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Woodstock Homes for Sale

Woodstock New York Real EstateWoodstock homes for sale

While not home to the infamous Woodstock Festival, the town of Woodstock lended its name to the festival that was held roughly 60 miles away at Max Yasgur’s dairy farm. Only a 2-hour drive from New York City, Woodstock has become a popular destination for those looking to escape the hustle and bustle of city living, whether for a quick day trip or weekend getaway. The town of Woodstock is often known for its stunning art scene, in addition to a love for music and theater, all of which have helped Woodstock evolve into the stunning artsy community that you see today.

Home to less than 6,000 residents, Woodstock is a tight-knit community where residents can truly enjoy the perks of a simple life amongst the beauty of the Catskills. Dozens of different trails wind through the outskirts of Woodstock, with trails for those of all ages and skill levels, in addition to an abundance of additional recreational activities, allowing residents as well as tourists to enjoy the abundance of natural beauty that surrounds the town. The Ashokan Reservoir can be found just a mile to the south, creating a stunning backdrop as well as additional recreational offerings to enjoy.

The name Woodstock makes many people think of the 1970s. Woodstock is an incredible place to visit in the New York Catskills region. There are plenty of shops, restaurants, and amenities to make for a great vacation destination or even a place to call home. This place is rich in history and bohemian influence.

Things To Do In Woodstock

There are so many incredible boutiques to visit while in the Catskills. One of the favorites is THree Turtle Doves in Woodstock. If you love outdoor adventure then you have to check out Overlook Mountain. The trailhead is about ten minutes from town and the trail loop takes about 3 hours from start to finish. When you reach the tip you can look out to see gorgeous mountains and a 360-degree view. The hike is a gravel path which makes it accessible year-round during all of the seasonal changes. If you are looking for another trail check out the Huckleberry Point Trail in Elk Park. If you want a slower-paced relaxing activity, check out Glo Spa for all of your facials or massages.

Woodstock Schools

If you live in Woodstock and have school-age students, they will attend school at the Onteora Central School District. This district serves students in kindergarten through 12th grade. Students at Onteora Central School District get a well-rounded education with academic excellence and great extracurricular opportunities.

The district's mission statement for all of its students is, "Our Onteora schools exist to educate and nurture the children of our diverse community.  Our mission is to create an engaging and healthy learning environment that empowers all students to pursue their dreams, achieve their goals, and contribute thoughtfully to the global community."-Onteora Central School District.

Woodstock Real Estate

Woodstock offers a place for many to enjoy a slower-paced and peaceful atmosphere away from New York City. In Woodstock, you can find single-family homes that are great for those who desire a full-time residence or a vacation rental for potential passive income. The Catskills are a popular area for many, so it can be a wonderful investment for you. Woodstock can truly give you the escape you have been looking for while stepping into a piece of history.

What Locals Say About The Area

"I grew up in Woodstock and left 25 years ago, living in major cities since. My family and I live in NYC. We bought a weekend house in Woodstock last year and spend a good amount of time in Woodstock. Many of the local stores are the same as when I grew up, mostly privately owned. Although there are limited shopping options, the quality is good. Sunrise Market and Sunfrost Farms have had quality organic selections well before it was a trend. Nature is beautiful. It's not grand but that adds to the charm. Happy that my kids can experience nature and run around. Overall the people in Woodstock are friendly. There is, and always has been a NYC influence; there is a level of sophistication one might not find in other small towns. It was a great place to grow up and is an enjoyable place to be as an adult"-Niche

In Conclusion

To learn more about relocating to Western Catskills or any Catskills real estate, contact our office at any time. We would love to assist you with any real estate needs whether it is buying, selling, or investing.

image by Leah Jones

Woodstock Homes for Sale

$2,430,000
4 Beds ⋅ 6 Baths ⋅ 153734 MLS
Happy Brooks, the Graceland of 1960's counter culture, is waiting for you!Home to Woodstock Festival co-founder and legendary music industry icon Michael Lang for 45 years, this Mt. Tremper compound boasts a pedigree that dates back to the 1920s. Originally built for the artist G. Adolph Anderson, the 17 acre estate features three architecturally significant structures made from stone, wood & imagination.Entering the primary residence is to step into history. The stunning double-height great room with balcony has played host to renowned artists through the decades. In this wing you will find an office, two powder rooms & upper level bedroom and library. Past a massive bluestone fireplace, a central foyer leads into a formal dining room with mountain views, a cooks kitchen, and an open-plan family room with another fireplace w/ wood stove & built-in bread oven with views across the pergola-covered patio just outside French doors. A light-filled hallway will take you to 3 oversized bedroom suites, including a romantic primary, as well as a reading room found behind magnificent stained glass doors. Connecting this wing of the home is a spectacular conservatory within a 24-foot glass ceiling.Across the central courtyard framed by a mature birch tree is a 2 BR guesthouse that holds design treasure. An oversized living room leads into a den w/bluestone fireplace and a striking built-in collection of Fu dogs and wood-carvings on gilded plaques collected from travels to China that depict an epic story. The third stone structure is a 2BR fully-outfitted & stylish cottage, and is connected to a three-bay garage and a greenhouse ready to be restored or turned into a Romanesque walled garden. Additional structures include a tool shed and 3 stall barn, as well as a picnic pavilion with views of Slide Mountain, the tallest peak of the Catskills.The compound is truly park-like, with paths, stone walls, orchards, wildflowers and a centerpiece large pond with its own art island showcasing a sculpture by Michael Lang. On summer days you can enjoy a swim in the 53 x 40 oval lined cement pool while gazing at the mountains in the distance. Mt.Tremper is a special community just minutes from both Woodstock and Phoenicia.Happy Brooks, only two hours from NYC is the perfect place to gather and soak up the history that flows from every bit of this legendary estate.

