Chester Homes with Boat Ramp Amenities

Welcome to Chester, Maryland – a hidden gem nestled in the heart of Queen Anne’s County! This charming waterfront town offers a unique blend of serene living and vibrant community spirit, making it an ideal destination for those seeking a slice of paradise. With its picturesque views of the Chester River and proximity to the Chesapeake Bay, residents are treated to a lifestyle that embraces nature and outdoor adventure.

One of the standout features of Chester is its array of homes equipped with boat ramp amenities. Imagine stepping out of your front door and onto your boat, ready to explore the sparkling waters that surround you. Whether you’re an avid fisherman, a kayaking enthusiast, or simply love spending lazy afternoons on the water, these properties provide unparalleled access to your aquatic adventures. The boat ramps are designed for convenience, ensuring that launching and retrieving your vessel is a breeze.

In addition to its water-based activities, Chester boasts a welcoming community with local shops, eateries, and parks that highlight the area’s natural beauty. Enjoy leisurely strolls along scenic trails or gather with friends for a picnic by the river. The town’s rich history and charming architecture add character, making it a delightful place to call home.

Living in Chester means embracing a lifestyle that celebrates both relaxation and recreation. With homes featuring boat ramp amenities, you can truly immerse yourself in the joys of waterfront living. Come discover the magic of Chester, where your dream home awaits amidst the beauty of Maryland’s Eastern Shore!

Newest Chester Homes with Boat Ramp Amenities

$944,900

3 Beds ⋅ 3 Baths ⋅ MDQA2018566 MLS

Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and already through its one-year builder punch list, this home offers the ease of newer construction without the wait—plus thoughtful upgrades and finishes already in place. Situated on a premium corner lot, this impressive home features 3 bedrooms, a dedicated home office, a spacious second-floor loft and a 3-car garage, including a tandem bay with EV charger. Inside, custom details immediately set it apart, including decorative molding in the foyer and primary bedroom, upgraded chandeliers in the foyer and dining room, custom window shades and a beautiful stone propane fireplace. The kitchen showcases K. Hovnanian's upgraded Looks package with crisp white cabinetry and upgraded Thermador appliances, complemented by reverse osmosis at the kitchen sink and a whole-house water filtration system. Additional features include a Rinnai tankless water heater, two-zone HVAC with propane backup and a whole-home surge protector. Outdoor living is ready to enjoy with a paver patio, propane grill hookup, irrigation system and upgraded landscaping—no waiting for a new yard to grow in or projects to be completed. Best of all, the location puts the Four Seasons lifestyle right outside your door. Enjoy easy access to the community's pickleball courts, clubhouse, indoor and outdoor pools, fitness center, walking trails, pier, kayak launch and more. Why wait to build when you can move right into a nearly new Kerr with the premium lot, upgrades, landscaping and finishing touches already done? 275 Warbler Way delivers exceptional value and an easy, move-in-ready Eastern Shore lifestyle.

275 Warbler Way, Chester

$835,000

3 Beds ⋅ 3 Baths ⋅ MDQA2018120 MLS

Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking, unobstructed water views and exceptional community amenities, this beautifully appointed three-bedroom, two-and-a-half-bath condominium is designed for those who appreciate comfort, elegance, and low-maintenance living. The light-filled, open-concept floor plan showcases luxury vinyl plank flooring throughout, recessed lighting, and expansive windows that capture stunning views of the Chester River from nearly every angle. The spacious living room is anchored by a cozy electric fireplace and flows seamlessly into the dining area and gourmet kitchen, creating the perfect space for entertaining or relaxing. The kitchen features stainless steel appliances, a gas cooktop, white cabinetry, generous countertop space, and an inviting layout that keeps everyone connected. Just beyond the living area, step onto the expansive waterside balcony and enjoy panoramic river views, morning coffee, spectacular sunsets, and endless opportunities to watch boats glide by. The luxurious primary suite is a private waterfront retreat, complete with direct balcony access, a spacious sitting area, two walk-in closets, and an elegant ensuite bath featuring dual vanities and a large walk-in shower. Two additional bedrooms provide comfortable accommodations for guests, a home office, or hobbies. Additional highlights include a beautifully crafted built-in bar, electric blinds, a large laundry room, a dedicated storage room, and an attached one-car garage with new epoxy speckled floor. Residents enjoy an exceptional resort-style lifestyle with amenities that include indoor and outdoor swimming pools, a fitness center, clubhouse, library, billiards room, hot tub, Bocce Ball, pickleball and tennis courts, picnic areas, tot lots, and a community pier overlooking the Chester River. Ideally located just minutes from shopping, dining, golf, marinas, and the Chesapeake Bay Bridge, this exceptional waterfront residence offers the perfect blend of luxury, convenience, and carefree Eastern Shore living.

