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Woodstock, NY Homes for Sale with Basement

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  • /32

    $1,195,000

    • 4 Beds
    • 6 Baths
    • 2,980 Sq Ft

    12 Tinker St, Woodstock, NY 12498

    Prime Village Green Historic Gem in Woodstock, NY. Discover a unique opportunity to own a piece of history in the heart of Woodstock. This remarkable 1875 era property originally known as The Snyder Homestead named after its original owner, was the grandest house in town. This old style home with its distinctive Mansard roof retains its grandeur to this day. It offers the quintessential blend of

    Agent Photo

    Danielle Sevier

    Compass Greater NY, LLC

    (845) 436-3857

    12 Tinker St, Woodstock, NY 12498
  • /31

    $975,000

    • 4 Beds
    • 4 Baths
    • 1,811 Sq Ft

    33 Tannery Brook Rd, Woodstock, NY 12498

    Nestled in the heart of Woodstock, this beautifully transformed farmhouse, originally constructed in the 1870s, seamlessly blends historic charm with modern living. The current owners, a talented architect and interior designer, have meticulously renovated this property to enhance its original architecture while maximizing natural light and integrating the surrounding landscape. The zoning allows

    Agent Photo

    Danielle Sevier

    Compass Greater NY, LLC

    (845) 456-8466

    33 Tannery Brook Rd, Woodstock, NY 12498
  • /26

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,334 Sq Ft

    40 Mink Hollow Rd, Willow, NY 12495

    Nestled into 2 lush acres in legendary Woodstock, NY, Kate's Lazy Cabin is a one-of-a-kind creative escape owned by iconic B-52s lead singer Kate Pierson and renowned artist Monica Coleman. This rustic offering radiates eclectic soul, bold personality, and a deep connection to creativity—just like the town it calls home.The house itself is a layered expression of vintage charm and artistic

    Agent Photo

    Diana Polack

    Compass Greater NY, LLC

    (845) 605-7386

    40 Mink Hollow Rd, Willow, NY 12495
  • /77

    $5,200,000

    • 10 Beds
    • 8 Baths
    • 7,991 Sq Ft

    16-26 Shultis Brook Rd, Bearsville, NY 12409

    Historic compound located in the iconic hamlet of Bearsville, just minutes from the Village of Woodstock. This four residence compound dates back to the mid-1700's and is believed to be the first farm in the valley as well as one of the first homes. Sprawled over 25+ acres with a pond and meandering stream, this unique property tucked away with complete privacy. The four structures include a 3+

    Agent Photo

    Amy Hawks

    Berardi Realty

    (845) 250-0616

    16-26 Shultis Brook Rd, Bearsville, NY 12409
  • /43

    $1,199,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,088 Sq Ft

    178 Chestnut Hill Rd, Woodstock, NY 12498

    Discover the epitome of modern luxury in this brand new build, with a sleek aesthetic that seamlessly blends style and comfort. Using ecological and state of the art building practices highlighted by exceptional craftsmanship and distinctive design. Ascend an impressive switchback floating staircase to a stunning wall of windows that flood the open concept, living, kitchen, and dining area

    Richard Vizzini Corcoran Country Living

    178 Chestnut Hill Rd, Woodstock, NY 12498
  • /51

    $1,750,000

    • 2 Beds
    • 2 Baths
    • 1,531 Sq Ft

    128 Newcut Rd, Bearsville, NY 12409

    Nestled atop your very own private mountaintop, this captivating retreat is the sanctuary you've been dreaming of. Enjoy 35 acres of serene woodland and breathtaking views. This residence is the ultimate escape for weekenders, outdoor enthusiasts, and creatives seeking the solitude necessary to ignite their next masterpiece.A peaceful haven with expansive mountain vistas, you'll find

    Heidi Maloney Four Seasons Sotheby's Int'l R

    128 Newcut Rd, Bearsville, NY 12409
  • /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
  • /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

    $1,495,000

    • 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
  • /36

    $1,295,000 Open House 9/21

    • 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
  • /31

    $999,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,252 Sq Ft

    32 Maurizi Ln, Woodstock, NY 12498

    Blending classic country charm with modern sophistication, this newly built modern farmhouse offers over 3,000 square feet of beautifully finished living space. Designed with clean lines, a neutral palette, and layered textures, it delivers a timeless aesthetic full of warmth and character. The home features four spacious bedrooms, three and a half baths, a fully finished lower level, and

