Woodstock, NY Homes

$4,600,000 Sold Aug 25, 2025
- 3,899 Sq Ft
- $1,180/SF
- 99 Days On Market
- 4 Beds
- 4 Baths
- Built 1914
18 Striebel Rd, Woodstock, NY 12498

Nestled in the heart of Woodstock, this extraordinary 70+ acre estate is a rare offering of artistic heritage, architectural beauty, and serene natural surroundings. Known as The Stone House on Striebel Road, this iconic bluestone compound has stood at the crossroads of music, literature, and counterculture for over a century.Built in 1914 as a country retreat, the main Stone House

Kathryn Johnson William Pitt Sothebys Int Rlty

18 Striebel Rd, Woodstock, NY 12498
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Not Listed For Sale
- 4 Beds
- 6.5 Baths
- 3,746 Sq Ft
15 Silver Wings Ln, Woodstock, NY 12498

15 Silver Wings Ln, Woodstock, NY 12498

/38
$795,000
- 3 Beds
- 2 Baths
- 2,390 Sq Ft
1 Bellows Ln, Woodstock, NY 12498

Welcome to Blues Quarry—where tucked-away tranquility meets ''close to everything'' convenience in the heart of Woodstock, NY.This 2.78-acre ridge-top retreat offers a seasonal stream below, plenty of flat usable land up top, and a landscape framed by a sweeping lawn, mature flower gardens, and wooded privacy.For the dreamers and doers: a dog kennel with fenced yard can keep its current

Baris Demirel Serhant LLC

1 Bellows Ln, Woodstock, NY 12498
/39
$660,000 Sold Aug 21, 2025
- 1,564 Sq Ft
- $422/SF
- 159 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1968
36 Oriole Dr, Woodstock, NY 12498

Nestled in the heart of Woodstock, this beautifully remodeled 4-bedroom, 2.5- bathroom home seamlessly blends modern comfort with timeless charms. With an open-concept layout and soaring vaulted ceilings, the home feels both spacious and inviting. Original hardwood floors run throughout, adding warmth and character. The custom-designed kitchen is a chef's dream, featuring brand new

Eliana Amodio Amodio Real Estate & Prop

36 Oriole Dr, Woodstock, NY 12498

/2
Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,288 Sq Ft
378 Ohayo Mountain Rd, Woodstock, NY 12498

378 Ohayo Mountain Rd, Woodstock, NY 12498

/62
$799,000
- 2 Beds
- 1 Bath
- 1,256 Sq Ft
90 Aarons Way, Mount Tremper, NY 12457

Tucked away at the end of a quiet private road near the top of Roundtop Mountain, this 2-bedroom, 1-bath home offers serene seclusion surrounded by protected DEP land and a private forest preserve. A true nature lover's paradise, the property is alive with wildlife and boasts beautifully landscaped grounds, seasonal mountain views, and the potential for year-round vistas with the clearing of

Darlene Griffin Halter Associates Realty

90 Aarons Way, Mount Tremper, NY 12457
/40
$1,055,000 Sold Aug 20, 2025
- 1,589 Sq Ft
- $664/SF
- 34 Days On Market
- 4 Beds
- 3 Baths
- Built 2016
10 Magnolia Trail, Woodstock, NY 12498

Tucked away at the end of a long, meandering private drive, this country retreat offers the opportunity to embrace serenity, privacy, and refined rural living. Set on an idyllic 4.4-acre parcel, this residence was designed to harmonize effortlessly with the surrounding woodlands.The home's expansive picture windows and open-concept great room create a seamless flow between indoors and

Joseph Satto Fresh Air Realty

10 Magnolia Trail, Woodstock, NY 12498

/32
Est $732,479 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 3,843 Sq Ft
2608 Route 212, Woodstock, NY 12498

2608 Route 212, Woodstock, NY 12498

/45
$895,000
- 4 Beds
- 3 Baths
- 2,044 Sq Ft
4868 New York 212, Willow, NY 12495

Escape to the Catskills with this exquisitely remodeled home in Willow - where privacy, luxury, and mountain views converge on 3.6 pristine acres just minutes from the heart of Woodstock. This 5-bedroom, 3-bathroom home is a masterclass in modern design and thoughtful craftsmanship, with every detail curated for comfort, style, and effortless living. Inside, you'll find an airy open-concept

Richard Vizzini Corcoran Country Living

4868 New York 212, Willow, NY 12495
/28
$503,650 Sold Aug 14, 2025
- 1,867 Sq Ft
- $270/SF
- 93 Days On Market
- 3 Beds
- 2 Baths
- Built 1955
44 Mink Hollow Rd, Willow, NY 12495

