Oakdale Crossing Homes for Sale

Oakdale Crossing Homes for Sale

Welcome to Oakdale Crossing, a charming subdivision nestled in the heart of Winchester, Virginia, within the picturesque Frederick County. This vibrant community is not just a place to live; it's a lifestyle that combines the tranquility of suburban living with the convenience of urban amenities.

Oakdale Crossing boasts a variety of beautifully designed homes for sale, catering to diverse tastes and lifestyles. Whether you’re a first-time homebuyer or looking to upgrade, you’ll find an array of options that feature modern finishes, spacious layouts, and inviting outdoor spaces. Each home is thoughtfully constructed to provide comfort and style, ensuring that you and your family can create lasting memories in a place you truly love.

The subdivision is conveniently located near top-rated schools, making it an ideal choice for families. Residents enjoy easy access to parks, shopping centers, and dining options, all just a short drive away. The nearby historic downtown Winchester offers a delightful mix of boutiques, cafes, and cultural attractions, perfect for weekend outings.

Nature enthusiasts will appreciate the scenic surroundings, with walking trails and green spaces that encourage outdoor activities and community gatherings. The friendly atmosphere of Oakdale Crossing fosters a sense of belonging, making it easy to connect with neighbors and participate in community events.

Explore the homes for sale in Oakdale Crossing today and discover the perfect blend of comfort, convenience, and charm in this exceptional Winchester community. Your dream home awaits!

Newest Oakdale Crossing Homes for Sale

$619,900
4 Beds ⋅ 5 Baths ⋅ VAFV2043500 MLS
No HOA! Settled at the end of the cul-de-sac and pushed back from the street to give additional privacy and comfort. This home has received several improvements since 2020. Including a whole new kitchen (Dec 2025), soft close cabinets, quartz countertop and backsplash, Stainless Steel appliances, the kitchen island was enlarged for more countertop space and additional storage, seats 2-3 people comfortably. Kitchen includes a large pantry with upgraded doors (2025). Both HVAC Systems were replaced and a humidifier was added (Spring 2026). Ducts were professionally cleaned (2020). Custom Blinds (2025). The spacious back yard has an aluminum 5ft fence with 2 single gates and 1 double gate (2024). Trex Deck 12x16ft with gate at top of stairs (2021). Custom built 10x12ft swing for 3 people or a hammock. Trees and bushes and fencing makes the back yard feel very private. Interior and exterior professionally painted (2020/21). Large 12x16ft shed added (2023). New carpet in basement and upper level (2020). Updated both half bathrooms (2022-23). Primary bathroom has a heated tile floor, walk-in shower with rain fall shower head and 4 body sprayers, large jacuzzi tub, double vanity, chandelier, and linen closet. Primary bedroom has two walk-in closets. One with a chandelier and upgraded closet system. Garage has a Mini Split heating/cooling system as well as its own attic with flooring for storage. All interior and exterior light fixtures have been updated. Both gas fireplaces were professionally serviced (2023). Basement is wired for surround sound, has upgraded dry bar with soft close cabinets, quartz countertop to match kitchen, and floating shelves, the basement also has two windows for natural light, and walk-up basement stairs. Upstairs bedrooms have a Jack-n-Jill bathroom between them with an updated double vanity (2025). The rear bedroom has a walk-in closet with a laundry shoot. Professional landscaping in front of home (2021). Home is wired with ADT security but isn't currently in use. Location is excellent, almost everything you'd need is 5-10 minutes away including Winchester Country Club, Costco, Shopping Centers, Downtown walking mall, commuter routes like rt. 50, rt. 7, rt. 522, and Interstate 81.

308 Huntersridge Rd, Winchester
$709,900
4 Beds ⋅ 5 Baths ⋅ VAFV2043020 MLS
Executive Living in Oakdale Crossing Nestled in the highly desirable Oakdale Crossing community, this exceptional brick-front residence offers an impressive blend of elegance, comfort, and resort-style outdoor living. With approximately 3,400 square feet of above-grade living space, 4 bedrooms, 4½ bathrooms, two versatile bonus rooms, and additional basement space, this home is thoughtfully designed for both everyday living and entertaining. From the moment you arrive, the home’s classic architecture, manicured landscaping, and inviting front entry create a striking first impression. Inside, an open and updated floor plan features spacious living areas filled with natural light. The beautifully appointed kitchen offers white cabinetry, granite countertops, stainless steel appliances, a large center island, and an effortless flow into the surrounding living and dining spaces—ideal for family gatherings and entertaining. The true centerpiece of this property is the backyard. Designed as a private outdoor retreat, the custom saltwater gunite pool features elegant curves, wide entry steps, multiple integrated seating ledge.. Surrounding the pool is expansive stamped concrete decking, providing ample room for lounging and entertaining. Mature evergreen landscaping creates an exceptional sense of privacy, transforming the backyard into a peaceful, resort-inspired oasis. An expansive elevated deck spans the rear of the home, while the covered patio below offers additional shaded living space, making the outdoor areas enjoyable throughout the day and across multiple seasons. The property balances luxury amenities with practical outdoor space, leaving generous lawn areas for recreation while maintaining the beautifully landscaped setting. Additional highlights include: Approximately 3,400 sq ft of finished above-grade living space 4 spacious bedrooms. One being a master first floor 4½ bathrooms Two flexible bonus rooms ideal for a home office, fitness room, playroom, media room, or guest space Updated kitchen with granite countertops, stainless steel appliances, and center island Custom saltwater gunite pool Extensive stamped concrete hardscaping Expansive rear deck with covered entertaining area below Mature privacy landscaping Two-car garage Located in the sought-after Oakdale Crossing community This home offers a rare combination of timeless curb appeal, thoughtfully updated interiors, and an exceptional outdoor living environment. From relaxing poolside on summer afternoons to hosting family gatherings under the covered patio, every aspect of the property has been designed to enhance both comfort and lifestyle.

