Woodstock Homes under $500,000

Woodstock Homes under $500,000

Welcome to Woodstock, Virginia – a charming town nestled in the heart of Shenandoah County, where picturesque landscapes meet a rich tapestry of history and community spirit. Known for its warm hospitality and vibrant local culture, Woodstock offers a delightful blend of small-town charm and modern conveniences, making it an ideal place to call home.

With the stunning Blue Ridge Mountains as a backdrop, Woodstock is surrounded by natural beauty, providing residents with ample opportunities for outdoor activities such as hiking, fishing, and exploring the nearby George Washington National Forest. The town itself boasts a lively downtown area filled with unique shops, cozy cafes, and delicious dining options, all contributing to the welcoming atmosphere that defines this community.

For those seeking a new home in Woodstock, you’ll be pleased to discover a variety of properties available under $500,000. Whether you’re looking for a quaint cottage, a spacious family home, or a modern townhouse, Woodstock has something to suit every taste and budget. These homes often feature charming architectural details, lovely backyards, and easy access to local amenities, making them perfect for first-time buyers, families, or anyone looking to enjoy a serene lifestyle in a picturesque setting.

Living in Woodstock means embracing a laid-back lifestyle while still being close to larger cities like Winchester and Harrisonburg. With its rich history, vibrant community, and beautiful surroundings, Woodstock, Virginia, is truly a hidden gem waiting to be discovered. Come explore your future home in this enchanting town today!

Newest Woodstock Homes under $500,000

335 S Commerce St, Woodstock
$339,000
3 Beds ⋅ 2 Baths
Discover a beautifully maintained three-bedroom, two-bathroom home in charming downtown Woodstock. Designed for convenient single-level living, the property is equally well suited as a primary residence or an investment opportunity, including short-term rental or traditional lease use. The open-concept living and dining areas create a bright, welcoming flow throughout the home. At the rear, the private primary suite includes a walk-in closet and direct access to the back deck and yard. Framed by mature landscaping and scenic views, the deck provides a peaceful setting for quiet mornings or relaxing evenings. A convenient location with easy access to all of the following: • Woodstock Town Park, downtown cafés and shops, banking, and health care facilities are all nearby. • Seven Bends State Park provides convenient access to outdoor recreation. • Interstate 81 is less than two miles away, and Route 11 is approximately half a mile from the home. Call today to discuss how this amazing property can be yours.

335 S Commerce St, Woodstock

Listing courtesy of Johnston and Rhodes Real Estate. Contact:

238 Indian Spring Rd, Woodstock
$330,000
3 Beds ⋅ 2 Baths
Welcome to 238 Indian Spring Road! Solid split-foyer home on nearly half an acre parcel. Built in 1976, this home offers an easy layout and outdoor space to enjoy. The kitchen features light wood cabinetry with a peninsula that makes entertaining easy. The combined kitchen and dining area leads through a sliding glass door onto the covered back deck with a ceiling fan — a great spot for morning coffee or evening dinners. Beneath the deck, the walkout basement offers easy access through its own sliding glass doors. Cozy up in the living room by the brick fireplace on chilly evenings. The basement offers a second brick fireplace, making it easy to add a rec room or extra living space. Baseboard heating keeps things simple and efficient, with air conditioning window units. Outside, you'll find an above-ground pool for summer days and a storage shed for extra space — all set on a spacious 0.46-acre lot with room to spread out. This home is very close to Woodstock's Indian Springs Wetland Park - a peaceful 1-acre nature reserve with a walking trail and observation deck. Located just minutes from downtown Woodstock - with lots of restaurants, shops, a movie theater, and more! Schedule your showing today!

238 Indian Spring Rd, Woodstock

Listing courtesy of Skyline Team Real Estate. Contact:

1290 Ox Rd Unit E-6, Woodstock
$145,000
2 Beds ⋅ 2 Baths
Welcome to 1290 Ox Road #E-6 in Woodstock! This beautifully remodeled 2-bedroom, 2-bath condo offers 1,195 square feet of updated, move-in-ready living space with fresh paint and modern finishes throughout. Luxury vinyl plank flooring creates a clean, cohesive look, while the beautifully updated kitchen features new appliances, stylish finishes, and a dedicated dining area perfect for everyday meals or entertaining. Both full bathrooms have also been updated, giving the home a fresh, modern feel from room to room. The spacious primary bedroom offers its own private ensuite bathroom and a walk-in closet, while the second bedroom provides flexibility for guests, a home office, or additional living space. New French doors lead out to the deck, creating an inviting spot to relax and enjoy the outdoors with mountain views. Additional updates include a new washer and dryer and fresh interior paint throughout. HOA fees add to the convenience of condo living and include common area maintenance, lawn maintenance, snow removal, water, and trash service. With extensive updates, a comfortable layout, and low-maintenance living, this Woodstock condo is ready for its next owner to move right in and enjoy!

1290 Ox Rd Unit E-6, Woodstock

Listing courtesy of Samson Properties. Contact:

1023 Sun Poppy Ct, Woodstock
$399,000
3 Beds ⋅ 2 Baths
This is your opportunity to own a Beautiful home in Hisey Park. A place to simplify your lifestyle without giving up comfort, space, or convenience. This home features three bedrooms with two baths, granite countertops, all on one-easy level. If you're ready to downsize, planning for retirement, or simply tired of dealing with maintenance or stairs, then this is the one for you. New Appliances were installed in 2024 & come with a transferrable warranty until 2029, The Water Heater was installed in 2025, Mowing & Snow Removal are paid until 12/31/2026. Come view this low-maintenance property, relax on the Patio, take in the wildlife, the mature landscaping and imagine it as Home!

1023 Sun Poppy Ct, Woodstock

Listing courtesy of ERA Valley Realty. Contact:

605 Cedar Ct, Woodstock
$399,900
3 Beds ⋅ 3 Baths
Beautifully maintained split foyer home nestled in the desirable Orchard View community. It features 3 spacious bedrooms, 3 full bathrooms, and a 2-car garage. Step inside to find stunning hardwood floors throughout the main living areas, plus crown molding and recessed lighting that create an inviting atmosphere. The heart of the home is the country-style kitchen, featuring modern appliances including a built-in microwave, dishwasher, and electric range, making meal prep a delight. Enjoy casual dining in the eat-in area or host gatherings in the family room that seamlessly connects to the kitchen. The primary suite features a spacious bath and a large walk-in closet. The fully finished basement is ideal for entertaining or relaxing, with convenient access to the garage. Outside, you enjoy the new deck overlooking serene wooded views, perfect for morning coffee or evening gatherings. In a vibrant community, residents enjoy nearby parks and community amenities. With a spacious 0.53-acre lot, this home offers both tranquility and convenience, making it a perfect place to create lasting memories.

605 Cedar Ct, Woodstock

Listing courtesy of Samson Properties. Contact:

358 W Spring St, Woodstock
$329,900
4 Beds ⋅ 2 Baths
Welcome home to this beautifully RENOVATED Cape Cod offering modern comfort, classic charm, and ideal location in the heart of Woodstock, Virginia. Featuring an inviting open floor plan, this spacious home offers four bedrooms and two full baths, providing plenty of room for family, guest, or a home office. The thoughtfully updated interior creates a bright, welcoming atmosphere with an easy flow between the living, dining, and kitchen areas- perfect for everyday living and entertaining. A large full unfinished basement provides abundant storage and tremendous potential for future living space, a workshop recreation area, or whatever best suits your needs. Step outside and enjoy the large covered deck, an ideal spot for morning coffee, outdoor dining, or entertaining family and friends while taking in the beautiful mountain views. The expansive backyard offers plenty of room for gardening, recreation, pets or simply relaxing and enjoying the outdoors. Located in town and close to the town park and all of Woodstock's amenities, this home combines the convenience of being near shopping, dining, recreation and community activities with the peaceful beauty of the Shenandoah Valley.

358 W Spring St, Woodstock

Listing courtesy of Johnston and Rhodes Real Estate. Contact:

816 Burgess Ct, Woodstock
$425,000
3 Beds ⋅ 3 Baths
Motivated sellers! Discover the charm of this beautifully renovated Colonial home in Wellington Estates, where modern elegance meets comfort. With 3 spacious bedrooms and 3 full bathrooms, this residence boasts an open floor plan that invites natural light throughout. The heart of the home features stainless steel appliances, including a built-in microwave and dishwasher, perfect for culinary enthusiasts. Enjoy the convenience of main-floor laundry and an oversized garage. Set on a generous 0.53-acre lot, the property offers lush front and rear yards, ideal for outdoor gatherings or serene moments in your garden. The 2022 renovations ensure a fresh, contemporary feel while maintaining the home's classic appeal. Located in a vibrant community, residents benefit from nearby parks, excellent schools, and convenient public services. Embrace a lifestyle of comfort and connection in this delightful neighborhood, where every day feels like a retreat. Don't miss your chance to call this stunning property home!

816 Burgess Ct, Woodstock

Listing courtesy of Kathy Jean Campbell. Contact:

268 Parkside Ct, Woodstock
$349,900
3 Beds ⋅ 3 Baths
Welcome to this beautifully upgraded townhouse offering 1,872 square feet of living space! Beautiful Northwood LVP flooring throughout the main level. The kitchen features quartz countertops, $500 upgraded backsplash, white cabinetry, and a gas range. Upstairs, you'll find three generously sized bedrooms, including a primary suite complete with a walk-in closet and private ensuite bathroom. A spacious linen closet in the upstairs hallway adds even more convenient storage, along with new shelving throughout all closets. The home has had significant upgrades, including a stunning $20,000 handicap-accessible walk-in shower with stone walls, and $7,000 Stainmaster upgraded carpet. Dual A/C and heating system. Additional features include a single-car attached garage, a laundry station, and a shed in the backyard for extra storage. Move-in ready. Schedule your tour today!

268 Parkside Ct, Woodstock

Listing courtesy of Skyline Team Real Estate. Contact:

769 S Water St, Woodstock
$479,000
4 Beds ⋅ 2 Baths
One of a kind, hidden gem in the heart of the Town of Woodstock. This 4 BR, 2 Bath split level home with garage is perfectly sited on a private, 3.2-acre wooded homesite. A truly scenic vista located so close to the the Town of Woodstock. There is always something fun to do and enjoy in Woodstock--where vineyards, hiking,, fine restaurants, and quaint cafes are located very nearby. The Valley Health Shenandoah Hospital is located across the street. You love to explore your own nature trails and also visit the Indian Spring Wetland park directly across the street. Grocery, banks, quaint dining, and recreational opportunities are within minutes. This home features an upgraded kitchen and baths, a newer roof in 2019, HVAC- furnace replaced in 2022. This multi-level split home has a sunny primary bedroom with French doors leading to a private deck. You'll love morning coffee or evening cocktails on the deck while enjoying the sounds of nature. Three additional bedrooms, including the attic space, which will easily serve as a home office. The living and dining room open with French doors to a patio--ideal for entertaining. The living room has a wood-burning fireplace with built-in bookcases on either side. Gleaming hardwood flooring is found in this area, as well as in the 3 bedrooms. The upgraded kitchen is a chef's delight with custom cabinetry, upgraded countertops, ceramic flooring, and stainless steel appliances. Now is the time to discover this private oasis located in the heart of the Town of Woodstock within the beautiful Shenandoah Valley. The property is a mix of ferns, mature hardwood trees, a meandering stream and a cleared lush lawn. Wildlife abounds with new fawns frolicking through the yard. A natural stream originates on the property and runs to the Indian Spring Wetland Park area. Huge rock and boulders dot the landscape throughout the woods. You can expand the house--consider all the opportunities to design and build out this property to your absolute heart's content. Schedule a Tour today!

769 S Water St, Woodstock

Listing courtesy of Samson Properties. Contact:

170 Clubhouse Ct, Woodstock
$345,000
3 Beds ⋅ 2 Baths
You can have it all with this 3-bedroom home located in the Leisure Point community! The open living room, dining room, and kitchen make a great space for gatherings. The living room features hardwood floors and vaulted ceilings. Down the hallway you'll find the primary bedroom with an ensuite bath and walk-in closet, two additional bedrooms, a full bath, as well as a laundry station and linen closet. Recent updates include new carpet, fresh paint, and shingles replaced in 2019, making this one move-in ready. Step outside to a spacious backyard with an outbuilding, and take in the beautiful mountain views from your front porch over a morning coffee or evening tea. Living in Leisure Point means private community access to the Shenandoah River — picture riverside picnics, fishing, or a relaxing stroll through nature.

170 Clubhouse Ct, Woodstock

Listing courtesy of Skyline Team Real Estate. Contact:

1122 Wadewood Ct, Woodstock
$224,500
2 Beds ⋅ 2 Baths
REDUCED PRICE: Interior Townhouse ready for first time homebuyer or investment property. Large Kitchen & Breakfast Room w/pantry and Laundry area enclosed in Kitchen area. Half Bath on main level and Large Living Room. Vinyl Plank & Carpet Flooring. Cement covered porch on back and storage room off porch. Partially fenced in back yard. 2- large bedrooms w/double closets on upper level and 1-full Bathroom. Walk up Attic stairs for partially floored attic for storage. Heat Pump New in 2020. New Roof 2025. New Electrical Panel 2025. ** Seller offering $4,000 credit to Buyer for Closing Cost** Conveniently located for shopping, schools and medical needs.

1122 Wadewood Ct, Woodstock

Listing courtesy of Sager Real Estate. Contact:

1045 S Main St Unit C-9, Woodstock
$220,000
3 Beds ⋅ 2 Baths
Welcome home to this adorable, move-in-ready townhouse just minutes from the heart of Woodstock! This charming two-level home offers 3 bedrooms, 1.5 baths, and a long list of thoughtful updates that make it truly ready for its next owner. Step inside to find beautiful LVP flooring throughout, fresh paint, updated light fixtures, and a bright, refreshed feel from top to bottom. The kitchen shines with new stainless steel appliances, new backsplash, while additional updates include a new washer/dryer combo, new sliding glass door, and new storm door. Outside, enjoy the privacy of a 6-foot vinyl fence installed in 2024, perfect for relaxing, entertaining, or letting pets play. Major improvements include a roof replaced in 2022 and an HVAC system approximately six years young, offering even more peace of mind. And the location? You’re just a hop, skip, and a jump from the heart of Woodstock, with shopping, restaurants, local favorites, and everyday conveniences all close by. Thoughtfully updated, beautifully maintained, and truly move-in ready; this one is ready to welcome its new owners. Schedule your showing today!

1045 S Main St Unit C-9, Woodstock

Listing courtesy of Samson Properties. Contact:

Start Your Search