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$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 quartz countertops, 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. HVAC and washer/dryer are 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:

$998,000
3 Beds ⋅ 3 Baths
Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional inside storage room. This 2600 Sq Ft home is flooded with natural light and has numerous quality upgrades including custom shiplap in most of the rooms, custom ceiling fans and dining room light fixture, custom built his and hers walk in closets. The primary bath has upgraded tile, shelving for more storage, mulitple shower heads and back and front lit vanity mirrors. The gourmet kitchen is designed to impress, featuring elegant quartz countertops,premium appliances and a Wolfe induction cooktop. The island has been upgraded with shiplap as well. Thoughtful upgrades continue throughout the entire home with custom blinds with remote control, a gas fireplace,9 FT ceilings with tray ceilings in the living room and primary suite. A wet bar has also been added to the dining area.The large primary bedroom comes complete with a sitting area/office with exceptional waterviews. It also offers custom designed his -and -her closets that provide both style and storage. This unique residence offers a peaceful setting where you can relax and enjoy the ever-changing waterfront vistas. Whether you are enjoying your morning coffee or entertaining guests, this home offers the perfect blend of sophistication, comfort, and low maintenance waterfront living.

111 Marshgrass Way Unit #41, Chester

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

$749,900
3 Beds ⋅ 2 Baths
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
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
$550,000
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
$395,000
3 Beds ⋅ 2 Baths
This charming ranch-style home, renovated in 2020, offers a perfect blend of modern comfort and classic appeal. With a thoughtfully designed living space, this residence features three inviting bedrooms and two full bathrooms, including a luxurious primary bath with upgraded countertops and a walk-in tiled shower. The heart of the home is the spacious eat-in kitchen, complete with stainless steel appliances, an island for casual dining, and a family room that flows seamlessly off the kitchen, making it ideal for gatherings. Natural light abounds and the recessed lighting & ceiling fans enhance the warm ambiance throughout. Step outside to enjoy the maintenance-free deck and porch, perfect for relaxing or entertaining while overlooking the level fenced rear yard. Abundant off-street paved parking for numerous boats, RV's & vehicles. Situated in a welcoming community, this home is surrounded by well-maintained parks and recreational areas, providing ample opportunities for outdoor activities including; boating, fishing/crabbing, cook-outs & swimming on the sandy beaches along the scenic Chesapeake Bay. With easy access to restaurants, shops and a friendly neighborhood atmosphere, this property is not just a house; it's a place to create lasting memories. Experience the comfort and community spirit that this lovely Stevensville home and Kent Island lifestyle has to offer!

105 Bobbit Ct, Stevensville

Listing courtesy of Beam Realty Group, Inc.. Contact: 4438656969
$600,000
2 Beds ⋅ 3 Baths
Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

1000 Herons Nest Way Unit #43, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$599,000
3 Beds ⋅ 2 Baths
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
$700,000
3 Beds ⋅ 3 Baths
Newly adjusted price. Please visit me at the OPEN HOUSE this Sunday from 1-3pm. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River. The gourmet kitchen is the heart of the home, showcasing a large island, premium appliances, and picturesque water views. Three spacious bedrooms, two-and-a-half baths, and inviting living spaces provide comfort and flexibility for everyday living and entertaining. Enjoy spectacular sunrises, abundant wildlife, and peaceful water views from your private balcony. Just steps away, you'll find creekside trails, kayak launches, picnic areas, and direct access to the natural beauty that makes Kent Island so special. Located in desirable Phase One, this penthouse offers enhanced privacy, mature surroundings, and freedom from nearby construction. Additional features include an oversized attached garage with interior access and a secure storage room. Residents enjoy access to Four Seasons' exceptional amenities, including a 24,000-square-foot clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, fishing pier, kayak launches, dog parks, walking trails, tiki bar, and more.

