Woodstock, NY Homes

• 

  

  

  /38

  $897,250

  Sold May 01, 2026

  52 Meher Cir, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $408/SF
  • 28 Days On Market

  Current Estimated Value $892,178

  Last Listing Agent Steven DiLorenzo Compass Greater NY LLC

  52 Meher Cir, Woodstock, NY 12498
• 

  

  

  /32

  Est $1,491,903

  Not Listed For Sale

  54 Shultis Farm Rd, Bearsville, NY 12409

  • 5 Beds
  • 4 Baths
  • 3,722 Sq Ft
  • Built 1952

  54 Shultis Farm Rd, Bearsville, NY 12409

  Last Sold Summary

  • 35 Days On Market
• 

  

  

  /19

  $425,000

  Under Contract

  • 2 Baths
  • 959 Sq Ft

  125 Tinker St, Woodstock, NY 12498

  Prime Income Property | Vacant Woodstock 2-Family OpportunityDelivered Vacant--maximize your portfolio's ROI from day one. Savvy investors and owner-occupants, take note: this exceptionally located 2-family property offers immediate cash-flow potential with zero tenant transition hassle. Set your own market-rate rents right away in the high-demand Woodstock Hamlet rental market. The

  Peter Cantine Halter Associates Realty

  125 Tinker St, Woodstock, NY 12498
• 

  $810,000

  Sold Oct 24, 2025

  11 Grogkill Rd, Willow, NY 12495

  • 3 Beds
  • 2.5 Baths
  • 3,080 Sq Ft
  • Built 2006

  Last Sold Summary

  • 42% Below List Price
  • $263/SF
  • 78 Days On Market

  Current Estimated Value $1,056,042

  Last Listing Agent Sharon Breslau BHHS Hudson Valley Properties

  11 Grogkill Rd, Willow, NY 12495
• 

  

  

  /32

  Est $2,564,586

  Not Listed For Sale

  34 Vandebogart Rd, Woodstock, NY 12498

  • 4 Beds
  • 4.5 Baths
  • 3,954 Sq Ft
  • Built 2007

  34 Vandebogart Rd, Woodstock, NY 12498

  Last Sold Summary

  • 81 Days On Market
• 

  

  /49

  $2,150,000

  Pending

  • 5 Beds
  • 5.5 Baths
  • 5,163 Sq Ft

  15-17 Broadview Rd, Woodstock, NY 12498

  This exceptional Woodstock property offers a rare blend of privacy and convenience, just minutes from the village center. The modern main residence features 3 ensuite bedrooms, complemented by a studio and a separate guest house, for a total of 5 bedrooms and 5.5 baths across 4,000+ square feet--an uncommon offering this close to town. Designed for both everyday living and entertaining, the home

  Baris Demirel Serhant LLC

  15-17 Broadview Rd, Woodstock, NY 12498
• 

  $607,000

  Sold Jan 23, 2026

  18 Niles Dr, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Built 1965

  Last Sold Summary

  • 11% Above List Price
  • $305/SF
  • 29 Days On Market

  Current Estimated Value $607,754

  Last Listing Agent Laurel Sweeney BHHS Nutshell Realty

  18 Niles Dr, Woodstock, NY 12498
• 

  

  /31

  Est $962,225

  Not Listed For Sale

  38 Vandebogart Rd, Woodstock, NY 12498

  • 4 Beds
  • 3.5 Baths
  • 3,914 Sq Ft
  • Built 1920

  38 Vandebogart Rd, Woodstock, NY 12498

  Last Sold Summary

  • 12 Days On Market
• 

  

  /14

  $395,000

  $45K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 841 Sq Ft

  57 Ohayo Mountain Rd, Woodstock, NY 12498

  CHARMING WOODSTOCK VILLAGE COTTAGE - NEW ROOF AND GUTTERS NOW INCLUDED! Here's your chance to own an authentic Woodstock retreat in the heart of the Hudson Valley's most coveted small town.Just moments from the village center, this cozy, character-filled cottage offers the perfect blend of vintage charm and everyday comfort. The one-bedroom, one-bath layout is thoughtfully expanded by a

  Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

  57 Ohayo Mountain Rd, Woodstock, NY 12498
• 

  

  /39

  $585,000

  Sold Sep 12, 2025

  148 Hutchin Hill Rd, Shady, NY 12409

  • 2 Beds
  • 1 Bath
  • 1,039 Sq Ft
  • Built 1949

  Last Sold Summary

  • 2% Below List Price
  • $563/SF
  • 76 Days On Market

  Current Estimated Value $597,712

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

  148 Hutchin Hill Rd, Shady, NY 12409
• 

  

  /22

  Est $657,645

  Not Listed For Sale

  6 Allen Dr, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 2,106 Sq Ft
  • Built 1969

  6 Allen Dr, Woodstock, NY 12498

  Last Sold Summary

  • 13 Days On Market
• 

  

  /38

  $725,000

  • 2 Beds
  • 1 Bath
  • 1,067 Sq Ft

  18 Playhouse Ln, Woodstock, NY 12498

  Perfectly situated in the heart of Woodstock Village, this charming move-in-ready single-level country cottage offers comfort, character, and flexibility just moments from the town's renowned restaurants, galleries, boutiques, markets, music venues, and year-round attractions. The home features two spacious bedrooms, each with walk-in closets, random-width pegged hardwood floors, recessed

  Brenda Graf Corcoran Country Living

  18 Playhouse Ln, Woodstock, NY 12498
• 

  

  /42

  $590,000

  Sold May 13, 2026

  83 Ratterman Rd, Woodstock, NY 12498

  • 5 Beds
  • 2.5 Baths
  • 1,939 Sq Ft
  • Built 1964

  Last Sold Summary

  • 8% Below List Price
  • $304/SF
  • 97 Days On Market

  Current Estimated Value $606,266

  Last Listing Agent Edwin Maldonado Howard Hanna Rand Realty

  83 Ratterman Rd, Woodstock, NY 12498
• 

  

  /35

  Est $619,092

  Not Listed For Sale

  15 Niles Dr, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 1966

  15 Niles Dr, Woodstock, NY 12498

  Last Sold Summary

  • 33 Days On Market
• 

  

  /24

  $549,000

  • 2 Beds
  • 1.5 Baths
  • 1,191 Sq Ft

  208 Tinker St, Woodstock, NY 12498

  TURNKEY WOODSTOCK COTTAGE. A deep violet front door opens to a rustic ''mudroom'' with a bluestone floor and a closet for your outdoor gear. The kitchen, with its Liebherr and Bosch appliances, custom cabinetry with pantry, stylish lighting fixtures, radiant heat, beamed ceiling with a skylight - leads into a light-filled Living/Dining/Den space with original wide-plank wood floors, ceiling fan

  Marilyn Heir BHHS HUDSON VALLEY PROP-WDST

  208 Tinker St, Woodstock, NY 12498
• 

  

  /47

  $544,000

  Sold Mar 09, 2026

  2059 Glasco Turnpike, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 1,561 Sq Ft
  • Built 1965

  Last Sold Summary

  • 1% Below List Price
  • $348/SF
  • 23 Days On Market

  Current Estimated Value $551,703

  Last Listing Agent Amy Lonas Coldwell Banker Village Green

  2059 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /29

  Est $567,733

  Not Listed For Sale

  12 Niles Dr, Woodstock, NY 12498

  • 3 Beds
  • 3 Baths
  • 2,029 Sq Ft
  • Built 1970

  12 Niles Dr, Woodstock, NY 12498

  Last Sold Summary

  • 97 Days On Market
• 

  

  /29

  $399,999

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  21 Overlook Dr, Woodstock, NY 12498

  A sweet bright ranch in a friendly neighborhood, only a skip and a jump from the center of Woodstock. Located on one of the largest lots in the area with several majestic oaks and lots of room to roam. There's also space for a sizeable garden. Inside you will find an open plan living and dining area with an adjacent kitchen. The previous garage was converted into a large living space. On the

  Jasmine Jordaan Halter Associates Realty

  21 Overlook Dr, Woodstock, NY 12498
• 

  

  /27

  $550,000

  Sold Jul 18, 2025

  623 Wittenberg Rd, Bearsville, NY 12409

  • 3 Beds
  • 2.5 Baths
  • 2,425 Sq Ft
  • Built 1915

  Last Sold Summary

  • 31% Below List Price
  • $227/SF
  • 813 Days On Market

  Last Listing Agent Peter Cantine Halter Associates Realty

  623 Wittenberg Rd, Bearsville, NY 12409
• 

  

  /35

  Est $677,148

  Not Listed For Sale

  157 Van Dale Rd, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,259 Sq Ft
  • Built 1965

  157 Van Dale Rd, Woodstock, NY 12498

  Last Sold Summary

  • 16 Days On Market
• 

  

  /20

  $649,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,364 Sq Ft

  87 Witchtree Rd, Woodstock, NY 12498

  Privately situated on corner lot, this stylish and thoughtfully maintained Woodstock home is surrounded by mature hardwoods and evergreens, with beautiful western exposure that fills the interior with warm natural light. This three-bedroom, two-and-a-half-bath home offers a comfortable and functional layout with a perfect balance of open space and private living areas. Recent improvements include

  Sheila Wise The Kinderhook Group, Inc.

  87 Witchtree Rd, Woodstock, NY 12498
• 

  

  /51

  $609,825

  Sold Oct 07, 2025

  916 Zena Rd, Woodstock, NY 12498

  • 3 Beds
  • 3 Baths
  • 2,442 Sq Ft
  • Built 1964

  Last Sold Summary

  • 2% Above List Price
  • $250/SF
  • 36 Days On Market

  Current Estimated Value $641,721

  Last Listing Agent Amy Lonas Coldwell Banker Village Green

  916 Zena Rd, Woodstock, NY 12498
• 

  

  /27

  Est $620,356

  Not Listed For Sale

  3 Niles Dr, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft
  • Built 1966

  3 Niles Dr, Woodstock, NY 12498

  Last Sold Summary

  • 6 Days On Market
• 

  

  /32

  $799,000

  Open Sun 11AM - 2PM $100K PRICE INCREASE

  • 4 Beds
  • 2.5 Baths
  • 2,480 Sq Ft

  5 Lazy Brook Ln, Woodstock, NY 12498

  NEW NEW NEW! If you thought you have seen 5 Lazy Brook Lane, think again! This home is owned by a renowned architect and he has done a complete redesign! Mood, space, and finishes combine to create the ideal modern ranch. Coming to this 4 bedroom 3 bath home, you will first notice the new facade with white washed wood panels and a huge plate glass window where the unsightly bay window used to be.

  Richard Stoll Halter Associates Realty Inc

  5 Lazy Brook Ln, Woodstock, NY 12498
• 

  

  /41

  $485,000

  Sold Nov 19, 2025

  3523 Route 212, Bearsville, NY 12409

  • 3 Beds
  • 1.5 Baths
  • 1,506 Sq Ft
  • Built 1905

  Last Sold Summary

  • 2% Below List Price
  • $322/SF
  • 101 Days On Market

  Current Estimated Value $493,675

  Last Listing Agent Peter Cantine Halter Associates Realty

  3523 Route 212, Bearsville, NY 12409
• 

  

  /20

  Est $737,754

  Not Listed For Sale

  162 Sherman Rd, Kingston, NY 12401

  • 3 Beds
  • 2 Baths
  • 2,173 Sq Ft
  • Built 1966

  162 Sherman Rd, Kingston, NY 12401

  Last Sold Summary

  • 5 Days On Market
• 

  

  /39

  $1,495,000

  Open Sat 10AM - 12PM

  • 3 Beds
  • 2.5 Baths
  • 2,731 Sq Ft

  41 Wittenberg Rd, Bearsville, NY 12409

  Hidden among the trees and just seven minutes from the center of Woodstock, this 1970s contemporary feels like a private creative compound, untouched in all the right ways. Set on 2 wooded acres with the Sawkill Creek at the rear of the property, the home unfolds through a series of unexpected spaces and strong architectural moments. A dramatic sunken living room anchors the house, centered

  Michelle Bergkamp William Pitt Sotheby's Interna

  41 Wittenberg Rd, Bearsville, NY 12409
• 

  

  /35

  $775,000

  Sold Mar 16, 2026

  4 Munchkin Ln, Kingston, NY 12401

  • 4 Beds
  • 2 Baths
  • 1,948 Sq Ft
  • Built 1977

  Last Sold Summary

  • 3% Below List Price
  • $398/SF
  • 98 Days On Market

  Current Estimated Value $760,390

  Last Listing Agent Leslie Foti Coldwell Banker Village Green

  4 Munchkin Ln, Kingston, NY 12401
• 

  

  /47

  Est $895,186

  Not Listed For Sale

  36 Lund Ct, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,673 Sq Ft
  • Built 1984

  36 Lund Ct, Woodstock, NY 12498

  Last Sold Summary

  • 42 Days On Market
• 

  

  /15

  $575,000

  • Land
  • 37 Acres
  • $15,541 per Acre

  00 Lauren Ct, Woodstock, NY 12498

  This spectacular 35+ acre property is a rare offering. Comprised of two separate lots with access points on both Lauren Ct and Church Rd - an open canvas for your boldest vision. Whether you're a developer seeking your next signature project or a homeowner dreaming of a private sanctuary, this land invites imagination and promises possibility. A harmonious blend of mature woodlands, sunlit

  Melissa Zoe Hirsch Coldwell Banker Village Green

  00 Lauren Ct, Woodstock, NY 12498
• 

  /2

  $1,550,000

  Sold Oct 15, 2025

  16 Juniper Ln, Woodstock, NY 12498

  • 3 Beds
  • 2.5 Baths
  • 3,076 Sq Ft
  • Built 1982

  Last Sold Summary

  • 15% Below List Price
  • $504/SF
  • 89 Days On Market

  Current Estimated Value $1,610,779

  Last Listing Agent Victoria Stent Coldwell Banker Village Green

  16 Juniper Ln, Woodstock, NY 12498
• 

  

  /49

  Est $588,511

  Not Listed For Sale

  70 Vandebogart Rd, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 1963

  70 Vandebogart Rd, Woodstock, NY 12498

  Last Sold Summary

  • 61 Days On Market
• 

  

  /33

  $699,000

  $51K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,718 Sq Ft

  170 MacDaniel Rd, Bearsville, NY 12409

  Driving on this scenic road just minutes from Woodstock, you'll discover a private, paved driveway leading to a sunlit clearing and attractive raised ranch surrounded by lawns and breathtaking mountain views. After taking in the scenery, step up to the home's welcoming main level, where natural light pours in from all sides. The open living space includes sliders to a large deck perfect for

  Judy Steinfeld Halter Associates Realty

  170 MacDaniel Rd, Bearsville, NY 12409
• 

  

  /30

  $480,000

  Sold Mar 23, 2026

  34 Forestwood Dr, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,489 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Below List Price
  • $193/SF
  • 86 Days On Market

  Current Estimated Value $495,858

  Last Listing Agent Brenda Graf Corcoran Country Living

  34 Forestwood Dr, Woodstock, NY 12498
• 

  

  /37

  Est $624,448

  Not Listed For Sale

  22 Oriole Dr, Woodstock, NY 12498

  • 4 Beds
  • 2.5 Baths
  • 2,609 Sq Ft
  • Built 1964

  22 Oriole Dr, Woodstock, NY 12498

  Last Sold Summary

  • 65 Days On Market
• 

  

  /33

  $595,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,321 Sq Ft

  419 Sickler Rd, Willow, NY 12495

  Relax, unwind, and take in the views from this charming cottage on one of the most bucolic and peaceful roads in the Woodstock hamlet of Willow--where every day feels like a weekend escape. The tranquility, mountain views, and picturesque valley setting have been cherished by one family for 47 years. Tucked away from the road and nearly invisible to passersby, the property welcomes you with the

  Marcia Weiss Halter Associates Realty

  419 Sickler Rd, Willow, NY 12495
• 

  

  /67

  $667,000

  Sold Sep 05, 2025

  33 Cottonwood Ln, Woodstock, NY 12498

  • 3 Beds
  • 2 Baths
  • 1,973 Sq Ft
  • Built 1965

  Last Sold Summary

  • 33% Below List Price
  • $338/SF
  • 259 Days On Market

  Current Estimated Value $710,335

  Last Listing Agent Amy Lonas Coldwell Banker Village Green

  33 Cottonwood Ln, Woodstock, NY 12498
• 

  

  /33

  Est $653,147

  Not Listed For Sale

  4 Oriole Dr, Woodstock, NY 12498

  • 4 Beds
  • 2 Baths
  • 2,430 Sq Ft
  • Built 1960

  4 Oriole Dr, Woodstock, NY 12498

  Last Sold Summary

  • 19 Days On Market
• 

  

  /50

  $1,599,999

  $99K PRICE DROP

  • 8 Beds
  • 5.5 Baths
  • 4,648 Sq Ft

  2320 Glasco Turnpike, Woodstock, NY 12498

  Welcome to The Waterfall House, a truly rare offering nestled in the heart of Woodstock Proper, where nature, creativity, and privacy converge in the most enchanting way. Being offered for the first time, this storied 3,023 sq ft brick colonial is more than a home; it’s an experience, a retreat, and an open canvas for your vision to unfold. Set on nearly 12 acres of lush, mature landscape, the

  Leigh Wagner-Quintana KW Hudson Valley North

  2320 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /67

  $1,410,000

  Sold Oct 22, 2025

  279 Cooper Lake Rd, Woodstock, NY 12498

  • 4 Beds
  • 4 Baths
  • 3,193 Sq Ft
  • Built 1968

  Last Sold Summary

  • 9% Below List Price
  • $442/SF
  • 118 Days On Market

  Last Listing Agent Ellen Osgood Coldwell Banker Village Green

  279 Cooper Lake Rd, Woodstock, NY 12498

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