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

205 Crestleigh Dr, Winchester
$630,000
4 Beds ⋅ 3 Baths
Extensively updated and thoughtfully maintained, this beautiful Colonial in the prestigious Oakdale Crossing community offers 2,884 square feet of living space, impressive outdoor amenities, and numerous improvements already completed. Recent updates include new siding and window trim in 2026, a new dishwasher in 2024, and a 2023 pool, tankless water heater, cooktop, refrigerator, and water softener. The roof was replaced in 2022, the HVAC system in 2018, and the front, back, and garage doors have also been replaced. Inside, you'll find four spacious bedrooms, 2.5 baths, rich wood flooring, crown molding, and an inviting layout designed for both everyday living and entertaining. The gourmet kitchen features granite countertops, a wall oven, cooktop, built-in microwave, and butler's pantry, with the dining area flowing naturally into the living space, where a cozy fireplace creates a welcoming focal point. The spacious primary suite offers a private retreat with an en-suite bath featuring a jetted tub. A wet bar and ceiling fans throughout add to the home's comfort and functionality. Looking for additional space? The 640-square-foot unfinished attic features subflooring and offers potential for future finishing, subject to applicable requirements. Create a home office, recreation room, additional living area, or keep it as valuable storage space. Set on a 0.35-acre corner lot, the outdoor living spaces are equally appealing. Enjoy the covered deck or relax beside the lighted, heated in-ground pool installed in 2023, complete with a hot tub for added enjoyment. An oversized side-entry garage and concrete driveway provide convenient parking and easy access. With extensive updates, generous living space, a versatile attic, and an inviting backyard retreat, this Oakdale Crossing Colonial offers a wonderful blend of comfort, functionality, and outdoor enjoyment. Check out the 3-D Tour attached to this listing!

205 Crestleigh Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact:

200 Fairfield Dr, Winchester
$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:

291 Huntersridge Rd, Winchester
$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:

Start Your Search

How much is your home worth?

Get instant property value now!