297 Huntersridge Rd, Winchester
$649,000
4 Beds ⋅ 3 Baths ⋅ VAFV2042904 MLS
Welcome home to this beautifully maintained 3-level Colonial, perfectly situated on a quiet cul-de-sac in the highly desirable Oakdale Crossing community. Offering 4 bedrooms, 2.5 baths, and spacious living areas throughout, this home blends timeless style with modern updates. The main level is designed for both everyday living and entertaining, featuring formal living and dining rooms with hardwood floors, crown molding, and chair rail accents. The inviting family room showcases hardwood flooring, custom built-ins, crown molding, and a cozy gas fireplace. At the heart of the home is the beautifully remodeled kitchen, completed in 2023, featuring new cabinetry, upgraded countertops, ceramic tile flooring, double wall ovens, gas cooking, and abundant cabinet and counter space. The adjoining breakfast area is filled with natural light and opens to the covered rear porch, creating the perfect indoor-outdoor living space. Enjoy peaceful mornings on the covered front porch or entertain in the fully fenced backyard with low-maintenance vinyl fencing and a swing set. The upper level features a spacious primary suite with two walk-in closets and a spa-like bath complete with a jetted soaking tub, walk-in shower, and double vanity. Three additional bedrooms, a full hall bath, a versatile loft, and the convenience of an upper-level laundry room complete the second floor. The unfinished walk-up basement offers incredible potential for future living space, complete with multiple windows for natural light and a bathroom rough-in already in place. Located in one of Oakdale Crossing's most desirable cul-de-sac locations, this exceptional home offers the perfect combination of space, comfort, and convenience. With a beautifully remodeled kitchen, room to grow, and thoughtful features throughout, this move-in-ready home is one you won't want to miss.

104 Bramble Ct, Winchester
$627,102
5 Beds ⋅ 4 Baths ⋅ VAFV2042412 MLS
Price Drop. Come check this home out. The listing remarks below come directly from the Seller's. This home is a true gem. Hello! Human here! I just want to touch base with you on this thoughtfully designed home for sale in the renowned Oakdale Crossing subdivision. This smaller subdivision has a lot of homes with styles that are unique in the market. And this home has a nice balance of spacious casual function and real formal rooms that brings the space to life with its 5 BR, 3.5 BA configuration. The owners of the last 17 years have really maintained this place. The beautiful oak wood floors are gleaming with pride throughout the first floor. Granite countertops in the kitchen and first floor powder room give it pop! The formal living room has a fireplace and cathedral ceiling to add beautiful dimension, and the formal dining room has a stateliness about it. Sure, tastes are subjective and may not always be your ambience, but the rooms are large, solid and useful, and you can plainly envision the positives to fit your lifestyle. The kitchen is big enough and shining with stainless steel appliances, double built-in ovens, an awesome kitchen island with a Jenn-Air stove top all complimented by warm cherry cabinets. Off to the side of the kitchen rests the spacious family room framed by another fireplace in the home. This room shines in the natural light of the afternoon sky with 9’ ceilings within this wide-open space. You can “Really Breathe” in these spaces as it beams in the daylight. Oh, and before I forget, a large office area with built-in shelves and desktop area for two computer spaces rounds out the appeal to the main floor. A definite must for the entrepreneur or remote worker. This home has you covered! Now the upstairs is great, too. All new carpet has been added to the 4 BR areas. The primary bedroom has a recently upgraded bathroom with a 5’ glass enclosed shower, two separate vanities on separate walls, a jet tub to soak in on those days when you “Just Over Did It”. All of the BRs are large and accommodating for your personal furnishings. And there’s tons of closet space that is so needed for those “I may wear this, use this, want this someday” to gently hide from sight. I mean, there’s a LOT to like about this floorplan. Of course, we also have a finished basement that goes on for miles! Okay, not miles, but it’s got the room for just about anything! Besides a large area for play, there’s an entertainment area with yet another fireplace to set the mood, a full bath with shower to use on those days when you can step in from the backyard after yard work to clean up, and a large 5th BR setup that you can use as such, or as an art/music room, or as the “ It’s great I can have my own exercise room so one less monthly subscription! Yay!” You can definitely let you imagination run wild in this basement. As far as the most important functions of the place, there’s new Anderson windows throughout the home. Dual HVAC/heat pumps have been upgraded within the last few years, as well as new architectural roof, water heater, and custom blinds in major areas. So, a lot of care has been taken to keep its stature. There’s so much to see here and so little space to tell you about it. It is perfect? No, of course not. But this place is solid and just needs a lovely occupant to lay roots and memories. So, come take a look!

295 Huntersridge Rd, Winchester
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