28

Woodstock, NY Homes for Sale with Acreage

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  • /46

    $799,000

    • 3 Beds
    • 2 Baths
    • 2,196 Sq Ft

    26 Carle Rd, Mount Tremper, NY 12457

    Breathtaking mountain views set the stage at 26 Carle Rd in Mount Tremper, a custom 3-story Contemporary that truly reflects the spirit of the Catskills. With 3 bedrooms, 2 baths, and an open floor plan, the home offers both comfort and serenity. The centerpiece is a dramatic stone fireplace with a wood-burning insert, its chimney running through all three levels and filling the home with warmth

    Agent Photo

    Elizabeth 'Beth' Alfeld

    Keller Williams Hudson Valley

    (845) 448-2330

    26 Carle Rd, Mount Tremper, NY 12457
  • /21

    $525,000

    • 4 Beds
    • 1.5 Baths
    • 1,669 Sq Ft

    78 van de Bogart Rd, Woodstock, NY 12498

    Located on quiet road just minutes from the heart of Woodstock, 78 Van de Bogart Road offers the perfect blend of mid-century charm and modern convivence This home sits on a premier corner one acre lot, meticulously landscaped to provide both curb appeal and a serene, private sanctuary. The upper level of this raised ranch features an open, airy layout designed to bring the outside indoors. The

    Melissa Zoe Hirsch Coldwell Banker Village Green

    78 van de Bogart Rd, Woodstock, NY 12498
  • /52

    $1,340,000

    • 2 Beds
    • 2 Baths
    • 1,560 Sq Ft

    66 Plochmann Ln, Woodstock, NY 12498

    So close yet so far away! Walk to town from your totally private and like-new timber frame home with soaring 23-foot ceilings and walls of windows to bring nature in. As you enter from one of Woodstock's most coveted roads, through the stately pillars, you will feel a sense of tranquility with nature on this 9.94-acre lot that is just a half mile from the village of Woodstock and less than a half

    Mercedes Ross Coldwell Banker Village Green

    66 Plochmann Ln, Woodstock, NY 12498
  • /31

    $525,000

    • 2 Beds
    • 2 Baths
    • 1,130 Sq Ft

    233 Wittenberg Rd, Bearsville, NY 12409

    Picture yourself in this charming 1940 cottage with a roaring fire in its fieldstone double-height fireplace. If that doesn't capture your heart, the open living and dining areas with birch beamed ceilings will. Large expanses of windows flood the space with light, adding more charm essential to modern living. A wonderfully convenient full bath with claw-foot tub adds to the easy living. The

    Henry Ford Coldwell Banker Village Green

    233 Wittenberg Rd, Bearsville, NY 12409
  • /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
  • /33

    $1,888,000

    • Land
    • 60.94 Acres
    • $30,981 per Acre

    TBD Zena Rd, Woodstock, NY 12498

    An incredible, rare opportunity in Woodstock. It has been very long time since a parcel of this magnitude has available for sale in Woodstock. This contiguous 60-acre property, consisting of two 30-acre lots, features rolling hills, stunning rock outcroppings, mountain views, and diverse mature trees, uniquely offering both beauty and potential. A privately built road, completed by the

    Baris Demirel Serhant LLC

    TBD Zena Rd, Woodstock, NY 12498
  • /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
  • /24

    $2,400,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,420 Sq Ft

    420 Wittenberg Rd, Bearsville, NY 12409

    Woodstock Custom Compound - Create your own private family compound on 2.44 serene acres in the Woodstock Hamlet of Wittenberg—an exceptional to-be-built offering that brings together architectural vision, artisan materials, and the craftsmanship of noted builder James Nelson. This unique project includes a three-bedroom, three-and-a-half-bath main residence, a one-bedroom guest house, and a

    Peter Cantine Halter Associates Realty

    420 Wittenberg Rd, Bearsville, NY 12409
  • /13

    $135,000

    • Land
    • 1.99 Acres
    • $67,839 per Acre

    TBD Cross Patch Rd, Willow, NY 12495

    Sited on a quiet country road, this beautiful 1.99-acre parcel offers a peaceful and picturesque setting surrounded by nature. Once part of an old sheep farm, the property carries a touch of history and rustic charm. Backing up to the scenic Silver Hollow Creek, it provides a serene backdrop perfect for your dream home or weekend retreat. Conveniently located, minutes to the Village of Woodstock,

    Sharon Farley Corcoran Country Living

    TBD Cross Patch Rd, Willow, NY 12495
  • /103

    $6,700,000

    • 3 Beds
    • 6 Baths
    • 4,688 Sq Ft

    125 Valley View Way, Lake Hill, NY 12448

    Welcome to Nature's Edge -- a Woodstock estate, where wilderness meets luxury. Perched at the end of a secluded private road, this modern mountain marvel offers unmatched privacy, serenity, and grandeur. Surrounded by natural woodscapes and native rock outcroppings, this 40 acre property sits adjacent to over 500 acres of forever wild NYC DEP land. The home itself, a Barry Price architectural

    Heidi Rothe Grist Mill Real Estate

    125 Valley View Way, Lake Hill, NY 12448
  • /18

    $799,000

    • Land
    • 27.19 Acres
    • $29,386 per Acre

    TBD MacDaniel Rd, Bearsville, NY 12409

    Pollinator's Pathway in Woodstock Discover 27+ acres of untouched beauty just steps from the Tibetan Monastery, Magic Meadow, and the trailheads to Meads Mountain and Overlook Mountain. A private, winding ~.5-mile driveway opens to a sunlit clearing alive with wildflowers and pollinator plants — a natural canvas awaiting your vision. With selective tree trimming, sweeping Catskill Mountain views

    Genevieve Geaney Compass Greater New York, LLC

    TBD MacDaniel Rd, Bearsville, NY 12409
  • /35

    $1,200,000

    • Land
    • 75.4 Acres
    • $15,915 per Acre

    626 Wittenberg Rd, Bearsville, NY 12409

    Magnificent 8+ acre meadow across from Cold Brook Road PLUS 66 acres of beautiful rolling property with two streams and magical wet and dry areas in the woods. Possible single Estate property or subdivide into several parcels. Access from Wittenberg Road and views nestled in the Wittenberg Valley just past where the roads to Glenford, Mt. Tremper and Bearsville meet. Property has access on

    Robert Stang LIVEARTHCO CONSULTING LLC

    626 Wittenberg Rd, Bearsville, NY 12409
  • /33

    $569,000

    • 2 Beds
    • 2 Baths
    • 1,300 Sq Ft

    328 John Joy Rd, Woodstock, NY 12498

    Nearly Six Lush, Scenic And Private Acres Located Eight Minutes From The Heart Of Woodstock! This Home Features Two / Possibly Three Bedrooms And Two Full Baths. Meticulously Maintained! Enjoy Sunrises Or Sunsets From The Wrap Around Deck. Relax And Take In All Of The Tranquility While Sitting Stream Side Or Enjoy The Changing Of The Leaves During The Beautiful Fall Season While Sipping Hot Cocoa

    Michael Alpert Daniel Gale Sothebys Intl Rlty

    328 John Joy Rd, Woodstock, NY 12498
  • /22

    $699,000

    • 4 Beds
    • 2.5 Baths
    • 2,471 Sq Ft

    19 Livingston Ct, Woodstock, NY 12498

    Accepted offer, continue to show. Sophisticated Gated Retreat in Woodstock. Tucked within a serene, tree-lined neighborhood, this privately sited 4-bedroom, 2.5-bathroom colonial blends timeless comfort with thoughtful modern upgrades. Set behind a gated entry and encircled by approximately one acre of deer fencing, the property offers rare privacy while remaining minutes from the heart of

