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$330,000
2 Beds 2 Baths
Welcome to 234 N. Main Street in the heart of Woodstock, where small-town charm, everyday convenience, and classic character all come together. Perfectly located near local shops, restaurants, and downtown favorites, this inviting home gives you a front-row seat to Woodstock’s beloved town parades right from your own front porch. Inside, you’ll find a spacious living room filled with charm and warmth, offering a comfortable place to gather, relax, or unwind at the end of the day. The main level also features a full bathroom with laundry, plus a flexible nook that could make a great play space, reading corner, or home office. The updated eat-in kitchen is full of personality and is sure to be a favorite spot in the home. A large butcher block island offers plenty of prep and gathering space, while the dining area provides room for a generous table. The beautiful fireplace serves as the centerpiece of the kitchen, adding character and charm you don’t often find. Upstairs, you’ll find two nicely sized bedrooms and an incredibly charming bathroom with a classic clawfoot bathtub. Out back, enjoy a covered rear porch, newly built outbuilding, and rear parking with room for multiple vehicles, an incredible bonus for a downtown Main Street location. With its inviting layout, charming details, and walkable Woodstock setting, 234 N. Main Street is ready to welcome you home.

234 N Main St, Woodstock

Listing courtesy of LPT Realty, LLC. Contact: 8773662213

$359,000
2 Beds 2 Baths
Enjoy beautiful mountain views and the convenience of one level living in this well maintained two bedroom, two bath brick duplex located on a corner lot in the desirable Camelot Estates community. Offering 1,629 square feet, this home features an attached 2-car garage, an oversized concrete driveway, and professionally landscaped grounds with attractive native plantings. Inside, you'll find hardwood flooring throughout most of the home, 9'+ ceilings with crown molding, and a spacious living room with a propane fireplace and mantel. The oversized primary suite offers a walk-in closet and private bath, while the generous second bedroom features a bump-out and beautiful mountain views. Additional highlights include abundant closet and storage space, a custom brick patio with a permanent propane hookup for your grill, and a quiet backyard perfect for relaxing or entertaining. Conveniently located just minutes from downtown Woodstock, shopping, restaurants, medical offices, the hospital, and the Shenandoah County Fairgrounds. With no HOA, all-brick construction, and pride of ownership throughout, this exceptionally clean, non-smoking home is move-in ready and offers low-maintenance living in a peaceful setting.

140 Donna Dr, Woodstock

Listing courtesy of ERA Valley Realty. Contact:

$650,000
This unique commercial property blends rustic character with practical functionality, offering an exceptional opportunity for a business looking to stand out. Originally a barn, the building has been thoughtfully converted into versatile commercial space featuring durable metal siding and a metal roof, along with a welcoming covered entry and three separate entry doors for convenient access. Inside, you'll find a spacious carpeted lobby, his and hers half baths, two receptionist offices, multiple storage areas, a kitchen, laundry room, conference room, unfinished half bath, and a large work/project room ideal for a variety of business uses. The basement level provides additional storage space, another half bath, and two ground- level exits for added accessibility. An established tenant currently occupies the remainder of the basement which is currently used as office space, providing immediate income for the new owner. Outside, the property includes a 40'x16' metal carport, additional storage buildings, paved parking lot, and a classic silo that enhances the property's distinctive appeal. Conveniently located close to all amenities, this one-of -a -kind property offers excellent visibility, functionality, and character to help your business make a lasting impression. This property is also available for lease

140 Lora Dr, Woodstock

Listing courtesy of Pangle Real Estate and Auction Co, Inc.. Contact:

