Oakdale Crossing Real Estate

Oakdale Crossing Real Estate

Welcome to Oakdale Crossing, an enchanting subdivision nestled in the heart of Winchester, Virginia, within the picturesque Frederick County. This vibrant community is designed for those who appreciate both tranquility and convenience, providing a perfect blend of suburban charm and modern amenities.

Oakdale Crossing is renowned for its beautifully landscaped streets, offering a serene environment that invites leisurely strolls and friendly neighborhood gatherings. The homes here are thoughtfully crafted, showcasing a variety of architectural styles that cater to diverse tastes. From cozy single-family homes to spacious townhouses, each residence reflects quality and comfort, making it an ideal place to call home.

One of the standout features of Oakdale Crossing is its prime location. Residents enjoy easy access to a plethora of shopping, dining, and recreational options. Just a short drive away, you’ll find the historic downtown Winchester, brimming with unique boutiques, delightful cafes, and rich cultural experiences. For outdoor enthusiasts, the nearby parks and nature trails provide ample opportunities for hiking, biking, and enjoying the beautiful Virginia landscape.

Families will appreciate the top-rated schools in the area, ensuring that children receive a quality education within a supportive community. With friendly neighbors and a strong sense of belonging, Oakdale Crossing is more than just a place to live; it’s a place to thrive.

Whether you’re looking to settle down or invest in a promising future, Oakdale Crossing offers a welcoming atmosphere and a lifestyle that truly feels like home. Come discover the charm and warmth of this delightful subdivision today!

Newest Listings in Oakdale Crossing

5 Beds ⋅ 4 Baths

Your Next Chapter Starts Here! Space, style, flexibility, and a backyard made for entertaining — all tucked away on a quiet cul-de-sac in desirable Oakdale Crossing. This impressive 5-bedroom, 4-bathroom, three-level Colonial, with new roof (2026), delivers the kind of versatile space today’s buyers are looking for, with room to work from home, host friends, grow your household, or create the ultimate hangout zone. Start with the front wraparound porch, the perfect spot for morning coffee or winding down at the end of the day. Out back, the fun really begins: multiple composite decks with a pergola overlook a private, fully fenced yard backed by mature trees, creating your own outdoor retreat. The 20' x 30' saltwater above-ground pool takes summer entertaining to the next level. Inside, beautiful hardwood floors run throughout the main and upper levels. The main level offers an easy-flowing layout with a welcoming family room featuring a gas fireplace, separate dining and living rooms, plus a spacious kitchen with upgraded countertops, breakfast bar, and breakfast room. The first floor also includes a bedroom and full bathroom — ideal for guests, a home office, or flexible living arrangements. Upstairs, the spacious primary suite feels like a private escape, complete with double sinks, jetted tub, walk-in shower, and walk-in closet. Three additional bedrooms, a full bathroom, and conveniently located laundry complete the upper level. And then there’s the lower level — a huge bonus space ready for whatever your lifestyle demands. The large family room with wet bar is made for movie nights, game days, parties, or a dedicated entertainment space. An additional room plus a full bathroom offers incredible flexibility for a home gym, office, guest suite, teen hangout, or potential in-law setup. Outside your front door, you're conveniently located near Winchester Country Club, shopping, restaurants, and schools, giving you the best of both convenience and neighborhood living. This isn't just a house — it's the space to live the way you want now, with room for whatever comes next.

314 Huntersridge Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

4 Beds ⋅ 4 Baths

Come and discover this impressive beauty where easy main-level living meets exceptional indoor-outdoor entertaining. This beautifully appointed Cape Cod offers the convenience of a spacious main-level primary suite, while the heart of the home flows seamlessly from the well-appointed kitchen to a covered rear porch overlooking the sparkling inground pool and hot tub. With ceiling fans and a TV, the covered porch is an inviting gathering space for morning coffee, lazy summer afternoons, or movie night—truly an extension of the home all year long. Inside, the main level offers an ideal blend of an open floorplan and defined rooms with gleaming hardwood floors, soaring ceilings, crown molding, beautiful fresh paint, and an abundance of natural light. The kitchen features generous cabinet storage and prep space,a gas cook top, double ovens, built in microwave, a center island, and breakfast nook with direct access to the covered porch and expansive patio & pool area, making indoor-outdoor entertaining effortless. From the kitchen flow into the spacious living room with charming built-ins to find a warm and inviting place to relax and watch TV while being part of the action. This home also has a formal dining and living room (currently used as office) that flank the welcoming and generously sized foyer. The large main-level primary suite offers a private retreat with a relaxing en-suite bath featuring a soaking tub, step in shower, and huge walk-in closet. The main level is also home to laundry room and gorgeous powder room. Upstairs, three generously sized bedrooms share a full bath, providing comfortable accommodations for family and guests along with a loft area perfect as play area or reading nook. The versatile lower level expands the living space with ceramic tile throughout, a spacious recreation area, full bath, and finished room with closet that could serve as a fifth bedroom, home office, guest space, gym, media room, or game room. Outside, the covered rear porch, expansive patio, inground pool, and hot tub create a backyard designed for enjoying home to the fullest. The inviting front porch adds another charming outdoor space, perfect for morning coffee or winding down at the end of the day. A two-car garage, newer roof (2025), two-zone HVAC, and desirable corner-lot setting add to the home's appeal. Meaningful updates include new pool cover (3 years old), pool pump (2 years old) and brand new sand filter. Located in the quiet, Oakdale Crossing neighborhood, this home offers convenient access to Jim Barnett Park, Shenandoah University, Schools, Costco, Apple Blossom Mall, Winchester Country Club, and everyday amenities. Whether you're looking for the ease of main-level living, a comfortable home for entertaining, or your own private backyard retreat, 200 Fairfield Drive offers a wonderful combination of comfort, convenience, and lifestyle.

200 Fairfield Dr, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

4 Beds ⋅ 5 Baths

Space, style, and room to live your best life come together in this 4-bedroom, 4.5-bath, 3-level Colonial in desirable Oakdale Crossing. With flexible spaces, great indoor-outdoor living, and a location close to everything Winchester has to offer, this home is ready for whatever comes next. The main level features an open, inviting flow between the kitchen, breakfast room, and family room, where a gas fireplace creates the perfect spot to unwind. The kitchen offers granite countertops, while the dining room, living room, and dedicated office give you plenty of flexibility for everyday life. Crown molding and hardwood floors adds a polished touch throughout the main level. Upstairs, the spacious primary suite is your private retreat, complete with a large bath featuring double sinks, a soaking tub, shower and walk-in closet. Two additional bedrooms share a full bath, while a fourth bedroom offers its own en-suite bathroom—ideal for guests or anyone who wants extra privacy. The conveniently located upper-level laundry room makes laundry day a whole lot easier. The walkout lower level is where the fun happens! A huge recreation room with a second gas fireplace gives you space for movie nights, game days, or your favorite hobbies; plus there is an exercise room. A full bathroom with walk-in shower adds even more flexibility. Step outside through the walkout level to the patio and enjoy views of the large backyard—perfect for relaxing, entertaining, or letting your outdoor space become whatever you want it to be or head up to the TimberTech deck for outdoor dining, morning coffee, or summer gatherings. With shopping, restaurants, schools, and Winchester Country Club all nearby, you'll have convenience without giving up the space and privacy of a larger home. Come see how easily this home can fit the way you live today—and all the possibilities ahead. Plus no HOA!!

291 Huntersridge Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

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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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