Woodstock, NY Homes for Sale

• 

  

  

  /62

  $799,000

  • 2 Beds
  • 1 Bath
  • 1,256 Sq Ft

  90 Aarons Way, Mount Tremper, NY 12457

  Tucked away at the end of a quiet private road near the top of Roundtop Mountain, this 2-bedroom, 1-bath home offers serene seclusion surrounded by protected DEP land and a private forest preserve. A true nature lover's paradise, the property is alive with wildlife and boasts beautifully landscaped grounds, seasonal mountain views, and the potential for year-round vistas with the clearing of

  Darlene Griffin Halter Associates Realty

  90 Aarons Way, Mount Tremper, NY 12457
• 

  

  

  /28

  $815,000

  • 2 Beds
  • 2 Baths
  • 1,416 Sq Ft

  2318 Glasco Turnpike, Woodstock, NY 12498

  This classic 1890s farmhouse marries period charm with high-end modern amenities in a natural setting. Bordered by quiet woodlands, meadows and a bluestone wall, the house stands out as a gem. A spacious living room, flooded with natural light, flows seamlessly into a large separate dining room featuring window benches looking onto an ample side deck-perfect for morning coffee bathed in sunrise.

  Jeannine Simmons Corcoran Country Living

  2318 Glasco Turnpike, Woodstock, NY 12498
• 

  

  

  /41

  $729,000

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft

  18 Country Club Ln, Woodstock, NY 12498

  Stunning reimagined Ranch, just 1/2 Mile from the Center of Woodstock, 2/10 of a Mile to the NYC Bus Route,yet providing an excellent sense of privacy, and a perfect rural setting.Beautifully, and thoughtfully updated baths and kitchen, embracing the best of Modern Design principals and practicality.The perfect country escape, yet within easy access to restaurants, shopping and

  Margo Obourn Win Morrison Realty - W

  18 Country Club Ln, Woodstock, NY 12498
• 

  

  

  /8

  $289,000

  • Land
  • 10 Acres
  • $28,900 per Acre

  4912 New York 212, Willow, NY 12495

  Discover the opportunity to create your dream escape on this serene 10-acre parcel nestled in the quiet hamlet of Willow, NY. Tucked away in nature yet just a short drive from the vibrant village of Woodstock, this expansive property offers the perfect blend of privacy and proximity. Towering trees, dappled sunlight, and the calming sounds of nature create a peaceful setting for your future home,

  Richard Vizzini Corcoran Country Living

  4912 New York 212, Willow, NY 12495
• 

  

  

  /25

  $479,500

  • 3 Beds
  • 1 Bath
  • 1,164 Sq Ft

  44 Overlook Dr, Woodstock, NY 12498

  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

  44 Overlook Dr, Woodstock, NY 12498
• 

  

  /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
• 

  

  /56

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 2,377 Sq Ft

  35 Abbey Rd, Mount Tremper, NY 12457

  35 Abbey Road — A Mid-Century Sanctuary minutes from Woodstock TownTucked away off of Abbey Rd and just a short pass over a charming stream you'll arrive at this pristine, authentic mid-century retreat, nestled in the heart of Woodstock's beloved Abbey Road. Set on 5.4 magical acres, this serene property captures the essence of Catskills living- graceful, grounded, and surrounded by

  Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

  35 Abbey Rd, Mount Tremper, NY 12457
• 

  

  /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
• 

  

  /49

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 1,864 Sq Ft

  12 Library Ln, Woodstock, NY 12498

  Tucked along tranquil Library Lane, this classic red cottage offers a rare blend of in-town convenience and private, garden-like seclusion. PLUS, there is a legal Woodstock STR permit! Behind the home, a fully fenced backyard - shaded by mature trees and thoughtfully landscaped - frames both the primary residence and detached guest studio with its legal short-term rental permit. This is a true

  Eric Amaral Coldwell Banker Village Green

  12 Library Ln, Woodstock, NY 12498
• 

  

  /10

  $158,000

  • Land
  • 2.10 Acres
  • $75,238 per Acre

  00 Whites Ln, Woodstock, NY 12498

  PRICE REDUCEDPrime 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.

  Daniel Hauspurg Potter Realty

  00 Whites Ln, 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

  $1,295,000

  • 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 Compass Greater NY, LLC

  540 Mount Tobias Rd, Mount Tremper, NY 12457
• 

  

  /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
• 

  

  /28

  $575,000

  • 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

  • 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

  $1,375,000

  • 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
• 

  

  /44

  $1,395,000

  • 4 Beds
  • 4 Baths
  • 3,172 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, tons of sunlight and bespoke stainglass throughout. The layout is wideopen to your own creativity and all the possibilities you can conjure up. Permitted as asuccessful year 'round Airbnb andcurrently configured with

  Carol Graham Corcoran Country Living

  5 Downer Ln, Woodstock, NY 12498
• 

  

  /35

  $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 introduced thoughtful upgrades throughout, including a brand-new septic system, kitchen and baths, heating system, flooring, and enhanced insulation. Original stained glass windows remain as artistic focal points, honoring the home's

  Sally Sprogis Four Seasons Sotheby's Int'l R

  40 Lower Byrdcliffe Rd, Woodstock, NY 12498
• 

  

  /26

  $699,000

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

  1521 Glasco Turnpike, Woodstock, NY 12498

  WELL PRICED FOR A TIMELY SALE-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

  Kathryn Johnson William Pitt Sothebys Int Rlty

  1521 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /33

  $579,000

  • 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

  $450,000

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

  58 Baker Rd, Bearsville, NY 12409

  MOTIVATED SELLER! 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

  Heather Martin United RE Hudson Valley Edge

  58 Baker Rd, Bearsville, NY 12409
• 

  

  /51

  $759,000

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft

  97 John Joy Rd, Woodstock, NY 12498

  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

  Benjamin Armento Coldwell Banker Village Green

  97 John Joy Rd, Woodstock, NY 12498
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /25

  $226,100

  • 3 Beds
  • 2 Baths
  • 944 Sq Ft

  11 Fel Qui Rd, Woodstock, NY 12498

  Tucked away for the ultimate in privacy. This totally affordable cute ranch needs only a little of your attention before moving right in. Lots of land for your peace and quiet as a weekend get away or your primary residence. There are three bedroom and two full bathrooms with an open concept kitchen and living room. If you love being surrounded by nature, being near mountains for skiing and a

  Melissa Terman River Realty Services, Inc.

  11 Fel Qui Rd, Woodstock, NY 12498
• 

  

  /37

  $824,000

  • 4 Beds
  • 3 Baths
  • 1,456 Sq Ft

  40 Maxs Place, Kingston, NY 12401

  Tucked away on a quiet private road, this exceptional property offers a rare blend of privacy, style, and resort-like amenities—all just minutes from Woodstock and the best of the Catskills. At the heart of this beautifully updated home is a truly remarkable feature: a 40x60 indoor pool and sauna, creating an all-season sanctuary that's as perfect for quiet morning swims as it is for

  Leigh Wagner-Quintana Keller Williams Realty HV Nort

  40 Maxs Place, Kingston, NY 12401
• 

  

  /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 - 73, Page 2 of 2