Woodstock Homes for Sale

Woodstock Homes for Sale

Welcome to Woodstock, a charming town nestled in the heart of the beautiful Catskill Mountains in New York. Known for its vibrant arts scene and rich history, Woodstock offers a unique blend of small-town charm and cultural sophistication. This picturesque town is surrounded by lush forests, serene lakes, and breathtaking mountain views, making it a haven for nature lovers and outdoor enthusiasts alike.

Woodstock is not just about stunning landscapes; it’s also a community brimming with creativity. The town has been a beacon for artists, musicians, and writers since the 1960s, and you can still feel that artistic spirit today. From local galleries to lively music festivals, there’s always something happening in this vibrant town. The historic downtown area is lined with quaint shops, delightful eateries, and cozy cafes, perfect for leisurely strolls and community gatherings.

If you’re considering making Woodstock your home, you’re in luck! The real estate market here offers a diverse array of homes for sale, ranging from charming cottages and modern retreats to spacious family homes. Whether you’re looking for a peaceful getaway or a permanent residence, Woodstock has something to suit every lifestyle and budget.

Imagine waking up to the sounds of nature, sipping coffee on a sun-drenched porch, and exploring the endless outdoor activities right at your doorstep. With its welcoming community, rich culture, and stunning scenery, Woodstock is not just a place to live; it’s a lifestyle waiting to be embraced. Discover your dream home in this enchanting town today!

Newest Woodstock Homes for Sale

$340,000
3 Beds ⋅ 2 Baths ⋅ VASH2015242 MLS
Welcome home to this charming brick ranch offering comfort, convenience, and beautiful country views! Ideally located just minutes from downtown Woodstock, you'll enjoy easy access to shopping, restaurants, medical facilities, schools, and parks while still appreciating the peaceful setting. This well-maintained home features 3 bedrooms and 1.5 bathrooms, including a primary bedroom with an attached half bath. The inviting interior offers engineered hardwood flooring throughout the main living areas, with cozy carpet in all three bedrooms. The updated kitchen boasts newer cabinetry, and recent improvements include a newer roof and a brand-new septic system, providing added value and peace of mind. The full unfinished basement is bright, spacious, and full of potential—perfect for creating additional living space, a recreation room, home office, or workshop to suit your needs. Take in the scenic pasture and mountain views from your own backyard and covered back patio. A convenient carport adds covered parking and pull down attic access. Whether you're looking for your first home, a place to downsize, or a property with room to grow, this delightful ranch offers the perfect combination of comfort, updates, and an unbeatable location.

538 Mill Rd, Woodstock
$340,000
1 Beds ⋅ 2 Baths ⋅ VASH2015240 MLS
This one-of-a-kind home in an established Woodstock neighborhood doesn't become available often! Everything is on one floor, but there is a full, mostly finished, basement for additional living and storage space. Your creative side will be happy with the large detached studio in the home's sizeable back yard. It has electricity and AC and sits under one of several mature shade trees. Convenient to the hospital and medical offices, this home offers a stacked stone living room fireplace, a bright kitchen and a sunroom with a classic Valley view. The sunroom is open to additional living or office space. A few steps away is the all tile hall bath, and the Primary bedroom with an ensuite bath, also all tile and offering a newer step-in shower. And, did we mention the laundry is also on the mail level? This home was built in the 1950's and shows it's quality construction throughout. It has some updates, including newer windows and has been well maintained. The living space, the central location and the price, make this a value worth considering!

208 N Muhlenberg St, Woodstock
$325,000
3 Beds ⋅ 1 Baths ⋅ VASH2015204 MLS
This charming 1962 ranch-style home offers a solid investment opportunity with its classic brick exterior and spacious 0.31-acre lot. Featuring three cozy bedrooms and a full bathroom, this property is perfect for those looking to add value through updates or renovations. The unfinished basement provides ample storage or potential for additional living space. The kitchen comes with essential appliances, including a built-in microwave, single oven, cooktop, and refrigerator, making it move-in ready for tenants or future buyers. Gas fireplace in the inviting living area, perfect for creating a welcoming atmosphere. Harwood floors throughout. With a paved driveway and close proximity to the Woodstock Town Park/Pool. The outbuilding with electric and electric baseboard heat offers additional storage or workspace. Come make this brick rancher yours!

410 W North St, Woodstock
$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
$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
$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
$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
$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
$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
$900,000
4 Beds ⋅ 4 Baths ⋅ MDHW2071162 MLS
Elegant Colonial nestled on a cul-de-sac in sought-after Waverly Woods, featuring a freshly painted exterior (2026), an updated driveway (2022), and beautifully maintained living spaces enhanced by custom crown molding and a timeless traditional floor plan. Additional updates include an HVAC system replaced in 2023, several windows replaced in 2026, and a roof inspection completed in 2025, providing added peace of mind. // Step inside the hardwood foyer, which opens to the formal living room, gracefully defined by elegant columns, before flowing seamlessly into the formal dining room highlighted by bay windows and a classic chandelier, creating an ideal setting for entertaining. // The spacious eat-in kitchen is thoughtfully appointed with granite countertops, white cabinetry, ceramic tile flooring, a pantry, and a peninsula with breakfast bar seating. Stainless steel appliances include a refrigerator updated in 2024 and a stove, cooktop, and microwave replaced in 2021. An adjoining breakfast room provides casual dining space and direct access to the deck for effortless indoor-outdoor living. // Open to the breakfast room, the inviting family room offers plush carpeting and a painted brick wood-burning fireplace that serves as a warm and welcoming focal point. A conveniently located powder room completes the main level. // Upstairs, the owner's suite provides a relaxing retreat with a tray ceiling, a walk-in closet, and a beautifully remodeled ensuite bathroom featuring a dual-sink vanity, a glass-enclosed shower, and a private water closet. Three additional generously sized bedrooms, all with carpeting, share a second full bathroom that was tastefully updated in 2021. // The fully finished walk-out lower level expands the home's living space with a dedicated theater room accessed through French doors, a versatile bonus room ideal for guests, a home office, fitness room, or hobby space, a full bathroom updated in 2021, and a separate storage room. // Outside, discover your own private backyard oasis. A spacious two-tier deck overlooks the beautifully landscaped, fully fenced yard, complete with a patio surrounding a heated lagoon-style in-ground pool with a built-in spa, a fire pit area perfect for gathering with family and friends, and a storage shed for added convenience. // Residents of Waverly Woods enjoy exceptional community amenities, including paths, playgrounds, a community pool, golf course access, and convenient proximity to shopping, dining, parks, commuter routes, and top-rated Howard County schools.

10310 Winstead Ct, Woodstock
$220,000
2 Beds ⋅ 1 Baths ⋅ VASH2014954 MLS
Welcome to this charming 2-bedroom, 1-bath ranch home situated on approximately 1.50 acres with beautiful mountain views and the ease of one-level living. Whether you're a first-time homebuyer, looking to downsize, or searching for a peaceful country setting, this property offers comfort, convenience, and room to enjoy the outdoors. Inside, you'll find a bright and inviting galley kitchen featuring white cabinetry with black hardware and a glass-door pantry for added character and storage. Step outside from the kitchen onto the rear deck, which leads down to a patio overlooking the expansive backyard—ideal for entertaining, gardening, or relaxing while taking in the surrounding scenery. Additional highlights include a new roof installed in 2022, a brand-new storage shed, and a large, level yard with plenty of space for outdoor activities. Enjoy the nice blend of country charm, mountain views, and move-in-ready convenience just minutes from the amenities of Woodstock and close to the interstate!

574 Kern Springs Rd, Woodstock
$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
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