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$824,900
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:

$799,000
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
$565,000
3 Beds ⋅ 3 Baths
Light-filled home with glowing wood floors, exposed beams, skylights, and open living space. This one-level home is nestled on just under two acres! The expansive yard offers room for many activities and provides scenic views from the home. Inside, the open living space is bright and airy, with skylights, bay windows, and vaulted ceilings with exposed beams. The large kitchen has beautiful updated granite countertops, a large pantry, kitchen island with seating, and ample cabinet space. From the dining room you can explore the raised deck with a hot tub! Or enjoy meals on the screened porch, finished with water and electricity. This one-level home boasts 3 spacious bedrooms and 2.5 bathrooms. The primary bedroom has a walk-in closet and opens to a sun-filled studio or office space, which has access to the raised deck. There is an attached two-car garage with ample storage space, which could also make a great workshop. Under 15 minutes to downtown Chestertown and less than an hour to Middletown DE. Recent updates include: -Refinished hardwood floors throughout home -Granite countertops in kitchen -Updated kitchen appliances -Water treatment system - & more! Solar leased through Tesla

25124 E Kentfield Rd, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$885,000
5 Beds ⋅ 4 Baths
Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

7680 Country Club Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,495,000
3 Beds ⋅ 2 Baths
ONCE IN A LIFETIME BIG BUCK FARM PLUS GEESE, WOOD DUCKS AND GAGGLE OF TURKEYS Hidden away at the end of country lane Privacy is found Surrounded by woods with a unique mix of fields, water features for your enjoyment of Natures Ever Changing Beauty. Exceptional 106 Acres Hunting Farm in North East Kent County. Approximately 60 acres of woods, 26 acres of grain fields, with over 7 acres impoundments, deep ponds, shallow ponds plus a wood duck pond about 3 acres some are counted as woods. Three of the impoundments are equipped with water level control. Large mouth bass in deep pond. Buyer to verify acreage and acreage breakdown. Impoundments are acres that are dug out, dammed and could be planted with corn. Then before hunting season are flooded with the corn standing. Providing Wildlife total enjoyment for water and feeding including a bubbler on the largest with twin blinds. 1900 farm home renovated about 20 yrs. Ago including new heat pump. Three Bedrooms, 2 Full Baths, Dining Room, Living Room, Family Room with Fireplace. Enjoy the view of the picturesque farm from 2nd floor deck off master bedroom This is the perfect setting for Canadian geese to spend the nights adding to your enjoyment. Snow Geese don’t seam to land as they prefer larger more wide open fields. Some fencing & 4 stalls behind the barn for horses plus a turn in shed. Many nice duck hunting properties are impacted by global warming rising sea level not an issue here. Elevation is well over 50 feet above sea level, so this gives you a safe investment that can be enjoyed for generations to come. Not sure how it happened, listed on June 20, 2026 some sites say several years which is not accurate. Most Recent Improvement Fiber Optic for your Enjoyment and recently install heat pump. Haven’t You Worked Hard? Now Your Time for to Reward Yourself.. Great Location 20 minutes from Middletown, De that offers sales tax free shopping and dining. Wilmington, Towson & Bay Bridge about 50 minutes. Philadelphia and West Chester about 90 minutes. Best Farm Opportunity for the Money Maryland has added rules of the years to project most country properties which is why you don’t see much new construction other then in the towns. And to further restrict nearby growth this property is Almost adjoins the 4,000 Millington Wildlife Preserve. Google it to see what’s available. HERE IS YOUR CHANCE * STEP UP, AND ENJOY A GENERATIONAL TREASURE! Do not enter property without appointment and with Listing Agent.

