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$1,439,999
3 Beds ⋅ 3 Baths
Experience exceptional waterfront living in this stunning 3-bedroom, 2.5-bath condominium offering what are arguably the best views in the community. Positioned to capture breathtaking panoramic views of the Chester River, this home provides a front-row seat to beautiful sunrises, and the peaceful beauty of the Chesapeake Bay lifestyle. The spacious primary suite is a true retreat featuring a private sitting room, walk-in closet, and a luxurious en-suite bath. The open-concept design showcases the incredible water views throughout the main living spaces, creating the perfect backdrop for everyday living and entertaining. One of the most desirable locations in the community, this home offers protected water views with no expected future obstruction, allowing you to enjoy the scenery for years to come. Enjoy the convenience of being able to walk to the community pool and amenities without having to drive to the clubhouse. Additional features include a one-car garage with an additional storage room, plus private driveway parking, providing both convenience and storage. Enjoy the ease of maintenance-free waterfront living in one of Kent Island's premier communities, with easy access to marinas, waterfront dining, shopping, and the Bay Bridge.

129 Wheelhouse Way Unit 21, Chester

Listing courtesy of Rise Real Estate, LLC. Contact:

$585,000
2 Beds ⋅ 3 Baths
Priced well below market value! The builder can not compete with this price. Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury, convenience, and resort-style living come together in a way that few homes in the community can offer. This beautifully upgraded first-floor Magothy model is not only one of the closest residences to the Chester River, but also enjoys a premium location just one building away from the community clubhouse and only steps from the outdoor and indoor pools. One of the most unique advantages of this first-floor residence is its size. Unlike the second, third, and fourth-floor Magothy models, first-floor units offer approximately 100 additional square feet of living space, creating a more spacious and comfortable layout. Combined with more than $30,000 in post-purchase upgrades, this condo stands apart from the moment you walk through the door. By far the most impressive feature, however, is the extraordinary access to the waterfront. Step through your sliding glass doors and find yourself just moments from the Chester River. The peaceful setting allows you to enjoy water views, wildlife, and gentle river breezes from your private patio while offering one of the most coveted locations within the community. Whether you're taking a morning stroll along the shoreline or relaxing outdoors with a cup of coffee, the river feels like an extension of your backyard. Inside, luxury vinyl plank flooring flows throughout the home, complementing the bright, open floor plan filled with natural light from oversized windows and soaring ceilings. The gourmet kitchen is designed for both everyday living and entertaining, featuring a large center island, under-cabinet lighting, abundant cabinetry, and a custom dry bar area. The adjoining dining and living spaces create a seamless gathering area, highlighted by recessed lighting and a cozy electric fireplace. The spacious primary suite serves as a private retreat with dual closets and a beautifully upgraded bath featuring double vanities, custom tile work, a walk-in shower, and dual shower heads. A generous guest bedroom and adjacent full bath provide comfortable accommodations for family and visitors alike. Additional features include a private locked storage room, garage, custom finishes throughout, and a covered patio accented with stacked stone columns—an ideal place to unwind and enjoy the tranquil surroundings. With the clubhouse and pool just steps away, you'll enjoy unmatched convenience while still maintaining a peaceful and private setting. Residents of Four Seasons enjoy an exceptional resort-style lifestyle with a stunning clubhouse, indoor and outdoor pools, tennis and pickleball courts, fitness facilities, walking and biking trails, a community pier, and a full calendar of social activities coordinated by the community lifestyle director. Conveniently located near waterfront dining, marinas, golf courses, Annapolis, Baltimore, Washington, D.C., and BWI Airport, this is Eastern Shore living at its finest. Opportunities to own a first-floor waterfront-proximity unit in this location are exceptionally rare. With extra square footage, extensive upgrades, steps-to-the-pool convenience, and one of the closest locations in the community to the Chester River, this home offers a lifestyle that simply cannot be replicated.

129 Wheelhouse Way Unit 11, Chester

Listing courtesy of RE/MAX Executive. Contact:

$835,000
3 Beds ⋅ 3 Baths
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

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

$595,000
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:

$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:

$509,000
3 Beds ⋅ 4 Baths
Welcome to 114 Bayview—where your boat days get a serious upgrade. This home includes a private boat slip in the community marina with direct access to Kent Narrows, putting you just a 30-minute ride to St. Michaels, Rock Hall, or Cambridge. If you’ve been dreaming about pulling up to waterfront restaurants or spending full days on the water… this is your launch point. Back at home, enjoy front-row views of the 4th of July fireworks, all without leaving your property. Inside, this home is completely turn-key with LVP flooring, fresh paint, and an updated primary bath. Each bedroom features its own private bath, making it ideal for guests, roommates, or weekend hosting. The garage offers the storage every boater needs—perfect for kayaks, paddleboards, bikes, and all your gear. Even better? This home can be sold furnished, making it a true move-in-ready or weekend getaway opportunity. All of this—boat slip, water access, views, updates, garage, and flexibility—offered at just $509,000. If you’ve been waiting for an easy, low-maintenance way to live the Eastern Shore boating lifestyle… this is it.

114 Bayview, Grasonville

Listing courtesy of Samson Properties. Contact:

$499,000
2 Beds ⋅ 3 Baths
Four Seasons @ Kent Island - 55+ Community - Reduced! * 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 24,000 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: