Woodstock, NY Homes

/39
$1,495,000 Pending
- 3 Beds
- 3 Baths
- 2,064 Sq Ft
529 Mount Guardian Rd, Woodstock, NY 12409

Welcome to the Mount Guardian Modern. Positioned on nearly four acres on Mount Guardian, this Woodstock contemporary is the rare new construction that gets everything right: the siting, the light, the materials, the silence. Completed in 2021, it offers three bedrooms, three bathrooms, and 2,064 square feet of architecture that feels both intentional and effortless, anchored by a first-floor

Laurie Ylvisaker Coldwell Banker Village Green

529 Mount Guardian Rd, Woodstock, NY 12409
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/24
$4,800 Per Month
- 2 Beds
- 2 Baths
- 2,471 Sq Ft
- House for Rent
376 Abbey Rd, Mount Tremper, NY 12457

Located on one of Woodstock's most desirable roads sits this classic contemporary set on 5 acres. Privately situated on a town-maintained, dead end lane for that ultimate get-away feeling, this light-filled, two bedroom, two bathroom home with additional flex space, features soaring ceilings with solid wood floors, flooded with natural light from floor-to-ceiling windows. The main living area

Victoria Stent Coldwell Banker Village Green

376 Abbey Rd, Mount Tremper, NY 12457
/27
$942,200 Sold Apr 16, 2026

58 Jones Quarry Rd, Woodstock, NY 12498
- 3 Beds
- 2.5 Baths
- 2,552 Sq Ft
- Built 1985
Last Sold Summary
- 1% Below List Price
- $369/SF
- 36 Days On Market
Current Estimated Value $936,890

Last Listing Agent Michelle Bergkamp William Pitt Sotheby's Interna

58 Jones Quarry Rd, Woodstock, NY 12498

/33
Est $2,076,561 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
- 9% Below List Price
- $735/SF
- 68 Days On Market
- Last Sold Price $2,280,000
- Jan 30, 2025
Last Listing Agent Melissa Zoe Hirsch Coldwell Banker Village Green

/42
$1,557,000 Pending
- 3 Beds
- 2 Baths
- 2,308 Sq Ft
551 Mount Guardian Rd, Shady, NY 12409

Wend up a pristine country road to this 2,300 sq ft Woodstock contemporary—arriving to total seclusion and picturesque views, yet only minutes to the Village Green. This domain is set on 4+ private acres with an additional almost 4 acre, separately-deeded, contiguous parcel that makes it an ideal property for a compound, or to use with it's maximum natural buffer for ultimate privacy. Close

Sharon Breslau BHHS Hudson Valley Properties

551 Mount Guardian Rd, Shady, NY 12409
/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 SEPT 2025. 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
/25
$770,000 Sold Mar 11, 2026

86 Rock City Rd, Woodstock, NY 12498
- 4 Beds
- 2.5 Baths
- 1,754 Sq Ft
- Built 1910
Last Sold Summary
- 7% Below List Price
- $439/SF
- 90 Days On Market
Current Estimated Value $761,123

Last Listing Agent Michael Shaughnessy Halter Associates Realty

86 Rock City Rd, Woodstock, NY 12498

/32
Est $948,428 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
- $421/SF
- 37 Days On Market
- Last Sold Price $950,000
- Nov 12, 2024
Last Listing Agent Sheena Lepez Compass Greater New York, LLC

/30
$749,990
- 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 long private 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
/31
$12,000 Per Month
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
- House for Rent
206 Hutchin Hill Rd, Bearsville, NY 12409

Escape the City and Find Your Peace Experience the height of summer in the Hudson Valley at this contemporary mountain home located on one of Woodstock's most coveted roads. This private sanctuary offers the perfect blend of secluded nature and modern luxury, just minutes from the Bearsville Theater and the heart of Woodstock village. Contemporary Design: An architectural gem featuring an

Melissa Zoe Hirsch Coldwell Banker Village Green

206 Hutchin Hill Rd, Bearsville, NY 12409
$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

Not Listed For Sale

0 Wittenberg Rd Unit KEYH6302035, Woodstock, NY 12498
0 Wittenberg Rd Unit KEYH6302035, Woodstock, NY 12498

Last Sold Summary
- 64 Days On Market
- Last Sold Price $550,000
- Oct 30, 2024
Last Listing Agent Sean Zimmerman Halter Associates Realty Inc

/72
$1,395,000
- 3 Beds
- 3 Baths
- 2,566 Sq Ft
1 Wittenberg Rd, Bearsville, NY 12409

Welcome to Bearsville Record House, a landmark property with a legacy in American music. Built in 1873 and once home to Bearsville Records, this storied compound includes two dwellings; the main farmhouse and a guest cottage, plus a studio building waiting to be finished to your specs. A gunite saltwater pool, outdoor kitchen, and fenced-in plum orchard complete the grounds, all along 500 feet of

Anthony D'Argenzio Houlihan Lawrence

1 Wittenberg Rd, Bearsville, NY 12409
/17
$1,600 Per Month
- 1 Bed
- 1 Bath
- 400 Sq Ft
- Apartment for Rent
43-47 Tinker St Unit 1, Woodstock, NY 12498

Perfectly situated in the vibrant heart of Woodstock, this 400-square-foot apartment at 43-47 Tinker Street offers an unbeatable ''walk-to-everything'' lifestyle. The versatile layout features two distinct rooms in addition to the bathroom, providing a clear separation between your living area and sleeping quarters or a home office. At the center of the home is a functional galley kitchen,

Robert Leone Serhant LLC

43-47 Tinker St Unit 1, Woodstock, NY 12498
/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
Current Estimated Value $627,601

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

3 Oriole Dr, Woodstock, NY 12498

Not Listed For Sale

1183-1185 Wittenberg Rd, Mount Tremper, NY 12457
- 10 Beds
- 3 Baths
- 3,954 Sq Ft
- Built 1924
1183-1185 Wittenberg Rd, Mount Tremper, NY 12457

Last Sold Summary
- $130/SF
- 151 Days On Market
- Last Sold Price $515,000
- Apr 29, 2025
Last Listing Agent Roadman Etienne BHHS Hudson Valley Properties

/30
$849,000
- 4 Beds
- 2.5 Baths
- 2,584 Sq Ft
1 Stone Ridge Ct, Woodstock, NY 12498

Tucked into a quiet cul-de-sac, this spacious 4-bedroom, 2.5-bath Colonial features a gorgeous in-ground swimming pool surrounded by mature plantings. With a comfortable, easy flow, a welcoming foyer opens to a bright main level that connects the living room, dining area, and updated kitchen.The kitchen is equipped with granite countertops and stainless-steel appliances, while the bathrooms

Susanna Scott-Mitchell Compass Greater NY, LLC

1 Stone Ridge Ct, Woodstock, NY 12498
/52
$9,000 Per Month
- 3 Beds
- 2 Baths
- 1,920 Sq Ft
- House for Rent
3870 New York 212, Bearsville, NY 12409

Woodstock Summer 2026! Perched on a hill with panoramic views of the Cooper Lake this residence seamlessly blends European sophistication with Woodstock country vibes. Designed with an emphasis on light and line, the home features an open-concept layout framed by floor-to-ceiling glass, ensuring the mountain and lake vistas remain the focal point of every room. The interior aesthetic is a refined

Melissa Zoe Hirsch Coldwell Banker Village Green

3870 New York 212, Bearsville, NY 12409
/43
$2,700,000 Sold Jun 13, 2025

2655 Glasco Turnpike, Woodstock, NY 12498
- 4 Beds
- 3 Baths
- 3,390 Sq Ft
- Built 1945
Last Sold Summary
- 16% Below List Price
- $796/SF
- 209 Days On Market
Current Estimated Value $2,734,184

Last Listing Agent Richard Vizzini Corcoran Country Living

2655 Glasco Turnpike, Woodstock, NY 12498

Not Listed For Sale

363 Cold Brook Rd, Bearsville, NY 12409
- 3 Beds
- 2 Baths
- 3,126 Sq Ft
- Built 1985
363 Cold Brook Rd, Bearsville, NY 12409

Last Sold Summary
- $272/SF
- 117 Days On Market
- Last Sold Price $850,000
- May 08, 2025
Last Listing Agent Carol Spirig Halter Associates Realty Inc

/52
$1,275,000
- 4 Beds
- 5 Baths
- 3,080 Sq Ft
27 Old Wagon Rd, Woodstock, NY 12498

Just a half mile from the center of Woodstock, this bucolic 3.7-acre compound offers a rare blend of architectural charm, natural beauty, and versatile living. The property includes the main house and two outbuildings, a one-bedroom cottage and a studio with an attached three-bay garage. Bedroom and bath layout described as the primary residence having three bedrooms and three full baths

