SELLERS OFFERING $5,000 IN CLOSING COST CREDIT IF UNDER CONTRACT BY END OF FEBRUARY. HIGHLY MOTIVATED - DON'T MISS THIS OPPORTUNITY! This historic 1916 home is charming inside and out. They dont build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and a short stroll to downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests. Gorgeous original heart-pine hardwood floors and beautiful molding run throughout. The mahogany-floored porch has interchangeable screens and windows, easily converting from a screen porch into a sunroom. New 6 pressure-treated pine fence provides privacy in the backyard, perfect for children or pets to enjoy. Adjacent to the fence, the lot also has a driveway with off-street parking for two vehicles. Calling those with green thumbs - a separate fenced garden is ready for your flowers, fruits, and veggies to be planted this spring! In summer 2025, owners completed $60,000 in updates, including a new roof and fully updated electrical wiring as well as fresh interior paint. (As the electrician noted, much to his chagrin, this house is SOLIDLY built - plaster walls were difficult to get through - and have since been professionally patched!) All upgrades were intended to be enjoyed by current homeowners, but they are regretfully moving to be closer to a new job. After updates, home appraised for over $500,000. Instant equity for a lucky buyer!
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 â??Meyersâ? 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.
Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard - your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season and a true haven for butterflies and hummingbirds. You will delight in an outdoor sitting area under a lovely shade tree. The main level features gleaming hardwood floor, a semi-open floor plan with a cozy fireplace perfect for cool evenings, and abundant natural light that creates a calming atmosphere throughout. The large primary suite offers comfort and convenience, and there is the option for a second bedroom on the main level. Current owners have opted to make that room a large office, and it features two closets. The kitchen is a dream - spacious enough for a large island and a generous breakfast area that easily fits a full-sized table. There is a mural border that shows scenes of historic Chestertown. Pantry and plenty of storage. Upstairs, youll find two large bedrooms and a full hall bath, ideal for guests or loved ones. Each bedroom offers walk-in storage - no attic ladders needed! Solar operated fans keep the attic spaces cool. Additional highlights include leased solar panels which have been paid out, a large garage with ample storage, additional storage shed with electric and water. , and a fantastic location just minutes from the Chester River and the Chester River Yacht and Country Club. Two zone for heating and cooling. Come see this charming home for yourself - its the perfect blend of beauty, comfort, and thoughtful design!
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.
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! The right wing of the house has two bedrooms and a full bathroom. The left wing has the master bedroom that includes a spacious full bathroom, and walk-in closet. With the recent price change, this property now offers an exceptional opportunity-whether youre looking for a primary residence, a weekend retreat, or a vacation home on Marylands 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!
Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring 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. You'll love the warm hardwood floors throughout the home. 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.
*Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn. Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury countertops and a sunroom bump-out with ample natural light-ideal for morning coffee, reading, or cozy dinners. Upstairs, the spacious primary suite offers a true retreat with a walk-in closet, en suite bathroom, and the convenience of an upstairs laundry room. The fully finished basement adds exceptional versatility, featuring its own private entrance, kitchenette, full bath with steam sauna, and open-concept living/bedroom area-perfect for guests, or entertaining. A dedicated workroom completes the lower level, ready for projects or hobbies. Outside, enjoy your fenced-in backyard oasis complete with a deck. This home has been meticulously cared for and thoughtfully updated, including: New roof, gutters, and gutter covers (2025) New HVAC system - furnace and A/C (2024) New 80-gallon water heater (2022) Fully renewed basement (2022) with new flooring, carpet, paint, and dual sump pumps Finished garage (2022) Ornamental Fence (2020) Furnishings Negotiable .
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 youll 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 Chestertowns most historic locations.
Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impressed by this stunning ranch home that has undergone a complete, top-to-bottom renovation! Offering 1800 sq. ft. of newly renovated finished interior space, this property is much bigger than it looks and provides true move-in ready convenience with zero deferred maintenance. Upgrades Inside & Out! Enjoy peace of mind knowing the entire house has been meticulously updated with major systems and aesthetic finishes, including: Exterior: New Roof, New Siding, New Windows, and a crisp, modern look. Mechanicals: Brand New Heater, New Central A/C, New Plumbing, New Electrical Service, and a New Hot Water Heater. Interior Finishes: New Flooring and fresh, tasteful New Paint throughout. The heart of the home is the all-new, open-concept kitchen, perfect for entertaining and daily life: New Cabinets, Granite Countertops, Tile Backsplash, Stainless Steel Appliance Package. The fully renovated bathroom shines with a new tub/shower featuring elegant tiled walls and floor, new fixtures, and a stylish new vanity. A separate, dedicated laundry room within the house provides excellent convenience and extra storage space, a powder room or second full bath could be easily added to this room as well. The versatile layout includes a second living area that can easily be utilized as a Fourth Bedroom or a dedicated Home Office, adapting to your needs. Out back, you'll find: A beautiful Paver Patio for outdoor dining and relaxation. Plenty of room for parking. A Large, Detached Two-Car Garage is a massive bonus! The garage has its own new roof, siding, windows, electric, and new electric doors, making it perfect for a workshop, home business, hobbyist, or simply superior storage. Don't lift a finger-simply turn the key and start living! This is an unparalleled opportunity for a like-new home in a great Fairlee location. Note: Seller is a licensed Maryland Realtor. Schedule your showing today!
Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring reclaimed pine flooring, private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. New irrigation system to all flower beds. New paint inside and out. House has had major remodels in 2000 and 2020. Town sewer. Not far from town, but the property has a private feel. Come and be amazed!!
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.
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.
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. Dont 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
NO HOA OR FRONT FEES: Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that features a peninsula island with a breakfast bar and cabinetry that offers ample storage and workspace including a separate pantry. Off from the kitchen is a room overlooking the back yard that offers access to the back yard. The primary suite is privately located in rear of home being complete with shower stall, tub, large vanity as well as a linen closet. The two additional bedrooms are located on the opposite wing of home offering separation. The finished basement is quite a highlight with a six-foot glass walk-out door onto the large rear private patio that overlooks an open wooded area that features mature trees, flowering shrubs and perennials. The pleasure of seeing deer and wild turkey stroll through and the morning sound of birds offers a peaceful retreat. Now to come back inside the basement, you will find it amazing. The main room coming in is very large being open to a kitchenette. The large room having a gas fireplace is presently used as a game room. The game room opens to a sitting room with half-bath access. There are additional rooms in the basement that includes a large workshop and another sizable room that could be used as a theatre room, work-out room or for whatever the need may be. The stairs from the basement up into the main level includes a chair lift. The home has a generator and solar panels for energy efficiency, as well as a yard sprinkler system and soaker hoses to keep the landscaping looking its best. This home being located in the historic town of Chestertown offers convenience to the Chester River, cultural festivities, waterfront parks, rail-trail, The Farmers Market, YMCA, hospital, shops and Washington College. The public record reflects the main level being 2135 SF with the lower level being 1800 S.F.
**Price increase due to the homes expanded footprint-over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest suite. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area-perfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry. Designed with future needs in mind, this home also offers the option of a residential elevator for effortless access across all levels. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include two docks, pool, grilling and outdoor dining area right on the water, large firepit, area to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.
Welcome to this charming 3-bedroom, 2-bath rancher offering comfortable one-level living in the desirable Chester Harbor community. Set on a spacious 0.76-acre lot on the Queen Annes side of the Chester River, this home is nestled in a water-oriented neighborhood-ideal for boating enthusiasts and nature lovers alike. Inside, youll find a generously sized primary bedroom featuring a private en-suite bath with a walk-in shower and an impressive walk-in closet complete with a cedar section for added warmth and storage. The kitchen and dining area showcase newer flooring installed just two years ago, creating a modern and inviting space for everyday meals and gatherings. Updated appliances add both style and functionality to the kitchen. Stay cozy and energy-efficient during cooler months with the wood stove, and enjoy comfortable summers with large window units that effectively cool the home. Outside, the fenced yard-installed just four years ago-offers a secure and spacious area perfect for children and pets to play and explore. A detached two-car garage provides ample storage for vehicles, tools, or all your boating and water toys. This inviting property combines comfort, convenience, and a sought-after waterfront lifestyle-an excellent opportunity to enjoy life near the Chester River.