Charming sun-drenched ranch in the Woodstock hamlet of Lake Hill. Nestled among towering pines and lush rhododendrons, this delightful ranch offers a perfect blend of comfort, convenience, and natural beauty. A long, private driveway welcomes you to this deceptively spacious home, offering over 1,860 square feet of single-level living. Inside, the expansive living room is bathed in natural light

Lisa Halter Halter Associates Realty

44 Mink Hollow Rd, Willow, NY 12495

/35
Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,870 Sq Ft
2292 Glasco Turnpike, Woodstock, NY 12498

2292 Glasco Turnpike, Woodstock, NY 12498

/43
$1,350,000
- 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
/37
$745,000 Sold Aug 13, 2025
- 1,498 Sq Ft
- $497/SF
- 86 Days On Market
- 4 Beds
- 2 Baths
- Built 1922
2366 Glasco Turnpike, Woodstock, NY 12498

In the heart of the storied Byrdcliffe Colony, you will find this classic Woodstock retreat.Cited perfectly on 2 landscaped acres, featuring flowering trees , fruit trees and a variety of seasonal blooms.Just one mile from the center of town and everything Woodstock has to offer.Four bedrooms and 2 Full baths provide room and comfort for family and friends.Heated and plumbed

Margo Obourn Win Morrison Realty - W

2366 Glasco Turnpike, Woodstock, NY 12498

/34
Est $779,475 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,201 Sq Ft
5249 Route 212, Mount Tremper, NY 12457

5249 Route 212, Mount Tremper, NY 12457

/45
$1,250,000
- 3 Beds
- 2.5 Baths
- 3,080 Sq Ft
11 Grogkill Rd, Willow, NY 12495

This property has an accepted offer. Classic Country ''Haven'' — it's HEAVEN really! Elegance that checks off every box! This timeless and enduring style home designed with graciously proportioned rooms with high ceilings and light streaming through windows from every direction. Centrally located and perched on 3 exclusive landscaped acres with a pool, an oversized 2-car garage, and mountain

Sharon Breslau BHHS Hudson Valley Properties

11 Grogkill Rd, Willow, NY 12495
/42
$545,000 Sold Aug 09, 2025
- 1,180 Sq Ft
- $462/SF
- 75 Days On Market
- 3 Beds
- 2 Baths
- Built 1988
180 W Hurley Rd, Woodstock, NY 12498

Welcome to this beautifully renovated 3-bedroom, 2-bathroom home located just minutes from the heart of Woodstock. With all-new carpeting throughout, a brand-new kitchen, and fully updated bathrooms, this turn-key property offers effortless comfort and style from the moment you step inside.Cozy up by the fireplace on chilly evenings, or enjoy warm-weather days in the expansive

Savannah Miceli Century 21 Alliance-NP

180 W Hurley Rd, Woodstock, NY 12498

/33
Est $514,574 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,517 Sq Ft
1585 Glasco Turnpike, Woodstock, NY 12498

1585 Glasco Turnpike, Woodstock, NY 12498

/38
$795,000
- 2 Beds
- 1 Bath
- 1,250 Sq Ft
276 Chestnut Hill Rd, Woodstock, NY 12498

Tucked back on a six acre lot just minutes to the town of Woodstock sits this fairytale two bedroom cottage. The woodland view is yours to explore, the deep forest of evergreens, ferns and moss. Inside, you're tucked into charming spaces or enjoying the expansive Great Room, with a stone fireplace at the center and vaulted ceilings with beautiful exposed beams. A wall of windows frames the view.

Annabel Taylor Four Seasons Sotheby's Int.

276 Chestnut Hill Rd, Woodstock, NY 12498
/39
$999,000 Sold Aug 08, 2025
- 3,010 Sq Ft
- $332/SF
- 38 Days On Market
- 3 Beds
- 2 Baths
- Built 1967
115 Jones Quarry Rd, Woodstock, NY 12498

Recipe for a stunning contemporary home...Take one solid, classic, ranch, in an extraordinary setting just 2 miles from the iconic Village of Woodstock! Add approximately 1,500 sq ft of beautiful and thoughtfully designed additions and voila!....You have this extraordinary and stunning Contemporary!Discover this exceptional 3-bedroom, 2-bath contemporary home nestled on 2.38 beautifully

Margo Obourn Win Morrison Realty - W

115 Jones Quarry Rd, Woodstock, NY 12498

/14
Est $791,130 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,416 Sq Ft
15 Lake View Dr, Lake Hill, NY 12448

15 Lake View Dr, Lake Hill, NY 12448

/56
$1,295,000
- 4 Beds
- 2 Baths
- 2,377 Sq Ft
35 Abbey Rd, Mount Tremper, NY 12457

35 Abbey Road — A Mid-Century Sanctuary minutes from Woodstock TownTucked away off of Abbey Rd and just a short pass over a charming stream you'll arrive at this pristine, authentic mid-century retreat, nestled in the heart of Woodstock's beloved Abbey Road. Set on 5.4 magical acres, this serene property captures the essence of Catskills living- graceful, grounded, and surrounded by

Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

35 Abbey Rd, Mount Tremper, NY 12457
/32
$1,800,000 Sold Aug 06, 2025
- 2,247 Sq Ft
- $801/SF
- 21 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1989
11 Lion's Way, Bearsville, NY 12409

This unique home blends nature with breathtaking views, high design, a whimsical feel, along with modern efficient systems that will leave you in awe. Nestled on a secluded 47-acre property just minutes from the heart of Woodstock Village, this Mountainside Retreat is perfectly situated above Cooper Lake, offering long-distance views of some of the most sought-after peaks in the Catskills,

Sheena Lepez Compass Greater New York, LLC

11 Lion's Way, Bearsville, NY 12409

/32
Est $2,405,127 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,954 Sq Ft
34 Vandebogart Rd, Woodstock, NY 12498

34 Vandebogart Rd, Woodstock, NY 12498

/28
$1,150,000
- 3 Beds
- 2 Baths
- 1,948 Sq Ft
99 Cannon Cir, Woodstock, NY 12498

Tucked away in the pristine Ohayo Mountain forest and less than a mile from the heart of Woodstock, Cannon House offers the rare combination of seclusion, comfort, and modern design. Set on 1.65 acres, this contemporary retreat, built in 2020, is thoughtfully designed to immerse you in the natural surroundings while providing every modern convenience. With three bedrooms and two and a half baths,

Laurie Ylvisaker Coldwell Banker Village Green

99 Cannon Cir, Woodstock, NY 12498
/44
$1,700,000 Sold Jul 31, 2025
- 2,210 Sq Ft
- $769/SF
- 29 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1995
299 California Quarry Rd, Woodstock, NY 12498

Live an Elevated Life!Perched high on iconic Overlook Mountain near the end of a private road — just minutes from the heart of Woodstock—this striking Modern contemporary home delivers jaw-dropping, panoramic views that stretch from the Catskills to the Hudson River, including Mohonk and the Ashokan Reservoir. It's the ultimate mountaintop escape: private, peaceful, and designed for

Lisa Cooper Serhant LLC

299 California Quarry Rd, Woodstock, NY 12498

/22
Est $578,418 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,106 Sq Ft
6 Allen Dr, Woodstock, NY 12498

6 Allen Dr, Woodstock, NY 12498

/38
$889,000 Pending
- 4 Beds
- 3 Baths
- 2,125 Sq Ft
48 Cooper Hollow Ln, Bearsville, NY 12409

Tucked away on a scenic country road just minutes from historic Woodstock, this stunning contemporary home offers the perfect balance of privacy, tranquility, and access to nature. Set on six acres in a highly desirable neighborhood, this serene retreat is surrounded by lush woods, artfully landscaped grounds, and a feeling of peace that begins the moment you arrive. With nearby hiking trails,

Eric Amaral Coldwell Banker Village Green

48 Cooper Hollow Ln, Bearsville, NY 12409
/47
$367,000 Sold Jul 28, 2025
- 894 Sq Ft
- $411/SF
- 70 Days On Market
- 3 Beds
- 1 Bath
- Built 1954
30 Dixon Ave, Woodstock, NY 12498

Charming 3-Bedroom Ranch in Prime Woodstock Location! 30 Dixon Ave in Woodstock is a sunny, well-maintained 3 bedroom, 1 bath ranch that sits on a quiet street just minutes from the heart of Woodstock. With single level living and community rich location, it offers a rare opportunity to own a home in this special part of the Hudson Valley.Sold As Is the home retains much of its

Darlene Griffin Halter Associates Realty

30 Dixon Ave, Woodstock, NY 12498

/35
Est $534,612 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,166 Sq Ft
15 Niles Dr, Woodstock, NY 12498

15 Niles Dr, Woodstock, NY 12498

/56
$889,000 Pending
- 4 Beds
- 3 Baths
- 2,125 Sq Ft
48 Cooper Hollow Rd, Bearsville, NY 12409

Tucked away on a scenic country road just minutes from historic Woodstock, this stunning contemporary home offers the perfect balance of privacy, tranquility, and access to nature. Set on six acres in a highly desirable neighborhood, this serene retreat is surrounded by lush woods, artfully landscaped grounds, and a feeling of peace that begins the moment you arrive. With nearby hiking trails,

Eric Amaral Coldwell Banker Village Green

48 Cooper Hollow Rd, Bearsville, NY 12409
/26
$510,000 Sold Jul 28, 2025
- 1,912 Sq Ft
- $267/SF
- 204 Days On Market
- 4 Beds
- 1 Bath
- Built 1926
386 Wittenberg Rd, Bearsville, NY 12409

This charming 1926 Craftsman in Woodstock, NY has been patiently waiting for its next chapter. With a little TLC, it has the bones, location, and timeless appeal to become a truly special home. Step back in time as you enter this classic residence, rich in character and craftsmanship rarely found today. Imagine cozy evenings by the fireplace, surrounded by original details just waiting to be

Melissa Zoe Hirsch Coldwell Banker Village Green

386 Wittenberg Rd, Bearsville, NY 12409

/29
Est $514,741 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,029 Sq Ft
12 Niles Dr, Woodstock, NY 12498

12 Niles Dr, Woodstock, NY 12498

/42
$1,495,000 Pending
- 2 Beds
- 4 Baths
- 2,727 Sq Ft
96 Meads Mountain Rd, Woodstock, NY 12498

Tucked away on 7.26 acres of lush, storybook landscape with a stream-fed pond, this quintessential Woodstock home is more than a residence-it's an experience. As you approach via a winding driveway that crosses a babbling stream and year-round waterfalls, the magic begins. You can hear the cascading water from the house itself, setting the tone for the serenity that follows. The main home offers

Lisa Halter HALTER ASSOCIATES REALTY INC

96 Meads Mountain Rd, Woodstock, NY 12498
/35
$2,300,000 Sold Jul 25, 2025
- 2,896 Sq Ft
- $794/SF
- 28 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1995
150 Meads Mountain Rd, Woodstock, NY 12498

Perched high on Overlook Mountain just a mile from the heart of Woodstock, this striking contemporary residence—designed and built in 1995 by the iconic Bananas of Woodstock—is a rare architectural gem that seamlessly blends creativity, quality, and comfort.Privately sited among the trees, the home's unique design is constructed with steel beams throughout, cleverly concealed beneath rich

Melissa Mayes Serhant LLC

150 Meads Mountain Rd, Woodstock, NY 12498

/35
Est $612,229 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,259 Sq Ft
157 Van Dale Rd, Woodstock, NY 12498

157 Van Dale Rd, Woodstock, NY 12498

/32
$859,000 Pending
- 4 Beds
- 2 Baths
- 1,285 Sq Ft
4 Munchkin Ln, Kingston, NY 12401

Highwoods Haven rests on just over two whisper-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

Leslie Foti Coldwell Banker Village Green

4 Munchkin Ln, Kingston, NY 12401
/27
$650,000 Sold Jul 25, 2025
- 850 Sq Ft
- $765/SF
- 43 Days On Market
- 1 Bed
- 1 Bath
- Built 1974
30 Little Deer Rd, Mount Tremper, NY 12457

30 Little Deer Rd — Redefining ''Cabin Fever'' in Style.Welcome to your chic, modern escape nestled on three private, wooded acres in Mount Tremper, just minutes from the vibrant village of Woodstock. This stunning cabin has undergone a full top-to-bottom renovation, transforming the traditional cabin experience into a luxurious retreat.Thoughtfully designed and impeccably

Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

30 Little Deer Rd, Mount Tremper, NY 12457

/27
Est $562,300 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,012 Sq Ft
3 Niles Dr, Woodstock, NY 12498

3 Niles Dr, Woodstock, NY 12498

/31
$895,000 Pending
- 4 Beds
- 2 Baths
- 2,227 Sq Ft
94 Silver Hollow Rd, Willow, NY 12495

Idyllic Country Retreat Nestled Among Majestic PinesEscape to this enchanting country home, embraced by towering pines and the soothing sounds of a nearby stream. Whether you're seeking a peaceful getaway or a full-time residence, this spacious and beautifully renovated home is ready to welcome you.Step inside the expansive living room, where exposed beams, vaulted ceilings, and a

Alexis Li Corcoran Country Living

94 Silver Hollow Rd, Willow, NY 12495
/18
$301,250 Sold Jul 25, 2025
- 1,266 Sq Ft
- $238/SF
- 32 Days On Market
- 3 Beds
- 1 Bath
- Built 1961
24 Overlook Dr, Woodstock, NY 12498

Create Your Dream Home in Woodstock - Perfect for DIY Enthusiasts! Embrace the opportunity to finish this one-level, 3-bedroom home in the heart of Woodstock. With renovations already underway, this property is ideal for hands-on buyers ready to bring their vision to life.The flexible extra room offers endless possibilities—finish it out for additional living space, convert it back into a

Laura Haney Halter Associates Realty

24 Overlook Dr, Woodstock, NY 12498

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