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Welcome to Southwind, one of Kent Island's most desirable waterfront communities, where peaceful surroundings and an exceptional lifestyle come together. Perfectly positioned on 1.22 beautifully landscaped acres with water views, this inviting single-level home offers the comfort, space, and amenities you've been searching for. Inside, you'll find three spacious bedrooms and three beautifully updated full baths, creating a home that is both stylish and comfortable. Freshly painted throughout, with newly refinished hardwood floors and plush new carpeting in the bedrooms, every room feels bright, fresh, and move-in ready. The heart of the home is the welcoming kitchen, featuring gleaming granite countertops, crisp white cabinetry, a generous pantry with charming French doors, peninsula seating for casual meals and conversation, a vaulted breakfast area with a dramatic palladium window showcasing beautiful water views, and brand-new stainless steel range and refrigerator. Whether you're preparing dinner or gathering with family and friends, this space is designed to bring everyone together. The adjoining family room is warm and inviting, centered around a cozy propane fireplace and accented by custom built-in bookshelves that add both charm and functionality. A sliding glass door opens directly to the slate patio, creating an effortless connection between indoor and outdoor living. Just off the main living area, the light-filled dining room is surrounded by large windows that frame lovely water views, creating the perfect backdrop for everyday meals and special occasions. A versatile bonus sunroom offers even more living space and can easily serve as a cozy den, home office, or additional bedroom to fit your needs. Step outside to enjoy the fenced backyard and slate patio, where a remote-operated awning provides welcome shade at the touch of a button, making it the perfect spot for morning coffee, evening sunsets, or weekend barbecues. Car enthusiasts, hobbyists, and those needing extra space will appreciate the oversized four-car garage. Above, an expansive unfinished area offers endless possibilities. Already plumbed for a future bath, it's ready to become a guest suite, home office, recreation room, or whatever your imagination inspires. Energy efficiency is another standout feature, with owned solar panels and two Tesla Powerwall storage batteries helping to keep utility costs remarkably low while providing added peace of mind. Living in Southwind means more than owning a beautiful home—it's embracing a waterfront lifestyle. Residents enjoy access to the community boat launch, waterfront clubhouse, boat storage lot, pickleball and tennis courts, and scenic nature trail along the water. Whether you're launching your boat for a day on the Chesapeake Bay, enjoying an evening stroll by the shoreline, or simply relaxing at home while taking in the tranquil water views, this property offers the perfect blend of comfort, community, and coastal living.

2810 Harvest Ct, Chester

Listing courtesy of Blackwell Real Estate, LLC. Contact: 4432214120

$635,000

Mallard Run - This Colonial features 4 large-size bedrooms 2.5 bath home featuring 2,708 sq ft of living space. The open floor plan is great for entertaining, The luxury vinyl flooring is throughout the first floor. The kitchen is bright white cabinets with granite countertops also featuring an island and eat up bar area. You will also, enjoy the sunroom and beautiful backyard. The mud room and laundry off the two-car garage is great for storage. Close access to schools and local parks and trail, this is the location you have been looking for.

Mallard Run - This Colonial features 4 large-size bedrooms 2.5 bath home featuring 2,708 sq ft of living space. The open floor plan is great for entertaining, The luxury vinyl flooring is throughout the first floor. The kitchen is bright white cabinets with granite countertops also featuring an island and eat up bar area. You will also, enjoy the sunroom and beautiful backyard. The mud room and laundry off the two-car garage is great for storage. Close access to schools and local parks and trail, this is the location you have been looking for.

376 Web Foot Ln, Stevensville

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

$435,000

Grasonville - This home offers 3 bedroom and 3 baths located on 1.2 acres. The garage space is amazing for all of your projects. Featuring two garages, one car oversized attached is heated and with an oversized two car detached 24x 30 with heat and AC. The house roof is a 50-year shingle with about 7 years on it. You will enjoy the fall and the rest of the summer in the large screened in porch. NO Hoa or restrictions. This is the home you have been looking for. Call today for your showing appointment.

Grasonville - This home offers 3 bedroom and 3 baths located on 1.2 acres. The garage space is amazing for all of your projects. Featuring two garages, one car oversized attached is heated and with an oversized two car detached 24x 30 with heat and AC. The house roof is a 50-year shingle with about 7 years on it. You will enjoy the fall and the rest of the summer in the large screened in porch. NO Hoa or restrictions. This is the home you have been looking for. Call today for your showing appointment.

407 Sawmill Ln, Grasonville

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

$345,000

Welcome to 1609 Crab Alley Drive, a charming three-bedroom, one-and-a-half-bath rancher offering comfortable one-level living and lovely water views. Inside, hardwood flooring adds warmth and character, while the oversized picture window fills the front living room with natural light. The spacious backyard is made for summertime enjoyment, featuring an above-ground pool with plenty of additional room for entertaining, gardening, pets, or play. A large detached two-car garage provides exceptional space for vehicles, storage, hobbies, or a workshop. With its classic curb appeal, generous outdoor space, and convenient Chester location, this inviting home is ready for its next chapter.

