Rolling Hills Homes for Sale

Rolling Hills Homes for Sale

Welcome to Rolling Hills, a picturesque subdivision nestled in the heart of Maryland, where serene landscapes meet modern living. This charming community is renowned for its lush greenery, rolling terrains, and a sense of tranquility that welcomes you home. Imagine waking up each day to the gentle sounds of nature, with the beauty of the outdoors just a stone's throw away from your doorstep.

Rolling Hills boasts a variety of homes for sale, catering to diverse lifestyles and preferences. Whether you’re a first-time homebuyer, looking to downsize, or seeking a spacious family residence, you'll find something to suit your needs. The homes here are characterized by their unique architectural styles, well-manicured lawns, and inviting interiors, designed for comfort and functionality. Many properties feature modern amenities, open floor plans, and stunning views that enhance the living experience.

Community is at the heart of Rolling Hills. Residents enjoy a close-knit atmosphere, with friendly neighbors and local events that foster connections. The subdivision is conveniently located near top-rated schools, shopping centers, and recreational parks, making it an ideal place for families and individuals alike.

If you’re ready to embark on a new chapter in a vibrant community surrounded by natural beauty, explore the homes for sale in Rolling Hills today. Your dream home awaits in this enchanting Maryland subdivision, where every day feels like a retreat. Embrace the lifestyle you’ve always desired in Rolling Hills!

Newest Rolling Hills Homes for Sale

3 Beds ⋅ 3 Baths

Skip the wait for new construction and step into this 2024-built home in Greencastle’s Rolling Hills community, where modern design, everyday convenience, and room to grow come together in one easy-to-enjoy package. The main level brings together the living, dining, and kitchen areas in a layout designed for everyday living and entertaining. The kitchen includes a refrigerator, stove, microwave, dishwasher, disposal, and freezer, while a convenient half bath completes the first floor. Upstairs, the primary bedroom features a private bath and walk-in closet. Two additional bedrooms, a second full bath, and upper-level laundry with the washer and dryer included add convenience to the layout. The full unfinished basement provides plenty of storage today with the option to create additional living space in the future for a recreation room, home gym, office, or hobby area. Additional features include an attached one-car garage with opener, driveway parking, programmable thermostat, and manageable front and rear yards. Conveniently located near the Maryland state line with access to shopping, dining, and commuter routes, this Rolling Hills home offers the advantages of newer construction without starting from the ground up.

Greencastle

Listing courtesy of Turn Key Realty Group. Contact: (717) 775-7000

7 Beds ⋅ 5 Baths

Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

2700 Loyalty Ct, Winchester

Listing courtesy of Colony Realty. Contact:

2 Beds ⋅ 2 Baths

Instant equity! Recently appraised at $345,000! Location, location, location! Conveniently located right between Snow Hill & Salisbury but tucked back in the woods making you feel away from it all! Featuring 2 bedrooms and 2 full baths downstairs - with an office or potential 3rd bedroom upstairs - living room with high ceilings and natural light, eat in kitchen with cut out into the living room, and huge wrap around deck to enjoy your private lot! A concrete driveway leads to your detached 2 car garage for parking or plenty of storage! HVAC and roof have been replaced in the last 4 years among many other updates and improvements! Move right in and make this your own!

3841 Sirman Dr, Snow Hill

Listing courtesy of ERA Martin Associates. Contact: 4107491818

3 Beds ⋅ 1 Baths

Welcome to 134 Gerald Avenue, a beautifully renovated ranch home located in the Rolling Hills neighborhood of Cumru Township and the Governor Mifflin School District. Completely renovated in 2024, this home offers a fresh, updated interior and a comfortable layout designed for convenient everyday living. The main level features three private bedrooms, a bright and inviting living space, and a kitchen area with direct access to the rear deck, perfect for relaxing, entertaining, or enjoying the outdoors. Main-floor laundry is conveniently located within the bathroom, eliminating the need to carry laundry between levels. The finished lower level provides valuable additional living space and features a walkout design with sliding glass doors leading to the backyard. Whether used as a family room, recreation area, home office, gym, or entertainment space, the lower level offers plenty of flexibility. With extensive updates completed throughout the home, a finished walkout basement, outdoor living space, and a convenient location near shopping, dining, schools, and major roadways, and off street parking 134 Gerald Avenue is ready for its next owner to move in and enjoy.

134 Gerald Ave, Reading

Listing courtesy of Atlas Land and Homes. Contact: 4842220228

6 Beds ⋅ 5 Baths

Reduced! Beautifully maintained three-level residence offering an exceptional blend of space, comfort, and elegance. The main level features two generously sized bedrooms and two full bathrooms with a half bathroom. Sun-filled living spaces including a formal living room with fireplace, formal dining room, and a welcoming family room. The upgraded kitchen with a breakfast area opens seamlessly to a bright sunroom (accessed through two French doors), creating the perfect setting for everyday living and entertaining. The upper level boasts four spacious bedrooms and two full bathrooms, all enhanced by abundant natural light throughout the home. Basement is fully finished with family room and game room. Situated on the largest lot in the neighborhood, spanning 0.82 acres, this impressive property offers 6,306 square feet of refined living space. A three-car garage provides ample parking and storage. Ideally located in a desirable Hagerstown community, this home is designed to deliver both luxury and functionality in a truly exceptional setting. Go and show.

18903 Manchester Dr, Hagerstown

Listing courtesy of HomeSmart. Contact: 4109522641

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Jessica Sauls | Realtor | Memory Lane Property Group

With over two decades of experience and thousands of successful home sales, I provide calm, confident guidance through every stage of the real estate journey. Since 2003, I’ve helped buyers, sellers, investors, military families, and those navigating major life transitions make smart, well informed decisions. I do this with clarity, integrity, and strong advocacy. Real estate is more than a transaction, it’s deeply personal. I’m known for creating a steady, reassuring experience during what can often feel overwhelming. My clients value my ability to listen closely, communicate clearly, and protect their interests at every step. Whether negotiating complex terms, preparing a home for market, or navigating unexpected challenges, I lead with professionalism, transparency, and care. As a top performing Realtor in Maryland and Pennsylvania, I combine deep market expertise with a strategic, hands on approach. I help sellers maximize value through thoughtful preparation, including repairs and upgrades with payment deferred until closing. For buyers, I provide honest insight, strong negotiation, and a no-pressure approach. I want all of my Clients to move forward with confidence. Having successfully navigated multiple market cycles, I understand how to adapt strategies in changing conditions while keeping my clients’ goals front and center. Beyond real estate, I am deeply committed to my community, supporting scholarships, housing initiatives, and local education. That commitment to service carries into my work, showing up fully, advocating fiercely, and always doing what’s right for my Clients. If you’re looking for an experienced, steady professional who will treat your goals with care and deliver a strong, strategic outcome, I would be honored to work with you. It's my Mission to provide strategic, ethical, and compassionate real estate guidance that empowers people to build stability, wealth, and a life they love. We create calm, clear, and trustworthy experiences, and we strengthen our community through service, connection, and integrity. I believe in building futures, relationships, and legacies that last.

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Brian Sauls | Realtor | Memory Lane Property Group

Brian brings a thoughtful, detail-oriented approach to every real estate transaction. He helps clients understand the true condition and quality of a home beyond surface details, offering valuable insight during showings and throughout the decision-making process. Known for his calm demeanor, reliability, and strong attention to detail, Brian ensures clients feel comfortable, informed, and well supported from start to finish. He answers questions in real time, offers practical perspective, and helps buyers assess homes with confidence and clarity. Brian’s approach is grounded, professional, and service-oriented. His ability to provide meaningful guidance while keeping the process smooth and stress-free makes him a trusted advocate for his clients every step of the way.

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Christina Jones | Client Care | Memory Lane Property Group

Christina is the heart of our client experience and serves as our Director of Client Care. From the moment a client enters our world to well beyond the closing table, Christina ensures every detail is handled with care, clarity, and consistency. With a calm, organized, and compassionate approach, Christina manages communication, timelines, and behind-the-scenes coordination so our clients feel supported and informed at every step. She is often the friendly voice checking in, the steady hand keeping everything on track, and the person making sure nothing slips through the cracks. Christina is deeply committed to creating a smooth, low-stress experience for buyers and sellers alike. She understands that real estate transactions often come during significant life moments, and she brings patience, empathy, and professionalism to each interaction. Her focus on service, follow-through, and genuine care allows our team to deliver a thoughtful, high-level experience — one where clients feel heard, respected, and confident throughout the process.

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Payson Clausen Realtor

Payson Clausen | Realtor | Memory Lane Property Group

Payson Clausen brings together years of experience in real estate, media production, and marketing to support our team and elevate the client experience. With a strong background in both the real estate industry and creative media, Payson plays a key role in how properties, brands, and stories are presented. His expertise in video production, marketing strategy, and digital content helps ensure our listings and messaging are clear, compelling, and thoughtfully executed. Beyond his professional skill set, Payson is deeply committed to serving his community. He regularly volunteers his time working with local students and is actively involved in raising funds for SkillsUSA, supporting career and technical education programs that prepare young people for future success. Payson’s blend of industry knowledge, creative talent, and community involvement reflects our team’s values — using our work not just to serve clients, but to make a meaningful impact beyond the transaction. (function() { var rg = document.createElement('script'); rg.type = 'text/javascript'; rg.async = true; rg.src = 'https://widgets.realgeeks.com/static/js/search_widget_new.js?v=3'; var s = document.getElementsByTagName('script')[0]; s.parentNode.insertBefore(rg, s); })();

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