    Richard Vizzini Corcoran Country Living

    32 Maurizi Ln, Woodstock, NY 12498
  • /22

    $995,000

    • 5 Beds
    • 2 Baths
    • 2,772 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

    WINTON MORRISON Win Morrison Realty - W

    1311 Wittenberg Rd, Mount Tremper, NY 12457
  • /44

    $679,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 2 Baths
    • 1,469 Sq Ft

    10 Niles Dr, Woodstock, NY 12498

    Meticulous 4-Bedroom Mid-Century Cape Cod/Ranch in Woodstock. Set on 1 acre in a desirable Woodstock neighborhood, this impeccably updated Cape Cod/Ranch blends timeless character with modern comfort. With cedar shake siding, Pella architectural windows, and hardwood floors throughout. The home is both elegant and welcoming.The main level offers easy one level living with a primary

    Amy Owens Coldwell Banker Village Green

    10 Niles Dr, Woodstock, NY 12498
  • /13

    $440,000

    • 1 Bed
    • 1 Bath
    • 841 Sq Ft

    57 Ohayo Mountain Rd, Woodstock, NY 12498

    THE EXCITEMENT AND CONVENIENCE OF WOODSTOCK VILLAGE LIVING! Adorable period bungalow moments from Tinker St. and all the dining, entertainment, shops, hiking, biking and golfing that Woodstock has to offer. This 1 BR, 1 BA charmer features an additional room/four-season sun porch, handsome masonry fireplace with river rock chimney, modern kitchen, a clawfoot tub, separate laundry area,

    Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

    57 Ohayo Mountain Rd, Woodstock, NY 12498
  • /24

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,607 Sq Ft

    311 Wittenberg Rd, Bearsville, NY 12409

    Welcome to the Stone Cottage A home that embodies the spirit of Woodstock with character, warmth and charm. Enter through the vintage kitchen, which opens into a charming dining area , the perfect setting for intimate dinners. The dining area flows seamlessly into the living room, creating the perfect gathering space for family and friends. Vaulted ceilings, wide board pine floors, a

    Anne Rajs Corcoran Country Living

    311 Wittenberg Rd, Bearsville, NY 12409
  • /25

    $699,000

    • 4 Beds
    • 3 Baths
    • 2,208 Sq Ft

    36-38 Ohayo Mountain Rd, Woodstock, NY 12498

    Welcome to The Mill House, nestled in the vibrant heart of Woodstock, NY—a delightful farmhouse that beautifully blends historic charm with modern comforts. Spanning 1,764 square feet, this inviting home includes three cozy bedrooms and two full bathrooms, offering a spacious layout for everyday living.As you wander through the lush gardens and cross a quaint bridge over a seasonal

    Sheena Lepez Compass Greater New York, LLC

    36-38 Ohayo Mountain Rd, Woodstock, NY 12498
  • /39

    $1,985,000

    • 6 Beds
    • 3 Baths
    • 3,023 Sq Ft

    2320 Glasco Turnpike, Woodstock, NY 12498

    For the first time in its history, this 12-acre family estate—designed, built, and cherished by a prominent Woodstock family—comes to market. A rare opportunity for the next generation to build their own private estate or compound, walking distance to town. Complete with babbling brook, waterfall, two vintage Woodstock cottages and acres of woods to explore. A perfect retreat! to your dream

    George Denise Keller Williams Realty HV Nort

    2320 Glasco Turnpike, 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
  • /17

    $2,200,000

    • 8 Beds
    • 10 Baths

    20 Country Club Ln, Wood Stock, NY 12498

    A Rare Opportunity in the Heart of Woodstock. Own a remarkable piece of Woodstock history. Once the site of the Woodstock Lodgeand The Pinecrest, this storied property invites you to step back in time whileenvisioning its next chapter.Set on 6.5 acres of scenic land with a mix of cleared grounds, wooded trails, and aseasonal stream, this property offers a rare combination of

    Kathryn Johnson William Pitt Sothebys Int Rlty

    20 Country Club Ln, Wood Stock, NY 12498
  • /24

    $540,000

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

    5 Violet Place, Woodstock, NY 12498

    Lovely 3-4 bedroom home located in a quiet, friendly neighborhood, just minutes from the shopping, dining, and arts in the village of Woodstock, and about 15 minutes to bustling Kingston and Saugerties. 12 minutes to Thruway, 15 minutes to Trailways bus in Kingston (5 minutes to Woodstock stop), 25 minutes to Rhinecliff Amtrak train station for car-free access to NYC. Upstairs you'll find 3

    Fawn Denue Keller Williams Hudson Valley

    5 Violet Place, Woodstock, NY 12498
  • /62

    $649,000

    • 4 Beds
    • 2 Baths
    • 1,188 Sq Ft

    12 Arnold Dr, Woodstock, NY 12498

    Located on a quiet, country road is this meticulously maintained raised ranch home with ample privacy. Enjoy nature in the many sitting areas in this beautifully landscaped yard with charming bluestone walkway and walls, and lovely shade trees. Upon entering the house the inviting tiled foyer takes you up to the first floor where the first thing you'll notice are those beautiful well cared for

    Rodney Batista Howard Hanna Rand Realty

    12 Arnold Dr, 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
  • /30

    $2,100,000

    • 9 Beds
    • 10 Baths
    • 8,452 Sq Ft

    0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498

    Welcome to Happy Brooks , The much-loved compound for many years of Woodstock Festival co-founder and legendary music industry icon Michael Lang, this mythic Mt. Tremper property boasts true style, along with a creative pedigree that dates back to the 1920s. Originally built for the artist G. Adolph Anderson, the 17 acre estate features three architecturally significant & historic structures

    Nancy Felcetto Brown Harris Stevens Hudson

    0 Wittenberg Rd Unit 20252191, 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
  • /33

    $2,100,000

    • 9 Beds
    • 10 Baths
    • 8,452 Sq Ft

    Unlisted Address

    Welcome to Happy Brooks , The much-loved compound for many years of Woodstock Festival co-founder and legendary music industry icon Michael Lang, this mythic Mt. Tremper property boasts true style, along with a creative pedigree that dates back to the 1920s. Originally built for the artist G. Adolph Anderson, the 17 acre estate features three architecturally significant & historic structures

    Nancy Felcetto Brown Harris Stevens HV LLC

    Unlisted Address
  • /39

    $1,100,000

    • 2 Beds
    • 2 Baths
    • 2,209 Sq Ft

    11 Louie Way, Woodstock, NY 12498

    A spectacular view of Bass Meadow and mountains is just one of the highpoints of this beautiful Cape Cod home on 6.1 acres located a few miles from Woodstock Village. From the home's wraparound stone patio and large windows, imagine looking out at a serene 70-acre vista of meadow and woods that is protected from development. This lovely, turnkey 2209-square-foot home features an open-plan living

    Gary Heckelman Halter Associates Realty Inc

    11 Louie Way, Woodstock, NY 12498
  • /28

    $575,000 Open Sat 12PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,065 Sq Ft

    196 Tinker St, Woodstock, NY 12498

    Country charm -- less than a mile from the Woodstock Village Green! A stream meanders by the massive screened porch and deck. There are also views of your own pond while you enjoy dining al fresco just outside the sliding glass kitchen door. This house transports you to a light, airy, simpler lifestyle. The kitchen opens to a gracious dining room (with a breakfast bar and additional kitchen

    Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

    196 Tinker St, Woodstock, NY 12498
  • /34

    $1,495,000

    • 3 Beds
    • 2 Baths
    • 2,496 Sq Ft

    8 Tannery Brook Rd, Woodstock, NY 12498

    Positioned just moments from the vibrant energy of Tinker Street and the heart of Woodstock, this 2,496 sqft mixed-use property offers an exceptional opportunity to live, work, and invest in one of the Hudson Valley’s most iconic artistic communities. The first floor is owner-occupied, the upstairs serves as a well-established Airbnb, while the street-level commercial space is separately rented,

