Woodstock, NY Homes

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  /38

  $689,000

  • 2 Beds
  • 3 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 principles and practicality. The perfect country escape, yet within easy access to restaurants, shopping and all outdoor

  

  Win Morrison

  Win Morrison Realty

  (845) 470-4906

  18 Country Club Ln, Woodstock, NY 12498
• Explore Woodstock

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  /20

  $8,783 per month

  • 7 Beds
  • 5.5 Baths
  • 3,799 Sq Ft
  • Condo for Rent

  21 Abbey Rd Unit ID1241292P, Mount Tremper, NY 12457

  Nestled in the heart of tranquil upstate New York, Abbey Road Farmhouse offers an idyllic escape just 2.5 hours from NYC. Feel at home in the main house, which boasts 5 beds and 3.5 baths, or in the charming 2-bed, 2-bath cottage.The main house features a cozy living room, modern kitchen, office, and gym. The spacious living room is adorned with large windows framing picturesque views,

  21 Abbey Rd Unit ID1241292P, Mount Tremper, NY 12457
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  /33

  $225,000 Sold Aug 26, 2025

  23 Cottonwood Ln, Woodstock, NY 12498

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft
  • Built 1966

  Last Sold Summary

  • 36% Below List Price
  • $320/SF
  • 61 Days On Market

  Current Estimated Value $274,842

  Last Listing Agent James Murphy Patty Conti Realty Group LLC

  23 Cottonwood Ln, Woodstock, NY 12498
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  /24

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft

  18 Vandermark Rd, Woodstock, NY 12498

  18 Vandermark Rd, Woodstock, NY 12498
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  /62

  $1,850,000

  • 3 Beds
  • 3 Baths
  • 3,319 Sq Ft

  9 Cooper Lake Rd, Bearsville, NY 12409

  A secluded mountain escape awaits you in one of Woodstock's preeminent neighborhoods. Tucked away on Cooper Lake Road—famous for its dramatic lake and mountain vistas—this home offers privacy while being just minutes from the town's legendary music venues, galleries, and fine dining. The welcoming front entry of this home unfolds to an airy and open layout accented by soaring beamed ceilings and

  

  Amy Lonas

  Coldwell Banker Village Green

  (845) 932-1530

  9 Cooper Lake Rd, Bearsville, NY 12409
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  /35

  $4,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,833 Sq Ft
  • House for Rent

  180 Yerry Hill Rd, Woodstock, NY 12498

  With its very close proximity to Woodstock village, this is the perfect location if you're looking to engage in the vibrant artistic community yet yearn for woodsy privacy! This elegant yet simple home is very cozy with a modern kitchen, wood floors throughout, a family room in addition to the living room. and an office space. Three bedrooms are upstairs: a very large primary bedroom with 1/2

  Sylvie Ross Halter Associates Realty

  180 Yerry Hill Rd, Woodstock, NY 12498
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  /37

  $825,000 Sold Nov 18, 2025

  16 Marko Grove, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 2,350 Sq Ft
  • Built 1964

  Last Sold Summary

  • 4% Above List Price
  • $351/SF
  • 17 Days On Market

  Last Listing Agent Leslie Foti Coldwell Banker Village Green

  16 Marko Grove, Woodstock, NY 12498
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  /24

  Est $498,760 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,279 Sq Ft

  296 Yerry Hill Rd, Woodstock, NY 12498

  296 Yerry Hill Rd, Woodstock, NY 12498
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  /24

  $795,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,992 Sq Ft

  1671 Glasco Turnpike, Woodstock, NY 12498

  Renovated Mid-Century Modern Minutes from Woodstock Located just outside the heart of Woodstock, this thoughtfully reimagined mid-century split-level home was transformed by an award-winning architectural designer, blending clean contemporary design with timeless upstate charm. With 3 bedrooms and 2 full bathrooms, the home has been expanded and upgraded from top to bottom offering the perfect

  

  Leigh Bokser

  Compass Greater NY, LLC

  (845) 599-1296

  1671 Glasco Turnpike, Woodstock, NY 12498
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  /23

  $4,700 per month

  • 5 Beds
  • 3 Baths
  • 2,950 Sq Ft
  • House for Rent

  41 Park Dr, Woodstock, NY 12498

  Situated on nearly an acre of manicured green grass, fruit trees, and mountainous woods in the heart of the Woodstock NY in the Catskills, this roughly 3,000 square foot 5-bedroom, 3-bathroom home is the perfect balance between peaceful nature and the higher-end comforts of being near the city. The house has a big master bedroom with large windows facing nature and easily fits a king size bed.

  Jerry Weiss Pietro Altomare Realty

  41 Park Dr, Woodstock, NY 12498
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  /41

  $892,000 Sold Nov 04, 2025

  8 Pine Grove St, Woodstock, NY 12498

  • 5 Beds
  • 4 Baths
  • 2,426 Sq Ft
  • Built 1920

  Last Sold Summary

  • 10% Below List Price
  • $368/SF
  • 77 Days On Market

  Last Listing Agent Judy Steinfeld Halter Associates Realty

  8 Pine Grove St, Woodstock, NY 12498
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  /31

  Est $674,743 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,756 Sq Ft

  328 Ohayo Mountain Rd, Woodstock, NY 12498

  328 Ohayo Mountain Rd, Woodstock, NY 12498
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  /25

  $479,500 Pending

  • 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

  (845) 419-4948

  44 Overlook Dr, Woodstock, NY 12498
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  /49

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,342 Sq Ft
  • House for Rent

  299 Wittenberg Rd, Bearsville, NY 12409

  Luxury 2-Bed, 2-Bath Spa Retreat on over 6 Acres - Jet Tub, Sauna, Fire Pit & Handcrafted Natural Design Just 10 minutes from the heart of Woodstock and 5 minutes from the Bearsville Theater and restaurants, this stunning 2-bedroom, 2-bath retreat combines luxury, craftsmanship, and nature in perfect harmony. Every detail has been thoughtfully designed using only natural materials - stone, wood,

  Susanna Scott-Mitchell Compass Greater NY, LLC

  299 Wittenberg Rd, Bearsville, NY 12409
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  $1,100,000 Sold Jul 10, 2025

  18 Maple Ln, Wood Stock, NY 12498

  • 6 Beds
  • 6 Baths
  • 4,400 Sq Ft
  • Built 1910

  Last Sold Summary

  • 14% Below List Price
  • $250/SF
  • 52 Days On Market

  Current Estimated Value $1,171,202

  Last Listing Agent Heidi Maloney Four Seasons Sothebys Intl

  18 Maple Ln, Wood Stock, NY 12498
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  /33

  Est $890,820 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,109 Sq Ft

  73 Ratterman Rd, Woodstock, NY 12498

  73 Ratterman Rd, Woodstock, NY 12498
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  /47

  $1,250,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,634 Sq Ft

  46 Rose Ln, Bearsville, NY 12409

  Tucked away on a quiet forested road just minutes from the heart of Woodstock, this custom-designed modern cabin is a hidden gem with high-end finishes, smart home tech, and natural beauty at every turn. Located on picturesque Rose Lane, the property is bordered by native trees, a spring-fed pond, and the flowing waters of the Sawkill Creek—creating a private, serene setting with breathtaking

  

  Catherine Quintard

  Compass Greater NY, LLC

  (845) 757-6445

  46 Rose Ln, Bearsville, NY 12409
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  /30

  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 2,116 Sq Ft
  • House for Rent

  20 Sherman Rd, Woodstock, NY 12498

  A great opportunity to live, work, and play in Woodstock! This charming, 3 bed, 2 bath home, is located a stone's throw away from downtown Woodstock and offers a wonderful private spot to enjoy all the area has to offer. With plenty of light and open plan, this home features a first floor bedroom and full bathroom. Going up the renovated stairs, you will find two bedrooms and a newly added

  Victoria Stent Coldwell Banker Village Green

  20 Sherman Rd, Woodstock, NY 12498
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  $4,600,000 Sold Aug 25, 2025

  18 Striebel Rd, Woodstock, NY 12498

  • 4 Beds
  • 4 Baths
  • 3,899 Sq Ft
  • Built 1914

  Last Sold Summary

  • 8% Below List Price
  • $1,180/SF
  • 99 Days On Market

  Current Estimated Value $4,773,838

  Last Listing Agent Kathryn Johnson William Pitt Sothebys Int Rlty

  18 Striebel Rd, Woodstock, NY 12498
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  /37

  Est $1,004,886 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,152 Sq Ft

  53 Blueberry Hill Rd, Bearsville, NY 12409

  53 Blueberry Hill Rd, Bearsville, NY 12409
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  /13

  $99,990 Under Contract

  • Land
  • 2 Acres
  • $49,995 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 options

  

  Terence Lynch

  Century 21 New West

  (845) 203-2297

  5299 New York 212, Mount Tremper, NY 12457
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  /28

  $5,500 per month

  • 4 Beds
  • 2.5 Baths
  • 2,333 Sq Ft
  • House for Rent

  10 Purdy Hollow Rd, Woodstock, NY 12498

  Fully Furnished Winter Seasonal Rental Opportunity Embrace winter in the Catskills in this fully furnished, beautifully renovated cedar contemporary home, ideally located in the peaceful hamlet of Zena, just five minutes from the vibrant town of Woodstock. Situated on three private acres and directly across from the 60-acre Thorn Preserve, this sanctuary offers breathtaking views of the Catskill

  Sarah Stoudt Coldwell Banker Village Green

  10 Purdy Hollow Rd, Woodstock, NY 12498
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  /20

  $325,000 Sold Nov 04, 2025

  57 Overlook Dr, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 1,177 Sq Ft
  • Built 1955

  Last Sold Summary

  • 1% Below List Price
  • $276/SF
  • 33 Days On Market

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

  57 Overlook Dr, Woodstock, NY 12498
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  /41

  Est $631,580 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,842 Sq Ft

  47 van de Bogart Rd, Woodstock, NY 12498

  47 van de Bogart Rd, Woodstock, NY 12498
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  /28

  $259,000 Under Contract

  • 1 Bath
  • 475 Sq Ft

  259 Silver Hollow Rd, Willow, NY 12495

  Tucked along a quiet, storybook country road, this enchanting 3-seasons creekside studio cabin is the perfect Catskills retreat. Brimming with warmth and character, the 475-square-foot hideaway features vaulted ceilings, hand-hewn beams, and rich wood paneling, creating a timeless, rustic feel. Adding even more appeal, the property includes a transferable short-term rental permit, offering an

  Leslie Foti Coldwell Banker Village Green

  259 Silver Hollow Rd, Willow, NY 12495
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  /8

  $2,050 per month

  • 2 Beds
  • 1 Bath
  • 898 Sq Ft
  • House for Rent

  79 Reynolds Ln, Bearsville, NY 12409

  Adorable 2 bedroom cottage available for year round rental. Beautiful spot, walk to Bearsville with an open field across the street, a lovely stream beyond and plenty of parking. The home is lightly furnished. Tenant to pay utilities

  Mercedes Ross Coldwell Banker Village Green

  79 Reynolds Ln, Bearsville, NY 12409
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  /34

  $800,000 Sold Dec 17, 2025

  3251 Route 212, Bearsville, NY 12409

  • 2 Beds
  • 2 Baths
  • 1,850 Sq Ft
  • Built 1925

  Last Sold Summary

  • 3% Above List Price
  • $432/SF
  • 62 Days On Market

  Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

  3251 Route 212, Bearsville, NY 12409
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  /40

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  3906 New York 212, Lake Hill, NY 12448

  3906 New York 212, Lake Hill, NY 12448
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  /35

  $799,000

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

  4 Munchkin Ln, Kingston, NY 12401

  Highwoods Haven rests on just over two quiet acres where sunlight filters through tall hardwoods and birdsong fills the air. Although the setting feels miles from anywhere, the property lies barely five minutes from Woodstock's Village Green and within a short, scenic drive of Kingston and Saugerties. A comprehensive 2021 renovation infused the four-bedroom, two-bath residence with modern comfort

  Leslie Foti Coldwell Banker Village Green

  4 Munchkin Ln, Kingston, NY 12401
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  /10

  $2,550 per month

  • 3 Beds
  • 1 Bath
  • 945 Sq Ft
  • House for Rent

  81 Reynolds Ln, Bearsville, NY 12409

  Year round rental in a Quintessential Woodstock cottage with 3 bedrooms, high ceilings, open floor plan, wood floors and bathed in sunlight. This bright and open home is in a lovely quiet country setting on the edge of the village. Tenant pays utilities

  Mercedes Ross Coldwell Banker Village Green

  81 Reynolds Ln, Bearsville, NY 12409
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  /27

  $370,000 Sold Oct 31, 2025

  38 Arnold Dr, Woodstock, NY 12498

  • 3 Beds
  • 1.5 Baths
  • 1,365 Sq Ft
  • Built 1961

  Last Sold Summary

  • 14% Below List Price
  • $271/SF
  • 48 Days On Market

  Last Listing Agent Laura Prince Hudson Dwellings Realty

  38 Arnold Dr, Woodstock, NY 12498
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  /26

  Not Listed For Sale

  TBD Yerry Hill Rd, Woodstock, NY 12498

  TBD Yerry Hill Rd, Woodstock, NY 12498
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  /28

  $925,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,998 Sq Ft

  64 Lower Byrdcliffe Rd, Woodstock, NY 12498

  This historic Woodstock home, complete with a legal short-term rental license, is ready for its next chapter. Just a short distance from the iconic village green and the heart of Woodstock, this recently restored 1897 Arts and Crafts farmhouse offers both privacy and convenience on one of the town's most desirable streets - a truly rare combination that seldom becomes available. The charming

  Victoria Stent Coldwell Banker Village Green

  64 Lower Byrdcliffe Rd, Woodstock, NY 12498
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  /13

  $2,900 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  88 Rock City Rd Unit 90, Woodstock, NY 12498

  Nestled just a half mile from the iconic Woodstock Village Green, this freestanding 2-bedroom, 1,200 sq ft cottage offers the perfect blend of privacy, comfort, and convenience. Whether you're seeking a furnished or unfurnished rental, this serene escape is move-in ready and thoughtfully appointed. Step into a sunlit great room featuring vaulted beamed ceilings, a stone fireplace with

  Michael Shaughnessy Halter Associates Realty Inc

  88 Rock City Rd Unit 90, Woodstock, NY 12498
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  $1,150,000 Sold Aug 22, 2025

  11 Louie Way, Woodstock, NY 12498

  • 2 Beds
  • 2 Baths
  • 2,209 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Above List Price
  • $521/SF
  • 31 Days On Market

  Last Listing Agent Gary Heckelman Halter Associates Realty Inc

  11 Louie Way, Woodstock, NY 12498
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  Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,545 Sq Ft

  290 Mink Hollow Rd, Woodstock, NY

  290 Mink Hollow Rd, Woodstock, NY
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  /52

  $1,340,000

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  66 Plochmann Ln, Woodstock, NY 12498

  So close yet so far away! Walk to town from your totally private and like-new timber frame home with soaring 23-foot ceilings and walls of windows to bring nature in. As you enter from one of Woodstock's most coveted roads, through the stately pillars, you will feel a sense of tranquility with nature on this 9.94-acre lot that is just a half mile from the village of Woodstock and less than a half

  Mercedes Ross Coldwell Banker Village Green

  66 Plochmann Ln, Woodstock, NY 12498
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  /16

  $2,600 per month

  • 2 Beds
  • 1.5 Baths
  • 1,287 Sq Ft
  • House for Rent

  259 John Joy Rd, Woodstock, NY 12498

  2 bedroom farmhouse on beautiful John Joy Road available October 1st through May 31st for 6 months or more. Set toward the back of a 3 acre meadow far from the road and bordering a beautiful forest, this charming home is just a mile or so from Woodstock Day School and 3 miles to the Zena Democratic School. Relax on the deck and take in the change of seasons and wildlife that meanders through the

  Sean Zimmerman Halter Associates Realty

  259 John Joy Rd, Woodstock, NY 12498
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  /38

  $620,000 Sold Sep 26, 2025

  3 Oriole Dr, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 2,158 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Above List Price
  • $287/SF
  • 32 Days On Market

  Last Listing Agent Mario Geissler Four Seasons Sotheby's Int'l R

  3 Oriole Dr, Woodstock, NY 12498
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  /35

  Est $1,219,313 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,075 Sq Ft

  2680 Glasco Turnpike, Wood Stock, NY 12498

  2680 Glasco Turnpike, Wood Stock, NY 12498

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