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Fantastic Eastern Bay waterview from this wonderful Kent Island, 3 bedroom, 1.5 bathroom Ranch/Rambler in Romancoke on the Bay, with a near half acre. This cute home will surprise you with how spacious it is on the inside! Stepping in the front door, you'll notice the LVP flooring throughout the entire space. The front living area is quiet and cozy and faces the Eastern Bay water view! The open kitchen has stainless steel appliances and opens to the spacious dining room. Off the dining room you'll find the fantastic great room, perfect for large gatherings and plenty of cozy furniture. The sliders in the great room lead to a covered deck and patio centered on the fully fenced backyard. A stone pathway leads to a shed with electric. Back inside, down the hall from the kitchen is the remodeled full bath and the 3 bedrooms, two of which connect to a half bath. The property also offers an oversized attached single car garage, a fully encapsulated crawlspace, fresh paint throughout, established sunny raised garden beds, beautifully green spacious back yard (one side is fully treelined) and a circle driveway out front providing plenty of parking. Last but not least, the wide-open water view visible from the living room and two bedrooms! Romancoke on the Bay has wonderful amenities, including a Community Center that hosts regular events and can be rented out, a Boat Ramp, a Pier, a Beach and a Tot-Lot, all located right at the end of Allegany Rd. The Romancoke Pier is just up the street and so is the start of the South Island Trail which runs for miles through the trees and fields of Southern Kent Island. A list of updates follows. Don't miss this one! It is a perfect gem on Kent Island! Crawlspace encapsulated 2025, New sump pump 2025, New well pump 2026, New roof 2013, New HVAC 2013, SKI Sewer connected, New hot water heater 2016, New appliances 2016, Full bathroom renovation 2017

202 Allegany Rd, Stevensville

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

$609,990

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.

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 #2912, Chester

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

$399,000

Waterfront Living on Thompson Creek – Rare End-Unit Townhome Fantastic opportunity to own an end-unit waterfront townhome with direct views of Thompson Creek, complete with an assigned pier featuring power and water. Inside, gleaming hardwood floors flow through the kitchen and living room. The main level offers a convenient bedroom, while upstairs you'll find a huge loft-style primary suite complete with a spacious primary bathroom featuring an oversized walk-in shower and an equally impressive walk-in closet. A versatile bonus room offers flexibility as a 3rd bedroom or home office. The kitchen offers ample counter space and storage alongside a large dining area, perfect for entertaining. Step outside to a spacious deck to soak in the water views, plus a second private balcony off the primary bedroom. With western exposure, enjoy breathtaking sunsets over the creek every evening. The HOA maintains the pier as well as all exterior upkeep of the home, including the roof and siding, offering true low-maintenance waterfront living. Ideally located on Kent Island, just a half mile to Route 50 and minutes to two shopping centers featuring Food Lion, Target, and a variety of restaurants. Incredible value at $399,000 for waterfront living with a private pier. Furnishings are available for purchase separately, excluding personal items.

2 Beds ⋅ 2 Baths

Waterfront Living on Thompson Creek – Rare End-Unit Townhome Fantastic opportunity to own an end-unit waterfront townhome with direct views of Thompson Creek, complete with an assigned pier featuring power and water. Inside, gleaming hardwood floors flow through the kitchen and living room. The main level offers a convenient bedroom, while upstairs you'll find a huge loft-style primary suite complete with a spacious primary bathroom featuring an oversized walk-in shower and an equally impressive walk-in closet. A versatile bonus room offers flexibility as a 3rd bedroom or home office. The kitchen offers ample counter space and storage alongside a large dining area, perfect for entertaining. Step outside to a spacious deck to soak in the water views, plus a second private balcony off the primary bedroom. With western exposure, enjoy breathtaking sunsets over the creek every evening. The HOA maintains the pier as well as all exterior upkeep of the home, including the roof and siding, offering true low-maintenance waterfront living. Ideally located on Kent Island, just a half mile to Route 50 and minutes to two shopping centers featuring Food Lion, Target, and a variety of restaurants. Incredible value at $399,000 for waterfront living with a private pier. Furnishings are available for purchase separately, excluding personal items.

101 Marion Quimby Dr, Stevensville

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

$989,800

Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main living areas and the luxurious primary suite. Designed for both luxury living and entertaining, the open floor plan features 7-inch wide plank flooring, a gas fireplace, entry-level guest suite, and high-end finishes throughout. The gourmet kitchen is the heart of the home, complete with shaker-style cabinetry, quartz countertops, an oversized island, premium ZLINE stainless steel appliances, upgraded custom lighting, and expansive water views. Upstairs, the spacious primary suite offers a peaceful waterfront retreat with a spa-inspired bath featuring a 6-foot tiled walk-in shower with dual shower heads, a built-in bench, double vanities, and generous closet space. Bedroom-level laundry and beautifully finished bathrooms with tile flooring add everyday convenience. Outdoor living is just as impressive, with an expansive rear deck and covered patio overlooking the creek—perfect for enjoying sunrises over the water or relaxing while watching local wildlife. Adding to the sense of privacy, approximately 181 acres of rural land zoned "Countryside District" stretch across the shoreline on the opposite side, preserving the natural views with protected land. For those who enjoy life on the water, this location is hard to beat. Launch a kayak, paddleboard, or small boat from your backyard and reach the Chester River in approximately one mile, with the Chesapeake Bay just 5 to 6 water miles beyond. Enjoy quick access to bay boating while returning home to the calm waters, privacy, and natural beauty of a protected creek. Combining quality craftsmanship, upscale finishes, and an exceptional waterfront setting, this newly completed home offers a rare opportunity to enjoy the best of Maryland's Eastern Shore lifestyle!

5 Beds ⋅ 4 Baths

Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main living areas and the luxurious primary suite. Designed for both luxury living and entertaining, the open floor plan features 7-inch wide plank flooring, a gas fireplace, entry-level guest suite, and high-end finishes throughout. The gourmet kitchen is the heart of the home, complete with shaker-style cabinetry, quartz countertops, an oversized island, premium ZLINE stainless steel appliances, upgraded custom lighting, and expansive water views. Upstairs, the spacious primary suite offers a peaceful waterfront retreat with a spa-inspired bath featuring a 6-foot tiled walk-in shower with dual shower heads, a built-in bench, double vanities, and generous closet space. Bedroom-level laundry and beautifully finished bathrooms with tile flooring add everyday convenience. Outdoor living is just as impressive, with an expansive rear deck and covered patio overlooking the creek—perfect for enjoying sunrises over the water or relaxing while watching local wildlife. Adding to the sense of privacy, approximately 181 acres of rural land zoned "Countryside District" stretch across the shoreline on the opposite side, preserving the natural views with protected land. For those who enjoy life on the water, this location is hard to beat. Launch a kayak, paddleboard, or small boat from your backyard and reach the Chester River in approximately one mile, with the Chesapeake Bay just 5 to 6 water miles beyond. Enjoy quick access to bay boating while returning home to the calm waters, privacy, and natural beauty of a protected creek. Combining quality craftsmanship, upscale finishes, and an exceptional waterfront setting, this newly completed home offers a rare opportunity to enjoy the best of Maryland's Eastern Shore lifestyle!

