Rollingwood Homes for Sale

Rollingwood Homes for Sale

Welcome to Rollingwood, a picturesque subdivision nestled in the heart of Chevy Chase, Maryland. Known for its serene tree-lined streets and vibrant community spirit, Rollingwood is a hidden gem in Montgomery County that offers a perfect blend of suburban tranquility and urban convenience.

As you explore this charming neighborhood, you’ll find a delightful array of homes for sale, each exuding unique character and timeless appeal. From mid-century modern masterpieces to classic colonial styles, Rollingwood's real estate options cater to diverse tastes and lifestyles. Many of these residences boast spacious yards, ideal for family gatherings or quiet evenings under the stars, while some feature updated interiors that blend modern amenities with original charm.

Living in Rollingwood means being part of a close-knit community that values connection and engagement. Residents often gather for seasonal events, and the local parks provide ample opportunities for outdoor activities, making it easy to enjoy nature right at your doorstep. Additionally, the subdivision is conveniently located near top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

For those seeking a peaceful yet vibrant lifestyle, Rollingwood offers the perfect setting to call home. With homes for sale that reflect the warmth and charm of this beautiful neighborhood, now is the ideal time to discover your dream home in Rollingwood. Embrace the opportunity to join this welcoming community and experience the best of Chevy Chase living!

Newest Rollingwood Homes for Sale

4 Beds ⋅ 3 Baths

1909 Tadcaster Rd, Catonsville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

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

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:

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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Nathan Barshinger

Nathan Barshinger | Top 0.5% Listing Agent NationwideA Higher Standard in Real Estate.Since 2020, Nathan has invested over 10,000 hours mastering real estate marketing and positioning. Frustrated by the lack of true professionalism in the industry, he built a business around one promise: creative marketing, real client service, and results that speak for themselves. This commitment has earned him steady referrals and the trust of clients and peers alike.Proven Results. National Recognition.Nathan’s performance puts him among the very best in the industry:eXp ICON Award in 2023, 2024, and 2025Top 30 Under 30 Nationwide in 2024 & 2025Ranked in the Top 0.5% of Listing Agents NationwideFor perspective: the average agent sells 4–6 homes per year. In 2024 alone, Nathan closed 82 transactions spanning residential, commercial, and land and is on pace to break 100 transactions in 2025.Grounded by Faith. Driven by Growth.Outside of real estate, Nathan and his wife Kate serve actively in their church, a foundation that shapes his values and leadership. When he’s not working, you’ll find him cruising on his motorcycle, hitting the gym, learning new things, spending time with family and friends, or with his Golden Retriever, Willow.Building a Team. Elevating an Industry.As a Top Agent, Nathan is building a team designed to help property owners maximize equity. His mission is clear:Provide real options, including cash offersEnsure clients achieve their goalsDeliver an experience unmatched in today’s marketFor Nathan, this is only the beginning.

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