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$1,199,900

COMING SOON. It's rare to find a designer home on a 1.4 acre lot with an in-ground saltwater pool and direct waterfront access on Kent Island at this price tag. From the moment you arrive, the outdoor setting feels like a private resort. A sparkling saltwater pool is surrounded by a newly hardscaped stone terrace, mature lawn & landscaping, apple tree, fig tree, cypress tree, and even strawberries! The rear backs up to farmland creating a secluded, private feel. Walk out your front door, directly to the left of the house to access your own 90 foot pier extends out offering direct access to Kirwan Creek for small boats, kayaking, paddle boarding, fishing, crabbing, wildlife and sunset watching. Imagine walking outside, breathe in the fresh air with morning coffee in hand, walk across your beautiful flat yard, pick a fresh apple along the way, and step onto your own dock to enjoy the classic Chesapeake Bay lifestyle you've been craving. Moving inside the 3,000 square foot home, the original intent of the owner was to create coastal inspired retreat for anyone who walked through the front doors. Each space has been re-imagined with professional interior designer style throughout with coastal wallpaper, nautical colors, custom curtains, trim work, updated light fixtures and more. The main level heart of the home you'll find an updated kitchen (currently under construction for new light countertops, ceramic tile backsplash, and fresh hardware) with a sweet breakfast table nook. Off the kitchen is a dedicated dining room space with gorgeous wallpaper and updated lighting overlooking the backyard. Step down to the airy main living room centered by electric fireplace and opening to a stunning all window sunroom overlooking your backyard paradise. The main level front room has been converted to functional main level bedroom and the bathroom was updated to a full main level bathroom. Upstairs, the oversized primary suite is designed as a true private retreat, complete with a dedicated lounge area and dreamy spa inspired bathroom. The stunning bath features a freestanding soaking tub, double vanity, large-format tile, and a beautiful tiled shower with dual shower heads. Three additional bedrooms including a custom-designed bunk room with a beautifully renovated hall full bathroom, while a dedicated laundry space off the upstairs hallway adds everyday convenience. The garage was converted into a recreational space (2026) similar to what could be offered by a "finished basement" with versatility to be additional living room, game room, playroom, gym, or easily converted back to the 2 car garage for covered parking. Notable system updates: insulated and added vapor barrier to crawlspace (2026), installed HVAC in garage (2026), main house HVAC (2020), added mini split in sunroom (2022), hot water heater (2022), full primary bathroom renovation (2026), kitchen updated (2026), main level bathroom (2026), hallway renovation bathroom (2026), refinished/stained hardwood floors (2026), newer pool equipment, painted brick on exterior with special masonry paint (2026), and much more (see full list). Nestled within in close-knit community of Kirwans Landing on Kent Island, you are surrounded by homes on large, manicured lots with a strong sense of pride to the overall appearance of the neighborhood. You are walking distance to the community marina with access to private boat slip in deep water. The neighborhood is an easy 5 min drive to Bay Bridge. This is a WOW property that you must see in person to appreciate how special it would be to call this your home. Living on Kent Island offers a waterfront, relaxed lifestyle with a little more space than other waterfront areas in Maryland.

