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Seller is offering a credit of up to 2% of the purchase price toward the buyer's interest rate buydown with an acceptable offer, a real financial advantage on this updated Cape Cod in the Chesapeake Landing community. Buydown subject to lender approval and buyer qualification. 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.

4 Beds ⋅ 3 Baths

Seller is offering a credit of up to 2% of the purchase price toward the buyer's interest rate buydown with an acceptable offer, a real financial advantage on this updated Cape Cod in the Chesapeake Landing community. Buydown subject to lender approval and buyer qualification. 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:

$319,900

Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout — the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room — tucked away from the main living space so the first floor stays yours. The lot is a third of an acre with a private driveway, giving you real yard on all sides rather than a strip of grass between neighbors. Chesapeake Landing is a waterfront community with a clubhouse, walking trails and community water access. Membership in the community association is voluntary and carries a modest annual fee. Historic Chestertown — the shops, the restaurants, the riverfront — is a short drive away. Everything here is new. New systems, new surfaces, new appliances. Nothing deferred, nothing to renovate, nothing waiting to break in year two. Schedule your private tour today. Photos are of a previously built and sold home in the area and are shown for representation only. Exact finishes, colors, and features of this home may differ.

3 Beds ⋅ 3 Baths

Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout — the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room — tucked away from the main living space so the first floor stays yours. The lot is a third of an acre with a private driveway, giving you real yard on all sides rather than a strip of grass between neighbors. Chesapeake Landing is a waterfront community with a clubhouse, walking trails and community water access. Membership in the community association is voluntary and carries a modest annual fee. Historic Chestertown — the shops, the restaurants, the riverfront — is a short drive away. Everything here is new. New systems, new surfaces, new appliances. Nothing deferred, nothing to renovate, nothing waiting to break in year two. Schedule your private tour today. Photos are of a previously built and sold home in the area and are shown for representation only. Exact finishes, colors, and features of this home may differ.

23208 Buck Neck Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

$269,000

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

3 Beds ⋅ 2 Baths

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

10540 Tonopah Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$260,000

Welcome home to 41 Chartwell! This beautifully updated townhouse in Chesapeake is move-in ready and ready for you to call it home! With over 1300 square feet, the home features three bedrooms and one and a half baths. The 2026 renovation includes fresh paint, new flooring, new windows and appliances. The home comes with, great curb appeal, yard space, and two assigned parking spaces. Enjoy the convenience of a main-floor laundry, along with essential appliances like a dishwasher and garbage disposal, making daily chores a breeze. The exterior has bump-out, secure storage options, while a cozy patio invites you to unwind outdoors. Assigned parking for two vehicles adds to the ease of living. With a low association fee covering common area maintenance and trash, you can focus on enjoying your new home. This property is not just a house; it's a place to create lasting memories. USDA, FHA, and VA Financing available, giving you an opportunity at zero to low down payment options! Conveniently located near major commuter routes, shopping, & dining. Embrace the lifestyle you've been dreaming of in this inviting community! Don’t miss this opportunity—schedule your tour today!

3 Beds ⋅ 2 Baths

Welcome home to 41 Chartwell! This beautifully updated townhouse in Chesapeake is move-in ready and ready for you to call it home! With over 1300 square feet, the home features three bedrooms and one and a half baths. The 2026 renovation includes fresh paint, new flooring, new windows and appliances. The home comes with, great curb appeal, yard space, and two assigned parking spaces. Enjoy the convenience of a main-floor laundry, along with essential appliances like a dishwasher and garbage disposal, making daily chores a breeze. The exterior has bump-out, secure storage options, while a cozy patio invites you to unwind outdoors. Assigned parking for two vehicles adds to the ease of living. With a low association fee covering common area maintenance and trash, you can focus on enjoying your new home. This property is not just a house; it's a place to create lasting memories. USDA, FHA, and VA Financing available, giving you an opportunity at zero to low down payment options! Conveniently located near major commuter routes, shopping, & dining. Embrace the lifestyle you've been dreaming of in this inviting community! Don’t miss this opportunity—schedule your tour today!

41 Chartwell Ct, Perryville

Listing courtesy of Empower Real Estate, LLC. Contact:

$238,000

***Offer deadline tomorrow Sunday, October 18 at 2pm*** Welcome home to Chesapeake Landing! Tucked back in this quiet water-access community, this 3 bed, 1 bath rancher offers 1,008 square feet of easy, low maintenance one-level living on a .37 acre lot with plenty of room to spread out. As you walk into the front door, you enjoy a lovely living space with an open floor plan leading into the kitchen. Down the hall, you have 3 bedrooms and a newly renovated bathroom. This home has been meticulously maintained and updated from top to bottom over the last 4 years including a new roof, new HVAC, new flooring throughout, a water conditioning system, all new stainless steel appliances, a new storm door, and more. There’s so much to enjoy nearby. Launch your boat from the community ramp at Worton Creek Marina and spend the day on the water. Then end it with dinner at a local favorite, The View at Worton Creek. This home is located just a short drive from Chestertown, Rock Hall and the Safe Harbor Marina. Whether you’re buying your very first home or looking for a wonderful rental to add to your portfolio, this one is ready to welcome you. Come see it for yourself!

3 Beds ⋅ 1 Baths

***Offer deadline tomorrow Sunday, October 18 at 2pm*** Welcome home to Chesapeake Landing! Tucked back in this quiet water-access community, this 3 bed, 1 bath rancher offers 1,008 square feet of easy, low maintenance one-level living on a .37 acre lot with plenty of room to spread out. As you walk into the front door, you enjoy a lovely living space with an open floor plan leading into the kitchen. Down the hall, you have 3 bedrooms and a newly renovated bathroom. This home has been meticulously maintained and updated from top to bottom over the last 4 years including a new roof, new HVAC, new flooring throughout, a water conditioning system, all new stainless steel appliances, a new storm door, and more. There’s so much to enjoy nearby. Launch your boat from the community ramp at Worton Creek Marina and spend the day on the water. Then end it with dinner at a local favorite, The View at Worton Creek. This home is located just a short drive from Chestertown, Rock Hall and the Safe Harbor Marina. Whether you’re buying your very first home or looking for a wonderful rental to add to your portfolio, this one is ready to welcome you. Come see it for yourself!

10484 Cogar Rd, Chestertown

Listing courtesy of LPT Realty, LLC. Contact:

$19,000

Spinnaker Road, Chestertown

Listing courtesy of Paul Wesley Real Estate. Contact:

$10,000

Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

Sheldrake Drive, Chestertown

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

$7,700

0.39-Acres in Chesapeake Landing Subdivision *Access to 2 private marinas in the neighborhood * The larger community marina has 36 boat slips with water and electrical service, shower facilities, and a launching ramp. * Potential for public sewer connection in the future. This property is now active in an online auction. All offers must be submitted through the property’s listing page. PLEASE CALL OR EMAIL LISTING AGENT OR BROKERAGE FOR WEBSITE INFO! The sale will be subject to a 5% buyer’s premium pursuant to the Auction Terms and Conditions (minimums may apply). All auction bids will be processed subject to seller approval. RECOMMENDED STARTING BID $7700. PROPERTY WILL BE AUCTIONED MAY 21, 2024 BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

Colfax Rd, Chestertown

Listing courtesy of Meredith Fine Properties. Contact:

$5,000

Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

Kinglet Road, Chestertown

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

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