203 Riverside Dr, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010

$749,900

Nestled within the prestigious Oyster Cove community, this exquisite 3rd floor Penthouse corner residence offers a harmonious blend of luxury and comfort, perfectly situated along the serene Kent Narrows/ Prospect bay. Served by elevator, the contemporary architectural style is complemented by high-end finishes throughout, including luxury vinyl plank flooring and elegant built-ins that enhance the open floor plan. Step inside to discover a spacious family room that seamlessly connects to a gourmet kitchen, featuring upgraded countertops and modern appliances, including a sleek electric range and a convenient dishwasher. The inviting breakfast area is perfect for casual dining, while the primary bath offers a private retreat with sophisticated fixtures. Enjoy the tranquility of river views from your porch, where you can unwind and soak in the picturesque surroundings. The property boasts deeded private 40 foot boat slip, ideal for boating enthusiasts, and a community pool for leisurely afternoons. Additional amenities include a gated entrance, ensuring privacy and security, along with beautifully maintained common grounds and walking paths. With three generously sized bedrooms and a cozy electric fireplace, this home is designed for both relaxation and entertaining. The community offers a wealth of recreational options, including tennis courts, pickle ball and picnic areas, enhancing the luxurious lifestyle that Oyster Cove provides. Experience the ultimate in waterfront living, where every detail has been thoughtfully curated for your enjoyment.

Nestled within the prestigious Oyster Cove community, this exquisite 3rd floor Penthouse corner residence offers a harmonious blend of luxury and comfort, perfectly situated along the serene Kent Narrows/ Prospect bay. Served by elevator, the contemporary architectural style is complemented by high-end finishes throughout, including luxury vinyl plank flooring and elegant built-ins that enhance the open floor plan. Step inside to discover a spacious family room that seamlessly connects to a gourmet kitchen, featuring upgraded countertops and modern appliances, including a sleek electric range and a convenient dishwasher. The inviting breakfast area is perfect for casual dining, while the primary bath offers a private retreat with sophisticated fixtures. Enjoy the tranquility of river views from your porch, where you can unwind and soak in the picturesque surroundings. The property boasts deeded private 40 foot boat slip, ideal for boating enthusiasts, and a community pool for leisurely afternoons. Additional amenities include a gated entrance, ensuring privacy and security, along with beautifully maintained common grounds and walking paths. With three generously sized bedrooms and a cozy electric fireplace, this home is designed for both relaxation and entertaining. The community offers a wealth of recreational options, including tennis courts, pickle ball and picnic areas, enhancing the luxurious lifestyle that Oyster Cove provides. Experience the ultimate in waterfront living, where every detail has been thoughtfully curated for your enjoyment.

130 Oyster Cove Dr Unit #130, Grasonville

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

$929,990

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.

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 #2943, 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.

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 #2932, Chester

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

$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

$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

$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

$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.

3 Beds ⋅ 3 Baths

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

$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.

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

$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.

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

$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.

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

$199,900

Nestled along the water's edge, this waterfront opportunity offers a canvas to create your own Eastern Shore retreat. Whether you choose to renovate the existing 3BR cottage or build on the existing foundation there is plenty of potential. Buyer to confirm building restrictions with the county. This property features a new deep well, new well pump, and new septic holding tanks in 2026. The existing interior of the home has been taken down to the framing and includes 100-amp electrical service, providing a solid starting point for your vision. Outdoor enthusiasts will enjoy everything this property has to offer. Fish for perch, bass, catfish, and snakeheads, or spend the day crabbing from your shoreline. Waterfowl hunters will enjoy the existing duck blind, while everyone will appreciate the stunning sunsets overlooking the water. Whether you're looking for a peaceful weekend escape, a hunting and fishing camp, or the site of your future waterfront cottage, this property offers an opportunity that's becoming increasingly difficult to find.

Nestled along the water's edge, this waterfront opportunity offers a canvas to create your own Eastern Shore retreat. Whether you choose to renovate the existing 3BR cottage or build on the existing foundation there is plenty of potential. Buyer to confirm building restrictions with the county. This property features a new deep well, new well pump, and new septic holding tanks in 2026. The existing interior of the home has been taken down to the framing and includes 100-amp electrical service, providing a solid starting point for your vision. Outdoor enthusiasts will enjoy everything this property has to offer. Fish for perch, bass, catfish, and snakeheads, or spend the day crabbing from your shoreline. Waterfowl hunters will enjoy the existing duck blind, while everyone will appreciate the stunning sunsets overlooking the water. Whether you're looking for a peaceful weekend escape, a hunting and fishing camp, or the site of your future waterfront cottage, this property offers an opportunity that's becoming increasingly difficult to find.

220 Kirbys Landing Rd, Millington

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

$549,900

Professional Photos coming soon. TWO LOTS FOR SALE with two different tax Ids/addresses. The home sits on 1.16 arces and the additional adjacent lot sits on 1.10 acres which was graded as a Par 3 golf course. The second lots tax ID is 1805020174, address is 165 Greenwood Creek Rd, Queenstown, MD 21658. This house is ready for your own personal touches, with four bedrooms and 2.5 baths sitting on 2.16 lush acres of privacy. This homes offers a mature landscaped yard with WATERVIEWS! Hardwood floors throughout just waiting to be brought back to their original beauty. This home also features a full In-law suite / guest house. Located in Queenstown, with easy commutes to Annapolis, Washington, Baltimore, Delaware and the beaches. Come see this home and make it your own today!

Professional Photos coming soon. TWO LOTS FOR SALE with two different tax Ids/addresses. The home sits on 1.16 arces and the additional adjacent lot sits on 1.10 acres which was graded as a Par 3 golf course. The second lots tax ID is 1805020174, address is 165 Greenwood Creek Rd, Queenstown, MD 21658. This house is ready for your own personal touches, with four bedrooms and 2.5 baths sitting on 2.16 lush acres of privacy. This homes offers a mature landscaped yard with WATERVIEWS! Hardwood floors throughout just waiting to be brought back to their original beauty. This home also features a full In-law suite / guest house. Located in Queenstown, with easy commutes to Annapolis, Washington, Baltimore, Delaware and the beaches. Come see this home and make it your own today!

161 Greenwood Creek Rd, Queenstown

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

$825,000

Beautifully sited on a fabulous 1.03-acre lot in sought-after Prospect Bay Golf and Country Club, this spacious home offers the best of both water and golf course living. Enjoy lovely water views and stunning sunsets from several rooms or while relaxing on the wraparound front porch. From the rear of the home, take in peaceful golf course views overlooking the newly renovated par-five 5th hole. Enjoy these views from the heated and cooled Florida room or from your adjoining deck with a remote controlled awning. Inside, gorgeous hardwood floors flow from the entry through the living and dining rooms. The bright kitchen features Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida room, creating an ideal layout for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with tray ceiling, a huge walk-in closet, and a large jetted tub, walk-in shower, and double vanities. The convenient second-level laundry room, two-car garage, storage shed, and oversized parking pad add to the home’s practicality. Recent improvements include two new (2026) Lennox HVAC Hybrid units with smart Thermostats. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026) and there is a tankless Navien hot water heater. Although not a problem in Prospect Bay, you'll never have to worry about losing power as you have a Generac Generator just outside to take care of a power loss! As a Resident of Prospect Bay enjoy exceptional community amenities, including an 18 hole golf course, driving range, a members only restaurant & bar, clubhouse, swimming pool, boat ramp, tennis courts, basketball, pickleball, kayak racks, and a marina. So many activities for all including Book Club, Dine & Cruise, Movie Night for Kids, Garden Club, Line Dancing, etc . This home is just across the street from the boat ramp, marina and open water leading to the Bay! The perfect place to live and play!

Beautifully sited on a fabulous 1.03-acre lot in sought-after Prospect Bay Golf and Country Club, this spacious home offers the best of both water and golf course living. Enjoy lovely water views and stunning sunsets from several rooms or while relaxing on the wraparound front porch. From the rear of the home, take in peaceful golf course views overlooking the newly renovated par-five 5th hole. Enjoy these views from the heated and cooled Florida room or from your adjoining deck with a remote controlled awning. Inside, gorgeous hardwood floors flow from the entry through the living and dining rooms. The bright kitchen features Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida room, creating an ideal layout for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with tray ceiling, a huge walk-in closet, and a large jetted tub, walk-in shower, and double vanities. The convenient second-level laundry room, two-car garage, storage shed, and oversized parking pad add to the home’s practicality. Recent improvements include two new (2026) Lennox HVAC Hybrid units with smart Thermostats. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026) and there is a tankless Navien hot water heater. Although not a problem in Prospect Bay, you'll never have to worry about losing power as you have a Generac Generator just outside to take care of a power loss! As a Resident of Prospect Bay enjoy exceptional community amenities, including an 18 hole golf course, driving range, a members only restaurant & bar, clubhouse, swimming pool, boat ramp, tennis courts, basketball, pickleball, kayak racks, and a marina. So many activities for all including Book Club, Dine & Cruise, Movie Night for Kids, Garden Club, Line Dancing, etc . This home is just across the street from the boat ramp, marina and open water leading to the Bay! The perfect place to live and play!

116 Prospect Bay Dr W, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535

$2,840,000

Rare Find - 2 houses on one waterfront property! Each with unobstructed views of the water! Privacy without isolation. This will change your mind if you think you need 5 acres or more to have wide open spaces and not have neighbors breathing down your neck! Discover a captivating blend of traditional charm in the vintage cape cod - the main 3-bedroom, 2-bathroom residence, recently updated in spring 2026. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors and upgraded countertops that elevate the kitchen, a home perfect for gatherings. The cozy living room, complete with a brick fireplace and mantel, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom and a traditional floor plan that flows seamlessly throughout. The exterior is equally impressive, featuring a private beach and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. Additional highlights include a guest house(2BR, 1.5 BA, KT,screened porch) and a storage building providing versatility for equipment or hobbies. The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or garden. Former waterside pool could be revitalized, subject to county approval.

Rare Find - 2 houses on one waterfront property! Each with unobstructed views of the water! Privacy without isolation. This will change your mind if you think you need 5 acres or more to have wide open spaces and not have neighbors breathing down your neck! Discover a captivating blend of traditional charm in the vintage cape cod - the main 3-bedroom, 2-bathroom residence, recently updated in spring 2026. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors and upgraded countertops that elevate the kitchen, a home perfect for gatherings. The cozy living room, complete with a brick fireplace and mantel, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom and a traditional floor plan that flows seamlessly throughout. The exterior is equally impressive, featuring a private beach and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. Additional highlights include a guest house(2BR, 1.5 BA, KT,screened porch) and a storage building providing versatility for equipment or hobbies. The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or garden. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester

Listing courtesy of Tidewater Properties. Contact:

$1,750,000

Experience some of the most captivating views the Chesapeake Bay has to offer. Perfectly positioned at the first exit off the Bay Bridge, this waterfront property showcases sweeping water views, stunning sunrises, and a front-row seat to the iconic Chesapeake Bay Bridge. The shoreline is ideal for enjoying the Bay lifestyle-launch a kayak, paddleboard, jet ski, or small skiff right from your backyard, spend the day fishing or crabbing, and unwind while watching the backdrop of the Bay Bridge. Like new construction this home was built just three years ago, this remarkable home offers 9 bedrooms plus a den, this includes a private 4-bedroom in-law suite with its own full kitchen/laundry and entry perfect for in-laws, guests or even its own apartment. Public water and public sewer provide added convenience, while the location offers easy access to shopping, dining, and everyday amenities without ever having to navigate Route 50. Whether you're seeking a waterfront family compound, vacation getaway, or year-round residence, this property combines modern living, unmatched convenience, and unforgettable Chesapeake Bay views. Lot next door is included in sale giving home just under 1 acre.

