Rolling Knolls Real Estate

Rolling Knolls Real Estate

Welcome to Rolling Knolls, a picturesque subdivision nestled in the heart of Maryland that perfectly blends suburban tranquility with modern conveniences. This charming community is characterized by its lush landscapes, tree-lined streets, and a warm, welcoming atmosphere that makes it an ideal place for families, young professionals, and retirees alike.

Rolling Knolls boasts a variety of beautifully designed homes, ranging from cozy single-family residences to spacious townhouses, ensuring there’s something to suit every lifestyle and budget. Each property is thoughtfully situated on generous lots, offering residents ample outdoor space to enjoy the natural beauty that surrounds them. The neighborhood is known for its well-maintained parks and recreational areas, providing plenty of opportunities for outdoor activities, picnics, and community gatherings.

Convenience is key in Rolling Knolls, with easy access to major highways, making commutes to nearby cities a breeze. Residents can enjoy a plethora of shopping, dining, and entertainment options just a short drive away, including local boutiques, popular restaurants, and vibrant cultural attractions. Moreover, the area is served by highly-rated schools, making it a perfect choice for families focused on education and community involvement.

With its blend of serenity and accessibility, Rolling Knolls is more than just a place to live; it’s a community where neighbors become friends, and memories are made. Discover the charm of Rolling Knolls today, and find your dream home in this delightful Maryland subdivision!

Newest Listings in Rolling Knolls

$950,000
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
$989,000
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:

$600,000
3 Beds ⋅ 2 Baths
Welcome home to 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. 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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