Rolling Knolls Real Estate

Rolling Knolls Real Estate

Welcome to Rolling Knolls, an enchanting subdivision nestled in the heart of Maryland. This picturesque community offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, young professionals, and retirees alike.

Rolling Knolls is characterized by its beautifully landscaped streets, lined with charming homes that exude warmth and character. Each property reflects a commitment to quality and craftsmanship, ensuring that residents enjoy both comfort and style. The neighborhood is designed to foster a sense of community, with friendly neighbors and a welcoming atmosphere that makes everyone feel at home.

Nature lovers will appreciate the abundance of green spaces and parks nearby, providing ample opportunities for outdoor activities such as hiking, biking, and picnicking. The scenic beauty of the area is complemented by well-maintained walking trails and playgrounds, making it a perfect setting for families to create lasting memories.

Conveniently located just a short drive from major highways, Rolling Knolls offers easy access to nearby shopping, dining, and entertainment options. Whether you're looking to explore the vibrant local scene or enjoy a quiet evening at home, this subdivision has it all. Additionally, top-rated schools and essential amenities are within reach, ensuring that residents have everything they need for a fulfilling lifestyle.

Discover the charm of Rolling Knolls, where community spirit meets the beauty of nature. Come and experience the joys of suburban living in this delightful Maryland gem!

Newest Listings in Rolling Knolls

5 Beds ⋅ 4 Baths

Newly and beautifully built in 2026, this stone-accented detached Calvert Model by Dorsey Family Homes offers 3,081 finished square feet and is ideally positioned on a quiet cul-de-sac in desirable Rolling Knolls. Offering a sleek, contemporary design and a bright, airy atmosphere, the home provides a sophisticated foundation for any aesthetic. Abundant natural light complements 9-foot ceilings, a refined mix of hardwood flooring and carpet, recessed lighting, crown molding, wainscoting, and spacious open living areas throughout. // Step inside the impressive two-story foyer, where doors open to a private library or home office. Across the foyer, the elegant formal dining room is illuminated by a statement chandelier. Ahead, the heart of the home unfolds into a spacious open-concept great room, featuring a comfortable family room with a gas fireplace and mantel, a cozy breakfast area with sliding glass doors ready for future outdoor living additions, and the beautifully appointed kitchen. // The gourmet eat-in kitchen is designed for both everyday living and effortless entertaining, featuring a generous center island with breakfast bar seating, upgraded countertops, crisp white cabinetry, stainless steel appliances, and a spacious walk-in pantry. Just off the kitchen, find a powder room and a convenient drop zone providing organized storage near the garage entry. Also located on the main level is a private bedroom or versatile bonus room with a walk-in closet, ideal for guests or multigenerational living arrangements. // Upstairs, four generously sized bedroom suites provide comfortable private retreats. The expansive owner’s suite features an elegant tray ceiling, dual walk-in closets—including an exceptionally large one—and a luxurious ensuite bathroom with a Roman soaking tub, dual-sink vanity, walk-in shower, and private water closet. Two secondary bedrooms share a thoughtfully designed dual-entry full bathroom with dual sinks, while the fourth enjoys its own private ensuite bath. All three secondary bedrooms feature walk-in closets, providing abundant storage. A centrally located laundry room completes the upper level. The walk-out lower-level basement offers a versatile blank canvas, ready to be customized to suit your lifestyle. // Outside, the spacious backyard offers a peaceful, tree-lined backdrop and plenty of room to create your ideal outdoor retreat. The attached two-car garage includes a rough-in for an electric vehicle charging station, while the asphalt driveway provides additional parking.

2175 Glencrest Cir, Annapolis

Listing courtesy of Keller Williams Lucido Agency. Contact: (410) 465-6900

4 Beds ⋅ 4 Baths

Welcome to this beautifully maintained and thoughtfully updated residence located in the desirable Derwood area. Situated on a quiet cul-de-sac, this home offers a functional layout, abundant natural light, and well-proportioned living spaces designed for both everyday living and entertaining. The main level features a spacious living area, a formal dining space, and an updated kitchen equipped with modern appliances, ample cabinetry, and generous counter space. The adjoining family room provides a comfortable setting with views of the surrounding landscape. Upstairs, the property offers multiple bedrooms including a well-appointed primary suite with an en-suite bath and ample closet space. Additional bedrooms are appropriately sized and supported by updated bathrooms. The lower level provides additional flexible living space suitable for recreation, home office use, or guest accommodations. Exterior features include a private backyard, mature landscaping with professional landscape lighting, and outdoor space ideal for relaxation or entertaining. A standout feature of this property is the large detached garage, complete with an unfinished second-story loft—offering exceptional potential for a workshop, studio, home office, or future finished living space. The home is also equipped with a whole-house generator system, providing added peace of mind and uninterrupted comfort year-round. Additional highlights include off-street parking and an attached garage. Conveniently located near major commuter routes, shopping, dining, and local amenities, this home offers both comfort and accessibility.

5820 Winegrove Ct, Derwood

Listing courtesy of Miller Realty Services, LLC. Contact:

3 Beds ⋅ 2 Baths

New opportunity to own this beautifully renovated split-level in a sought-after community! Featuring a bright, open floor plan with quality finishes throughout, this move-in ready home offers wood floors, an updated kitchen, and fully renovated baths. The three-bedroom layout provides comfortable living spaces designed for today's lifestyle. Nestled on a private, wooded 0.40-acre lot backing to Annapolis Waterworks Park, you'll enjoy peaceful views and direct access to nature right in your backyard. No HOA. An oversized one-car garage offers ample room for a workshop, hobbies, and extra storage, while the encapsulated crawl space provides even more storage options. New septic tank. New roof and heat pump installed in 2024. Residents appreciate the community elementary school and voluntary association. The location is truly exceptional—just minutes from downtown Annapolis, the medical center, shopping, restaurants, and local pubs. Commuters will love the quick access to major routes, making travel throughout the region a breeze. This turnkey home combines charm, convenience, and value in one fantastic package. Don't miss your chance to make it yours!

622 Wayward Dr, Annapolis

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

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Kathleen McMahan

For Kathleen McMahan, real estate has always been about more than buying and selling homes. It’s about people, relationships, and helping clients feel confident during some of the biggest transitions of their lives. With more than a decade of experience in Maryland and Washington, D.C. real estate, Kathleen has built her business around a simple philosophy: stay positive, work hard, communicate honestly, and treat every client’s move as if it were her own. Positivity has long been Kathleen’s “north star,” both personally and professionally. When her oldest son spent time in the NICU, she focused on learning everything she could from his nurses so she would feel prepared when it was finally time to bring him home. That experience reinforced something she carries into her work today: even during stressful and uncertain moments, knowledge, preparation, and the right perspective can make all the difference. That mindset has helped Kathleen build a successful real estate career based largely on relationships, referrals, and clients who return to her as their lives and real estate needs evolve. Now, as the agent behind McMahan Homes at Real Broker, she brings the experience of more than a decade in the industry together with the personal attention and flexibility of an independent real estate business. Originally from New Jersey, Kathleen came to Maryland to attend Salisbury University. Her studies in sociology and marketing helped spark a lasting curiosity about people—what motivates them, what matters to them, and what makes a place truly feel like home. Today, that curiosity is one of her greatest strengths as an agent. Kathleen takes the time to understand not just what her clients are looking for on paper, but what they want their lives to look like. Whether she’s preparing a home for the market, negotiating on behalf of a seller, helping a buyer find the right community, or simply answering the questions that come up along the way, her goal is to make the process feel informed, personal, and manageable. Kathleen lives in Maryland with her husband and two sons. When she isn’t working, you’ll most likely find her spending time with her family, dreaming about her next trip to the Florida Keys, or planning her next home project.

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