9 Beds ⋅ 4 Baths

Experience some of the most captivating views the Chesapeake Bay has to offer. Perfectly positioned at the first exit off the Bay Bridge, this waterfront property showcases sweeping water views, stunning sunrises, and a front-row seat to the iconic Chesapeake Bay Bridge. The shoreline is ideal for enjoying the Bay lifestyle-launch a kayak, paddleboard, jet ski, or small skiff right from your backyard, spend the day fishing or crabbing, and unwind while watching the backdrop of the Bay Bridge. Like new construction this home was built just three years ago, this remarkable home offers 9 bedrooms plus a den, this includes a private 4-bedroom in-law suite with its own full kitchen/laundry and entry perfect for in-laws, guests or even its own apartment. Public water and public sewer provide added convenience, while the location offers easy access to shopping, dining, and everyday amenities without ever having to navigate Route 50. Whether you're seeking a waterfront family compound, vacation getaway, or year-round residence, this property combines modern living, unmatched convenience, and unforgettable Chesapeake Bay views. Lot next door is included in sale giving home just under 1 acre.

410 Wallman Way, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242

$749,000

Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This move-in-ready residence features 3 bedrooms, 2 full baths, and a versatile bonus room that can serve as a home office, guest room, or potential 4th bedroom. Meticulously updated and lovingly maintained throughout, pride of ownership is evident at every turn. Thoughtful upgrades create a warm and inviting atmosphere, including under-cabinet lighting and dimmer switches throughout the home, allowing you to create the perfect ambiance for any occasion. The kitchen is both stylish and functional, featuring an additional beverage refrigerator, making entertaining family and friends a breeze. The bathrooms offer a touch of luxury with heated floors and built-in Bluetooth speakers, creating a spa-like retreat within your own home. Situated on a large, level waterfront lot, the property is designed for both relaxation and recreation. Across the creek, protected conservation land provides a peaceful, natural backdrop and exceptional privacy rarely found on the water. Raised garden beds offer the opportunity to grow your own herbs and vegetables, while the detached garage, two storage sheds, and attic provide ample space for tools, equipment, seasonal items, and all your waterfront essentials. Spend your evenings gathered around the fire pit overlooking the water, launch a kayak from your backyard, or cruise to one of the many waterfront restaurants accessible from the Eastern Bay. Whether you're entertaining guests or enjoying a quiet sunset, this property embraces the laid-back charm of coastal living. Conveniently located just 10 minutes from the Bay Bridge, 20 minutes from Annapolis, and approximately 90 minutes from the beach, you'll enjoy easy access to everything while feeling worlds away. A rare opportunity to own a turnkey waterfront retreat in one of Kent Island's most desirable locations, where every detail has been thoughtfully curated for comfort, convenience, and enjoyment.

Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This move-in-ready residence features 3 bedrooms, 2 full baths, and a versatile bonus room that can serve as a home office, guest room, or potential 4th bedroom. Meticulously updated and lovingly maintained throughout, pride of ownership is evident at every turn. Thoughtful upgrades create a warm and inviting atmosphere, including under-cabinet lighting and dimmer switches throughout the home, allowing you to create the perfect ambiance for any occasion. The kitchen is both stylish and functional, featuring an additional beverage refrigerator, making entertaining family and friends a breeze. The bathrooms offer a touch of luxury with heated floors and built-in Bluetooth speakers, creating a spa-like retreat within your own home. Situated on a large, level waterfront lot, the property is designed for both relaxation and recreation. Across the creek, protected conservation land provides a peaceful, natural backdrop and exceptional privacy rarely found on the water. Raised garden beds offer the opportunity to grow your own herbs and vegetables, while the detached garage, two storage sheds, and attic provide ample space for tools, equipment, seasonal items, and all your waterfront essentials. Spend your evenings gathered around the fire pit overlooking the water, launch a kayak from your backyard, or cruise to one of the many waterfront restaurants accessible from the Eastern Bay. Whether you're entertaining guests or enjoying a quiet sunset, this property embraces the laid-back charm of coastal living. Conveniently located just 10 minutes from the Bay Bridge, 20 minutes from Annapolis, and approximately 90 minutes from the beach, you'll enjoy easy access to everything while feeling worlds away. A rare opportunity to own a turnkey waterfront retreat in one of Kent Island's most desirable locations, where every detail has been thoughtfully curated for comfort, convenience, and enjoyment.

205 Riverside Dr, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

$1,350,000

WATERFRONT LIVING on Winchester Creek! This wonderful 4 bedroom, 2.5 bath Grasonville estate offers the ultimate Eastern Shore lifestyle, fully refreshed with a newly painted neutral interior, gleaming refinished hardwoods, and carpet. A grand 2-story foyer with a palladium window, transom accents, and elegant French doors welcomes you inside. The main level features 11' ceilings, a great room with fireplace and a bank of windows with water views, a separate dining room, bright breakfast room, and a fabulous kitchen with an island, pantry, and reverse osmosis water filtration. The main floor primary suite boasts a walk-in closet and a no-threshold shower, complemented by a full, hall bath and convenient half bath. Upstairs, a versatile bonus space features custom built-ins— perfect for an office and media space. Your outdoor resort awaits: a Trex deck with built-in benches and retractable awning leads to a custom paver patio and a sparkling 18’ x 37’ saltwater pool with a tranquil waterfall feature. Boaters will love the deeded boat slip (#10), mooring pile, and private boat lift. Rounding out this incredible home is an oversized 2-car garage with storage space, HVAC (2018), buried 500-gallon propane tank, and full water conditioning system and lush landscaping.

WATERFRONT LIVING on Winchester Creek! This wonderful 4 bedroom, 2.5 bath Grasonville estate offers the ultimate Eastern Shore lifestyle, fully refreshed with a newly painted neutral interior, gleaming refinished hardwoods, and carpet. A grand 2-story foyer with a palladium window, transom accents, and elegant French doors welcomes you inside. The main level features 11' ceilings, a great room with fireplace and a bank of windows with water views, a separate dining room, bright breakfast room, and a fabulous kitchen with an island, pantry, and reverse osmosis water filtration. The main floor primary suite boasts a walk-in closet and a no-threshold shower, complemented by a full, hall bath and convenient half bath. Upstairs, a versatile bonus space features custom built-ins— perfect for an office and media space. Your outdoor resort awaits: a Trex deck with built-in benches and retractable awning leads to a custom paver patio and a sparkling 18’ x 37’ saltwater pool with a tranquil waterfall feature. Boaters will love the deeded boat slip (#10), mooring pile, and private boat lift. Rounding out this incredible home is an oversized 2-car garage with storage space, HVAC (2018), buried 500-gallon propane tank, and full water conditioning system and lush landscaping.

