6,128

Woodstock, NY Homes

Section Image Section Image
  • /52

    $1,180,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,772 Sq Ft

    34 Upper West Ohayo Mountain Rd, Bearsville, NY 12409

    Set on more than nine private acres just minutes from the heart of Woodstock, this elegant sprawling ranch is a rare offering where the views take center stage. Thoughtfully designed in the spirit of 1960s contemporary architecture, the home was created to celebrate its extraordinary natural setting, with sweeping vistas enjoyed from nearly every room. A substantial spring-fed pond, serene pine

    Agent Photo

    Amy Lonas

    Coldwell Banker Village Green

    34 Upper West Ohayo Mountain Rd, Bearsville, NY 12409
  • /20

    $10,923

    Total Monthly Price

    • 4 Beds
    • 4 Baths
    • 2,798 Sq Ft
    • Condo for Rent

    28 Holiday Dr Unit SI ID1546434P, Woodstock, NY 12498

    The advertised rate of $10,923/month is the lowest available price, based on a 1 month(s) and 2 day(s) stay with a move-in date of February 17, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed

    28 Holiday Dr Unit SI ID1546434P, Woodstock, NY 12498
  • /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 $344,755

    Last Listing Agent James Murphy Patty Conti Realty Group LLC

    23 Cottonwood Ln, Woodstock, NY 12498
    • /29

      Not Listed For Sale

      3555 Route 212, Woodstock, NY 12498

      • 2 Beds
      • 1 Bath
      • 1,162 Sq Ft
      • Built 1915
      3555 Route 212, Woodstock, NY 12498

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Julie Senecal Grist Mill Real Estate

  • /52

    $649,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 2,856 Sq Ft

    3 Coyote Ct, Woodstock, NY 12498

    Private and peaceful, 3 Coyote Lane is set on 2 manicured acres along a quiet country road where Kingston, Saugerties and Woodstock meet. With 2,856 square feet of comfortable living space, this 3-bedroom, 3.5-bath home features a practical, well-designed layout with generous room sizes and flexible living areas.The primary suite is a defining feature of the home, offering an unusually

    Agent Photo

    Amy Lonas

    Coldwell Banker Village Green

    3 Coyote Ct, Woodstock, NY 12498
  • /20

    $9,800 Per Month

    • 4 Beds
    • 3 Baths
    • 2,714 Sq Ft
    • House for Rent

    64 Meher Cir, Woodstock, NY 12498

    Woodstock | Private Summer Residence with Pool | 4BR/3BA | May 22-Oct 31 Set on over two private acres in one of Woodstock's most desirable locations, this fully furnished 4-bedroom, 3-bath residence is available for an extended summer stay (31-day minimum). Recently renovated. Clean lines and strong natural light. Layout offers both flow and separation, with multiple areas for living, dining,

    Sheena Lepez Compass Greater New York, LLC

    64 Meher Cir, Woodstock, NY 12498
  • /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

    Current Estimated Value $840,183

    Last Listing Agent Leslie Foti Coldwell Banker Village Green

    16 Marko Grove, Woodstock, NY 12498
    • /40

      Not Listed For Sale

      3906 New York 212, Lake Hill, NY 12448

      • 3 Beds
      • 2 Baths
      • 1,748 Sq Ft
      • Built 1983
      3906 New York 212, Lake Hill, NY 12448

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Amy Lonas Coldwell Banker Village Green

  • /59

    $1,375,000

    • 3 Beds
    • 2 Baths
    • 1,993 Sq Ft

    60 Boggs Hill Rd, Woodstock, NY 12498

    A Rare Byrdcliffe-Era Magical Retreat with Artistic Legacy Built in 1905, just as the historic Byrdcliffe Arts Colony and the Art Students League of New York's renowned summer school were taking root, this extraordinary three-bedroom, two-bath, one-of-a-kind residence is a rare architectural treasure deeply woven into Woodstock's creative history. Rich in authenticity and soul, the home

    Agent Photo

    Amy Lonas

    Coldwell Banker Village Green

    60 Boggs Hill Rd, Woodstock, NY 12498
  • /8

    $2,300 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    5-7 Rock City Rd Unit 3D, Woodstock, NY 12498