2000 Herons Nest Way Unit #401, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$700,000
2 Beds ⋅ 3 Baths
Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its replacement value. Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four Seasons so desirable. 132 Wheelhouse Way offers one of the most desirable locations in the community, with exceptional water views, ground-level access, and an easy walk to the resort-style amenities. Inside, you'll find a gourmet kitchen with quartz countertops, GE Café double wall ovens, upgraded stainless steel appliances, luxury vinyl plank flooring, and an open-concept living space with an electric fireplace and beautiful water views. The primary suite features patio access, a walk-in closet, and a luxurious bath, while the second bedroom suite and private office provide comfort and flexibility. Residents enjoy the Chester House Clubhouse, indoor and outdoor pools, a fitness center, pickleball and tennis courts, walking trails, a kayak launch, fishing pier, dog park, tiki bar, and more. Perfectly located on Kent Island, this home offers an exceptional blend of luxury, convenience, and the Chesapeake Bay lifestyle.

132 Wheelhouse Way Unit #11, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$224,900
3 Beds ⋅ 2 Baths
Rarely available first floor condominium centrally located on Kent Island and in the Thompson Creek Community. Enjoy all the amenities of this water access community including the pool, tennis courts, clubhouse, and within a short walking distance to the water where you sit in a quiet community of proud homeowners. As you arrive, you will notice the peace and tranquility this community offers. Open the door and you will be greeted by the ample living room which features a cozy corner fireplace, plenty of sunlight that fills the home and sliders leading to the private covered balcony where you can enjoy views of the sunsets. Take advantage of the small outside storage closet. The kitchen provides everything a passionate cook needs to prepare even the most elaborate of meals. The primary bedroom features large windows, an ample closet and its private full bath. The other two bedrooms are equal in size and also offers sufficient space for a growing family. Another full bath can be found in the hallway. This condo offers PLENTY of parking and SUPER convenient location - less than 5 minutes to the Bay Bridge, Restaurants, Shopping, and ALL that the Island life has to offer.

1603 Marion Quimby Dr, Stevensville

Listing courtesy of Northrop Realty. Contact: 4105310321
$295,000
2 Beds ⋅ 2 Baths
Experience the ease of resort-style, maintenance-free living in this beautifully updated upper-level condominium featuring open views, abundant natural light, and the privacy of having no neighbors above. Hardwood floors, soaring vaulted ceilings, and a cozy gas fireplace create a warm and inviting atmosphere throughout the main living area. The spacious primary suite offers a peaceful retreat with a generous bedroom, ample closet space, and a private ensuite bath. A second bedroom provides exceptional flexibility as a guest room, home office, or space for family and grandchildren. The updated kitchen is equipped with newer appliances, including a refrigerator, microwave, washer, dryer, garbage disposal and hot water heater. The adjoining dining area overlooks sliding glass doors leading to a private balcony where you can relax and enjoy the expansive open views. Beyond the home, enjoy an exceptional lifestyle with access to community amenities including a clubhouse, swimming pool, pickleball courts, and fitness center. A marina is within walking distance, making it easy to enjoy boating and waterfront activities. The cross trail is just steps from your condo. The condominium association handles exterior maintenance and community upkeep, allowing you more time to enjoy the things you love. Ideally situated near fine dining, shopping, and cultural attractions, this location also offers outstanding accessibility—within easy reach of three international airports—making travel convenient whether for business, family visits, or leisure. This is the perfect opportunity to enjoy a low-maintenance lifestyle without sacrificing comfort, convenience, or amenities. "Elevated living, exceptional amenities, and a carefree lifestyle—all in one remarkable home."

