Rollingwood Homes for Sale

Rollingwood Homes for Sale

Welcome to Rollingwood, a charming and tranquil subdivision nestled in the heart of Maryland. Known for its picturesque tree-lined streets and a strong sense of community, Rollingwood offers a perfect blend of suburban serenity and convenient access to urban amenities. This delightful neighborhood is ideally situated, providing residents with a peaceful retreat while still being just a stone's throw away from the vibrant culture and attractions of nearby cities.

Rollingwood is characterized by its diverse array of homes, each exuding unique charm and character. From cozy single-family residences to spacious contemporary designs, there is something to suit every taste and lifestyle. Many homes feature beautifully landscaped yards, inviting porches, and modern amenities that cater to today’s homeowners. Whether you’re a first-time buyer, a growing family, or looking to downsize, you’ll find a welcoming community that meets your needs.

Currently, there are a variety of homes for sale in Rollingwood, offering an exciting opportunity for prospective buyers. With competitive pricing and a range of options, now is the perfect time to explore what this enchanting subdivision has to offer. Residents here enjoy access to excellent schools, local parks, and recreational facilities, making it a great place for families and individuals alike.

Discover the charm of Rollingwood and find your dream home in this picturesque subdivision. Embrace the lifestyle you’ve always wanted, where community, comfort, and convenience come together beautifully. Your ideal home awaits in Rollingwood, Maryland!

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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Jessica Sauls | Realtor | Memory Lane Property Group

With over two decades of experience and thousands of successful home sales, I provide calm, confident guidance through every stage of the real estate journey. Since 2003, I’ve helped buyers, sellers, investors, military families, and those navigating major life transitions make smart, well informed decisions. I do this with clarity, integrity, and strong advocacy. Real estate is more than a transaction, it’s deeply personal. I’m known for creating a steady, reassuring experience during what can often feel overwhelming. My clients value my ability to listen closely, communicate clearly, and protect their interests at every step. Whether negotiating complex terms, preparing a home for market, or navigating unexpected challenges, I lead with professionalism, transparency, and care. As a top performing Realtor in Maryland and Pennsylvania, I combine deep market expertise with a strategic, hands on approach. I help sellers maximize value through thoughtful preparation, including repairs and upgrades with payment deferred until closing. For buyers, I provide honest insight, strong negotiation, and a no-pressure approach. I want all of my Clients to move forward with confidence. Having successfully navigated multiple market cycles, I understand how to adapt strategies in changing conditions while keeping my clients’ goals front and center. Beyond real estate, I am deeply committed to my community, supporting scholarships, housing initiatives, and local education. That commitment to service carries into my work, showing up fully, advocating fiercely, and always doing what’s right for my Clients. If you’re looking for an experienced, steady professional who will treat your goals with care and deliver a strong, strategic outcome, I would be honored to work with you. It's my Mission to provide strategic, ethical, and compassionate real estate guidance that empowers people to build stability, wealth, and a life they love. We create calm, clear, and trustworthy experiences, and we strengthen our community through service, connection, and integrity. I believe in building futures, relationships, and legacies that last.

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Brian Sauls | Realtor | Memory Lane Property Group

Brian brings a thoughtful, detail-oriented approach to every real estate transaction. He helps clients understand the true condition and quality of a home beyond surface details, offering valuable insight during showings and throughout the decision-making process. Known for his calm demeanor, reliability, and strong attention to detail, Brian ensures clients feel comfortable, informed, and well supported from start to finish. He answers questions in real time, offers practical perspective, and helps buyers assess homes with confidence and clarity. Brian’s approach is grounded, professional, and service-oriented. His ability to provide meaningful guidance while keeping the process smooth and stress-free makes him a trusted advocate for his clients every step of the way.

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Christina Jones | Client Care | Memory Lane Property Group

Christina is the heart of our client experience and serves as our Director of Client Care. From the moment a client enters our world to well beyond the closing table, Christina ensures every detail is handled with care, clarity, and consistency. With a calm, organized, and compassionate approach, Christina manages communication, timelines, and behind-the-scenes coordination so our clients feel supported and informed at every step. She is often the friendly voice checking in, the steady hand keeping everything on track, and the person making sure nothing slips through the cracks. Christina is deeply committed to creating a smooth, low-stress experience for buyers and sellers alike. She understands that real estate transactions often come during significant life moments, and she brings patience, empathy, and professionalism to each interaction. Her focus on service, follow-through, and genuine care allows our team to deliver a thoughtful, high-level experience — one where clients feel heard, respected, and confident throughout the process.

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Payson Clausen Realtor

Payson Clausen | Realtor | Memory Lane Property Group

Payson Clausen brings together years of experience in real estate, media production, and marketing to support our team and elevate the client experience. With a strong background in both the real estate industry and creative media, Payson plays a key role in how properties, brands, and stories are presented. His expertise in video production, marketing strategy, and digital content helps ensure our listings and messaging are clear, compelling, and thoughtfully executed. Beyond his professional skill set, Payson is deeply committed to serving his community. He regularly volunteers his time working with local students and is actively involved in raising funds for SkillsUSA, supporting career and technical education programs that prepare young people for future success. Payson’s blend of industry knowledge, creative talent, and community involvement reflects our team’s values — using our work not just to serve clients, but to make a meaningful impact beyond the transaction. (function() { var rg = document.createElement('script'); rg.type = 'text/javascript'; rg.async = true; rg.src = 'https://widgets.realgeeks.com/static/js/search_widget_new.js?v=3'; var s = document.getElementsByTagName('script')[0]; s.parentNode.insertBefore(rg, s); })();

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