    5-7 Rock City Rd Unit 3D, Woodstock, NY 12498
  • /50

    $976,000

    Sold Jan 29, 2026

    13 16 Torn Hill Rd, Bearsville, NY 12409

    • 4 Beds
    • 2.5 Baths
    • 2,780 Sq Ft
    • Built 1935

    Last Sold Summary

    • 12% Below List Price
    • $351/SF
    • 60 Days On Market

    Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

    13 16 Torn Hill Rd, Bearsville, NY 12409
    • /35

      Est $1,273,522

      Not Listed For Sale

      2680 Glasco Turnpike, Wood Stock, NY 12498

      • 4 Beds
      • 2.5 Baths
      • 2,075 Sq Ft
      • Built 1898
      2680 Glasco Turnpike, Wood Stock, NY 12498

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Kelcey Otten Compass Greater NY, LLC

  • /40

    $550,000

    $99K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    5 Streamside Terrace, Woodstock, NY 12498

    Major price reduction. Seller says sell!!Woodstock Village living doesn't get much better than this. Perfectly positioned on a quiet no outlet street just moments from the heart of town, this beautifully renovated three-bedroom, two-bath home offers the rare opportunity to enjoy both nature and village life without compromise. Step inside to bright, sun-filled interiors and an open, welcoming

    Agent Photo

    Amy Lonas

    Coldwell Banker Village Green

    5 Streamside Terrace, Woodstock, NY 12498
  • /11

    $3,195 Per Month

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • House for Rent

    18 Rock City Rd Unit C, Wood Stock, NY 12498

    Welcome to your dream home in the enchanting town of Woodstock, just a two-hour bus ride from the heart of NYC or a 15-minute drive from the Thruway Exit 19 (Kingston). Imagine waking up every morning in a beautifully preserved historic carriage house in the heart of the lively town center. Walk to numerous restaurants, bars, shops, markets, bakeries, pharmacies, galleries, the cinema and the

    James Angelakis BHHS HUDSON VALLEY PROP-WDST

    18 Rock City Rd Unit C, Wood Stock, NY 12498
  • /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

    Current Estimated Value $926,485

    Last Listing Agent Judy Steinfeld Halter Associates Realty

    8 Pine Grove St, Woodstock, NY 12498
    • /2

      Est $704,480

      Not Listed For Sale

      12 Tannery Brook Rd, Wood Stock, NY 12498

      • Studio
      • 2 Baths
      • 1,269 Sq Ft
      • Built 1975
      12 Tannery Brook Rd, Wood Stock, NY 12498

  • /46

    $1,125,000

    $75K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 2,363 Sq Ft

    4599 New York 212, Willow, NY 12495

    Creekside Modern Home with Mountain Views Near Woodstock Surrounded by mountains with private access to a year-round creek, this thoughtfully designed home feels deeply connected to its setting while offering comfort, privacy, and modern convenience. Built in 2017 and significantly expanded and upgraded in 2022, the property blends clean contemporary design with warmth and functionality. Large

    Agent Photo

    Leigh Bokser

    Compass Greater NY, LLC

    4599 New York 212, Willow, NY 12495
  • /6

    $2,250 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    5-7 Rock City Rd Unit 3A, Woodstock, NY 12498

    5-7 Rock City Rd Unit 3A, Woodstock, NY 12498
  • /41

    $530,000

    Sold Dec 19, 2025

    5 Violet Place, Woodstock, NY 12498

    • 3 Beds
    • 1.5 Baths
    • 1,804 Sq Ft
    • Built 1963

    Last Sold Summary

    • 2% Below List Price
    • $294/SF
    • 33 Days On Market

    Current Estimated Value $549,376

    Last Listing Agent Fawn Denue Keller Williams Realty HV Nort

    5 Violet Place, Woodstock, NY 12498
    • /30

      Est $781,031

      Not Listed For Sale

      86 Baumgarten Rd, Woodstock, NY 12498

      • 2 Beds
      • 2 Baths
      • 2,280 Sq Ft
      • Built 2016
      86 Baumgarten Rd, Woodstock, NY 12498

