Refine Search
Map
Sort by
$825,000
4 Beds ⋅ 3 Baths
Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined architectural details throughout, a main-level home office, and a spacious family room anchored by a cozy gas fireplace. The gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich mahogany cabinetry, stainless steel appliances, double wall ovens, a center island, pantry, and a sunny breakfast area. Upstairs, the spacious primary suite offers a walk-in closet and a luxurious en-suite bath with a soaking tub and separate shower, while three additional bedrooms provide plenty of room for family and guests. Above the garage, an expansive bonus room offers endless possibilities for recreation, work, fitness, or guest accommodations, making it one of the home's most versatile spaces. Relax on the welcoming front porch where you can enjoy the neighborhood's charming streetscape and peaceful surroundings, or unwind in the screened porch overlooking the fenced backyard, an inviting space for morning coffee, outdoor dining, or relaxing. A rear-entry two-car garage adds everyday convenience while preserving the home's classic curb appeal. Located in one of Kent Island's premier waterfront neighborhoods, Gibson's Grant offers exceptional resort-style amenities, including a community pool, clubhouse, fitness center, walking trails, kayak launch, fishing pier, pavilion, playgrounds, picnic areas, and water access to Macum Creek and the Chester River. Just minutes from Route 50 and the Chesapeake Bay Bridge, this home provides an easy commute to Annapolis, Baltimore, Washington, D.C., and Maryland's Eastern Shore while offering the relaxed coastal lifestyle that makes Kent Island so desirable.

313 Thomas White Blvd, Chester

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 906-3848
$285,000
3 Beds ⋅ 2 Baths
Enjoy comfort, convenience, and scenic surroundings in this lovely3‑bedroom, 2‑bath condo located in the desirable Thompson Creek community. This inviting home features a cozy living room fireplace and a peaceful pond view, creating a warm and relaxing atmosphere year‑round. Residents benefit from outstanding community amenities, including a walking trail, outdoor pool, and fitness center. Perfectly situated for easy access to the Bay Bridge, local shopping, dining, and commuter routes, this location offers both practicality and lifestyle appeal. A wonderful opportunity to enjoy low‑maintenance Eastern Shore living in a beautifully maintained community.

1403 Marion Quimby Dr, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483
$856,000
3 Beds ⋅ 3 Baths
Welcome to Your Dream Home at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Lille Loft model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors. A chef's dream, the Gourmet Kitchen is the heart of the home, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining, and a separate beverage center! Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers a spacious loft, a flexible area perfect for a second family room, hobby space, and an additional bedroom and bathroom for overnight guests. Also, the large above attic storage room is fully finished. More storage is available in the oversized fully finished two car garage with extra room for a golf cart. Off the dining area is a screened-in porch and patio, and the community run irrigation system to keep your lawn lush and green! You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis (17 miles), DC (45 miles), Baltimore (45 miles), and BWI (30 miles). Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by endless views of the Chester River.

