Rolling Hills (Chesapeake Isle) Real Estate

Rolling Hills (Chesapeake Isle) Real Estate

Welcome to Rolling Hills, a picturesque subdivision nestled in the heart of Chesapeake Isle, North East, Maryland. This charming community is the perfect blend of serene living and modern convenience, making it an ideal choice for families, retirees, and everyone in between.

Rolling Hills boasts a variety of beautifully designed homes, each with its own unique character and style. Whether you are seeking a cozy cottage or a spacious family residence, you’ll find a diverse selection of properties that cater to different tastes and budgets. The lush landscapes and well-maintained lawns create an inviting atmosphere, perfect for leisurely strolls or afternoon picnics.

One of the standout features of Rolling Hills is its close-knit community vibe. Neighbors often come together for seasonal events and gatherings, fostering friendships and a sense of belonging. The subdivision is surrounded by nature, with scenic walking trails and parks just a stone's throw away, ideal for outdoor enthusiasts and families looking to explore the great outdoors.

Additionally, Rolling Hills is conveniently located near the charming town of North East, where residents can enjoy a variety of local shops, restaurants, and recreational activities. The nearby waterfront offers opportunities for boating, fishing, and enjoying stunning sunsets over the Chesapeake Bay.

With its combination of natural beauty, community spirit, and convenient access to local amenities, Rolling Hills in Chesapeake Isle is more than just a place to live; it’s a place to call home. Discover the lifestyle you’ve been dreaming of in this enchanting Maryland subdivision!

Newest Listings in Rolling Hills (Chesapeake Isle)

$375,000
3 Beds 2 Baths
Welcome to 88 Caldwell Rd where the vacation lifestyle you've been dreaming of can be yours year-round! Tucked away on a spacious 1.05-acre lot in the waterfront community of Chesapeake Isle, this 3-bedroom, 2-full-bath home offers the perfect blend of privacy, outdoor living, and access to the water. Step inside to a newly remodeled kitchen featuring granite countertops and stainless steel appliances. The flexible floor plan offers plenty of room to spread out, including a possible 4th bedroom, home office, guest space, or bonus room in the basement. A walkout basement provides direct access to the fenced backyard, while the large front deck and backyard patio give you multiple places to entertain, or simply enjoy the peaceful wooded surroundings. Big-ticket updates and features add even more value, including HVAC in 2020, water heater in 2022, whole-house generator, and attached garage with interior access. The large driveway provides plenty of parking with room for your boat, trailer, and other outdoor toys. Chesapeake Isle is a water enthusiast's dream, offering a community boat ramp, mooring area, dinghy and kayak storage, private beach, pavilion, and volleyball/pickleball court, along with an active community social calendar. Enjoy easy access to the Elk and North East Rivers and spend your weekends boating, kayaking, fishing, or relaxing by the water. Located next to Elk Neck State Park and Turkey Point Lighthouse and just minutes from downtown North East's restaurants, shops, marinas, and waterfront attractions, this home puts outdoor adventure and small-town charm right at your fingertips. Bring your boat, bring your toys, and start enjoying the Chesapeake lifestyle!

88 Caldwell Rd, North East

Listing courtesy of RE/MAX Chesapeake. Contact:

Start Your Search