104 Port Ct, Grasonville

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

$7,995,000

Set on 20 private waterfront acres with over 800 feet of shoreline along the Chesapeake Bay, this extraordinary estate offers a rare opportunity to own one of Maryland’s most impressive legacy properties. Behind a gated entrance and winding tree-lined drive, the residence combines timeless architecture, exceptional craftsmanship, and resort-inspired amenities designed for both grand entertaining and everyday enjoyment. The shoreline is simply remarkable, featuring riprap protection, a private pier with lifts, sandy beach areas, water and electric service, and panoramic Bay views that deliver spectacular sunsets year-round. Whether enjoying a quiet morning by the water, setting out for a day on the Bay, or gathering with family and friends for an evening by the fire, every aspect of the property has been thoughtfully designed to embrace the waterfront lifestyle. Inside, over 15,000 square feet of finished living space showcases Brazilian cherry flooring, handcrafted millwork, coffered ceilings, custom paneling, seven fireplaces, and beautifully curated living spaces throughout. The gourmet kitchen serves as the heart of the home, featuring premium appliances, an oversized island, sunlit breakfast room, and a fully equipped butler’s pantry designed for seamless entertaining. The residence offers two luxurious primary suites, including a main-level retreat with fireplace, spa-inspired bath, private office, and direct access to the waterfront. Multiple ensuite guest bedrooms, a theater room, game room, exercise suite, expansive third-floor recreation space, and a private apartment above the garage provide exceptional flexibility for hosting family and guests. Outdoor amenities rival those of a private resort. Enjoy a saltwater pool and spa, covered poolside entertaining pavilion with outdoor kitchen and fireplace, regulation tennis and pickleball court, expansive patios and terraces, fire pit, pond with fountain, playground, and extensive professional landscaping that creates a setting of complete privacy and tranquility. This is more than a home—it is a Chesapeake Bay estate designed for generations to gather, celebrate, and create lasting memories. A rare offering where luxury, privacy, recreation, and waterfront living come together on an extraordinary scale.

8 Beds ⋅ 10 Baths

Set on 20 private waterfront acres with over 800 feet of shoreline along the Chesapeake Bay, this extraordinary estate offers a rare opportunity to own one of Maryland’s most impressive legacy properties. Behind a gated entrance and winding tree-lined drive, the residence combines timeless architecture, exceptional craftsmanship, and resort-inspired amenities designed for both grand entertaining and everyday enjoyment. The shoreline is simply remarkable, featuring riprap protection, a private pier with lifts, sandy beach areas, water and electric service, and panoramic Bay views that deliver spectacular sunsets year-round. Whether enjoying a quiet morning by the water, setting out for a day on the Bay, or gathering with family and friends for an evening by the fire, every aspect of the property has been thoughtfully designed to embrace the waterfront lifestyle. Inside, over 15,000 square feet of finished living space showcases Brazilian cherry flooring, handcrafted millwork, coffered ceilings, custom paneling, seven fireplaces, and beautifully curated living spaces throughout. The gourmet kitchen serves as the heart of the home, featuring premium appliances, an oversized island, sunlit breakfast room, and a fully equipped butler’s pantry designed for seamless entertaining. The residence offers two luxurious primary suites, including a main-level retreat with fireplace, spa-inspired bath, private office, and direct access to the waterfront. Multiple ensuite guest bedrooms, a theater room, game room, exercise suite, expansive third-floor recreation space, and a private apartment above the garage provide exceptional flexibility for hosting family and guests. Outdoor amenities rival those of a private resort. Enjoy a saltwater pool and spa, covered poolside entertaining pavilion with outdoor kitchen and fireplace, regulation tennis and pickleball court, expansive patios and terraces, fire pit, pond with fountain, playground, and extensive professional landscaping that creates a setting of complete privacy and tranquility. This is more than a home—it is a Chesapeake Bay estate designed for generations to gather, celebrate, and create lasting memories. A rare offering where luxury, privacy, recreation, and waterfront living come together on an extraordinary scale.

7328 Kent Point Rd, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$649,000

Welcome to your dream coastal retreat in the highly sought-after Chester River Beach community of Grasonville, Maryland. This beautiful, luxurious bayside property is a single-story rancher that offers the perfect blend of modern upgrades, breathtaking views of the Bay and relaxed coastal living in a vibrant and lively neighborhood that is perfect for boating enthusiasts, crabbing, and fishing. This fully remodeled three bedroom, one full bath home sits on one of the largest corner lots and has been thoughtfully updated from top to bottom with high end finishes and brand new systems throughout. Enjoy peace of mind with newly installed roof, vinyl siding, flooring, central air conditioning system with heat pump, new well tank, and water heater. Next on the list is a completely renovated bathroom featuring a state of the art smart bidet toilet with heated seat, and automated micro bubble cleansing technology bringing spa like comfort to your everyday routine. After enjoying the beach, boating, fishing or swimming, relax in the spacious brand new shower. Gorgeous coastal style kitchen designed with two spacious islands, providing ample prep space, including breakfast bar seating perfect for entertaining family and guests. Amenties showcasing high end cabinetry, ceramic tile backsplash, wall mounted retractable pot filler, smart appliances including flat top range, stainless double door refrigerator, double oven, and farm sink sink as well as other highend features! The home also includes convenient laundry with a new washer and dryer, offering everyday ease and functionality. Enjoy breathtaking water views filling the space with natural light and creating a serene coastal atmosphere through two newly installed bay windows. Additional features include a cozy working fireplace, sliding patio door leading to a newly constructed deck with additional views of the bay, off-street parking, and a spacious detached garage equipped with electrical service. The home also includes a full, easily accessible attic, providing plenty of storage and potential to include additional living space! The property includes access to private boat docks, boat ramps, and private managed beach just a few steps away. Residents also enjoy a community park, entertainment pavilion with stunning waterfront views, along with convenient access to nearby shopping malls, restaurants, and grocery stores. Boat directly to many waterfront bars and boating restaurants making every day feel like a vacation. Whether you're looking for a full-time residence or a weekend getaway, this move-in-ready Chester River Beach home delivers the very best of Eastern Shore bay-front living.

