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$740,000
3 Beds ⋅ 3 Baths
Welcome to your Eastern Shore oasis, an impressive nearly 3,700-square-foot home offering river access on almost 2 acres, a boat slip, stunning water views, and beautifully established grounds surrounded by mature trees. Inside, you’ll find a dramatic two-story foyer, hardwood floors, a designer kitchen with granite countertops and an oversized walk-in pantry, multiple living spaces, a wood-burning fireplace, and an enclosed sunroom overlooking the water. Step outside to the expansive Trex deck with a recessed hot tub, then follow the path directly to the river. With three bedrooms, three full bathrooms, a walkout lower level, two bonus space, and a two-car garage, this home delivers the space, finishes, and lifestyle you’ve been waiting for. Schedule your private tour today and experience this waterfront retreat for yourself. Furniture is available for purchase as well!

14540 Stirrup Lane Ln, Galena

Listing courtesy of Keller Williams Flagship. Contact:

$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:

$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:

$339,900
3 Beds ⋅ 2 Baths
321 West Street in Millington, Maryland is now available for you. This lovely 5-year-old home features vinyl siding, three bedrooms and 2 full bathrooms; Inside, you'll find a formal living room, a dining area, and a fully equipped kitchen with stainless steel appliances, along with a nicely sized island that offers additional space for dining. The main level also includes a laundry room with stackable washer & dryer included. Down the spiral staircase to the ground level you'll discover a one-car garage and a full unfinished basement with daylight windows - perfect for extra storage or future possibilities. Situated on a level rectangular .23 acre lot, this property offers both comfort and potential. Settlement date is negotiable and we kindly ask for a 1 hour prior notice for all showings. This home DOES HAVE an FHA assumable mortgage.

321 West St, Millington

Listing courtesy of RE/MAX Associates - Newark. Contact: (302) 453-3200
$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:

$398,000
3 Beds ⋅ 3 Baths
Warm and Welcoming 3-Bedroom Colonial with a Private Backyard and spacious primary suite. Come home to the comfort and charm of this inviting 3-bedroom, 2.5-bath Colonial, tucked into a peaceful country setting while still offering convenient access to points north. From quiet mornings to busy afternoons and relaxed evenings, this home provides a warm, easy-flowing layout designed for everyday living and time spent together. The spacious primary suite offers a comfortable place to recharge at the end of the day, while two additional bedrooms provide room for family, guests, a nursery, playroom, or home office. With 2.5 baths, the layout makes daily routines easier and helps keep everyone moving smoothly on busy mornings. Step outside to a fenced-in backyard where there is space to play, garden, entertain, or simply enjoy the fresh air in privacy. Blending classic character with a comfortable country feel, this home is a wonderful place to make memories and settle into a lifestyle that feels both peaceful and connected.

200 School St, Millington

Listing courtesy of Gunther-McClary Real Estate. Contact:

$395,000
3 Beds ⋅ 2 Baths
Brand-new construction in the Crosby Woods Subdivision! This beautifully designed 3-bedroom, 2-bathroom home offers comfortable one-level living on a private 0.835-acre lot. The open-concept floor plan features granite countertops, a center kitchen island, pantry, stainless steel appliances, recessed lighting, and a dedicated laundry/utility room. The spacious primary suite includes a tiled private bathroom, while the additional bedrooms provide flexibility for guests, family, or a home office. Enjoy your morning coffee on the front porch or relax on the rear deck overlooking the wooded backdrop. Set back from the road and backing to a protected forest conservation area that cannot be developed, this property offers both privacy and a peaceful setting. Conveniently located just a half mile from the charming waterfront Town of Rock Hall, with its restaurants, marinas, shops, and community events.

21718 Centennial Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$415,000
3 Beds ⋅ 3 Baths
Brand-new construction in the Crosby Woods Subdivision! This thoughtfully designed 3-bedroom, 3-bath home offers convenient one-level living with an open floor plan, recessed lighting, granite countertops, a kitchen island, pantry, and stainless steel appliances. The home features two primary suites with private tiled bathrooms, including one with an additional sitting area for added comfort and flexibility. A dedicated laundry/utility room, welcoming front porch, and rear deck provide both convenience and outdoor enjoyment. Situated on a spacious 0.601-acre lot backing to trees and set back from the road, this property offers privacy while remaining just 0.5 miles from downtown Rock Hall. Don't miss the opportunity to own this beautiful new home!

21712 Centennial Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$468,000
3 Beds ⋅ 2 Baths
Charming Brick Rancher Near the Chester River This custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home... Living Room: Walk along the cobblestone slate path and pass through the new, classic front door into a spacious living room featuring hardwood floors that run throughout the entire house. Dining & Kitchen: A curved archway leads from the living room directly into the dining room. The dining room has an entryway to the kitchen, which could easily be opened up for an even more open feel. Porch: The dining room leads right out to a comfortable porch—the perfect spot to relax and enjoy this nice, quiet neighborhood. Mudroom & Back Entry: An oversized back entry from the breezeway leads into a large mudroom and utility space. Featuring multiple closets and laundry hookups, this functional area offers plenty of space to be creative and fit your family's needs. Bedrooms: The main floor includes three bedrooms with hardwood floors and two full bathrooms Basement: The full basement features an open space with brand-new windows that allow plenty of natural light inside. It is equipped with a new sump pump, offering a perfect blank canvas for storage, a gym, or a rec room. Utilities, Key Updates & Location The house sits on a generous lot with mature landscaping and is connected to well water and public septic. Recent mechanical and structural updates include: Brand-new roof, oil furnace paired with a new HVAC system for efficient heating and cooling. Fresh paint inside and out. You can enjoy beautiful views of the Chester River coming and going from your new home, as well as scenic river views while taking your neighborhood walks. Enjoy the convenience of being just minutes from downtown shopping and dining. Bring your design ideas to update the interior and make it your own!

25750 Collins Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$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:

$650,000
4 Beds ⋅ 2 Baths
Spacious in-town home with coastal charm, just 1 block from the Rock Hall beach on the Chesapeake Bay!  This home offers a luxe front porch, as well as a screened-in porch, perfect for meals and entertaining. The large family room boasts a gas fireplace, built-in shelving, wood ceilings, and a sunny balcony featuring a striped awning.  The eat-in kitchen has updated appliances and ample room; it opens up to the front sitting room. Just around the corner is the light-filled formal dining room. Two first-floor bedrooms share a full bathroom. Two additional bedrooms upstairs share a full bathroom. This home offers the sought after first floor living option, with ample room for guests. There is a two-car garage with interior access and plenty of room for storage, hard to find in Rock Hall.  The outside space has been lovingly landscaped, including a beautiful perennial pollinator garden running the length of the driveway.  This property is move-in ready for the summer! A short distance to the Rock Hall beach, many dining options, ample marinas, and shops. Don’t miss this in-town gem!

20694 Mercer Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$550,000
5 Beds ⋅ 4 Baths
103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and meticulously maintained since – it has ALL the extras: generous breakfast nook bump out, gas fireplace, gleaming hardwood floors, upgraded carpet, oversized windows, granite countertops, stainless appliances, dedicated home office, and a finished basement with a full bath and expansive wet bar. * As you step inside, you’ll be greeted by a two-story foyer flooded with light, dining room and den or family room. The gourmet kitchen that is a chef’s paradise, featuring high-end appliances, custom hardwood cabinetry, and a small island for an ideal triangle of space for meal prep. The open concept layout flows effortlessly into the breakfast nook and living room, providing the perfect setting for family gatherings and celebrations with friends. Click on the propane fireplace for a cozy night watching the sunset or snow flurries outside the tall windows. * The spacious primary suite is an escape through a double door entry – featuring a lighted tray ceiling, a large walk-in closet, en suite bath with soaking tub, glass shower, and a separate water closet. Three additional bedrooms all have custom trim work, generous closets, and large windows. * The finished basement is a standout feature, complete with a stylish wet bar with stone walls that transforms it into the ultimate entertainment zone, perfect for hosting game nights or movie marathons. The backyard feels private with mature trees and a gentle slope, ideal for play space. * The proximity to local parks, playgrounds, restaurants, and shopping ensures that all your family’s needs are met within minutes. Additionally, the Coventry Farms neighborhood fosters a sense of community all while being a convenient distance from Middletown, DE, Philadelphia, PA, Washington DC, Baltimore, MD, and points beyond. * This home is not just a place to live; it’s a lifestyle waiting to be embraced. Don’t miss the opportunity to make this stunning property your own. Schedule your private tour today and experience firsthand what this exceptional home has to offer.

