Rollingwood Homes for Sale

Rollingwood Homes for Sale

Welcome to Rollingwood, a picturesque subdivision nestled in the heart of the United States, where tranquility meets modern living. Known for its lush landscapes and friendly community atmosphere, Rollingwood offers an idyllic escape from the hustle and bustle of urban life while still being conveniently close to all the amenities you desire.

As you explore this charming neighborhood, you’ll discover a variety of homes for sale that cater to diverse tastes and lifestyles. From cozy single-family residences to spacious modern builds, each property is designed with comfort and elegance in mind. Many homes feature beautifully landscaped yards, inviting porches, and open-concept living spaces that are perfect for both relaxation and entertaining.

Rollingwood is not just about beautiful homes; it’s also about community. Residents enjoy access to various parks, walking trails, and recreational facilities, making it easy to embrace an active lifestyle. Families will appreciate the top-rated schools in the area, ensuring that children receive a quality education close to home.

With a strong sense of community spirit, Rollingwood hosts seasonal events and gatherings that foster connections among neighbors. Whether you’re sipping coffee at a local café or enjoying a sunny afternoon at the park, you’ll find that Rollingwood offers a warm welcome to all.

If you’re searching for a place to call home that combines charm, convenience, and community, look no further than Rollingwood. Explore our current listings of homes for sale and discover the perfect property to start your next chapter in this enchanting subdivision!

Newest Rollingwood Homes for Sale

3101 Brooklawn Ter, Chevy Chase
$1,190,000
4 Beds ⋅ 4 Baths
This stunning 4-bedroom, 3.5-bathroom ranch-style home in the desirable Rollingwood subdivision offers an excellent investment opportunity with a spacious 3,464 sq. ft. layout. Built in 1960, this brick-constructed residence features a partially finished basement, enhancing potential rental income or additional living space. Interior highlights include an open floor plan with hardwood and stone flooring, a family room off the kitchen, and a dining area perfect for entertaining. The kitchen is equipped with modern appliances, including a built-in range, dishwasher, and extra refrigerator/freezer, ensuring convenience for tenants or future buyers. Recessed lighting, skylights, and walk-in closets add to the home's appeal. The exterior boasts a generous 0.4-acre corner lot that backs onto parkland, providing serene views of trees and greenbelt. Enjoy outdoor living with a personal pool, screened porch, and BBQ grill, ideal for attracting renters or enhancing resale value. An attached 2-car garage adds practicality and security. Located adjacent to a national park, this property offers a unique blend of tranquility and accessibility, making it attractive for long-term investment. The combination of desirable features, location, and potential for appreciation positions this home as a prime opportunity for savvy investors looking to capitalize on the growing real estate market. This property is being sold in AS-IS condition. No repairs will be made to home prior to settlement.

3101 Brooklawn Ter, Chevy Chase

Listing courtesy of Long & Foster Real Estate, Inc.. 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 seamlessly blends original architectural charm with thoughtfully curated modern finishes. 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 stunning 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, 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:

1909 Tadcaster Rd, Catonsville
$565,000
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:

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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