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$389,900
3 Beds ⋅ 3 Baths
Bayside In Kent Island Located in the Popular Community of Bayside just minutes from the Bay Bridge and all Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a Concrete Patio. The next level up opens to an Expansive Living Room/Dining Room combo with gleaming hardwood floors, propane gas Fireplace w mantle and sliding glass doors to a rear facing Deck. The Half Bath & L-Shaped Kitchen with pass thru are located in the front of the home, and the Kitchen is nicely updated to include stainless steel appliances, white cabinets, quartz counters, modern oversized sink with single lever faucet and wonderful wall of built-in storage/pantry space.

108 Blenny Ln, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$6,000,000
For Sale or Lease! Positioned at the gateway to Kent Island, 1406 Main Street commands 1.78 acres with dual frontage on U.S. Route 50/301 and Main Street — among the most visible corners on Maryland's busiest Eastern Shore corridor. The site holds a three-building commercial complex of approximately 12,034 square feet: a large retail store fronting Route 50, a separate retail building addressing Main Street, and service space totaling nine drive-in bays.

1406 Main St, Stevensville

Listing courtesy of SVN/Miller Commercial Real Estate. Contact: 410-543-2440
$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! Qualified buyers may receive a 5.875% INTEREST RATE for the first year at no cost through our preferred lender!

116 Oyster Cove Dr Unit #1D, Grasonville

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$700,000
3 Beds ⋅ 3 Baths
Newly adjusted price. 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
$599,900
3 Beds ⋅ 4 Baths
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

Listing courtesy of Redfin Corp. Contact: 3016586186
$699,000
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
$309,900
3 Beds ⋅ 3 Baths
Motivated Seller! This home is move in ready. Discover refined waterfront community living in this beautifully updated and rarely available 3-bedroom, 2.5-bath condo in the highly desirable Queen’s Landing community. Thoughtfully designed with both comfort and style in mind, this spacious home offers fresh interior paint, an inviting open layout, and a beautifully updated kitchen featuring elegant quartz countertops—perfect for everyday living, relaxing weekends, and entertaining family and friends. Natural light fills the living spaces, while the seamless flow between the kitchen, dining, and living areas creates a warm and welcoming atmosphere throughout the home. Step outside to enjoy your private screened porch—ideal for morning coffee or evening unwinding—or host summer gatherings on the private patio designed for grilling and outdoor entertaining. Rare opportunities like this don’t come along often in Queen’s Landing, especially with the combination of three bedrooms, modern updates, and exceptional outdoor living spaces. Enjoy a true resort-style lifestyle with community amenities that include a swimming pool, fitness center, pickleball and tennis courts, and a private marina. Whether you’re looking for a full-time residence, weekend retreat, or low-maintenance coastal lifestyle, this home offers the perfect balance of relaxation and convenience. Ideally located in the heart of Chester, you are just minutes from waterfront dining, shopping, entertainment, and major commuter routes—making it easy to enjoy everything the Eastern Shore has to offer while staying connected to Annapolis, Baltimore, and Washington, D.C.

54 Queen Caroline Ct, Chester

Listing courtesy of Island Realty, LLC. Contact:

$425,000
3 Beds ⋅ 4 Baths
THIS TOWNHOME IS NOT ONLY A VALUE FROM A PRICE PER SQUARE FOOT, THE SELLER IS OFFERING TO PAY ONE YEAR OF HOA FEES $8,040. SO YOU WILL NOT HAVETO PAY FEES FOR A YEAR PERIOD! Waterfront Lifestyle with Included Boat Slip – Bayview at Kent Narrows Experience the best of Eastern Shore living in this beautifully renovated 3-bedroom, 3.5-bath contemporary townhouse with garage, ideally located just over the Kent Narrows Bridge in the sought-after Bayview waterfront community. Waterview's from second and third floor bedrooms. This move-in-ready home features a stunning new kitchen with stylish gray shaker cabinetry, granite countertops, and stainless-steel appliances. The open-concept living and dining areas are enhanced by new luxury vinyl plank flooring, creating a modern, inviting space perfect for everyday living and entertaining. The spacious primary suite offers vaulted ceilings, abundant natural light, a ceiling fan, double closet plus walk-in closet, and a dressing area. The completely renovated spa-inspired primary bath is a true showstopper, featuring a luxurious oversized double shower with dual shower heads, built-in benches, niches, and sleek glass doors. Two additional generously sized bedrooms provide excellent flexibility, including one with a private en-suite bath, plus a third full bathroom for guests. Step outside and embrace the water-privileged lifestyle this community offers. Your assigned boat slip is in the private community marina, complete with water and electricity, and included in the monthly condo fee. Launch directly into Muddy Creek, which leads straight to the Chester River—putting you just minutes by boat from Red Eye Dock Bar, Harris’ Crab House, and The Dock House Restaurant.

109 Bayview, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com