Chestertown MD Real Estate & Homes for Sale

NEW CONSTRUCTION GETTING READY TO GET STARTED. 8 LOTS TO PICK FROM. 3 BED 2 BATH RANCHER WITH GARAGE. OR BRING THE BUILDER YOUR PLANS FOR A PRICE.

Home located in terrific neighborhood of Quaker Estates, just a few minutes to all the amenities Chestertown has to offer. The home does require some TLC and your personal updates to make it shine again! Large backyard with dog kennels and a wonderful screened-in area under roof for summer entertaining without the weather worries.

Come see, different floor plan than most. Spacious three levels of living with 9 ft. ceilings. Enter into foyer area with welcoming curved staircase. Hardwood flooring in foyer, dining and living rooms. Large open kitchen & breakfast room looking into living with over sized windows offering so much natural lighting. Gracious size master bedroom and bath with sizable walk in closet. Two additional bedrooms on main level. Second floor very open room for your choice of activities with bedroom and full bath. Walk out basement offers some natural lighting with finished off space and full bathroom. Two separate areas for storage and mechanical's. Garage is over sized with utility sink and separate side door. This house has so many options, pretty much has space for everyone and everything. Back yard backs up to trees and protected areas.

This adorable three bedroom home has A LOT to offer! On a desirable street on the Queen Anne's side of 21620, freshly painted throughout, brand new kitchen range, new master bath vanity, private tree-lined lot, spacious rooms, and attached two car garage off of the paved driveway. Move quickly, this home will NOT last!

Location, location, location! Renovated in 2004-2005 this home is a short distance from Washington College, hospital and historic downtown Chestertown! Wood floors throughout the main level. Large master suite. Master bath offers radiant floor heat. Spacious family area on the second level. Tankless propane water heater. House has been used as a rental for the last 12 years and has a "Lead Free" certification.

All new inside and out, freshly finished and ready for you to move in. New roof, windows, siding, gutters, crawl space encapsulated. Original hardwood flooring sanded and stained. New all-wood construction cherry kitchen cabinets. New HVAC, new well, and a HUGE Garage with an attached workshop. Beautifully situated in a peaceful, park-like setting.

Immaculate 3BR/2.5 colonial w/ over 3000 sqft of finished living space in desirable Coventry Farms! Located just outside of Chestertown~s Historic District, this newly renovated home features an open floor plan w/ an abundance of natural light. New eat-in kitchen w/ SS appliances and granite countertops. Spacious bedrooms w/ new flooring and ceiling fan in each BR. Master BR w/ en-suite and walk-in closet. Large fully finished rec room w/ recessed lighting. Attached 2-car garage w/ fully fenced in rear yard and in-ground pool. This home is perfect for hosting family and friends. Nearby is Washington College featuring art, drama, sports, and a lifetime learning center. Welcome to Chestertown, situated close to local Marina~s, downtown Centreville, and the Chesapeake Bay Bridge! Enjoy the many activities Chestertown and the Chester River have to offer! Pool has been professionally closed and winterized.

Located in historic Chestertown, this home was built in 2015 and is gorgeous. Offers upgrades such as wood floors, gas fireplace, open living room/dining room, with an open kitchen. There is a first floor master suite, a laundry room, a screened porch, semi private picket fenced back yard. So much to love about this home! Detached garage with additional storage. There are three bedrooms all today, with threelarge rooms upstairs and a large bath. One of the rooms is a bonus room! Just a short jaunt to all the fun in downtown Chestertown.

Great Ranch home on 1.66 acres in Chestertown, MD. All HUD homes are sold "As Is", #244-16242. All bids through www.hudhomestore.com. This home has 3 bedrooms and 1 bath with original hardwood floors. www.olympusasa-re.com

Very nice rancher in QA Co just minutes from downtown Chestertown. This home features a large LR with gas FP, wood floors, vaulted ceiling & skylights. Separate DR also has wood floors. Spacious kitchen has corian counters and a sunny bay window. A sunroom was added off the LR which leads to a deck. Fully fenced back yard. There is a new heat pump with propane backup and water heater. Pack your bags - this home is move in ready! Photos coming next week.

Investment opportunity! Multi unit in Downtown Chestertown offers 3 units, 1st floor (largest) is a 3 bedroom 1 bath, washer/dryer & has rented for $950/month, 2nd floor is a 2 bedroom 1 bath and has rented for $850 but currently empty & 3rd floor (attic) is a studio (needs work) but can be rented at $450/month. Second floor unit was recently updated in 2018 with a new kitchen, mahogany porch, floors sanded and re-stained, windows sanded down and painted to make lead testing easier, new ceiling and so much more. All units are separately metered and have a great rental history. Make your money back in less then 10 years! If that doesn't interest you, convert it back into a single family home!