114 Merganser Ct, Chester

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483
$680,000
3 Beds ⋅ 3 Baths
A rare blend of coastal proximity and refined living unfolds within this beautifully appointed corner residence in the sought-after 55+ waterfront community of Four Seasons at Kent Island. Built in 2024 and impeccably maintained , this like-new residence offers the comfort of immediate enjoinment without the wait for new construction. Positioned near a tranquil creek leading to the Chesapeake Bay, the home offers a lifestyle deeply connected to the water without the demands of direct waterfront ownership. Sunlight fills the open-concept layout through the residence’s desirable corner positioning, highlighting soaring ceilings, luxury vinyl plank flooring, and thoughtfully selected finishes throughout. The gourmet kitchen flows seamlessly into the dining and living areas, creating an inviting space for both quiet evenings and entertaining. Just beyond, a private balcony offers peaceful green surroundings with subtle water views, extending the home’s living space into a serene outdoor setting. The spacious primary suite serves as a private retreat with walk-in closets and a beautifully finished en-suite bath, while two additional bedrooms provide flexibility for guests, hobbies, or a home office. Residents of Four Seasons at Kent Island enjoy access to resort-style amenities including indoor and outdoor pools, fitness center, clubhouse spaces, pickleball and tennis courts, scenic walking trails, kayak launch, and fishing pier. Conveniently located near Kent Narrows, Annapolis, and Route 50, this exceptional residence offers a refined Eastern Shore lifestyle with easy access to dining, recreation, and waterfront experiences.

111 Marshgrass Way Unit #21, Chester

Listing courtesy of Samson Properties. Contact: 2406308689
$485,000
2 Beds ⋅ 3 Baths
BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet kitchen is equipped with upgrades from the stunning kitchen island with quartz counter tops, beautiful upgraded cabinetry to the GE Profile appliances. This kitchen is designed for everyday living as well as hosting the occasional dinner party. The primary bedroom, is a separate self-contained suite complete with two closets and a luxury owners' bath that includes double sinks, and quartz countertops. The bright and airy 2nd bedroom is also a separate suite with a full bath and an oversized walk-in closet. In addition to the two bedrooms, there is a home office with stylish French Doors and a powder room for guests. The separate laundry room is equipped with a GE washer and dryer. This home also has a garage with adjoining driveway/parking space and large personal storage room which is a few short steps from the elevator. This home is just a short walk to resident kayak racks with launch access to the Chester River. KEEP IN MIND THIS CHESTER MODEL, WITH PLENTY OF FEATURES AND UPGRADES INCLUDED, IS MOVE-IN READY AND PRICED TO SELL***** Award-winning 24,000 Square Foot Clubhouse with Stunning Chester River Views! Fantastic amenities include 4.3 miles of walking trails throughout the community, 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, lighted pickle ball courts, 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, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

1000 Herons Nest Way Unit #22, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$765,000
2 Beds ⋅ 3 Baths
Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floor unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design seamlessly connects the living room, dining area, and kitchen areas, all enhanced by expansive windows letting in an abundant amount of natural light. Experience resort style living in the highly sought after Four Seasons at Kent Island, a premier 55+ waterfront community. Residents enjoy access to world class amenities, including indoor and outdoor pools, walking trails, a Chester River pier. Ideally located just minutes from waterfront dining, shopping, and the Chesapeake Bay Bridge, this home offers the perfect blend of relaxation, convenience and low maintenance living at its finest.

111 Marshgrass Way Unit #43, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$515,000
2 Beds ⋅ 3 Baths
WATERFRONT Condo! Open House dates scheduled. Beautifully renovated 2BR/2.5BA waterfront condominium located in the sought-after Queen’s Landing resort-style community on the scenic Chester River, just off the Chesapeake Bay. This move-in-ready home showcases a stunning top-to-bottom remodel, including new luxury vinyl plank flooring, new carpet, fresh paint throughout (ceilings, walls, trim, and doors), new white cabinetry, beautiful quartz countertops with beveled white backsplash, updated bathroom vanities, flooring and modern lighting fixtures. The light-filled open floor plan is designed to highlight the panoramic Chester River views. The spacious family room off the kitchen features an oversized sliding glass door leading to a private balcony with beautiful eastern water views—perfect for morning coffee or relaxing evenings overlooking the river. Upstairs, the primary bedroom suite offers elevated water views and a private full bath. A second large bedroom and additional full bath complete the upper level, with washer and dryer conveniently located between the bedrooms. Residents of Queen’s Landing enjoy exceptional waterfront amenities including a private marina, swimming pool overlooking the Chester River, clubhouse, fitness center, tennis and pickleball courts, and scenic waterfront walking paths. Ideally located just minutes from shopping, dining, entertainment, the Cross Island Trail, and the Chesapeake Bay Bridge, this home is perfect as a full-time residence or weekend waterfront retreat on Maryland’s Eastern Shore. Schedule your private tour today!

