Woodstock, NY Homes for Sale

• 

  

  

  /53

  $1,695,000

  • 3 Beds
  • 3.5 Baths
  • 3,072 Sq Ft

  253 Upper Byrdcliffe Rd, Woodstock, NY 12498

  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

  John Kralik Compass Greater New York, LLC

  253 Upper Byrdcliffe Rd, Woodstock, NY 12498
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Get a Boost
• 

  

  

  /30

  $2,100,000

  • 9 Beds
  • 10 Baths
  • 8,452 Sq Ft

  0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498

  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

  0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498
• 

  

  

  /38

  $795,000

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft

  276 Chestnut Hill Rd, Woodstock, NY 12498

  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.

  276 Chestnut Hill Rd, Woodstock, NY 12498
• 

  

  

  /33

  $2,100,000

  • 9 Beds
  • 10 Baths
  • 8,452 Sq Ft

  Unlisted Address

  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

  Unlisted Address
• 

  

  

  /10

  $168,000

  • Land
  • 2.10 Acres
  • $80,000 per Acre

  00 Whites Ln, Woodstock, NY 12498

  Prime location offering both privacy and proximity to the heart of Woodstock Village. Although the parcel's address is Whites Lane it is a fully wooded lot fronting Playhouse Lane Extension, a private and secluded road starting at the junction of Whites Lane and Playhouse. This setting is ideal for building your dream home while enjoying the convenience of walking to the Village. This parcel is

  Daniel Hauspurg Potter Realty

  00 Whites Ln, Woodstock, NY 12498
• 

  

  /28

  $1,225,000

  • 3 Beds
  • 2 Baths
  • 1,948 Sq Ft

  99 Cannon Cir, Woodstock, NY 12498

  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

  99 Cannon Cir, Woodstock, NY 12498
• 

  

  /33

  $2,175,000

  • 3 Beds
  • 2 Baths
  • 3,100 Sq Ft

  44 Old Wagon Rd, Wood Stock, NY 12498

  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

  44 Old Wagon Rd, Wood Stock, NY 12498
• 

  

  /36

  $1,400,000 Open Sun 1:30PM - 2:30PM

  • 3 Beds
  • 4 Baths
  • 3,120 Sq Ft

  540 Mount Tobias Rd, Mount Tremper, NY 12457

  Step into the pages of Dwell magazine and immerse yourself in this architect-designed gem offering a harmonious blend of modern design and natural beauty. Feel a wave of calm wash over you, greeted by resplendent views, clean lines, and a wall of windows overlooking majestic mountain vistas. Modernists rejoice. Design aficionados delight. And nature enthusiasts revel. A minimalist aesthetic

  Alexander James Fresh Air Realty

  540 Mount Tobias Rd, Mount Tremper, NY 12457
• 

  

  /38

  $1,200,000

  • 3 Beds
  • 3.5 Baths
  • 2,337 Sq Ft

  94 the Middle Way, Mount Tremper, NY 12457

  Privately sited on a quiet back road in the Catskills, Noorden House is a modern retreat offering both seclusion and convenience—just 20 minutes to Woodstock, 15 to Phoenicia, and 30 to two ski mountains. Elevated on over 5 acres, the home enjoys distant mountain views, beautifully landscaped grounds, and serene natural features including a heated freeform pool, a small pond, and a picturesque

  Jennifer Grimes Country House Realty Inc

  94 the Middle Way, Mount Tremper, NY 12457
• 

  

  /39

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 2,209 Sq Ft

  11 Louie Way, Woodstock, NY 12498

  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

  11 Louie Way, Woodstock, NY 12498
• 

  

  /32

  $1,749,900

  • 3 Beds
  • 2.5 Baths
  • 3,076 Sq Ft

  16 Juniper Ln, Woodstock, NY 12498

  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

  16 Juniper Ln, Woodstock, NY 12498
• 

  

  /44

  $1,299,000

  • 5 Beds
  • 3 Baths
  • 3,696 Sq Ft

  3207-3209 New York 212, Bearsville, NY 12409

  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

  3207-3209 New York 212, Bearsville, NY 12409
• 

  

  /56

  $549,000

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  680 Zena Rd, Woodstock, NY 12498

  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

  680 Zena Rd, Woodstock, NY 12498
• 

  

  /28

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft

  196 Tinker St, Woodstock, NY 12498

  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

  196 Tinker St, Woodstock, NY 12498
• 

  

  /34

  $1,495,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,496 Sq Ft

  8 Tannery Brook Rd, Woodstock, NY 12498

  Positioned just moments from the vibrant energy of Tinker Street and the heart of Woodstock, this 2,496 sqft mixed-use property offers an exceptional opportunity to live, work, and invest in one of the Hudson Valley’s most iconic artistic communities. The first floor is owner-occupied, the upstairs serves as a well-established Airbnb, while the street-level commercial space is separately rented,

  STEVEN WROBEL JR. Serhant LLC

  8 Tannery Brook Rd, Woodstock, NY 12498
• 

  

  /50

  $1,450,000

  • 4 Beds
  • 4 Baths
  • 3,193 Sq Ft

  279 Cooper Lake Rd, Bearsville, NY 12409

  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 bonus 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

  279 Cooper Lake Rd, Bearsville, NY 12409
• 

  

  /66

  $1,450,000

  • 4 Beds
  • 4 Baths
  • 1,867 Sq Ft

  279 Cooper Lake Rd, Woodstock, NY 12498

  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

  279 Cooper Lake Rd, Woodstock, NY 12498
• 

  

  /40

  $1,395,000

  • 4 Beds
  • 5 Baths
  • 3,100 Sq Ft

  5 Downer Ln, Woodstock, NY 12498

  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

  Jason Karadus Corcoran Country Living

  5 Downer Ln, Woodstock, NY 12498
• 

  

  /38

  $1,182,750

  • 3 Beds
  • 2.5 Baths
  • 2,644 Sq Ft

  241 Silver Hollow Rd, Willow, NY 12495

  A whimsical compound just minutes to the village of Woodstock. On the two acre property you'll find a rushing stream and scenic pond, a three bedroom house, a cabin and a beautiful, modern barn that the current owners use for gatherings, yoga & music. The barn has been entirely rebuilt from the ground up so you'll find new electrical, a new heating & cooling system, local custom millwork, and

  Annabel Taylor Four Seasons Sothebys Intl

  241 Silver Hollow Rd, Willow, NY 12495
• 

  

  /34

  $599,000

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  40 Lower Byrdcliffe Rd, Woodstock, NY 12498

  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

  40 Lower Byrdcliffe Rd, Woodstock, NY 12498
• 

  

  /24

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 2,077 Sq Ft

  1521 Glasco Turnpike, Woodstock, NY 12498

  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

  1521 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /33

  $599,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  328 John Joy Rd, Woodstock, NY 12498

  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

  328 John Joy Rd, Woodstock, NY 12498
• 

  

  /25

  $595,000

  • 3 Beds
  • 2 Baths
  • 1,376 Sq Ft

  58 Baker Rd, Bearsville, NY 12409

  Discover the perfect blend of comfort, creativity, and seclusion in this charming 3-bedroom, 2-bath home nestled on almost 3 acres of varied landscape—meadows, wooded areas, striking rock outcroppings, and breathtaking mountain views. Whether you’re seeking a full-time residence or a weekend escape, this property offers a unique mix of relaxation and opportunity. Step inside to a warm and

  Heather Martin United RE Hudson Valley Edge

  58 Baker Rd, Bearsville, NY 12409
• 

  

  /79

  $2,500,000

  • 7 Beds
  • 7 Baths
  • 3,960 Sq Ft

  2465 Glasco Turnpike, Woodstock, NY 12498

  Discover a rare opportunity in the heart of Woodstock, NY— with special status, granted by NYS supreme court, which allows rentals of any length, anytime, not subject to any restrictions from the town of Woodstock, or the county. This five-cabin retreat is on over 6 private acres, offering multiple possibilities: a thriving short-term rental, a secluded family/friends compound, or a unique

  Mirav Ozeri The Machree Group, LLC

  2465 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /25

  $500,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  3271 Route 212, Bearsville, NY 12409

  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

  3271 Route 212, Bearsville, NY 12409
• 

  

  /25

  $500,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  3271 Route 212, Bearsville, NY 12409

  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

  3271 Route 212, Bearsville, NY 12409
• 

  

  /33

  $1,888,000

  • Land
  • 61 Acres
  • $30,981 per Acre

  TBD Zena Rd, Woodstock, NY 12498

  An incredible, rare opportunity in Woodstock. It has been very long time since a parcel of this magnitude has available for sale in Woodstock. This contiguous 60-acre property, consisting of two 30-acre lots, features rolling hills, stunning rock outcroppings, mountain views, and diverse mature trees, uniquely offering both beauty and potential. A privately built road, completed by the owners,

  Baris Demirel Serhant LLC

  TBD Zena Rd, Woodstock, NY 12498
• 

  

  /28

  $1,888,000

  • Land
  • 61 Acres
  • $30,981 per Acre

  TBD 60 Acre Zena Rd, Woodstock, NY 12498

  An incredible, rare opportunity in Woodstock.It has been very long time since a parcel of this magnitude has available for sale in Woodstock. This contiguous 60-acre property, consisting of two 30-acre lots, features rolling hills, stunning rock outcroppings, mountain views, and diverse mature trees, uniquely offering both beauty and potential. A privately built road, completed by the

  Baris Demirel Serhant LLC

  TBD 60 Acre Zena Rd, Woodstock, NY 12498
• 

  

  /31

  $219,000

  • Land
  • 3.43 Acres
  • $63,848 per Acre

  2 John Joy Rd, Woodstock, NY 12498

  Embrace the opportunity to build your dream home on this shovel-ready building lot in the idyllic surroundings of Woodstock, New York. Situated amidst incredible trees and enveloped in peace and tranquility, this parcel offers the perfect setting for your Catskill Mountain retreat. With approvals for septic already in place and a potential building site identified, the land has been meticulously

  Eric Amaral Coldwell Banker Village Green

  2 John Joy Rd, Woodstock, NY 12498
• 

  

  /16

  $349,000

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  7 Dixon Ave, Woodstock, NY 12498

  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 Inc.

  7 Dixon Ave, Woodstock, NY 12498
• 

  

  /35

  $1,200,000

  • Land
  • 75 Acres
  • $15,915 per Acre

  626 Wittenberg Rd, Bearsville, NY 12409

  Magnificent 8+ acre meadow across from Cold Brook Road PLUS 66 acres of beautiful rolling property with two streams and magical wet and dry areas in the woods. Possible single Estate property or subdivide into several parcels. Access from Wittenberg Road and views nestled in the Wittenberg Valley just past where the roads to Glenford, Mt. Tremper and Bearsville meet. Property has access on

  Robert Stang LIVEARTHCO CONSULTING LLC

  626 Wittenberg Rd, Bearsville, NY 12409
• 

  

  /13

  $499,000

  • Land
  • 3.00 Acres
  • $166,333 per Acre

  547 Glenford Wittenberg Rd, Bearsville, NY 12409

  This is an 86.2 acre property that is being subdivided into two 3 acre parcels and one 10 acre parcel. The 10 ac parcel will be on the pond and the two 3 acre parcels are across the street from Yankeetown Pond.

  Siobhan Scanlan Win Morrison Realty-K

  547 Glenford Wittenberg Rd, Bearsville, NY 12409
• 

  

  /6

  $184,900

  • Land
  • 2.31 Acres
  • $80,043 per Acre

  100 Zena Rd, Woodstock, NY 12498

  One of the last commercial lots in Woodstock. Zoned neighborhood commercial..excellent drainage. Great location for nursery school, medical or dental clinic, funeral home, or professional office, bank retail mix strip complex. Based on Zoning and bulk requirements site can facilitate approx. 16,000 sq. ft. of building...Soil has excellent drainage for inground septic system. The Town Building

  Michael Bernholz Sr. Hudson Valley Appraisal

  100 Zena Rd, Woodstock, NY 12498
• 

  

  /31

  $1,099,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,252 Sq Ft

  32 Maurizi Ln, Woodstock, NY 12498

  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

  32 Maurizi Ln, Woodstock, NY 12498
• 

  

  /56

  $1,790,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,052 Sq Ft

  2565 Route 212, Woodstock, NY 12498

  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

  2565 Route 212, Woodstock, NY 12498
• 

  

  /59

  $769,000

  • 4 Beds
  • 3 Baths
  • 1,804 Sq Ft

  26 Cowboy Trail, Saugerties, NY 12477

  Expansive Cape Cod Retreat in Saugerties - Style, Space & Versatility on 3.6 Private AcresWelcome to your dream home in the heart of Saugerties! This 4000+ sq ft home perfectly blends design with everyday comfort, all set on 3.6 peaceful and private acres in the beautiful Hudson Valley.Inside, you'll find 3 spacious bedrooms and 3 full bathrooms on the main level, along with a

  Ron Knowles Century 21 Alliance-NP

  26 Cowboy Trail, Saugerties, NY 12477

Showing Results 41 - 76, Page 2 of 2