$985,000
Don't miss out on this opportunity to purchase the iconic Spring House in Woodstock, VA. Spring House has been in operation as a full service restaurant for well over 30 years and is a fixture on Main Street Woodstock. Originally built in 1952 and extensively renovated in 2015-2020, Spring House offers a unique blend of historic charm and modern functionality. Nestled in the heart of downtown, this property boasts a prime location making it an ideal investment opportunity. Spanning 0.63 acres, the lot features Main St road frontage and a large parking lot for patrons and employees. The restaurant is bordered by Spring Hollow creek, enhancing the property's appeal with its natural features and perfect for businesses looking to attract clientele seeking a relaxing environment. The new Owner can expand on this concept with rooftop seating or a cantilevered deck over the creek bed. The interior features two main dining rooms, one in front and one in the rear with an added bar area. Together they seat 86. In between there are two smaller dining rooms for private parties or those seeking a cozy room to themselves. Together these two dining rooms seat 36. Upstairs is mostly unfinished but features a 23'x30 space with two half baths, storage and the manager/owner's office. This space could be finished as an employee break room, conference room or another private dining room for parties. The restaurant has a full bar in the log section of the building that seats 22. The property is in very good condition, ensuring minimal immediate maintenance needs for the new owner. Parking is convenient with options for on-street and parking lot access, accommodating both customers and employees. The downtown location not only enhances visibility but also positions the property within a growing community. Numerous housing developments in Woodstock are coming online in 2026 and 2027. These will add new patrons to the existing faithful following of patrons. This sale is for the real estate, kitchen equipment, cookware, dining room decor and dishware. The restaurant is open for business every day except Tuesday, and will remain so until sold and transitioned to the new Owner Operator. The Seller/Owner Operator will assist the Buyer with the transition of the restaurant and it's 26 employees (8 of which are part time). Gross sales receipts and a full list of equipment to convey are available upon request.

325 S Main St, Woodstock

Listing courtesy of Preslee Real Estate. Contact: 5402274416

$419,999
3 Beds 3 Baths
Welcome home to this beautifully maintained ranch offering charm, comfort, and stunning mountain views! From the moment you arrive, you’ll be drawn in by the eye-catching stone front accent, freshly mulched landscaping, and vibrant flowers beginning to bloom—creating the perfect first impression. A new roof installed in 2024 adds even more value and peace of mind. Step onto the inviting covered front porch and into a bright and welcoming living room featuring a cozy gas fireplace, perfect for relaxing evenings. Large windows fill the space with natural light, and the open layout flows seamlessly into the dining area and kitchen. The kitchen offers solid wood cabinetry, ample storage, and a recently updated dishwasher, making it both functional and inviting. Just off the dining area, you’ll find a beautiful enclosed sun porch—an ideal spot to unwind while taking in peaceful mountain and backyard views. Step outside to the rear deck, perfect for entertaining, grilling, or simply enjoying the outdoors. The main level also features a convenient laundry area, two comfortable guest bedrooms, a full bathroom, and a spacious primary suite. The primary bedroom includes two closets, one being a large walk-in, and an attached bath complete with a double vanity, soaking tub, and walk-in shower. The walk-out lower level expands your living space with a large family room, an additional room perfect for a home office or guest space, a half bath, and a generous storage area. Outside, enjoy a spacious backyard complete with a storage shed and plenty of room to relax or play. The driveway offers ample parking for guests and everyday convenience. This home truly combines comfort, functionality, and scenic beauty—don’t miss your opportunity to make it yours!

515 Hollingsworth Rd, Woodstock

Listing courtesy of Realty ONE Group Old Towne. Contact: 5404592727

$900,000
Rare opportunity to acquire nine (9) fully approved, shovel-ready townhome lots in the Town of Woodstock, Virginia. The property is configured as three separate rows, with three lots in each row, and may be purchased as individual 3-lot groupings or as a full 9-lot package. These finished lots have been fully engineered and approved, helping reduce development time and minimizing upfront entitlement risk. Public water, sewer, and electric are available on site, and civil work has been completed to support immediate vertical construction. Buyers need only finalize building plans and secure permits to begin. Situated in a growing area with solid demand for new housing, this is an ideal opportunity for builders, investors, and developers looking for a ready-to-go townhome project. Flexible purchase options available. Buy one row of 3 lots or purchase all 9 lots together. Listing agent has an ownership interest in the property. All information is deemed reliable but not guaranteed and is provided for informational purposes only. Buyer and buyer’s agent to verify all information and perform their own due diligence.

113 Flora Vista Ln, Woodstock

Listing courtesy of Onest Real Estate. Contact: 8336637802

$145,000
Prime opportunity to build in the heart of downtown Woodstock! This exceptional vacant Main Street lot is ideally positioned directly across from Massanutten Military Academy and within easy walking distance to boutique shopping, dining, breweries, and wineries. The location offers a rare blend of small-town charm and vibrant lifestyle amenities, making it equally appealing for a primary residence, second home, or investment property. Outdoor enthusiasts will appreciate close proximity to parks, the scenic Shenandoah National Park, and the North Fork of the Shenandoah River—perfect for kayaking, fishing, and swimming. Whether enjoying a peaceful morning on the river or an afternoon exploring nearby trails and vineyards, this location delivers an elevated Shenandoah Valley lifestyle. This build-ready lot offers a significant advantage with public water and sewer already installed and tap fees paid—saving both time and upfront development costs. Bring your vision and design a custom home tailored to your lifestyle in one of Woodstock’s most desirable in-town settings. With its prime location, walkability, and ready-to-build status, this property also presents a compelling opportunity for long-term value and investment potential.

539 S Main, Woodstock

Listing courtesy of Cain Valley Realty. Contact: 5407185349

$310,000
3 Beds 1 Baths
Come see this 3 Bedroom Ranch Style Home with One Bath. This adorable house in the country is just waiting for a family to enjoy it! A Beautiful huge deck spans the entire front of the home and extends around the side Home has new replacement windows in 2023, New roof in 2021, New HVAC System in 2022. Offering a wonderful place to sit and enjoy the pastoral views of the countryside and the neighboring farms. This property offers country living and the convenience of being a few short minutes to the town of Woodstock and all it has to offer, as well as being convenient to the interstate for easy commutes. This beautifully landscaped home offers single level living and plenty of space for gardening on the almost 1 1/2 acres of ground. This is one to check out! Subject to Seller finding suitable Housing.

2212 Swartz Rd, Woodstock

Listing courtesy of Johnston and Rhodes Real Estate. Contact:

$699,900
4 Beds 5 Baths
NEW PRICE REDUCTION !! Meticulously Renovated Colonial on 2.15 Acres with In-Law Suite & Smart Features Welcome to this exquisitely renovated 4-bedroom, 4.5-bath Colonial in the prestigious Spring Hollow Estates. Set on a private 2.15-acre lot, this nearly 5,000 sq ft residence blends timeless architecture with high-end modern upgrades—just a couple minutes from I-81 and the vibrant town of Woodstock. Renovated to an exceptional standard, this home features hardwood flooring across all three levels, elegant tilework, custom millwork, and refined lighting throughout. The main level includes formal living and dining rooms with crown molding and chair rail, a sunlit living room centered around an unused brick fireplace, and a designer kitchen with quartz countertops, smart stainless steel appliances, and abundant natural light. Upstairs, the spacious primary suite offers a spa-like bath with a freestanding soaking tub, glass-enclosed shower, and marble-topped dual vanity. One additional bedroom includes a private en-suite bath, while two more bedrooms share a third full bath—perfect for family or guests. The fully finished walk-out lower level features a complete in-law suite with a kitchenette, full bath with marble vanity, private laundry, and its own entrance—ideal for multigenerational living or flexible accommodations. Step out from the family room onto a maintenance-free composite deck with peaceful easterly views. The backyard backs to mature woods and enjoys exceptional privacy with no neighbors on two sides. Key Features and Recent Upgrades: New energy-efficient windows throughout New roof, heat pump, and water treatment system with two new hot water tanks Smart switches, USB outlets, and Google Nest thermostats Smart appliances and 4-camera Ring security system Oversized 2-car garage with new garage door opener and decorative flooring Extensive mechanical improvements throughout This move-in-ready home delivers space, quality, and smart living in one of Woodstock’s most desirable neighborhoods

405 Spring Hollow Rd, Woodstock

Listing courtesy of Re/Max Roots. Contact: (540) 686-7362

$379,000
4 Beds 2 Baths
Charming ranch in the heart of Woodstock — just one block from shopping and dining. This solid and bright 4-bedroom, 2-bath home includes a versatile elevated office that is attached to the garage and can easily serve as the fourth bedroom. The full basement is dry and features built-in work benches for projects and storage, a self contained tanning room (as is), and a water mitigation system installed and inspected annually by JES Foundation Repair. Bring your personal design ideas to the interior and modernize as you see fit. Outside, enjoy your privacy on the large back deck overlooking your .64 acre double lot! There is abundant space for gardening, play, entertaining and pets. If you have multiple vehicles, boats, lawn tractor equipment or just want a large workshop, be sure to tour the 28'x32' detached building. It's already equipped with 2 garage doors, power, concrete floor and tons of storage space! Enjoy easy, comfortable living with the benefits of a large yard and mountain views, but the convenience of downtown amenities 1 block away. Woodstock has incredible small town charm but is also half way between two major cities with their own culture, history and colleges; Winchester and Harrisonburg. With I-81 only 2 blocks away, both are a short drive. Schedule a showing today! Active security cameras inside the home.