34 Queen Anne Way, Chester

Listing courtesy of Taylor Properties. Contact:

$530,000
2 Beds ⋅ 3 Baths
Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 towards Capital Contribution Fee * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane gas cooktop with range hood, wall oven + microwave combo and a huge Island that accommodates plenty of bar seating. Spacious Bedroom suites each with private full baths and generous closet spaces. The Primary bath has His 'n Her's double sinks with Moen fixtures, comfort height vanities, large vanity mirrors, medicine cabinets and a walk-in tiled shower with seat. The Primary bedroom features 2 closets; one walk-in-closet and one generous wall closet, a ceiling fan and a single French door to access the balcony. The 2nd Bedroom is large enough to hold a traditional sized bedroom set and features a tub/shower combo in the bath. The open Great Room is large, bright and has serene pond views and winter water views of Macum Creek with oversized sliders to a covered balcony. You will love the convenient laundry room located off the foyer area that accommodates the included full-sized GE washer and dryer. Elevator down to the Lobby level to your private garage and a just a few steps down the corridor is your private, keyed storage closet. This condo building features a secure lobby entrance and is impeccably decorated and maintained. Additionally, the 2nd floor has a common Club Room/Meeting Room great for socializing with your neighbors or as additional entertainment space. It features Public Water, Public Sewer, individually metered propane gas heat and cooking. All residents have access to the community amenities which include a huge 20,000 sf Club House with Billiards Room, Casual Lounge Area, Fitness Center, Party and Meeting rooms, and fabulous Indoor Heated Pool & Spa. Outside awaits a resort-like Pool, Cabana House, Private Beach Area, Outdoor Concert Space, Pier for Fishing and taking in the magnificent Chester River views & Kayak launch and Walking Trails. Pickle Ball enthusiasts you are in luck as there are Tennis Courts and Pickle Ball Courts for all, and grand kids can be entertained at a small Playground Area. Come tour today and see why this is THE place to be in Kent Island for 55+ living!

4000 Herons Nest Way Unit #22, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$479,000
2 Beds ⋅ 3 Baths
A price improvement has been made, making this unit the best value in the entire community. This home shows like a model with approximately $55,000.00 in upgrades. No need to wait for new construction this unit is ready for immediate occupancy. Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. This highly sought-after first-floor condo is move-in ready and has been meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced by crown molding, recessed lighting, and direct views of the lush greenspace with seasonal water glimpses. The gourmet kitchen and dining area are ideal for entertaining, offering a spacious island with seating, quartz countertops/bar, sleek wifi enabled appliances, and seamless flow into the living room. Unwind by the cozy fireplace or open the double sliding glass doors to your private patio—perfect for watching the sunrise, morning coffee, reading, or simply enjoying the peaceful natural setting. The owner’s suite offers both a walk-in and secondary closet, private patio access, and a luxurious en-suite bath with dual sinks and a spa-inspired frameless glass shower. The guest suite is bright and spacious, complete with its own en-suite bath, custom tilework, and large vanity. A bonus room with upgraded frosted glass doors provides the perfect space for a home office, workout area, or reading nook. Additional highlights include: LVP flooring throughout the entire home, interior access to a private one-car garage, and a secure storage unit. From your patio, take a stroll along the walking trail where you can take in the sights and sounds of nature to discover tranquil views and your kayak launch. The community also has direct access to the Kent Island Cross Island Trail. Many extra amenities to enjoy including an indoor heated pool, outdoor infinity pool, firepits, pickleball and tennis courts, dog park, and beautiful walking and biking trails. Live every day like you’re on vacation—this stunning condo offers the lifestyle you’ve been waiting for and is a must see to experience all of the upgrades! Water and sewer fees are already included in the owners monthly COA.

3000 Herons Nest Way Unit #11, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686