Rolling Knolls Real Estate

Rolling Knolls Real Estate

Welcome to Rolling Knolls, a picturesque subdivision nestled in the heart of Annapolis, Maryland, within the charming Anne Arundel County. This delightful community is renowned for its serene ambiance, lush green spaces, and a perfect blend of suburban tranquility and urban convenience.

Rolling Knolls offers a variety of beautifully designed homes that cater to diverse lifestyles, from cozy single-family residences to spacious townhomes. Each property is thoughtfully situated among tree-lined streets, creating an inviting atmosphere that encourages leisurely strolls and friendly neighborly interactions.

Residents of Rolling Knolls enjoy easy access to a wealth of amenities and recreational opportunities. The community is just a stone's throw away from the vibrant downtown Annapolis area, where you can explore a plethora of shops, restaurants, and cultural attractions. The historic charm of the city, combined with its waterfront views, makes it a perfect backdrop for outdoor enthusiasts and history buffs alike.

Families will appreciate the highly-rated schools in the area, ensuring that children receive a quality education. For those who enjoy outdoor activities, Rolling Knolls is conveniently located near parks and nature trails, providing ample opportunities for hiking, biking, and picnicking.

With its ideal location and strong sense of community, Rolling Knolls is more than just a place to live; it’s a lifestyle choice. Whether you’re a first-time homebuyer or looking to settle down, this enchanting subdivision offers a welcoming environment that you’ll be proud to call home. Discover the charm of Rolling Knolls today and experience the best of Annapolis living!

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:

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