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Spectacular Water View Home nestled at the tip of Eastport Peninsula between Spa Creek, Back Creek and the Severn River in the premiere gated community of Chesapeake Landing, with onsite Yacht Club and pool memberships available. 21 Chesapeake Landing embodies the epitome of Eastport’s waterfront lifestyle. The Maritime Republic of Eastport is a vibrant waterfront community deeply rooted in both sailboat racing and pleasure boating traditions. Residents treasure the walkable lifestyle, with more than 50 restaurants, pubs, boutique shops, and historic City Dock and Downtown Annapolis just steps away. This immaculately-maintained home has been thoughtfully designed with meticulous, high-level upgrades, resulting in a seamless blend of elegance, comfort, and timeless design. A private in-law, guest suite or entertainment room on the ground level adds to the homes versatility. On the main level, expansive sliding glass doors open onto one of three decks; an ideal setting for savoring water views, or simply relaxing with evening libations. It’s also a front-row seat for the 4th of July, New Year’s Eve fireworks displays and the annual Blue Angels Airshow. The daily parade of sail and power boats, regattas, navy vessels and pirate ships is a spectacular bonus that makes this home truly unique. At the heart of the home is a spectacular chef’s kitchen: An oversized center island invites casual gatherings, while custom cabinetry, complete with artful display nooks, add depth and functionality. Sleek stainless-steel appliances pair beautifully with the honed-granite countertops, to provide ample prep space for the most discerning gourmet. A private deck just off the kitchen is perfectly positioned for effortless outdoor grilling. The open-concept layout is both flexible and inviting. Island seating flows naturally into the adjacent dining area, which overlooks the living room and captures water views beyond. Rich, gleaming hardwood floors span the main, bedroom, and loft levels, adding warmth and sophistication throughout. The living room is a true retreat, enhanced by 9-foot ceilings and a gas fireplace that adds instant ambiance with the flip of a switch. Upstairs, wake up to enjoys water views of Annapolis Harbor and the Severn River. The graciously sized owner’s suite welcomes you with dramatic vaulted ceilings and abundant natural light. The recently renovated spa-inspired ensuite bath is a sanctuary in itself, featuring a glass-enclosed shower and soaking tub that doubles as a steam room complete with folding chairs for relaxation and the therapeutic benefits of a sauna. Dual vanities, high-end fixtures, and generous storage, all finished in calming, modern tones complete the experience. Two additional bedrooms offer versatility and comfort; ideal for guests, family, or as a dedicated art studio, home gym, or private home office. The ground-level living space adds even more flexibility. Featuring its’ own paver patio and private entrance, a full bath and a custom kitchenette—including a refrigerator, sink, microwave, built-in storage and neutral tile flooring. This area can be completely closed off from the rest of the home, making it a perfect in-law suite, private guest quarters or family entertainment area. Additional amenities include a one-car garage, an extra driveway parking space, a large paver patio, and the freedom to lock, leave, and travel with peace of mind. Outside your front door, the Eastport lifestyle unfolds. Take a leisurely stroll to local waterfront restaurants, pubs, and boutique shops. Catch a water taxi to historic downtown Annapolis, or launch your kayak or paddleboard from nearby Horn Point Beach Park. Eastport offers the charm of a coastal village with the energy of a thriving maritime hub, just across Spa Creek from the U.S. Naval Academy and all the culture, history, and amenities of downtown Annapolis! Don't Miss The Opportunity to Make This Your Home!

4 Beds ⋅ 4 Baths

Spectacular Water View Home nestled at the tip of Eastport Peninsula between Spa Creek, Back Creek and the Severn River in the premiere gated community of Chesapeake Landing, with onsite Yacht Club and pool memberships available. 21 Chesapeake Landing embodies the epitome of Eastport’s waterfront lifestyle. The Maritime Republic of Eastport is a vibrant waterfront community deeply rooted in both sailboat racing and pleasure boating traditions. Residents treasure the walkable lifestyle, with more than 50 restaurants, pubs, boutique shops, and historic City Dock and Downtown Annapolis just steps away. This immaculately-maintained home has been thoughtfully designed with meticulous, high-level upgrades, resulting in a seamless blend of elegance, comfort, and timeless design. A private in-law, guest suite or entertainment room on the ground level adds to the homes versatility. On the main level, expansive sliding glass doors open onto one of three decks; an ideal setting for savoring water views, or simply relaxing with evening libations. It’s also a front-row seat for the 4th of July, New Year’s Eve fireworks displays and the annual Blue Angels Airshow. The daily parade of sail and power boats, regattas, navy vessels and pirate ships is a spectacular bonus that makes this home truly unique. At the heart of the home is a spectacular chef’s kitchen: An oversized center island invites casual gatherings, while custom cabinetry, complete with artful display nooks, add depth and functionality. Sleek stainless-steel appliances pair beautifully with the honed-granite countertops, to provide ample prep space for the most discerning gourmet. A private deck just off the kitchen is perfectly positioned for effortless outdoor grilling. The open-concept layout is both flexible and inviting. Island seating flows naturally into the adjacent dining area, which overlooks the living room and captures water views beyond. Rich, gleaming hardwood floors span the main, bedroom, and loft levels, adding warmth and sophistication throughout. The living room is a true retreat, enhanced by 9-foot ceilings and a gas fireplace that adds instant ambiance with the flip of a switch. Upstairs, wake up to enjoys water views of Annapolis Harbor and the Severn River. The graciously sized owner’s suite welcomes you with dramatic vaulted ceilings and abundant natural light. The recently renovated spa-inspired ensuite bath is a sanctuary in itself, featuring a glass-enclosed shower and soaking tub that doubles as a steam room complete with folding chairs for relaxation and the therapeutic benefits of a sauna. Dual vanities, high-end fixtures, and generous storage, all finished in calming, modern tones complete the experience. Two additional bedrooms offer versatility and comfort; ideal for guests, family, or as a dedicated art studio, home gym, or private home office. The ground-level living space adds even more flexibility. Featuring its’ own paver patio and private entrance, a full bath and a custom kitchenette—including a refrigerator, sink, microwave, built-in storage and neutral tile flooring. This area can be completely closed off from the rest of the home, making it a perfect in-law suite, private guest quarters or family entertainment area. Additional amenities include a one-car garage, an extra driveway parking space, a large paver patio, and the freedom to lock, leave, and travel with peace of mind. Outside your front door, the Eastport lifestyle unfolds. Take a leisurely stroll to local waterfront restaurants, pubs, and boutique shops. Catch a water taxi to historic downtown Annapolis, or launch your kayak or paddleboard from nearby Horn Point Beach Park. Eastport offers the charm of a coastal village with the energy of a thriving maritime hub, just across Spa Creek from the U.S. Naval Academy and all the culture, history, and amenities of downtown Annapolis! Don't Miss The Opportunity to Make This Your Home!

21 Chesapeake Lndg, Annapolis

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

Selling Office: Coldwell Banker Realty.

