Woodstock Real Estate

Woodstock Real Estate

Welcome to Woodstock, a charming town nestled in the heart of the scenic Catskill Mountains in New York. Known for its vibrant arts scene, rich history, and breathtaking natural beauty, Woodstock is a place where creativity flourishes and community thrives. With a population of just over 6,000 residents, this quaint town offers a perfect blend of small-town charm and cultural vibrancy.

Woodstock is perhaps best known as the site of the legendary 1969 music festival, which forever linked it to the counterculture movement. Today, the town continues to celebrate its artistic roots, boasting numerous galleries, studios, and live music venues. The iconic Bearsville Theater and the Woodstock Playhouse host a variety of performances, making it a hub for entertainment and creativity.

Nature enthusiasts will find their paradise here, with miles of hiking trails, picturesque waterfalls, and ample opportunities for outdoor activities. The nearby Catskill Park offers stunning landscapes, perfect for hiking, camping, and exploring. In autumn, the region transforms into a kaleidoscope of colors, attracting visitors for leaf-peeping and outdoor adventures.

Woodstock’s charming downtown area features unique shops, cozy cafes, and farm-to-table restaurants, making it an inviting destination for locals and visitors alike. The community is known for its friendly atmosphere and commitment to sustainability, with local farmers' markets and eco-friendly initiatives.

Whether you're seeking a peaceful retreat, an artistic haven, or a vibrant community, Woodstock offers a unique lifestyle that captures the essence of New York's natural beauty and cultural richness. Come explore this enchanting town and discover why so many have chosen to call Woodstock home!

Newest Listings in Woodstock

4 Beds ⋅ 4 Baths

Wake up to stunning, panoramic golf course views right from your bedroom window. Nestled in a premier age-restricted 55-and-older community, this extraordinary home perfectly blends luxury, low-maintenance living, and a vibrant community lifestyle. Enjoy premium neighborhood amenities including a clubhouse, fitness center, outdoor pool, EV charging stations, and tennis, pickleball, and bocce courts. The prime location offers the perfect balance of recreation and convenience. The home is minutes from the shopping, dining, and daily conveniences at Waverly Woods Village Center, as well as the local boutiques in historic Olde Ellicott City, Downtown Columbia, and concerts at Merriweather Post Pavilion. Outdoor recreation is easily accessible at Centennial Park and Patapsco Valley State Park. Traveling and commuting are effortless with quick access to Interstate 70 and Routes 29, 40, 100, and 95. Don’t miss your chance to own this truly special property where golf course views, an unbeatable location, and community living come together in perfect harmony. Some photos are virtually staged.

11064 Chambers Ct Unit #122, Woodstock

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

3 Beds ⋅ 2 Baths

This is your opportunity to own a Beautiful home in Hisey Park. A place to simplify your lifestyle without giving up comfort, space, or convenience. This home features three bedrooms with two baths, granite countertops, all on one-easy level. If you're ready to downsize, planning for retirement, or simply tired of dealing with maintenance or stairs, then this is the one for you. New Appliances were installed in 2024 & come with a transferrable warranty until 2029, The Water Heater was installed in 2025, Mowing & Snow Removal are paid until 12/31/2026. Come view this low-maintenance property, relax on the Patio, take in the wildlife, the mature landscaping and imagine it as Home!

1023 Sun Poppy Ct, Woodstock

Listing courtesy of ERA Valley Realty. Contact:

3 Beds ⋅ 3 Baths

Beautifully maintained split foyer home nestled in the desirable Orchard View community. It features 3 spacious bedrooms, 3 full bathrooms, and a 2-car garage. Step inside to find stunning hardwood floors throughout the main living areas, plus crown molding and recessed lighting that create an inviting atmosphere. The heart of the home is the country-style kitchen, featuring modern appliances including a built-in microwave, dishwasher, and electric range, making meal prep a delight. Enjoy casual dining in the eat-in area or host gatherings in the family room that seamlessly connects to the kitchen. The primary suite features a spacious bath and a large walk-in closet. The fully finished basement is ideal for entertaining or relaxing, with convenient access to the garage. Outside, you enjoy the new deck overlooking serene wooded views, perfect for morning coffee or evening gatherings. In a vibrant community, residents enjoy nearby parks and community amenities. With a spacious 0.53-acre lot, this home offers both tranquility and convenience, making it a perfect place to create lasting memories.

605 Cedar Ct, Woodstock

Listing courtesy of Samson Properties. Contact: 7033788810

4 Beds ⋅ 2 Baths

Welcome home to this beautifully RENOVATED Cape Cod offering modern comfort, classic charm, and ideal location in the heart of Woodstock, Virginia. Featuring an inviting open floor plan, this spacious home offers four bedrooms and two full baths, providing plenty of room for family, guest, or a home office. The thoughtfully updated interior creates a bright, welcoming atmosphere with an easy flow between the living, dining, and kitchen areas- perfect for everyday living and entertaining. A large full unfinished basement provides abundant storage and tremendous potential for future living space, a workshop recreation area, or whatever best suits your needs. Step outside and enjoy the large covered deck, an ideal spot for morning coffee, outdoor dining, or entertaining family and friends while taking in the beautiful mountain views. The expansive backyard offers plenty of room for gardening, recreation, pets or simply relaxing and enjoying the outdoors. Located in town and close to the town park and all of Woodstock's amenities, this home combines the convenience of being near shopping, dining, recreation and community activities with the peaceful beauty of the Shenandoah Valley.

358 W Spring St, Woodstock

Listing courtesy of Johnston and Rhodes Real Estate. Contact:

2 Beds ⋅ 2 Baths

Welcome to this pristine garden-style condominium in the highly sought-after Enclave at Waverly Woods subdivision in Howard County. Discover elevated living in this pristine, top-floor garden-style condominium. Beautifully well maintained and move-in ready, this 2-bedroom, 2-full-bathroom residence features stunning luxury vinyl flooring throughout the main living areas, offering both style and durability. The bright, open-concept floor plan maximizes natural light, highlighting a spacious living and dining room combo that flows seamlessly into an inviting eat-in kitchen. Step out onto your private, screened-in porch to enjoy peaceful, scenic views of the golf course and pond. The primary suite offers a true retreat with custom closets and a private attached bathroom. This residence is packed with convenience, featuring full-sized in-unit laundry, an assigned parking space in the secure underground garage. Located in a top-rated school district, this home offers an unbeatable lifestyle with resort-style community amenities, including an outdoor pool, fitness center, and proximity to excellent shopping, dining, and major commuter highways.

2111 Ganton Grn Unit #E308, Woodstock

Listing courtesy of Realty 1 Maryland, LLC. Contact: 410-707-7448

Turnkey 5-unit multifamily investment in the heart of Woodstock, offering stable rental income from day one. Multiple new HVAC systems and hot water heaters help keep upfront capital expenses to a minimum. All five units sit on one tax parcel with one address to manage, ample off-street parking, and public water and sewer. Tucked away among mature trees, the property offers a surprisingly private and secluded setting while still being within walking distance of downtown Main Street and convenient to I-81. An ideal opportunity for a hands-on investor or a smooth handoff to professional management. Rent roll and financials available upon request. Property is priced under current appraisal.

210 E Locust St, Woodstock

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com

3 Beds ⋅ 3 Baths

This charming Colonial home in Wellington Estates offers a perfect blend of comfort and modern living. With 3 spacious bedrooms and 3 full bathrooms, this residence boasts an open floor plan that invites natural light throughout. The heart of the home features a well-appointed kitchen equipped with stainless steel appliances, including a built-in microwave, dishwasher, and stove, making meal prep a delight. The main floor laundry adds convenience to your daily routine. Major renovations in 2022 have revitalized this home, ensuring it meets today's standards while maintaining its classic appeal. Enjoy cozy evenings in the inviting living spaces, or step outside to your expansive 0.53-acre lot, complete with a beautifully landscaped front yard and serene rear yard, perfect for outdoor gatherings or quiet moments in nature. The attached oversized garage and paved driveway provide ample parking and storage options. With views of the lush garden and lawn, this home is a peaceful retreat. Located in a vibrant community, residents benefit from nearby parks, excellent schools, and convenient public services. Explore the local amenities that make Wellington Estates a desirable place to call home. This property is not just a house; it's a place where memories are made and cherished. Experience the warmth and comfort that awaits you!

816 Burgess Ct, Woodstock

Listing courtesy of Kathy Jean Campbell. Contact: 5407176970

3 Beds ⋅ 3 Baths

Welcome to this beautifully upgraded townhouse offering 1,872 square feet of living space! Beautiful Northwood LVP flooring throughout the main level. The kitchen features quartz countertops, $500 upgraded backsplash, white cabinetry, and a gas range. Upstairs, you'll find three generously sized bedrooms, including a primary suite complete with a walk-in closet and private ensuite bathroom. A spacious linen closet in the upstairs hallway adds even more convenient storage, along with new shelving throughout all closets. The home has had significant upgrades, including a stunning $20,000 handicap-accessible walk-in shower with stone walls, and $7,000 Stainmaster upgraded carpet. Dual A/C and heating system. Additional features include a single-car attached garage, a laundry station, and a shed in the backyard for extra storage. Move-in ready. Schedule your tour today!

268 Parkside Ct, Woodstock

Listing courtesy of Skyline Team Real Estate. Contact:

4 Beds ⋅ 4 Baths

** Offer deadline set for 9/14 at 6pm ** Set on over five private acres in sought after Woodstock Ridge Estates, this Craftsman style farmhouse offers a picturesque wooded retreat surrounded by mature trees and abundant wildlife. Brick pillars with lights welcome you home along the long driveway, setting the tone for this special property. Step onto the inviting front porch and inside to an open dining area and spacious living room anchored by a beautiful brick fireplace. Large glass doors frame the peaceful wooded views and lead to the expansive Trex deck and screened gazebo; an ideal setting for relaxing, entertaining, or simply enjoying the scenery. The updated kitchen blends character and function with white cabinetry, updated countertops (2025), stainless steel appliances including a Sub-Zero refrigerator, and a second fireplace. A convenient powder room completes the main level. Upstairs, you'll find three bedrooms and two beautifully renovated full baths (2023). The spacious owner's suite features double door access to a private balcony overlooking the gazebo and wooded grounds, along with its own ensuite bath featuring a double sink vanity. The walkout lower level adds even more flexible living space with a fourth bedroom, wood burning stove, room for a second living or recreation area, and ample storage. Step outside to the bluestone patio and take in the peaceful natural surroundings. Additional highlights include a two car attached garage, Pella windows with integrated blinds, a new roof (2025), boiler (2025), water heater (2023), plus a separate barn and shed. With more than five acres to explore, this property offers space to hike through the woods, mountain bike, enjoy wildlife, or simply unwind in your own private retreat—all while enjoying the charm and community of Woodstock Ridge Estates.

10367 Cavey Ln, Woodstock

Listing courtesy of The KW Collective. Contact: 4435741600

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

3 Beds ⋅ 2 Baths

10832 Summit Ave, Woodstock

Listing courtesy of Northrop Realty. Contact: 4104651770

Large lot with trees and road frontage. Close to Woodstock, with shopping, schools, and services nearby. Private and quiet.

Mill Road, Woodstock

Listing courtesy of George W. Glaize, Jr., Inc. REALTOR. Contact: 540-662-5058

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