Oakdale Crossing Real Estate

Oakdale Crossing Real Estate

Welcome to Oakdale Crossing, a hidden gem nestled in the heart of Winchester, Virginia. This charming subdivision offers a perfect blend of suburban tranquility and modern convenience, making it an ideal choice for families, retirees, and everyone in between.

Oakdale Crossing is strategically located in Frederick County, providing residents easy access to the vibrant city of Winchester, known for its rich history, scenic landscapes, and a plethora of recreational activities. The community is surrounded by lush greenery and picturesque views, creating a serene environment that invites relaxation and outdoor enjoyment.

Within Oakdale Crossing, you’ll find beautifully designed homes that cater to a variety of lifestyles. From spacious single-family homes to cozy townhouses, there’s something for everyone. The well-maintained streets and friendly neighbors foster a sense of community, making it easy to forge lasting friendships.

Families will appreciate the nearby schools, which are part of the highly-rated Frederick County Public School system. Parks, playgrounds, and walking trails are just a stone's throw away, providing endless opportunities for outdoor fun and exercise.

For those who enjoy shopping and dining, Winchester boasts a delightful array of local boutiques, restaurants, and cafes, ensuring that you’ll never run out of options to explore.

Whether you’re seeking a peaceful retreat or a vibrant community, Oakdale Crossing is the perfect place to call home. Discover the charm of this exceptional subdivision and experience the best of Winchester living. Welcome to your new beginning!

Newest Listings in Oakdale Crossing

$645,000
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:

$659,900
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
$725,000
5 Beds ⋅ 4 Baths
Beautifully remodeled with exceptional care and attention to detail by its current owners, this stunning 5-bedroom, 3-bath home offers over 4,400 finished square feet on a private 0.35-acre corner lot with NO HOA. Thoughtfully designed for comfortable everyday living, the home features four bedrooms on the upper level and a fifth bedroom on the main level with convenient access to a full bath, ideal for guests, a private home office, or additional living space. The main level showcases hardwood flooring, a spacious family room with an impressive stone fireplace, and an elegant formal dining room enhanced by decorative moldings. The gourmet kitchen, renovated in 2021, features quartz countertops and backsplash, a large center island, a pantry, and a built-in desk/workstation, perfect for working from home, organizing daily tasks, or a study area. The outdoor spaces are equally inviting and include a covered rear porch, a renovated deck (2024), a paved patio (2022), and a fully fenced backyard—perfect for relaxing or enjoying time with family and friends. The fully finished walk-out basement with its own private entrance offers exceptional versatility. It features a spacious open recreation area with a kitchenette, a full bathroom, and two finished bonus rooms that can easily be used as an office, gym, playroom, hobby room, media room, or any flexible space to fit the new owner's needs. Major improvements completed by the current owners include new flooring (2021), renovated bathrooms (2021), new fence (2022), paved patio (2022), renovated deck (2024), basement renovation with kitchenette and full bathroom (2024), primary bathroom renovation (2025), fresh interior paint throughout (2026), plus new windows and a new HVAC system. Conveniently located near shopping, restaurants, Route 7, Route 50, and I-81, this meticulously maintained home combines modern updates, versatile living spaces, and the convenience of being truly move-in ready.

223 Fairfield Dr, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$624,900
4 Beds ⋅ 3 Baths
Welcome to this beautifully maintained 3-level Colonial tucked away on a quiet cul-de-sac in sought-after Oakdale Crossing. With 4 bedrooms, 2.5 baths, a remodeled kitchen, spacious living areas, and room to make the home your own, this is the kind of place that checks the boxes for today—and gives you plenty of space for whatever comes next. The main level is made for living, hosting, and everyday moments. Hardwood floors, crown molding, and chair rail details add timeless character to the living and dining rooms, while the family room brings a more relaxed feel with hardwood flooring, custom built-ins, crown molding, and a cozy gas fireplace. At the center of it all is the beautifully remodeled 2023 kitchen, featuring new cabinetry, upgraded countertops, ceramic tile flooring, double wall ovens, gas cooking, and tons of storage and prep space. The bright adjoining breakfast area opens directly to the covered rear porch, making morning coffee, weekend brunch, and summer entertaining feel effortless. Outside, you’ll find two inviting porches and a fully fenced backyard with low-maintenance vinyl fencing and a swing set. Whether you’re enjoying a quiet morning on the front porch or gathering with friends in the backyard, there’s room to enjoy the outdoors without the upkeep of a huge property. Upstairs, the spacious primary suite is your private retreat, complete with two walk-in closets and a spa-like bath featuring a jetted soaking tub, walk-in shower, and double vanity. Three additional bedrooms provide flexibility for guests, a home office, gym, or whatever fits your lifestyle. A full hall bath, versatile loft, and the convenience of an upper-level laundry room round out the second floor. And there’s even more potential downstairs. The unfinished walk-up basement is ready for your vision, with multiple windows bringing in natural light and a bathroom rough-in already in place. Create the ultimate rec room, home gym, office, guest suite, or additional living space when the time is right. With its cul-de-sac setting, modern kitchen, generous living space, outdoor entertaining areas, and room to grow, this Oakdale Crossing home offers the lifestyle today's buyers are looking for—with plenty of opportunity to make it uniquely yours. Move-in ready, thoughtfully updated, and ready for its next chapter. Come see why this one belongs at the top of your list.

104 Bramble Ct, Winchester

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