Rolling Knolls Real Estate

Rolling Knolls Real Estate

Welcome to Rolling Knolls, a hidden gem nestled in the heart of Annapolis, Maryland. This charming subdivision offers a perfect blend of suburban tranquility and vibrant city life, making it an ideal choice for families, professionals, and retirees alike. With its picturesque tree-lined streets and beautifully manicured lawns, Rolling Knolls exudes a warm and inviting atmosphere that feels like home from the moment you arrive.

One of the standout features of Rolling Knolls is its prime location within Anne Arundel County. Residents enjoy easy access to the historic charm of downtown Annapolis, where you can explore boutique shops, dine at exquisite restaurants, and soak in the rich maritime heritage of the area. For those who appreciate the outdoors, the nearby parks and waterfronts provide ample opportunities for hiking, boating, and enjoying the stunning Chesapeake Bay views.

The community of Rolling Knolls is characterized by its friendly neighbors and a strong sense of community spirit. Families benefit from the highly-rated schools within the Anne Arundel County Public School System, ensuring that children receive a top-notch education. Moreover, the subdivision hosts regular community events, fostering connections among residents and creating a vibrant social calendar.

Whether you’re looking for a cozy single-family home or a spacious townhouse, Rolling Knolls offers a variety of housing options to suit diverse lifestyles. With its perfect blend of convenience, community, and charm, Rolling Knolls is not just a place to live; it’s a place to thrive. Discover your dream home in this enchanting Annapolis neighborhood today!

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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