Woodstock Real Estate

Woodstock Real Estate

Welcome to Woodstock, a charming town nestled in the picturesque mountains of the Catskills in New York State. Known for its vibrant arts scene and rich cultural history, Woodstock offers a unique blend of small-town charm and modern sophistication. With a population of just over 6,000 residents, this tight-knit community is a haven for artists, musicians, and nature lovers alike.

Founded in the 18th century, Woodstock gained fame as the site of the 1969 Woodstock Music Festival, which celebrated peace, love, and music. Today, the spirit of creativity continues to thrive, with numerous galleries, theaters, and live music venues dotting the landscape. The town hosts various cultural events throughout the year, including the renowned Woodstock Film Festival, drawing visitors from far and wide.

Nature enthusiasts will find a plethora of outdoor activities to enjoy, from hiking the scenic trails of the nearby Overlook Mountain to exploring the serene waters of the Ashokan Reservoir. The stunning landscapes change with the seasons, offering vibrant fall foliage, lush summer greenery, and winter wonderlands perfect for skiing and snowboarding.

Woodstock's downtown area is a delightful blend of eclectic shops, artisanal cafés, and farm-to-table restaurants, providing a warm and inviting atmosphere for residents and visitors alike. The local community is known for its friendly demeanor, making it easy to feel right at home.

Whether you’re seeking a peaceful retreat, a vibrant artistic community, or an outdoor paradise, Woodstock has something to offer everyone. Come discover the magic of this enchanting town, where every corner tells a story and every day brings new adventures.

Newest Listings in Woodstock

$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
$385,000
2 Beds ⋅ 2 Baths ⋅ MDHW2072182 MLS
Magnificent second-floor condo in a secure elevator building in sought-after Waverly Woods! This turn-key unit boasts brand-new carpet (July 2026), fresh paint, updated lights, and modern bedroom ceiling fans (July 2026). Enjoy an expansive open floor plan highlighted by recessed lighting, crown moldings, tray ceilings, and a cozy gas fireplace with access to the private screened-in balcony. The eat-in kitchen features ample cabinet storage, a pantry, brand-new GE gas range (July 2026), GE microwave (May 2025), garbage disposal (2022), and a Bosch dishwasher. The spacious primary suite offers a walk-in closet, double-sink vanity, and soaking tub, while the second bedroom features large closet space adjacent to a full hall bath. Dedicated laundry room includes an LG dryer, LG washing machine, replaced dryer vent (Nov 2024), and extra storage. EV chargers on-site! Key Updates: Water Heater (Nov 2020), 10-Yr Battery CO Alarm & Hardwired Smoke/CO Alarms (May 2021), Kenmore Elite Grab-N-Go Refrigerator w/ Ice Maker (Compressor under warranty, replaced 2021). Resort-style community amenities include a golf course, tennis courts, pool, splash pad, and playground. Unbeatable location near shopping, dining, Rt. 29, and I-70. Schedule your showing today!

2100 Ganton Grn Unit #B-205, 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
$679,900
3 Beds ⋅ 3 Baths ⋅ MDHW2071500 MLS
Welcome home to this exquisite end-unit townhome located in the coveted Waverly Woods community of Woodstock. Boasting a classic brick front and the convenience of a one-car garage, this property offers both striking curb appeal and everyday functionality. The interior is meticulously maintained and features gleaming hardwood floors that span all three levels of the home. This spacious residence is defined by its sought-after 3-level bump-out, which provides significantly more square footage and livability than standard models. The main level is an entertainer’s dream, featuring an open and inviting layout. The kitchen is a true centerpiece, complete with granite countertops and a large center island, which opens seamlessly into the expansive family room anchored by a warm, cozy fireplace. Outdoor living is equally impressive and designed for relaxation. Enjoy your morning coffee on the elevated, low-maintenance Trex deck, or escape to the finished walk-out basement, which leads directly to a private, charming brick patio—the perfect space for grilling and unwinding. The upper level provides a tranquil sanctuary, featuring 3 generously sized bedrooms and 2 full bathrooms. Ideally situated for both comfort and convenience in a premier community, this home is move-in ready and waiting for its new owners. Schedule your private showing today! UPGRADE LIST: ALL APPLIANCES(2019), ROOF(2019), WATER HEATER(2019), HVAC(2021)

10700 Croydon Ct, Woodstock
$640,000
3 Beds ⋅ 4 Baths ⋅ MDHW2071300 MLS
Welcome home to this stunning, brick-front townhouse in the desirable Woodstock community. The main level boasts an inviting open-concept layout that seamlessly connects the spacious family room, dining room, and kitchen—perfect for entertaining. The kitchen features sleek granite countertops, while a rear bump-out adds extra versatility and living space. Upstairs, you will find three generous bedrooms and two full bathrooms. The fully finished, walk-out basement adds incredible value with an additional room ideal for a guest suite or home office, a full bathroom, and a dedicated laundry area. Enjoy the beauty of newly installed LVP flooring throughout. This home also benefits from significant capital improvements: 2026 updates include fresh interior paint, new ceiling fans and light fixtures, a new HVAC system, New Carpet, New Luxury Vinyl Floor and renovated bathroom vanities/mirrors. With a roof replacement from 2023 and an updated water heater 2024, this property offers true peace of mind.

10806 Wadsworth Rd, 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
$335,000
2 Beds ⋅ 2 Baths ⋅ VASH2015026 MLS
Welcome to easy, one-level living in the desirable Grandview Estates community! This well-maintained duplex offers 2 bedrooms, 2 full baths, and a thoughtfully designed floor plan filled with natural light. The spacious living area flows seamlessly into the dining space and kitchen, creating the perfect layout for everyday living and entertaining. The primary suite features a private bath, while the second bedroom provides flexibility for guests or a home office. Enjoy peaceful mornings or relaxing evenings outdoors, along with the convenience of an attached garage and low-maintenance living. Ideally located just minutes from downtown Woodstock, shopping, restaurants, schools, Shenandoah Memorial Hospital, and I-81, this home offers comfort, convenience, and beautiful Shenandoah Valley living. Don't miss this wonderful opportunity

209 Kim Ct, 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
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