Woodstock, NY Houses for Sale

Welcome to Juniper Woods. Nestled on four serene acres just minutes from the center of Woodstock, Juniper Woods is a custom-designed, exquisitely renovated residence offering the perfect balance of sophistication, tranquility, and convenience. With over 3,000 square feet of thoughtfully curated living space, this three-bedroom, three-bathroom home is rare, architecturally striking, and deeply

Victoria Stent Coldwell Banker Village Green

Nestled in the heart of Woodstock, this extraordinary 70+ acre estate is a rare offering of artistic heritage, architectural beauty, and serene natural surroundings. Known as The Stone House on Striebel Road, this iconic bluestone compound has stood at the crossroads of music, literature, and counterculture for over a century.Built in 1914 as a country retreat, the main Stone House

Michelle Bergkamp Corcoran Country Living

The best of both worlds!A boho cottage paradise and a modern ADU (Accessory Dwelling Unit). Peace and tranquility and 3 miles from the center of the most famous small town in the world. Five-star dining and unique shopping opportunities.The property is situated adjacent to the Thorne Preserve - 60 acres boasting the most painted views of Overlook Mountain. The preserve is a sweeping grassland

Benjamin Armento Coldwell Banker Village Green

Discover the epitome of modern luxury in this brand new build, with a sleek aesthetic that seamlessly blends style and comfort. Using ecological and state of the art building practices highlighted by exceptional craftsmanship and distinctive design. Ascend an impressive switchback floating staircase to a stunning wall of windows that flood the open concept, living, kitchen, and dining area

Richard Vizzini Corcoran Country Living

Historic Byrdcliffe Estate on One of Woodstock's Most Beloved Roads. Step into a piece of Woodstock's storied past with this enchanting 1910 Arts & Crafts masterpiece, gracefully situated on nearly six bucolic acres along one of the town's most picturesque and sought-after roads. Originally owned by Jane BYRD Whitehead and Ralph RadCLIFFE Whitehead, two of the visionary founders of the Byrdcliffe

John Kralik Compass Greater NY, LLC

Tucked away on 7.26 acres of lush, storybook landscape with a stream-fed pond, this quintessential Woodstock home is more than a residence—it’s an experience. As you approach via a winding driveway that crosses a babbling stream and year-round waterfalls, the magic begins. You can hear the cascading water from the house itself, setting the tone for the serenity that follows. The main home offers

Lisa Halter Halter Associates Realty Inc

Nestled atop Mid Mountain, just five minutes from the heart of Woodstock, this enchanting eight-acre property welcomes you via a long and winding drive that sets the tone for what awaits: a hidden retreat that feels worlds away. Originally the home of an early Woodstock creative, the residence radiates a timeless charm—private, whimsical, and steeped in inspiration. Set amid lush trees and backed

Laurie Ylvisaker Coldwell Banker Village Green

Tucked away in the pristine Ohayo Mountain forest and less than a mile from the heart of Woodstock, Cannon House offers the rare combination of seclusion, comfort, and modern design. Set on 1.65 acres, this contemporary retreat, built in 2020, is thoughtfully designed to immerse you in the natural surroundings while providing every modern convenience. With three bedrooms and two and a half baths,

Laurie Ylvisaker Coldwell Banker Village Green

OPEN HOUSE! 7/5/2025 from 11:00 AM to 2:00 PM. Come check out the amazing views!Perfectly positioned in the sought-after community of Grog Kill, this mountain retreat, midway between Woodstock and Phoenicia, offers complete privacy and sweeping Catskill Mountain views. Set on 9.5 acres, the home features 33 thoughtfully placed windows and doors that bathe the interior in natural light and

Amy Lonas Coldwell Banker Village Green

A spectacular view of Bass Meadow and mountains is just one of the highpoints of this beautiful Cape Cod home on 6.1 acres located a few miles from Woodstock Village. From the home's wraparound stone patio and large windows, imagine looking out at a serene 70-acre vista of meadow and woods that is protected from development. This lovely, turnkey 2209-square-foot home features an open-plan living

Gary Heckelman Halter Associates Realty Inc

Blending classic country charm with modern sophistication, this newly built modern farmhouse offers over 3,000 square feet of beautifully finished living space. Designed with clean lines, a neutral palette, and layered textures, it delivers a timeless aesthetic full of warmth and character. The home features four spacious bedrooms, three and a half baths, a fully finished lower level, and

Richard Vizzini Corcoran Country Living

Welcome to the Woodstock Retreat House.This exceptional multi-residential compound has been thoughtfully renovated to the highest standards and is fully furnished with a curated mix of vintage and contemporary pieces. A proven high-volume income producer, the property offers flexibility as a primary residence, part-time escape, or short-term rental investment.Set on 1.5 lush,

Leslie Foti Coldwell Banker Village Green

Set in the quiet surroundings of Woodstock, this thoughtfully renovated ranch-style home offers over 2,000 square feet of comfortable living space. With three bedrooms and hardwood floors throughout the main level, the layout is open and welcoming.At the center of the home is a bright, spacious living room with a brick fireplace—ideal for relaxing evenings. It flows into a dining area and

Mario Geissler Four Seasons Sotheby's Int'l R

Edible Acres! with Mountain Views, Stream, and Unexpected CharmThis timeless 3-bedroom, 1.5-bath home offers 2,300 +/- sq. feet of inviting, light-filled space. Set on 1.73 acres with surprises at every turn - a forested path, rock outcroppings, the Tynekill stream boarders on side, a lush rolling lawn, multiple gardens. The back yard is bursting with flowers, a woodland path leads to a

Melissa Mayes Serhant LLC

Nestled on 10.6 private acres at the end of a quiet cul-de-sac, this custom-built contemporary home offers a rare blend of privacy, space, and modern comfort, highlighted by charming Arts & Crafts details. This spacious 4-bedroom, 2.5-bath home features stunning handcrafted cherry woodwork in the kitchen and stairway, beautifully complemented by gorgeous hardwood floors throughout. A skylit foyer

Megan Rios Berardi Realty

Three bedroom, one bath, 1124 ft.2 in Woodstock. Walking distance to the Bearsville theater formally owned by Bob Dylan's manager, Albert Grossman with music and restaurants. New refrigerator, new dishwasher, stove like new ( three years old). Hot water tank(3 years old) microwave, new carpet, professionally painted inside and out, living room and large multi use room (could be 4th bedroom) not

Qizhan Yao Realmart Realty, LLC

Welcome to Happy Brooks , The much-loved compound for many years of Woodstock Festival co-founder and legendary music industry icon Michael Lang, this mythic Mt. Tremper property boasts true style, along with a creative pedigree that dates back to the 1920s. Originally built for the artist G. Adolph Anderson, the 17 acre estate features three architecturally significant & historic structures

Nancy Felcetto Brown Harris Stevens Hudson

Tucked back on a six acre lot just minutes to the town of Woodstock sits this fairytale two bedroom cottage. The woodland view is yours to explore, the deep forest of evergreens, ferns and moss. Inside, you're tucked into charming spaces or enjoying the expansive Great Room, with a stone fireplace at the center and vaulted ceilings with beautiful exposed beams. A wall of windows frames the view.

Annabel Taylor Four Seasons Sotheby's Int.

Welcome to Happy Brooks , The much-loved compound for many years of Woodstock Festival co-founder and legendary music industry icon Michael Lang, this mythic Mt. Tremper property boasts true style, along with a creative pedigree that dates back to the 1920s. Originally built for the artist G. Adolph Anderson, the 17 acre estate features three architecturally significant & historic structures

Nancy Felcetto Brown Harris Stevens HV LLC

Tucked along tranquil Library Lane, this classic red cottage offers a rare blend of in-town convenience and private, garden-like seclusion. Behind the home, a fully fenced backyard - shaded by mature trees and thoughtfully landscaped - frames both the primary residence and a detached guest studio with a legal short-term rental permit, creating a true village retreat that feels peaceful and tucked

Laurie Ylvisaker Coldwell Banker Village Green

Just a short walk from the vibrant village of Woodstock, this exceptional modern contemporary home is truly one-of-a-kind. Designed by a renowned Park Avenue architect, this residence perfectly blends modern design and comfortable living, with no detail overlooked. As you enter through the foyer, you're immediately struck by the abundance of natural light streaming through the wall-to-wall

Megan Rios Berardi Realty

Turn key Opportunity - whether you are looking for a full time residence or second home. Often referred to as Zena Cottage by Airbnb guests, this charming home is 3 minutes to the Village of Woodstock, and a short drive to hip uptown Kingston, Rhinebeck and the NYS Thruway. 2 hrs from NYC.Set against a private wooded backdrop, this 1957 home on 1/3 of an acre has a lush lawn, spectacular

Benjamin Armento Coldwell Banker Village Green

Country charm -- less than a mile from the Woodstock Village Green! A stream meanders by the massive screened porch and deck. There are also views of your own pond while you enjoy dining al fresco just outside the sliding glass kitchen door. This house transports you to a light, airy, simpler lifestyle. The kitchen opens to a gracious dining room (with a breakfast bar and additional kitchen

Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

Nestled along one of the most enchanting, winding roads in Woodstock, this stunning contemporary ranch offers the perfect blend of modern convenience and serene country living with the addition of a lot of extra space in the form of a lower-level accessory dwelling unit with a separate entrance; it adds two bedrooms and provides an ideal space for guests. Alternatively, it might be used as a

Ellen Osgood Coldwell Banker Village Green

Once-in-a-Generation Opportunity: Private Estate in the Heart of Woodstock VillageTucked away in the very center of Woodstock, this rare private estate offers an extraordinary combination of space, seclusion, and potential. Lovingly held by the same family for over 40 years, the property spans nearly 8 acres, with a vast open meadow—larger than a football field—offering unmatched privacy

Nan Potter Potter Realty

Bright, Spacious, Ranch Just Minutes from Woodstock. Welcome to this beautifully updated 3-bedroom, 2-bath ranch at the end of a quiet cul-de-sac in a, friendly, established neighborhood between Woodstock and Bearsville. Step inside and feel instantly at home. Natural light pours through the windows, highlighting warm hardwood floors and a bright open layout, with skylights above adding

Brenda Graf Corcoran Country Living

Buckle up! 5 Downer Lane may be themost interesting property you see allyear! This 19th century hand-hewnbarn-to-house conversion has 35 footceilings, sunlight and bespoke stainglass throughout. The layout is wideopen to your own creativity and all the possibilities youcan conjure up. Permitted as asuccessful year ‘round Airbnb andcurrently configured with threebedrooms (two in the turret!) and

Casey Kearns Corcoran Country Living

Nestled in Woodstock's storied Byrdcliffe district, this charming 1920's home balances original character with modern comforts. A comprehensive renovation has brought thoughtful updates throughout, including a brand-new kitchen and baths, upgraded flooring, enhanced insulation, a new roof and a new heating system. Original stained glass windows serve as artistic focal points, honoring the home's

Sally Sprogis Four Seasons Sothebys Intl

Tucked away on 2.2 acres of peaceful, park-like grounds, this inviting home offers the perfect blend of privacy, beauty and convenience. A long gravel driveway winds past tall trees and green space, opening to your own hidden haven—set well back from the road, yet just minutes to Woodstock and Saugerties, with their vibrant shops, restaurants, and culture.The approach is unforgettable: a wide

Kathryn Johnson William Pitt Sothebys Int Rlty

Nearly Six Lush, Scenic And Private Acres Located Eight Minutes From The Heart Of Woodstock! This Home Features Two / Possibly Three Bedrooms And Two Full Baths. Meticulously Maintained! Enjoy Sunrises Or Sunsets From The Wrap Around Deck. Relax And Take In All Of The Tranquility While Sitting Stream Side Or Enjoy The Changing Of The Leaves During The Beautiful Fall Season While Sipping Hot

Michael Alpert Daniel Gale Sothebys Intl Rlty

Live above the clouds in a Woodstock contemporary just a few minutes from the bustling center of the village! The views are amazing and expansive, and from almost every room. The Ashokan Reservoir, the entire Shawangunk ridge from Mohonk to Sam's Point, Ohayo Mountain and even a bird's eye view of the buildings in the center of town anchored by the old Dutch Church steeple. But this three level

Daniel Winn Halter Associates Realty

Nestled in the heart of Woodstock, this beautifully remodeled 4-bedroom, 2.5- bathroom home seamlessly blends modern comfort with timeless charms. With an open-concept layout and soaring vaulted ceilings, the home feels both spacious and inviting. Original hardwood floors run throughout, adding warmth and character. The custom-designed kitchen is a chef's dream, featuring brand new cabinetry,

Eliana Amodio Amodio Real Estate & Prop

OPEN HOUSE! 7/5/2025 from 11:00 AM- 1:00 PM! Come check out this amazing property! The perfect Upstate compound. Located in one of the most beautiful locations in Woodstock, this 3 bedroom 2 bath home includes a new 550 square ft guest house for a total of 1973 square feet, an in-ground pool and many recent upgrades and improvements. Just across the way from the Thorne Preserve with its

Amy Lonas Coldwell Banker Village Green

WOODSTOCK-Rustic ranch in a convenient location, is available immediately! Open living area has cathedral ceilings, a wall of windows and a nice dining area leading to the deck. There are two nice size bedrooms, one being en-suite, both with walk-in closets. A second full bath is down the hall. The kitchen has an entrance from the dining area or hallway, with plenty of cabinets, including a

Dana Goldberg Houlihan Lawrence-R

Discover modern living at its finest with this newly built contemporary home, perfectly nestled on 2 private acres along the enchanting Sawkill Creek in Woodstock. Designed with both style and practicality in mind, this property seamlessly blends sleek modern amenities with the natural beauty of its surroundings.Built above the floodplain in accordance with FEMA standards, the home offers

Jeanne Boice Howard Hanna Rand Realty

WOODSTOCK ARTS AND CRAFTS CLASSIC - Circa 1905 vintage details of this 3 bedroom, 2 bath home include wide plank floor boards, tin ceiling, custom built-in's and rocking chair front porch. Many recent improvements—roof, heating system, drainage system—bring the home's function into the 21st Century. Every room (except the kitchen) on all 3 levels has been fully renovated to a high standard,

Peter Cantine Halter Associates Realty

Enchanting Woodstock Compound with Craftsman Home, Historic Barn & Cottage. Welcome to a truly rare offering in the heart of the Catskills—just minutes from the center of Woodstock, yet tucked away in a storybook setting of trees, meadows, and the soothing sounds of the Sawkill stream. This private 1.85-acre homestead compound blends rustic charm with modern versatility, featuring three distinct

Michelle Bergkamp Corcoran Country Living

Discover the perfect blend of comfort and opportunity in this charming duplex situated near the heart of Woodstock. This legal two-family home, each unit approximately 900 square feet, offers a unique chance to live in one side while renting out the other, making it an ideal investment property or a cozy haven for extended families.As you approach the property, a separate driveway for

Pieta Williams Halter Associates Realty