3 Beds ⋅ 1 Baths

Welcome to your dream coastal retreat in the highly sought-after Chester River Beach community of Grasonville, Maryland. This beautiful, luxurious bayside property is a single-story rancher that offers the perfect blend of modern upgrades, breathtaking views of the Bay and relaxed coastal living in a vibrant and lively neighborhood that is perfect for boating enthusiasts, crabbing, and fishing. This fully remodeled three bedroom, one full bath home sits on one of the largest corner lots and has been thoughtfully updated from top to bottom with high end finishes and brand new systems throughout. Enjoy peace of mind with newly installed roof, vinyl siding, flooring, central air conditioning system with heat pump, new well tank, and water heater. Next on the list is a completely renovated bathroom featuring a state of the art smart bidet toilet with heated seat, and automated micro bubble cleansing technology bringing spa like comfort to your everyday routine. After enjoying the beach, boating, fishing or swimming, relax in the spacious brand new shower. Gorgeous coastal style kitchen designed with two spacious islands, providing ample prep space, including breakfast bar seating perfect for entertaining family and guests. Amenties showcasing high end cabinetry, ceramic tile backsplash, wall mounted retractable pot filler, smart appliances including flat top range, stainless double door refrigerator, double oven, and farm sink sink as well as other highend features! The home also includes convenient laundry with a new washer and dryer, offering everyday ease and functionality. Enjoy breathtaking water views filling the space with natural light and creating a serene coastal atmosphere through two newly installed bay windows. Additional features include a cozy working fireplace, sliding patio door leading to a newly constructed deck with additional views of the bay, off-street parking, and a spacious detached garage equipped with electrical service. The home also includes a full, easily accessible attic, providing plenty of storage and potential to include additional living space! The property includes access to private boat docks, boat ramps, and private managed beach just a few steps away. Residents also enjoy a community park, entertainment pavilion with stunning waterfront views, along with convenient access to nearby shopping malls, restaurants, and grocery stores. Boat directly to many waterfront bars and boating restaurants making every day feel like a vacation. Whether you're looking for a full-time residence or a weekend getaway, this move-in-ready Chester River Beach home delivers the very best of Eastern Shore bay-front living.

801 Chester River Dr, Grasonville

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663

$599,000

Enjoy carefree WATERFRONT living in this Beautifully UPDATED Condo in the sought-after Oyster Cove Community! Offering 3 bedrooms and 2 full bathrooms, this light-filled, one-level residence features an open floor plan designed for easy living and entertaining! Stunning wide plank wood flooring flows throughout the main living areas, complemented by newer stone countertops, fresh interior custom paint throughout and NEW carpet in the bedrooms. The spacious living and dining areas open to a Waterfront Deck where you can relax and enjoy breathtaking Sunsets over Eastern Bay and The Narrows. The thoughtfully designed layout offers generous bedroom sizes and two updated baths. Recent exterior improvements include new siding and new windows. Oyster Cove residents enjoy an exceptional Waterfront lifestyle with access to two Marinas, Swimming Pool, two Tennis Courts, a walking/jogging path and a Clubhouse with a fitness room. Conveniently located within walking distance to many restaurants, coffee spots, ice cream parlors, shops and popular dock bars!! Hop on the Kent Island Cross Trail for a bike ride throughout the Island! Just minutes from the Chesapeake Bay Bridge, this is Eastern Shore living at its finest!

Enjoy carefree WATERFRONT living in this Beautifully UPDATED Condo in the sought-after Oyster Cove Community! Offering 3 bedrooms and 2 full bathrooms, this light-filled, one-level residence features an open floor plan designed for easy living and entertaining! Stunning wide plank wood flooring flows throughout the main living areas, complemented by newer stone countertops, fresh interior custom paint throughout and NEW carpet in the bedrooms. The spacious living and dining areas open to a Waterfront Deck where you can relax and enjoy breathtaking Sunsets over Eastern Bay and The Narrows. The thoughtfully designed layout offers generous bedroom sizes and two updated baths. Recent exterior improvements include new siding and new windows. Oyster Cove residents enjoy an exceptional Waterfront lifestyle with access to two Marinas, Swimming Pool, two Tennis Courts, a walking/jogging path and a Clubhouse with a fitness room. Conveniently located within walking distance to many restaurants, coffee spots, ice cream parlors, shops and popular dock bars!! Hop on the Kent Island Cross Trail for a bike ride throughout the Island! Just minutes from the Chesapeake Bay Bridge, this is Eastern Shore living at its finest!

116 Oyster Cove Dr Unit #1D, Grasonville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$362,500

Welcome to 1302 Marion Quimby Dr. Nestled in the serene Thompson Creek community, this charming townhouse with a new HVAC and hot water heater offers a perfect blend of comfort and modern living. With 1,161 square feet of thoughtfully designed space, this home features two spacious bedrooms and two and a half bathrooms, making it an ideal retreat for those seeking tranquility and convenience. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The contemporary design is enhanced by plush brand new carpeting and elegant ceramic tile flooring, creating a warm and welcoming atmosphere. The living room is anchored by a cozy fireplace, complete with glass doors and a stylish mantel, perfect for those chilly evenings spent at home. The kitchen is a culinary delight, featuring ample table space for casual dining and modern appliances, including a dishwasher, microwave, and electric oven/range. Whether you're preparing a gourmet meal or enjoying a quick breakfast, this kitchen is designed to meet your needs. Retreat to the primary suite, which boasts an en-suite bathroom for added privacy and convenience. Thoughtful window treatments throughout the home allow for natural light while maintaining a sense of intimacy. Step outside to enjoy the beautiful exterior features, including a charming balcony and deck over-looking Thompson Creek and gorgeous water views and sunsets, perfect for sipping your morning coffee or unwinding after a long day. The community amenities are a true highlight, offering access to a refreshing outdoor pool, tennis courts, and scenic jog/walk paths that wind through beautifully landscaped grounds. The property is situated on the banks of Thompson Creek, providing stunning views of the water, lush pastures, and surrounding trees. Imagine relaxing on your deck while listening to the gentle sounds of the creek, creating a peaceful oasis right at your doorstep. With unassigned off-street parking and a well-maintained community that includes exterior building maintenance, management, and trash services, this home offers both convenience and peace of mind. Experience the perfect blend of comfort, community, and natural beauty in this delightful townhouse. Whether you're looking for a weekend getaway or a permanent residence, this property is sure to meet your needs and exceed your expectations.