1081 Hisey Ave, Woodstock

Listing courtesy of Preslee Real Estate. Contact: 5402274416

$510,000
5 Beds 4 Baths
A welcoming front porch sets the tone for this stately home—an inviting space to relax and enjoy the charm of the neighborhood. A beautiful stained-glass entry doorway makes a memorable first impression, opening to a grand staircase that serves as a stunning focal point. The main level offers a gracious parlor along with formal living and dining rooms, highlighted by long windows, rich heart pine and walnut flooring and original interior doors & hardware. The updated kitchen features granite countertops, wood floors, a skylight, and ample space for a work island. Just off the kitchen, a large screened porch overlooks the private, fenced backyard—perfect for morning coffee or evening gatherings. Also on the main floor, you’ll find a convenient powder room and a spacious primary suite complete with a private bath and generous closet space. Upstairs, a wide foyer leads to four generously sized bedrooms filled with natural light and complimented by warm wood floors. A second ensuite bedroom offers a connecting full bath and sitting area, plus another full bath and a separate laundry area adds everyday convenience. The cellar provides additional space for utilities and storage. Outside, the fenced backyard offers privacy and plenty of room for entertaining, pets, or peaceful outdoor enjoyment. Completing the property is a detached 20x24 two-car garage with electricity—ideal for vehicles, hobbies, or a workshop. Off street parking with asphalt drive, plenty of room to park when everyone's home or when entertaining. This just might be the home of your dreams, don't let it get away!

316 S Muhlenberg St, Woodstock

Listing courtesy of Johnston and Rhodes Real Estate. Contact:

$664,900
3 Beds 4 Baths
PRICE REDUCED! WELL BELOW TAX ASSESSEMENT OF $804,000 LARGE DETACHED GARAGE ADDED TO THIS LISTING 30 X 40 WITH 14' DOORS. Nestled on 6 beautiful acres, this stunning log home crafted with classic D-logs the perfect blend of rustic charm and modern comfort. Featuring 3 bedrooms and 3.5 baths, this spacious home is designed for both functionality and warmth. The main level master suite is thoughtfully designed to be wheelchair accessible, providing convenience and ease of living. Upstairs, you'll find two generously sized bedrooms, with their own private bath-ideal for family members or guests. The unfinished basement offers endless potential with lumber, doors, and trim already on site and ready to convey with the home - making it easy to customize and complete the space to suit your needs. A few small projects remain, giving you the opportunity to add your personal touch and truly make this home your own. Additional features include a two bay attached garage and the house has beautiful decking and under cover porches that would make a great patio area for your enjoyment. Detached garage is included with this 6 acres. Enjoy the surrounding acreage, whether you envision gardening, recreation, or simply soaking in the peaceful country setting. This property offers privacy, space and the timeless appeal of log home living-all waiting for your finishing touch. Strong natural spring on property. Sellers are willing to offer a credit to complete the master shower.

131 Upper Springs Ln, Woodstock

Listing courtesy of Johnston and Rhodes Real Estate. Contact:

$415,000
3 Beds 2 Baths
Price Improvement!! Motivated Seller!! Nestled in the charming Woodstock neighborhood, this exquisite Colonial home, built in 1901, offers a unique blend of historic elegance and modern potential. The home is 3 bedroom 2 bathroom , set on a generous 0.81-acre lot. The exterior, adorned with classic vinyl siding, exudes timeless appeal, while the private offstreet driveway ensures convenient parking for you and your guests. Imagine hosting gatherings in your spacious backyard, and large wrap around porch, where the possibilities for outdoor entertainment are endless. Directly across the private paved parking you can enjoy the separate shed equipped with large windows, openly spacious and working electricity! The shed is great for a private office space or workshop. Woodstock is renowned for its vibrant community spirit and proximity to local amenities. Enjoy leisurely strolls through tree-lined streets, where quaint shops and delightful eateries await. The neighborhood is a haven for those who appreciate a blend of tranquility and accessibility, with parks and recreational areas just a stone's throw away, perfect for weekend adventures or evening walks. This property is not just a home; it's a canvas for your dreams. With its rich history and prime location, it invites you to create a sanctuary that reflects your personal style. Experience the charm of Woodstock and the endless possibilities this Colonial gem has to offer. Don't miss your chance to make this enchanting residence your own!

10529 Old Court Rd, Woodstock

Listing courtesy of Weichert, Realtors - Integrity Home Team. Contact: (410) 449-3009

$438,000
Commercial Warehouse / Retail Building – 12,000+ SF | Prime Route 11 Frontage REDUCED PRICE Versatile commercial property offering over 12,000 square feet in a substantial building formerly operated as a building supply business. The main level features approximately 6,000 SF of large, open retail/showroom space, ideal for retail, showroom, or light commercial use, along with two private office rooms and two half bathrooms. (1 - on main level & 1-lower level) A newer heat pump system provides heating and air conditioning to most of the main level. The lower level offers an additional 6,000+ SF, including extensive storage shelving, another office space, and a drive-in loading door, making it well suited for warehouse, distribution, or storage operations. A loading dock on the second level adds further functionality for loading. There are (2) separate electric services. (2-accounts) The property includes two older oil furnaces(lower level and 2nd level of the bldg.), multiple additional storage sheds, and a parking area directly in front of the building. Located with excellent visibility fronting US Route 11 / North Main Street in the Town of Woodstock, this site offers strong exposure and accessibility

659 North Main, Woodstock

Listing courtesy of Sager Real Estate. Contact:

$550,000
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: (571) 921-9755

$549,000
4 Beds 2 Baths
This lovely Victorian greets you with it’s bold and commanding presence softened by perennial plantings for 4 seasons of beauty. A cheery original, ornate yellow door bids you welcome. Once inside, you’ll find that this home has been lovingly updated without compromising it’s beautiful character and charm. Original entrance columns, nine foot ceilings, hardwood floors, transoms over interior doors, lots of built-ins and a sweeping staircase are just a few of the quality features. Sunshine filters in through large windows and gas logs offer a cozy den to relax at the end of the day. A new and functional kitchen with upgraded counters, custom built cabinetry, massive island space and modern appliances are a cook’s dream. The dining room will easily seat an extended table and is tastefully decorated with wallpaper from days past. Showcase your treasured dishes in the built in cabinetry. The main level also includes the front parlor or the perfect at home office with custom built-in bookcases. A bath has been added for convenience to this main level. On the upper level you’ll find 4 bedrooms, full bathroom and laundry, plus those winding back stairs that are a shortcut to the kitchen. Did I mention the stairs to the attic? Use as storage or finish off for more living space! There’s even more to enjoy- stepping into the screened porch with hookups ready for a hot tub, and ample sized deck cut around a live tree offering shade during the summer. A detached garage, great for housing the mower or extra storage and private driveway are additional features. The partially fenced back yard offers both privacy and open space, including two raised garden beds ready for spring planting. The major components of this home have been updated such as vinyl siding, windows, HVAC system, and freshly painted roof and gingerbread trim. So make your move in 2026! Take in the scenic mountains and breathe in the country air, it’s waiting here for you.

207 S Muhlenberg St, Woodstock

Listing courtesy of Johnston and Rhodes Real Estate. Contact:

$985,000
Price reduction! Prime Investment Opportunity – Former assisted living facility strategically located in the beautiful Shenandoah Valley in Woodstock, VA just off Interstate I-81. This exceptional property offers a unique opportunity for investors and operators to establish a thriving senior living community, assisted living facility, Senior Day care or Child Day care, private school, church, dentist, shelter, apartments (SUP), physical rehab facility, professional office space, retail store, Animal Hospital (Vet Clinic), motel, restaurant or similar type business. Centrally located with easy access to healthcare facilities, shopping centers, and recreational amenities. Originally designed for assisted living with over 8600 sqft +/- layout, 16 large bedrooms (up to 32 residents), 11+ bathrooms, multiple spacious common areas, and well-designed living spaces perfect for a premier senior living community or commercial business. Potential for expansion of 8+ more rooms (16 additional residents) or the addition of complementary services, including memory care, physical rehabilitation, or specialized healthcare. Turn-key facility, all furniture, furnishings and equipment convey with purchase.

218 Mill Road, Woodstock

Listing courtesy of Cottonwood Commercial, LLC.. Contact: (540) 434-9922