Rollingwood Homes for Sale

Rollingwood Homes for Sale

Welcome to Rollingwood, an enchanting subdivision nestled in the heart of Chevy Chase, Maryland. This picturesque community, located in Montgomery County, is renowned for its serene ambiance, lush greenery, and a strong sense of community. Rollingwood's charming tree-lined streets and beautifully manicured lawns create a welcoming atmosphere that feels like home the moment you arrive.

The architectural styles in Rollingwood are diverse, offering a delightful mix of classic and contemporary homes. From cozy bungalows to expansive single-family residences, each property exudes character and charm. With homes for sale in this sought-after neighborhood, prospective buyers will find a range of options that cater to various tastes and lifestyles. Many homes boast spacious interiors, modern amenities, and inviting outdoor spaces perfect for entertaining or enjoying quiet evenings under the stars.

Living in Rollingwood means embracing a lifestyle of convenience and tranquility. Residents enjoy easy access to nearby parks, walking trails, and recreational facilities, making it an ideal location for outdoor enthusiasts. The community's proximity to vibrant shopping districts, fine dining, and top-rated schools adds to its appeal, ensuring that everything you need is just a stone’s throw away.

Whether you’re a first-time homebuyer or looking to settle into a family-friendly neighborhood, Rollingwood offers an exceptional living experience. Explore the homes for sale in this delightful subdivision and discover the perfect place to create lasting memories. Embrace the charm of Rollingwood, where community spirit meets suburban bliss. Your dream home awaits!

Newest Rollingwood Homes for Sale

1909 Tadcaster Rd, Catonsville
$585,000
4 Beds ⋅ 3 Baths
Welcome to Rollingwood, one of Catonsville’s most sought-after communities! This beautifully updated home offers expansive living space, featuring four bedrooms, three full bathrooms, and flexible spaces designed to accommodate a variety of needs. Natural light fills the main living area through an impressive display of windows, highlighting the original hardwood floors and brick-surround gas fireplace. The adjoining dining room continues the hardwood flooring and opens through French doors to a screened porch, perfect for morning coffee, outdoor dining, or entertaining. The eat-in kitchen features stainless steel appliances, quartz countertops and timeless wood cabinetry. The upper level includes three spacious bedrooms, each with hardwood flooring and Hunter ceiling fans installed in 2025. The primary bedroom offers two closets and an ensuite private bathroom. Downstairs, the first lower level expands the home’s living space with a family or recreation room featuring all new LVP flooring, a laundry area, and direct access to the rear patio and yard. This level also includes a fourth bedroom with a separate side entrance and a full bathroom; both renovated in 2025. Whether you need a guest suite, home office, fitness room, playroom, or space for multigenerational living, the layout offers plenty of options. An additional lower level provides abundant storage and even more room to make your own. Additional storage space includes the attic, accessible via pull-down stairs. The outdoor spaces are equally inviting, featuring a screened in porch, paved patio, mature landscaping, perennial gardens, and a fully fenced yard. Notable 2024-2025 improvements include fresh interior paint, a new front porch and walkway, a new A-frame front porch with replacement of that portion of the roof, a new exterior sewer line, a 200-amp electrical panel and HVAC system. Located near Rollingwood Swim Club, Rollingwood Park, Five Oaks Pool, the Trolley Trail, and Patapsco Valley State Park, this home places recreation, trails, playgrounds, and community amenities within easy reach. Enjoy a convenient location between Catonsville and Old Ellicott City.

1909 Tadcaster Rd, Catonsville

Listing courtesy of EXP Realty, LLC. Contact:

7708 Tanner Robert Ct, Springfield
$1,250,000
4 Beds ⋅ 5 Baths
Welcome to 7708 Tanner Robert Ct, a stunning stone-front Colonial tucked away on desirable cut-del-sac in Springfield.Offering approximately 3,900+ square feet of beautifully finished living space, this spacious home combines classic elegance with thoughtful updates and exceptional functionality. The main level features beautiful updated flooring, a welcoming foyer, formal living and dining area, a private office, and a spacious family room designed for everyday living and entertaining. The Kitchen offers generous cabinet and counter space and opens to the main living areas for an inviting, connected floor plan. Upstairs, You'll find four spacious bedrooms, including a generous primary suite. Providing plenty of room for family and guest.The finished lower level adds tremendous versatility with a full bathroom and a stylish wet-bar Security cameras and audio system on the property does not convey . The existing carpet on bedrooms will be replaced .

7708 Tanner Robert Ct, Springfield

Listing courtesy of Vera's Realty Inc.. Contact:

7215 Rollingwood Dr, Chevy Chase
$1,550,000
5 Beds ⋅ 4 Baths
Timeless Colonial charm meets modern functionality in coveted Rollingwood! This classic Colonial in Chevy Chase’s sought-after Rollingwood neighborhood was thoughtfully renovated in 2016 to preserve its original 1940’s character amid a major refresh. Inside, a gracious foyer with hardwood floors opens to a living room with a wood-burning fireplace, detailed molding, and built-ins. A butler’s pantry connects to the dining room and an updated kitchen that features granite countertops, stainless steel appliances, and an island peninsula. Other standout features on the main level? A guest bedroom with an en-suite bath, and a sunlit family room with walls of windows. The upstairs offers three bedrooms and two full baths, including a spacious primary suite with dressing area, generous closet space, and an en-suite bath—while a finished third level provides flexible space for a bedroom or playroom. Additionally, the lower level of this home includes a rec room with a substantive brick fireplace, full bath, laundry, and ample storage. There are plenty of places to gather and commune here, and also plenty of space for . . . space! Beyond the dense integrity inside of this home, there is also the luxury of the exterior, which includes a gated backyard with brick patio and a private, landscaped setting. A slate roof, two-car garage, and driveway parking for four rounds out this residence. Comfortably situated near Rock Creek Park, Brookville Road shops and dining, this private and timeless abode offers easy access to Bethesda, DC, I-270, and I-495. Also listed for rent MLS #MDMC2226840.

7215 Rollingwood Dr, Chevy Chase

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

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