Cherrywood Real Estate

Cherrywood Real Estate

Welcome to Cherrywood, a charming subdivision nestled in the heart of Olney, Maryland, within the picturesque Montgomery County. This delightful community offers a perfect blend of suburban tranquility and modern conveniences, making it an ideal choice for families, professionals, and retirees alike.

Cherrywood is renowned for its beautifully landscaped streets, where tree-lined avenues and well-maintained homes create a welcoming atmosphere. The neighborhood features a variety of architectural styles, ensuring that there’s something for everyone, from cozy single-family homes to spacious townhouses. With a strong sense of community, residents often gather for local events, fostering lifelong friendships and connections.

Nature enthusiasts will appreciate Cherrywood’s proximity to lush parks and recreational areas. The nearby Olney Manor Park offers miles of walking trails, sports fields, and picnic spots, perfect for family outings or a leisurely stroll. Additionally, the community is conveniently located near the scenic Patuxent River, providing ample opportunities for outdoor adventures.

For families, Cherrywood is served by highly-rated schools within the Montgomery County Public School system, ensuring that children receive a top-notch education. The area also boasts a variety of shopping, dining, and entertainment options, from quaint local boutiques to popular restaurants, all just a short drive away.

With its prime location, friendly atmosphere, and abundant amenities, Cherrywood is more than just a neighborhood; it’s a place to call home. Discover the charm of Cherrywood and experience the vibrant lifestyle that awaits you in Olney, Maryland!

Newest Listings in Cherrywood

3 Beds ⋅ 2 Baths

End-Unit Townhouse with a Large Fenced Yard and BRAND NEW ROOF! Welcome to 402 Winding Way! This spacious 1,796-sqare-foot, 2-story townhouse offers 3 bedrooms, 1.5 baths, and a desirable corner-lot location with a large fenced-in yard. The main level features newer luxury vinyl flooring throughout, a generously sized kitchen with plenty of cabinetry and shelving for storage, a breakfast bar complete with stools, and a convenient pantry. Cozy family room with brick fireplace. A laundry room with utility sink adds functionality and extra storage and leads into the garage. Upstairs, the spacious primary bedroom features a built-in vanity and walk-in closet along with its own sink and direct access to the full hall bath. Two additional bedrooms offer generous closet space. Step outside to enjoy the large fenced-in yard—perfect for outdoor entertaining, relaxing, or play. The shed with electric provides additional storage and workspace options. Seller has maintained the property with care and is selling it in as-is condition. Any inspections conducted by the buyer are for the buyer's informational purposes only, and seller will make no repairs. Seller will provide the Certificate of Occupancy. Conveniently located near shopping, dining, and major roadways, this home offers comfort, space, and convenience. Don't miss the opportunity to make 402 Winding Way your new home!

402 Winding Way, Clementon

Listing courtesy of HomeSmart First Advantage Realty. Contact: 8566663000

4 Beds ⋅ 4 Baths

Welcome to this beautiful 4-bedroom, 3.5-bathroom home offering the perfect blend of comfort, functionality, and inviting living spaces. From the charming front porch and spacious 2-car garage to the beautifully landscaped backyard, this home makes a wonderful first impression and continues to impress throughout. The main level features a welcoming foyer, formal living room, and formal dining room, along with an open-concept kitchen with a breakfast area and spacious family room centered around a cozy fireplace, creating the perfect space for both everyday living and entertaining. A convenient half bath completes the main level and is ideal for guests. Upstairs, the expansive primary suite offers a peaceful retreat with a private en-suite bathroom featuring a soaking tub, double vanity, and separate shower. Three additional generously sized bedrooms share a full bathroom, while the conveniently located upper-level laundry makes everyday living a breeze. The recently renovated lower level is truly a standout feature, offering a fantastic in-law or guest suite complete with a full mini kitchen, full bathroom, and private side entrance. Whether used for extended family, overnight guests, a home office, or additional living space, the possibilities are endless. Outside, enjoy your own private oasis with a beautifully landscaped backyard and spacious deck overlooking the lush surroundings, providing the perfect setting for morning coffee, summer gatherings, or relaxing evenings at home. With its versatile floor plan, inviting outdoor spaces, recently renovated lower level, and thoughtful features throughout, this is a true gem you will not want to miss!

4220 Cherry Valley Dr, Olney

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

5 Beds ⋅ 4 Baths

This classic five-bedroom, three full and one-half bath Colonial features tasteful interior updates along with exceptional outdoor living space. The main level showcases fresh paint, gleaming hardwood floors, crown molding, family room with wood-burning fireplace, a dedicated home office with built-in shelving, a stylish powder room with quartz countertop, and a convenient main-level laundry room with garage access. The renovated kitchen features cherry cabinetry, granite countertops, a center island, and new stainless steel appliances. Upstairs, the primary suite boasts cathedral ceilings in the private sitting room and an updated en-suite bath complete with new LVP flooring, a double vanity, a soaking tub, and a separate shower with new subway ceramic tiles. Three additional bedrooms with new carpet and fresh paint, and a split-hall bath with dual vanities round out the upper level. The fully finished walk-out lower level offers incredible flexibility, featuring a large rec room, a second fireplace in the TV room, a fifth bedroom/hobby room, a full bath, and two separate exits to the patio. Outdoor living is easy in the fenced backyard with patio, deck and hot tub, the covered front porch and the newly sealed driveway with four-car parking. Ideally situated close to Georgia Avenue, Route 108, and the ICC, this home offers quick access to top-rated schools, recreation, dining, and everyday shopping.

16904 Continental Ct, Olney

Listing courtesy of Samson Properties. Contact:

4 Beds ⋅ 3 Baths

HUGE PRICE REDUCTION!!! Beautifully updated brick-front colonial just steps from Cherry Valley Park and Cashell Elementary! This beautifully maintained 4-bedroom, 2 full and 2 half-bath home offers the perfect combination of space, comfort, and location. Inside, you'll find hardwood floors throughout much of the home, fresh interior and exterior paint, and a spacious floor plan designed for everyday living and entertaining. The sunken family room features a cozy wood-burning stove, while the expanded owner's suite includes a private sitting room or home office and two walk-in closets. The finished lower level provides additional living space, a convenient half bath, and plenty of storage. Outside, enjoy a private, fenced backyard complete with mature landscaping, an oversized storage shed, and plenty of room to relax or entertain. Additional highlights include a two-car garage, a newer 30-year architectural shingle roof, and numerous updates throughout. Ideally located just minutes from shopping, restaurants, commuter routes, and all that Olney has to offer. Professional photos coming soon��this is one you won't want to miss!

17105 Macduff Ave, Olney

Listing courtesy of RE/MAX Realty Services. Contact:

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Kathleen McMahan

For Kathleen McMahan, real estate has always been about more than buying and selling homes. It’s about people, relationships, and helping clients feel confident during some of the biggest transitions of their lives. With more than a decade of experience in Maryland and Washington, D.C. real estate, Kathleen has built her business around a simple philosophy: stay positive, work hard, communicate honestly, and treat every client’s move as if it were her own. Positivity has long been Kathleen’s “north star,” both personally and professionally. When her oldest son spent time in the NICU, she focused on learning everything she could from his nurses so she would feel prepared when it was finally time to bring him home. That experience reinforced something she carries into her work today: even during stressful and uncertain moments, knowledge, preparation, and the right perspective can make all the difference. That mindset has helped Kathleen build a successful real estate career based largely on relationships, referrals, and clients who return to her as their lives and real estate needs evolve. Now, as the agent behind McMahan Homes at Real Broker, she brings the experience of more than a decade in the industry together with the personal attention and flexibility of an independent real estate business. Originally from New Jersey, Kathleen came to Maryland to attend Salisbury University. Her studies in sociology and marketing helped spark a lasting curiosity about people—what motivates them, what matters to them, and what makes a place truly feel like home. Today, that curiosity is one of her greatest strengths as an agent. Kathleen takes the time to understand not just what her clients are looking for on paper, but what they want their lives to look like. Whether she’s preparing a home for the market, negotiating on behalf of a seller, helping a buyer find the right community, or simply answering the questions that come up along the way, her goal is to make the process feel informed, personal, and manageable. Kathleen lives in Maryland with her husband and two sons. When she isn’t working, you’ll most likely find her spending time with her family, dreaming about her next trip to the Florida Keys, or planning her next home project.

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