Welcome to 1302 Marion Quimby Dr. Nestled in the serene Thompson Creek community, this charming townhouse with a new HVAC and hot water heater offers a perfect blend of comfort and modern living. With 1,161 square feet of thoughtfully designed space, this home features two spacious bedrooms and two and a half bathrooms, making it an ideal retreat for those seeking tranquility and convenience. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The contemporary design is enhanced by plush brand new carpeting and elegant ceramic tile flooring, creating a warm and welcoming atmosphere. The living room is anchored by a cozy fireplace, complete with glass doors and a stylish mantel, perfect for those chilly evenings spent at home. The kitchen is a culinary delight, featuring ample table space for casual dining and modern appliances, including a dishwasher, microwave, and electric oven/range. Whether you're preparing a gourmet meal or enjoying a quick breakfast, this kitchen is designed to meet your needs. Retreat to the primary suite, which boasts an en-suite bathroom for added privacy and convenience. Thoughtful window treatments throughout the home allow for natural light while maintaining a sense of intimacy. Step outside to enjoy the beautiful exterior features, including a charming balcony and deck over-looking Thompson Creek and gorgeous water views and sunsets, perfect for sipping your morning coffee or unwinding after a long day. The community amenities are a true highlight, offering access to a refreshing outdoor pool, tennis courts, and scenic jog/walk paths that wind through beautifully landscaped grounds. The property is situated on the banks of Thompson Creek, providing stunning views of the water, lush pastures, and surrounding trees. Imagine relaxing on your deck while listening to the gentle sounds of the creek, creating a peaceful oasis right at your doorstep. With unassigned off-street parking and a well-maintained community that includes exterior building maintenance, management, and trash services, this home offers both convenience and peace of mind. Experience the perfect blend of comfort, community, and natural beauty in this delightful townhouse. Whether you're looking for a weekend getaway or a permanent residence, this property is sure to meet your needs and exceed your expectations.

1302 Marion Quimby Dr, Stevensville

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

$4,995,000

Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

5 Beds ⋅ 5 Baths

Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$344,900

Motivated seller! Experience relaxed waterfront living in this beautifully updated townhome condominium overlooking scenic Thompson Creek, where stunning water views, community amenities, and an exceptional coastal lifestyle come together. Thoughtfully renovated and move-in ready, this waterfront retreat blends modern upgrades with inviting indoor and outdoor spaces designed for both everyday comfort and, entertaining.The main level welcomes you with an updated kitchen featuring granite countertops, stainless steel appliances, and abundant cabinetry. Just beyond, the sunken living room creates a warm and inviting atmosphere highlighted by a beautiful brick gas fireplace (ready for propane hookup if desired and easily convertible back to wood-burning), a custom wet bar, and seamless access to the spacious waterfront deck, perfect for enjoying peaceful sunsets over the creek. Recent improvements totaling approximately $20,000 include luxury vinyl plank flooring, new carpet upstairs, fresh interior paint throughout, and new blinds, giving the home a refreshed, modern feel. Upstairs, you'll find two generously sized bedrooms, ample closet space, and 2.5 baths, including a spacious primary suite with a well-appointed ensuite bath. A private balcony off the primary bedroom provides tranquil water views, breathtaking sunsets, and peaceful views of the community walking paths. Outdoor living is truly at the heart of this property. Enjoy boating, fishing, kayaking, swimming, and waterfront recreation just moments from your door. Residents have access to a community pool, clubhouse, tennis courts, scenic walking and jogging paths, nearby marinas, and multiple boat launch options, including Thompson Creek Landing within walking distance and convenient access to Kent Island. Situated along the banks of Thompson Creek, this home offers picturesque views of the water, mature trees, and surrounding natural beauty, creating a peaceful setting perfect for relaxing, entertaining, or simply enjoying the waterfront lifestyle. Additional conveniences include unassigned off-street parking and a well-maintained community offering exterior building maintenance, professional management, and trash service, providing low-maintenance living and added peace of mind. Whether you're searching for a full-time residence, weekend retreat, or investment opportunity, this home offers the perfect blend of comfort, recreation, and coastal charm in an unbeatable waterfront setting.

Motivated seller! Experience relaxed waterfront living in this beautifully updated townhome condominium overlooking scenic Thompson Creek, where stunning water views, community amenities, and an exceptional coastal lifestyle come together. Thoughtfully renovated and move-in ready, this waterfront retreat blends modern upgrades with inviting indoor and outdoor spaces designed for both everyday comfort and, entertaining.The main level welcomes you with an updated kitchen featuring granite countertops, stainless steel appliances, and abundant cabinetry. Just beyond, the sunken living room creates a warm and inviting atmosphere highlighted by a beautiful brick gas fireplace (ready for propane hookup if desired and easily convertible back to wood-burning), a custom wet bar, and seamless access to the spacious waterfront deck, perfect for enjoying peaceful sunsets over the creek. Recent improvements totaling approximately $20,000 include luxury vinyl plank flooring, new carpet upstairs, fresh interior paint throughout, and new blinds, giving the home a refreshed, modern feel. Upstairs, you'll find two generously sized bedrooms, ample closet space, and 2.5 baths, including a spacious primary suite with a well-appointed ensuite bath. A private balcony off the primary bedroom provides tranquil water views, breathtaking sunsets, and peaceful views of the community walking paths. Outdoor living is truly at the heart of this property. Enjoy boating, fishing, kayaking, swimming, and waterfront recreation just moments from your door. Residents have access to a community pool, clubhouse, tennis courts, scenic walking and jogging paths, nearby marinas, and multiple boat launch options, including Thompson Creek Landing within walking distance and convenient access to Kent Island. Situated along the banks of Thompson Creek, this home offers picturesque views of the water, mature trees, and surrounding natural beauty, creating a peaceful setting perfect for relaxing, entertaining, or simply enjoying the waterfront lifestyle. Additional conveniences include unassigned off-street parking and a well-maintained community offering exterior building maintenance, professional management, and trash service, providing low-maintenance living and added peace of mind. Whether you're searching for a full-time residence, weekend retreat, or investment opportunity, this home offers the perfect blend of comfort, recreation, and coastal charm in an unbeatable waterfront setting.

1102 Marion Quimby Dr, Stevensville

Listing courtesy of Redfin Corp. Contact: 3016586186

$799,000

This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoor living in general is a highlight here with each floor allowing for a different perspective of the Eastern Shore landscape. Don't forget about the amenities of the community. Lounge out by the pool, walk to famous waterfront seafood establishments, or navigate the vast waters of the Chesapeake from your deeded 35 foot deep water boat slip just steps away. This luxury Eastern Shore destination is located just an hour from Washington, D.C. or Baltimore and less than two hours from Philadelphia.

4 Beds ⋅ 4 Baths

This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoor living in general is a highlight here with each floor allowing for a different perspective of the Eastern Shore landscape. Don't forget about the amenities of the community. Lounge out by the pool, walk to famous waterfront seafood establishments, or navigate the vast waters of the Chesapeake from your deeded 35 foot deep water boat slip just steps away. This luxury Eastern Shore destination is located just an hour from Washington, D.C. or Baltimore and less than two hours from Philadelphia.

110 Channel Marker Way Unit #203, Grasonville

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

$1,470,000

Waterfront living with lifestyle, location and luxury! Located at the mouth of the Chester River, this home is in the perfect spot for days on the Bay, boat rides to Kent Narrows restaurants, golf at Queenstown and shopping the Outlets. Just minutes from the Bay Bridge, this beautifully updated home delivers the best of Eastern Shore living with 259' waterfront, community pier, good schools and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water a breeze, while the waterfront backyard soaks up the sun and wildlife on Winchester Creek. This beautiful home features more than 4,400 square feet on three finished levels with west-facing water views from expansive windows that fill the home with natural light. The two-story family room features a rebuilt luxury fireplace with custom trim work, creating an everyday space that is upscale yet comfortable. The renovated gourmet kitchen offers quartz countertops, heated floors, stainless steel appliances, abundant cabinetry, a breakfast nook, and a redesigned island perfect for gathering with family and friends. The first floor also boasts a two-story foyer, formal dining room, and a comfortable living room/study complete with large windows and a 2nd fireplace. Hardwood floors, custom millwork, fresh paint and designer finishes create a timeless coastal feel thoughout. Enjoy beautiful water views from the main-level primary suite that features California Closets, a beautifully remodeled spa-inspired bath and a cozy bay window sitting area. The second waterfront ensuite provides ideal accommodations for guests, extended family or single-floor living. The second level features three additional bedrooms and a versatile bonus room ideal for a home office, homework or as a second family room. The third level is designed for entertaining, complete with a wet bar, beverage cooler, full bath and surround sound. It's perfect for game days, movie nights, or extended-stay guests. Set on more than 1.37 acres, the property offers privacy, an expansive lawn, updated landscaping, abundant wildlife and sweeping water views. Enjoy morning coffee as the sun rises over the water and glowing sunsets from the new TimberTech deck and covered porch. The slip at Homeport's 4MLW private pier is almost next-door for an early morning ride or sunset cruise. Whether hosting family and friends, raising children, enjoying pets in the backyard or unwinding by the water after a day on the boat, this setting is thoughtfully designed for comfort and ease. Extensive recent improvements in the dedicated utility room include dual Bosch high-efficiency HVAC systems (2023 and 2024), a Rinnai tankless water heater and a whole-house smart water treatment and management system. The home also features smart thermostats on each floor, ceiling fans throughout, a Vector security system, invisible pet fence, professional landscaping, nearly all new lighting inside & out, updated bathrooms and more. Enjoy Chesapeake living with easy access to Annapolis and the Bay Bridge.

5 Beds ⋅ 5 Baths

Waterfront living with lifestyle, location and luxury! Located at the mouth of the Chester River, this home is in the perfect spot for days on the Bay, boat rides to Kent Narrows restaurants, golf at Queenstown and shopping the Outlets. Just minutes from the Bay Bridge, this beautifully updated home delivers the best of Eastern Shore living with 259' waterfront, community pier, good schools and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water a breeze, while the waterfront backyard soaks up the sun and wildlife on Winchester Creek. This beautiful home features more than 4,400 square feet on three finished levels with west-facing water views from expansive windows that fill the home with natural light. The two-story family room features a rebuilt luxury fireplace with custom trim work, creating an everyday space that is upscale yet comfortable. The renovated gourmet kitchen offers quartz countertops, heated floors, stainless steel appliances, abundant cabinetry, a breakfast nook, and a redesigned island perfect for gathering with family and friends. The first floor also boasts a two-story foyer, formal dining room, and a comfortable living room/study complete with large windows and a 2nd fireplace. Hardwood floors, custom millwork, fresh paint and designer finishes create a timeless coastal feel thoughout. Enjoy beautiful water views from the main-level primary suite that features California Closets, a beautifully remodeled spa-inspired bath and a cozy bay window sitting area. The second waterfront ensuite provides ideal accommodations for guests, extended family or single-floor living. The second level features three additional bedrooms and a versatile bonus room ideal for a home office, homework or as a second family room. The third level is designed for entertaining, complete with a wet bar, beverage cooler, full bath and surround sound. It's perfect for game days, movie nights, or extended-stay guests. Set on more than 1.37 acres, the property offers privacy, an expansive lawn, updated landscaping, abundant wildlife and sweeping water views. Enjoy morning coffee as the sun rises over the water and glowing sunsets from the new TimberTech deck and covered porch. The slip at Homeport's 4MLW private pier is almost next-door for an early morning ride or sunset cruise. Whether hosting family and friends, raising children, enjoying pets in the backyard or unwinding by the water after a day on the boat, this setting is thoughtfully designed for comfort and ease. Extensive recent improvements in the dedicated utility room include dual Bosch high-efficiency HVAC systems (2023 and 2024), a Rinnai tankless water heater and a whole-house smart water treatment and management system. The home also features smart thermostats on each floor, ceiling fans throughout, a Vector security system, invisible pet fence, professional landscaping, nearly all new lighting inside & out, updated bathrooms and more. Enjoy Chesapeake living with easy access to Annapolis and the Bay Bridge.

109 Starboard Ct, Grasonville

Listing courtesy of Northrop Realty. Contact: 4105310321

$875,000

Much loved home sited on 1.03 acres offering sunset views over the water on one side and golf course views on the other. This spacious home features quality 2x6 construction, hardwood flooring, and Andersen windows that provide abundant natural light throughout. The kitchen measures approximately 19’ x 14’ and includes maple cabinetry, a center island, table space, and an open layout connecting directly to the family room. The family room features a fireplace with an efficient wood-burning insert and a wall mounted 77 inch LG OLED TV, about one year old. Separate living and dining rooms, both with bow windows, frame the beautiful water views. The main-level fourth bedroom includes built-in shelving and currently serves as a home office. The gracious primary suite features water views from a bow window, a large bath, and huge walk-in closet. Two additional good sized bedrooms and a full bath complete the upper level. The oversized two-car garage offers approximately 600 square feet with workshop space, pegboard walls, and extensive shelving. The blacktop driveway includes a large parking pad with room for up to six vehicles. Outdoor features include a screened porch overlooking the golf course and a 16’ x 12’ Amish-built shed designed to complement the home, complete with interior shelving. Additional features include a walk-in attic with shelving and extensive storage space, recently upgraded lighting, a built-in ironing board in the laundry area, and a Bruno stairlift on the wide staircase between the first and second floors, which can be removed if desired. Recent upgrades include new washer, dryer, refrigerator, microwave, dishwasher, and Trane heat pumps that are less than two years old. Located in the waterfront community of Prospect Bay, offering resort-style amenities—including golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant.