Rollingwood Homes for Sale

Rollingwood Homes for Sale

Welcome to Rollingwood, a charming and picturesque subdivision nestled in the heart of Chevy Chase, Maryland. This delightful community is known for its tree-lined streets, friendly neighbors, and a strong sense of belonging. With its prime location in Montgomery County, Rollingwood offers the perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, young professionals, and retirees alike.

Rollingwood boasts a diverse collection of homes for sale, each exuding unique character and charm. From classic mid-century ranch-style houses to modern architectural gems, there’s a home to suit every taste and lifestyle. Many properties feature spacious yards, perfect for outdoor gatherings and play, while others offer stunning views of the surrounding landscape. Inside, you'll find well-appointed living spaces with plenty of natural light, gourmet kitchens, and cozy fireplaces that create a warm and inviting atmosphere.

Residents of Rollingwood enjoy easy access to an array of local amenities, including parks, shops, and restaurants. The nearby Chevy Chase Village offers boutique shopping and dining experiences, while the bustling downtown area of Bethesda is just a short drive away, providing even more options for entertainment and leisure. For those who appreciate the great outdoors, the community is conveniently located near hiking trails and recreational parks.

With homes for sale in Rollingwood, you’re not just buying a property; you’re investing in a lifestyle filled with comfort, community, and convenience. Come and explore all that Rollingwood has to offer—your dream home awaits!

Newest Rollingwood Homes for Sale

3117 Brooklawn Ter, Chevy Chase
$1,250,000
5 Beds ⋅ 3 Baths
Originally designed as a classic ranch, this home has been thoughtfully transformed into a light-filled contemporary residence featuring quality craftsmanship and modern finishes throughout. Hardwood flooring on the main level and ceramic tile on the lower level complement the home's clean, contemporary design. The modern kitchen opens to spacious living and dining areas, where dramatic floor-to-ceiling windows overlook a partially landscaped, wooded yard backing to Rock Creek Park. An adjoining deck provides an inviting space for outdoor entertaining. The main level features a generous primary suite with a luxurious bath and three spacious closets with built-in drawers, along with two additional bedrooms and a full bath. An open staircase leads to the expansive walkout lower level, offering a large recreation room with floor-to-ceiling windows and direct patio access, two additional bedrooms, and a full bath. A wonderful combination of contemporary living, abundant natural light, and a serene parkland setting.

3117 Brooklawn Ter, Chevy Chase

Listing courtesy of Compass. Contact:

3207 Pickwick Ln, Chevy Chase
$1,895,000
6 Beds ⋅ 4 Baths
Timeless English Tudor Charm Meets Parisian-Inspired Elegance in Chevy Chase's Sought-After Rollingwood Community! Beautifully reimagined with a sophisticated Parisian flair, this stunning 6-bedroom, 3.5-bath English Tudor with a brick and stone façade seamlessly blends original architectural charm with thoughtfully curated modern finishes. A welcoming front porch with a beautiful cedar ceiling sets the tone for the charm and character that await inside. Step inside the welcoming foyer, where an original arched doorway leads into an elegant living room featuring a wood-burning fireplace, paneled walls, and a second graceful archway opening to the formal dining room, adorned with classic wainscoting. The gorgeous, newly renovated chef's kitchen is a true showstopper, featuring custom cabinetry, quartz countertops, all-new Jen Air appliances, and a center island that opens to the dining room, creating an ideal setting for both everyday living and entertaining. Just beyond the kitchen, a beautifully appointed butler's pantry offers additional custom cabinetry and convenient access to the backyard. A chic powder room with designer wallpaper and a versatile main-level bedroom, featuring dramatic, dark-toned paneled walls and perfectly suited for a home office, complete this level. An elegant staircase, showcasing the home's original architectural character, leads to the upper level, where you'll find four bedrooms and two beautifully renovated full baths. The inviting primary suite is also adorned with beautiful millwork, featuring dual closets, and a luxurious en-suite bath with a double vanity and beautifully tiled walk-in shower with a built-in niche. Three additional bedrooms and a stylishly renovated hall bath complete the upper level. The finished lower level offers even more space to relax and unwind, with a spacious family room centered around a second wood-burning fireplace, perfect for cozy evenings, movie nights, or entertaining. A sixth bedroom with an en-suite bath provides an ideal retreat for overnight guests or an au pair. A wine cellar, laundry room, and convenient walkout access to the backyard complete this level. Outside, the fully fenced backyard is a private oasis designed for entertaining and everyday enjoyment. A beautiful slate patio offers the perfect setting for outdoor dining and gatherings, while a charming stone walkway leads to a tucked-away "secret garden," complete with a second stone patio. The expansive grassy lawn provides plenty of room for pets, play, and relaxation. Additional highlights include beautifully curated custom lighting and statement chandeliers, crown molding, solid hardwood flooring throughout the main and upper levels, durable luxury vinyl plank flooring on the lower level, a brand-new architectural shingle roof, a new furnace and air conditioning compressor (2026), Nest thermostats, Ring cameras, a private driveway, and so much more. A truly special home where timeless Tudor character, Parisian-inspired sophistication, and modern comfort come together in one of Chevy Chase's most desirable neighborhoods.

3207 Pickwick Ln, Chevy Chase

Listing courtesy of Corcoran McEnearney. Contact:

3405 Leland St, Chevy Chase
$2,395,000
6 Beds ⋅ 5 Baths
Not often does the combination of traditional design with modern updates come together as they have at 3405 Leland Street, a beautifully renovated 6 bedroom, 4.5 bath home in the highly sought after Rollingwood neighborhood of Chevy Chase. Recently updated with a gourmet kitchen, renovated baths and numerous thoughtful design touches throughout, the home blends modern comfort with inviting, spacious living. The main level is ideal for both everyday living and entertaining, with the gourmet kitchen offering direct access to the expansive rear flagstone patio, a breakfast room, a formal dining room, and welcoming living and family rooms, each with a fireplace, and a half bath. Upstairs, four bedrooms include a generous primary suite with an ensuite full bath, large walk-in closet, dressing table and washer and dryer, plus a second bedroom with its own ensuite full bath. The additional two bedrooms share a hall bath. The third level offers flexible space for another bedroom, office or workout area with additional storage. The lower level includes exceptional flexibility with a two car garage, recreation room with fireplace, additional bedroom and full bath, laundry, and storage. Outside, the large wraparound patio creates an ideal setting for outdoor dining, entertaining, or a private retreat. With its thoughtful updates, generous living spaces, multiple fireplaces, and prime Rollingwood location near Rock Creek Park and downtown Bethesda, 3405 Leland Street offers the perfect combination of style, comfort, and convenience.

3405 Leland St, Chevy Chase

Listing courtesy of Washington Fine Properties. 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
$1,400,000
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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