Woodstock Homes for Sale

Woodstock Homes for Sale

Welcome to Woodstock, a charming town nestled in the heart of the stunning Catskill Mountains in upstate New York. Known for its vibrant arts scene, rich history, and breathtaking natural beauty, Woodstock is a haven for those seeking a serene lifestyle combined with a creative spirit. With its picturesque landscapes, quaint shops, and a welcoming community, it’s no wonder that many are looking to call this enchanting town home.

Woodstock boasts a diverse range of homes for sale, catering to various tastes and budgets. Whether you’re dreaming of a cozy cottage surrounded by lush greenery, a modern home with panoramic mountain views, or a historic property steeped in character, you’ll find it here. Each neighborhood exudes its own unique charm, from the bustling village center to the tranquil outskirts, offering something for everyone.

Outdoor enthusiasts will revel in the numerous recreational opportunities available, including hiking, biking, and exploring the nearby lakes and rivers. The town’s commitment to preserving its natural beauty ensures that residents can enjoy the great outdoors year-round. Additionally, Woodstock’s cultural offerings are second to none, with art galleries, live music venues, and festivals that celebrate the town’s rich artistic heritage.

With homes for sale in this idyllic location, now is the perfect time to discover the magic of Woodstock. Embrace the opportunity to live in a community that values creativity, nature, and a sense of belonging. Your dream home awaits in this captivating town where every day feels like a getaway.

Newest Woodstock Homes for Sale

$489,900
3 Beds ⋅ 2 Baths ⋅ VASH2015164 MLS
An Address Worth Waiting For… Welcome to Blessed Lane! Tucked away on a peaceful private road in the heart of the Shenandoah Valley, this beautifully maintained home offers the perfect blend of modern style, comfort, and breathtaking mountain views. Situated on approximately 0.84 acres with a wooded backyard, you’ll enjoy privacy, space to relax or play, and the beauty of nature—all while benefiting from the convenience of a private well. Step inside to soaring 12-foot vaulted ceilings that create a bright, open atmosphere perfect for everyday living and entertaining. The stunning kitchen features timeless white shaker cabinetry, abundant countertop space, bar-top seating, and a seamless flow into the spacious living and dining areas. The inviting living room is accented by a cozy electric fireplace, beautiful finishes, and large windows that fill the space with natural light. Just off the dining area, step onto the rear deck overlooking the private wooded backyard—the perfect place to enjoy your morning coffee or unwind in the peaceful surroundings. The main level offers a spacious primary suite complete with a walk-in closet and private en-suite bath, along with two additional bedrooms and a full guest bathroom. The lower level expands your living space with a dedicated theater room, home gym, two storage closets, and a large unfinished area ready to be customized to fit your needs—whether it’s a recreation room, workshop, additional living space, or extra storage. An attached two-car garage adds even more convenience. Outside, gather around the fire pit, enjoy the privacy of the wooded backyard, or simply relax while taking in the beautiful mountain views from the front of the property. Conveniently located just minutes from downtown Woodstock, shopping, dining, wineries, and endless outdoor recreation, this exceptional home offers the perfect balance of privacy, comfort, and convenience. Welcome home to Blessed Lane—where peaceful country living and modern comfort come together.

56 Blessed Ln, Woodstock

Listing courtesy of Realty ONE Group Old Towne. Contact: 5404592727
$1,149,999
5 Beds ⋅ 4 Baths ⋅ MDHW2071912 MLS
WOW! What a wonderful family oriented home for a lucky family to live in! The community of lovely Waverly Woods is close proximity to schools and commercial businesses. If you know this area, you will not hesitate to live here and enjoy this wonderful community. This home is a very friendly family entertainment wonderland. Not only does this house have all the amenities you expect inside but the outside backyard is a lovely area to entertain and watch your family grow with your neighbors as well. Inside on the main level you have lots of room to stretch for any size family. There is a superb and beautiful luxury gourmet kitchen & island, pantry, family room off kitchen with wood burning fireplace. When I say a family room I really mean a large family room. This is the meat of the main level area. Kitchen/family room and leave outside to this wonderful outdoor wonderland of an inground pool/heated/lighted/fire pit/table space/BBQ areas and sitting through, totally fenced and landscaped to give you privacy and luxury at the same time. The dining room is separate for those important or intimate dinners you want to share with loved ones or family units. The office/den in front of the home can possibly be used as another bedroom, but now it is a professional office. You can welcome your guest as they arrive inside to a lovely living room to discuss and just discuss away from other areas of the home. All the upper level bedrooms are large with windows and shades/blinds. The owner's bedroom is huge with a huge walk-in closet, upper self for decorations and a luxury bathroom with walk in shower. The laundry room is on the upper level with your washer/dryer for your convenience. In the basement you will find a wet bar/entertainment television area and half bathroom. The other area of the basement is your game/exercise room. Each area of the basement is very efficient in size and usage. The area by the wet bar is a double wide walk up to go to the backyard. I will say this house is the perfect home for that family who wants to watch your family grow older together. This home allows you to meet & greet your new neighbors and create new friends for your kids but you as well for a lifetime. Once you view this home you will say I REALLY FEEL THIS IS IT! I FOUND THE PERFECT HOME FOR MY FAMILY! You will not be sorry for viewing this home. The owners are still trying to get rid of furniture they do not want, but others to keep, for their older kids to remove what they want & rid too.

10405 Hardwood Ct, Woodstock

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$389,900
3 Beds ⋅ 3 Baths ⋅ VASH2015096 MLS
Located on the edge of town with beautiful mountain views, thoughtful updates, and a fully finished layout make this Woodstock home one you won't want to miss. One less worry for the new owner, the home will have carpets professionally cleaned as well as the home. Offering 3 bedrooms with the potential for a 4th, 3 full baths, and an open-concept design with vaulted ceilings, this home combines comfort and functionality. Step through the kitchen's double doors onto the new deck, creating the perfect space for entertaining or relaxing while enjoying the surrounding scenery. The spacious primary suite features a soaking tub, double vanity, and backyard view. The kitchen offers a large island with additional storage, a pantry, and plenty of room for a full-size dining table. Recent updates include a new roof (2022), heat pump (2020), hot water heater (2026), garage repair (2026), and new deck (May 2026). Have peace of mind with the big ticket items already done for you. Laundry room has shelving and utility sink. You'll enjoy easy access to downtown Woodstock's restaurants, bakeries, breweries, floral shops, theatre and local boutiques. Outdoor enthusiasts will appreciate nearby hiking trails, fishing, tubing, kayaking, wineries, vineyards, and all that the Shenandoah Valley has to offer. Conveniently located near shopping, local markets, and the Shenandoah County Fairgrounds, home to the county fair, concerts, and year-round community events.

505 S Water St, Woodstock

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$850,000
4 Beds ⋅ 5 Baths ⋅ MDBC2170074 MLS ⋅ Patapsco Homeowners Assoc BLDG.
Welcome to 2202 Siena Way, where timeless elegance meets peaceful country living on a breathtaking 2.47-acre homesite in the sought-after Woodstock area. Tucked away on a scenic lot with beautiful views, this impressive stone-front colonial offers over 5,300 square feet of finished living space, combining generous room sizes with a warm, inviting layout perfect for everyday living and entertaining. The main level welcomes you with a grand foyer, formal dining room, private home office, and an abundance of natural light throughout. The spacious kitchen is the heart of the home, featuring granite countertops, a center island, ample cabinetry, and an adjoining breakfast area that flows seamlessly into the sunroom and expansive family room, complete with a stunning stacked stone fireplace. Upstairs, the luxurious primary suite provides the perfect retreat with a spa-inspired bath featuring a soaking tub, dual vanities, and plenty of space to unwind. Three additional generously sized bedrooms, a full hall bath, and the convenience of upper-level laundry complete the second floor. The fully finished walkout lower level offers exceptional flexibility with an expansive recreation room, theater or media room, den, and a potential fifth bedroom, making it ideal for guests, multi-generational living, or creating the ultimate entertainment space. French doors lead outside, extending your living area into the private backyard. Step outside to enjoy the oversized deck overlooking nearly two and a half acres of open space, where you'll find room to entertain, garden, play, or simply relax while taking in the peaceful surroundings. The attached two-car garage, mature setting, and desirable location offer the perfect balance of privacy and convenience, with easy access to major commuter routes, shopping, dining, and recreation. If you've been searching for a home that offers space, quality, and a serene setting without sacrificing convenience, 2202 Siena Way is ready to exceed your expectations.

2202 Siena Way, Woodstock

Listing courtesy of Hyatt & Company Real Estate, LLC. Contact:

$305,000
3 Beds ⋅ 2 Baths ⋅ VASH2015028 MLS
Located in the Orchard View subdivision of Woodstock, this charming home offers 3 bedrooms and 2 full baths across comfortable living spaces to include a spacious living room and separate dining room. Set on close to a half - acre lot, the property features a welcoming covered front porch and rear deck—perfect for morning coffee or evening relaxation. Located just minutes from Woodstock Park, pool, shopping and restaurants this home offers both tranquility and convenience.

424 Meghann Dr, Woodstock

Listing courtesy of Epique Realty. Contact: 8888933537
$975,000
5 Beds ⋅ 4 Baths ⋅ MDHW2071276 MLS
Set on 1.19 private acres, this spacious and elegant five-bedroom, 3.5-bath home offers approximately 3,664 finished square feet of beautifully appointed living space. The main level showcases a hardwood staircase, 9-foot ceilings, hardwood flooring, crown molding, and a warm, inviting family room featuring Palladian windows, an 11-foot ceiling, and a raised-hearth wood-burning fireplace. The gourmet kitchen is appointed with maple cabinetry, granite countertops, stainless steel appliances, a center island, and a spacious breakfast area. Step outside to the expansive deck, where peaceful surroundings create the perfect setting for relaxing or entertaining. A sunken living room, library, and formal dining room complete the main level. Upstairs, crown molding continues throughout, adding timeless elegance. The primary suite offers a true retreat with a cathedral ceiling, wood-burning fireplace, sitting room, and two walk-in closets. The recently renovated ensuite bath features Craftsman-style cabinetry, granite countertops, a freestanding soaking tub, frameless glass shower, and dual vanities connected by a center storage cabinet. Three generously sized secondary bedrooms, a hall bath, and a convenient laundry room complete the upper level. The recently finished lower level expands the home's living space with luxury vinyl plank flooring, a kitchenette featuring a full-size refrigerator, beverage refrigerator, sink, and walk-in pantry. This level also includes a spacious bedroom, full bath with generous counter space, a sitting area, abundant storage, and a walk-out basement with full-size windows that fill the space with natural light and scenic views. Additional highlights include a two-car garage, an architectural shingle roof installed in October 2021, dual-zone Carrier HVAC systems, an ADT professionally monitored security system, an active radon mitigation system, well and septic service, a whole-house water filtration and buffer system, and an impressive well yield of more than five gallons per minute. Conveniently located within the Waverly Elementary, Mount View Middle, and Marriotts Ridge High School districts for the 2026–2027 school year.

1646 Woodstock Rd, Woodstock

Listing courtesy of Keller Williams Realty Centre. Contact: 4103120000
$715,000
4 Beds ⋅ 4 Baths ⋅ MDBC2169268 MLS
Nestled in the serene enclave of Mardella Run, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Spanning an impressive 3,600 square feet, this home is designed to cater to both relaxation and entertainment, making it an ideal sanctuary for modern living. As you step inside, you are greeted by an inviting open floor plan that seamlessly connects the family room to the gourmet kitchen. The heart of the home features a spacious island, perfect for casual dining or culinary creations, complemented by a pantry for all your storage needs. The family room, adorned with a cozy fireplace, invites warmth and intimacy, while the formal dining room sets the stage for elegant gatherings. The main level also boasts a luxurious primary suite, complete with a walk-in closet and a spa-like bathroom featuring a walk-in shower. Skylights and recessed lighting throughout the home create a bright and airy atmosphere, enhancing the overall sense of space and tranquility. Venture to the fully finished basement, where endless possibilities await. This versatile area can serve as a recreation room, home office, or additional living space, complete with a rear entrance for convenience. Outside, the property is set on a generous 1.35-acre lot, providing ample space for outdoor activities and relaxation. Enjoy the fresh air on the screened deck, perfect for morning coffee or evening gatherings under the stars. The meticulously maintained exterior, featuring a classic brick façade, adds to the home's timeless appeal. Additional high-end features include a side-entry attached garage with space for two vehicles, ensuring both convenience and security. The home is equipped with modern appliances, including a dishwasher, refrigerator, and washer/dryer, making daily living effortless. Located in a tranquil suburban setting, this property offers the perfect balance of privacy and accessibility. Enjoy the peace of a spacious lot while being just a short drive from local amenities, shopping, and dining options. This home is not just a residence; it's a lifestyle choice that embodies comfort, elegance, and the joy of living well. Experience the charm and sophistication of Mardella Run, where every detail has been thoughtfully curated for your enjoyment.

21 Deep Powder Ct, Woodstock

Listing courtesy of Weichert, Realtors - Integrity Home Team. Contact: (410) 449-3009
$900,000
4 Beds ⋅ 4 Baths ⋅ MDHW2071162 MLS
** COMING SOON**

10310 Winstead Ct, Woodstock

Listing courtesy of Keller Williams Lucido Agency. Contact: (410) 465-6900
$395,000
3 Beds ⋅ 3 Baths ⋅ VASH2014942 MLS
Welcome to this spacious 3-bedroom, 2.5-bathroom home offering over 2,000 sq. ft. of living space and an entertainer’s dream backyard! Inside, you’ll find multiple living areas, including a bright living room, a cozy family room, and a dedicated office—perfect for remote work or hobbies. The dining room flows into a kitchen with ample cabinetry and counter space, making family meals and entertaining easy. Upstairs, the primary suite features a private en-suite bath, while two additional bedrooms share a convenient full bath. The lower level has a half bath. Enjoy an attached garage for parking and storage. Step outside to your outdoor paradise, complete with custom tiki bar with bar seating, stone patio, string lighting for a perfect evening vibe, and a hot tub for year-round relaxation. This backyard has everything you could need! All this, located in a quiet neighborhood near downtown Woodstock, schools, the Seven Bends State Park and shopping. Schedule your private tour today! Sellers have an assumable VA mortgage at 4.7%. Contact listing agents for more details.

714 Jackson St, Woodstock

Listing courtesy of Realty ONE Group Old Towne. Contact: 5404592727
$585,000
4 Beds ⋅ 4 Baths ⋅ VASH2014876 MLS
Every once in a while, a home comes along that truly stands apart. Beautifully updated and impeccably maintained, this magazine-worthy home offers three finished levels, timeless finishes, and a resort-style backyard on a quiet cul-de-sac in one of Woodstock's most desirable neighborhoods. The light-filled main level is designed for both everyday living and entertaining with rich hardwood flooring, elegant trim work, a private office, formal dining room, welcoming sitting room, and spacious family room with a cozy gas fireplace. The gourmet kitchen features granite countertops, refinished cabinetry, a large center island, double wall ovens, gas cooktop, pantry, and an open layout that keeps everyone connected. Upstairs, the spacious primary suite offers dual walk-in closets and a spa-like bath with soaking tub, walk-in shower, dual vanities, and skylights. Three additional bedrooms and another full bath complete the upper level. The finished walkout basement provides exceptional flexibility with a large recreation room, finished bonus room, full bath, and private exterior entrance, making it ideal for guests, a home gym, media room, or multigenerational living. Outside, your private backyard retreat awaits with a heated in-ground Kayak pool, covered patio, beautiful landscaping, seasonal mountain views, and nearly half an acre to enjoy. Recent improvements include a new roof (2024), new gas range (2024), new HVAC (2022), expanded hardwood flooring, and fresh interior paint. This is more than a beautiful home...it's a lifestyle.

465 Meghann Dr, Woodstock

Listing courtesy of Preslee Real Estate. Contact: 5402274416
$675,000
3 Beds ⋅ 3 Baths ⋅ VASH2014662 MLS
Welcome Home! Immaculate brick home on a quiet street just outside of town! Meticulously maintained inside and out. Enjoy your morning coffee in the sunroom or poolside. Main level Master Bedroom. Two upper level bedrooms, bath, office and unfinished storage space. Two (2) fireplaces, one pellet, one gas logs. Four (4) zone hot water baseboard heat. Access basement storage space and shelving from garage. Attached and detached garages plus carport. Fenced pool, depth 3.5 to 6.5 feet with storage building.

908 Jonathan St, Woodstock

Listing courtesy of Johnston and Rhodes Real Estate. Contact:

$379,900
3 Beds ⋅ 2 Baths ⋅ VASH2014860 MLS
Perfect full-time residence or weekend getaway. The front door leads straight into the open-concept living room and kitchen space. The kitchen is bright with white cabinetry, granite countertops, and an island. The master suite features a walk-in closet and an ensuite bath with double bowl sinks. Vinyl plank flooring runs throughout. Recent upgrades include a paved driveway, outbuilding, back deck with an awning and handrailing, electric fireplace, and decorative landscaping. Nestled among mature trees with stunning mountain views, this property is pure Shenandoah Valley. Community access to the North Fork of the Shenandoah River - among the famous "Seven Bends"!

58 Cedar Ln, Woodstock

Listing courtesy of Skyline Team Real Estate. Contact:

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