivided MLS #MDKE2005074, 1.8 ACRES SUBDIVIDED INTO 4 LOTS
Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing, keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board, great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. 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 walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.
Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample space for relaxation and entertainment. The kitchen is a chef's dream, featuring an island, eat-in space, and modern appliances including a built-in microwave, dishwasher, electric oven/range, and refrigerator. Enjoy cozy breakfasts in the bright breakfast area or host formal dinners in the separate dining room. The luxurious touches continue with walk-in closets, a convenient upper-floor laundry, and a family room that flows effortlessly from the kitchen and a separate office making this a great option for those who work from home. A first floor bedroom is idea for a guest room, play room, in-law quarters and more. The home is adorned with luxury vinyl plank flooring and plush carpeting, creating a warm and welcoming atmosphere throughout. Set on a generous 1-acre lot that adjoins open space, this property offers a serene outdoor setting, perfect for enjoying nature or future landscaping projects. The side-entry attached garage provides easy access and additional storage. With its excellent condition and thoughtful design, this home is ready to embrace new memories. Experience the perfect blend of comfort and modern living in this exceptional property. Buy with ease when purchasing this new construction home. Seller can'tt settle until January 2026
This property is primed and ready for your finishing touches—materials included! Enjoy the convenience of being just steps from historic downtown Chestertown. LVP Flooring installed on 10/04/2025 on the main and upper levels. Carpet installed on the staircase. Materials, fixtures, applicances cabinetry, washer/dryer ready to install. Discover the potential of 423 Calvert Street — a two-story, 1,136 sq. ft. townhouse built in 1992 and set on a 2,006 sq. ft. lot. This 3-bedroom, 1.5-bath home has already undergone major updates in 2025, including new flooring, appliances, fresh paint, and a newer roof. Renovations are well underway, with all remaining materials provided, giving the next owner an incredible opportunity to add the finishing touches. The property features a fenced front entry, a deep backyard with rear parking access, and plenty of outdoor space to enjoy. Ideally located near historic downtown Chestertown, you’ll find shopping, dining, entertainment, and events just minutes away, along with the waterfront park along the scenic Chester River and the nearby Washington College campus. Offered at just $135,000, this home presents exceptional value for use as a primary residence, a second home retreat, or an investment rental. All of this in Chestertown — a charming Eastern Shore community known for its rich history, vibrant arts scene, events, riverfront beauty, and welcoming small-town atmosphere.
Welcome to 515 N Kent Street in the heart of Chestertown! This charming two story home features a half-circle driveway, 1-car attached garage, and inviting brick patio leading to the front door. Step inside and you’ll love the gorgeous hardwood floors throughout the main level (2022). The formal living room showcases a wood-burning fireplace with a brick mantel, creating a warm and welcoming space. The kitchen and dining room were completely updated in 2022 with custom Amish cabinetry, quartz countertops, a farm sink, and a large island—perfect for cooking and gathering. Just off the kitchen, the laundry room offers washer/dryer, ample storage, and eye-catching brick tile flooring. From here, step into the cozy family room with wood stove, built-ins, and access to the screened porch and brick patio overlooking the private backyard. A full bath with shower and matching brick tile floors is conveniently located off the family room and garage entry. Upstairs, you’ll find four spacious bedrooms with carpet and a full bath with tub/shower. The partial basement with French drain provides flexible space for storage or playroom use, with indoor/outdoor access. This home has been well maintained with numerous updates: sewer line replaced (2017), new heat pump with central AC (2018), 50-year architectural shingle roof (2019), breaker panel and hot water heater (2024). A truly move-in ready home with character, comfort, and thoughtful upgrades—don’t miss this one!
Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors. Forced Hot Air, Fuel Oil Heating; Central Air Conditioning. Well water pump upgraded in 2016. New, top-of-the-line “Meyers” well pump, with increased HP. Public sewer so no septic systems to deal with. Four upstairs Bedrooms. The MBR and BR2 are huge. MBR has slider door to lovely Sunroom/Sitting room. The MBR features wainscotting on all walls; crown molding; custom wide molding around all 3 doors and the closet with remote controlled ceiling fan with dimmable light. Large living room with stunning fireplace. Wide, extra-long mantle, matching storage cabinets on both sides of fireplace, large picture window and crown molding. Two full bathrooms with showers are upstairs, each with new, in 2024, quiet, yet powerful Panasonic exhaust fan and LED light. One Powder Room is downstairs. Bright and airy, extra-long dining room. Tray ceiling. dimmable LED ceiling lights on separate, inner and outer ring circuits for versatility. Ceiling centerline is pre-wired (includes 3-way switches) for one or more chandelier lights; Pass-through window to kitchen with fancy tempered glass shelf. Family room with dropped ceiling bar area. Bar sink, granite counters, gorgeous glass door cabinets, wood-burning stove, versatile lighting, and a slider door to a the main level sunroom. Modern, ample-sized kitchen with movable island. Nearly new, upscale glass cooktop/oven, dishwasher and microwave. Build-in refrigerator surrounded by cabinets. Double sink, disposal and PC workstation with shelving matching cabinet. Extraordinary lighting includes under and over cabinet lights plus a ceiling fan with fancy light globes and attractive light globes over sink. MAJOR ADDITION & REHAB done in 2013: Extended DR by 13 feet and added 2nd story sunroom/sitting room on top of DR extension Total rehab of 1st floor sunroom. Top quality, long lasting architectural roof shingle for entire house; new flashing and roof vent seals. Both sunrooms have attractive, casement-style windows for exceptional ventilation. Seven Ceiling fans with attractive lighting: MBR, BR2, BR3, 2nd story sunroom/sitting room, kitchen and 2 on the porch. All four Slider Doors (servicing the porch and the 2 sunrooms) have built-in blinds for privacy and versatile light and view control. Spacious screened porch with porch swing. Massive stone and paver patio area includes three 10x10 ft flat, paved areas for table & chairs. Large Campfire ring within the patio. Two lovely, Amish garden sheds in excellent condition and loaded with options: 12x16 ft. shed installed in 2010, and a 10x14 ft. shed installed in 2021. Huge 16x18 ft. Raised Deck using long-life Trex engineered planks; custom Pergola over one corner. Deep Shaded, 10 x 12 ft Outer Patio Area with Pergola. Mature Trees for great privacy and shade, especially around property perimeter. Three-level, split rail fence on rear and side yard property lines. (Left-side fence only is owned and maintained by the neighbor.) Extra-Wide Driveway. Paved Parking for 10 vehicles! Also suitable for camping trailer or boat.
Back on the market through no fault of the sellers. Home inspection went well. Two bedroom, one bath townhome with a nice view from the living room/patio area. NEW CARPET in living area/hallway on the main level and upstairs! Looks great! Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio area and the back patio area. New carpet and fresh paint will update this property nicely. Covered storage for bikes/yard toys and more. The townhouse is all electric with a washer/dryer located on the main level. Affordable, and the opportunity to express your own vibe and decorating skills. Call for more information.
$$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$ Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office setup Curb appeal abounds with an inviting brick front and an attached two-car garage. Step inside to find a bright and open main level featuring a cozy fireplace in the great room, a large formal dining area filled with natural light, and a chef's kitchen with abundant cabinetry and high-quality appliances including a wall oven, cooktop, refrigerator, dishwasher, and built-in microwave. Upstairs, retreat to your luxurious primary suite, complete with a tray ceiling, spacious layout, double vanities, soaking tub, and separate shower — a true personal oasis. Three additional bedrooms offer plenty of space for family, guests, or a home office. Enjoy year-round comfort with a two-zone HVAC system, and take advantage of the generous quarter-acre lot for outdoor activities, gardening, or future expansion. Located in the sought-after community of Coventry Farms, this move-in-ready home combines modern convenience with small-town charm. Don’t miss your opportunity to own this beautiful home — schedule your private tour today and start living the Coventry Farms lifestyle!Please use booties provided at the front door. PET FRIENDLY COMMUNITY
Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.
Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.
YOUR DIAMOND IN ROUGH.........Home is original and needs updating through out....Priced to sell. Good bones, will need a buyer with vision. Main level has a large eat in kitchen, living room area and laundry room. Upper level has 3 bedrooms, 2 full bath; including master on suite. Large deck and fenced in back yard. Minutes from The Chester Bridge.
