Woodstock Real Estate

Woodstock Real Estate

Welcome to Woodstock, a charming town nestled in the heart of the picturesque Catskill Mountains in New York. Known for its vibrant arts scene and rich history, Woodstock is a haven for those seeking a blend of natural beauty and cultural experiences. Originally established as a hub for artists and musicians in the 1960s, this town has retained its creative spirit, making it a delightful destination for residents and visitors alike.

Woodstock is surrounded by stunning landscapes, including lush forests, serene lakes, and breathtaking mountain views, perfect for outdoor enthusiasts. The nearby Overlook Mountain offers hiking trails that reward adventurers with panoramic vistas, while the Ashokan Reservoir provides opportunities for fishing, kayaking, and picnicking. In winter, the area transforms into a snowy wonderland, ideal for skiing and snowshoeing.

The town itself boasts a quaint, walkable village center filled with unique shops, artisanal eateries, and galleries showcasing local artists. The iconic Woodstock Music Festival may have been in the past, but the spirit of community and creativity continues to thrive with year-round events, farmers' markets, and live music performances.

Families will appreciate the strong sense of community and the excellent local schools, making Woodstock an ideal place to raise children. With a range of housing options, from cozy cottages to spacious family homes, there’s something for everyone in this enchanting town.

Whether you're seeking a peaceful retreat or a vibrant community, Woodstock offers a unique blend of nature, culture, and history that makes it a truly special place to call home. Explore the magic of Woodstock and discover your next dream home in this idyllic setting!

Newest Listings in Woodstock

$385,000
2 Beds ⋅ 2 Baths
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

Listing courtesy of Jack Cooper Realty. Contact:

$325,000
3 Beds ⋅ 1 Baths
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

Listing courtesy of Funkhouser Real Estate Group. Contact: 5404594002
$489,900
3 Beds ⋅ 2 Baths
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
$389,900
3 Beds ⋅ 3 Baths
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:

$749,000
3 Beds ⋅ 3 Baths
Welcome to 10779 Folkestone Way! Filled with natural light and thoughtfully updated, this beautiful end-of-group townhome offers spacious living, timeless finishes, and numerous recent improvements. The inviting main level features 9-foot ceilings, a formal living room with columns separating the elegant dining room accented with crown molding and chair rail, refinished hardwood floors (2022), and new recessed lighting that enhances the bright, open feel. Oversized windows, many accented with transoms, are complemented by custom shutters and blinds throughout. The well-appointed kitchen offers 42-inch cabinetry, granite countertops, a pantry, and a convenient Butler's Pantry connecting the kitchen and dining room. There is plenty of space for everyday dining in the breakfast room, while the adjoining family room features crown molding, a charming walk-in bay window, and sliding glass doors leading to the new composite deck (2023)—perfect for relaxing or entertaining. Upstairs, the primary suite provides a peaceful retreat with a vaulted ceiling, ceiling fan, walk-in closet, and a versatile sitting room ideal for a home office, reading nook, or exercise space. The en-suite bath features a vaulted ceiling with a skylight, dual vanities, a soaking tub, and a separate shower. Two additional bedrooms, a full hall bath, and a convenient second-floor laundry area with a linen closet complete the upper level. The finished lower level expands the home's living space with luxury vinyl plank flooring (2022), a large recreation room featuring a cozy gas fireplace, full-size windows, and sliding glass doors opening to a brick paver patio. A separate bonus room offers endless flexibility as a home office, guest room, fitness area, playroom, or additional storage. The lower level also includes a partially finished bathroom with a full rough-in, providing the opportunity to easily add another full bath. Additional highlights and improvements include a two-car garage with extra storage space and a side exterior entrance, a new architectural roof (2018), replacement windows and front door (2012–2016), a dishwasher and microwave (2021), a refrigerator (2022), and much more—see the attached list for a complete summary of improvements. With quality updates already completed, this move-in ready home combines comfort, style, and exceptional value. Residents of the highly desirable Waverly Woods community enjoy an abundance of amenities, including an outdoor pool, clubhouse, tot lot, playground, recreation courts, scenic common areas, Waverly Woods Golf Club, and the nearby Waverly Woods Shopping Center with restaurants and everyday conveniences. Ideally located just minutes from major commuter routes, Historic Ellicott City, and Patapsco Valley State Park, this home offers the perfect blend of convenience, recreation, and lifestyle.

10779 Folkestone Way, Woodstock

Listing courtesy of Cummings & Co Realtors. Contact: 4108230033
$850,000
4 Beds ⋅ 5 Baths
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
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
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
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
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

Listing courtesy of Keller Williams Lucido Agency. Contact: (410) 465-6900
$639,900
3 Beds ⋅ 4 Baths
Don't miss this spacious, beautifully maintained 3-bedroom, 3 full bath, and 1 half bath townhouse in the highly sought-after Woodstock community. This larger model features a desirable three-level bump-out, creating additional living space and an open, inviting floor plan complete with a cozy gas fireplace. The main level boasts hardwood flooring throughout, a spacious living room, and a gourmet kitchen featuring new quartz countertops, new appliances, a breakfast bar, and abundant cabinetry—perfect for everyday living and entertaining. Thoughtful recent updates include fresh interior and exterior paint, new carpeting, refreshed landscaping, a new CertainTeed roof with a transferable warranty, and an Energy Star hot water heater installed in 2022, providing added value and peace of mind. Enjoy exceptional community amenities, including a swimming pool, clubhouse, and playground. Ideally located just minutes from shopping, dining, and major commuter routes, this home offers the perfect combination of comfort, convenience, and style.

10727 Hillingdon Rd, Woodstock

Listing courtesy of Samson Properties. Contact: 7033493900
$575,000
4 Beds ⋅ 4 Baths
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
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