    Timothy Ayers Berardi Realty

    19 Livingston Ct, Woodstock, NY 12498
  • /28

    $1,888,000

    • Land
    • 60.94 Acres
    • $30,981 per Acre

    TBD 60 Acre Zena Rd, Woodstock, NY 12498

    An incredible, rare opportunity in Woodstock.It has been very long time since a parcel of this magnitude has available for sale in Woodstock. This contiguous 60-acre property, consisting of two 30-acre lots, features rolling hills, stunning rock outcroppings, mountain views, and diverse mature trees, uniquely offering both beauty and potential. A privately built road, completed by the

    Baris Demirel Serhant LLC

    TBD 60 Acre Zena Rd, Woodstock, NY 12498
  • /36

    $1,195,000

    • 3 Beds
    • 4 Baths
    • 3,120 Sq Ft

    540 Mount Tobias Rd, Mount Tremper, NY 12457

    Step into the pages of Dwell magazine and immerse yourself in this architect-designed gem offering a harmonious blend of modern design and natural beauty. Feel a wave of calm wash over you, greeted by resplendent views, clean lines, and a wall of windows overlooking majestic mountain vistas. Modernists rejoice. Design aficionados delight. And nature enthusiasts revel. A minimalist aesthetic

    Alexander James Compass Greater NY, LLC

    540 Mount Tobias Rd, Mount Tremper, NY 12457
  • /42

    $1,199,000

    • 5 Beds
    • 3 Baths
    • 3,696 Sq Ft

    3207-3209 New York 212, Bearsville, NY 12409

    Enchanting Woodstock Compound with three separate buildings—Craftsman Home, Historic Barn & Cottage. 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,

    Michelle Bergkamp William Pitt Sothebys Int Rlty

    3207-3209 New York 212, Bearsville, NY 12409
  • /72

    $1,495,000

    • 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 deeply rooted in American music. Originally built in 1873 and once home to famed 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

    Jessica Brasseur Houlihan Lawrence Millbrook Of

    1 Wittenberg Rd, Bearsville, NY 12409
  • /34

    $1,475,000

    • Land
    • 25.38 Acres
    • $58,117 per Acre

    132 Valley View Way, Woodstock, NY 12448

    The Ledges at Valley View High above the Beaverkill River, where the Catskills unfold in a sweep of peaks and light, lies The Ledges at Valley View - a design-ready estate site where modern architecture meets the mountain. Sited on more than 25 private acres, this south-facing ridgeline property captures cinematic views of Twin, Indian Head, Overlook, and Mount Guardian. The land adjoins

    Margaret Bellar The Catskill Dream Team

    132 Valley View Way, Woodstock, NY 12448
  • /61

    $775,000

    • 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
  • /31

    $2,500,000

    • 5 Beds
    • 4.5 Baths
    • 2,978 Sq Ft

    177 Tinker St, Woodstock, NY 12498

    Fall in love with this artfully reimagined and expanded 1930 farmhouse, privately set on a gentle hill just moments from the heart of Woodstock. Rich in history and character, this special home was once owned by Michael Lang, the legendary founder of the 1969 Woodstock Festival—adding a rare and meaningful connection to the town's iconic past.Thoughtfully renovated, the home offers a

    Joan Capria Four Seasons Sotheby's Int'l R

    177 Tinker St, Woodstock, NY 12498
  • /6

    $184,900

    • Land
    • 2.31 Acres
    • $80,043 per Acre

    100 Zena Rd, Woodstock, NY 12498

    One of the last commercial lots in Woodstock. Zoned neighborhood commercial..excellent drainage. Great location for nursery school, medical or dental clinic, funeral home, or professional office, bank retail mix strip complex. Based on Zoning and bulk requirements site can facilitate approx. 16,000 sq. ft. of building...Soil has excellent drainage for inground septic system. The Town Building