Brand new home in Historic Chestertown available for move-in this October. 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.
Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.
Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedrooms with 1 1/2 baths . It has an open concept on the main floor, kitchen has beautiful white shaker cabinetry, large island, granite countertops, stainless steel appliances, and luxury vinyl flooring. Large covered patio off the kitchen leading out to a spacious back yard. A new shed recently installed for extra storage. Upstairs features 3 good size bedrooms including a large primary suite. If you are looking for a turn key home with new features, then this home is for you.
311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room with a gas fireplace. The home's design features an abundance of natural light due to its 9-foot ceilings and full-height glass walls on the first floor's rear. The sunroom and first floor primary suite access onto the rear deck with the view and privacy of mature trees. There is a primary bedroom suite on each level; and with there being three additional bedrooms, makes a total of five bedrooms or extra rooms for whatever the need may be. The home offers a garage as well as a full unfinished walk-out basement. The pictures prove the true beauty and spaciousness of this home. (room dimensions are approximate)
Newly constructed three-bedroom townhome with all the desired attributes. Fantastic water views from the living level and bedrooms! Spacious open living space with warm hardwood floors and a gourmet kitchen. 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. On the second level you'll find two bedrooms and two bathrooms. There's extra room for an office nook. The third bedroom encompasses the entire third floor and has a great view of the Chester River. You'll enjoy the large back balcony with views of historic Chestertown. The third level could be used as the primary bedroom; there is a large full bathroom and closet. The townhomes have a private driveway, so you'll never worry about finding a parking space. Take advantage of the easy access to Wilmer Park and Chestertown Marina, located just across the street. This townhouse is located in the heart of all Chestertown has to offer! Just a short distance to shops, restaurants, renowned bakeries, and the year-round farmers market by Fountain Park. You will have a front-row seat to the Downrigging Festival! Not to mention the many festivals held in downtown Chestertown throughout the year.
Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by recessed lighting. Step outside to a large deck overlooking a 15,000 square foot lot, perfect for relaxation and entertainment. This home features a playground and tennis court access for leisurely afternoons. With an attached garage, air conditioning, and in-building laundry, convenience is at your fingertips. Water enthusiasts will appreciate the nearby water access, while pickleball fans can enjoy a game on the community court. Situated in a friendly neighborhood, this home combines comfort with a variety of amenities to suit your lifestyle. Whether you’re cozying up by the fireplace or exploring the outdoors, 119 Darden Road is ready to welcome you home!
Motivated Sellers!!! Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a .345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown. Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright living area, a classic dining space, and a large all-seasons room off the kitchen—perfect for gatherings or relaxing year-round. The full basement offers a blank slate, ready to finish as a recreation room, workshop, or extra storage. A brand-new septic system provides peace of mind, while the attached two-car garage and expansive back deck add everyday convenience. Situated on the Queen Anne’s County side of Chestertown, this property keeps you close to the shops, restaurants, and waterfront charm of downtown while offering the privacy of a quiet neighborhood.
Beautifully done! A MUST see! UPGRADED 2023-built Smart Home, tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living spaces, while the laundry room offers added function with quartz surfaces and extra storage. The powder room has been transformed with a stunning vanity and modern fixtures. The second floor offers four spacious bedrooms and two full baths. As a bonus, this property is a smart home, offering comfort and convenience at your fingertips. Just a short drive to multiple marinas in Rock Hall and an easy drive to Philadelphia and Washington, D.C.
Chestertown is located in Maryland. Chestertown, Maryland has a population of 5,557. Chestertown is less family-centric than the surrounding county with 10.61% of the households containing married families with children. The county average for households married with children is 15.86%.
The median household income in Chestertown, Maryland is $44,665. The median household income for the surrounding county is $64,451 compared to the national median of $69,021. The median age of people living in Chestertown is 39.1 years.
The average high temperature in July is 87 degrees, with an average low temperature in January of 25.4 degrees. The average rainfall is approximately 45.1 inches per year, with 13.9 inches of snow per year.