201 Switchgrass Way Unit #34, Chester

$599,900

3 Beds ⋅ 4 Baths ⋅ MDQA2017452 MLS

Experience the best of Kent Island waterfront living in this beautifully appointed home located in the sought-after Bayside community of Chester. Designed for both everyday comfort and effortless entertaining, this residence features an open-concept floor plan with abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen serves as the heart of the home, offering generous counter space, quality cabinetry, and a seamless flow into the dining and living areas. The expansive primary suite provides a private retreat with a walk-in closet and luxurious ensuite bath. Additional bedrooms and flexible living spaces offer plenty of room for guests, a home office, or recreation. Enjoy outdoor living from the private deck, perfect for relaxing and taking in the peaceful surroundings. An attached garage and ample storage add convenience to everyday life. Residents of Bayside enjoy exceptional community amenities, including a clubhouse, fitness center, swimming pool, tennis courts, walking trails, and marina access. The boat slips at Castle Marina are rented. It can be on a short term up to a yearly basis. There are some slips over on the side where Queens landing condos are that can be for sale. Ideally located near waterfront dining, shopping, golf courses, and major commuter routes, this home offers the perfect blend of Eastern Shore charm and modern convenience. Don't miss this opportunity to enjoy a resort-style lifestyle in one of Chester's premier waterfront communities. Additional parking spaces are located across the street for your convenience.

1012 Auckland Way, Chester

$435,000

3 Beds ⋅ 3 Baths ⋅ MDQA2017432 MLS

MARINA VIEWS FROM BOTH LEVELS! Discover a different side of Kent Island living at Bayside, where this spacious 3-bedroom, 2.5-bath home combines marina views, water access, an attached garage and resort-style community amenities — all just minutes from the Chesapeake Bay. The main level offers an open living and dining area with a gas fireplace and sliding glass doors leading to the deck overlooking the marina. Whether enjoying morning coffee, watching the boats come and go, or relaxing at the end of the day, the water is part of the view. Upstairs, the spacious primary suite offers something special — its own private balcony overlooking the marina, along with a primary bath featuring a soaking tub, separate shower and double vanity. Two additional bedrooms and another full bath complete the upper level. Additional highlights include new carpet on the lower level, an attached 1-car garage, a new roof in 2023, front foot fee paid off in 2024, and a one-year home warranty for the buyer. Bayside residents enjoy access to an outdoor pool, clubhouse, fitness center, tennis courts, boat ramp, pier/dock, common areas and water privileges. Waterfront dining, shopping, Route 50 and the Bay Bridge are all conveniently nearby. Looking for the Eastern Shore lifestyle without the upkeep of a traditional waterfront home? Come see what life overlooking the marina could look like.

106 Bodys Neck Rd, Chester

$1,195,000

4 Beds ⋅ 5 Baths ⋅ MDQA2016942 MLS

Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring upgraded countertops and a spacious island, flows seamlessly into the family room, perfect for entertaining. Relax in the primary suite with a lavish bath or unwind in the inviting family room by the fireplace with views out to Crab Alley. Three additional bedrooms (or two bedrooms and an office) and two baths round out the main level that offers sweeping scenic views from every vantage point. Step outside to discover a private oasis on 1.25 acres, complete with extensive hardscaping, a heated in-ground pool, and a soothing hot tub. Enjoy picturesque water views out the front and back, with access for kayaking and boating. The community amenities, including a beach, clubhouse, and tennis courts, elevate your living experience. This home is not just a residence; it's a lifestyle waiting to be embraced and enjoyed. Start living your best 'Shore Life' at 2855 Cox Neck Rd.

2855 Cox Neck Rd, Chester

$439,900

3 Beds ⋅ 2 Baths ⋅ MDQA2011168 MLS

PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is accented with stylish shiplap walls. There's Nothing Like NEW! Step onto the new flooring that leads you to three roomy bedrooms and two beautifully renovated full baths. Every detail has been attended to, with all-new windows, siding, plumbing, fixtures, electrical panel, light switches, septic work, water heater, doors, drywall, and a new HVAC system. With a recent roof and a dehumidified crawl space featuring a vapor barrier, this home is move-in ready—no worries, just settle in! The community enhances your lifestyle with access to four beaches, three boat ramps, a playground, ball fields, a basketball court, a picnic pavilion, a fishing pier, and plenty of opportunities for gatherings. This is the perfect place to create lasting memories!

1340 Queen Anne Dr, Chester

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