13235 Knotts, Golts

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$399,000
4 Beds ⋅ 2 Baths
Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, the largest residential lot on Catholic Avenue. This 4-bedroom home was redone from the inside out in 2024. The welcoming living space contains original wood accents, adding much charm to this newly updated home. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT, and engineered hardwood flooring throughout. Three bedrooms, with great closet space, share a full bath. At the end of the home, you'll find the primary bedroom, with a spacious primary bath and walk-in closet. The oversized two-car garage has plenty of room for extra storage. One-floor living and a two-car garage are hard features to find in downtown Rock Hall. Outside, the possibilities are endless; there's ample room for outdoor activities or projects. Updates include: -Crawlspace encapsulation and whole house dehumidifier -10 new windows -New 25 year roof -Siding, shutters & new gutters -New flooring, engineered hardwood, LVT and carpet -Completely updated kitchen with custom cabinetry -HVAC heat pump & AC -200 amp breaker panel And more!

21424 Catholic Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$739,000
3 Beds ⋅ 2 Baths
Two parcels combine for a total of 5.22 acres, offering a rare blend of space, versatility, and opportunity. The separate 3.21-acre parcel is perc-approved and buildable, currently used for hunting, and includes its own right-of-way for private access. The main home sits on 2.012 acres and has been lovingly maintained and thoughtfully updated over the years. Inside, you’ll find a spacious and flexible layout featuring a stunning 24x24 great room—converted from the original attached garage—complete with a gas stove, central air, and seamless flow into the kitchen. Luxury vinyl plank flooring runs throughout much of the home, complemented by stainless steel appliances and numerous system upgrades, including newer windows, roof, well, and septic. Upstairs offers three bedrooms, including a primary suite with an updated bathroom featuring new flooring and vanity. The main level includes a large living room, formal dining area, and a bright kitchen, plus an enclosed sunroom with sliding glass doors that open to a fenced-in, in-ground 15x30 pool—perfect for entertaining or relaxing. The lower level adds even more functionality with an updated full bath, large laundry area, bonus room, and ample storage, along with a new French drain and sump pump system. Outbuildings are equally impressive, including a large shed with kennel and a substantial 36 X 48 pole barn with concrete floors, drain, heat, car lift, 12-foot doors storage in attic, and lean-to—ideal for hobbyists, contractors, or storage of equipment and recreational vehicles. A generator hookup is already in place for added peace of mind. Enjoy excellent hunting opportunities for turkey, deer, and geese, all while being just minutes from the Delaware line. This unique property offers endless possibilities for living, building, and outdoor recreation.

34203 Cypress Rd, Millington

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

$1,395,000
4 Beds ⋅ 4 Baths
Price improvement! Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room and an office. Kitchen with marble countertops and a huge professional refrigerator. Fully finished basement. 2 car attached garage. The first outbuilding is a office space with 2 private offices, a conference room, a gym, kitchenette and half bath. The second outbuilding features 5 garage bays and a finished area that serves as a family room with kitchenette. This property is nothing short of spectacular.

8276 Broad Neck Rd, Chestertown

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

$3,150,000
7 Beds ⋅ 7 Baths
All showings require pre screening and financial capability prior to scheduling any showing. Rarely does a property of this sort come available in Kent County Maryland! This incredible 139+/- acre Chesapeake Bay property is available in it's entirety, however the seller may consider selling the primary residence with a reduced amount of acreage under the right conditions, providing the purchaser bares the cost to do so and is willing to wait the extended period of time to accomplish. The entire property features 72+/- tillable acres, 3900+/- footage of Chesapeake Bay beach frontage, extensive County road frontage, a 3.5 acre waterfowl pond, 2 other smaller ponds, a ten stall horse barn, and caretakers home. A large 33+/- acre flooded area, teeming with waterfowl and deer surrounded by woods runs through the heart of the property. The main residence, designed by architect Paul Rudolf, is perched upon the rip rapped shores of the Chesapeake Bay with endless broad water views. Although the main residence is in need of complete restoration, the site is extraordinary and the salvage reward is potentially significant in dollar value. There is a possibility for construction of a new home on the existing building pad. The hunting and recreational value for this property is enormous! Just imagine family picnics on the sandy beach or spending countless hours searching for sea glass and Indian artifacts while soaking up the sun and listening to the gentle waves roll up on the beach. This property is extremely private, however, convenient to Historic Chestertown, summer fun in Rock Hall, and a short drive to regional airports in Philadelphia, Baltimore and Washington DC. The property is being sold AS-IS, Where-IS and requires 24 hour notice to show with listing agent on site for any and all showings.

6520 Swan Creek Rd, Rock Hall

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$3,150,000
7 Beds ⋅ 7 Baths
All showings require pre screening and financial capability prior to scheduling any showing. Rarely does a property of this sort come available in Kent County Maryland! This incredible 139+/- acre Chesapeake Bay property is available in it's entirety, however the seller may consider selling the primary residence with a reduced amount of acreage under the right conditions, providing the purchaser bares the cost to do so and is willing to wait the extended period of time to accomplish. The entire property features 72+/- tillable acres, 3900+/- footage of Chesapeake Bay beach frontage, extensive County road frontage, a 3.5 acre waterfowl pond, 2 other smaller ponds, a ten stall horse barn, and caretakers home. A large 33+/- acre flooded area, teeming with waterfowl and deer surrounded by woods runs through the heart of the property. The main residence, designed by architect Paul Rudolf, is perched upon the rip rapped shores of the Chesapeake Bay with endless broad water views. Although the main residence is in need of complete restoration, the site is extraordinary and the salvage reward is potentially significant in dollar value. There is a possibility for construction of a new home on the existing building pad. The hunting and recreational value for this property is enormous! Just imagine family picnics on the sandy beach or spending countless hours searching for sea glass and Indian artifacts while soaking up the sun and listening to the gentle waves roll up on the beach. This property is extremely private, however, convenient to Historic Chestertown, summer fun in Rock Hall, and a short drive to regional airports in Philadelphia, Baltimore and Washington DC. The property is being sold AS-IS, Where-IS and requires 24 hour notice to show with listing agent on site for any and all showings.

6520 Swan Creek Rd, Rock Hall

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$499,999
5 Beds ⋅ 4 Baths
Seller is motivated and can move quickly in 30 days! Welcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates multiple outdoor living zones perfect for entertaining, with direct access from the breakfast room. Inside, a light filled two story foyer welcomes you with elegant architectural details including crown molding, chair rail, wainscoting, turned stair railings, and hardwood floors throughout the main level. Neutral paint enhances the home’s timeless appeal. The gourmet kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances (including a French door refrigerator), custom cabinetry, pantry, granite countertops, tile backsplash, and a center island with breakfast bar. The adjoining breakfast room or bonus space, framed by picture windows and a cathedral ceiling, is perfect for morning coffee or hosting holiday celebrations. The main level offers formal living and dining rooms, a convenient powder room, and a spacious family room highlighted by a floor to ceiling stone, wood burning fireplace with raised hearth and custom stone mantel—an inviting gathering space for family and friends. Upstairs, the primary suite is thoughtfully positioned for privacy and boasts double door entry, a walk-in closet plus an additional closet, and a luxurious ensuite bath with dual vanity, soaking tub, and stall shower. Three additional generously sized bedrooms and a full hall bath complete the upper level. The finished walk out lower level expands your living space with a large recreation area, a possible fifth bedroom, full bath with stall shower, a finished bonus room ideal for a fitness area or media room, and an oversized laundry, utility, and storage area with abundant space for seasonal and long-term storage. Conveniently located just minutes from shopping and local dining favorites, and a short drive to Historic Chestertown along the Chester River, you’ll enjoy easy access to charming boutiques, restaurants, galleries, Washington College, and rich cultural and historical attractions.

218 Camelot Dr, Chestertown

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$1,245,500
5 Beds ⋅ 5 Baths
Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland’s most beloved waterfront towns.

105 High St, Chestertown

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