193 Spinnaker Way, Chester

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

$615,000
4 Beds ⋅ 5 Baths
Welcome to this like-new, impeccably maintained stone front end-unit townhome offering four finished levels of thoughtfully designed living space, 4/5 bedrooms, 4.5 bathrooms, and numerous custom upgrades throughout. Perfectly located just one mile from the Chesapeake Bay Bridge, this stunning home combines modern luxury with the convenience of Eastern Shore living. You are welcomed to the home by a partial wrap around porch, ideal for decorating and offers coverage for deliveries. Inside you will discover a beautifully updated interior with all four levels of stairs completely renovated with new flooring (2026), representing a $10,000 investment, luxury vinyl plank flooring, new carpet in bedrooms (2025), fresh designer paint, custom blinds, and timeless finishes that make this home truly move-in ready. The heart of the home is the gourmet kitchen, complete with Quartz countertops, stainless steel appliances, gas range, custom lighting, a large center island with breakfast bar, and a custom-built coffee bar featuring its own beverage refrigerator. Just off the kitchen, enjoy a separate dining area and access to the private balcony; perfect for morning coffee or evening relaxation. The inviting living room is warm and welcoming with a custom shiplap accent wall and an electric fireplace, creating the perfect space for entertaining or cozy nights at home. The spacious Primary suite offers a walk-in closet and a beautiful bath featuring a custom tiled shower, tile flooring, and a double vanity. Two additional bedrooms, another full bath, and a thoughtfully designed laundry room complete the bedroom level. The laundry area includes a newer washer and dryer, linen closet, and a dedicated folding and sorting station for added convenience. The impressive fourth floor offers incredible flexibility with a bonus room ideal as a guest bedroom, home office, or playroom. This level also includes a full bathroom, two storage closets with 15x20 attic access for additional storage, and a large private balcony. The finished lower level provides even more living space with a family room, recreation room, or optional fourth bedroom, complete with its own full bathroom. The attached two-car garage is fully finished with heating and air conditioning unit, interior water spigot, and plenty of storage. Additional upgrades include: *Approximately $10,000 in new stair flooring (2026) * New luxury vinyl plank flooring and carpet throughout (2025) * New stainless steel appliances * Electric fireplace * Dual-zone HVAC * Gas heat * Gas Hot water heater * Full-house sprinkler system * Freshly painted interior * Beautiful custom finishes throughout. Beyond the home, you'll enjoy resort-style community amenities including a clubhouse, swimming pool, playground, scenic walking trails, RV and boat storage, a community fishing pier, and kayak launch; perfect for embracing the Chesapeake Bay lifestyle. Experience everything that makes Kent Island one of Maryland's most desirable waterfront communities. Spend weekends boating, fishing, crabbing, kayaking, or paddleboarding on the Chesapeake Bay. Explore miles of scenic walking and biking trails, relax at nearby beaches, visit local wineries, browse the charming shops of Historic Stevensville, or enjoy fresh seafood and waterfront dining along Kent Narrows. Whether you're watching breathtaking sunsets over the Bay, launching your kayak from the community pier, or heading to one of the area's many marinas, Kent Island offers the perfect balance of recreation, natural beauty, and small-town charm; all while remaining an easy commute to Annapolis, Baltimore, Washington, D.C., and the rest of Maryland's Eastern Shore. This exceptional home offers the perfect combination of luxury, location, and low-maintenance living. Simply unpack and enjoy! Dog friendly home. Buyer to verify all HOA fees, documents, and community information through the resale package.

222 Jessica Lyn Ave Unit #G5, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$609,990
2 Beds ⋅ 3 Baths
Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2912, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$309,900
2 Beds ⋅ 2 Baths
Welcome to coastal living in this beautifully updated first-floor, end-unit condo, offering the perfect blend of comfort, convenience, and resort-style amenities in one of Kent Island's most sought-after communities. With no stairs to navigate and handicap-accessible features, this home provides effortless everyday living while enjoying the added privacy and abundant natural light that only an end unit can offer. The beautifully updated kitchen features new quartz countertops, backsplash, a breakfast bar, newer stainless steel appliances, and abundant cabinetry, making it as functional as it is stylish. The adjoining dining area flows seamlessly to the private deck through sliding glass doors, bringing the outdoors in and making entertaining a breeze. Fresh paint, carpet, kitchen appliances, HVAC and washer/dryer are all less than 4 years old. The spacious primary suite serves as a relaxing retreat with a large walk-in closet and private ensuite bath. A second generously sized bedroom offers exceptional flexibility for guests, a home office, or family visits, while elegant plantation shutters add timeless charm and character to both bedrooms. Life at Bayside is about much more than the home itself. Residents enjoy a truly maintenance-free lifestyle, with exterior maintenance and community upkeep handled by the condominium association, leaving more time to enjoy everything Kent Island has to offer. Community amenities include a clubhouse, swimming pool, fitness center, tennis courts, beautifully landscaped grounds, and Castle Marina just a short walk away. Outdoor enthusiasts will appreciate being only steps from the Cross Island Trail, offering miles of scenic walking and biking paths showcasing the natural beauty of the Chesapeake Bay. Ideally located near waterfront dining, shopping, and local attractions, this home also provides easy access to Route 50 and the Chesapeake Bay Bridge, international airports and coastal beaches, making commuting and travel exceptionally convenient. Where every day feels like a vacation—and the only thing left to maintain is your schedule.

302 Merganser Ct Unit #A, Chester

Listing courtesy of Keller Williams Flagship. Contact:

$399,000
2 Beds ⋅ 2 Baths
Waterfront with assigned pier 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
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
$929,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2943, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$829,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2932, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$999,990
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
2 Beds ⋅ 3 Baths
Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2911, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$829,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2933, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$749,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private workspace. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with seat and handheld shower wand, double sinks, and quartz countertops for added convenience and style. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

110 Boatswain Way Unit #3042, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$600,000
5 Beds ⋅ 4 Baths
$10,000 Buyer Credit with an Acceptable Offer! Use it to Buy Down Your Rate! Use it to Build a Deck! Like new and loaded with upgrades, this stunning end-unit Baldwin townhome is just three years young and offers the perfect blend of style, space, and convenience. Featuring 4 bedrooms, 4 full baths, and 1 half bath, this spacious home was thoughtfully designed for modern living. The heart of the home is the bright white gourmet kitchen complete with quartz countertops, abundant cabinetry, a large center island, and an expanded kitchen/dining bump-out that creates an open and inviting space for entertaining. The adjoining living areas boasts a shiplap focal wall with fireplace and is filled with natural light thanks to the premium end-unit location. Retreat to the luxurious owner's suite with a private bath, while additional bedrooms and baths provide flexibility for family, guests, or a home office. Take outdoor living to the next level on the incredible rooftop deck, perfect for relaxing, entertaining, or enjoying sunset views. Additional features include an attached garage, modern finishes throughout, and the peace of mind that comes with newer construction. Conveniently located in the Ellendale community that offers an outdoor pool, community center, playground, ponds and fishing pier with kayak launch. Close to shopping, dining, commuter routes, and everyday amenities, this turnkey home offers low-maintenance living without sacrificing space or style.

310 Allison Jane Dr Unit #H-1, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810
$449,000
3 Beds ⋅ 2 Baths
Immaculately maintained and tucked away on a quiet street, this charming home offers the perfect blend of privacy and convenience with easy access to Route 50—ideal for commuters. Thoughtfully designed as an elevated residence, the home is built above grade to help reduce flood risk while providing a versatile lower level complete with a hobby room and attached garage. The main living level boasts a bright, open-concept floor plan where the kitchen, dining, and living areas flow seamlessly together, creating an inviting space for both everyday living and entertaining. A beautiful sunroom, surrounded by windows, fills the home with abundant natural light and opens to a wraparound balcony, extending the living space outdoors. Also on the main level is a flexible bonus room that can easily serve as a home office, den, studio, or other space to suit your lifestyle. Upstairs, you'll find two spacious bedrooms, a full bath, and a conveniently located laundry area. Large windows throughout the home create a warm, light-filled atmosphere, while the fully fenced yard provides a secure space for pets, play, or outdoor enjoyment. Combining comfort, versatility, and an excellent location, this delightful property is a must-see for buyers seeking a peaceful setting with convenient access to shopping, dining, and major commuter routes.

121 Marshy Creek Rd, Grasonville

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$525,000
2 Beds ⋅ 3 Baths
Welcome to resort-style living at K. Hovnanian's Four Seasons at Kent Island — one of the Eastern Shore's premier 55+ waterfront communities on the Chesapeake Bay. This Magothy model condo offers approximately 2003 sq. ft. of thoughtfully designed single-level living, featuring 2 bedrooms — each with its own attached bathroom — plus a powder room for guests, a private home office with French doors, oversized walk-in closets in both bedrooms, a dry bar, and a private deck to unwind and take in the coastal air. A private climate-controlled storage room and a 1-car private garage complete the low-maintenance, lock-and-leave lifestyle this community is known for. Residents enjoy access to a beautifully appointed in-building community room, perfect for relaxing, entertaining, or working from somewhere other than your unit. Your HOA dues unlock access to the award-winning 24,000-sq.-ft. Chester House clubhouse — the true heart of the community — with indoor and outdoor swimming pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom for private events. Outside, residents enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and 4.3+ miles of walking and biking trails connecting to the Cross Island Trail. Water lovers will love the 450-foot community pier on the Chester River with boat slips, plus canoe and kayak launch and storage — all just steps from the clubhouse. Live entertainment and community life never stop, with a full-time lifestyle director curating year-round programming: walking club, water aerobics, Zumba, mahjong, kayaking outings, holiday parties, and concerts and movie nights at the community's outdoor waterfront amphitheater. This is more than a home — it's a resort lifestyle every single day. Minutes to Kent Island's shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for trips to Annapolis, Baltimore, and Washington D.C. Don't wait to start living the Four Seasons lifestyle — schedule your private showing today.

