Woodstock, NY Homes

/42
$1,199,000
- 4 Beds
- 2 Baths
- 3,378 Sq Ft
3207-3209 New York 212, Bearsville, NY 12409

Enchanting Woodstock Compound with a Craftsman Home, Cottage, and Historic Barn. Welcome to a truly rare offering in the heart of the Catskills, just minutes from the center of Woodstock, yet tucked away in a storybook setting of trees, meadows, and the soothing sounds of the Sawkill stream. This private 1.85-acre homestead compound blends rustic charm with modern versatility, featuring a

Michelle Bergkamp William Pitt Sotheby's Interna

3207-3209 New York 212, Bearsville, NY 12409
/15
$3,600 Per Month
- 2 Beds
- 1 Bath
- 1,200 Sq Ft
- House for Rent
36 Northwoods Rd Unit A, Woodstock, NY 12498

A stunning, fully furnished guest house in a private setting in Woodstock! There's nothing more to ask for in this single level guest home with two bedrooms, a single bathroom and stunning open kitchen and living area. This home is naturally well-lit including skylights and picturesque nature views from each window. If this wasn't enough inside, step outside to your private outdoor area with

Amy Hawks Berardi Realty

36 Northwoods Rd Unit A, 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 $598,934

Last Listing Agent Laurel Sweeney BHHS Nutshell Realty

18 Niles Dr, Woodstock, NY 12498

/34
Est $802,496 Not Listed For Sale

5249 Route 212, Mount Tremper, NY 12457
- 4 Beds
- 3 Baths
- 2,201 Sq Ft
- Built 1990
5249 Route 212, Mount Tremper, NY 12457

Last Sold Summary
- 20% Above List Price
- $304/SF
- 63 Days On Market
- Last Sold Price $669,000
- Jun 25, 2024
Last Listing Agent Hillary Kolos Compass Greater NY, LLC

/41
$895,000
- 3 Beds
- 2.5 Baths
- 2,264 Sq Ft
168 Cooper Lake Rd, Bearsville, NY 12409

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 built in 1940 and renovated over the years, this

Melissa Mayes Serhant LLC

168 Cooper Lake Rd, Bearsville, NY 12409
/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 $599,617

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

148 Hutchin Hill Rd, Shady, NY 12409

/32
Est $2,557,877 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
- 2% Below List Price
- $658/SF
- 81 Days On Market
- Last Sold Price $2,600,000
- Feb 03, 2024
Last Listing Agent Jeff Serouya Compass Greater NY, LLC

/33
$799,000
- 4 Beds
- 2.5 Baths
- 2,340 Sq Ft
12 Oriole Dr, Woodstock, NY 12498

A bright and sunny Colonial gem just minutes into the center of Woodstock! This home is set far back and hidden from the road creating a true sense of privacy. Coming down the driveway, you begin to see the 1.47 acre yard wrapping around the house which is partially bordered by a charming stone wall. Once inside, the spacious living room is on your left with built-in bookcases and a fireplace

Richard Stoll Halter Associates Realty

12 Oriole Dr, 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 $553,345

Last Listing Agent Amy Lonas Coldwell Banker Village Green

2059 Glasco Turnpike, Woodstock, NY 12498

/31
Est $999,796 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
- 2% Above List Price
- $250/SF
- 12 Days On Market
- Last Sold Price $978,000
- Apr 21, 2025
Last Listing Agent Alexis Li Corcoran Country Living

/15
$595,000
- 3 Beds
- 1.5 Baths
- 1,133 Sq Ft
501 Ohayo Mountain Rd, Woodstock, NY 12498

Discover your Upstate sanctuary in this contemporary 3-bedroom, 1.5-bath gem on Ohayo Mountain Road. Nestled in wooded bliss on 1.8 acres and in close proximity to protected state land, this home delivers a rare sense of peace and enduring natural beauty. Gleaming hardwood floors, a cozy wood-burning stove, and an open-concept floorplan perfect for modern living. Step outside to your private

James Angelakis BHHS HUDSON VALLEY PROP-WDST

501 Ohayo Mountain Rd, Woodstock, NY 12498
/33
$925,000 Sold Jun 16, 2025

9 Shady Ln, Bearsville, NY 12409
- 3 Beds
- 2 Baths
- 2,138 Sq Ft
- Built 1976
Last Sold Summary
- 3% Above List Price
- $433/SF
- 21 Days On Market
Current Estimated Value $940,657

Last Listing Agent Casey Kearns Past Member

9 Shady Ln, Bearsville, NY 12409

/22
Est $627,411 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
- 16% Above List Price
- $256/SF
- 13 Days On Market
- Last Sold Price $540,000
- Dec 18, 2023
Last Listing Agent Peter Cantine Halter Associates Realty

/11
$499,000
- Land
- 15.23 Acres
- $32,764 per Acre
Tbd Wardwell Ln, Woodstock, NY 12498

A rarely available large, 15+ acre parcel in Woodstock -- less than a mile from the center of town! Completely private yet moments away from restaurants, music venues, shops, golf course and hiking. A mixture of mature deciduous and conifer trees offer a forest haven, with level land, rock features and an elevated knoll building site, ready for your next chapter.Much of the heavy lifting has

Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

Tbd Wardwell Ln, 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 $599,608 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
- 20% Above List Price
- $231/SF
- 33 Days On Market
- Last Sold Price $500,000
- Jun 07, 2024
Last Listing Agent Ronnie Rebis Grist Mill Real Estate

/34
$650,000 Pending
- 2 Beds
- 1 Bath
- 1,436 Sq Ft
117 Ohayo Mountain Rd, Woodstock, NY 12498

Set against a backdrop of sweeping mountain views and quiet Woodstock landscape, this inviting country property offers a rare blend of charm, space, and opportunity.The main home features 2 bedrooms and 1 bath, with a warm, welcoming interior defined by original hardwood floors, rich wood-paneled walls, and a classic wood-burning fireplace that anchors the living room. A bluestone enclosed

Donna Brooks Compass Greater New York, LLC

117 Ohayo Mountain 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 $633,351

Last Listing Agent Amy Lonas Coldwell Banker Village Green

916 Zena Rd, Woodstock, NY 12498

/29
Est $562,221 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
- 44% Above List Price
- $192/SF
- 97 Days On Market
- Last Sold Price $390,000
- Aug 14, 2023
Last Listing Agent Melissa Stella DeForest Coldwell Banker Village GreenK

/31
$335,000
- 3 Beds
- 1 Bath
- 1,272 Sq Ft
42 Dixon Ave, Woodstock, NY 12498

Situated on a large level lot and a quiet road near the heart of town. Some recent updates and fresh paint make this 4 brdm ranch home a terrific find in today's market. A covered porch in the front and rear allow for convenient outdoor entertainment. There is also plenty of off street parking and a detached shed for additional storage. Central location just minutes to Woodstock's vibrant music

Rodney Batista Howard Hanna Rand Realty

42 Dixon Ave, 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 $492,059

Last Listing Agent Peter Cantine Halter Associates Realty

3523 Route 212, Bearsville, NY 12409

/35
Est $653,817 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
- 25% Above List Price
- $232/SF
- 16 Days On Market
- Last Sold Price $525,000
- Jun 27, 2023
Last Listing Agent Christine Nielson Past Member

/42
$599,000 Pending
- 5 Beds
- 2.5 Baths
- 1,939 Sq Ft
83 Ratterman Rd, Woodstock, NY 12498

It's a WINNER! This is truly a wonderful house in an excellent location! Surrounded by trees with a quiet, rural feel, yet walking distance to the Village of Woodstock, it's everything a Woodstock buyer is looking for! From the moment you step up to this charmer, you'll be welcomed by a wide, impressive Bluestone walkway to the Bluestone front porch where you can envision many peaceful hours

Edwin Maldonado Howard Hanna Rand Realty

83 Ratterman Rd, Woodstock, NY 12498
/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 $782,057

Last Listing Agent Leslie Foti Coldwell Banker Village Green

4 Munchkin Ln, Kingston, NY 12401

/27
Est $617,214 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
- 49% Above List Price
- $206/SF
- 6 Days On Market
- Last Sold Price $415,000
- Aug 01, 2023
Last Listing Agent Richard Vizzini Corcoran Country Living

/14
$395,000
- 1 Bed
- 1 Bath
- 841 Sq Ft
57 Ohayo Mountain Rd, Woodstock, NY 12498

WOODSTOCK VILLAGE COTTAGE - LOCATION, CATSKILLS CHARM & VALUE! Their loss is your gain --previous buyer couldn't qualify--so 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

Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

57 Ohayo Mountain Rd, Woodstock, NY 12498
/54
$445,000 Sold May 14, 2025

203 Maverick Rd, Woodstock, NY 12498
- 2 Beds
- 1.5 Baths
- 960 Sq Ft
- Built 1977
Last Sold Summary
- 12% Above List Price
- $464/SF
- 68 Days On Market
Current Estimated Value $460,950

Last Listing Agent Eric Amaral Coldwell Banker Village Green

203 Maverick Rd, Woodstock, NY 12498

/20
Est $741,757 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
- 2% Below List Price
- $349/SF
- 5 Days On Market
- Last Sold Price $758,554
- Aug 01, 2023
Last Listing Agent Luis Cabrera Amodio Real Estate & Prop

/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
/32
$1,450,000 Sold May 28, 2025

54 Shultis Farm Rd, Bearsville, NY 12409
- 5 Beds
- 4 Baths
- 3,722 Sq Ft
- Built 1952
Last Sold Summary
- 4% Above List Price
- $390/SF
- 35 Days On Market
Current Estimated Value $1,497,350

Last Listing Agent Christina Sellers William Pitt Sothebys Intn'l

54 Shultis Farm Rd, Bearsville, NY 12409

/47
Est $907,625 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
- $340/SF
- 42 Days On Market
- Last Sold Price $910,000
- Sep 13, 2024
Last Listing Agent Luis Cabrera Amodio Real Estate & Prop

/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
/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 $1,645,703

Last Listing Agent Victoria Stent Coldwell Banker Village Green

16 Juniper Ln, Woodstock, NY 12498

/49
Est $612,379 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
- 5% Above List Price
- $298/SF
- 61 Days On Market
- Last Sold Price $585,000
- Feb 19, 2025
Last Listing Agent Dominique Musialkiewicz Howard Hanna Rand Realty

/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
/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 $510,636

Last Listing Agent Brenda Graf Corcoran Country Living

34 Forestwood Dr, Woodstock, NY 12498

/37
Est $630,071 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
- 10% Above List Price
- $220/SF
- 65 Days On Market
- Last Sold Price $575,000
- Oct 18, 2024
Last Listing Agent Patty Kowatch Keller Williams Realty HV Nort

/50
$1,699,000
- 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 Keller Williams Hudson Valley

2320 Glasco Turnpike, Woodstock, NY 12498
/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 $689,855

Last Listing Agent Amy Lonas Coldwell Banker Village Green

33 Cottonwood Ln, Woodstock, NY 12498

/33
Est $682,001 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
- $279/SF
- 19 Days On Market
- Last Sold Price $679,000
- May 10, 2024
Last Listing Agent Elizabeth Suib-Parisio Past Member

Showing Results 81 - 120, Page 3 of 18

New York Ulster County Woodstock

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Woodstock, NY Homes

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