Welcome to 1609 Crab Alley Drive, a charming three-bedroom, one-and-a-half-bath rancher offering comfortable one-level living and lovely water views. Inside, hardwood flooring adds warmth and character, while the oversized picture window fills the front living room with natural light. The spacious backyard is made for summertime enjoyment, featuring an above-ground pool with plenty of additional room for entertaining, gardening, pets, or play. A large detached two-car garage provides exceptional space for vehicles, storage, hobbies, or a workshop. With its classic curb appeal, generous outdoor space, and convenient Chester location, this inviting home is ready for its next chapter.

1609 Crab Alley Dr, Chester

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709

$349,000

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

123 Heath Rd, Chestertown

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

$345,600

Cutest little rancher in the cutest little town! Welcome to Queenstown! Walk to the bank, post office, restaurant, waterfront overlook or even the GOLF COURSE! Quaint smalltown living at its finest! Brand new composite deck boards and vinyl rails. Brand new paver walkway and steps being completed. Updated kitchen!!! Newer cabinets! Newer quartz countertops! Newer appliances! Newer LVP flooring! Newer fence! Nice corner lot with water views! Hardwood and ceramic floors. Easy commute on and off of 301 to Annapolis, Easton, or wherever!

3 Beds ⋅ 1 Baths

Cutest little rancher in the cutest little town! Welcome to Queenstown! Walk to the bank, post office, restaurant, waterfront overlook or even the GOLF COURSE! Quaint smalltown living at its finest! Brand new composite deck boards and vinyl rails. Brand new paver walkway and steps being completed. Updated kitchen!!! Newer cabinets! Newer quartz countertops! Newer appliances! Newer LVP flooring! Newer fence! Nice corner lot with water views! Hardwood and ceramic floors. Easy commute on and off of 301 to Annapolis, Easton, or wherever!

6808 Main St, Queenstown

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$382,750

OPEN HOUSE this Saturday 7/25 - 9am to 11am! ALL NEW Carpet & flooring, fresh custom paint, granite countertops and newer appliances! Welcome to one of the most desirable homes in the Bridgepointe community! This beautifully maintained END UNIT home offers added privacy, abundant natural light and a thoughtfully designed floor plan that perfectly blends comfort and convenience. Featuring one of the community's most sought after amenities... an ATTACHED GARAGE with interior access! This exceptional home also offers a first floor Primary bedroom & full bath, first floor laundry, making it ideal for guests, multigenerational living, a home office, or anyone seeking the convenience of main level living. Step inside to discover bright, inviting living spaces enhanced by the additional windows that only an end unit can provide. The open concept layout creates an effortless flow for both everyday living and entertaining. The well-appointed kitchen opens to the main living areas while the spacious bedrooms provide flexibility for family, guests, or work-from-home needs. Enjoy the best of low maintenance living in the highly desirable Bridgepointe community, with easy access to shopping, dining, parks, schools, marinas, and the Chesapeake Bay. Commuters will appreciate the close proximity to the Bay Bridge, Route 50, Annapolis and Maryland's Eastern Shore. Whether you are searching for a full-time residence or a weekend retreat, this exceptional home offers the perfect combination of location, lifestyle, and value.

OPEN HOUSE this Saturday 7/25 - 9am to 11am! ALL NEW Carpet & flooring, fresh custom paint, granite countertops and newer appliances! Welcome to one of the most desirable homes in the Bridgepointe community! This beautifully maintained END UNIT home offers added privacy, abundant natural light and a thoughtfully designed floor plan that perfectly blends comfort and convenience. Featuring one of the community's most sought after amenities... an ATTACHED GARAGE with interior access! This exceptional home also offers a first floor Primary bedroom & full bath, first floor laundry, making it ideal for guests, multigenerational living, a home office, or anyone seeking the convenience of main level living. Step inside to discover bright, inviting living spaces enhanced by the additional windows that only an end unit can provide. The open concept layout creates an effortless flow for both everyday living and entertaining. The well-appointed kitchen opens to the main living areas while the spacious bedrooms provide flexibility for family, guests, or work-from-home needs. Enjoy the best of low maintenance living in the highly desirable Bridgepointe community, with easy access to shopping, dining, parks, schools, marinas, and the Chesapeake Bay. Commuters will appreciate the close proximity to the Bay Bridge, Route 50, Annapolis and Maryland's Eastern Shore. Whether you are searching for a full-time residence or a weekend retreat, this exceptional home offers the perfect combination of location, lifestyle, and value.

2004 Bridgepointe Dr, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$989,000

Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has undergone a stunning renovation, creating a haven of luxury and serenity on a peaceful street. Every detail of this home has been impeccably updated, from the oversized windows to the modernized bathrooms. However, the true centerpiece is the fully equipped gourmet kitchen, a masterpiece of design. A magnificent 10-foot Quartz center island takes center stage, surrounded by pristine cabinets, state-of-the-art appliances, and exquisite marble countertops. To top it off, the kitchen also boasts its own wet bar with a built-in beverage cooler. The open-concept layout seamlessly connects the kitchen to the living space, with a mesmerizing wall of oversized windows that offer breathtaking views of the expansive waterfront and private pier. Convenience is a priority in this home, with a three-car pull-through garage and a pier equipped with boat lift as well as dual Jetski lift for easy access to the water. Outdoor enjoyment is a given, with two waterfront decks, a screened-in patio, and a private en-suite deck for moments of relaxation. Privacy and the feeling of island-style living are abundant here. Located in the heart of Kent Island, this property provides effortless access to luxury dining options, waterfront restaurants, lively dock bars, and island-style entertainment. All while, being just 2 miles away from the Chesapeake Bay Bridge means seamless travel by land or sea. Welcome to your dream home, here on Kent Island where tranquility and luxury converge with Maryland's Eastern Shore and the Chesapeake Bay.

5 Beds ⋅ 4 Baths

Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has undergone a stunning renovation, creating a haven of luxury and serenity on a peaceful street. Every detail of this home has been impeccably updated, from the oversized windows to the modernized bathrooms. However, the true centerpiece is the fully equipped gourmet kitchen, a masterpiece of design. A magnificent 10-foot Quartz center island takes center stage, surrounded by pristine cabinets, state-of-the-art appliances, and exquisite marble countertops. To top it off, the kitchen also boasts its own wet bar with a built-in beverage cooler. The open-concept layout seamlessly connects the kitchen to the living space, with a mesmerizing wall of oversized windows that offer breathtaking views of the expansive waterfront and private pier. Convenience is a priority in this home, with a three-car pull-through garage and a pier equipped with boat lift as well as dual Jetski lift for easy access to the water. Outdoor enjoyment is a given, with two waterfront decks, a screened-in patio, and a private en-suite deck for moments of relaxation. Privacy and the feeling of island-style living are abundant here. Located in the heart of Kent Island, this property provides effortless access to luxury dining options, waterfront restaurants, lively dock bars, and island-style entertainment. All while, being just 2 miles away from the Chesapeake Bay Bridge means seamless travel by land or sea. Welcome to your dream home, here on Kent Island where tranquility and luxury converge with Maryland's Eastern Shore and the Chesapeake Bay.

2702 Sherman Dr, Chester

Listing courtesy of Samson Properties. Contact: 7033788810

$589,000

Welcome Home to 729 Kimberly Way, nestled in the highly sought-after waterfront community of Cloverfields on Kent Island—where thoughtful updates, exceptional outdoor living, and versatile bonus space combine to create a home you’ll be proud to call your own. This beautifully maintained 4-bedroom, 2-bath raised rancher welcomes you with mature landscaping, vibrant flower beds, a spacious half-circle driveway, and outstanding curb appeal. The extended driveway leads to an oversized detached garage with generous storage above, offering endless potential to be finished into additional workspace, a private office, hobby room, or the perfect retreat to fit your lifestyle. Step into your own backyard oasis, thoughtfully designed for both entertaining and everyday enjoyment. Stamped concrete walkways and patios lead to an expansive two-tier deck, complemented by covered outdoor living space, mature trees for added privacy, and beautifully maintained landscaping that creates a peaceful setting. With ample parking and inviting outdoor spaces, this property is ideal for hosting family and friends or simply relaxing after a day on the water. Inside, you’ll find numerous updates and energy-efficient features throughout. The lower level offers a spacious family room centered around a charming wood-burning stove, creating a warm gathering place while helping reduce heating costs during the cooler months. Paired with the home’s highly efficient geothermal heating and cooling system—a rare and valuable feature on Maryland’s Eastern Shore—you’ll enjoy year-round comfort and exceptional energy savings. The lower level also features a full bathroom, welcoming tiled entry, and updated mechanicals, including a new water heater and new washer and dryer. Upstairs, engineered hardwood flooring flows throughout the main living areas, adding warmth and timeless character. The updated kitchen offers modern appliances and opens seamlessly to the dining area, where sliding glass doors lead to the expansive rear deck overlooking the private backyard. The upper level includes three comfortable bedrooms, including a spacious split primary suite with abundant closet space. The beautifully updated bathroom showcases ceramic tile flooring, an oversized tiled shower, and a relaxing soaking tub. Fresh paint, updated lighting, and meticulous care make this home truly move-in ready. Living in Cloverfields means enjoying some of Kent Island’s most desirable community amenities, including a private sandy beach, marina, boat ramp, fishing pier, swimming pool, clubhouse, playgrounds, and parks—all just minutes from the Chesapeake Bay Bridge, waterfront restaurants, shopping, and everything the Eastern Shore lifestyle has to offer. If you’ve been searching for a home that offers comfort, flexibility, energy efficiency, and an unbeatable waterfront community, 729 Kimberly Way is an opportunity you won’t want to miss.

4 Beds ⋅ 2 Baths

Welcome Home to 729 Kimberly Way, nestled in the highly sought-after waterfront community of Cloverfields on Kent Island—where thoughtful updates, exceptional outdoor living, and versatile bonus space combine to create a home you’ll be proud to call your own. This beautifully maintained 4-bedroom, 2-bath raised rancher welcomes you with mature landscaping, vibrant flower beds, a spacious half-circle driveway, and outstanding curb appeal. The extended driveway leads to an oversized detached garage with generous storage above, offering endless potential to be finished into additional workspace, a private office, hobby room, or the perfect retreat to fit your lifestyle. Step into your own backyard oasis, thoughtfully designed for both entertaining and everyday enjoyment. Stamped concrete walkways and patios lead to an expansive two-tier deck, complemented by covered outdoor living space, mature trees for added privacy, and beautifully maintained landscaping that creates a peaceful setting. With ample parking and inviting outdoor spaces, this property is ideal for hosting family and friends or simply relaxing after a day on the water. Inside, you’ll find numerous updates and energy-efficient features throughout. The lower level offers a spacious family room centered around a charming wood-burning stove, creating a warm gathering place while helping reduce heating costs during the cooler months. Paired with the home’s highly efficient geothermal heating and cooling system—a rare and valuable feature on Maryland’s Eastern Shore—you’ll enjoy year-round comfort and exceptional energy savings. The lower level also features a full bathroom, welcoming tiled entry, and updated mechanicals, including a new water heater and new washer and dryer. Upstairs, engineered hardwood flooring flows throughout the main living areas, adding warmth and timeless character. The updated kitchen offers modern appliances and opens seamlessly to the dining area, where sliding glass doors lead to the expansive rear deck overlooking the private backyard. The upper level includes three comfortable bedrooms, including a spacious split primary suite with abundant closet space. The beautifully updated bathroom showcases ceramic tile flooring, an oversized tiled shower, and a relaxing soaking tub. Fresh paint, updated lighting, and meticulous care make this home truly move-in ready. Living in Cloverfields means enjoying some of Kent Island’s most desirable community amenities, including a private sandy beach, marina, boat ramp, fishing pier, swimming pool, clubhouse, playgrounds, and parks—all just minutes from the Chesapeake Bay Bridge, waterfront restaurants, shopping, and everything the Eastern Shore lifestyle has to offer. If you’ve been searching for a home that offers comfort, flexibility, energy efficiency, and an unbeatable waterfront community, 729 Kimberly Way is an opportunity you won’t want to miss.

729 Kimberly Way, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810

$2,850,000

Set on Forty Five picturesque acres of prime agricultural land with extensive tillable acreage, this exceptional Five bedroom, Four and one half bath brick colonial blends timeless design with modern versatility and waterfront charm. Privately situated on a quiet cove just off the mouth of the Chester River, the property offers a rare combination of space, functionality, and lifestyle appeal. Inside, the home features a thoughtfully designed layout ideal for both everyday living and entertaining. A main-level en-suite provides excellent flexibility for multi-generational living or private guest quarters, while an additional upper-level en-suite enhances comfort and convenience for visitors. The spacious primary suite serves as a true retreat, complemented by well-proportioned secondary bedrooms and multiple full baths. Refined living spaces include a formal dining room, a dedicated home office perfect for remote work, and an inviting screened porch overlooking the water—an ideal setting to relax and take in the tranquil views. The nearly fully finished basement expands your living options with generous space for recreation, hobbies, or a workshop. Recent upgrades—including a new roof and septic system—offering peace of mind, while the 2-zone HVAC system ensures efficient year-round comfort. Outdoors, enjoy the in-ground pool surrounded by a patio, perfect for entertaining or unwinding, along with open acreage that offers endless possibilities for farming, equestrian use, or a private rural lifestyle. Complete with a Twocar garage and located in a highly desirable waterfront setting, this property presents a rare opportunity to own a versatile estate that balances luxury living, scenic beauty, and agricultural potential.

5 Beds ⋅ 5 Baths

Set on Forty Five picturesque acres of prime agricultural land with extensive tillable acreage, this exceptional Five bedroom, Four and one half bath brick colonial blends timeless design with modern versatility and waterfront charm. Privately situated on a quiet cove just off the mouth of the Chester River, the property offers a rare combination of space, functionality, and lifestyle appeal. Inside, the home features a thoughtfully designed layout ideal for both everyday living and entertaining. A main-level en-suite provides excellent flexibility for multi-generational living or private guest quarters, while an additional upper-level en-suite enhances comfort and convenience for visitors. The spacious primary suite serves as a true retreat, complemented by well-proportioned secondary bedrooms and multiple full baths. Refined living spaces include a formal dining room, a dedicated home office perfect for remote work, and an inviting screened porch overlooking the water—an ideal setting to relax and take in the tranquil views. The nearly fully finished basement expands your living options with generous space for recreation, hobbies, or a workshop. Recent upgrades—including a new roof and septic system—offering peace of mind, while the 2-zone HVAC system ensures efficient year-round comfort. Outdoors, enjoy the in-ground pool surrounded by a patio, perfect for entertaining or unwinding, along with open acreage that offers endless possibilities for farming, equestrian use, or a private rural lifestyle. Complete with a Twocar garage and located in a highly desirable waterfront setting, this property presents a rare opportunity to own a versatile estate that balances luxury living, scenic beauty, and agricultural potential.

1810 Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435

$359,000

Live like you're on vacation every day in the highly desirable Queen's Landing community on Kent Island! Nestled along the Chester River, this charming lake-front townhome offers the perfect blend of comfort, style, and resort-style living. You'll love the gorgeous remodeled kitchen featuring granite countertops, a large center island, breakfast bar, custom built-ins, and a pass-through to the living room—perfect for cooking, entertaining, and everyday living! The spacious living room features a cozy fireplace and opens to a beautiful enclosed pond-front porch where you can relax with your morning coffee while taking in the peaceful water views. The primary suite offers incredible lake views and a private bath, plus you'll find two additional bedrooms and the convenience of second-floor laundry. Enjoy the incredible community amenities: Community pool, Pickleball & tennis courts, Fitness center, Clubhouse, Adjacent to Castle Harbor Marina Queen's Landing on Kent Island is the perfect getaway—whether you're looking for a second home or a primary residence. Enjoy resort-style living with beautiful surroundings and all the charm of the Eastern Shore.

Live like you're on vacation every day in the highly desirable Queen's Landing community on Kent Island! Nestled along the Chester River, this charming lake-front townhome offers the perfect blend of comfort, style, and resort-style living. You'll love the gorgeous remodeled kitchen featuring granite countertops, a large center island, breakfast bar, custom built-ins, and a pass-through to the living room—perfect for cooking, entertaining, and everyday living! The spacious living room features a cozy fireplace and opens to a beautiful enclosed pond-front porch where you can relax with your morning coffee while taking in the peaceful water views. The primary suite offers incredible lake views and a private bath, plus you'll find two additional bedrooms and the convenience of second-floor laundry. Enjoy the incredible community amenities: Community pool, Pickleball & tennis courts, Fitness center, Clubhouse, Adjacent to Castle Harbor Marina Queen's Landing on Kent Island is the perfect getaway—whether you're looking for a second home or a primary residence. Enjoy resort-style living with beautiful surroundings and all the charm of the Eastern Shore.

29 Queen Mary Ct, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333

$162,000

Bring your dream home, and your builder to this beautiful 1-acre lot! This perc-approved homesite allows for a basement, giving you the flexibility to design the home you've always envisioned. Enjoy the opportunity to build in a peaceful setting while creating a home tailored to your lifestyle.

441 Eagle Manor Dr, Church Hill

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

$999,990

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

110 Boatswain Way Unit #3044, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$600,000

Welcome to one of Sudlersville's most extraordinary heritage homes, a magnificent Queen Anne Victorian that beautifully honors its historic character while embracing the comforts of modern living. Following an extensive 2019 renovation that left virtually no system untouched, this remarkable residence has been thoughtfully reimagined for today's lifestyle while preserving the timeless architectural details that make it truly one of a kind. Set on more than an acre beneath majestic centuries-old shade trees, this magical family estate commands attention with its soaring turret, five striking bay windows, and deep, sweeping wraparound porch that invites you to slow down and savor every season. Overlooking the neighborhood park, the setting is as enchanting as the home itself, nestled within the quintessential Hallmark town of Sudlersville, where the historic train station now serves as a museum and the soft rumble of the grain train passing through town a few times each week provides a nostalgic reminder of the community's rich heritage. Inside, soaring ceilings, exquisite millwork, and an impressive foyer introduce an unexpectedly open floor plan designed for both gracious entertaining and everyday living. The expansive kitchen is a true gathering place, featuring stunning custom cabinetry that extends to the ceiling with thoughtfully designed pull-out drawers, a dramatic designer backsplash, updated stainless steel appliances, many with transferable warranties, and a large picture window above the sink that fills the space with natural light. The kitchen flows seamlessly into the dining room, beautifully nestled within one of the home's signature bay windows. The adjoining family room creates an airy, connected living space rarely found in historic homes, while multiple rooms open directly onto the wraparound porch, blurring the line between indoor and outdoor living. A dedicated office surrounded by windows offers an inspiring workspace, and the butler's pantry with wet bar provides the perfect staging area for effortless entertaining on the porch and patios. The main-level primary suite offers exceptional convenience with a spacious ensuite bath featuring a soaking tub and separate shower, while a powder room completes the first floor. Upstairs, four additional bedrooms include a private ensuite guest suite and a beautifully appointed hall bath. Fresh new carpeting enhances the upper-level bedrooms, while two of the bedrooms are graced by the home's distinctive bay window bump-outs, creating expansive sitting areas bathed in natural light and showcasing the architectural character that makes this residence so special. A walk-up third floor offers abundant storage along with the enchanting turret room, an unforgettable space ready to become a library, reading retreat, artist's studio, or simply a breathtaking lookout over the surrounding landscape. The immaculate cellar provides exceptional storage, while the park-like grounds are designed for year-round enjoyment with patios, arbors, expansive lawns, a welcoming fire pit tucked beneath towering centuries-old shade trees, and two substantial outbuildings, including a garage and a detached studio currently used as a fitness space. Rich in history yet thoughtfully transformed for thoroughly modern living - including a Level 2 EV Tesla charger! This spectacular Queen Anne Victorian is far more than a home, it is a once-in-a-lifetime opportunity to become the next steward of one of Sudlersville's most treasured residences.

5 Beds ⋅ 4 Baths

Welcome to one of Sudlersville's most extraordinary heritage homes, a magnificent Queen Anne Victorian that beautifully honors its historic character while embracing the comforts of modern living. Following an extensive 2019 renovation that left virtually no system untouched, this remarkable residence has been thoughtfully reimagined for today's lifestyle while preserving the timeless architectural details that make it truly one of a kind. Set on more than an acre beneath majestic centuries-old shade trees, this magical family estate commands attention with its soaring turret, five striking bay windows, and deep, sweeping wraparound porch that invites you to slow down and savor every season. Overlooking the neighborhood park, the setting is as enchanting as the home itself, nestled within the quintessential Hallmark town of Sudlersville, where the historic train station now serves as a museum and the soft rumble of the grain train passing through town a few times each week provides a nostalgic reminder of the community's rich heritage. Inside, soaring ceilings, exquisite millwork, and an impressive foyer introduce an unexpectedly open floor plan designed for both gracious entertaining and everyday living. The expansive kitchen is a true gathering place, featuring stunning custom cabinetry that extends to the ceiling with thoughtfully designed pull-out drawers, a dramatic designer backsplash, updated stainless steel appliances, many with transferable warranties, and a large picture window above the sink that fills the space with natural light. The kitchen flows seamlessly into the dining room, beautifully nestled within one of the home's signature bay windows. The adjoining family room creates an airy, connected living space rarely found in historic homes, while multiple rooms open directly onto the wraparound porch, blurring the line between indoor and outdoor living. A dedicated office surrounded by windows offers an inspiring workspace, and the butler's pantry with wet bar provides the perfect staging area for effortless entertaining on the porch and patios. The main-level primary suite offers exceptional convenience with a spacious ensuite bath featuring a soaking tub and separate shower, while a powder room completes the first floor. Upstairs, four additional bedrooms include a private ensuite guest suite and a beautifully appointed hall bath. Fresh new carpeting enhances the upper-level bedrooms, while two of the bedrooms are graced by the home's distinctive bay window bump-outs, creating expansive sitting areas bathed in natural light and showcasing the architectural character that makes this residence so special. A walk-up third floor offers abundant storage along with the enchanting turret room, an unforgettable space ready to become a library, reading retreat, artist's studio, or simply a breathtaking lookout over the surrounding landscape. The immaculate cellar provides exceptional storage, while the park-like grounds are designed for year-round enjoyment with patios, arbors, expansive lawns, a welcoming fire pit tucked beneath towering centuries-old shade trees, and two substantial outbuildings, including a garage and a detached studio currently used as a fitness space. Rich in history yet thoughtfully transformed for thoroughly modern living - including a Level 2 EV Tesla charger! This spectacular Queen Anne Victorian is far more than a home, it is a once-in-a-lifetime opportunity to become the next steward of one of Sudlersville's most treasured residences.

108 Maple Ave, Sudlersville

Listing courtesy of Northrop Realty. Contact: (302) 947-9100

$629,990

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

2 Beds ⋅ 3 Baths

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2911, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$974,990

Welcome to the Tuscaloosa, a beautifully designed home that blends an open-concept floorplan with warm Farmhouse-inspired style, creating the perfect balance of comfort and functionality. Projected for November 2026 settlement, this spacious home features 5 bedrooms, 4.5 bathrooms, and a 3-car garage, offering plenty of room for everyday living, entertaining, and hosting overnight guests. Designed with versatility in mind, the Tuscaloosa includes two primary suites, making it an ideal layout for multi-generational living or accommodating long-term guests. The inviting fireplace serves as a cozy focal point for the main living area, while the screened patio provides the perfect outdoor retreat for enjoying fresh air in comfort throughout the seasons. Thoughtful design and quality craftsmanship come together to create a home that is both stylish and functional. For a complete list of included features and finishes, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

5 Beds ⋅ 5 Baths

Welcome to the Tuscaloosa, a beautifully designed home that blends an open-concept floorplan with warm Farmhouse-inspired style, creating the perfect balance of comfort and functionality. Projected for November 2026 settlement, this spacious home features 5 bedrooms, 4.5 bathrooms, and a 3-car garage, offering plenty of room for everyday living, entertaining, and hosting overnight guests. Designed with versatility in mind, the Tuscaloosa includes two primary suites, making it an ideal layout for multi-generational living or accommodating long-term guests. The inviting fireplace serves as a cozy focal point for the main living area, while the screened patio provides the perfect outdoor retreat for enjoying fresh air in comfort throughout the seasons. Thoughtful design and quality craftsmanship come together to create a home that is both stylish and functional. For a complete list of included features and finishes, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

323 Kingfisher Ln, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$675,000

Welcome to 144 Wye Knot Road, where peaceful country living meets everyday convenience. Nestled on 3 private, level acres, this spacious cape cod offers the perfect blend of comfort, functionality, and open space, all within easy reach of Easton, Annapolis, the Bay Bridge, and major commuter routes. A tree-lined paved driveway welcomes you home, while the classic exterior, complete with a full front porch, dormer accents, and an attached side-load two-car garage, creates timeless curb appeal. Inside, you'll find over 2,200 square feet of thoughtfully designed living space featuring four bedrooms, two-and-a-half bathrooms, and an ideal floor plan for both everyday living and entertaining. Formal living and dining rooms flank the welcoming foyer, while the rear of the home opens to a dramatic family room with soaring cathedral ceilings, abundant natural light, rich wood flooring, and a cozy gas fireplace. The kitchen serves as the heart of the home, offering Corian countertops, stainless steel appliances, a center island, generous cabinetry, and an informal dining area overlooking the backyard. Step outside to the spacious deck, perfect for morning coffee, summer barbecues, or simply relaxing while taking in the peaceful surroundings. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite. The finished bonus room above the garage provides exceptional flexibility and is ideal for a recreation room, home office, fitness room, playroom, or 4th bedroom/2nd primary suite. Additional features include dual-zone HVAC (replaced within the last 10 years), a tankless gas water heater (replaced within the last 10 years) and an EV charger-ready garage. The true highlight of this property is the land. Level, usable acreage like this is increasingly difficult to find and provides endless opportunities for gardening, recreation, entertaining, future outdoor amenities, or simply enjoying the peace, privacy, and beauty of country living. If you've been searching for a home that offers room to breathe without sacrificing convenience, 144 Wye Knot Road is an exceptional opportunity to enjoy the best of Maryland's Eastern Shore lifestyle.

Welcome to 144 Wye Knot Road, where peaceful country living meets everyday convenience. Nestled on 3 private, level acres, this spacious cape cod offers the perfect blend of comfort, functionality, and open space, all within easy reach of Easton, Annapolis, the Bay Bridge, and major commuter routes. A tree-lined paved driveway welcomes you home, while the classic exterior, complete with a full front porch, dormer accents, and an attached side-load two-car garage, creates timeless curb appeal. Inside, you'll find over 2,200 square feet of thoughtfully designed living space featuring four bedrooms, two-and-a-half bathrooms, and an ideal floor plan for both everyday living and entertaining. Formal living and dining rooms flank the welcoming foyer, while the rear of the home opens to a dramatic family room with soaring cathedral ceilings, abundant natural light, rich wood flooring, and a cozy gas fireplace. The kitchen serves as the heart of the home, offering Corian countertops, stainless steel appliances, a center island, generous cabinetry, and an informal dining area overlooking the backyard. Step outside to the spacious deck, perfect for morning coffee, summer barbecues, or simply relaxing while taking in the peaceful surroundings. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite. The finished bonus room above the garage provides exceptional flexibility and is ideal for a recreation room, home office, fitness room, playroom, or 4th bedroom/2nd primary suite. Additional features include dual-zone HVAC (replaced within the last 10 years), a tankless gas water heater (replaced within the last 10 years) and an EV charger-ready garage. The true highlight of this property is the land. Level, usable acreage like this is increasingly difficult to find and provides endless opportunities for gardening, recreation, entertaining, future outdoor amenities, or simply enjoying the peace, privacy, and beauty of country living. If you've been searching for a home that offers room to breathe without sacrificing convenience, 144 Wye Knot Road is an exceptional opportunity to enjoy the best of Maryland's Eastern Shore lifestyle.

144 Wye Knot Rd, Queenstown

Listing courtesy of RE/MAX Leading Edge. Contact:

$1,300,000

Coming soon to Kent Island Estates — a rare opportunity to own directly on the Eastern Bay. This 5-bedroom, 3.5-bath Coastal-style home offers 2,704 square feet of finished living space across three levels, with soaring high ceilings, rich hardwood floors, and crown molding and wainscotting carrying throughout. The gourmet kitchen features upgraded countertops and premium appliances, with a breakfast area perfect for casual mornings, plus a fireplace in the main living area for cooler evenings. Professional Photos to come. Multiple bedrooms open directly onto a screened-in porch and private balconies, framing sweeping views of the Chesapeake Bay from nearly every angle. Step outside to your own private pier and dock, putting boating, fishing, and bay access just steps from the back door — while an in-ground pool adds resort-style living to your own backyard. Pella double-pane windows fill the home with natural light while keeping energy costs in check. Set on a 0.32-acre lot with no HOA, this home sits in the sought-after Kent Island Estates community, with access to a neighborhood park, the South Kent Island Trail, and quick proximity to local restaurants, grocery stores, and the Bay Bridge for an easy commute to Annapolis. Waterfront opportunities like this on the Eastern Bay are rare — don't miss your chance.

5 Beds ⋅ 4 Baths

Coming soon to Kent Island Estates — a rare opportunity to own directly on the Eastern Bay. This 5-bedroom, 3.5-bath Coastal-style home offers 2,704 square feet of finished living space across three levels, with soaring high ceilings, rich hardwood floors, and crown molding and wainscotting carrying throughout. The gourmet kitchen features upgraded countertops and premium appliances, with a breakfast area perfect for casual mornings, plus a fireplace in the main living area for cooler evenings. Professional Photos to come. Multiple bedrooms open directly onto a screened-in porch and private balconies, framing sweeping views of the Chesapeake Bay from nearly every angle. Step outside to your own private pier and dock, putting boating, fishing, and bay access just steps from the back door — while an in-ground pool adds resort-style living to your own backyard. Pella double-pane windows fill the home with natural light while keeping energy costs in check. Set on a 0.32-acre lot with no HOA, this home sits in the sought-after Kent Island Estates community, with access to a neighborhood park, the South Kent Island Trail, and quick proximity to local restaurants, grocery stores, and the Bay Bridge for an easy commute to Annapolis. Waterfront opportunities like this on the Eastern Bay are rare — don't miss your chance.

366 Queen Anne Rd, Stevensville

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

$600,000

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!

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: 4435741600

$789,990

Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors—perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner’s suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner’s bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors—perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner’s suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner’s bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

723 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$839,990

Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors—perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner’s suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner’s bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors—perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner’s suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner’s bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

715 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$2,400,000

Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step outside to your private oasis, where a concrete pool invites relaxation amidst lush landscaping on a generous 1.2-acre lot that includes a covered built in Lynx grill and bar seating. Enjoy direct access to Cox Creek, complete with a private dock for fishing, kayaking, or simply soaking in the serene water views. With a double sided fireplace and three tankless water heater, this home combines elegance with modern convenience, making it a true sanctuary. The main living room features sky high ceilings and a wet bar making hosting a snap and flows into the added sunroom that features heated tile flooring. And the three season room off the back is the perfect gathering space with a wall of sliders to maximize the view. Meticulously maintained and thoroughy enjoyed by the original owners. The expansive rear yard and rip-rap shoreline enhance the outdoor experience, while the community amenities, including a beach, tennis/basketball courts, and fishing pier and boat launch, offer an exclusive lifestyle on Maryland's Eastern Shore.

4 Beds ⋅ 4 Baths

Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step outside to your private oasis, where a concrete pool invites relaxation amidst lush landscaping on a generous 1.2-acre lot that includes a covered built in Lynx grill and bar seating. Enjoy direct access to Cox Creek, complete with a private dock for fishing, kayaking, or simply soaking in the serene water views. With a double sided fireplace and three tankless water heater, this home combines elegance with modern convenience, making it a true sanctuary. The main living room features sky high ceilings and a wet bar making hosting a snap and flows into the added sunroom that features heated tile flooring. And the three season room off the back is the perfect gathering space with a wall of sliders to maximize the view. Meticulously maintained and thoroughy enjoyed by the original owners. The expansive rear yard and rip-rap shoreline enhance the outdoor experience, while the community amenities, including a beach, tennis/basketball courts, and fishing pier and boat launch, offer an exclusive lifestyle on Maryland's Eastern Shore.

2882 Cox Neck Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250

$929,990

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

532 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$829,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

2 Beds ⋅ 3 Baths

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2933, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$869,990

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2921, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$210,000

Welcome to 3701 Barclay Rd, a fantastic opportunity to own a 3-bedroom, 2-bath manufactured home on nearly half an acre in the peaceful countryside of Queen Anne's County. Built in 2004, this property offers a spacious open floor plan ready for your vision and personal touch. Inside, you'll find a generously sized living area that flows into the kitchen featuring a center island, making it an ideal layout for everyday living and entertaining. Step outside to enjoy the rear porch overlooking the backyard, complete with an above-ground pool and a shed/outbuilding for additional storage. Whether you're an investor searching for your next value-add project or a homeowner looking to build equity while creating your dream home, this property is packed with potential. With some updates and repairs, this home could truly shine. Enjoy the privacy and charm of country living while remaining within easy reach of nearby towns, shopping, and commuter routes. Located in the desirable Queen Anne's County Public School District. Property is being sold strictly as-is.

Welcome to 3701 Barclay Rd, a fantastic opportunity to own a 3-bedroom, 2-bath manufactured home on nearly half an acre in the peaceful countryside of Queen Anne's County. Built in 2004, this property offers a spacious open floor plan ready for your vision and personal touch. Inside, you'll find a generously sized living area that flows into the kitchen featuring a center island, making it an ideal layout for everyday living and entertaining. Step outside to enjoy the rear porch overlooking the backyard, complete with an above-ground pool and a shed/outbuilding for additional storage. Whether you're an investor searching for your next value-add project or a homeowner looking to build equity while creating your dream home, this property is packed with potential. With some updates and repairs, this home could truly shine. Enjoy the privacy and charm of country living while remaining within easy reach of nearby towns, shopping, and commuter routes. Located in the desirable Queen Anne's County Public School District. Property is being sold strictly as-is.

3701 Barclay Rd, Marydel

Listing courtesy of LPT Realty, LLC. Contact: 8773662213

$779,900

2 Beds ⋅ 2 Baths

169 Harrier Way, Chester

Listing courtesy of CENTURY 21 New Millennium. Contact: 3015198100

$400,000

Opportunity meets location at this charming 1891 farmhouse situated on a spacious ¾-acre lot just a few short miles off 301 . Located within the Village Center District, this unique property offers the flexibility and visibility that entrepreneurs, tradespeople, hobbyists, and investors have been searching for. And NO TOWN TAXES. The home features 3 bedrooms and 2 full baths, blending historic character with thoughtful updates including granite countertops and stainless steel appliances. Outside, the standout feature is the impressive 32' x 24' detached garage with two 10' x 10' doors, providing ample space for a workshop, storage, equipment, vehicles, or business operations. Whether you're looking for a place to call home, a property with room to grow your business, or a combination of both, the possibilities here are hard to find. Enjoy the convenience of being just minutes from downtown Centreville, schools, shopping, dining, and major commuter routes while maintaining the space and flexibility that only a property like this can provide. Bring your vision and explore the potential of this rare Village Center opportunity. Buyers to complete their own due diligence for permitted use of the property and fees.

1645 Ruthsburg Rd, Centreville

Listing courtesy of Samson Properties. Contact: 7033788810

$749,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private workspace. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with seat and handheld shower wand, double sinks, and quartz countertops for added convenience and style. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

2 Beds ⋅ 3 Baths

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private workspace. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with seat and handheld shower wand, double sinks, and quartz countertops for added convenience and style. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

110 Boatswain Way Unit #3042, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$929,990

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.