230 Switchgrass Way Unit #12, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$490,000
2 Beds ⋅ 3 Baths
Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright, open floor plan, gorgeous luxury vinyl plank flooring, and the seamless flow between the kitchen, dining, and living spaces—ideal for entertaining while still offering comfortable, defined living areas. The gourmet kitchen opens effortlessly into the main living space, while the dedicated home office features custom built-in cabinetry, display shelving, and accent lighting, creating an inviting workspace or library. Throughout the home you'll find quality upgrades including plantation shutters in both bedrooms, custom closet organization systems, ceiling fans, and a built-in wireless audio system with a Samsung Frame TV, blending everyday comfort with modern convenience. The spacious primary suite offers a relaxing escape, while the thoughtfully designed split-bedroom layout provides privacy for overnight guests. One of this home's most captivating features is the private balcony overlooking protected wooded surroundings, where you'll enjoy peaceful mornings with coffee while watching deer, birds, and the abundant wildlife that make Kent Island so special. Just outside your door, enjoy convenient access to the Cross Island Trail, nearby Macum Creek, and community kayak storage—perfect for embracing the Eastern Shore lifestyle. Residents of Four Seasons at Kent Island enjoy a truly carefree lifestyle with exterior maintenance, landscaping, and common areas maintained by the HOA, making it easy to lock the door and travel without worry. Resort-style amenities include a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, walking trails, and an active calendar of clubs and social events. Beautifully upgraded, impeccably maintained, and ideally situated, this former model home offers a rare opportunity to enjoy resort-style living surrounded by the natural beauty of Kent Island.

1000 Herons Nest Way Unit #23, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$1,400,000
5 Beds ⋅ 4 Baths
Experience the best of Waterfront living at 952 Chester River Drive, where panoramic water views, spectacular sunsets, and thoughtful custom design come together to create an exceptional waterfront retreat. Offering over 3,500 square feet of living space, this custom-built home is perfectly positioned to capture endless water views from nearly every room. High ceilings and expansive windows fill the home with natural light while framing the ever-changing waterfront backdrop. Designed for both everyday living and effortless entertaining, the main level features an open floor plan that seamlessly connects the living, dining, and kitchen spaces. The gourmet kitchen is equipped with gas cooking, abundant cabinetry, and generous workspace, allowing you to prepare meals while enjoying stunning views of the water. With five bedrooms and three-and-a-half baths, there is plenty of room for family and guests. Thoughtful design elements throughout the home maximize both functionality and comfort while keeping the focus on the incredible waterfront setting. Step outside and discover a boater's dream. The private pier is equipped with electric, water, three boat lifts, including a 20,000-pound lift, 10,000-pound lift, and 2,500-pound lift, offering exceptional flexibility for multiple vessels and watercraft. Spend your days on the water and return home to breathtaking sunsets over the Chester. Additional features include a NEW roof, 2 - 1 year old HVAC systems, tankless hot water heater, attached two-car garage with excellent storage, 50 amp RV hook up, and the quality craftsmanship expected in a custom-built waterfront residence. Whether you're searching for a year-round residence or the ultimate waterfront getaway, 952 Chester Beach Road offers a rare opportunity to enjoy unmatched views, premier boating access, and the relaxed lifestyle that makes Maryland's Eastern Shore so special.

952 Chester River Dr, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810
$1,750,000
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 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
$1,350,000
4 Beds ⋅ 3 Baths
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
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
$750,000
4 Beds ⋅ 4 Baths
335 S. Carolina Rd is ready for its 2nd owner! Enjoy sprawling views of the Chesapeake Bay from every level. Only 3 years young, this home is beautifully appointed and move in ready. As you enter, the first floor opens to a living space with a slider that leads to your lush green back yard. There is also a full bathroom and bedroom. The second floor is where the magic is. Your living room with fireplace, kitchen and dining space are open for you to enjoy the spectacular water views from all angles. The third floor boasts 3 bedrooms and 2 full bathrooms including the waterside primary suite with its own private deck. Some special features include a bright open floor plan, balconies with water views, a gorgeous fire pit, and walkable to the Bay and beach. Also enjoy a widened driveway for extra parking spaces, a water softener system and storage shed. This home features 3 decks and a 2 car garage. Move in time to enjoy all that a beautiful Kent Island summer has to offer.

335 S Carolina Rd, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$435,000
3 Beds ⋅ 3 Baths
Welcome to Bayside, where coastal living and resort-style amenities come together in one of the area’s most desirable waterfront communities. This 3-bedroom, 2.5-bath condo offers a relaxing marina-side setting with both upper and lower decks overlooking the marina, creating the perfect backdrop for morning coffee, evening sunsets, and everything in between. Inside, you’ll find a spacious layout designed for comfortable living, complete with a cozy gas fireplace, generous living spaces, and the convenience of a 1-car garage. Recent improvements include new carpet on lower level, a new roof in 2023 and the front foot fee paid off in 2024, as well as a one-year home warranty for the buyer — adding additional value and peace of mind for the next owner. Life in Bayside is all about lifestyle. Residents enjoy access to resort-style amenities including a clubhouse, outdoor pool, fitness center, tennis courts, volleyball courts, and scenic walking and jogging trails — all just steps from the marina and moments from the Chesapeake Bay. Perfectly located near waterfront restaurants, local shops, and major commuter routes to Annapolis, Baltimore, and Washington D.C., this home offers the ideal blend of relaxation and accessibility. Whether you’re searching for a full-time residence or the perfect weekend waterfront escape, this Bayside condo captures the very best of Eastern Shore living.

106 Bodys Neck Rd, Chester

Listing courtesy of Realty Navigator. Contact: 4106433404
$795,000
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 boat slip - #49 - 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
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
$689,900
4 Beds ⋅ 3 Baths
One of our most popular designs, the Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs accommodates four nicely sized bedrooms, including aprimary suite with a massive closet area. Located just a short walk to the waterfront, the community features a boat launch, pavillion, playground, and bayfront recreational area.

114 Queens Colony High Rd, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

$994,000
5 Beds ⋅ 3 Baths
Welcome to this stunning custom home overlooking the 10th green in the prestigious Prospect Bay community. Situated on a beautiful one-acre lot, this residence offers over 3,000 square feet of living space with 4-5 bedrooms and an ideal floor plan for everyday living and entertaining. The dramatic two-story foyer welcomes you into a thoughtfully designed home featuring elegant architectural details, including tray and vaulted ceilings. The bright kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, plus a separate formal dining room. Open to the kitchen, the inviting family room offers bamboo flooring, a gas fireplace, custom built-ins, and access to the expansive deck overlooking the backyard and golf course. The spacious primary bedroom includes a large walk-in closet and private bath with a soaking tub, dual vanities, and a walk-in shower. Four additional bedrooms provide flexibility for guests, a home office, or multigenerational living, including one bedroom conveniently located on the main level.  Enjoy the best of Eastern Shore living with outdoor spaces designed for relaxing and entertaining. Barbecue on the large deck or gather with family and friends for a traditional Maryland crab feast in the screened gazebo while taking in peaceful golf course views. Additional highlights include a three-car garage, oversized parking pad, main level heat pump replaced in 2021, and crawl space encapsulated in 2025. Prospect Bay residents enjoy outstanding resort-style amenities, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, boat ramp, pro shop, and an active social calendar. Ideally located just minutes from the Chesapeake Bay Bridge, this lovely home offers the perfect combination of golf, boating, and relaxed coastal living.

14 Fairway Is, Grasonville

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

$5,400,000
7 Beds ⋅ 9 Baths
Designed to rival a private resort, this waterfront estate was built for celebrating with family and friends. Sweeping Chesapeake views set the stage for every gathering. The waterfront pool features a cascading rock waterfall, a tucked in bench, and a generous sun shelf, all overlooked by a pool house with a covered summer kitchen, bar, seating area, and full bath with AC. A curated firepit lounge, expansive patios and balconies, and a screened waterside porch bring indoor and outdoor living together for every occasion. At the shoreline, life on the Bay begins, with an expansive private beach perfect for wading, sandcastles, and quiet evenings by the water. The newly expanded L shaped pier stretches 260 feet and is engineered for serious boating, with dockage for a large yacht, 24,000 lb. and 10,000 lb. lifts, electric, R/O water, dual pedestals, and decorative lighting. Protected waters offer calm conditions for docking, fishing, crabbing, and watersports, with direct Bay access and easy cruising to Annapolis, St. Michaels, and beyond. A circular driveway centered by a gorgeous fountain leads to the entry, where a stunning two story foyer and grand staircase greet you, framed by spectacular water views. The great room features a soaring wall of glass and a fireplace, opening to a chef's kitchen appointed with Wolf and Sub Zero appliances, custom cabinetry, a conversation bar, pantry, and breakfast nook. The dining room seats twelve or more, ready for every holiday feast. The primary suite is a private waterfront retreat, with a sitting area beneath a domed ceiling, a fireplace, custom built ins, and a spa bath with heated floors, a jetted soaking tub, and a multi head shower. The waterfront game room offers a fireplace, wet bar, and large TV, while the private theater seats eight in front of a 100 inch screen, making this home the destination for family and friends year round. Upstairs, five architecturally unique bedrooms, three ensuite, include private waterfront balconies and a large activity room opening to a deck overlooking the pool, dock, creek, and bay. A fully equipped in law suite offers its own kitchen, living area, bedroom, fireplace, and attached two car garage, while a separate heated and cooled four car garage with porcelain tile and custom cabinetry serves as studio, workshop, or gym. Six fireplaces, Anderson and Palladian windows, tankless water heaters, a whole house water softener and reverse osmosis system, a 60KW whole house generator, and fiberoptic 2.5GB internet with seventeen access points bring comfort and connectivity throughout. Fully app based control manages lighting, HVAC, security, pool, spa, generator, music, locks, and network, inside and out. Tucked along a quiet private road with easy access to the Bay Bridge, Annapolis, and Washington D.C., this is waterfront vacation living designed to be experienced every day. Serenity Lane describes how you feel, not just where you are. Welcome home.

330 Serenity Ln, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$969,000
4 Beds ⋅ 3 Baths
STUNNING NEW CONSTRUCTION – Experience the pinnacle of modern luxury in this exquisite "Farmhouse Chic" masterpiece, perfectly situated in a highly coveted Kent Island community near the shores of the Chesapeake Bay. Offering over 2,600 square feet of meticulously crafted living space, this residence features 4 spacious bedrooms, 2.5 designer baths, and a versatile retreat living space tailored for contemporary life, with optional 5th and 6th bedrooms. Covell Signature Homes provides well-crafted homes specified to fit YOUR needs! Act soon and you can DESIGN YOUR DREAM HOME the way YOU want it, with all the finishes, options and features that work for YOUR life. The home’s striking exterior sets the stage for the upscale finishes found within. Step inside to an expansive open-concept Great Room and a gourmet kitchen designed for the culinary enthusiast, complete with high-end stainless-steel appliances, premium countertops, and a massive island perfect for entertaining. Durable, luxury vinyl plank flooring flows seamlessly throughout the main areas, leading to a dedicated private study—the ideal sanctuary for a home office or library - or an optional 5th bedroom. Retreat to the upper level where the additional living area provides a second gathering spot, while the primary suite offers a spa-like escape. The retreat living space can also convert to a 5th or 6th bedroom. Every inch of this home reflects a commitment to quality and style, blending rustic farmhouse charm with sophisticated, high-end details. The lifestyle is equally unmatched. Located in a premier water-access community, you can keep your boat at the Queen Anne Marina, enjoy a round of golf at the adjacent Blue Heron Golf Course, or explore the island’s famous waterfront dining just minutes away. This is more than a home; it is an incredible opportunity to own a piece of the Kent Island dream!

416 5 Farms Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686