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$425,000
Investment Opportunity Commercial and Mult- Family rentals - The current commercial space is being used for an antique store. Great location on corner lot. The parcels are known as 1502004674 and 1502004666, zoned B-1 and V. The V zoning includes two dwellings offering a total of 3 apartments that are currently rented. The buildings offer a lot of character and charm, just waiting for you next business idea.

26622 Medders Rd, Still Pond

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$325,000
3 Beds ⋅ 1 Baths
A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

896 Washington Ave, Chestertown

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

$325,000
2 Beds ⋅ 2 Baths
Welcome to this beautifully renovated 2-bedroom, 2-bath home sitting on a very large lot. This home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features 2 bedrooms, 2 bathrooms and 1200 square feet. It offers luxury vinyl floors, energy efficient windows, a spacious central island with seating, stainless steel appliances, a large back porch for entertaining and a large plot of land to build on if you wish. Experience the charm of this beautifully renovated colonial home in the heart of Kent County, where classic elegance meets modern luxury. Set on a generous 0.21-acre lot, this detached residence has undergone a major renovation in 2026, ensuring a seamless blend of timeless design and contemporary comforts. Step inside to discover a warm and inviting atmosphere, accentuated by high-end finishes throughout. The spacious layout features two well-appointed bedrooms and two full bathrooms, providing ample space for relaxation and rejuvenation. The heart of the home boasts a state-of-the-art kitchen equipped with a built-in microwave, perfect for culinary enthusiasts and entertaining guests. Natural light floods the interior, highlighting the exquisite craftsmanship defines this property. The exterior, adorned with durable vinyl siding, complements the classic colonial architecture, while the crushed stone driveway offers both functionality and curb appeal. Enjoy the tranquility of your surroundings in this peaceful neighborhood, where you can unwind on your private lot, free from the hustle and bustle of city life. With parking for up to three vehicles, convenience is at your fingertips. This home is not just a place to live; it's a lifestyle choice that embodies comfort, elegance, and sophistication. Embrace the opportunity to make this exquisite property your own and indulge in the luxury of modern living in a historic setting. You will be minutes from downtown Rock Hall, where you can enjoy fresh seafood, explore museums and experience the charm of this Eastern Shore town. Whether strolling along the waterfront, enjoying the marina or setting sail on the Bay, this home puts you at the heart of it all.

21232 Rock Hall Ave, Rock Hall

Listing courtesy of RE/MAX Advantage Realty. Contact: 4104424455
$370,000
3 Beds ⋅ 2 Baths
Quintessential Rock Hall home with an abundance of charm! Located in the heart of Rock Hall, a short distance to Main Street shops, many fantastic restaurants, and seven marinas. Enjoy evenings and mornings on the screened porch, which runs the expanse of the home. Entering from the porch, you'll find a cosy living room and a galley kitchen with open dining space. This home offers a first-floor bedroom and full bathroom, plus two additional bedrooms and a full bath on the second floor. There's a walk-up attic for additional storage, shed in the yard, laundry and utility room off the kitchen. Many updates have been made throughout the years, such as the addition of a copper roof on the front porch, updated bathrooms, flooring, and updated lighting. Recent updates include the home's heating system. Don't miss this downtown gem!

21384 E Sharp St, Rock Hall

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:

$147,000
Build your dream home in Little Neck Farm! Lot #30 is a spacious residential property on Hagy Road with a deeded deep-water boat slip. The future home site offers beautiful pastoral views and is nicely edged with crape myrtles and evergreens. The deeded boat slip, located in the Little Neck community waterfront, is just a short stroll or drive away. The community docks were recently updated and replaced! The deeded boat slip #4 has lights, electric, and water. The waterfront also features space to store and launch a kayak, picnic tables, and a storage shed. Enjoy the peaceful open space and protected shorelines in Little Neck. Peaceful location, yet only 10 minutes to downtown Rock Hall, which offers two small grocery stores, ample shops, restaurants, and festivals throughout the year! This property is a prime location with water access, perfect for a full-time home or weekend getaway.

Lot 30 Hagy Rd, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$935,000
3 Beds ⋅ 3 Baths
This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to serve as base camp for water sports down by the water, dock with direct access to the Chesapeake Bay, barn with a stall for your horse or sheep, and detached 2 car garage with lounge area above. Here you can enjoy the abundance and lifestyle of the Eastern Shore with crabbing, fishing, hunting, water skiing, sailing and hikes on the nature trail all available on site. Outdoor living is huge here with multiple spaces to connect with nature and enjoy the privacy of your own waterfront sanctuary. The home is the perfect size for a weekend getaway or full time residence with a floorplan that has been expanded and opened up to accommodate the amazing views and 2026 lifestyle. Storage is a breeze with a full basement including a shop and rec room for grandkids or guests to go enjoy with privacy. One floor living makes for an easy flow with the primary suite opening to a brick patio with sliders and including both an ensuite bathroom and walk in closet. The blend of amenities on site and proximity to Chestertown's Historic District make this the perfect "magnet house" to attract friends and family or an amazing investment opportunity.

24050 Macs Ln, Worton

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

$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
$385,000
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:

$405,000
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:

$245,000
2 Baths
Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,495,000
3 Beds ⋅ 2 Baths
HIDDEN PARADISE AWAITS AS DEER DAYS OF FALL ALMOST HERE Set your appointment for this 106 Acre Recreational Farm surrounded by woods offers a unique lifestyle for Hunting, Fishing, Horses. Privacy awaits away from the ever increasing congestion of modern day life. 26 ac grain farm plus acres of ponds, impoundments & woods. Hidden away at the end of a small country lane always a special lifestyle for the outdoor lover. BIG BUCKS,, GAGGLE OF TURKEYS, WOOD DUCKS & GEESE. Narrow fields, hedgerows and curved woods giving lots of cover near the ponds and impoundments gives hunting sites spread throughout. Recent Selective Forrest management work has improved the hunt ability offering additional trails and food plot areas. Home was moved approx 20 years siting onto a new foundation then renovated to enjoy the views and ready for its new owners. Horses, we have some fencing, turn in shed, 4 stall to the rear of 3 level barn giving you plenty of room for storage of hay, straw and feed. And think how much fun to ride through and impoundment? Almost adjoins the 4,000 Millington Wildlife Preserve, with riding trails. Remember this area is protected from the surrounding farms becoming communities and the end of your dreams. Haven’t you work Hard all these Years? Reward yourself now with unique Opportunity while it’s available. June 20th 2026 this property came to market. Do not enter property without appointment and listing agent.

13235 Knotts Ln, Golts

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$289,000
3 Beds ⋅ 1 Baths
Charming home located just outside of town, extensively renovated between 2005-2008. Renovations included taking the home down to the studs and updating insulation, drywall, windows, furnace, plumbing, flooring, kitchen, and bathroom. The open floor plan creates a bright and airy living space, and a 2020 addition added a third first-floor bedroom on the main level, offering convenient one-level living. Situated on nearly an acre, the property includes a detached garage/shed and a spacious yard. Water conditioner is owned but not operational, and the dishwasher conveys but is not in connected. Property is being sold As-Is. A small area of wetlands is located in the far rear corner of the parcel.

4818 Piney Neck Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$1,495,000
3 Beds ⋅ 2 Baths
PARADISE AWAITS * BIG BUCK FARM * GEESE * DUCKS AND GAGGLE OF TURKEYS Hidden away at the end of country lane Privacy awaits Surrounded by woods with a unique mix of fields, water features for your enjoyment of Natures Ever Changing Beauty. 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 for fishing plus a wood duck pond in the woods. Three of the impoundments are equipped with water level control. 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 you flood Providing Wildlife total enjoyment for water and feeding if planted. A bubbler on the largest with twin blinds for your desire. 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
$239,900
3 Beds ⋅ 2 Baths
Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!

104 Conley Dr, Chestertown

Listing courtesy of Cummings & Co. Realtors. Contact: 4108230033
$245,000
Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future potential. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$75,000
Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Engineered plans are in place as well as architect plans for a 3 bedroom, 2 bath home. Buyer welcome to use these plans if it fits their needs. Lots of wildlife in the area. Perfect location to build your new home back off the road in a convenient location. Maybe even have your own deer stand! Plat is filed in Kent County Land Records in Plat Book MLM liber1, Folio 391 dated 6/19/1995.

Fairlee Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$85,000
2 Beds ⋅ 1 Baths
Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown’s shops, restaurants, and waterfront, the location can’t be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland’s most beloved small towns. Sold as-is. Cash or renovation loans preferred.

234 N College Ave, Chestertown

Listing courtesy of Cummings & Co Realtors. Contact: (410) 823-0033
$275,000
3 Beds ⋅ 3 Baths
Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCA—blending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car garage offer endless possibilities for a home office, gym, or recreation space. The heart of the home sits on the main level, featuring a generous living room and an eat-in kitchen that opens to a private rear deck—the perfect spot to unwind and look out at the wooded backdrop. Upstairs, you will find three comfortable bedrooms, including a primary suite with a private bath, alongside a dedicated laundry area. Turn-key and low-maintenance, this property is a fantastic opportunity for first-time buyers, downsizers, and investors alike.

104 Acorn Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$1,100,000
Unique opportunity to expand or start your business just minutes from the Eastern Shore thoroughfares of Routes 301 and 213 and also just outside of downtown Chestertown. The blend of infrastructure and zoning such as public sewer, Industrial zoning, tractor trailer access, railway abutting the business park and 3 phase electric throughout the building make this irresistible for a wide variety of businesses. Iconic Eastern Shore architect Peter Newlin designed the building with passive solar heating and cooling in mind as evidenced in the dynamic roof pitch. Radiant floor heating ensures that not only are your employees happy but your machines and materials are better protected as well. The layout allows for great separation of personnel, office tasks, and shop space. 3 Bathrooms, one with shower, allow for the staff to have their space of their own without sacrificing customer experience. Quality control, conference and storage rooms are thoughtfully planned out and spacious. The exterior provides ample parking for staff and customers separately while also designed for tractor trailor turnaround. Over 2 acres and extra sewer allotment allow for vision and future possibilities. Less than 2 hours from Philadelphia, Wilmington, Baltimore, and Washington DC. Opportunities like this don't come up often so jump in now for the growth of the Eastern Shore.

25416 Commerce Ln, Chestertown

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

$765,000
4 Beds ⋅ 4 Baths
Country elegance at its finest with this recently updated and spacious Cape Cod in the water oriented community of Clearview, just minutes from historic Chestertown. The amenities here are a major plus with Franklin pond and community access directly to Churn Creek. The home has had a transformation in the last 2 years with updated bathrooms, floors, kitchen, landscaping, and a new HVAC unit. The main floor master suite allows you to live in luxury with two walk in closets, hardwood double doors, and brand new bathroom with soaking tub and walk in steam shower. Upstairs is a blend of spacious bedrooms and bathrooms galore with an office nook to look out at nature. Storage is no issue with a full basement ready to take on as many holiday decorations as your heart desires. The property is sprawling on over 4 acres that abut the community pond and green space. Outdoor living is celebrated here with a massive deck out back for entertaining and covered front porch for birdwatching. The abundance of our Eastern Shore is just a short ride away with local staples such as Red Acres Hydroponics and Lockbriar Farms for your produce right in Worton and the Chestertown Farmer's Market for the rest. Invest wisely while improving your quality of life.

24274 Waterview Dr, Worton

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

$575,000
1 Beds ⋅ 2 Baths
Welcome to Wymont Park, a sought-after waterfront community on picturesque Still Pond Creek, where every day feels like a vacation on Maryland's Eastern Shore. From sipping your morning coffee while watching the sunrise over the water to enjoying breathtaking waterfront sunsets from your private floating dock, this unique property offers the lifestyle you dream about. Nestled on a beautiful waterfront lot, this versatile property features two separate living spaces, making it ideal for multi-generational living, guest accommodations, or potential rental opportunities. The charming waterfront cottage offers 1 bedroom, 1 full bath, and 1 half bath, highlighted by a spacious living room with cathedral ceilings and panoramic views of Still Pond Creek. The kitchen provides abundant cabinet and counter space, making it perfect for entertaining. Adding even more value is the oversized detached garage with a fully equipped second-floor apartment, complete with 2 bedrooms, a full kitchen, living room, and full bath. Whether you're hosting extended family, accommodating guests, or creating a private workspace, this additional living area offers endless possibilities. Step outside and discover what truly makes this property special. A large wraparound deck leads to a gazebo, creating the perfect place to relax and take in the peaceful creek views. Follow the path to your private floating dock, ideal for boating, kayaking, fishing, crabbing, paddleboarding, or simply enjoying life on the water. Located in one of Kent County's most desirable waterfront communities, this property offers the perfect combination of privacy, natural beauty, and Eastern Shore charm. Whether you're searching for a full-time waterfront residence or weekend getaway, this rare waterfront property is ready for its next owner to make it their own. Don't miss your chance to own a piece of Maryland's Eastern Shore waterfront lifestyle on Still Pond Creek.

25133 Wymont Park Rd, Worton

Listing courtesy of RE/MAX Chesapeake. Contact:

$69,900
Discover the possibilities on this beautiful 4+ acre parcel. Recently surveyed, with water and sewer allocations paid, a value exceeding $16,000! This property offers a rare combination of privacy, recreation, and convenience. Whether you're seeking a peaceful retreat, hunting property, or camping getaway, this versatile parcel offers endless opportunities. Enjoy the tranquility of nature, abundant wildlife, and the privacy of a secluded setting. A small portion near the middle of the parcel is designated as non-tidal wetlands; however, it has never been observed with standing water, even after substantial rainfall.

8886 Georgetown Rd, Chestertown

Listing courtesy of Samson Properties. Contact: 4433178125
$429,900
4 Beds ⋅ 3 Baths
Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot—perfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, you’ll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living.

10781 Fermoy Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$372,000
4 Beds ⋅ 2 Baths
Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other potential uses, with it being right off the kitchen and living room. Out front, you have a cozy front porch, and out from the sliding glass door it opens up to a deck and a good-size backyard. Just pick where you would like to sit for a few and relax. In the back of the yard, you have a new storage shed that is always a plus. Bring your bikes; you will have the perfect streets in this neighborhood to ride and use as you head to the Local Farmers Market. The pictures show this house perfectly. It is in such good condition and has been well cared for and maintained. All ready to move into. It won't disappoint.

213 Byford Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$1,495,000
Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates. The grounds unfold past champion and organic fruit trees, a generous herb garden, an original 18th-century smoke house, two private bridges over Stoneybrook Pond which are all framed by woods and rolling farm fields. Inside, nine bedrooms and six-and-a-half bathrooms reveal nearly two and a half centuries of craftsmanship: original wood floors, brick floors in the dining room and kitchen, signature Bulls Eye moldings, exposed hand hewn beams, eight fireplaces and soaring 11-foot ceilings. For more than 40 years the property has operated as a successful Bed & Breakfast. An optional furniture package is available for a seamless turnkey transition. Its origins as a single-family residence also make it an extraordinary private estate, full-time home or weekend retreat. A coveted sewer allotment is included with the sale which opens the door for a future carriage house, barn, additional dwelling, stable, studio or expanded hospitality use. A new roof, a complete exterior paint job, new hot water heater, new well pump and updated electrical service were completed in 2025–2026. This delivers the rare combination of historic character and modern peace of mind. Tolchester Marina and the Shanty Beach Bar are a mile away. Rock Hall is six miles down the road and the charming historic district of Chestertown is just ten miles away. After nearly four decades of careful stewardship, the current owners are ready to pass on the privilege and the story of The Mitchell House.

8796 Maryland Pkwy, Chestertown

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

$255,000
3 Beds ⋅ 1 Baths
Good as New. Renovated from top to bottom. Pictures say it all. On the outside we have a new roof, windows, and siding . Inside you will not have to do a thing except make it your own. We have all updated painting and flooring throughout the house . You will find Tile and HVLP flooring which are all heated with propane. Kitchen has been updated and freshened up and ready for a new owner. For all your heating and cooling needs we have a New HVAC unit. All of the quality work and updates that have been done will offer peace of mind for years to come. Welcome Home

11106 Plum Dr, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$15,000
Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all due diligence regarding perc testing, building suitability, zoning, utilities, and intended use.

23741 L Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$379,900
2 Beds ⋅ 1 Baths
Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gently sloped backyard to the updated bulkhead at the water's edge. Launch your kayak and explore the river and allow the tide to take you as you explore the river. When done relax indoors to an updated home that offers an open floor plan as the living room and kitchen merge as one. This home was updated several years ago so there is very little you would need to do other than adding your own personal touches. There are 2 bedrooms with wood floors and a single bath. The living room and one of the bedrooms offers access to the rear deck through sliding glass doors. There is a full basement with connecting stairs from the main level. Here is where you will find the laundry. There is plenty of storage space and could possibly be finished living space if the new owner would like to tackle the project. You will be hard pressed to find anything on the water this cute and in this price range so come take a look and decide for yourself!

31673 W Edge Rd, Millington

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$649,900
4 Beds ⋅ 4 Baths
This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the beginning of the surprise you will find in this special, 2,900+/- square foot, home. There are 4 bedrooms, 3.5 baths, a large living room with cathedral ceiling, 2 bedrooms upstairs and 2 bedrooms down, heat pump and mini-split systems for heating and cooling and is move in ready!! A free standing propane stove will help take the chill off during the cooler months. The dining area is just off the kitchen with great views from the large picture window. The kitchen offers all of the major appliances. The laundry room is also a very nice size. There is a side deck for outdoor entertaining. Need storage?.....There is an interior storage/shop room and a large shed to keep some of your summer toys. The crawl space has been recently encapsulated. Need more room or maybe a guest house? The adjoining lot already has sewer and water and is included with the sale. Or just enjoy the open space between you and the next door neighbors. This could make a great full or part time residence! Only a short distance to the harbor and restaurants! Watch the Rock Hall July 4th fireworks right from your deck next year!!

21173 and 21163 Chesapeake Ave, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact: