Woodstock, NY Homes for Sale

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  /17

  $1,995,000

  • 8 Beds
  • 10 Baths
  • 12,393 Sq Ft

  20 Country Club Ln, Wood Stock, NY 12498

  Experience the legacy of Woodstock through this extraordinary historic offering. Once home to the iconic Woodstock Lodge and The Pinecrest, this storied 6.5-acre property offers a unique opportunity to reimagine a legacy estate in one of the Hudson Valley's most sought-after destinations.Set on scenic, gently rolling land with a blend of open clearings, wooded trails, and a seasonal

  Kathryn Johnson William Pitt Sothebys Int Rlty

  20 Country Club Ln, Wood Stock, NY 12498
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  /42

  $749,000

  • 3 Beds
  • 2 Baths
  • 1,553 Sq Ft

  145 Tinker St, Woodstock, NY 12498

  In the heart of Woodstock Village, this beautifully reimagined Colonial offers the rare combination of historic character, modern comfort, and true **walk anywhere convenience**. Set beside Tannery Brook, the home is designed to make the most of its stream side setting, with light-filled interiors, an open-concept layout, and two sets of French doors that create an effortless connection to the

  James Billingsley Halter Associates Realty Inc

  145 Tinker St, Woodstock, NY 12498
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  /24

  $600,000

  • Land
  • 28.17 Acres
  • $21,299 per Acre

  465 Sickler Rd, Willow, NY 12495

  28+ Acres in Woodstock with Views Set at the foot of Mt. Tobias and surrounded by protected state and conservancy land on all sides, this exceptional 28+ acre parcel offers a rare opportunity to build with lasting privacy just minutes from the heart of Woodstock. An established driveway leads to a thoughtfully cleared build site where expansive valley and mountain views create a stunning backdrop

  Leigh Bokser Compass Greater NY, LLC

  465 Sickler Rd, Willow, NY 12495
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  /51

  $675,000

  $55K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,410 Sq Ft

  15 Lake View Dr, Lake Hill, NY 12448

  15 Lake View Drive | Lake Hill, NYA modern Catskills retreat with thoughtful architecture, natural beauty, and Cooper Lake just across the road.Set on three wooded acres in Lake Hill, this distinctive architect-designed contemporary offers a rare combination of privacy, design, and proximity to the best of the Hudson Valley. Tucked among mature trees and dramatic natural

  Mackenzie Grate The Machree Group, LLC

  15 Lake View Dr, Lake Hill, NY 12448
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  /61

  $889,000

  • 4 Beds
  • 3 Baths
  • 2,410 Sq Ft

  25-29 Mink Hollow Rd, Lake Hill, NY 12448

  Yan Wang REALTY ONE GROUP KEY

  25-29 Mink Hollow Rd, Lake Hill, NY 12448
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  /44

  $1,325,000

  $250K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,360 Sq Ft

  94 Chestnut Hill Rd, Woodstock, NY 12498

  A rare opportunity to own a truly special piece of the Hudson Valley. Nestled in the heart of Woodstock, NY, this iconic property offers 11.17 breathtaking acres of open meadows and sweeping mountain views that change beautifully with every season.The well-maintained 3-bedroom, 1-bath ranch house spans 1,360 square feet and offers comfortable single-level living with a warm, classic

  Henry Ford Coldwell Banker Village Green

  94 Chestnut Hill Rd, Woodstock, NY 12498
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  /19

  $799,000

  $60K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  2323 Glasco Turnpike, Woodstock, NY 12498

  A rare Byrdcliffe Colony offering, this 1911 Woodstock artist home sits just off Lower Byrdcliffe Road on a private half-acre of garden, lawn, patio, and woods. Rich with history and creative spirit, the original structure features the classic north-facing artist's window designed for painter's light, along with original beams and woodwork that speak to the home's early 20th-century

  Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  2323 Glasco Turnpike, Woodstock, NY 12498
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  /40

  $865,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft

  168 Cooper Lake Rd, Woodstock, NY 12498

  Set on one of Woodstock's most coveted country roads, this classic home offers the rare combination of timeless charm, privacy, and an exceptional location. Just moments from the heart of Woodstock, yet quietly removed, Cooper Lake Road is known for its scenic beauty, peaceful surroundings, and idyllic walks to nearby Cooper Lake.Originally portion of the house possibly dates to 1875 with

  Melissa Mayes Serhant LLC

  168 Cooper Lake Rd, Woodstock, NY 12498
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  /33

  $569,000

  $30K PRICE DROP

  • 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 Cocoa

  Michael Alpert Daniel Gale Sothebys Intl Rlty

  328 John Joy Rd, Woodstock, NY 12498
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  /33

  $300,000

  $195K PRICE DROP

  • Land
  • 5.4 Acres
  • $55,556 per Acre

  334 Yerry Hill Rd, Woodstock, NY 12498

  Tucked away just minutes from the heart of Woodstock, this exceptional 5-acre parcel offers a rare opportunity to create something truly special in one of the Hudson Valley's most sought-after locations. Surrounded by mature woods and natural beauty, the property features the serene Little Beaver Kill winding through the land along with seasonal mountain views from the upper elevation, creating

  Eliana Amodio Amodio Real Estate & Prop

  334 Yerry Hill Rd, Woodstock, NY 12498
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  /28

  $599,000

  $19K PRICE INCREASE

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  171 Van Dale Rd, Woodstock, NY 12498

  Step into this meticulously maintained and tastefully updated Woodstock split-level. Set way back from the road on one beautifully landscaped acre, featuring stately mature shade trees, ornamental shrubs, huge rhododendrons and plenty of sun. The interior of the home was just completely repainted including the garage. The main living level has been renovated to create a new, more modern great

  Brian Cafferty Halter Associates Realty

  171 Van Dale Rd, Woodstock, NY 12498
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  /44

  $599,000

  $150K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 2,355 Sq Ft

  11 Nordic Dr, Woodstock, NY 12498

  Welcome to this distinctive Woodstock retreat, a home shaped by the creativity and vision of the artists who have called it their own since 2001. Originally built in 1937, this charming mountaintop home has evolved over the years through thoughtful additions, including an impressive upper-level studio with a separate entrance, plus a vaulted deck overlooking the property's picturesque grounds.

  Lisa Halter HALTER ASSOCIATES REALTY INC

  11 Nordic Dr, Woodstock, NY 12498
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  /42

  $799,900

  $195K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,316 Sq Ft

  5 Maverick Terrace, Woodstock, NY 12498

  Tucked away on a peaceful, wooded lane, this inviting home offers the perfect blend of privacy, space, and convenience- just minutes to the heart of Woodstock.Inside, the home opens to an expansive living room anchored by a beautiful brick fireplace, creating a warm and inviting centerpiece for gatherings or quiet evenings. This oversized space includes a full bathroom and flows

  Dominique Musialkiewicz Howard Hanna Rand Realty

  5 Maverick Terrace, Woodstock, NY 12498
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  /27

  $349,000

  Pre-Foreclosure

  • 1 Bed
  • 1 Bath
  • 660 Sq Ft

  47 Baker Rd, Bearsville, NY 12409

  Escape to the woods in an Iconic Woodstock location! Tucked away on a quiet dead-end road, this eclectic one-bedroom cabin sits on just over 3 wooded acres filled with a beautiful mix of mature, towering trees. At the rear boundary is a mountainside stream. Full of character and rustic charm, the contemporary cabin features a large deck nestled among the trees--perfect for morning coffee,

  Daniel Winn Halter Associates Realty

  47 Baker Rd, Bearsville, NY 12409
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  /38

  $1,475,000

  • Land
  • 25.38 Acres
  • $58,117 per Acre

  132 Valley View Way, Woodstock, NY 12448

  The Ledges at Valley View High above the Beaverkill River, where the Catskills unfold in a sweep of peaks and light, lies The Ledges at Valley View - a design-ready estate site where modern architecture meets the mountain. Sited on more than 25 private acres, this south-facing ridgeline property captures cinematic views of Twin, Indian Head, Overlook, and Mount Guardian. The land adjoins more

  Margaret Bellar The Catskill Dream Team

  132 Valley View Way, Woodstock, NY 12448
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  /12

  $380,000

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  Unlisted Address

  Welcome to this spacious and beautifully maintained 2-bedroom condominium located in the highly desirable Melrose section of the Bronx. Situated within the private and gated Melrose Court Condominium community, this charming residence offers the perfect blend of comfort, convenience, and value.This inviting unit features two oversized king-size bedrooms, a bright Eat-In-Kitchen, a

  Christopher Webb Keller Williams NYC

  Unlisted Address
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  /31

  $1,990,000

  $510K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 2,978 Sq Ft

  177 Tinker St, Woodstock, NY 12498

  Fall in love with this artfully reimagined and expanded 1930 farmhouse, privately set on a gentle hill just moments from the heart of Woodstock. Rich in history and character, this special home was once owned by Michael Lang, the legendary founder of the 1969 Woodstock Festival—adding a rare and meaningful connection to the town's iconic past.Thoughtfully renovated, the home offers a

  Joan Capria Four Seasons Sotheby's Int'l R

  177 Tinker St, Woodstock, NY 12498
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  /2

  $349,000

  • Land
  • 5 Acres
  • $69,800 per Acre

  0 Abbey Rd Unit 20265115, Mt. Tremper, NY 12457

  In the famous town of Woodstock, NY, iconic Abbey Road offers a rare opportunity to own five acres of a remarkable piece of history and build your own future.Long before the music festival made the name ''Woodstock'' famous around the world, the town was a mecca for artists, musicians, actors, and writers. That creative spirit remains part of Woodstock's identity today. The town has its own

  Joyce Beymer Joyce Beymer Real Estate

  0 Abbey Rd Unit 20265115, Mt. Tremper, NY 12457
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  /49

  $2,300,000

  • 3 Beds
  • 3 Baths
  • 2,515 Sq Ft

  190 Lewis Hollow Rd, Woodstock, NY 12498

  Few properties embody the history, architecture, and landscape of Woodstock as completely as the Lewis House. On the side of Overlook Mountain, at the very top of Lewis Hollow Road, and surrounded by thousands of acres of protected forest on Overlook Mountain, this remarkable property has evolved over more than 220 years while retaining the quiet character that makes it truly timeless.The

  Harris Safier Compass Greater New York, LLC

  190 Lewis Hollow Rd, Woodstock, NY 12498
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  /29

  $2,400,000

  $100K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 2,978 Sq Ft

  175 Tinker St, Woodstock, NY 12498

  In the heart of Woodstock, this extraordinary 12+ acre Woodstock estate offers a rare blend of privacy, natural beauty, and village convenience. The property has a huge meadow/field in back and front offering peaceful pastoral views & potential. Bordering & with direct access to 76 acres of protected Comeau Park, the property invites you to explore miles of woodland trails, open meadows, the

  Joan Capria Four Seasons Sotheby's Int'l R

  175 Tinker St, Woodstock, NY 12498
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  /29

  $1,450,000

  $50K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 3,330 Sq Ft

  106 Mountain Laurel Ln, Woodstock, NY 12498

  Architectural. Iconic. Unrepeatable.Hidden on 1.73 private acres walking distance from the heart of Woodstock, this extraordinary estate is more than a home - it's a work of art. A rare fusion of a Frank Lloyd Wright–inspired contemporary residence and an original Buckminster Fuller–style geodesic dome, this is a property designed for those who appreciate architecture, creativity, and a life

  Ashley Olson Minard eXp Realty

  106 Mountain Laurel Ln, Woodstock, NY 12498
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  /6

  $184,900

  $40K PRICE DROP

  • 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
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  /35

  $1,200,000

  • Land
  • 74.16 Acres
  • $16,181 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
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  /51

  $1,200,000

  $100K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,060 Sq Ft

  5 & 7 Parker Ln, Woodstock, NY 12498

  Family Compound and/or Investment Property.There are 3 homes at 5 & 7 Parker Lane in Woodstock. The property is located only minutes from Main St in Woodstock.The 5 Parker Ln cottage has 1423 square feet with 2 bedrooms & 1 bathroom.7 Parker Ln has 2 homes on the lot. The 2-story home has 1231 square feet with 2 bedrooms & 1.5 bathrooms.The cabin at 7 Parker Ln has

  Richard Greenspan Ruth Gale Realty

  5 & 7 Parker Ln, Woodstock, NY 12498
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  /40

  $1,350,000

  $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,613 Sq Ft

  19 Blues Quarry, Woodstock, NY 12498

  Seventeen private acres, minutes from the heart of Woodstock. This 3-bedroom, 2.5-bath modern home pairs character with thoughtful separation of space: a fireplace-anchored great room, open kitchen, and dining area flow together on the main level alongside a versatile first-floor bedroom, ideal for guests, family, or a home office, served by a nearby full bath. Upstairs, the true primary suite

  Baris Demirel Serhant LLC

  19 Blues Quarry, Woodstock, NY 12498
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  /32

  $1,995,000

  $300K PRICE DROP

  • 7 Beds
  • 7 Baths
  • 4,331 Sq Ft

  2465 Glasco Turnpike, Woodstock, NY 12498

  Rare investment opportunity in Woodstock: a collection of five unique cottages on six wooded acres located just minutes from the Village's vibrant shops, dining, and nightlife. Each home boasts a distinct personality and peaceful forest views, and all five have been successfully rented with a combination of short- and long-term tenants. Possibilities include renting all five cottages or living in

  Lillian Kology Halter Associates Realty

  2465 Glasco Turnpike, Woodstock, NY 12498
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  /91

  $795,000

  Open Sat 12PM - 3PM

  • 5 Beds
  • 3 Baths
  • 2,044 Sq Ft

  4868 New York 212, Willow, NY 12495

  Income Opportunity! This property includes a transferable short-term rental license, excellent investment and income-producing potential.Beautifully renovated and thoughtfully updated with numerous high-end upgrades, see below, this versatile 4-5 bedroom, 3-bath home sits on 3.6 private acres with breathtaking views of Ohayo Mountain, Mount Guardian, Mount Tremper, and Panther Mountain.

  Ruti kabel Keller Williams Realty HV Nort

  4868 New York 212, Willow, NY 12495
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  /21

  $595,000

  Open Sun 3PM - 4PM

  • 2 Beds
  • 1 Bath
  • 1,338 Sq Ft

  357 Chestnut Hill Rd, Woodstock, NY 12498

  A STORYBOOK WOODSTOCK RETREAT IN THE WOODSSome homes provide shelter; others provide sanctuary. 357 Chestnut Hill Road is a sanctuary in the woods--a soulful Woodstock retreat where sunlight spills through skylights, pine glows underfoot, and the forest seems to lean in and whisper, ''stay awhile.''Set on 1.6 wooded acres with approximately 257 feet of road frontage, this

  Jacob Miles Brown Harris Stevens Hudson

  357 Chestnut Hill Rd, Woodstock, NY 12498
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  /50

  $2,375,000

  • 3 Beds
  • 3 Baths
  • 2,608 Sq Ft

  235 California Quarry Rd, Woodstock, NY 12498

  Architect-Designed Modern Retreat with Unparalleled Views Over Woodstock! Perched high above the Town of Woodstock, this rare and exceptional home offers a front-row seat to breathtaking panoramic views that stretch from the mountains to the Ashokan Reservoir. Designed by noted architect Les Walker, this contemporary residence evokes the magic of living in a luxurious treehouse—where every room

  Ellen Osgood Coldwell Banker Village Green

  235 California Quarry Rd, Woodstock, NY 12498
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  /50

  $1,795,000

  Open Sat 11AM - 1PM

  • 5 Beds
  • 7 Baths
  • 10,275 Sq Ft

  34 Elwyn Ln, Wood Stock, NY 12498

  Where history meets reinvention in Woodstock. From 19th-century barn to 21st-century landmark, come explore one of Woodstock's most extraordinary buildings. With part of the building dating to 1865, this extraordinary 10,000+ square foot barn conversion has been renovated to a high-end standard and is unlike any other structure in Woodstock, and quite possibly unlike any other building in the

  Michelle Bergkamp William Pitt Sotheby's Interna

  34 Elwyn Ln, Wood Stock, NY 12498
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  /40

  $579,000

  Open Sun 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,480 Sq Ft

  28 Ballantine Ln, Bearsville, NY 12409

  One of Woodstock's Original Handmade homes tucked away on almost 3 private acres at the end of a dead end lane. This 3 Bd/ 1.5 Ba home minutes to the center of Woodstock is the quintessential country retreat. Blending in with the natural Hudson Valley landscape this cedar and bluestone sided home leans into Woodstocks rich history of artists and builders utilizing their surroundings for sourcing

  Johanna Trimboli Halter Associates Realty

  28 Ballantine Ln, Bearsville, NY 12409
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  /26

  $349,000

  • Land
  • 3 Acres
  • $116,333 per Acre

  547 Glenford Wittenberg Rd, Bearsville, NY 12409

  Three acres available on Yankee Town Pond in Bearsville. Convenient to Woodstock yet only 15 minutes to the NYS Thruway. Minutes to the Ulster County Rail Trail w hiking and biking all at your fingertips. Love to fish? This is perfect. This lot is being subdivided from a larger parcel and will be a buildable lot with engineered plans for the house. The taxes and assessment reflect the entire

  Siobhan Scanlan Win Morrison Realty-K

  547 Glenford Wittenberg Rd, Bearsville, NY 12409
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  /45

  $1,200,000

  • 4 Beds
  • 4 Baths
  • 3,172 Sq Ft

  5 Downer Ln, Woodstock, NY 12498

  Set on six bucolic acres along one of Woodstock's most scenic country roads, this extraordinary barn residence captures sweeping views of Overlook Mountain, the timeless beauty of the Hudson Valley landscape, and the quiet rhythm of a true farm setting.Reimagined from a historic 19th-century barn that was carefully disassembled and relocated from farther north, the home is a remarkable

  Baris Demirel Serhant LLC

  5 Downer Ln, Woodstock, NY 12498
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  /18

  $425,000

  $14K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,106 Sq Ft

  216 Williams Ln, Kingston, NY 12401

  This charming craftsman is situated in the perfect location, set back from the road yet only minutes to main street Woodstock and historic uptown Kingston. Well maintained, this sturdy gem boasts pristine hardwood floors, original trim and details, spacious eat-in kitchen and central air conditioning throughout. Room sizes are ample and offer flexibility of use and space. Added bonuses are the

  Ryan Basten BHHS Nutshell Realty

  216 Williams Ln, Kingston, NY 12401

Showing Results 41 - 74, Page 2 of 2