      Last Sold Summary

      • 105 Days On Market

      Last Listing Agent Baris Demirel Serhant LLC

  • /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

    Agent Photo

    Leigh Bokser

    Compass Greater NY, LLC

    465 Sickler Rd, Willow, NY 12495
  • /36

    $19,500 Per Month

    • 4 Beds
    • 2 Baths
    • 1,499 Sq Ft
    • House for Rent

    55 Nordic Dr, Woodstock, NY 12498

    *SUMMER & FALL RENTAL* (AVAIL May 25 - Oct 31, 2026) // This unique hilltop property includes two separate structures -- a beautifully designed three-bedroom main house and a private loft guest house offering flexible space so you have accommodations for up to 10+ guests. Tucked away on a private hilltop ridge just under three miles from the pulse of Woodstock, 55 Nordic Drive is a secluded

    Alexis Li Corcoran Country Living

    55 Nordic Dr, Woodstock, NY 12498
  • 18 Striebel Rd, Woodstock, NY 12498

    $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 $4,268,568

    Last Listing Agent Kathryn Johnson William Pitt Sothebys Int Rlty

    18 Striebel Rd, Woodstock, NY 12498
    • /30

      Not Listed For Sale

      18 Rock City Rd, Wood Stock, NY 12498

      • 3 Beds
      • 3 Baths
      • 2,683 Sq Ft
      • Built 1890
      18 Rock City Rd, Wood Stock, NY 12498

      Last Sold Summary

      • 132 Days On Market

      Last Listing Agent Judy Steinfeld Halter Associates Realty

  • /50

    $1,950,000

    $400K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,322 Sq Ft

    24 Tanis Hollow Rd, Woodstock, NY 12498

    Million-Dollar Views as Far as the Eye Can SeePerched privately on 5.1 acres with breathtaking 100-mile panoramic views, this extraordinary log home is a true architectural masterpiece. Constructed from massive 18 to 20 inch in diameter logs that required cranes for assembly and individually placed upon an expertly engineered foundation, this remarkable residence represents a level of

    Agent Photo

    Randy Spiesman

    Weichert REALTORS

    24 Tanis Hollow Rd, Woodstock, NY 12498
  • /25

    $15,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,393 Sq Ft
    • House for Rent

    20 Handys Walk, Shady, NY 12409

    Here's your chance to spend a flexible season staring at one of the most incredible views this seasoned agent has ever seen in the Catskills. Featured in the book Woodstock Handmade Houses, this beautiful and private home on Overlook Mountain is the perfect marriage of Swedish minimalism and antique rustic materials. The panoramic views reveal themselves immediately upon entering the home. The

    Briana Cermak Compass Greater NY, LLC

    20 Handys Walk, Shady, NY 12409
  • /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

    Current Estimated Value $373,575

    Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

    57 Overlook Dr, Woodstock, NY 12498
    • /24

      Est $719,018

      Not Listed For Sale

      7 Lark Dr, Wood Stock, NY 12498

      • 3 Beds
      • 2.5 Baths
      • 1,345 Sq Ft
      • Built 2024
      7 Lark Dr, Wood Stock, NY 12498

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Richard Vizzini Corcoran Country Living

  • /40

    $749,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,969 Sq Ft

    364 John Joy Rd, Woodstock, NY 12498

    Set off a quiet lane and approached by a gracious circular driveway, this classic Cape Cod carries the particular confidence of a house that has always known exactly what it is. Spanning 1,969 square feet, the home has been thoughtfully refreshed throughout with all-new wood flooring, freshly painted interiors, updated bathrooms, and an eat-in kitchen with marble countertops and custom wood

    Laurie Ylvisaker Coldwell Banker Village Green

    364 John Joy Rd, Woodstock, NY 12498
  • /34

    $3,500 Per Month

    • 1 Bed
    • 1 Bath
    • 890 Sq Ft
    • House for Rent

    10 Fitzsimmons Ln, Woodstock, NY 12498

    Escape to your own private retreat nestled among mature trees and bordered by a tranquil stream. This unique property offers an extraordinary blend of nature, privacy, and relaxation, creating a setting that feels worlds away from everyday life. Designed with a Zen-inspired aesthetic, the home features a remarkable spa-like bath suite complete with a slate walk-in shower, bamboo accents, river