103 Sutton Way, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$540,000
3 Beds ⋅ 3 Baths
Deck was washed and stained on 5/20/26! Built in 2018, this custom coastal raised home is ideally located just one block from the Chesapeake Bay, offering the perfect blend of relaxation, recreation, and investment potential. Enjoy easy access to Rock Hall’s 12 marinas, Ferry Park Beach, local restaurants, shops, and charming downtown—all just a short walk, bike ride, or drive away. Nature lovers will appreciate the close proximity to Eastern Neck Island National Wildlife Refuge, where you can explore by foot, kayak, or bike. Designed for both everyday living and entertaining, the home features an oversized two-car garage with abundant parking—ideal for storing kayaks, paddleboards, bikes, jet skis, and more. The spacious, private backyard sets the stage for gatherings with a fire pit and over 1,000 square feet of wraparound decking invites you to take the party upstairs. A covered porch offers the perfect spot to relax and enjoy summer storms or gentle coastal breezes, and the outdoor shower makes rinsing off after a day on the Bay a breeze. Inside, you’ll find beautiful hardwood floors throughout, generously sized bedrooms, and a thoughtfully designed layout. The primary suite includes dual closets—one being an oversized walk-in—a full en-suite bath with tub/shower combo, and private deck access complete with a TRX workout area. The main living level showcases a bright, open-concept floor plan with stunning 360-degree views, ideal for entertaining. The top level features stainless steel appliances, granite countertops, and walls of windows that flood the space with natural light and capture glimpses of the Bay. Multiple sliding glass doors on every level seamlessly connect indoor and outdoor living, making the expansive decks a true extension of the home. Furnishing will be offered to be purchased making this turnkey, this property also boasts a proven rental history with three years of returning Airbnb and VRBO guests—providing excellent income potential for the weeks you’re not enjoying it yourself. Annual income details available upon request. Don’t miss this exceptional opportunity to own your slice of the Bay lifestyle!

21186 Chesapeake Ave, Rock Hall

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:

$389,000
4 Beds ⋅ 2 Baths
Welcome to Crosby Woods, a charming new community located less than a mile from downtown Rock Hall. This thoughtfully designed neighborhood features just ten single-family homes situated on a quiet cul-de-sac with shared open space and no HOA. This brand-new 2,162 sq. ft. rancher offers comfortable one-level living with four bedrooms and two full bathrooms. The home features beautifully finished tile bathrooms with comfort-height vanities and quartz countertops, combining style with everyday functionality. A one-car garage provides convenient parking or additional storage. Enjoy outdoor living with a covered front deck and a partially covered rear deck—perfect for relaxing or entertaining. Experience the ease of community living on a peaceful street while remaining just minutes from the shops, restaurants, marinas, and waterfront activities of Rock Hall.

21733 Centennial Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$299,900
3 Beds ⋅ 3 Baths
Easy, low-maintenance living in the heart of Rock Hall. New roof, heat, and central air in Spring 2026. This updated 3-bedroom, 2.5-bath townhome with garage is perfectly positioned just steps from marinas, Main Street shops, favorite restaurants, and the community beach. Recent improvements include luxury vinyl plank flooring, newer appliances, new roof, heat, central air, and fresh paint throughout. The entry level offers a flexible bedroom or home office with en-suite bath, while the main living level features a seamless flow from kitchen to dining and family room—ideal for everyday living and entertaining. Upstairs, the primary bedroom boasts vaulted ceilings and a private balcony, alongside an additional bedroom and full bath. The garage provides ideal storage for water toys, fishing gear, or a golf cart. Whether you’re looking for a full-time residence or an easy weekend escape, this home delivers the best of Rock Hall living.

21103 Striper Run, Rock Hall

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$1,459,000
3 Beds ⋅ 3 Baths
**To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, walk-in closets, and doors to the private waterfront deck. Two additional bedrooms share a full bath. the upstairs is complemented by a convenient second-floor laundry. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porch 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 docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach 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.

Little Harbor Way Unit #1, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$499,999
2 Beds ⋅ 3 Baths
MOTIVATED SELLER - BRING OFFERS. 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.

103 Landing Ln, Chestertown

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

$545,000
3 Beds ⋅ 2 Baths
Experience the allure of waterfront living with this stunning condominium, perfectly situated to offer breathtaking views of the Chesapeake Bay and the Rock Hall Harbor. Inside, you are greeted by an inviting ambiance, accentuated by updated kitchen and flooring that seamlessly blend style and functionality. Whether you’re an aspiring chef or simply enjoy the art of entertaining, the modern kitchen is designed to inspire culinary creativity, boasting stainless steel appliances and ample storage space. Just up the stairs you will find two large guest bedrooms, washer and dryer, and a full bathroom. The primary bedroom is located on the third level with a view of the Bay. You'll love the large private balcony overlooking the Chesapeake. The primary bathroom has a soaking tub as well as a shower, and a walk-in closet with ample space for storage. This residence is located a short stroll from marinas, a vibrant array of restaurants, and downtown shops. Easy access to festivals throughout the summer and fall, enjoy a delightful day out or a cozy evening at your favorite eatery. The charm of this location is not just limited to daytime adventures; it transforms into a magical setting at night! The best part is the unobstructed views of spectacular 4th of July fireworks, all from the comfort of your own home. This condominium offers relaxation and convenience while taking in all the charms of Rock Hall. With a focus on comfort, every corner is thoughtfully designed to cater to your needs, blending modern amenities with the natural beauty of its surroundings. Don’t miss the opportunity to make this beautiful condominium your own! Embrace the coastal lifestyle and let the Chesapeake Bay become your new escape.

21090 W Sharp St Unit #133, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact: