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$415,000
3 Beds ⋅ 3 Baths
Beautifully updated and maintained Colonial home in Dogwood Village. This spacious home offers nearly 2000 square feet of living plus a basement area. There is an attached 2 car garage and both a screened porch and open deck at the rear of the home. A fireplace in the living room adds warmth to cool fall and winter days. The rear of the home is accented by both spacious screened porch and an open deck. Perfect location with easy access to highways and tax free shopping in Middletown.

189 Birchwood, Galena

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

$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:

$325,000
3 Beds ⋅ 2 Baths
136 N Main St is Coming Soon in Galena! Your next home may be closer than you think. This inviting Colonial combines classic character with thoughtful updates across nearly 1,900 square feet of living space. Inside, you'll find three comfortable bedrooms, one full bath upstairs, a convenient main-level half bath, a bright kitchen with an easy flow into the main living areas, and a dedicated laundry/mudroom that adds everyday convenience. Outside, the fully fenced backyard offers exceptional space to enjoy, complete with mature shade trees, a fire pit, a storage shed, and plenty of room for outdoor gatherings, gardening, pets, or play. A large paved driveway provides abundant off-street parking. Conveniently located near Rt. 301, Chestertown, Middletown, local marinas, shopping, and dining, this home offers the charm of small-town living with easy access to everyday essentials. Stay tuned, you'll want to be among the first to see it when it hits the market.

136 N Main St, Galena

Listing courtesy of Keller Williams Legacy. Contact: 4436609229
$325,000
2 Beds ⋅ 2 Baths
Welcome to Rigbie Bluff, where coastal charm meets modern comfort. This rare furnished 2-bedroom, 2-bath end-unit top floor condominium offers panoramic views of the upper Chesapeake Bay and Sassafras River, a deeded boat slip with boat lift, and exceptional community amenities. Situated on the third floor and perfectly positioned to capture abundant southern sunlight, this move-in-ready residence features sliding glass doors in both the living room and primary bedroom, opening to a spacious waterfront covered balcony that spans the entire rear of the unit. Enjoy spectacular views of sailboats, yachts, and passing ships while relaxing from the comfort of your home. The bright, open-concept interior includes an updated kitchen with new appliaces, tile backsplash and composit counter-tops, New luxury vinyl plank flooring throughout the home. Outside, residents enjoy easy access to the community's saltwater pool, private pier, and some of the area's finest waterfront recreation. The deeded boat slip, on the deep end of the dock and included boat lift provide immediate access to the Chesapeake Bay and surrounding waterways. A large private storage area on the lower level, complete with its own separate entrance, offers ample space for kayaks, bicycles, boating equipment, or a workshop. The unit also includes a reserved parking space directly in front, along with abundant guest parking nearby.Recent condominium association improvements include comprehensive exterior siding replacement, foundation and deck repairs across all five buildings, installation of dock ice-breaker pilings, conversion of the community pool to saltwater, and replacement of the wood walkways.Ideally located within walking distance of Betterton Beach, a renowned waterfront restaurant, public tennis courts, and a playground, this property provides the perfect setting for both year-round living and weekend escapes. Explore historic waterfront towns, nature parks, and countless rivers, creeks, and coves throughout Maryland's Eastern Shore from your own waterfront retreat.Whether you're seeking a full-time residence, vacation home, or boating getaway, this exceptional Rigbie Bluff condominium delivers comfort, convenience, and breathtaking Chesapeake Bay views.

10 Ericsson Ave Unit #32, Betterton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3023515000
$449,000
3 Beds ⋅ 2 Baths
COMING SOON - NEW ROOF!!! Your Chesapeake Bay getaway just steps from Haven Harbour South Marina. Launch your boat, dine on the waterfront, stroll to the beach, and enjoy resort-style living from this beautifully updated home. This updated 3-bedroom, 2-bath rancher situated on an expansive lot with glimpses of the water and room to relax, entertain, and enjoy the Eastern Shore lifestyle. The spacious detached garage provides ample storage for vehicles, boats, and recreational equipment. Unwind in the cooled three-season room overlooking the fenced backyard, offering the perfect setting for gatherings with family and friends after a day on the water. Ideally located just a short walk or golf cart ride from Haven Harbour South Marina, you'll enjoy convenient access to boat slips, waterfront dining, a sandy beach, marina amenities, and breathtaking Chesapeake Bay sunsets. Whether you're seeking a year-round residence, weekend escape, or boating retreat, this property offers comfort, convenience, and the best of Rock Hall living. Wake up, walk to your boat, spend the day on the Chesapeake Bay, enjoy waterfront dining, watch the sunset, and return home to relax in your private backyard. Every day feels like you're on vacation.

21120 Green Ln, Rock Hall

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. 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:

$275,000
3 Beds ⋅ 1 Baths
Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in the kitchen. Has an additional coat closet as you come in the side door and a separate pantry. Nice open back yard. A solid house in proximity to town. Good place to make your own and call home, or an investment.

956 Washington Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. 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:

$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:

$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
$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:

$415,900
3 Beds ⋅ 2 Baths
REDUCED!! Nestled in the charming Betterton community, this delightful farmhouse-style home offers a perfect blend of rustic charm and modern comfort. With 3 spacious bedrooms and 1.5 bathrooms, the interior features warm wood flooring and a cozy brick fireplace, creating an inviting atmosphere for gatherings. The attic provides additional storage or potential for creative use, while the partial basement adds practicality to your living space. Set on a generous 3.75-acre lot, this property boasts a serene backdrop of trees and open spaces, ensuring privacy and tranquility. Enjoy panoramic views of the surrounding woods, perfect for nature lovers and those seeking a peaceful retreat. The outdoor space is ideal for gardening, play, or simply unwinding in the fresh air. Located in a rural setting, this home is just a short walk from local amenities, including r Betterton beach and boat ramp. The community is known for its friendly atmosphere and strong sense of belonging. Public services are readily available, ensuring convenience and peace of mind. This property is not just a house; it's a place to create lasting memories. Embrace the lifestyle that Betterton offers, where comfort meets community. Lot does have subdivision possibilities. Check with the town manager.

201 Ericsson Ave, Betterton

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$389,000
3 Beds ⋅ 3 Baths
REICE REDUCED!! Completely renovated from the studs up, this beautifully updated 3-story home offers 2,200 square feet of thoughtfully designed living space just outside of Rock Hall. Featuring 3 spacious bedrooms and 3 full bathrooms — one on each level — this home provides flexibility and comfort for everyday living or guests. The open-concept main floor showcases luxury flooring, brand-new stainless steel appliances, and abundant natural light throughout. A convenient rear mudroom leads to a covered porch. Upstairs, you’ll find generously sized bedrooms with large windows, while the third floor offers an additional expansive sitting area — perfect for a home office, media room, or bonus living space. Brand-new carpeting adds warmth and comfort to the upper levels. The current owners have incorporated thoughtful upgrades and modern features throughout, making this home truly move-in ready. Enjoy the charm of Rock Hall living with the benefit of a fully updated home just minutes from town, marinas, restaurants, and waterfront attractions.

6416 Edesville Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$469,000
2 Beds ⋅ 2 Baths
Back on the market. Spectacular Chesapeake Bay waterview condo located in the heart of Rock Hall. Beautiful upgrades include LVP flooring, tile bathrooms, kitchen cabinets, backsplash, granite countertops and appliances, plus new electric fireplace. Relax on the recently refinished Bayview deck or cuddle up next to the fireplace. The convenience of condo living lets you enjoy all the festivals and fun Rock Hall has to offer without the maintenance headaches. This unit has been used as a high quality short term rental for more than a year.

21090 W Sharp St Unit #112, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. 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: