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$1,125,000

Over half an acre of prime bayfront property! Build a beautiful home on popular Lawton Avenue, the Gratitude neighborhood in Rock Hall. Enjoy sunsets, spectacular views of the bay, and additional views of Swan Creek in back. Spend idyllic afternoons watching the boats sail by! Lawton Ave offers privacy, but is only a short stroll to multiple restaurants, the town beach, and many marinas; there is a private marina just across the street! Town water and sewer is already installed on site. Federal permission has been granted for a 200 ft long, 6 ft wide pier with a T-dock at the end. There would be approx. 5 ft mean low water depth at end of the pier. Buyer to obtain local permits for dock. Survey is available upon request. Two hours, or less, to Philly, South Jersey, Wilmington, Baltimore ad DC. Build your dream home on idyllic Lawton Avenue, on the Chesapeake Bay! *Online tax record does not reflect up to date property acreage.

#2 Lawton Avenue, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$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

$48,000

Come build your dream home. Located right off E Sharp Street on Chesapeake Villa is your .46 acre lot. Location is perfect to everything Rock Hall has to offer, from shops to restaurants to the water. Come check it out today. Lot has water/sewer hookup available, contact town of rock hall to confirm fees.

Sharp St, Rock Hall

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

$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

$375,000

UPDATE - New carpet just installed! Convenient one-level living in this 3BR, 2.5 bath rancher. The house has a desirable split bedroom layout with the primary bedroom, bath & closet off the kitchen and two bedrooms and another full bath off the other side of the house. The sun room has a propane stove and exits to a 12' x 15' deck. There's a 10' x 16' shed. Nice quiet, in-town location.

3 Beds ⋅ 2 Baths

UPDATE - New carpet just installed! Convenient one-level living in this 3BR, 2.5 bath rancher. The house has a desirable split bedroom layout with the primary bedroom, bath & closet off the kitchen and two bedrooms and another full bath off the other side of the house. The sun room has a propane stove and exits to a 12' x 15' deck. There's a 10' x 16' shed. Nice quiet, in-town location.

21336 Haven Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$49,000

Set on just over 1 acre in the Village zoning district, this partially wooded property offers a rare mix of flexibility and possibility. This zoning permits a wide range of uses from single-family, multi-family, and/or townhouses, to short-term vacation rentals, and even certain commercial spaces like restaurants (without drive-thru capabilities), you have room to bring your vision to life. The lot is referenced on Plat MLM5/0194 and is not in the critical area, giving you more freedom in how you design and build. Utility access has already been confirmed with the county: there’s an allocation hookup available. The process according to the county: you must apply for and purchase an allocation which is $16,200, a $50 application fee, and the cost of the water meter (around $600). Connection to the sewer lateral would be handled directly through a plumber but make sure you call the county to verify. What makes this property truly special is its location. Life in Worton is about balance, where the quiet of small town living meets the vibrancy of the Chesapeake just minutes away. Dine on fresh flavors at Watershed Alley or Luisa’s Cucina Italiana, enjoy a casual evening at FairLee’s by the marina, or sip wine and small plates at Casa Carmen. On weekends, you can stroll through Chestertown’s Arts & Entertainment District, catch a show at the Garfield Center, or set sail aboard the Schooner Sultana. For outdoor escapes, Betterton Beach, Eastern Neck Wildlife Refuge, and countless parks and trails offer endless ways to explore the Eastern Shore’s natural beauty. Whether you envision a home, an income property, or a small business, this lot puts you right in the heart of a community that values both tradition and possibility. You’ll find helpful documents and county contact information in the Agent Remarks section of this listing. If you’re unable to access them, feel free to give me a call or text and I’ll be happy to share everything with you directly. You can also use the neighboring property to the right, 24871 Lambs Meadow Road, to get to the address. This lot is to left of their driveway and goes all the way into the woods.

Lambs Meadow Rd, Worton

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$499,999

MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing; keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board; great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.

2 Beds ⋅ 3 Baths

MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing; keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board; great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.

103 Landing Ln, Chestertown

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

$385,000

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

4 Beds ⋅ 3 Baths

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

23043 Bay Shore Spur, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$469,000

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

2 Beds ⋅ 2 Baths

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

21090 W Sharp St Unit #112, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$10,000

HUGE PRICE REDUCTION on a 0.9-acre Vacant land along the Johnsontown Rd, Chestertown, MD and is conveniently located at the corner of Johnsontown Rd and Willow Oak Lane.

Johnsontown Rd, Chestertown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$300,000

Great location - attractive commercial building in popular boating town of Rock Hall. Perfect for professional office, art gallery, yoga studio, retail space. Last used as a florist shop. Beautiful display windows, two bathrooms, a kitchenette area. Gleaming, eye-catching metal roof. Parking for at least 12. A versatile property which provides a dynamic presence in a prime location.

21435 Rock Hall Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$545,000

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

3 Beds ⋅ 2 Baths

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

21090 W Sharp St Unit #133, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact: