Woodstock, NY Homes

• 

  

  

  /28

  $815,000 Under Contract

  • 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
• 

  

  

  /35

  $703,000 Sold Jul 24, 2025

  • 1,436 Sq Ft
  • $490/SF
  • 29 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1972

  23 Maurizi Ln, Woodstock, NY 12498

  Searching for the perfect blend of style, comfort, and convenience? It's here! This remarkable contemporary in one of Woodstock's most sought-after neighborhoods is ready to welcome you home. Set on a spacious and private 1.34-acre lot, this beautifully maintained four-bedroom, 2.5-bath residence offers a seamless mix of modern updates and inviting charm.The heart of the home is the

  Melissa Mayes Serhant LLC

  23 Maurizi Ln, Woodstock, NY 12498
• 

  

  

  /20

  Est $730,154 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,173 Sq Ft

  162 Sherman Rd, Kingston, NY 12401

  162 Sherman Rd, Kingston, NY 12401
• 

  

  

  /13

  $440,000

  • 1 Bed
  • 1 Bath
  • 841 Sq Ft

  57 Ohayo Mountain Rd, Woodstock, NY 12498

  THE EXCITEMENT AND CONVENIENCE OF WOODSTOCK VILLAGE LIVING! Adorable period bungalow moments from Tinker St. and all the dining, entertainment, shops, hiking, biking and golfing that Woodstock has to offer. This 1 BR, 1 BA charmer features an additional room/four-season sun porch, handsome masonry fireplace with river rock chimney, modern kitchen, a clawfoot tub, separate laundry area,

  Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

  57 Ohayo Mountain Rd, Woodstock, NY 12498
• 

  

  

  /30

  $735,000 Sold Jul 24, 2025

  • 2,280 Sq Ft
  • $322/SF
  • 105 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  86 Baumgarten Rd, Woodstock, NY 12498

  A One-of-a-Kind Renovated Barn & Creative Haven in WoodstockSet on three peaceful acres with a small stream and meandering mossy paths, this beautifully renovated 1910 barn blends historic charm with modern upgrades. Designed as both a unique home and an inspiring creative space, this property has been meticulously upgraded with radiant heating, all-new insulation, updated

  Baris Demirel Serhant LLC

  86 Baumgarten Rd, Woodstock, NY 12498
• 

  

  /33

  Est $674,996 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,430 Sq Ft

  4 Oriole Dr, Woodstock, NY 12498

  4 Oriole Dr, Woodstock, NY 12498
• 

  

  /51

  $1,750,000

  • 2 Beds
  • 2 Baths
  • 1,531 Sq Ft

  128 Newcut Rd, Bearsville, NY 12409

  Nestled atop your very own private mountaintop, this captivating retreat is the sanctuary you've been dreaming of. Enjoy 35 acres of serene woodland and breathtaking views. This residence is the ultimate escape for weekenders, outdoor enthusiasts, and creatives seeking the solitude necessary to ignite their next masterpiece.A peaceful haven with expansive mountain vistas, you'll find

  Heidi Maloney Four Seasons Sotheby's Int'l R

  128 Newcut Rd, Bearsville, NY 12409
• 

  

  /21

  $592,000 Sold Jul 23, 2025

  • 1,388 Sq Ft
  • $427/SF
  • 42 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1963

  20 Park Dr, Woodstock, NY 12498

  Discover the perfect blend of comfort and charm in this 4-bedroom, 2-bath split-level ranch nestled in Woodstock, NY. Thoughtfully designed, this home features an open-concept kitchen, living, and dining space that's perfect for both relaxed living and seamless entertaining. The kitchen offers a large island, quartz counter tops, stainless steel appliances, and ample cabinet space which makes

  Richard Vizzini Corcoran Country Living

  20 Park Dr, Woodstock, NY 12498
• 

  

  /30

  Est $669,677 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,499 Sq Ft

  104 Cardinal Ct, Woodstock, NY 12498

  104 Cardinal Ct, Woodstock, NY 12498
• 

  

  /24

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,607 Sq Ft

  311 Wittenberg Rd, Bearsville, NY 12409

  Welcome to the Stone Cottage A home that embodies the spirit of Woodstock with character, warmth and charm. Enter through the vintage kitchen, which opens into a charming dining area , the perfect setting for intimate dinners. The dining area flows seamlessly into the living room, creating the perfect gathering space for family and friends. Vaulted ceilings, wide board pine floors, a

  Anne Rajs Corcoran Country Living

  311 Wittenberg Rd, Bearsville, NY 12409
• 

  

  /39

  $380,000 Sold Jul 23, 2025

  • 1,568 Sq Ft
  • $242/SF
  • 46 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1964

  176 W Hurley Rd, Woodstock, NY 12498

  Situated on a generous lot in a fantastic location close to schools, shopping, restaurants, and easy commuting routes, this home is a rare find with tons of potential. A true diamond in the rough, this 1964 ranch home is just waiting for some cosmetic creativity to bring it to life. Step inside to discover a spacious, functional layout featuring a large living area, original hardwood floors, 3

  Gail Cadden Coldwell Banker Village Green

  176 W Hurley Rd, Woodstock, NY 12498
• 

  /2

  Est $731,520 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,945 Sq Ft

  195 Morey Hill Rd, Kingston, NY 12401

  195 Morey Hill Rd, Kingston, NY 12401
• 

  

  /25

  $739,000

  • 4 Beds
  • 3 Baths
  • 2,208 Sq Ft

  36-38 Ohayo Mountain Rd, Woodstock, NY 12498

  Welcome to The Mill House, nestled in the vibrant heart of Woodstock, NY—a delightful farmhouse that beautifully blends historic charm with modern comforts. Spanning 1,764 square feet, this inviting home includes three cozy bedrooms and two full bathrooms, offering a spacious layout for everyday living.As you wander through the lush gardens and cross a quaint bridge over a seasonal

  Sheena Lepez Compass Greater New York, LLC

  36-38 Ohayo Mountain Rd, Woodstock, NY 12498
• 

  

  /27

  $550,000 Sold Jul 18, 2025

  • 2,425 Sq Ft
  • $227/SF
  • 813 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1915

  623 Wittenberg Rd, Bearsville, NY 12409

  Circa 1915 Woodstock Victorian built to a high standard and grand scale, set amidst groves of towering pines and massive old-growth black locust trees. This stunner features 3-plus bedrooms, 2.5 baths and a multi-columned wraparound rocking chair porch with mahogany decking and original wainscoting. A small anteroom leads to two parlors in the original structure. High ceilings, bay windows and

  Peter Cantine Halter Associates Realty

  623 Wittenberg Rd, Bearsville, NY 12409
• 

  

  /33

  Est $681,128 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,678 Sq Ft

  282 Zena Rd, Kingston, NY 12401

  282 Zena Rd, Kingston, NY 12401
• 

  

  /30

  $575,000

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft

  233 Wittenberg Rd, Bearsville, NY 12409

  Picture yourself in this charming 1940 cottage with a roaring fire in its fieldstone double-height fireplace. If that doesn't capture your heart, the open living and dining areas with birch beamed ceilings will. Large expanses of windows flood the space with light, adding more charm essential to modern living. A wonderfully convenient full bath with claw-foot tub adds to the easy

  Henry Ford Coldwell Banker Village Green

  233 Wittenberg Rd, Bearsville, NY 12409
• 

  $1,100,000 Sold Jul 10, 2025

  • 4,400 Sq Ft
  • $250/SF
  • 52 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1910

  18 Maple Ln, Wood Stock, NY 12498

  Welcome to an exceptional investment opportunity nestled in the heart of the iconic Woodstock Village. This unique 4 family property offers an enticing package for investors, with potential for conversion into a boutique hotel. Spanning .75 acres, the property boasts a quartet of beautifully maintained apartments, each with its own charm and character.The crown jewel of the estate is a

  Heidi Maloney Four Seasons Sothebys Intl

  18 Maple Ln, Wood Stock, NY 12498
• 

  

  /16

  Est $297,220 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 717 Sq Ft

  318 Yerry Hill Rd, Woodstock, NY 12498

  318 Yerry Hill Rd, Woodstock, NY 12498
• 

  

  /39

  $1,985,000

  • 6 Beds
  • 3 Baths
  • 3,023 Sq Ft

  2320 Glasco Turnpike, Woodstock, NY 12498

  For the first time in its history, this 12-acre family estate—designed, built, and cherished by a prominent Woodstock family—comes to market. A rare opportunity for the next generation to build their own private estate or compound, walking distance to town. Complete with babbling brook, waterfall, two vintage Woodstock cottages and acres of woods to explore. A perfect retreat! to your dream

  George Denise Keller Williams Realty HV Nort

  2320 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /6

  $180,000 Sold Jul 03, 2025

  • Land
  • 14 Acres
  • $12,978 per Acre

  • 67 Days On Market

  Tbd Cooper Lake Rd, Bearsville, NY 12409

  Cooper Lake Road is an idyllic place to build your dream house and weekend getaway. 13+ acres of privacy and natural surroundings. A perfect blend of seclusion, convenience and an abundance of hard scrape materials add to the unique layout of the land. This property offers a desirable location and is only 5 minutes to the vibrant Village of Woodstock.

  Valerie Cashen Coldwell Banker Village Green

  Tbd Cooper Lake Rd, Bearsville, NY 12409
• 

  

  /35

  Est $826,349 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,156 Sq Ft

  460 Glenford Wittenberg Rd, Bearsville, NY 12409

  460 Glenford Wittenberg Rd, Bearsville, NY 12409
• 

  

  /13

  $220,000

  • Land
  • 5 Acres
  • $42,471 per Acre

  TBD Glasco Turnpike, Woodstock, NY 12498

  Located just 5 minutes from the center of Woodstock with its vibrant arts and dining scene, this 5+ acre parcel offers a landscape that feels both inspiring and practical. Dramatic rock outcroppings anchor the property, while the mix of mostly level and gently sloping areas provides excellent potential for building sites. A sun-dappled grassy ridge where light filters through the trees adds

  Briana Cermak BHHS HUDSON VALLEY PROP-WDST

  TBD Glasco Turnpike, Woodstock, NY 12498
• 

  

  /23

  $660,000 Sold Jul 01, 2025

  • 2,057 Sq Ft
  • $321/SF
  • 33 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1945

  58 Maverick Rd, Woodstock, NY 12498

  This enchanting Woodstock abode has a story dating back to 1875; first as a barn for the neighboring property and then as a dance studio. In the 1940's it was converted to this rare barn-style home that honors Woodstock's artistic vision and singularity. Meticulously updated over the years while preserving its vintage allure. Rustic yet gracious with an open vaulted great room anchored by a

  Ita McAteer BHHS HUDSON VALLEY PROP-WDST

  58 Maverick Rd, Woodstock, NY 12498
• 

  

  /35

  Est $1,312,249 Not Listed For Sale

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

  106 Mountain Laurel Ln, Woodstock, NY 12498

  106 Mountain Laurel Ln, Woodstock, NY 12498
• 

  

  /18

  $898,000

  • Land
  • 27 Acres
  • $33,027 per Acre

  TBD MacDaniel Rd, Bearsville, NY 12409

  Pollinator's Pathway in WoodstockDiscover 27+ acres of untouched beauty just steps from the Tibetan Monastery, Magic Meadow, and the trailheads to Meads Mountain and Overlook Mountain. A private, winding .4-mile driveway opens to a sunlit clearing alive with wildflowers and pollinator plants — a natural canvas awaiting your vision. With selective tree trimming, sweeping Catskill Mountain

  Genevieve Geaney Compass Greater New York, LLC

  TBD MacDaniel Rd, Bearsville, NY 12409
• 

  

  /24

  $1,194,000 Sold Jun 27, 2025

  • 1,923 Sq Ft
  • $621/SF
  • 31 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1976

  46 John Joy Rd, Woodstock, NY 12498

  Experience the Best of Upstate Living in the Heart of Woodstock!Discover this enchanting four-bedroom, two-bathroom home located on one of Woodstock's most sought-after streets. Privately set back from the road and directly across from the storied Thorne Preserve, with its scenic trails and sweeping views of Overlook Mountain, this turnkey residence offers both privacy and direct access

  Ashley Prather Corcoran Country Living

  46 John Joy Rd, Woodstock, NY 12498
• 

  

  /22

  Est $490,355 Not Listed For Sale

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

  2281 Glasco Turnpike, Woodstock, NY 12498

  2281 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /21

  $269,000

  • Land
  • 2.01 Acres
  • $133,831 per Acre

  TBD Carle Rd, Mt. Tremper, NY 12498

  Improved Land with Mountain Views - This prime 2 acre parcel is prepped to build your forever Catskill Mountain home. Improvements include driveway, expansive clearing, BOH approval for septic and the foundation for a garage or other accessory structure. Electric and cable are easily accessible off Carle Rd. Septic system has been designed, sited and permitted by the Board of Health. Timber

  Peter Cantine Halter Associates Realty

  TBD Carle Rd, Mt. Tremper, NY 12498
• 

  

  /24

  $469,500 Sold Jun 27, 2025

  • 682 Sq Ft
  • $688/SF
  • 33 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1930

  61 Ohayo Mountain Rd, Woodstock, NY 12498

  Quintessential Woodstock cottage right in town Live in the center of the iconic Woodstock with so much history and amazing Hudson Valley offerings.Tucked down a quiet drive is this perfectly appointed and move in ready 1 Bd/1 Ba home with loft for extra space. Hardwood floors throughout, custom bathroom, cute country kitchen, this sweet home has it all. Spiral staircase leads to loft space that

  Johanna Trimboli Halter Associates Realty

  61 Ohayo Mountain Rd, Woodstock, NY 12498
• 

  

  /22

  Est $459,274 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,040 Sq Ft

  2289 Glasco Turnpike, Woodstock, NY 12498

  2289 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /109

  $6,700,000

  • 3 Beds
  • 6 Baths
  • 2,417 Sq Ft

  125 Valley View Way, Lake Hill, NY 12448

  Welcome to Nature's Edge -- a Woodstock estate, where wilderness meets luxury. Perched at the end of a secluded private road, this modern mountain marvel offers unmatched privacy, serenity, and grandeur. Surrounded by natural woodscapes and native rock outcroppings, this 40 acre property sits adjacent to over 500 acres of forever wild NYC DEP land. The home itself, a Barry Price architectural

  Heidi Rothe Grist Mill Real Estate

  125 Valley View Way, Lake Hill, NY 12448
• 

  

  /77

  $2,000,000 Sold Jun 26, 2025

  • 2,801 Sq Ft
  • $714/SF
  • 19 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1874

  657 Zena Rd, Woodstock, NY 12498

  This historically significant 1700's Woodstock Farmstead and beautifully appointed guest house featured in Elle Decor Magazine combines classic American roots with modern country living and a touch of international elegance. Lovingly cared for both inside and out with thoughtfully designed updates and gardens, including an English-made Hartley greenhouse, abundant fruit trees and exquisite

  Amy Lonas Coldwell Banker Village Green

  657 Zena Rd, Woodstock, NY 12498
• 

  

  /34

  Est $557,355 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,201 Sq Ft

  50 Lower Byrdcliffe Rd, Woodstock, NY 12498

  50 Lower Byrdcliffe Rd, Woodstock, NY 12498
• 

  

  /27

  $300,000

  • 3 Beds
  • 1 Bath
  • 917 Sq Ft

  20 Overlook Dr, Woodstock, NY 12498

  Woodstock Ranch with Room to Make It Your OwnJust minutes from the heart of Woodstock, this single-level ranch combines charm, comfort, and exciting potential. The sunny living room flows to a cozy back sitting area, while three freshly painted bedrooms are ready for immediate enjoyment. The living area awaits your choice of flooring, and the kitchen offers the option to open a wall for

  Baris Demirel Serhant LLC

  20 Overlook Dr, Woodstock, NY 12498
• 

  

  /44

  $990,000 Sold Jun 26, 2025

  • 2,264 Sq Ft
  • $437/SF
  • 35 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1978

  14 Wardwell Ln, Woodstock, NY 12498

  Discover the perfect blend of charm and convenience at this beautiful Woodstock residence! With 4 bedrooms and 2.5 modern bathrooms, this home offers a sanctuary where comfort meets contemporary living. This home boasts a spacious open floor plan ideal for vibrant gatherings or tranquil relaxation.Step inside to find a large kitchen ready to inspire your culinary adventures, complemented by

  Stacey Anderson BHHS HUDSON VALLEY PROP-WDST

  14 Wardwell Ln, Woodstock, NY 12498
• 

  

  /29

  Est $881,215 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,807 Sq Ft

  46 Lower Byrdcliffe Rd, Woodstock, NY 12498

  46 Lower Byrdcliffe Rd, Woodstock, NY 12498
• 

  

  /17

  $2,200,000

  • 8 Beds
  • 10 Baths

  20 Country Club Ln, Wood Stock, NY 12498

  A Rare Opportunity in the Heart of Woodstock. Own a remarkable piece of Woodstock history. Once the site of the Woodstock Lodgeand The Pinecrest, this storied property invites you to step back in time whileenvisioning its next chapter.Set on 6.5 acres of scenic land with a mix of cleared grounds, wooded trails, and aseasonal stream, this property offers a rare combination of

  Kathryn Johnson William Pitt Sothebys Int Rlty

  20 Country Club Ln, Wood Stock, NY 12498
• 

  

  /47

  $949,000 Sold Jun 17, 2025

  • 1,684 Sq Ft
  • $564/SF
  • 57 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1985

  45 Rose Ln, Bearsville, NY 12409

  This is it! The country home you've always dreamed of is finally here. Located on nearly four sprawling acres, this exquisite home is filled with charm and beauty...Drive along Cooper Lake Road, Woodstock's most stunning road, to arrive at the idyllic Rose Lane. At the end of this quiet, private lane is your own personal oasis.... Follow the long driveway to your country dream home, designed

  Greg Berardi Berardi Realty

  45 Rose Ln, Bearsville, NY 12409
• 

  

  /32

  Est $480,859 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,253 Sq Ft

  21 Cedar Way, Woodstock, NY 12498

  21 Cedar Way, Woodstock, NY 12498
• 

  

  /13

  $124,900

  • Land
  • 2.00 Acres
  • $62,450 per Acre

  5299 New York 212, Mount Tremper, NY 12457

  Two acres of land in the Catskill Mountain foothills with incredible views and close proximity to popular destinations like the Phoenicia Diner, Emerson Spa & Kaleidoscope, and Esopus creek swimming and nature trails - all just five minutes away. In just a 15 minute drive, you'll find the shopping, dining, and local arts scene of Woodstock or the Bellayre ski resort, among countless other

  Terence Lynch Century 21 New West

  5299 New York 212, Mount Tremper, NY 12457

Showing Results 81 - 120, Page 3 of 18