    Michael Bernholz Sr. Hudson Valley Appraisal

    100 Zena Rd, Woodstock, NY 12498
  • /51

    $759,000

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

    97 John Joy Rd, Woodstock, NY 12498

    The best of both worlds!A boho cottage paradise and a modern ADU (Accessory Dwelling Unit). Peace and tranquility and 3 miles from the center of the most famous small town in the world. Five-star dining and unique shopping opportunities. The property is situated adjacent to the Thorne Preserve - 60 acres boasting the most painted views of Overlook Mountain. The preserve is a sweeping

    Benjamin Armento Coldwell Banker Village Green

    97 John Joy Rd, Woodstock, NY 12498
  • /36

    $729,000

    • 2 Beds
    • 2 Baths
    • 2,678 Sq Ft

    404 John Joy Rd, Woodstock, NY 12498

    Old Woodstock charm awaits you at this contemporary gentleman's farm set on 3.4 peaceful, park-like acres. Built in 1968, this property is ready to be reinvigorated with your personal vision and style. The home spans nearly 2,700 square feet, includes two bedrooms and two bathrooms, home office, bay windows, skylights, fireplace, French doors, Pentair water filtration system, and so much more.

    Edward Taraskewich Howard Hanna Rand Realty

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

    $3,500,000

    • 4 Beds
    • 4 Baths
    • 4,201 Sq Ft

    289 Upper Byrdcliffe Rd, Woodstock, NY 12498

    Set on nearly 9 serene acres in the heart of Woodstock's historic Byrdcliffe Arts Colony is a rare synthesis of architectural precision and natural harmony—an embodiment of award-winning architect John Storyk's deep understanding of space, sound, and site. Designed in 1969 at the very beginning of Storyk's now-legendary career—just after his groundbreaking work on Jimi Hendrix's Electric Lady

    Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

    289 Upper Byrdcliffe Rd, Woodstock, NY 12498
  • /15

    $499,000

    • Land
    • 10 Acres
    • $49,900 per Acre

    547 Glenford Wittenberg Rd, Bearsville, NY 12409

    This is an 86.2 acre property that is being subdivided into two- 3 acre parcels and one-10 acre parcel. The 10 ac parcel will be on the pond and the two 3 acre parcels are across the street from Yankeetown Pond. There are no houses for sale just land. There are beautiful views of the mountains and of Yankee Town Pond. The 10 acre parcel on the pond can have a structure build on it. There are 2+

    Siobhan Scanlan Win Morrison Realty-K

    547 Glenford Wittenberg Rd, Bearsville, NY 12409
  • /23

    $600,000

    • Land
    • 5.45 Acres
    • $110,092 per Acre

    326 Raycliffe Dr, Woodstock, NY 12498

    Discover a rare opportunity to own 5.45 acres atop one of Woodstock's most coveted locations. This private, east-facing lot offers panoramic views that stretch endlessly over the Catskill Mountains, providing an awe-inspiring backdrop for your dream home. With the space and natural beauty to build a sleek, modern estate, this land is the perfect canvas for a luxury retreat. Surrounded by the

    Alexis Li Corcoran Country Living

    326 Raycliffe Dr, Woodstock, NY 12498
  • /42

    $899,000

    • 5 Beds
    • 2 Baths
    • 1,764 Sq Ft

    1311 Wittenberg Rd, Mount Tremper, NY 12457

    Set well back from the road behind a handsome gated entry, this modern Catskills hideaway delivers the privacy everyone wants and the volume everyone hopes for. The approach is long and quiet; the house reveals itself slowly—wrapped by trees, with sky above and room to breathe on 4.04 acres. Inside, an airy great room rises with high ceilings and broad windows that pull in daylight and treetops.

    WINTON MORRISON Win Morrison Realty - W

    1311 Wittenberg Rd, Mount Tremper, NY 12457

Home Trends in Woodstock, NY

Housing Trends

Median Sale Price
$703,000
Median Single Family Sale Price
$700,000
Median Townhouse Sale Price
$775,000
Average Price Per Sq Ft
$436
Number of Homes for Sale
15
Last 12 months Home Sales
130
Months of Supply
1.40
Median List Price
$749,450
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
12%
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