Wittenberg Road, Woodstock
$1,095,000
4 Beds ⋅ 3 Baths ⋅ 152064 MLS
Experience peace and serenity in this spacious and airy 4-bedroom, 3-bath home, offering nearly 3,000 square feet of living space in a tranquil, private setting with breathtaking backyard mountain views. The home features unique handcrafted woodwork, a stunning fireplace, vaulted ceilings, an abundance of windows and skylights, exposed beams, and several updates. Whether you're in search of a weekend retreat or a full-time residence, this property is the perfect fit and just a short drive to the village of Woodstock. The open yet divided main floor plan provides fantastic entertaining options and cozy areas to unwind. The living room fireplace is a beloved focal point for the current owners. The ground-floor primary suite includes an updated bath, dual walk-in closets, and its own access to the back yard. Additionally, the first floor offers a second bedroom and full bath, along with a bonus flex room with a separate entrance off the garage - a versatile space for a home office, music studio, rec room, or whatever you can imagine. On the second floor, you'll find 2 more bedrooms (one with its own new balcony) and a shared full bath. The screened-in porch and new back deck with covered and open areas provide the perfect spots to relax and take in the surroundings. Outdoor amenities include deer fencing, a fire pit, outdoor stone fireplace, and a tree house, offering plenty of opportunities for play, entertainment, relaxation, and enjoyment. It will be a great summer here in Woodstock!

7 Woodstock Ridge Road Road, Woodstock
$450,000
3 Beds ⋅ 2 Baths ⋅ 151885 MLS
Welcome to this beautifully updated ranch-style home located just minutes away from downtown Woodstock. This property offers both convenience and tranquility, making it the perfect place to call home.This well-maintained home features a spacious layout, offering a total of 1,485 sq ft of living space. The single level ranch includes a large comfortable living room, a fully equipped kitchen, a dining area, 2 bathrooms one with a shower and tub the other features a shower, family room, dining room, three bedrooms, mudroom, new back deck (2023), and one car garage.The family room faces the backyard and features a cozy pellet stove, providing additional warmth during the winter months. It's the perfect spot for relaxation and quality time with loved ones.This house has undergone many recent upgrades, including new flooring throughout, Whirlpool appliances in the kitchen, a washer and dryer, a storm door, blinds, bathroom vanities, a hot water heater, a new septic system, a new leach field, gutters, and much more. These modern upgrades ensure a comfortable and contemporary living experience.Situated on a generous lot of 0.53 acres, this property offers plenty of outdoor space for relaxation and recreation. The well-manicured yard is perfect for gardening or hosting outdoor gatherings. Additionally, the one-car garage provides convenience and protection for your vehicle or personal items.The location of this home is truly ideal. Enjoy the peacefulness of the surrounding nature while still being within close proximity to the vibrant downtown areas of Woodstock, Saugerties, and Kingston. Explore the nearby Catskill Mountains and indulge in outdoor activities such as hiking, skiing, and fishing.Not only does this home offer a comfortable and convenient lifestyle, but it also comes with low taxes, making it an affordable option for homeowners.Don't miss out on this wonderful opportunity to own a charming ranch-style home in West Hurley, NY. Schedule a viewing today and make this your dream home!

44 Holland Drive, Woodstock
$835,000
3 Beds ⋅ 4 Baths ⋅ 147129 MLS
NO SHOWING TIME. This distinctive custom ranch is characterized by impressive architectural features set amidst expansive park-like surroundings. The thoughtfully designed layout accommodates both formal gatherings around the fireplace and relaxed moments by the saltwater pool, in the screened porch, or on the deck. After outdoor activities, unwind in the infrared dry heat sauna or the master jacuzzi, concluding the day in comfort. Meticulously planned, the home offers a seamless flow from the family room to the kitchen and common areas. The kitchen, renovated in 2008, showcases sleek white cabinets, a pantry, a spacious island, and elegant marble counters. Radiant heat enhances comfort, and a powder room off the kitchen adds convenience.The private wing features two bedrooms and a full bath, while the primary suite features a walk-in closet, private deck access, and an ensuite bath with a soaking jacuzzi. Abundant storage, a laundry chute, and attic storage contribute to practical living. The finished lower level, heated for year-round comfort, includes a sitting room, workroom, garage, half bath, exercise room with an infrared sauna, and a versatile conversation/game area. Recent updates include a new oven, freshly painted living areas, and new wood floors throughout. A custom wall-to-wall bookshelf in the front living room adds character. The residence is complemented by a state-of-the-art water filtration system installed in 2023. Nestled in landscaped grounds, the property offers easy access to various amenities, making it an ideal base for Hudson Valley living.--

33 Maurizi Lane, Woodstock
$2,850,000
3 Beds ⋅ 3 Baths ⋅ 145645 MLS
Ideally situated on a quiet, picturesque dead-end country road in Woodstock, Purdy Hollow is a modern yet quintessential farmhouse on over 41 acres. A flowing brook traverses the sprawling property, with a pool, crystal-clear pond, and an impressive 5000 sf barn completing this pastoral compound.The 3,800 sf main house has been designed as a peaceful rural residence, with idyllic countryside views from every window, cozy, intimate spaces and bright, light-filled rooms perfect for entertaining.The heartbeat of the home's ground floor is an enormous gourmet kitchen, with top-quality appliances and cabinets, that opens to a dining room and a living room with a wood burning fireplace overlooking the pond, the running stream, and scenic woods in the distance. The light-filled lounge leads to a vaulted ceiling veranda, seamlessly blending in with a newly appointed outdoor kitchen and the heated saltwater pool. On the same level, at one end, is an expansive but cozy family room, and on the other end is a library with another wood-burning stone fireplace. Upstairs is more intimate with two lovely bedrooms and a sweeping primary suite with large windows and a generous sized walk-in closet. A fourth room is ideal as a nursery, office, or guest bedroom.The property is evenly split by Purdy Hollow Road, a quiet walking road with almost no traffic, with forever protected views in all directions. The massive, recently restored barn across the street is ready for horses with water and electricity and could also easily be converted into an expansive art studio. There are three fenced paddocks plus plenty of land beyond filled with trails for hiking, spotting wildlife and foraging for mushrooms.Most modern conveniences like air conditioning, backup generator, remote control thermostat, alarm system, and water filtration systems have already been installed, in addition to solar panels that make the house net zero for electric use.The home comes completely turnkey with thoughtfully curated new furniture and soft furnishings.Purdy Hollow is just a few minutes from the center of Woodstock village, less than 15 minutes to downtown Kingston, and under two hours from New York City. With the Thorn Reserve just a few steps away, there are also countless nature preserves for outdoor activities a short drive away, including the Ashokan Reservoir, Indian Head, Overlook, Kaaterskill, and Bluestone Wild Forest.

90 Purdy Hollow Road, Woodstock
$4,200,000
4 Beds ⋅ 6 Baths ⋅ 145194 MLS
Zen Luxury off of one of Woodstock's most desirable roads- sitting on 19.4 acres of land with jaw dropping views of Mount Guardian, this impeccably designed new contemporary residence is sure to impress the most discerning buyer. Take in the natural beauty of your surroundings from the property's very own hiking trails and serene 50 foot blue stone walled salt water pool with elegant patio. The residence is a true work of art, reflecting the majesty of the land. As you enter through the custom oak pivot front door, you are welcomed by a floor to ceiling picture window, with a view of a sourced boulder from the property, bringing drama of the outdoors inside. Through the kitchen complete with top of the line appliances and additional butlers pantry, into the great room replete with oak ceilings, the warmth and energy of space is vast with high ceilings and massive windows offering an abundance of natural light. French doors open to bluestone patios and pathways. Another set of doors lead to a bluestone screen porch, all of which share extraordinary views. Turning left at the entry leads through one of two sets of Italian doors down a barrel ceiling hall artfully lit. The residence includes two guest bedrooms with en suite baths, a primary suite of your dreams, a large quiet den/Au Pair suite with separate entrance and private bathroom, and a guest cottage with full bath and additional outside shower next to the pool. Zen is the only way to describe the feeling of calm and peace in the space of the primary suite with the marble bath, complete with large soaking tub shower room and incredible views. As you walk through this new build, you will be amazed by the impeccable craftsmanship and detail. A welcoming work of art, ready to be called home.

30 Angus Lane, Woodstock
$635,000
3 Beds ⋅ 2 Baths ⋅ 144967 MLS
Sometimes you can buy love! Welcome to Abbey Road. 5.6 acres of pristine private property nestled high in the sky (1.8K ft elevation) directly across from Tobias Mountain. Enjoy all upstate NY has to offer and legendary hiking trails. The house is just a stone's throw away from quaint towns like Mount Tremper, Woodstock, Catskill, and Phoenicia. Located a quick 2 hours from NYC, it's an easy weekend getaway.

446 Abbey Road, Woodstock
$935,000
3 Beds ⋅ 2 Baths ⋅ 143913 MLS
Welcome to 22 Nordic Drive, a fantastic, 2-story Colonial situated on a private road in Woodstock! Featuring 3 bedrooms, 2 bathrooms and 6.39 acres of land, this secluded hideaway is the perfect escape from the hustle and bustle of city life while still having access to all of the amenities and culture Woodstock has to offer! Set far back from the road, this house brings seclusion to a new level, it is nearly impossible for anyone to build in your sight line. The eastern exposure brings amazing sunrises to the property every morning while the northern exposure gives you a fantastic, seasonal view of Overlook Mountain. Upon entering the house from the bluestone walkway to the front porch, you are greeted with a great room with fireplace and an open kitchen. The home features beautiful hardwood floors throughout. The living room has a propane powered fireplace with vaulted ceilings and skylights and opens into the kitchen. The kitchen features marble countertops and stainless steel appliances, perfect for any chef! It also has access to the back bluestone patio. Surrounded in windows and bathed in natural light, the dining room has a great view of the property and, seasonally, of Overlook Mountain. The family room is a great place to relax at the end of the day with access to the back and side patios. Past the kitchen is a private hall with 2 guest bedrooms and a full bathroom. The laundry closet is also down this hallway. Continuing upstairs is the entire primary suite featuring a large bedroom with ample closet space, a full, ensuite bathroom with separate tub and shower and a large balcony with views over the backyard. All of the mechanicals have been well-maintained and many have been upgraded and/or replaced. The crawl space has also been entirely sealed with water and pest proofing. There is also extensive water filtration including a U/V filter,dealkalizer, 20 micron filter and chlorinator. There is also a reverse osmosis system at the kitchen sink. The 6.39 acre property features a beautiful, flat yard with fire pit, gazebo and two sheds (one recently used as a home gym). The large bluestone patio off the back of the house also makes a great space for your outdoor furniture. The well-maintained, mature landscaping only adds to the privacy while the front set back from the street allows for a large circular driveway with ample parking. And with Snake Rocks Preserve at the top of the road you'll always have walking trails! Perfection!

22 Nordic Drive, Woodstock
$3,000,000
4 Beds ⋅ 6 Baths ⋅ 143043 MLS
Once in a lifetime opportunity to own a three residence compound in one of the upstate region's most coveted locations. Cooper Lake Road is just moments to the historic hamlet of Bearsville with its wonderful theater, markets, and restaurants. Just a minute further along the road is bustling Woodstock, NY, one of the most vibrant villages in all of New York. The main house is a rare 1963 mid-century modern home with internationalist sensibilities, open floor plan, and two exquisite private bedroom suites. Indoor-outdoor flow is available from nearly every room, and the natural stone patios create expansive outdoor entertaining opportunities. Nearby, a series of Japanese style ponds create an enchanting secret garden shaded by mature trees and plantings encouraged over decades. The nearby guesthouse is inspired by an Adirondack style cabin and allows for guests to stay just steps away. The expansive studio is a multi-functional space that serves as pool house, additional guesthouse, and artist studio with vaulted ceilings soaring over twenty five feet high. The open upper level is sun-drenched, with lower level guest apartment that flows nicely out to the mature gardens and luxury pool with pergola and generous stone patio. The three buildings are perfectly sited in the park like setting with towering mature trees, orchard, stone walls, and views of the surrounding Catskill Mountains.

201 Cooper Lake, Woodstock
$325,000
2 Beds ⋅ 2 Baths ⋅ 141835 MLS
Do you believe in reincarnation? This light-flooded, 2-BR, 2-BA, bungalow-style home was born ca. 1860, & it's awaiting its re-birth. Helping to get things started, in the LR there's a WB, cast-iron stove that practically heats the whole house & rough-hewn barnwood paneling, wide-plank pinewood flooring to swoon over, double-hung Pella windows & generous closet space throughout, a southern exposure, & a kitchen nook that could easily overwhelm with its cozy allure. Happily, there are also 2 full baths, one on each floor. The nearly 1.5 acre-lot offers both a generously-sized yard, as well as plenty of peripheral woods, & seasonal views of the Catskill mountains will delight. Kingston, Woodstock, & Saugerties Village, where fine dining, shopping, services, & entertainment abound, are all within a 15-min. drive. And, the whole shebang is located under 2 hours from mid-town Manhattan. Spark your own joy, & make this antique slice of charm your weekend or FT respite from the daily grind.

1615 Glasco Turnpike, Woodstock
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