    Greg Berardi Berardi Realty

    10 Fitzsimmons Ln, Woodstock, NY 12498
  • /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
    • /33

      Est $2,230,887

      Not Listed For Sale

      70 Raybrook Dr, Woodstock, NY 12498

      • 4 Beds
      • 3.5 Baths
      • 3,100 Sq Ft
      • Built 2013
      70 Raybrook Dr, Woodstock, NY 12498

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

  • /37

    $815,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 2,471 Sq Ft

    376 Abbey Rd, Mount Tremper, NY 12457

    This classic contemporary retreat owned by the same family for over 2 decades is privately nestled on five picturesque acres along one of Woodstock's most coveted roads. Tucked away on a town-maintained dead-end lane, the property offers exceptional privacy and a true escape, all while remaining just minutes from the heart of Woodstock.Filled with natural light, this two-bedroom, two-bathroom

    Victoria Stent Coldwell Banker Village Green

    376 Abbey Rd, Mount Tremper, NY 12457
  • /36

    $16,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,394 Sq Ft
    • House for Rent

    75 Hill 99, Woodstock, NY 12498

    AVAIL FROM OCT 2026. Secluded Mountain Chalet with Breathtaking Views and Poolside Lodge - Set atop nine private acres, this stunning mountaintop chalet offers a rare combination of serenity, seclusion, and spectacular views. A long, private driveway winds through the property, leading to a retreat unlike any other. The property features a three-story main house and a separate two-story Poolside

    Alexis Li Corcoran Country Living

    75 Hill 99, Woodstock, NY 12498
  • 551 Mount Guardian Rd, Shady, NY 12409

    $1,577,000

    Sold Jun 11, 2026

    551 Mount Guardian Rd, Shady, NY 12409

    • 2 Beds
    • 2 Baths
    • 2,308 Sq Ft
    • Built 1983

    Last Sold Summary

    • 1% Above List Price
    • $683/SF
    • 13 Days On Market

    Last Listing Agent Sharon Breslau BHHS Hudson Valley Properties

    551 Mount Guardian Rd, Shady, NY 12409
    • 18 Maple Ln, Wood Stock, NY 12498

      Est $1,116,574

      Not Listed For Sale

      18 Maple Ln, Wood Stock, NY 12498

      • 6 Beds
      • 6 Baths
      • 4,400 Sq Ft
      • Built 1910
      18 Maple Ln, Wood Stock, NY 12498

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Heidi Maloney Four Seasons Sothebys Intl

  • /40

    $825,000

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

    97 John Joy Rd, Woodstock, NY 12498

    Set beside one of Woodstock's most treasured and enduring landscapes, this quintessential Woodstock property unfolds along the edge of the Thorn Preserve--a protected 60-acre expanse celebrated for its sweeping open grasslands, riparian forest, ponds, and the most artist-captured views of Overlook Mountain. Even more remarkable, this landscape is permanently conserved, ensuring that the

    Richard Vizzini Corcoran Country Living

    97 John Joy Rd, Woodstock, NY 12498
  • /49

    $5,500 Per Month

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

    299 Wittenberg Rd, Bearsville, NY 12409

    Luxury 3-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 3-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
  • /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

    Current Estimated Value $401,732

    Last Listing Agent Laura Prince Hudson Dwellings Realty

    38 Arnold Dr, Woodstock, NY 12498
    • /32

      Est $931,106

      Not Listed For Sale

      185 John Joy Rd, Wood Stock, NY 12498

      • 3 Beds
      • 3 Baths
      • 2,258 Sq Ft
      • Built 2015
      185 John Joy Rd, Wood Stock, NY 12498

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Sheena Lepez Compass Greater New York, LLC

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$700,000
Median Single Family Sale Price
$741,000
Median Townhouse Sale Price
$772,500
Median 2 Bedroom Sale Price
$665,350
Median 1 Bedroom Sale Price
$462,500
Average Price Per Sq Ft
$456
Number of Homes for Sale
35
Last 12 months Home Sales
115
Months of Supply
3.70
Median List Price
$785,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
10%
How to Buy a Home How to Finance a Home How to Sell a Home