Megan Rios Berardi Realty

27 Old Wagon 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
/28
$257,000 Sold Feb 27, 2026

259 Silver Hollow Rd, Willow, NY 12495
- 1 Bath
- 475 Sq Ft
- Built 1950
Last Sold Summary
- 1% Below List Price
- $541/SF
- 58 Days On Market
Current Estimated Value $250,402

Last Listing Agent Leslie Foti Coldwell Banker Village Green

259 Silver Hollow Rd, Willow, NY 12495

/24
Not Listed For Sale

18 Vandermark Rd, Woodstock, NY 12498
- 2 Beds
- 2 Baths
- 950 Sq Ft
- Built 2024
18 Vandermark Rd, Woodstock, NY 12498

Last Sold Summary
- $578/SF
- 24 Days On Market
- Last Sold Price $549,000
- Dec 11, 2024
Last Listing Agent Zachary Jarvis BHHS Nutshell Realty

/24
$1,150,000
- 3 Beds
- 4 Baths
- 3,120 Sq Ft
540 Mount Tobias Rd, Mount Tremper, NY 12457

A modernist retreat set against one of the most striking backdrops in the Catskills. 540 Mt. Tobias Road is an architect-designed home where clean lines and expansive glass dissolve the boundary between indoors and out. A wall of windows frames uninterrupted mountain views, pulling light and landscape into every corner of the home. The effect is immediate. Calm, quiet, and completely immersive.

Alexander James Compass Greater NY, LLC

540 Mount Tobias Rd, Mount Tremper, NY 12457
/38
$5,900 Per Month
- 2 Beds
- 2 Baths
- 1,655 Sq Ft
- House for Rent
25 Boggs Hill Rd, Woodstock, NY 12498

Privately nestled in the woods, yet just a short distance from Woodstock Village, this just completed total restoration and modernization offers finest in quality finishes throughout. Open main level design ideal for your lifestyle features complete chef's kitchen with generous farmhouse sink, slide out pantry, top of the line appliances, and access to outside ideal for placement of a grill.

Nan Potter Potter Realty

25 Boggs Hill Rd, Woodstock, NY 12498
/40
$1,055,000 Sold Aug 20, 2025

10 Magnolia Trail, Woodstock, NY 12498
- 4 Beds
- 3 Baths
- 2,613 Sq Ft
- Built 2016
Last Sold Summary
- 4% Below List Price
- $404/SF
- 34 Days On Market
Last Listing Agent Joseph Satto Fresh Air Realty

10 Magnolia Trail, Woodstock, NY 12498

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Not Listed For Sale

162 Van Dale Rd Unit 170, Woodstock, NY 12498
- 3 Beds
- 2 Baths
- 2,299 Sq Ft
- Built 1925
162 Van Dale Rd Unit 170, Woodstock, NY 12498

Last Sold Summary
- $298/SF
- 80 Days On Market
- Last Sold Price $685,000
- Oct 13, 2023
Last Listing Agent Jeannine Simmons Corcoran Country Living

/30
$898,000
- 2 Beds
- 2 Baths
- 900 Sq Ft
14 Old Forge Rd, Woodstock, NY 12498

PROPERTY HIGHLIGHTS. Big ''Tiny House'': Designed for people who love Small Efficient Spaces, by the Water, with Mountain Views, enjoy living ''uncarred'', in the most Central Location in Woodstock. Layout: 2 bedrooms and 2 bathrooms. Exceptionally rare Climate Resilient Construction featuring Steel floor and ceiling joists with comprehensive Energy Efficient Upgrades throughout. INTERIOR

Danielle Sevier Compass Greater NY, LLC

14 Old Forge Rd, Woodstock, NY 12498
/14
$4,000 Per Month
- 4 Beds
- 2 Baths
- 2,158 Sq Ft
- House for Rent
295 Grog Kill Rd, Willow, NY 12495

SHORT TERM RENTAL: Private, fully furnished Woodstock Oasis with mountain views, is ready to be your country getaway! On a dead-end rd. up high on a hill, this Willow home has everything you need, close to hiking, skiing, restaurants and shopping, just minutes from Woodstock, Phoenicia and the NYS Thruway, this private retreat is available beginning March 2026

Mark Kanter BHHS HUDSON VALLEY PROP-WDST

295 Grog Kill Rd, Willow, NY 12495
/42
$967,500 Sold Dec 05, 2025

241 Silver Hollow Rd, Willow, NY 12495
- 3 Beds
- 2.5 Baths
- 1,932 Sq Ft
- Built 1963
Last Sold Summary
- 3% Below List Price
- $501/SF
- 47 Days On Market
Current Estimated Value $984,526

Last Listing Agent Carol Spirig Halter Associates Realty

241 Silver Hollow Rd, Willow, NY 12495

/28
Not Listed For Sale

16 Deming St, Woodstock, NY 12498
- 4 Beds
- 1 Bath
- 1,794 Sq Ft
- Built 1930
16 Deming St, Woodstock, NY 12498

Last Sold Summary
- $284/SF
- 111 Days On Market
- Last Sold Price $510,000
- Mar 15, 2024
Last Listing Agent Toby Ress Win Morrison Realty - W

/42
$895,000
- 3 Beds
- 3 Baths
- 2,316 Sq Ft
5 Maverick Terrace, Woodstock, NY 12498

Tucked away on a peaceful, wooded lane, this inviting home offers the perfect blend of privacy, space, and convenience- just minutes to the heart of Woodstock. Inside, the home opens to an expansive living room anchored by a beautiful brick fireplace, creating a warm and inviting centerpiece for gatherings or quiet evenings. This oversized space includes a full bathroom and flows effortlessly to

Dominique Musialkiewicz Howard Hanna Rand Realty

5 Maverick Terrace, Woodstock, NY 12498
/30
$9,500 Per Month
- 4 Beds
- 2.5 Baths
- 2,333 Sq Ft
- House for Rent
10 Purdy Hollow Rd, Woodstock, NY 12498

Summer Rental Opportunity: Rent by the month or the full season. Nestled in the serene hamlet of Zena, just five minutes from the heart of Woodstock, this exquisitely renovated cedar contemporary home offers a blend of elegance, comfort, and modern convenience. It is a sanctuary of refined living, set on three private acres directly across from the pristine 60-acre Thorn Preserve, which offers

Leslie Foti Coldwell Banker Village Green

10 Purdy Hollow Rd, Woodstock, NY 12498
/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 $883,526

Last Listing Agent Steven DiLorenzo Compass Greater NY LLC

52 Meher Cir, Woodstock, NY 12498

Not Listed For Sale

15 Silver Wings Ln, Woodstock, NY 12498
- 4 Beds
- 6.5 Baths
- 3,746 Sq Ft
- Built 1900
15 Silver Wings Ln, Woodstock, NY 12498

Last Sold Summary
- $360/SF
- 58 Days On Market
- Last Sold Price $1,350,000
- Sep 05, 2024
Last Listing Agent Hailey Kiesewetter Upstate Down

/61
$760,000
- 2 Beds
- 1.5 Baths
- 1,410 Sq Ft
15 Lake View Dr, Lake Hill, NY 12448

Own this stunning, architect-designed contemporary home in Woodstock, NY. Professionally decorated and thoughtfully crafted with passive solar principles, this energy-efficient residence seamlessly blends modern design with its natural surroundings. Set just across the road from the famous Cooper Lake, the home is nestled in a beautiful, 3 acre wooded setting—private yet not isolated—surrounded

Mackenzie Grate The Machree Group, LLC

15 Lake View Dr, Lake Hill, NY 12448
/15
$3,800 Per Month
- 2 Beds
- 1 Bath
- 956 Sq Ft
- House for Rent
35 Race Track Rd, Bearsville, NY 12409

Sweet bungalow in Bearsville available for rent and move in ready. Down private country lane situated next to lovely stream on almost 3 acres minutes to the center of Woodstock sits this remodeled 2 Bd/ 1 Ba home with polished concrete floors and perfectly furnished with a modern aesthetic. Sit on your covered deck looking out into the Catskill forest. Lounge in your cozy living room beside your

Johanna Trimboli Halter Associates Realty

35 Race Track Rd, Bearsville, NY 12409
$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 $1,066,149

Last Listing Agent Sharon Breslau BHHS Hudson Valley Properties

11 Grogkill Rd, Willow, NY 12495

/35
Not Listed For Sale

2292 Glasco Turnpike, Woodstock, NY 12498
- 3 Beds
- 3 Baths
- 2,870 Sq Ft
- Built 1924
2292 Glasco Turnpike, Woodstock, NY 12498

Last Sold Summary
- $352/SF
- 7 Days On Market
- Last Sold Price $1,010,000
- Apr 26, 2024
Last Listing Agent Daniel Romero Compass Greater New York, LLC

Showing Results 41 - 80, Page 2 of 18

New York Ulster County Woodstock

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Woodstock, NY Homes

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