Life at Rollingwood in Chevy Chase, Maryland

Our latest move-in ready home at 3301 Winnett Road, is located in Chevy Chase’s Rollingwood. A well established community developed in the 1930s, consisting of over 800 homes in a quiet wooded setting, in closes proximity to countless options for recreation, shopping and fine dining.

A map outlining the boundaries of the Rollingwood community in Chevy Chase, backing to Rock Creek Park.

A Woodland Buffer 

Rollingwood is a partially no-thru community, backing to to Rock Creek Park, creating a buffer, reducing neighborhood thru-traffic and ambient noise, making it much quieter than other Chevy Chase neighborhoods with closer proximity to major streets.

Residents enjoy direct access to the park, serving as a shared 1,700+ acre community recreation area, with extensive trails for a morning run or a weekend family bicycle adventure.

Download Trail Maps from MontgomeryParks.org ->

A logo with a green circle and green tree reads Chey Chase, Rollingwood, est 1933

Rollingwood Citizens Association (RCA)

The Rollingwood Citizens Association is not an HOA, rather it is a volunteer-led non-profit advocating for the community, working with local leaders on issues such as transportation, safety, parks and tree preservation. The RCA also works to foster a general community spirit, hosting block parties, picnics and holiday events.

Visit the Rollingwood Citizens Association Website ->

A female rider in a black tailcoat, white breeches, and helmet rides a bay horse in a dressage arena with a sand surface.

Meadowbrook Stables

Located a short walk from Rollingwood, Meadowbrook Stables is a full service equestrian facility operated by a nonprofit organization with a public-private partnership with Montgomery Parks. The stables offer lessons for all ages and skill levels, summer camp, boarding and horse shows.

Visit the Meadowbrook Stables website ->

An exterior view of the historic Avalon Theater in Chevy Chase, Maryland, featuring a brick facade, architectural detailing, and a vertical neon sign against a blue sky.

Close Proximity to Washington, DC

Rollingwood offers a quiet, wooded suburban settings in close proximity to Washington, DC. With the boutique shops, restaurants and historic non-profit Avalon Theater at Chevy Chase Circle a five minute drive away.  Also nearby, two top private DC schools, Sidwell Friends (under 4 miles) and Georgetown Day School (under 3 miles). 

 

A woman with long straight hair walks away from the camera, down a brick street lined with stores. She wears a beige blazer over blue jeans and brown boots, and she is holding three shopping bags from Bethesda Row

A Wealth of Shopping & Fine Dining

Rollingwood is located within a few miles of several popular shopping centers in downtown Bethesda, Chevy Chase and Friendship Heights – including luxury brands, major chains, fine dining and high-end grocery stores.

A wide-angle landscape photo of the Meadowbrook Local Park building and pavilion under a cloudy blue sky, viewed from across an empty parking lot.

Meadowbrook Local Park

Rollingwood features an expansive public park, with playgrounds, baseball fields, basketball courts, soccer fields and picnic shelters. The park also includes an Activity Building, available by reservation, the air-conditioned space has a kitchen and a max capacity of 150 people.

Learn more at MontgomeryParks.org ->

A modern two-story home with white board-and-batten siding, light stone accents, and black-trimmed windows.

Move-In Ready at Rollingwood

Learn more about our move-in ready home in Rollingwood at 3301 Winnett Road. Schedule a tour and explore the architectural details and curated features that showcase the signature craftsmanship of Classic Homes of Maryland.

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