Chester Homes with Retirement Community Amenities

Welcome to Chester, Maryland—a hidden gem nestled in the picturesque Queen Anne’s County. This charming town is not only rich in history but also boasts a vibrant community atmosphere, making it an ideal place to call home, especially for those seeking a serene retirement lifestyle.

Chester is known for its stunning waterfront views along the Chester River, providing residents with ample opportunities for outdoor activities such as fishing, kayaking, and leisurely strolls along scenic trails. The community is tightly knit, with friendly neighbors and local events that foster a sense of belonging. Here, you’ll find a perfect blend of tranquility and convenience, as Chester is just a short drive from larger towns, offering easy access to shopping, dining, and healthcare facilities.

For those considering retirement, Chester offers an array of homes with retirement community amenities designed to enhance your quality of life. These residences often feature spacious layouts, modern kitchens, and beautiful outdoor spaces, perfect for entertaining family and friends or enjoying peaceful evenings. Many communities also provide exceptional amenities such as clubhouses, fitness centers, and organized activities, ensuring that residents can stay active and engaged.

Living in Chester means embracing a lifestyle filled with natural beauty, community spirit, and the comfort of knowing that your retirement years can be spent in a welcoming and supportive environment. Whether you’re looking to downsize or simply seeking a fresh start, Chester, MD, is the perfect place to find your dream home and enjoy the golden years you deserve. Come discover the charm of Chester—where every day feels like a vacation!

Newest Chester Homes with Retirement Community Amenities

$490,000

2 Beds ⋅ 3 Baths ⋅ MDQA2017786 MLS

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

$680,000

3 Beds ⋅ 3 Baths ⋅ MDQA2016714 MLS

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

$485,000

2 Beds ⋅ 3 Baths ⋅ MDQA2016820 MLS ⋅ Chester BLDG.

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

$765,000

2 Beds ⋅ 3 Baths ⋅ MDQA2016724 MLS

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

$530,000

2 Beds ⋅ 3 Baths ⋅ MDQA2015800 MLS

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

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