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

$2,495,000
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: info@wfp.com

$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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