Charming cottage style home on the Eastern Shore was built in 2011 and is nestled in the Chestertown Historic District. The convenient location is a a walk away from Washington College, the Chester River Walk, Farmers Market, and downtown Chestertown shops, galleries, restaurants and cafes. Off-street parking and a finished basement with a terrace are among the amenities of this well-cared for home. An open floor plan evokes a casual ambiance. The bright, spacious kitchen has countertop seating and a dining area that opens to the deck and a peaceful view of woods and plantings.

Great rancher in Heather Heights. Easy one floor living. Attached garage. 3 bedrooms, 2 bath. Nice rear deck over looking a great back yard. New carpeting, updated bathrooms, new stainless steal appliances, fresh paint. Close to town.

Great home looking for a new owner! Offers living room and dining rooms with wood floors. The family room and kitchen have access to the rear, partially covered, deck that overlooks the in-ground pool area that is fenced. All bedrooms are on the 2nd floor with some updates to the master bath in recent years. There is a full unfinished basement with connecting stairs and an outside entrance. There is even another detached one door, 20' x 20', garage for lawn equipment or you can make it a workshop! Located in Orchard Hill just minutes from downtown Chestertown.

Enjoy living in Historic Chestertown, short distance to downtown, shopping, and restaurants and the Chester River. Well maintained 3 BR, 1 BA home, enclosed front porch with heat. Nice cozy home for first time homebuyers or investors.

Exceptional architect designed Contemporary residence sited on a 1.8 acre private wooded lot enjoys 190' of protected waterfront, a 110' private dock and 3.5' MLW on Fairlee Creek; one of the prettiest bodies of navigable water in Kent County situated within just 1 nautical mile of the Chesapeake Bay. The property includes three separate living structures: the main house, an office/guest house. and a heated workshop/storage shed that, together, include approximately 3500 square feet of finished living space. The open floor plan interior of the main house features vaulted beaded board ceilings, strategically placed nooks and ledges to showcase art and collectibles, over sized windows and full-view glass doors overlooking the waterfront and easy care radiant heated tile floors. The cooks delight eat-in kitchen features stainless appliances, granite counter-tops, maple Brookhaven cabinetry, above and under-cabinet lighting, a large walk-in pantry, a built-in maple breakfast table, lovely views of surrounding gardens and the waterfront from the sink area through large space-enhancing corner windows and a double sided wood burning fireplace located between the kitchen and the dining area. A spacious private master bedroom and bath area includes a walk-in closet and a master bath with a tiled walk-in shower and Pearl brand whirlpool bathtub. Generously sized windows in the bedroom frame a serene verdant view through the trees to the water . The open living room features large windows and a brick wood-burning fireplace and opens to a screened porch that spans the waterfront side of the house. A 2011 addition includes a spacious cork floored Great Room with an outdoor deck seating area and a separate outdoor entrance. A discreet stairway leads from the Great Room to a bright and airy 2nd level studio that can, alternatively, serve as a third bedroom. A ships ladder stairway leads from the studio/bedroom up into a delightful tower space that offers birds-eye views of Fairlee Creek. An ingenious arrangement of a hallway and hide-away doors connects the Great Room and studio/bedroom to the first floor guest bedroom and bath; enabling use of this whole wing of the house as private guest or live-in quarters with its own private outdoor entrance. Additional main house rooms include a cozy den adjacent to the kitchen, a bright office area with water views and a separate laundry/utility room. The two outbuildings and carport connect to the main house via raised treated-wood walkways. The heated/air conditioned office/guest house includes a large main room, kitchenette, full bathroom and sleeping loft. The workshop includes a large built-in workbench and storage shelving. Rounding out this unique residential compound are a bluestone central courtyard patio, a roofed 2 car carport and a large outdoor equipment storage shed with sliding doors. Lush native and ornamental plant gardens watered with an automated in-ground irrigation system surround the house and point the way to steps leading down to the dock which has electric service. As if all of this isn't more than enough to support a great lifestyle, the property is located in easy walking distance to the Fairlee Creek Public Landing where area residents can easily off-load trailored boats, canoes and kayaks into Fairlee Creek and just a 15 minute drive to both historic downtown Chestertown and the lively waterfront town of Rock Hall. Plus, this property comes with a one year Home Warranty!

An affordable Queen Anne's County waterfront! This property features a newer bulkhead, new BAT septic system, and navigable water. Inside the fully updated ranch home is a new kitchen with custom cabinets, granite counters, stainless steel appliances, new wood floors, a gas fireplace, new Andersen windows, 3 bedrooms and updated bathrooms. Downstairs is a full partially finished basement with a workshop. Enjoy the convenience of being close to Chestertown while utilizing the Queen Anne's County amenities!

PEACE AND QUIET ABOUND AT THIS BEAUTIFUL CAPE COD. ACROSS THE STREET FROM THE CHESTER RIVER, CLOSE TO CHESTERTOWN, COUNTY PARK AND LOCAL POINTS OF INTEREST. (DEEDED R-O-W TO CHESTER RIVER, SUITABLE FOR LAUNCHING KAYAK, CANOE, OR SMALL CRAFT) HOME FEATURES LARGE BEDROOMS, BRAND NEW UPGRADED KITCHEN COUNTER TOP, FRESH PAINT AND NEW CARPET UPSTAIRS. LARGE, LIGHTED DECK FOR RELAXING AND 24 X 32 DETACHED GARAGE BUILT ON 6IN CONCRETE SLAB AND INCLUDES 220 OUTLET FOR THE HOME WORKSHOP, PLUS ADDITIONAL STORAGE SHED. LOOK FOR FUTURE OPEN HOUSE

Located in Country Club Estates, new carpet and fresh paint, this home offers so much. There is a detached 2 car garage, an attached 2 car garage 4/5 bedrooms, a media room, upstairs playroom area, storage galore. The living spaces on the first floor offer loads of space!. A double sided wood burning fireplace, large country kitchen, screened porch, first floor master, a second bathroom on the first floor, you could have three bedrooms on the first floor and 2 on the second. Shows great. Professionally landscaped, the lawn is manicured nicely!. Great curb appeal!

A must see charming renovation in a private setting! The home features 3 bedrooms, 2 full bathrooms, hardwood and ceramic tile floors, efficient geothermal HVAC, a new roof, and hardiplank siding. Improved with a 4 zone home stereo system, horseshoe pit, outdoor shower and detached garage, this home is great for entertainment. Tolchester Marina and the Shanty Tiki Bar are within walking distance making this move in condition property is the perfect full time residence or weekend getaway. The sale includes 3 neighboring lots for a total of .459 acre to secure the private setting.

Seeking Space? Style & Seclusion? No Home to First Sell?? Come Claim this Beauty!! Welcome Home! Nearly 7900 sf of Custom Designed Space Total! With Over 5300 sf above grade, and ANOTHER 2500+ in Walk-Out Bright Basement! 5 Bedrooms, 5 FULL Baths, Large, Open Spaces! Every Upgrade You Could Wish For! Inviting Foyer Opens to Sitting Room, Solarium Flooded w/ Natural Light, Game Room, Dining Room, Main-Level Office w/ Private Entry! 2-Story Family Room Open to Gourmet Kitchen & Morning Room! Upstairs, Master Suite Rivals Most Hotels w/ Sitting Room, Gas Fireplace, His & Hers Walk-in-Closets, Huge Master Bath w/ Separate Shower, Water Closet & Soaking Tub for Two! Each Bedroom Adjoins Full Bath! Basement Boasts Optional 5th Bedroom, Full Bath, Recreation Room, Media Room, Work-Out Room, Storage Space & Walk out Stairs to Fenced Backyard w Inground Pool & Waterfall, backing to Pond! Built to 'Wow' & Entertain, This Beauty Has IT ALL! You Deserve This One! 30 Mins from Bay Bridge, Close to Work & Play! HURRY to This Value, Before It's Your Competition Hosting Pool Parties Here Next Year!! Priced to SELL!

Modern Split Level home To Be Built. Pick your own colors and finishes. Stick built, quality construction. Cathedral ceilings, hardwood floors, granite counter tops, Master Bedroom with attached bath. 2 car garage. Huge lower level for extra living space or bedroom. Peaceful setting. Large lot. Customize to your taste! Stock photos shown, may include upgrades.

Rare (for Kent County) and exceptionally exciting, ultra-contemporary residence is situated on a promontory above twenty-five private pastoral acres. The combination of the position of the main house above the open natural grounds below featuring a breathtaking view of a pond with a "mile-high" fountain, a stream, woods and wildlife. You are on the level of the flight of birds. "Sophistication", "alluring" and extremely "comfortable" are the words that come to mind. The owner has thought of even the most minor detail. One is part of nature and yet is able to enjoy all the amenities of today. This property satisfies the desire for privacy and nature while also offering a lap pool, sauna, exercise area, whirlpool tub, hot tub, expansive windows and multiple level deck. There is an apartment adjacent to carport/garage where caretaker lives but could also be additional guest quarters. After passing through the entrance gates one is enveloped by a feeling of privacy and a sense that you are entering a "very special place".

12.34 TOTAL ACRES, Includes 2 Parcels in Queen Anne's County. Build your own home, hunting, fishing in private stocked pond, opportunities abound. Parcels must be sold together. Value is in the land, home structure is not safe but electric, well, and septic is on-site. Property sold strictly as-is. Second parcel listed separately, see MDQA141824

Great single family ranch located in Heather Heights. Loads of outdoor living space with nearly 1 acre lot, detached 2 car garage and shady enclosed porch ! Many recent updates to baths, flooring, and kitchen. MBR features private MBA with shower. Convenient location to downtown shopping and restaurants as well as the Chester River Yacht and Country Club. Bring the boat and move in !