$1,525,000

Spectacular water-view home nestled at the tip of the Eastport Peninsula in coveted Chesapeake Landing, a premier gated community. Set within the vibrant Maritime Republic of Eastport, deeply rooted in sailboat racing and pleasure-boating traditions. 23 Chesapeake Landing offers an exceptional blend of comfort, convenience and the Annapolis waterfront lifestyle. Residents treasure the neighborhood’s walkability, with an array of restaurants, pubs, boutiques, historic City Dock and Downtown Annapolis just steps from your door! Take a water taxi across Spa Creek to downtown or lauch a kyak or paddleboard from nearby Horn Point Park. Well maintained and freshly painted, this thoughtfully designed end-unit townhome, providing an abundance of natural light is equally suited to relaxed everyday living and effortless entertaining. The kitchen features sleek stainless-steel appliances, granite countertops, custom cabinetry and abundant storage. A casual dining area encourages relaxed gatherings, while the adjoining deck is perfectly positioned for outdoor grilling. Overlooking the living room and the water views beyond, the separate dining room provides an elegant setting for more formal occasions. The inviting living room is enhanced with taller ceilings, hardwood flooring and a wood-burning fireplace that adds warmth and ambience during the cooler months. Expansive sliding glass doors, fitted with plantation shutters, open to one of three newly rebuilt and expanded decks providing an ideal setting for savoring the water views or relaxing with your favorite beverage. This remarkable vantage point also provides front-row views of Fourth of July and New Year’s Eve fireworks, the annual Blue Angels Airshow and the ever-changing parade of sailboats, powerboats, regattas, naval vessels and the occasional pirate ship. The generously sized owner’s suite welcomes you with dramatic vaulted ceilings, abundant natural light, an en-suite bath and a private deck for even more water viewing pleasure. A second bedroom, full bath and laundry area complete the bedroom level. The loft level offers tremendous flexibility and may be adapted as additional bedroom space, a home office, art studio, fitness room or whatever best complements your lifestyle. The ground floor level, warmed by a second fireplace and enhanced by updated luxury vinyl plank flooring provides additional comfortable living space with exceptional flexibility, including its own private entrance. A full bath provides the perfect setup as an additional guest suite. French doors open to a private patio overlooking the beautifully landscaped grounds. Designed for easy lock-and-leave living, this home allows you to travel with peace of mind. The Annapolis Maryland Capital Yacht Club owns and manages the marina, pool and clubhouse. For the boating enthusiast, marina slips available for lease provide easy access to the Chesapeake Bay and its many waterfront destinations including use of the pool and clubhouse. Just outside your door, The Maritime Republic of Eastport combines the charm of a coastal village with the energy of a thriving maritime community - all just across Spa Creek from the U. S. Naval Academy and the culture, history and amenities of downtown Annapolis. Don't miss an opportunity to make this exceptional Eastport residence your home!

3 Beds ⋅ 4 Baths

Spectacular water-view home nestled at the tip of the Eastport Peninsula in coveted Chesapeake Landing, a premier gated community. Set within the vibrant Maritime Republic of Eastport, deeply rooted in sailboat racing and pleasure-boating traditions. 23 Chesapeake Landing offers an exceptional blend of comfort, convenience and the Annapolis waterfront lifestyle. Residents treasure the neighborhood’s walkability, with an array of restaurants, pubs, boutiques, historic City Dock and Downtown Annapolis just steps from your door! Take a water taxi across Spa Creek to downtown or lauch a kyak or paddleboard from nearby Horn Point Park. Well maintained and freshly painted, this thoughtfully designed end-unit townhome, providing an abundance of natural light is equally suited to relaxed everyday living and effortless entertaining. The kitchen features sleek stainless-steel appliances, granite countertops, custom cabinetry and abundant storage. A casual dining area encourages relaxed gatherings, while the adjoining deck is perfectly positioned for outdoor grilling. Overlooking the living room and the water views beyond, the separate dining room provides an elegant setting for more formal occasions. The inviting living room is enhanced with taller ceilings, hardwood flooring and a wood-burning fireplace that adds warmth and ambience during the cooler months. Expansive sliding glass doors, fitted with plantation shutters, open to one of three newly rebuilt and expanded decks providing an ideal setting for savoring the water views or relaxing with your favorite beverage. This remarkable vantage point also provides front-row views of Fourth of July and New Year’s Eve fireworks, the annual Blue Angels Airshow and the ever-changing parade of sailboats, powerboats, regattas, naval vessels and the occasional pirate ship. The generously sized owner’s suite welcomes you with dramatic vaulted ceilings, abundant natural light, an en-suite bath and a private deck for even more water viewing pleasure. A second bedroom, full bath and laundry area complete the bedroom level. The loft level offers tremendous flexibility and may be adapted as additional bedroom space, a home office, art studio, fitness room or whatever best complements your lifestyle. The ground floor level, warmed by a second fireplace and enhanced by updated luxury vinyl plank flooring provides additional comfortable living space with exceptional flexibility, including its own private entrance. A full bath provides the perfect setup as an additional guest suite. French doors open to a private patio overlooking the beautifully landscaped grounds. Designed for easy lock-and-leave living, this home allows you to travel with peace of mind. The Annapolis Maryland Capital Yacht Club owns and manages the marina, pool and clubhouse. For the boating enthusiast, marina slips available for lease provide easy access to the Chesapeake Bay and its many waterfront destinations including use of the pool and clubhouse. Just outside your door, The Maritime Republic of Eastport combines the charm of a coastal village with the energy of a thriving maritime community - all just across Spa Creek from the U. S. Naval Academy and the culture, history and amenities of downtown Annapolis. Don't miss an opportunity to make this exceptional Eastport residence your home!

23 Chesapeake Lndg, Annapolis

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

Selling Office: EXP Realty, LLC.

$1,499,000

Experience elevated water oriented living in this beautifully updated four-level luxury townhome offering tranquil Severn River views and a rare sense of privacy within one of Eastport’s most coveted gated communities. Recently refreshed from top to bottom, this home features brand-new decks with contemporary cable railings, a new A/C unit and heat pump, fresh interior paint, and a new rear privacy fence—blending modern comfort with timeless sophistication. The main level welcomes you with an open, sun-filled layout that flows effortlessly from the gourmet kitchen—complete with Bosch stainless steel appliances, granite countertops, larger center island and custom cabinetry—to the dining and living areas framed by expansive glass doors leading to a spacious deck overlooking the water. Rich hardwood flooring, recessed lighting, and a sleek built-in entertainment unit with beverage refrigerator create a polished yet inviting atmosphere perfect for entertaining. Upstairs, discover a large guest bedroom with vaulted ceilings and the primary suite that offers a private balcony with serene river views, dual closets, and a spa-inspired bath featuring a soaking tub, separate frameless shower with dual shower heads and bench seating, and dual vanities. The top-level private loft/ bonus room features an open skylight with great panoramic views of Annapolis and cedar closet that provides ample space for family or guests while the private lower-level bedroom with an en-suite bathroom and a walkout patio is perfect for visitors or a quiet home office. Additional features include an oversized 1-car garage with extended driveway and ample additional parking within the community, custom storage systems, integrated blinds, and meticulous craftsmanship throughout. Enjoy a lifestyle of sophistication and ease- walk to Eastports waterfront restaurants, local pubs, and marinas, or simply relax on your private balconies with front-row views of the Blue Angels flyovers, the Parade of Lights, Annapolis’ summer fireworks, and the city’s celebrated boat shows. Residents also enjoy optional membership access to the on-site marina and pool—available to join for an additional cost—offering resort-style amenities just steps from your door.

4 Beds ⋅ 4 Baths

Experience elevated water oriented living in this beautifully updated four-level luxury townhome offering tranquil Severn River views and a rare sense of privacy within one of Eastport’s most coveted gated communities. Recently refreshed from top to bottom, this home features brand-new decks with contemporary cable railings, a new A/C unit and heat pump, fresh interior paint, and a new rear privacy fence—blending modern comfort with timeless sophistication. The main level welcomes you with an open, sun-filled layout that flows effortlessly from the gourmet kitchen—complete with Bosch stainless steel appliances, granite countertops, larger center island and custom cabinetry—to the dining and living areas framed by expansive glass doors leading to a spacious deck overlooking the water. Rich hardwood flooring, recessed lighting, and a sleek built-in entertainment unit with beverage refrigerator create a polished yet inviting atmosphere perfect for entertaining. Upstairs, discover a large guest bedroom with vaulted ceilings and the primary suite that offers a private balcony with serene river views, dual closets, and a spa-inspired bath featuring a soaking tub, separate frameless shower with dual shower heads and bench seating, and dual vanities. The top-level private loft/ bonus room features an open skylight with great panoramic views of Annapolis and cedar closet that provides ample space for family or guests while the private lower-level bedroom with an en-suite bathroom and a walkout patio is perfect for visitors or a quiet home office. Additional features include an oversized 1-car garage with extended driveway and ample additional parking within the community, custom storage systems, integrated blinds, and meticulous craftsmanship throughout. Enjoy a lifestyle of sophistication and ease- walk to Eastports waterfront restaurants, local pubs, and marinas, or simply relax on your private balconies with front-row views of the Blue Angels flyovers, the Parade of Lights, Annapolis’ summer fireworks, and the city’s celebrated boat shows. Residents also enjoy optional membership access to the on-site marina and pool—available to join for an additional cost—offering resort-style amenities just steps from your door.

48 Chesapeake Lndg, Annapolis

Listing courtesy of Foraker Realty Co.. Contact:

Selling Office: TTR Sotheby's International Realty.

$872,500

Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Creek. An open floor plan, radiant floor heating, high ceilings in the great room create an ambience conducive to a luxury weekend retreat or full time residence. Water views are celebrated from nearly every inch of the home and the large windows allow for a deep connection with nature. Outdoor living is a highlight with a covered waterfront screened in porch for crab feasts, fire pit with seating providing sweeping views of Mill Creek, and expensive rear decks on each floor. Two bedrooms on the main level make one floor living a breeze including the primary with ensuite bathroom and walk in closet. Stainless steel appliances adorn the kitchen. The great room is impressive, creating a magnet effect for family and friends. Upstairs has an bonus room perfect for your home office. This is a boater's paradise with direct access to the bay within minutes but protected waters at your shoreline. The private dock includes an additional floating pier suitable for kayak excursions. The front yard has thoughtful planting, pea gravel driveway, and potting shed. Across the lane is an additional lot that comes with the property and is currently used for storage. Feel a connection with the Eastern Shore and its waterways with this high end waterfront sanctuary just 15 minutes from the shops, galleries, and restaurants of historic Chestertown.

3 Beds ⋅ 3 Baths

Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Creek. An open floor plan, radiant floor heating, high ceilings in the great room create an ambience conducive to a luxury weekend retreat or full time residence. Water views are celebrated from nearly every inch of the home and the large windows allow for a deep connection with nature. Outdoor living is a highlight with a covered waterfront screened in porch for crab feasts, fire pit with seating providing sweeping views of Mill Creek, and expensive rear decks on each floor. Two bedrooms on the main level make one floor living a breeze including the primary with ensuite bathroom and walk in closet. Stainless steel appliances adorn the kitchen. The great room is impressive, creating a magnet effect for family and friends. Upstairs has an bonus room perfect for your home office. This is a boater's paradise with direct access to the bay within minutes but protected waters at your shoreline. The private dock includes an additional floating pier suitable for kayak excursions. The front yard has thoughtful planting, pea gravel driveway, and potting shed. Across the lane is an additional lot that comes with the property and is currently used for storage. Feel a connection with the Eastern Shore and its waterways with this high end waterfront sanctuary just 15 minutes from the shops, galleries, and restaurants of historic Chestertown.

10761 Kasota Rd, Chestertown

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

Selling Office: Compass.

$384,000

Custom-Perfected Home with Luxury Finishes — Without the Luxury Price This beautifully reimagined 3-bedroom, 2-bath home (1,512 sq. ft.) sits on a generous .34-acre lot and offers high-end upgrades you’d expect to find in a designer showcase. The owners completely overhauled the home from top to bottom—correcting builder issues and enhancing every detail with thoughtful, custom touches. Step inside to discover modern farmhouse elegance, highlighted by a stunning chef’s kitchen where no detail was spared. From porcelain wood-look tile floors to solid wood KraftMaid soft-close cabinetry, quartz countertops, and a massive island, this kitchen is both functional and fabulous. You’ll love the hidden microwave, gold fixtures, pot filler, double Café dishwashers, Café refrigerator with Keurig dispenser, and brick tile backsplash—plus clever add-ons like concealed charging stations, pop-up countertop shelves, and pull-out drawers for effortless organization. The open living area features a custom shiplap accent wall, a cozy pellet stove, and custom steel handrails leading upstairs. There’s a bedroom and full bath on the first floor—perfect for guests or multigenerational living. Upstairs offers two additional bedrooms and a beautifully updated bath. Outside, your private paradise awaits. The backyard is partially enclosed with a 6-ft privacy fence, surrounded by raised garden beds (with tomatoes already growing!), a water-fed garden line, French drains for excellent drainage, and a concrete patio complete with hot tub, privacy pergola with curtains, outdoor TV, and lighting for evening entertaining. The impressive Amish-built 24x30 garage is more than just parking—it’s a dream workshop, featuring a 4-inch poured concrete pad with reinforced supports, mini-split HVAC, pellet stove, LED lighting, garage door opener, RV hook-up, and EV charging outlet. Additional upgrades include fresh interior paint, brick tile floors in the downstairs bath, custom window treatments on the back sliding door, and a recently completed septic and home inspection for peace of mind. Located in a community with optional HOA membership that grants access to water amenities. Enjoy easy proximity to Great Oak Marina—featuring a restaurant, beach bar, and live entertainment—plus charming Chestertown and Rock Hall, both just 12 minutes away. This is more than a home—it’s a showcase of craftsmanship, comfort, and creativity, all wrapped in affordability. You truly have to see it to believe it! Want to see these updated fun features in action, there is a video to show just that!

3 Beds ⋅ 2 Baths

Custom-Perfected Home with Luxury Finishes — Without the Luxury Price This beautifully reimagined 3-bedroom, 2-bath home (1,512 sq. ft.) sits on a generous .34-acre lot and offers high-end upgrades you’d expect to find in a designer showcase. The owners completely overhauled the home from top to bottom—correcting builder issues and enhancing every detail with thoughtful, custom touches. Step inside to discover modern farmhouse elegance, highlighted by a stunning chef’s kitchen where no detail was spared. From porcelain wood-look tile floors to solid wood KraftMaid soft-close cabinetry, quartz countertops, and a massive island, this kitchen is both functional and fabulous. You’ll love the hidden microwave, gold fixtures, pot filler, double Café dishwashers, Café refrigerator with Keurig dispenser, and brick tile backsplash—plus clever add-ons like concealed charging stations, pop-up countertop shelves, and pull-out drawers for effortless organization. The open living area features a custom shiplap accent wall, a cozy pellet stove, and custom steel handrails leading upstairs. There’s a bedroom and full bath on the first floor—perfect for guests or multigenerational living. Upstairs offers two additional bedrooms and a beautifully updated bath. Outside, your private paradise awaits. The backyard is partially enclosed with a 6-ft privacy fence, surrounded by raised garden beds (with tomatoes already growing!), a water-fed garden line, French drains for excellent drainage, and a concrete patio complete with hot tub, privacy pergola with curtains, outdoor TV, and lighting for evening entertaining. The impressive Amish-built 24x30 garage is more than just parking—it’s a dream workshop, featuring a 4-inch poured concrete pad with reinforced supports, mini-split HVAC, pellet stove, LED lighting, garage door opener, RV hook-up, and EV charging outlet. Additional upgrades include fresh interior paint, brick tile floors in the downstairs bath, custom window treatments on the back sliding door, and a recently completed septic and home inspection for peace of mind. Located in a community with optional HOA membership that grants access to water amenities. Enjoy easy proximity to Great Oak Marina—featuring a restaurant, beach bar, and live entertainment—plus charming Chestertown and Rock Hall, both just 12 minutes away. This is more than a home—it’s a showcase of craftsmanship, comfort, and creativity, all wrapped in affordability. You truly have to see it to believe it! Want to see these updated fun features in action, there is a video to show just that!

23416 Cloquet Rd, Chestertown

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

Selling Office: Compass.

$365,000

Tucked neatly on a corner in Chesapeake Landing, this three-quarter acre parcel is among one of the largest in the neighborhood. The 2020 custom built home exudes simple luxury. Offering three bedrooms and two full baths in a simple and efficient floorplan, is has flow and comfort in mind. It features a modern kitchen with tall quiet close cabinets, granite counter tops and a tile backsplash, stainless appliances, and an ample pantry for storage. Six-over-six oversized windows throughout the home, extra tall doors, a transom window over the front door, and a ten-foot door to the screen porch allows light to pour inside. A full and separate laundry room remove that chore from the living space and offer a dedicated work room with storage. The Primary Suite includes a generous walk-in closet and en suite bath. Since 2021, upgrades and improvements include: screened porch, Leafguard on all gutters, shed to coordinate with the home’s aesthetics, asphalt driveway, thoughtful landscaping, water treatment system, and is wired for IQ Fiber (formerly ThinkBig) for internet. This home is absolutely, without question, turnkey and ready for its new stewards!

3 Beds ⋅ 2 Baths

Tucked neatly on a corner in Chesapeake Landing, this three-quarter acre parcel is among one of the largest in the neighborhood. The 2020 custom built home exudes simple luxury. Offering three bedrooms and two full baths in a simple and efficient floorplan, is has flow and comfort in mind. It features a modern kitchen with tall quiet close cabinets, granite counter tops and a tile backsplash, stainless appliances, and an ample pantry for storage. Six-over-six oversized windows throughout the home, extra tall doors, a transom window over the front door, and a ten-foot door to the screen porch allows light to pour inside. A full and separate laundry room remove that chore from the living space and offer a dedicated work room with storage. The Primary Suite includes a generous walk-in closet and en suite bath. Since 2021, upgrades and improvements include: screened porch, Leafguard on all gutters, shed to coordinate with the home’s aesthetics, asphalt driveway, thoughtful landscaping, water treatment system, and is wired for IQ Fiber (formerly ThinkBig) for internet. This home is absolutely, without question, turnkey and ready for its new stewards!

23264 Clarissa Rd, Chestertown

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

Selling Office: Rosendale Realty.

$350,000

Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another great feature of this home. Call today for your showing appointment.

3 Beds ⋅ 2 Baths

Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another great feature of this home. Call today for your showing appointment.

10751 Millbrook Dr, Chestertown

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

Selling Office: Benson & Mangold, LLC.

$329,000

Offers due Wednesday 4/22 by 6PM! Welcome to this beautifully upgraded 3-bedroom, 2-bath Cape Cod, just six years young and perfectly situated in the sought-after Chesapeake Landing community! Ideally located directly across from the Turtle Trail and Millbrook Pond, you’ll love the peaceful, water-oriented setting with nearby access to a community boat ramp, fishing pier, Worton Creek marina, and new restaurant opening soon. This is far from your typical builder-grade home—the current owners have thoughtfully enhanced every inch. The kitchen truly shines with custom upgrades including a built-in pantry, stunning butcher block countertops, island addition, and bar-top seating—plus a full suite of high-end appliances (yes, even a refrigerator with a large touchscreen!). The flexible floor plan offers the best of both worlds with a dedicated dining room and a first-floor bedroom, ideal for guests or one-level living. Outside, enjoy an extended patio, freshly graded yard, and a new storage shed, creating the perfect outdoor space for relaxing or entertaining. With motivated sellers who have already found their next home, this is an incredible opportunity to move right in and start enjoying all that Chesapeake Landing has to offer. Don’t miss your chance to make it yours!

3 Beds ⋅ 2 Baths

Offers due Wednesday 4/22 by 6PM! Welcome to this beautifully upgraded 3-bedroom, 2-bath Cape Cod, just six years young and perfectly situated in the sought-after Chesapeake Landing community! Ideally located directly across from the Turtle Trail and Millbrook Pond, you’ll love the peaceful, water-oriented setting with nearby access to a community boat ramp, fishing pier, Worton Creek marina, and new restaurant opening soon. This is far from your typical builder-grade home—the current owners have thoughtfully enhanced every inch. The kitchen truly shines with custom upgrades including a built-in pantry, stunning butcher block countertops, island addition, and bar-top seating—plus a full suite of high-end appliances (yes, even a refrigerator with a large touchscreen!). The flexible floor plan offers the best of both worlds with a dedicated dining room and a first-floor bedroom, ideal for guests or one-level living. Outside, enjoy an extended patio, freshly graded yard, and a new storage shed, creating the perfect outdoor space for relaxing or entertaining. With motivated sellers who have already found their next home, this is an incredible opportunity to move right in and start enjoying all that Chesapeake Landing has to offer. Don’t miss your chance to make it yours!

10594 Millbrook Dr, Chestertown

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

Selling Office: Unrepresented.

$325,000

Welcome home to 10572 Watonga Road, a charming Cape Cod nestled on a beautifully wooded corner lot in the desirable Chesapeake Landing community. Built in 2007 and meticulously maintained, this 3-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and Eastern Shore charm. The spacious .35-acre property is surrounded by mature trees, creating peaceful wooded views from both the front and back of the home. Inside, you'll find luxury vinyl plank flooring throughout the main living areas in near-new condition, along with well-maintained carpeting in the bedrooms. Thoughtful updates include a water softener installed in 2024, a fenced yard added just two years ago, French drains, and two sump pumps designed to keep the property draining efficiently. An oversized shed provides excellent storage, while the deck offers the perfect place to enjoy your private outdoor setting. Life in Chesapeake Landing is all about enjoying nature and the water. Residents frequently spot deer, wild turkeys, turtles, and other local wildlife throughout this quiet, established neighborhood. There is no HOA, but the voluntary community association provides access to sought-after water amenities, including a community boat ramp, kayak launch, and fishing pier. The neighborhood also features Mill Brook Pond and the popular Turtle Walking Trail, giving residents even more opportunities to enjoy the outdoors. Located just minutes from historic Chestertown, you'll have easy access to everything that makes Kent County so special. Downtown Chestertown is only about seven minutes away and offers a vibrant year-round farmers market every Saturday from 9 a.m. to noon, locally owned shops, a beloved independent bookstore, and favorite dining destinations like Bad Alfred's Distilling. Also check out the sand bars at the marinas, perfect for waterfront happy hours. Whether you're drawn to the area's marinas, boating opportunities, charming small-town atmosphere, or the spacious homesites that provide room to breathe, this property delivers the true Eastern Shore lifestyle where water access is around every corner and community charm is abundant. If you've been searching for a home that combines modern convenience, natural beauty, and small-town waterfront living, 10572 Watonga Road is ready to welcome you home.

3 Beds ⋅ 2 Baths

Welcome home to 10572 Watonga Road, a charming Cape Cod nestled on a beautifully wooded corner lot in the desirable Chesapeake Landing community. Built in 2007 and meticulously maintained, this 3-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and Eastern Shore charm. The spacious .35-acre property is surrounded by mature trees, creating peaceful wooded views from both the front and back of the home. Inside, you'll find luxury vinyl plank flooring throughout the main living areas in near-new condition, along with well-maintained carpeting in the bedrooms. Thoughtful updates include a water softener installed in 2024, a fenced yard added just two years ago, French drains, and two sump pumps designed to keep the property draining efficiently. An oversized shed provides excellent storage, while the deck offers the perfect place to enjoy your private outdoor setting. Life in Chesapeake Landing is all about enjoying nature and the water. Residents frequently spot deer, wild turkeys, turtles, and other local wildlife throughout this quiet, established neighborhood. There is no HOA, but the voluntary community association provides access to sought-after water amenities, including a community boat ramp, kayak launch, and fishing pier. The neighborhood also features Mill Brook Pond and the popular Turtle Walking Trail, giving residents even more opportunities to enjoy the outdoors. Located just minutes from historic Chestertown, you'll have easy access to everything that makes Kent County so special. Downtown Chestertown is only about seven minutes away and offers a vibrant year-round farmers market every Saturday from 9 a.m. to noon, locally owned shops, a beloved independent bookstore, and favorite dining destinations like Bad Alfred's Distilling. Also check out the sand bars at the marinas, perfect for waterfront happy hours. Whether you're drawn to the area's marinas, boating opportunities, charming small-town atmosphere, or the spacious homesites that provide room to breathe, this property delivers the true Eastern Shore lifestyle where water access is around every corner and community charm is abundant. If you've been searching for a home that combines modern convenience, natural beauty, and small-town waterfront living, 10572 Watonga Road is ready to welcome you home.

10572 Watonga Rd, Chestertown

Listing courtesy of Serhant. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$320,000

Welcome to Chesapeake Landing — where new construction meets timeless Cape Cod charm in the heart of Chestertown, MD. This brand-new 3 BR / 2.5 BA home at 10584 Klamath Rd by Roger Reed Builders (MD Lic. #2464) is move-in ready with quality finishes throughout. The open main level features luxury vinyl plank flooring, white shaker cabinets, granite countertops, a full stainless steel appliance package (side-by-side refrigerator with ice maker, over-range microwave, built-in dishwasher, smooth-surface electric range), and a convenient half bath. The primary suite offers a walk-in closet, ceiling fan, and en suite bath with granite vanity. Two additional bedrooms and a full bath with granite counters round out the upper level. Enjoy the ease of a private well and septic, 2½-ton heat pump, and no HOA. Gravel driveway, vinyl siding, 25-year shingles, and three black exterior lights give great curb appeal. Don't miss your chance to own a brand-new home in one of Kent County's sought-after communities!

3 Beds ⋅ 2 Baths

Welcome to Chesapeake Landing — where new construction meets timeless Cape Cod charm in the heart of Chestertown, MD. This brand-new 3 BR / 2.5 BA home at 10584 Klamath Rd by Roger Reed Builders (MD Lic. #2464) is move-in ready with quality finishes throughout. The open main level features luxury vinyl plank flooring, white shaker cabinets, granite countertops, a full stainless steel appliance package (side-by-side refrigerator with ice maker, over-range microwave, built-in dishwasher, smooth-surface electric range), and a convenient half bath. The primary suite offers a walk-in closet, ceiling fan, and en suite bath with granite vanity. Two additional bedrooms and a full bath with granite counters round out the upper level. Enjoy the ease of a private well and septic, 2½-ton heat pump, and no HOA. Gravel driveway, vinyl siding, 25-year shingles, and three black exterior lights give great curb appeal. Don't miss your chance to own a brand-new home in one of Kent County's sought-after communities!

10584 Klamath Rd, Chestertown

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

Selling Office: Chesapeake Real Estate Associates, LLC.

$316,000

Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathrooms with a spacious eat-in kitchen and generous living room provides ample room for comfortable living. Move-in ready condition. Inside, you'll immediately notice the warmth and character of the stunning hardwood floors that flow throughout the home. The open and airy layout ensures a seamless flow between the living spaces, making it perfect for entertaining or just relaxing at home. The well-equipped laundry area comes complete with both a washer and dryer for added convenience. Take full advantage of the outdoor amenities this property has to offer. Start your mornings with coffee on the cozy screened porch or wind down your evenings on the expansive deck overlooking the fenced yard. There's plenty of space to garden, play, or simply enjoy the outdoors in privacy. The property also includes a garage, providing extra storage space and parking. This home is ideal for those seeking both charm and functionality in a serene setting. Don't miss the opportunity to call 10720 Foreston Rd your new home. Schedule your showing today to experience all that this property has to offer!

3 Beds ⋅ 2 Baths

Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathrooms with a spacious eat-in kitchen and generous living room provides ample room for comfortable living. Move-in ready condition. Inside, you'll immediately notice the warmth and character of the stunning hardwood floors that flow throughout the home. The open and airy layout ensures a seamless flow between the living spaces, making it perfect for entertaining or just relaxing at home. The well-equipped laundry area comes complete with both a washer and dryer for added convenience. Take full advantage of the outdoor amenities this property has to offer. Start your mornings with coffee on the cozy screened porch or wind down your evenings on the expansive deck overlooking the fenced yard. There's plenty of space to garden, play, or simply enjoy the outdoors in privacy. The property also includes a garage, providing extra storage space and parking. This home is ideal for those seeking both charm and functionality in a serene setting. Don't miss the opportunity to call 10720 Foreston Rd your new home. Schedule your showing today to experience all that this property has to offer!

10720 Foreston Rd, Chestertown

Listing courtesy of Compass. Contact:

Selling Office: Taylor Properties.

$262,000

Welcome to 83 Starboard Court. Easy to move in. Freshly painted throughout and brand new carpet. Updated windows 2024. Heat Pump 2018. Spacious kitchen and dining area with ceramic tile, appliances and large pantry, main level laundry, half bath and large family room on main level. Sliding door access to rear 12x 9 patio, attached storage shed and large flat fenced yard. Upstairs a large primary suite with walk in closet. Clean full bathroom and 2 additional bedrooms. Lots of extra storage area in the attic. Convenient location close to schools, shopping, I-95, APG, MARC and AMTRAK trains. Only 1 hour to Phila and BWI airports.

3 Beds ⋅ 2 Baths

Welcome to 83 Starboard Court. Easy to move in. Freshly painted throughout and brand new carpet. Updated windows 2024. Heat Pump 2018. Spacious kitchen and dining area with ceramic tile, appliances and large pantry, main level laundry, half bath and large family room on main level. Sliding door access to rear 12x 9 patio, attached storage shed and large flat fenced yard. Upstairs a large primary suite with walk in closet. Clean full bathroom and 2 additional bedrooms. Lots of extra storage area in the attic. Convenient location close to schools, shopping, I-95, APG, MARC and AMTRAK trains. Only 1 hour to Phila and BWI airports.

83 Starboard Ct, Perryville

Listing courtesy of Integrity Real Estate. Contact:

Selling Office: Cummings & Co Realtors.

$262,000

Welcome to this charming interior townhome in the Chesapeake Landing community of Perryville! This home features 3 bedrooms and 1.5 baths with a classic vinyl siding exterior, elegant trim above the windows and on porch pillars, and a covered front porch with a storm door. Inside, the home is appointed with neutral colors throughout. The living room is carpeted and highlighted by double windows for plenty of natural light. The kitchen features white cabinetry, stainless steel appliances, tile flooring, and a slider leading to a concrete patio with a retractable awning—perfect for outdoor entertaining. Upstairs, the primary bedroom welcomes you with double 6-panel entry doors and a large walk-in closet, while the hall full bath offers a tub/shower combo. Two additional bedrooms complete the upper level. The rear yard is fully fenced, and the home is conveniently located near schools, shopping, and major roadways, making it an ideal place to call home!

3 Beds ⋅ 2 Baths

Welcome to this charming interior townhome in the Chesapeake Landing community of Perryville! This home features 3 bedrooms and 1.5 baths with a classic vinyl siding exterior, elegant trim above the windows and on porch pillars, and a covered front porch with a storm door. Inside, the home is appointed with neutral colors throughout. The living room is carpeted and highlighted by double windows for plenty of natural light. The kitchen features white cabinetry, stainless steel appliances, tile flooring, and a slider leading to a concrete patio with a retractable awning—perfect for outdoor entertaining. Upstairs, the primary bedroom welcomes you with double 6-panel entry doors and a large walk-in closet, while the hall full bath offers a tub/shower combo. Two additional bedrooms complete the upper level. The rear yard is fully fenced, and the home is conveniently located near schools, shopping, and major roadways, making it an ideal place to call home!

29 Chartwell Ct, Perryville

Listing courtesy of Compass Home Group, LLC. Contact:

Selling Office: Samson Properties.

$261,000

Welcome to this completely renovated townhome in the Chesapeake Landing community of Perryville MD. This beautifully updated home is as close to new construction as you can get! The home features a new roof, new HVAC system, new water heater, new windows, and new doors. Inside you will find new luxury vinyl plank flooring and neutral paint. The living room offers plenty of space for gathering, relaxing, and entertaining. The gorgeous kitchen has brand new kitchen cabinets and all stainless appliances and granite counter tops. The new sliding glass door leads to a concrete patio that is perfect for outdoor entertaining. The upstairs features two large bedrooms with upgraded carpet. The full bathroom is updated and offers a double bowl vanity with granite tops. A large upstairs hall closet gives you plenty of storage area. Conveniently located with quick access to I95, APG, MARC Train station, and local stores and restaurants.

2 Beds ⋅ 2 Baths

Welcome to this completely renovated townhome in the Chesapeake Landing community of Perryville MD. This beautifully updated home is as close to new construction as you can get! The home features a new roof, new HVAC system, new water heater, new windows, and new doors. Inside you will find new luxury vinyl plank flooring and neutral paint. The living room offers plenty of space for gathering, relaxing, and entertaining. The gorgeous kitchen has brand new kitchen cabinets and all stainless appliances and granite counter tops. The new sliding glass door leads to a concrete patio that is perfect for outdoor entertaining. The upstairs features two large bedrooms with upgraded carpet. The full bathroom is updated and offers a double bowl vanity with granite tops. A large upstairs hall closet gives you plenty of storage area. Conveniently located with quick access to I95, APG, MARC Train station, and local stores and restaurants.

113 Starboard Ct, Perryville

Listing courtesy of Integrity Real Estate. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$259,900

Move-in ready 3 bedroom, 1.5 bath townhome located in the community of Chesapeake Landing. The main level has a freshly painted living room, updated kitchen with ample space for a dining room table, laundry closet, powder room, and utility closet. Upstairs offers a spacious primary bedroom with walk-in closet, full bath with dual sink vanity, and two additional bedrooms. Exterior features include a concrete patio, storage room, and a fenced yard. Upgrades include a newer roof (2018), HVAC system (2019), and water heater (2019). HOA dues include trash, snow removal, and common area maintenance. Two assigned parking spots, plus plenty of overflow parking in the cul-de-sac. Conveniently located near I-95, Aberdeen Proving Ground, MARC train station, marinas, and restaurants. Schedule your private tour today!

3 Beds ⋅ 2 Baths

Move-in ready 3 bedroom, 1.5 bath townhome located in the community of Chesapeake Landing. The main level has a freshly painted living room, updated kitchen with ample space for a dining room table, laundry closet, powder room, and utility closet. Upstairs offers a spacious primary bedroom with walk-in closet, full bath with dual sink vanity, and two additional bedrooms. Exterior features include a concrete patio, storage room, and a fenced yard. Upgrades include a newer roof (2018), HVAC system (2019), and water heater (2019). HOA dues include trash, snow removal, and common area maintenance. Two assigned parking spots, plus plenty of overflow parking in the cul-de-sac. Conveniently located near I-95, Aberdeen Proving Ground, MARC train station, marinas, and restaurants. Schedule your private tour today!

81 Starboard Ct, Perryville

Listing courtesy of Integrity Real Estate. Contact:

Selling Office: Compass.

$258,500

Move-In Ready Townhome in Historic Perryville – This charming townhome blends fresh updates with everyday comfort. A welcoming portico entrance with a storm door greets you as you arrive, while the foyer offers a convenient guest closet. The bright living room features large windows that fill the space with natural light, along with a ceiling fan and cozy carpeting. The updated main-level powder room showcases stylish wainscoting, attractive wallpaper, and a new mirror. The heart of the home is the spacious eat-in kitchen, refreshed with painted cabinetry, updated countertops and sink, and a stainless steel built-in microwave and oven installed in 2023. A walk-in pantry provides excellent storage, while the laundry closet includes a full-size front-load washer and dryer (2023). Sliding glass doors lead to a private patio and open, level yard—perfect for cookouts, playtime, or relaxing outdoors. An attached storage area keeps sports equipment, tools, and seasonal décor neatly tucked away. Upstairs, a convenient landing and linen closet add functionality. Three bedrooms feature ceiling fans, neutral décor, and carpeting throughout. The primary bedroom includes a walk-in closet featuring a custom organization system. The additional bedrooms offer versatility to meet your needs—use them as bedrooms, guest rooms, a home office, hobby room, or exercise space, with one featuring a walk-in closet. A full hall bath offers dual sinks and an easy-to-maintain one-piece tub/shower. Major updates include a roof replaced in 2022, water heater replaced in 2024, and heat pump/HVAC replaced in 2018. Located in the charming historic town of Perryville, where the Susquehanna River meets the Chesapeake Bay, this home offers convenient access to the MARC Penn Line for commuting to Baltimore and Washington, D.C., as well as easy access to I-95 and Route 40. This one truly has it all—just move in and start enjoying!

3 Beds ⋅ 2 Baths

Move-In Ready Townhome in Historic Perryville – This charming townhome blends fresh updates with everyday comfort. A welcoming portico entrance with a storm door greets you as you arrive, while the foyer offers a convenient guest closet. The bright living room features large windows that fill the space with natural light, along with a ceiling fan and cozy carpeting. The updated main-level powder room showcases stylish wainscoting, attractive wallpaper, and a new mirror. The heart of the home is the spacious eat-in kitchen, refreshed with painted cabinetry, updated countertops and sink, and a stainless steel built-in microwave and oven installed in 2023. A walk-in pantry provides excellent storage, while the laundry closet includes a full-size front-load washer and dryer (2023). Sliding glass doors lead to a private patio and open, level yard—perfect for cookouts, playtime, or relaxing outdoors. An attached storage area keeps sports equipment, tools, and seasonal décor neatly tucked away. Upstairs, a convenient landing and linen closet add functionality. Three bedrooms feature ceiling fans, neutral décor, and carpeting throughout. The primary bedroom includes a walk-in closet featuring a custom organization system. The additional bedrooms offer versatility to meet your needs—use them as bedrooms, guest rooms, a home office, hobby room, or exercise space, with one featuring a walk-in closet. A full hall bath offers dual sinks and an easy-to-maintain one-piece tub/shower. Major updates include a roof replaced in 2022, water heater replaced in 2024, and heat pump/HVAC replaced in 2018. Located in the charming historic town of Perryville, where the Susquehanna River meets the Chesapeake Bay, this home offers convenient access to the MARC Penn Line for commuting to Baltimore and Washington, D.C., as well as easy access to I-95 and Route 40. This one truly has it all—just move in and start enjoying!

47 Oxford Ct, Perryville

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: EXIT Preferred Realty.

$257,000

Offer deadline of 7pm on Thursday 6/11, seller reserves the right to accept an offer before that time and date if they choose... Welcome to this brick front townhouse with tons of charm!! Large living room leads to an eat in kitchen with Stainless steel appliances (2023) and a walk in Pantry, brand new garbage disposal (2026).. LVP throughout the first level (2025) Updated half bath that is a designers dream! First floor laundry ( Washer and dryer not included), Sliders lead to concrete pad and fully fenced yard (2023) as well as an attached storage shed and a detached shed (2024).. Upstairs offers 3 bedrooms, Owners Bedroom offers a walk in closet!! Updated Full Bath with dual sinks! HVAC 2020 water heater 2007

3 Beds ⋅ 2 Baths

Offer deadline of 7pm on Thursday 6/11, seller reserves the right to accept an offer before that time and date if they choose... Welcome to this brick front townhouse with tons of charm!! Large living room leads to an eat in kitchen with Stainless steel appliances (2023) and a walk in Pantry, brand new garbage disposal (2026).. LVP throughout the first level (2025) Updated half bath that is a designers dream! First floor laundry ( Washer and dryer not included), Sliders lead to concrete pad and fully fenced yard (2023) as well as an attached storage shed and a detached shed (2024).. Upstairs offers 3 bedrooms, Owners Bedroom offers a walk in closet!! Updated Full Bath with dual sinks! HVAC 2020 water heater 2007

35 Chartwell Ct, Perryville

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Coldwell Banker Realty.

$254,000

NEW CARPET throughout! NEW DISHWASHER! NEW ROOF! Welcome to Chesapeake Landing in Perryville, where comfort, style, and convenience come together in this charming 3-bedroom, 1.5-bath interior townhome. Featuring an attractive brick-front exterior with elegant trim details and classic green shutters, this move-in-ready home offers wonderful curb appeal and thoughtful updates throughout. Step inside to find a bright and inviting living room filled with natural light from oversized double windows and complemented by neutral décor that creates a warm, welcoming atmosphere. The spacious eat-in kitchen is sure to impress with upgraded granite countertops, updated flooring, a pantry, newer appliances, and a sliding glass door that opens to the concrete patio and backyard. This outdoor space is perfect for relaxing, entertaining, or enjoying your morning coffee, while the attached shed provides valuable secure storage. Enjoy added peace of mind with a new roof and newer water heater. Upstairs, the spacious primary bedroom features elegant double 6-panel entry doors and a large walk-in closet. Two additional bedrooms and a full hall bath with a tub/shower combination complete the upper level. Ideally located near schools, shopping, dining, and major commuter routes, this home offers the perfect blend of value, functionality, and location. Whether you're a first-time homebuyer, looking to downsize, or seeking an investment opportunity, this Chesapeake Landing gem is ready to welcome you home!

3 Beds ⋅ 2 Baths

NEW CARPET throughout! NEW DISHWASHER! NEW ROOF! Welcome to Chesapeake Landing in Perryville, where comfort, style, and convenience come together in this charming 3-bedroom, 1.5-bath interior townhome. Featuring an attractive brick-front exterior with elegant trim details and classic green shutters, this move-in-ready home offers wonderful curb appeal and thoughtful updates throughout. Step inside to find a bright and inviting living room filled with natural light from oversized double windows and complemented by neutral décor that creates a warm, welcoming atmosphere. The spacious eat-in kitchen is sure to impress with upgraded granite countertops, updated flooring, a pantry, newer appliances, and a sliding glass door that opens to the concrete patio and backyard. This outdoor space is perfect for relaxing, entertaining, or enjoying your morning coffee, while the attached shed provides valuable secure storage. Enjoy added peace of mind with a new roof and newer water heater. Upstairs, the spacious primary bedroom features elegant double 6-panel entry doors and a large walk-in closet. Two additional bedrooms and a full hall bath with a tub/shower combination complete the upper level. Ideally located near schools, shopping, dining, and major commuter routes, this home offers the perfect blend of value, functionality, and location. Whether you're a first-time homebuyer, looking to downsize, or seeking an investment opportunity, this Chesapeake Landing gem is ready to welcome you home!

39 Chartwell Ct, Perryville

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

Selling Office: Integrity Real Estate.

$251,000

Coming Soon! Townhouse in Chesapeake Landing! Features: 2 spacious bedrooms, 2.5 baths, large kitchen/dining combo, bonus room in the basement, updated flooring throughout most of the main level, a new front door, and a nice backyard with patio. Located conveniently to Rt. 40 & I95 for easy commuting. Close to The Town of Perryville for parks, boat launch, and dining.

2 Beds ⋅ 3 Baths

Coming Soon! Townhouse in Chesapeake Landing! Features: 2 spacious bedrooms, 2.5 baths, large kitchen/dining combo, bonus room in the basement, updated flooring throughout most of the main level, a new front door, and a nice backyard with patio. Located conveniently to Rt. 40 & I95 for easy commuting. Close to The Town of Perryville for parks, boat launch, and dining.

8 Anchor Ct, Perryville

Listing courtesy of Remax Vision. Contact:

Selling Office: Realty Plus Associates.

$247,500

Welcome to 11 Anchor Court — a beautiful home tucked away in a quiet cul-de-sac, where comfort meets Chesapeake charm. This beautifully maintained home offers the perfect blend of style, space, and convenience, just minutes from almost everything and commuter routes. Step inside to find a bright, open layout that flows effortlessly from the living room into the dining area and kitchen — ideal for both entertaining and everyday living. The kitchen features modern updates, ample cabinetry, and backyard views that bring in plenty of natural light. Upstairs, you’ll find three generously sized bedrooms. The finished lower level expands your living space — perfect for a media room, home gym, or guest retreat. Outside, enjoy your morning coffee or evening gatherings on the patio overlooking the fenced yard — a private oasis ready for summer barbecues or quiet sunsets. Located close to local shops, and the historic charm of downtown Perryville, this home captures the best of small-town life with easy access to I-95, Aberdeen Proving Ground, and the Delaware line. Come drop your anchor — 11 Anchor Ct is ready to welcome you home.

3 Beds ⋅ 2 Baths

Welcome to 11 Anchor Court — a beautiful home tucked away in a quiet cul-de-sac, where comfort meets Chesapeake charm. This beautifully maintained home offers the perfect blend of style, space, and convenience, just minutes from almost everything and commuter routes. Step inside to find a bright, open layout that flows effortlessly from the living room into the dining area and kitchen — ideal for both entertaining and everyday living. The kitchen features modern updates, ample cabinetry, and backyard views that bring in plenty of natural light. Upstairs, you’ll find three generously sized bedrooms. The finished lower level expands your living space — perfect for a media room, home gym, or guest retreat. Outside, enjoy your morning coffee or evening gatherings on the patio overlooking the fenced yard — a private oasis ready for summer barbecues or quiet sunsets. Located close to local shops, and the historic charm of downtown Perryville, this home captures the best of small-town life with easy access to I-95, Aberdeen Proving Ground, and the Delaware line. Come drop your anchor — 11 Anchor Ct is ready to welcome you home.

11 Anchor Ct, Perryville

Listing courtesy of BHHS Fox & Roach - Hockessin. Contact:

Selling Office: Coldwell Banker Realty.

$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:

Selling Office: Chesapeake Real Estate Associates, LLC.

$231,000

**OFFER RECEIVED…HIGHEST AND BEST BY MONDAY 2/16 BY 7 PM** Pride of ownership shows throughout in this great starter home in sought after Chesapeake landing! Featuring 3 bedrooms and 1 full bath, this end unit townhome has been well kept and is freshly painted throughout. It has a family room leading into a large eat-in kitchen. Sliders off the kitchen to fenced back yard with storage shed included. Main level pantry and laundry, Upstairs is the primary bedroom and two additional bedrooms and a full bath. Move right in...this home shows very well and is neat as a pin!

3 Beds ⋅ 1 Baths

**OFFER RECEIVED…HIGHEST AND BEST BY MONDAY 2/16 BY 7 PM** Pride of ownership shows throughout in this great starter home in sought after Chesapeake landing! Featuring 3 bedrooms and 1 full bath, this end unit townhome has been well kept and is freshly painted throughout. It has a family room leading into a large eat-in kitchen. Sliders off the kitchen to fenced back yard with storage shed included. Main level pantry and laundry, Upstairs is the primary bedroom and two additional bedrooms and a full bath. Move right in...this home shows very well and is neat as a pin!

15 Anchor Ct, Perryville

Listing courtesy of Remax Vision. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$175,000

Calling all Investors or handman looking for a project! This 2 bedroom 1.5 bath townhome in the community of Chesapeake Landing needs extensive repairs but has the potential to be a great first home or investment property. Home is being sold as is and has been priced based off of condition! Make your offer today to bring this home back to its original beauty!

2 Beds ⋅ 2 Baths

Calling all Investors or handman looking for a project! This 2 bedroom 1.5 bath townhome in the community of Chesapeake Landing needs extensive repairs but has the potential to be a great first home or investment property. Home is being sold as is and has been priced based off of condition! Make your offer today to bring this home back to its original beauty!

113 Starboard Ct, Perryville

Listing courtesy of RE/MAX Point Realty. Contact:

Selling Office: Integrity Real Estate.

$7,200

Kent County Health Dept has no record of perc

Lots 253-254 Carimon Road, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$5,000

Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek. Lot failed percolation Test in March of 1989.

Lot 24 & 25 Buck Neck, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

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