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$859,500
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: (410) 280-5600
$249,000
Rare offering of a surveyed, perced, and cleared commercial lot with high exposure in Queen Anne County! 1.49 acres. See attached documents for survey, perc, and allowable uses. This is an exceptional location to move your existing small business to or to start your new business.

Chester River Heights Road, Millington

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$199,900
3 Beds ⋅ 2 Baths
Nestled along the water's edge, this waterfront opportunity offers a canvas to create your own Eastern Shore retreat. Whether you choose to renovate the existing 3BR cottage or build on the existing foundation there is plenty of potential. Buyer to confirm building restrictions with the county. This property features a new deep well, new well pump, and new septic holding tanks in 2026. The existing interior of the home has been taken down to the framing and includes 100-amp electrical service, providing a solid starting point for your vision. Outdoor enthusiasts will enjoy everything this property has to offer. Fish for perch, bass, catfish, and snakeheads, or spend the day crabbing from your shoreline. Waterfowl hunters will enjoy the existing duck blind, while everyone will appreciate the stunning sunsets overlooking the water. Whether you're looking for a peaceful weekend escape, a hunting and fishing camp, or the site of your future waterfront cottage, this property offers an opportunity that's becoming increasingly difficult to find.

220 Kirbys Landing Rd, Millington

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$629,900
3 Beds ⋅ 2 Baths
This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

315 Bentons Pleasure Rd, Chester

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937
$599,000
3 Beds ⋅ 1 Baths
Welcome to your dream coastal retreat in the highly sought-after Chester River Beach community of Grasonville, Maryland. This beautiful, luxurious bayside property is a single-story rancher that offers the perfect blend of modern upgrades, breathtaking views of the Bay and relaxed coastal living in a vibrant and lively neighborhood that is perfect for boating enthusiasts, crabbing, and fishing. This fully remodeled three bedroom, one full bath home sits on one of the largest corner lots and has been thoughtfully updated from top to bottom with high end finishes and brand new systems throughout. Enjoy peace of mind with newly installed roof, vinyl siding, flooring, central air conditioning system with heat pump, new well tank, and water heater. Next on the list is a completely renovated bathroom featuring a state-of-the-art smart toilet with bidet. After enjoying the beach, boating, fishing or swimming, relax in the spacious, brand new, tub and shower. Gorgeous coastal style kitchen designed with two spacious islands, providing ample prep space, including breakfast bar seating perfect for entertaining family and guests. Amenities showcasing high end cabinetry, ceramic tile backsplash, wall mounted retractable pot filler, smart appliances including flat top range, stainless double door refrigerator, double oven, and farm sink as well as other high end features! Enjoy breathtaking water views filling the space with natural light and creating a serene coastal atmosphere through two newly installed bay windows. Additional features include a cozy working fireplace, off-street parking, and a spacious detached garage equipped with electrical service. The home also includes a full, easily accessible attic, providing plenty of storage and potential to include additional living space! The property includes access to private boat docks, boat ramps, and private managed beach just a few steps away. Residents also enjoy a community park, entertainment pavilion with stunning waterfront views, along with convenient access to nearby shopping malls, restaurants, and grocery stores. Boat directly to many waterfront bars and boating restaurants making every day feel like a vacation. Whether you're looking for a full-time residence or a weekend getaway, this move-in-ready Chester River Beach home delivers the very best of Eastern Shore bayside living.

801 Chester River Dr, Grasonville

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$575,000
3 Beds ⋅ 3 Baths
*BIG PRICE IMPROVEMENT ON THIS BEAUTY* SELLER IS ALSO OFFERING CLOSING ASSISTANCE!Welcome to Bay Bridge Cove, an active adult 55+ community designed for comfort, convenience, and low-maintenance living. Residents enjoy exceptional amenities including a clubhouse with outdoor pool, fitness center, lounge, library, meeting space, and game room, along with walking trails, scenic ponds, pickleball and bocce courts, a crab shack, and community vegetable and herb gardens. Ideally located near Historic Annapolis, shopping, dining, recreation, and major commuter routes including Rt. 50, Rt. 97, the Bay Bridge, Washington, D.C., Baltimore, and the Eastern Shore. This beautifully upgraded Easton model by award-winning McKee Builders offers quality craftsmanship, energy efficiency, and thoughtful design throughout. A private gated paver courtyard creates a warm welcome, while the spacious rear deck overlooks open green space and mature trees for a peaceful outdoor setting. Inside, this meticulously maintained home offers approximately 2,000 square feet with 3 bedrooms, 3 full baths, a versatile loft, and a 2-car garage. The gourmet kitchen is appointed with upgraded cabinetry featuring pull-out shelving and soft-close doors and drawers, granite countertops, decorative backsplash, Kohler undermount stainless sink, and upgraded stainless steel appliances. Additional improvements include upgraded flooring, renovated baths, and a tankless on-demand water heater. The open and airy interior is filled with natural light from two skylights in the main living area. Architectural details include crown molding, chair rail accents, soaring foyer ceilings, cathedral ceilings in the dining and family rooms, and a tray ceiling in the primary suite. The spacious primary retreat includes two closets and a beautifully updated bath. Two additional bedrooms and two full baths, with one bedroom and bath on each level, offer flexibility for guests or multigenerational living. The loft provides ideal space for a home office, den, or reading area. A large conditioned crawl space with interior access offers excellent storage. Please note: public records do not reflect the correct square footage. Approximate finished living area is 2,000 square feet. CALL ME TODAY FOR YOUR SHOWING!

324 Moorings Cir Unit #108, Stevensville

Listing courtesy of Clark & Co Realty, LLC. Contact: 410-490-2183
$725,000
2 Lots, 2 tax parcels 3.38 acres facing US Route 50/301 on Hess Frontage Road. Quasi Private Drive shared with Delmarva Power Company right of way, Whaler Boat Sales, Furniture Sales, Zoned Urban Commercial with most uses permitted. Has a private rear right of way to County Wilson Road for possible sewer hook-up currently has existing single family residence with 1 bath, kitchen living room and 2 bedrooms, covert it to office and add your workshop, storage buildings.

144 Hess Frontage Rd, Grasonville

Listing courtesy of Tidewater Properties. Contact:

$545,000
Discover the opportunity to build your dream home on the Corsica River. This .869-acre waterfront lot offers 78 feet of direct water frontage, providing the perfect setting for boating, fishing, and enjoying the beauty of the Eastern Shore. The property has an approved perc test in place, allowing you to move forward with confidence as you design and create the home you’ve envisioned. With its peaceful setting and scenic views, this lot combines privacy and natural surroundings while keeping you connected to nearby conveniences. Rarely does a property like this become available—your waterfront lifestyle awaits.

N Hibernia Rd, Centreville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600