5 Beds ⋅ 3 Baths

COMING SOON. It's rare to find a designer home on a 1.4 acre lot with an in-ground saltwater pool and direct waterfront access on Kent Island at this price tag. From the moment you arrive, the outdoor setting feels like a private resort. A sparkling saltwater pool is surrounded by a newly hardscaped stone terrace, mature lawn & landscaping, apple tree, fig tree, cypress tree, and even strawberries! The rear backs up to farmland creating a secluded, private feel. Walk out your front door, directly to the left of the house to access your own 90 foot pier extends out offering direct access to Kirwan Creek for small boats, kayaking, paddle boarding, fishing, crabbing, wildlife and sunset watching. Imagine walking outside, breathe in the fresh air with morning coffee in hand, walk across your beautiful flat yard, pick a fresh apple along the way, and step onto your own dock to enjoy the classic Chesapeake Bay lifestyle you've been craving. Moving inside the 3,000 square foot home, the original intent of the owner was to create coastal inspired retreat for anyone who walked through the front doors. Each space has been re-imagined with professional interior designer style throughout with coastal wallpaper, nautical colors, custom curtains, trim work, updated light fixtures and more. The main level heart of the home you'll find an updated kitchen (currently under construction for new light countertops, ceramic tile backsplash, and fresh hardware) with a sweet breakfast table nook. Off the kitchen is a dedicated dining room space with gorgeous wallpaper and updated lighting overlooking the backyard. Step down to the airy main living room centered by electric fireplace and opening to a stunning all window sunroom overlooking your backyard paradise. The main level front room has been converted to functional main level bedroom and the bathroom was updated to a full main level bathroom. Upstairs, the oversized primary suite is designed as a true private retreat, complete with a dedicated lounge area and dreamy spa inspired bathroom. The stunning bath features a freestanding soaking tub, double vanity, large-format tile, and a beautiful tiled shower with dual shower heads. Three additional bedrooms including a custom-designed bunk room with a beautifully renovated hall full bathroom, while a dedicated laundry space off the upstairs hallway adds everyday convenience. The garage was converted into a recreational space (2026) similar to what could be offered by a "finished basement" with versatility to be additional living room, game room, playroom, gym, or easily converted back to the 2 car garage for covered parking. Notable system updates: insulated and added vapor barrier to crawlspace (2026), installed HVAC in garage (2026), main house HVAC (2020), added mini split in sunroom (2022), hot water heater (2022), full primary bathroom renovation (2026), kitchen updated (2026), main level bathroom (2026), hallway renovation bathroom (2026), refinished/stained hardwood floors (2026), newer pool equipment, painted brick on exterior with special masonry paint (2026), and much more (see full list). Nestled within in close-knit community of Kirwans Landing on Kent Island, you are surrounded by homes on large, manicured lots with a strong sense of pride to the overall appearance of the neighborhood. You are walking distance to the community marina with access to private boat slip in deep water. The neighborhood is an easy 5 min drive to Bay Bridge. This is a WOW property that you must see in person to appreciate how special it would be to call this your home. Living on Kent Island offers a waterfront, relaxed lifestyle with a little more space than other waterfront areas in Maryland.

162 Kirwans Landing Ln, Chester

Listing courtesy of Next Step Realty. Contact:

$549,950

Experience everything Four Seasons at Kent Island has to offer without the wait! Less than one year old, this beautifully maintained home shows like new and offers one of the most desirable locations in the community, with exceptional water views, ground-level living, and an easy walk to the clubhouse and resort-style amenities. Plus, the home is still under warranty with the builder. Inside, you'll find an open-concept floor plan filled with natural light and beautiful water views. The gourmet kitchen features quartz countertops, upgraded cabinetry, GE Café appliances including double wall ovens, stainless steel appliances, tile backsplash, and plenty of space for entertaining. Luxury vinyl plank flooring flows through the main living areas, and an electric fireplace adds a cozy touch to the living room. The primary suite offers water views, private patio access, a large walk-in closet, and a spacious ensuite bath. A second bedroom suite provides a comfortable space for guests, while the private office offers flexibility for working from home or additional living space. Other upgrades include approximately $8,000 in remote-controlled window treatments, a private walk-out patio, climate-controlled storage, and an attached one-car garage. Step outside and enjoy the convenience of ground-level access and the waterfront lifestyle that makes Four Seasons so special. The 24,000-square-foot Chester House clubhouse is just a short walk away and features indoor and outdoor pools, a fitness center, yoga studio, game rooms, library, gathering spaces, and more. Residents also enjoy pickleball, tennis, bocce, walking and biking trails, a kayak and paddleboard launch, fishing and boat pier, dog park, waterfront beach area, fire pits, tiki bar, and a full calendar of clubs, fitness classes, and social events. Located on Kent Island just minutes from the Bay Bridge, Four Seasons offers easy access to Annapolis, Baltimore, DC, and Maryland's Eastern Shore. Waterfront dining, boating, golf, shopping, and the Chesapeake Bay lifestyle are all close by. Why wait for new construction when you can move right into a nearly new home with upgrades already completed?

2 Beds ⋅ 3 Baths

Experience everything Four Seasons at Kent Island has to offer without the wait! Less than one year old, this beautifully maintained home shows like new and offers one of the most desirable locations in the community, with exceptional water views, ground-level living, and an easy walk to the clubhouse and resort-style amenities. Plus, the home is still under warranty with the builder. Inside, you'll find an open-concept floor plan filled with natural light and beautiful water views. The gourmet kitchen features quartz countertops, upgraded cabinetry, GE Café appliances including double wall ovens, stainless steel appliances, tile backsplash, and plenty of space for entertaining. Luxury vinyl plank flooring flows through the main living areas, and an electric fireplace adds a cozy touch to the living room. The primary suite offers water views, private patio access, a large walk-in closet, and a spacious ensuite bath. A second bedroom suite provides a comfortable space for guests, while the private office offers flexibility for working from home or additional living space. Other upgrades include approximately $8,000 in remote-controlled window treatments, a private walk-out patio, climate-controlled storage, and an attached one-car garage. Step outside and enjoy the convenience of ground-level access and the waterfront lifestyle that makes Four Seasons so special. The 24,000-square-foot Chester House clubhouse is just a short walk away and features indoor and outdoor pools, a fitness center, yoga studio, game rooms, library, gathering spaces, and more. Residents also enjoy pickleball, tennis, bocce, walking and biking trails, a kayak and paddleboard launch, fishing and boat pier, dog park, waterfront beach area, fire pits, tiki bar, and a full calendar of clubs, fitness classes, and social events. Located on Kent Island just minutes from the Bay Bridge, Four Seasons offers easy access to Annapolis, Baltimore, DC, and Maryland's Eastern Shore. Waterfront dining, boating, golf, shopping, and the Chesapeake Bay lifestyle are all close by. Why wait for new construction when you can move right into a nearly new home with upgrades already completed?

630 Warbler Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

$1,250,000

Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with the timeless appeal of Maryland's Eastern Shore. Offering 3 bedrooms, 2.5 baths, and a highly desirable main-level primary suite, the thoughtfully designed layout provides both comfort and functionality. Inside, you'll find a dedicated home office and stylish engineered hardwood and tile flooring throughout, creating a seamless and low-maintenance living space. Large windows invite natural light and showcase the home's tranquil waterfront setting. Outdoor living is just as impressive, featuring two maintenance-free decks, a patio ideal for grilling and entertaining, and a fenced backyard perfect for pets, play, or simply enjoying the beautiful surroundings. Whether hosting friends or relaxing with a morning coffee, this home offers multiple spaces to take in the peaceful water views. Boating enthusiasts will appreciate the private pier equipped with both water and electric service, while the pier decking was replaced last year, providing added value and peace of mind. Enjoy easy access to boating, fishing, crabbing, kayaking, and all the activities that make waterfront living so special. Conveniently located on Kent Island near shopping, dining, marinas, and commuter routes, this exceptional waterfront property offers the perfect blend of luxury, comfort, and Chesapeake Bay lifestyle. 3 Bedrooms | 2.5 Baths | Main-Level Primary Suite | Separate Office | Waterfront on Cox Creek | Private Pier with Water & Electric | New Pier Decking (2025) | Two Maintenance-Free Decks | Grilling Patio | Fenced Backyard | Renovated Approximately 4 Years Ago

3 Beds ⋅ 3 Baths

Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with the timeless appeal of Maryland's Eastern Shore. Offering 3 bedrooms, 2.5 baths, and a highly desirable main-level primary suite, the thoughtfully designed layout provides both comfort and functionality. Inside, you'll find a dedicated home office and stylish engineered hardwood and tile flooring throughout, creating a seamless and low-maintenance living space. Large windows invite natural light and showcase the home's tranquil waterfront setting. Outdoor living is just as impressive, featuring two maintenance-free decks, a patio ideal for grilling and entertaining, and a fenced backyard perfect for pets, play, or simply enjoying the beautiful surroundings. Whether hosting friends or relaxing with a morning coffee, this home offers multiple spaces to take in the peaceful water views. Boating enthusiasts will appreciate the private pier equipped with both water and electric service, while the pier decking was replaced last year, providing added value and peace of mind. Enjoy easy access to boating, fishing, crabbing, kayaking, and all the activities that make waterfront living so special. Conveniently located on Kent Island near shopping, dining, marinas, and commuter routes, this exceptional waterfront property offers the perfect blend of luxury, comfort, and Chesapeake Bay lifestyle. 3 Bedrooms | 2.5 Baths | Main-Level Primary Suite | Separate Office | Waterfront on Cox Creek | Private Pier with Water & Electric | New Pier Decking (2025) | Two Maintenance-Free Decks | Grilling Patio | Fenced Backyard | Renovated Approximately 4 Years Ago

1717 Harbor Dr, Chester

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

$585,000

Welcome to this stunning home in the picturesque 55+ Community of Bay Bridge Cove - the place for Kent Island living at its best, so close to the waters of the Chesapeake Bay. This 3-bedroom, 3-bath home offers so many upgraded features. Conveniently located across from the community center and backing up to quiet, tree-lined space, you are steps away from enjoying all the amenities the neighborhood has to offer. Welcoming you at the front of the home is your own private courtyard, with space to sit and relax or socialize with friends under the strings of cafe lights. Walk inside to the warm-toned luxury wood plank vinyl floors throughout the entire first floor; abundant light spills in to accent the paneled foyer with upper crown molding. The roomy kitchen features soft-close cabinets/drawers with lots of storage, pull-out trash and recycle bins, a corner cabinet with lazy-susan shelving, stainless steel appliances, premium countertops and backsplash, under-the-counter lighting, and updated cabinet knobs and pendant lights. The main level great room has plenty of space for a large dining table and your comfortable living room furniture, and features a cozy gas fireplace (and includes a convenient wall mount for your TV). Step into the bright and airy sunroom at the back of the home - make it your book nook, office, or a spot to enjoy your guests. The primary bedroom features a tray ceiling, 2 walk-in closets (one is huge!), and a private bath with tiled shower and ceramic tiled flooring. The 2nd bedroom on the first floor connects to the hall bath. A sizable laundry room includes upgraded Samsung appliances, shelving, and a storage closet. Upstairs you'll find a relaxing retreat with a large loft area, a bedroom with walk-in closet, and a full bath. A bonus feature of this home is the beautifully enhanced loft wall on each side with added railing, making this space safe for the little ones while maintaining the line of sight to the first floor. With ceiling fans throughout, added storm doors on the front and back with pull-down screens, unique custom blinds on all windows matched perfectly to the function of each room, and an irrigation system for low-maintenance gardening, this home may be the perfect one you've been looking for! This thriving community has it all - a calendar of activities and outings, bocce and pickleball, picnics at the crab shack, a pool, indoor gym, library, game rooms, community garden and fresh herb garden, walking paths around the beautifully landscaped ponds, and quick access to the Cross Island Trail right next to the neighborhood. There's so much to do here!

3 Beds ⋅ 3 Baths

Welcome to this stunning home in the picturesque 55+ Community of Bay Bridge Cove - the place for Kent Island living at its best, so close to the waters of the Chesapeake Bay. This 3-bedroom, 3-bath home offers so many upgraded features. Conveniently located across from the community center and backing up to quiet, tree-lined space, you are steps away from enjoying all the amenities the neighborhood has to offer. Welcoming you at the front of the home is your own private courtyard, with space to sit and relax or socialize with friends under the strings of cafe lights. Walk inside to the warm-toned luxury wood plank vinyl floors throughout the entire first floor; abundant light spills in to accent the paneled foyer with upper crown molding. The roomy kitchen features soft-close cabinets/drawers with lots of storage, pull-out trash and recycle bins, a corner cabinet with lazy-susan shelving, stainless steel appliances, premium countertops and backsplash, under-the-counter lighting, and updated cabinet knobs and pendant lights. The main level great room has plenty of space for a large dining table and your comfortable living room furniture, and features a cozy gas fireplace (and includes a convenient wall mount for your TV). Step into the bright and airy sunroom at the back of the home - make it your book nook, office, or a spot to enjoy your guests. The primary bedroom features a tray ceiling, 2 walk-in closets (one is huge!), and a private bath with tiled shower and ceramic tiled flooring. The 2nd bedroom on the first floor connects to the hall bath. A sizable laundry room includes upgraded Samsung appliances, shelving, and a storage closet. Upstairs you'll find a relaxing retreat with a large loft area, a bedroom with walk-in closet, and a full bath. A bonus feature of this home is the beautifully enhanced loft wall on each side with added railing, making this space safe for the little ones while maintaining the line of sight to the first floor. With ceiling fans throughout, added storm doors on the front and back with pull-down screens, unique custom blinds on all windows matched perfectly to the function of each room, and an irrigation system for low-maintenance gardening, this home may be the perfect one you've been looking for! This thriving community has it all - a calendar of activities and outings, bocce and pickleball, picnics at the crab shack, a pool, indoor gym, library, game rooms, community garden and fresh herb garden, walking paths around the beautifully landscaped ponds, and quick access to the Cross Island Trail right next to the neighborhood. There's so much to do here!

222 Moorings Cir Unit 126, Stevensville

Listing courtesy of The KW Collective. Contact:

$249,000

Rare offering of a surveyed, perced, and cleared commercial lot with high exposure in Queen Anne County! 1.49 acres. See attached documents for survey, perc, and allowable uses. This is an exceptional location to move your existing small business to or to start your new business.

Chester River Heights Road, Millington

Listing courtesy of Select Land & Homes, LLC. Contact:

$429,900

*MAJOR PRICE IMPROVEMENT! Welcome to this beautifully renovated and remodeled 3-bedroom, 2-bath home offering the perfect blend of modern style, comfort, and location. Designed with today’s lifestyle in mind, this home features a bright open floor plan with spacious living and dining areas that flow seamlessly into the stunning gourmet kitchen. The kitchen is a true showstopper with elegant quartz countertops, a large center island, and ample space for cooking, gathering, and entertaining. Both full bathrooms have been tastefully updated with ceramic tile finishes and brand-new high-end vanities. The spacious primary suite offers a private retreat with its own en-suite bathroom for added comfort and convenience. Step outside to enjoy the level front and backyard spaces, ideal for outdoor entertaining, gardening, play, or simply relaxing. Located just one block from the Chesapeake Bay, you’ll love the nearby neighborhood waterfront park featuring picnic areas and fishing access. Conveniently situated for commuters, this home offers easy access to the Eastern Shore beaches, Washington, DC, and Baltimore—making it the perfect place to enjoy coastal living with city convenience. Don’t miss this exceptional opportunity! Seller will consider leasing the property to qualified tenants for $3000 per month plus $3000 security deposit.

3 Beds ⋅ 2 Baths

*MAJOR PRICE IMPROVEMENT! Welcome to this beautifully renovated and remodeled 3-bedroom, 2-bath home offering the perfect blend of modern style, comfort, and location. Designed with today’s lifestyle in mind, this home features a bright open floor plan with spacious living and dining areas that flow seamlessly into the stunning gourmet kitchen. The kitchen is a true showstopper with elegant quartz countertops, a large center island, and ample space for cooking, gathering, and entertaining. Both full bathrooms have been tastefully updated with ceramic tile finishes and brand-new high-end vanities. The spacious primary suite offers a private retreat with its own en-suite bathroom for added comfort and convenience. Step outside to enjoy the level front and backyard spaces, ideal for outdoor entertaining, gardening, play, or simply relaxing. Located just one block from the Chesapeake Bay, you’ll love the nearby neighborhood waterfront park featuring picnic areas and fishing access. Conveniently situated for commuters, this home offers easy access to the Eastern Shore beaches, Washington, DC, and Baltimore—making it the perfect place to enjoy coastal living with city convenience. Don’t miss this exceptional opportunity! Seller will consider leasing the property to qualified tenants for $3000 per month plus $3000 security deposit.

109 Birch Rd, Stevensville

Listing courtesy of Five Star Real Estate. Contact:

$320,000

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

3 Beds ⋅ 2 Baths

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact: