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$897,000
3 Beds ⋅ 3 Baths
Waterfront Living at the Head of Still Pond Creek Well-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head of Still Pond Creek. Enjoy the best of Eastern Shore living with serene water views, a quiet natural backdrop, and easy access to the Chesapeake bay. Conveniently located with very easy access to Chestertown and points north, this property is ideal as a full-time residence, weekend retreat, or waterfront getaway. A rare opportunity to enjoy comfort, convenience, and the charm of life on Still Pond Creek.

25411 Paradise Point Ln, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$363,000
3 Beds ⋅ 3 Baths
Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and more. With just about an hours drive you can be in Baltimore, Philadelphia or Annapolis. What an opportunity to build instant equity. Spacious home in great community, backing to farmland. This home is located in the community, but not within town limits. Enjoy public utilities without the town tax! Home has been maintained over the years, featuring new HVAC less than a year ago as well as roof replacment 10 years ago. Nicely laid out with living room, dining room, eat in kitchen, laundry room, powder room and great family room on the main level. The second level has a primary suite with loft, two additional bedrooms and hall bath. There is also a nicely proportioned two car attached garage. Home will benefit from updating to make it your own.

206 Maplewood Ln, Galena

Listing courtesy of L. C. Parker Real Estate. Contact:

$649,000
4 Beds ⋅ 3 Baths
Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-new carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home office) shares convenient access to the hall bath. Completing the first floor are a large walk-in pantry and a laundry room outfitted with a brand-new washer and dryer. Upstairs you’ll find two additional spacious bedrooms, each with its own walk-in closet, plus a full bathroom. An oversized walk-in attic provides abundant storage or the perfect opportunity to create a bonus room or extra living space. Dual zone HVAC provides comfort from a newer lower level unit and an upper unit replaced in 2026. Complete roof replacement was completed in 2026 as well. A voluntary HOA opens the door to the amenities of Safe Harbor Great Oak Landing Marina—private beach area, pool, 9-hole golf course, and more. Simply walk or hop in a golf cart to reach the marina and enjoy all the water-oriented lifestyle this community has to offer. You’re also minutes from Rock Hall, with its additional marinas, charter boats, shopping, and restaurants. Less than 10 minutes away lies Chestertown and Washington College, along with more shopping, dining options, a hospital, and a wonderful Saturday morning Farmers Market, and much more. Whether you’re seeking a full-time residence or a relaxing Eastern Shore getaway, this home delivers quality craftsmanship, flexible living spaces, and convenient access to the best of Great Oak Estates and the surrounding area.

22400 Great Oak Landing Rd., Chestertown

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

$455,000
2 Beds ⋅ 2 Baths
Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed off. Outside, you can enjoy the nice-sized yard with the views of a crop field and beautiful sunsets. Located right outside of Chestertown, the home puts shops, restaurants, and the local farmers market close by and is also walking distance to a view of the Chester River! An amazing opportunity to enjoy small-town living convenience, space & character!

7982 Radcliffe Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$750,000
3 Beds ⋅ 3 Baths
Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranquil wooded views. * The generous primary suite features an en-suite bath, while two additional bedrooms makes for flexible bedroom accommodations for family, guests, or a quiet work-from-home office space. A convenient half bath and main-floor laundry round out the practical layout. A full basement offers abundant storage and endless potential for an artist’s studio, workshop, recreation room, or finished expansion. * With its pristine landscaping, mature plantings, and verdant views, this exceptional home is a rare find. And the location is second to none—just minutes from historic downtown Chestertown. Stroll tree-lined streets to discover specialty shops, art galleries, restaurants, and the Saturday Farmers Market at Fountain Park. Washington College, the nation’s tenth-oldest college, anchors the community with year-round cultural events, lectures, and performances. Outdoor enthusiasts will love the nearby Rail Trail, Sultana Lawrence Wetlands Preserve, marinas, and public boat launches providing easy access to the Chester River and Chesapeake Bay. First Friday celebrations, waterfront festivals, and a vibrant arts scene make Chestertown one of the Eastern Shore’s most beloved places to call home.

216 Birch Run Rd, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$480,000
3 Beds ⋅ 3 Baths
PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light. The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space to enjoy your morning coffee or unwind while overlooking the backyard. You'll also find a formal dining room for hosting special occasions, a welcoming living room, and a cozy family room that provides plenty of space for everyday living. Downstairs, the finished basement offers versatile additional living space ideal for a recreation room, home theater, fitness area, playroom, or home office. There is enough space to do all of it. The unfinished area has full laundry and ample storage. Upstairs, the expansive owner's suite serves as a private retreat, complete with a generous walk-in closet and an ensuite bathroom featuring a soaking tub. Two additional bedrooms each offer large closets and ample space for family, guests, or a home office. A full bathroom conveniently located off the second-floor sitting area completes the upper level. Step outside to your own private backyard oasis. The landscaped yard features a refreshing in-ground swimming pool with a new tile finish and a new filtration system, making it ready for years of enjoyment. A new deck with a privacy wall extends from the home, providing the perfect setting for outdoor dining, entertaining, or relaxing poolside. Additional highlights include a large storage shed and a newly installed rock bed surrounding the pool deck that enhances both beauty and low-maintenance landscaping. For added peace of mind, the home also features a roof that is only two years old. Combining spacious living areas, thoughtful updates, exceptional outdoor amenities, and a desirable location in historic Chestertown, this home truly has something for everyone. Don't miss the opportunity to make this exceptional property your next home!

129 Trafford Dr, Chestertown

Listing courtesy of Elevated Real Estate Solutions. Contact: 3024222619
$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 in-ground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. The owners have ordered a new, heavy duty liner, perfect for pets and kids, to be installed with the closing of the pool around the end of September. 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. This home is move in ready! The sellers are selling turn-key with contents. 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:

$1,395,000
4 Beds ⋅ 3 Baths
Beautiful waterfront on nearly 7 acres. Spacious composite deck overlooking Still Pond Creek. Private dock with 3 ft MLW (buyer to verify). Large living room with gleaming hardwood floors and huge sliders looking onto the deck and Still Pond Creek. 2 woodburning fireplaces. Updated kitchen with high-end stainless steel appliances. Laundry room off the kitchen. Steps down to your private waterfront oasis and dock. The lower level features a large family room, 2 bedrooms, a full bath and plenty of storage. This home has that unmistakable Eastern Shore feel. You won't want to miss this spectacular property.

12555 Coopers Ln, Worton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. 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
BIG BUCK FARM * GEESE * DUCKS & GAGGLE OF TURKEYS Hidden away at the end of country lane Privacy awaits Surrounded by woods with a unique mix of fields, water features to enjoy Natures Ever Changing Beauty. 106 Acres Hunting Farm in North East Kent County. Government regulation's insure surrounding farms will remain rather then growing communities. About 60 acres woods, 26 acres of grain fields, with over 7 acres impoundments, deep ponds for fishing plus a wood duck pond in the woods. Impoundments are equipped with water level control. Buyer to verify acreage 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 picturesque views of farm from 2nd floor deck off master bedroom Perfect setting for Canadian geese to spend the nights adding to your enjoyment. Recent Selective Forestry work completed improved opportunity with additional trails and food-lots areas add shelter food for wildlife. 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 you a safe investment that can be enjoyed for generations to come. And surrounding farms protected from becoming communities and ending your dreams. Listed on June 20, 2026 some sites say several years which is not accurate. Featuring Fiber Optic for your Enjoyment and recently install heat pump. Haven’t You Worked Hard? Now Your Time for to Reward Yourself..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. 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:

$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: