easternshoremdfineproperties.com Search Results

$740,000

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!

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:

$565,000

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

3 Beds ⋅ 3 Baths

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

25124 E Kentfield Rd, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$885,000

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.

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:

$935,000

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.

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:

$395,000

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.

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

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!

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:

$1,495,000

DOG DAYS OF SUMMER * DEER DAYS OF FALL ** 106 Acre Property, surrounded by woods offers a unique lifestyle for Hunting, Fishing, Horses. This peaceful setting offers you a chance to forget the ever increasing congestion of modern day life. 26 ac grain farm plus acres of ponds and impoundments and deep woods. Hidden away at the end of a small country lane always a special lifestyle for the outdoor lover. Enjoy natures ever changing natural wonders. BIG BUCKS,, GAGGLE OF TURKEYS, WOOD DUCKS & GEESE All waiting as the snow geese just fly over as the desire larger, open fields, here we have narrow fields, hedgerows and curved woods giving lots of cover near the ponds and impoundments with and hunting sites spread throughout. Home was moved and redone approx 20 years siting on 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. Google what it offers. Haven’t work Hard all these Years? Now is the time to reward yourself with this special offering. Some says this property has been listed for years. That is incorrect. Listed June 20th of this year This is your chance, to find your Generational setup. Don’t let it slip away… Do not enter property without appointment and listing agent.

3 Beds ⋅ 2 Baths

DOG DAYS OF SUMMER * DEER DAYS OF FALL ** 106 Acre Property, surrounded by woods offers a unique lifestyle for Hunting, Fishing, Horses. This peaceful setting offers you a chance to forget the ever increasing congestion of modern day life. 26 ac grain farm plus acres of ponds and impoundments and deep woods. Hidden away at the end of a small country lane always a special lifestyle for the outdoor lover. Enjoy natures ever changing natural wonders. BIG BUCKS,, GAGGLE OF TURKEYS, WOOD DUCKS & GEESE All waiting as the snow geese just fly over as the desire larger, open fields, here we have narrow fields, hedgerows and curved woods giving lots of cover near the ponds and impoundments with and hunting sites spread throughout. Home was moved and redone approx 20 years siting on 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. Google what it offers. Haven’t work Hard all these Years? Now is the time to reward yourself with this special offering. Some says this property has been listed for years. That is incorrect. Listed June 20th of this year This is your chance, to find your Generational setup. Don’t let it slip away… Do not enter property without appointment and listing agent.

13235 Knotts Ln, Golts

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$1,495,000

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

3 Beds ⋅ 2 Baths

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

13235 Knotts, Golts

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$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:

$765,000

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.

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:

$25,000

One acre in Betterton with the beach and boat ramp just a few blocks away! While this lot could be buildable, one would have to build a bridge across a stream to access by vehicle and public utilities while available would need to be run out there as well. Priced as recreational land for the nature enthusiast, occasional tent camper, or hunter.

Third Ave, Betterton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$374,900

Location is EVERYTHING. Upgrades are EVERYTHING. And this stunning Rock Hall home offers BOTH. Perfectly positioned in the heart of Rock Hall, Maryland, this beautifully upgraded home delivers the coastal lifestyle buyers are searching for on Maryland’s Eastern Shore. Imagine hopping on your golf cart or bike and being just minutes from waterfront restaurants, marinas, local shops, live music, and all the charm that makes downtown Rock Hall one of the Eastern Shore’s most beloved waterfront towns. And let’s talk about the upgrades… because they absolutely blow new construction away. From the moment you walk through the door, you’ll notice the difference. The level of craftsmanship, custom finishes, thoughtful details, and high-end touches throughout this home are the kind buyers WANT but rarely get from a builder at this price point. Simply put, you will NOT find these upgrades in new construction without spending significantly more. The stunning kitchen is the heart of the home, featuring upgraded finishes, custom details, and a layout designed perfectly for entertaining and everyday coastal living. Every space throughout the home feels warm, inviting, and move-in ready with details that immediately stand out. Whether you’re searching for a full-time residence, weekend getaway, vacation home, Airbnb investment opportunity, or second home near the Chesapeake Bay, this property checks every box. -High-end upgrades throughout -Stunning kitchen with custom finishes -Spacious layout designed for entertaining -Move-in ready with luxury details throughout -Golf cart or bike ride to marinas, restaurants, and downtown Rock Hall -Minutes to waterfront dining, boating, and the Chesapeake Bay -The perfect blend of location, lifestyle, and luxury upgrades Homes with THIS location and THIS level of upgrades rarely hit the market in Rock Hall… and when they do, buyers move FAST. If you’ve been searching for a beautifully upgraded home in Rock Hall, Maryland with close access to marinas, boating, waterfront restaurants, and Chesapeake Bay living, this is the one you do not want to miss.

3 Beds ⋅ 3 Baths

Location is EVERYTHING. Upgrades are EVERYTHING. And this stunning Rock Hall home offers BOTH. Perfectly positioned in the heart of Rock Hall, Maryland, this beautifully upgraded home delivers the coastal lifestyle buyers are searching for on Maryland’s Eastern Shore. Imagine hopping on your golf cart or bike and being just minutes from waterfront restaurants, marinas, local shops, live music, and all the charm that makes downtown Rock Hall one of the Eastern Shore’s most beloved waterfront towns. And let’s talk about the upgrades… because they absolutely blow new construction away. From the moment you walk through the door, you’ll notice the difference. The level of craftsmanship, custom finishes, thoughtful details, and high-end touches throughout this home are the kind buyers WANT but rarely get from a builder at this price point. Simply put, you will NOT find these upgrades in new construction without spending significantly more. The stunning kitchen is the heart of the home, featuring upgraded finishes, custom details, and a layout designed perfectly for entertaining and everyday coastal living. Every space throughout the home feels warm, inviting, and move-in ready with details that immediately stand out. Whether you’re searching for a full-time residence, weekend getaway, vacation home, Airbnb investment opportunity, or second home near the Chesapeake Bay, this property checks every box. -High-end upgrades throughout -Stunning kitchen with custom finishes -Spacious layout designed for entertaining -Move-in ready with luxury details throughout -Golf cart or bike ride to marinas, restaurants, and downtown Rock Hall -Minutes to waterfront dining, boating, and the Chesapeake Bay -The perfect blend of location, lifestyle, and luxury upgrades Homes with THIS location and THIS level of upgrades rarely hit the market in Rock Hall… and when they do, buyers move FAST. If you’ve been searching for a beautifully upgraded home in Rock Hall, Maryland with close access to marinas, boating, waterfront restaurants, and Chesapeake Bay living, this is the one you do not want to miss.

21124 Striper Run, Rock Hall

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$549,000

Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation at a great price. This property also provides for a perfect multigenerational household. The garage is another amazing plus with a kitchenette, full bathroom and loft for a private office or area for grandkids to roughhouse. Surround yourself with a great sense of community and bucolic farm landscapes. The rear yard includes a hot tub, amazing hardscaping for family gatherings and a view that opens out to peaceful farm fields. Sit in the sunroom at 12712 Still Pond Road and truly understand the quality of life that comes with country living. This is one not to be missed.

6 Beds ⋅ 6 Baths

Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation at a great price. This property also provides for a perfect multigenerational household. The garage is another amazing plus with a kitchenette, full bathroom and loft for a private office or area for grandkids to roughhouse. Surround yourself with a great sense of community and bucolic farm landscapes. The rear yard includes a hot tub, amazing hardscaping for family gatherings and a view that opens out to peaceful farm fields. Sit in the sunroom at 12712 Still Pond Road and truly understand the quality of life that comes with country living. This is one not to be missed.

12712 and 12714 Still Pond Rd, Still Pond

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

$549,000

Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation at a great price. This property also provides for a perfect multigenerational household. The garage is another amazing plus with a kitchenette, full bathroom and loft for a private office or area for grandkids to roughhouse. Surround yourself with a great sense of community and bucolic farm landscapes. The rear yard includes a hot tub, amazing hardscaping for family gatherings and a view that opens out to peaceful farm fields. Sit in the sunroom at 12712 Still Pond Road and truly understand the quality of life that comes with country living. This is one not to be missed.

12712 and 12714 Still Pond Rd, Still Pond

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

$427,000

Tucked away on a peaceful 0.47-acre lot surrounded by trees, this custom-built contemporary home offers the kind of privacy and natural beauty that’s hard to find. From the moment you arrive, it feels like your own private retreat. Inside, the open floor plan is filled with warmth and character, featuring exposed beams, rich hickory flooring, and beautiful wood accents throughout. Skylights and expansive windows bring in natural light and showcase the ever-changing scenery just outside—whether it’s wildlife passing through or the quiet beauty of the woods. The kitchen is truly the heart of the home, designed with both function and gathering in mind. Custom solid cherry cabinetry with soft-close doors and drawers, a spacious walk-in pantry, and an oversized island with seating, shelving, and a propane cooktop make it as practical as it is inviting. A charming bay window over the sink offers the perfect view of the backyard. Just steps away, the screened porch and private deck create seamless indoor-outdoor living—ideal for morning coffee, entertaining, or simply unwinding in the peaceful surroundings. The first-floor primary suite offers comfort and convenience, complete with its own private deck, walk-in closet, and a spa-like bath featuring a soaking tub and separate shower. Upstairs, you’ll find two additional bedrooms, a full bath, and a versatile loft space perfect for a home office, reading nook, or play area. Built with efficiency and quality in mind, the home features Structural Insulated Panels (SIPs) for enhanced insulation and comfort, along with a conditioned crawl space with concrete flooring and lighting for easy-access storage. A generator adds an extra layer of peace of mind. Located in a quiet rural setting with access to Herringtown Creek, you’re also just minutes from Rock Hall—known for its charming restaurants, marinas, shops, and waterfront at Ferry Park. For even more outdoor exploration, Eastern Neck National Wildlife Refuge is just a short drive away. If you’ve been dreaming of a home that offers privacy, comfort, and a true connection to nature, this one is worth experiencing in person. One year home warranty included!

3 Beds ⋅ 2 Baths

Tucked away on a peaceful 0.47-acre lot surrounded by trees, this custom-built contemporary home offers the kind of privacy and natural beauty that’s hard to find. From the moment you arrive, it feels like your own private retreat. Inside, the open floor plan is filled with warmth and character, featuring exposed beams, rich hickory flooring, and beautiful wood accents throughout. Skylights and expansive windows bring in natural light and showcase the ever-changing scenery just outside—whether it’s wildlife passing through or the quiet beauty of the woods. The kitchen is truly the heart of the home, designed with both function and gathering in mind. Custom solid cherry cabinetry with soft-close doors and drawers, a spacious walk-in pantry, and an oversized island with seating, shelving, and a propane cooktop make it as practical as it is inviting. A charming bay window over the sink offers the perfect view of the backyard. Just steps away, the screened porch and private deck create seamless indoor-outdoor living—ideal for morning coffee, entertaining, or simply unwinding in the peaceful surroundings. The first-floor primary suite offers comfort and convenience, complete with its own private deck, walk-in closet, and a spa-like bath featuring a soaking tub and separate shower. Upstairs, you’ll find two additional bedrooms, a full bath, and a versatile loft space perfect for a home office, reading nook, or play area. Built with efficiency and quality in mind, the home features Structural Insulated Panels (SIPs) for enhanced insulation and comfort, along with a conditioned crawl space with concrete flooring and lighting for easy-access storage. A generator adds an extra layer of peace of mind. Located in a quiet rural setting with access to Herringtown Creek, you’re also just minutes from Rock Hall—known for its charming restaurants, marinas, shops, and waterfront at Ferry Park. For even more outdoor exploration, Eastern Neck National Wildlife Refuge is just a short drive away. If you’ve been dreaming of a home that offers privacy, comfort, and a true connection to nature, this one is worth experiencing in person. One year home warranty included!

22300 Frazier Rd, Rock Hall

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$128,000

This nice wooded lot on Crosby Rd is 0.2 mile to Long Cove Marina and Long Cove County Landing. Rock Hall Yacht Club is just up the road on McKinleyville Rd. With 142 ft of road frontage and a wooded buffer, there's lots of privacy and room to roam. Included in the price is a 2-hour consult with a licensed architect to design your dream home. The property is near navigable water, but not in the flood plain. Winter water views are possible. There's a public sewer allocation and hook up is available. Well water is needed. There is a recorded plat and the uplands of the lot was previously delineated.

Crosby Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$55,000

Welcome to 5120 Eastern Neck Road—an exceptional opportunity to own a .50-acre homesite just outside the charming waterfront town of Rock Hall. Perfectly positioned for both privacy and convenience, this property offers the ideal setting to bring your vision to life in a peaceful, coastal-inspired setting. This lot features an existing public water and sewer allocation already in place, offering added convenience as you plan your future build. This rare advantage saves both time and upfront costs, allowing you to focus on designing the home you’ve always imagined. Whether you envision a coastal retreat, full-time residence, or a weekend escape, this homesite is ready to accommodate your dreams. Enjoy the best of Eastern Shore living with easy access to marinas, waterfront dining, boutique shops, and local parks, all just minutes away. Spend your days boating, fishing, or simply soaking in the laid-back charm that makes Rock Hall such a sought-after destination. The property is located within a Critical Area and Flood Zone, so buyers are encouraged to consult with Kent County Government regarding specific building guidelines and requirements—ensuring your plans align seamlessly with local regulations. Opportunities like this—with utilities already in place, a prime location, and endless potential—don’t come along often. Bring your builder, your vision, and start creating your perfect Eastern Shore escape today!

5120 Eastern Neck Rd, Rock Hall

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$515,000

Amazing waterfront community on the Sassafras river. This Kentmore Park cottage was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect get away or primary residence. Well maintained. Four bedrooms and two baths. One bath reconfigured with stack washer and dryer. Could be returned to full bath when relocating washer and dryer to basement. Lovely pastoral view of farmland. Easy path to beach and central Kentmore Park area. Tax free shopping in Delaware. Convenient shopping in Galena. Check out Cross Street Market for produce, local meat, specialty foods, plantings and friendly faces. Explore Jones Farm for local meats and ice cream. Event space for special occasions, pumpkin patch and seasonal surprises. Convenient Sassy Market for deli, fresh meat and the perfect snacks and beverages. Galena has fine and casual dining, pizza and delicious steak sandwiches. You are close to Historic Chestertown with casual and special dining, eclectic shopping, Chestertown Golf and Country Club, waterfront access, fishing and boating opportunities. Cruise the Chester River on the Packet for an adventure or special celebration. Visit historical buildings. Enjoy weekend activities in History Park in the center of town, farmers market, Tea Party, Crazy Days sales and more. Never a dull moment. Chestertown is full of history including Washington College and the Chestertown Tea Party Reenactment. This home offers so much not to mention lazy days on the beach, water sports, friendly and welcoming neighbors, gathering at the pier for taps and the sunset. Living the Life! Kentmore Park was established in the late 1940 era. Started mainly as a sailing community for weekend and summer enjoyment. Now a very active community with year round social events as many familys have expanded their time in Kentmore beyond spring, summer and fall. A mix of full time and part time residents. All ages are represented. There is a social club with $350.00 yearly dues. There are many activities with the Kentmore Park Improvement Association (KPIA) for all ages. Easy travel to points north and south. PA, NJ, DC. Easy day trip to Annapolis, Easton, St. Michaels.

4 Beds ⋅ 2 Baths

Amazing waterfront community on the Sassafras river. This Kentmore Park cottage was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect get away or primary residence. Well maintained. Four bedrooms and two baths. One bath reconfigured with stack washer and dryer. Could be returned to full bath when relocating washer and dryer to basement. Lovely pastoral view of farmland. Easy path to beach and central Kentmore Park area. Tax free shopping in Delaware. Convenient shopping in Galena. Check out Cross Street Market for produce, local meat, specialty foods, plantings and friendly faces. Explore Jones Farm for local meats and ice cream. Event space for special occasions, pumpkin patch and seasonal surprises. Convenient Sassy Market for deli, fresh meat and the perfect snacks and beverages. Galena has fine and casual dining, pizza and delicious steak sandwiches. You are close to Historic Chestertown with casual and special dining, eclectic shopping, Chestertown Golf and Country Club, waterfront access, fishing and boating opportunities. Cruise the Chester River on the Packet for an adventure or special celebration. Visit historical buildings. Enjoy weekend activities in History Park in the center of town, farmers market, Tea Party, Crazy Days sales and more. Never a dull moment. Chestertown is full of history including Washington College and the Chestertown Tea Party Reenactment. This home offers so much not to mention lazy days on the beach, water sports, friendly and welcoming neighbors, gathering at the pier for taps and the sunset. Living the Life! Kentmore Park was established in the late 1940 era. Started mainly as a sailing community for weekend and summer enjoyment. Now a very active community with year round social events as many familys have expanded their time in Kentmore beyond spring, summer and fall. A mix of full time and part time residents. All ages are represented. There is a social club with $350.00 yearly dues. There are many activities with the Kentmore Park Improvement Association (KPIA) for all ages. Easy travel to points north and south. PA, NJ, DC. Easy day trip to Annapolis, Easton, St. Michaels.

14136 Kentmore Park Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$625,000

It is a rare opportunity for a private waterfront lot off the Sassafras River to come available. This 14 acre parcel of land is located above the bridge in a well established small community of Gentle Winds. Scenic and tranquil area for birding watching, kayaking or taking a short boat ride to restaurants located down the river. With this 14 acre lot, there are open areas and woods to play with. Build the house of your dreams and be able to work and play where you live. Short drive to tax free shopping in Middletown DE.

14200 Metasequoia Ct, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$415,900

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.

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

$226,000

Welcome to this sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knight’s Landing surrounded by beautiful farmland. It’s the perfect spot if you’re looking for peaceful living without feeling far from everything—just under five minutes to the local high school, community center, and park. Cozy, convenient, and easy on the budget, this home offers small-town vibes with everyday essentials close by. Seller is offering a $5,000 credit to the buyer !! Property sold AS- IS Seller will make NO REPAIRS

3 Beds ⋅ 2 Baths

Welcome to this sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knight’s Landing surrounded by beautiful farmland. It’s the perfect spot if you’re looking for peaceful living without feeling far from everything—just under five minutes to the local high school, community center, and park. Cozy, convenient, and easy on the budget, this home offers small-town vibes with everyday essentials close by. Seller is offering a $5,000 credit to the buyer !! Property sold AS- IS Seller will make NO REPAIRS

25044 Travis Trl, Worton

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

$95,000

Welcome to Wilson Point Estates! A 14 Lot Custom Home Eastern Shore Community. Designed for those who value craftsmanship and intention, Wilson Point Estates is not a production neighborhood, it’s a place where each home is purposefully designed to complement the character of the Shore. Picture gracious porches, elevated coastal details, and interiors tailored to how you truly live, entertain, and unwind. The setting offers easy access to the Sassafras River, nearby marinas, and the charm of historic Galena and Chestertown. Perfect for boating days, waterfront dining, and peaceful evenings close to home. Whether you’re building a primary residence or an Eastern Shore retreat, this location delivers both serenity and convenience. All homes within the community are guided custom builds. Buyers may bring their own architectural plans for approval or work directly with the development’s design team to create a home uniquely their own. Construction Concierge by Conestoga manages the development, design coordination, and architectural review, ensuring a seamless and elevated building experience from start to finish. This listing is for Lot 2, located on Sassafras Cove Road. Home is TO BE BUILT. LOT PRICE is $95,000.00. Listing Photos depict possible models to be built. For full details on the homesite, design guidelines, and custom building process, contact Construction Concierge by Conestoga at 410.512.6800. This is more than a lot—it’s the foundation for a lifestyle defined by timeless design, thoughtful living, and the best of the Eastern Shore. Images are artist renderings and AI generated for marketing purposes only. Finishes, features, and details are subject to change. House is to be built, Concierge Homes is the Builder.

2 Sassafras Cove Rd, Galena

Listing courtesy of Patterson-Schwartz Real Estate. Contact: 4108851606

$3,150,000

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

7 Beds ⋅ 7 Baths

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

6520 Swan Creek Rd, Rock Hall

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

$15,000

Half acre+ secluded wooded lot. There used to be a house on the property but county does not have well or septic records so buyer would need to perform perc test to build. There appears to be electric run to lot and there is a 16' right of way to access. Buyer to do any due diligence. Could be a great hunting property surrounded by woods and farmland!

22681 Wood Yard Ln, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$3,150,000

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

7 Beds ⋅ 7 Baths

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

6520 Swan Creek Rd, Rock Hall

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

$813,900

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing 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! 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.

3 Beds ⋅ 4 Baths

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing 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! 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.

104 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$839,500

**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing 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! 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.

3 Beds ⋅ 3 Baths

**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing 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! 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.

102 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$80,000

The last buildable lot in the Cheerful Echoes neighborhood is perc approved and ready for improvement. NO HOA! With a gentle slope and plenty of room for the backyard of your dreams, a walkout lower level can open to a patio, gardens, etc... you name it! Just a few miles from the Worton Community Center and the walking trails at Worton Park, and a convenient drive to Chestertown, Middletown, and points beyond.

Still Pond Creek Rd, Worton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$10,000

Build Your Dream Home on Two Expansive Lots in Chesapeake Landing! 15,000 SQFT of prime land combining Lots 191 & 192 on the south side of Clarissa Road, Block 2 of Chesapeake Landing, all under one tax ID. This is a rare opportunity to design and build your custom home in a sought-after community where nearby homes are selling in the high $600Ks! Enjoy the charm of Chestertown living, just minutes from Historic Downtown Chestertown, the scenic Chesapeake Bay, and Washington College. Conveniently close to local parks, restaurants, and waterfront amenities, this location combines tranquility with accessibility. Don’t miss this incredible chance to secure your lot and bring your dream home to life. Opportunities like this don’t come often—act now and make your vision a reality!

Clarissa Rd, Chestertown

Listing courtesy of Samson Properties. Contact: (703) 378-8810

$305,000

The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single-family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck .Chestertown is a quaint, historic district on the Eastern Shore with an avid art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front foot fee of $15,000 that can be paid off with installments, annually over 15-20 years. The driveway of 10971 is an easement. The property line of 11037 goes beyond the driveway of 10971. See photos and site plan. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

3 Beds ⋅ 2 Baths

The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single-family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck .Chestertown is a quaint, historic district on the Eastern Shore with an avid art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front foot fee of $15,000 that can be paid off with installments, annually over 15-20 years. The driveway of 10971 is an easement. The property line of 11037 goes beyond the driveway of 10971. See photos and site plan. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

0 will be 11037 Bottom Rd, Worton

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000