    STEVEN WROBEL JR. Serhant LLC

    8 Tannery Brook Rd, Woodstock, NY 12498
  • /44

    $1,395,000

    • 4 Beds
    • 4 Baths
    • 3,172 Sq Ft

    5 Downer Ln, Woodstock, NY 12498

    Buckle up! 5 Downer Lane may be themost interesting property you see allyear! This 19th century hand-hewnbarn-to-house conversion has 35 footceilings, tons of sunlight and bespoke stainglass throughout. The layout is wideopen to your own creativity and all the possibilities you can conjure up. Permitted as asuccessful year 'round Airbnb andcurrently configured with

    Carol Graham Corcoran Country Living

    5 Downer Ln, Woodstock, NY 12498
  • /35

    $599,000

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    40 Lower Byrdcliffe Rd, Woodstock, NY 12498

    Nestled in Woodstock's storied Byrdcliffe district, this charming 1920's home balances original character with modern comforts. A comprehensive renovation has introduced thoughtful upgrades throughout, including a brand-new septic system, kitchen and baths, heating system, flooring, and enhanced insulation. Original stained glass windows remain as artistic focal points, honoring the home's

    Sally Sprogis Four Seasons Sotheby's Int'l R

    40 Lower Byrdcliffe Rd, Woodstock, NY 12498
  • /26

    $699,000

    • 3 Beds
    • 2.5 Baths
    • 2,077 Sq Ft

    1521 Glasco Turnpike, Woodstock, NY 12498

    WELL PRICED FOR A TIMELY SALE-Tucked away on 2.2 acres of peaceful, park-like grounds, this inviting home offers the perfect blend of privacy, beauty and convenience. A long gravel driveway winds past tall trees and green space, opening to your own hidden haven—set well back from the road, yet just minutes to Woodstock and Saugerties, with their vibrant shops, restaurants, and culture.The

    Kathryn Johnson William Pitt Sothebys Int Rlty

    1521 Glasco Turnpike, Woodstock, NY 12498
  • /33

    $579,000

    • 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

    Michael Alpert Daniel Gale Sothebys Intl Rlty

    328 John Joy Rd, Woodstock, NY 12498
  • /25

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,376 Sq Ft

    58 Baker Rd, Bearsville, NY 12409

    MOTIVATED SELLER! Discover the perfect blend of comfort, creativity, and seclusion in this charming 3-bedroom, 2-bath home nestled on almost 3 acres of varied landscape—meadows, wooded areas, striking rock outcroppings, and breathtaking mountain views. Whether you’re seeking a full-time residence or a weekend escape, this property offers a unique mix of relaxation and opportunity. Step inside to

    Heather Martin United RE Hudson Valley Edge

    58 Baker Rd, Bearsville, NY 12409
  • /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

    Benjamin Armento Coldwell Banker Village Green

    97 John Joy Rd, Woodstock, NY 12498
  • /79

    $2,500,000

    • 7 Beds
    • 7 Baths
    • 3,960 Sq Ft

    2465 Glasco Turnpike, Woodstock, NY 12498

    Discover a rare opportunity in the heart of Woodstock, NY— with special status, granted by NYS supreme court, which allows rentals of any length, anytime, not subject to any restrictions from the town of Woodstock, or the county. This five-cabin retreat is on over 6 private acres, offering multiple possibilities: a thriving short-term rental, a secluded family/friends compound, or a unique

    Mirav Ozeri The Machree Group, LLC

    2465 Glasco Turnpike, Woodstock, NY 12498
  • /25

    $226,100

    • 3 Beds
    • 2 Baths
    • 944 Sq Ft

    11 Fel Qui Rd, Woodstock, NY 12498

    Tucked away for the ultimate in privacy. This totally affordable cute ranch needs only a little of your attention before moving right in. Lots of land for your peace and quiet as a weekend get away or your primary residence. There are three bedroom and two full bathrooms with an open concept kitchen and living room. If you love being surrounded by nature, being near mountains for skiing and a

    Melissa Terman River Realty Services, Inc.

    11 Fel Qui Rd, Woodstock, NY 12498
  • /37

    $824,000

    • 4 Beds
    • 3 Baths
    • 1,456 Sq Ft

    40 Maxs Place, Kingston, NY 12401

    Tucked away on a quiet private road, this exceptional property offers a rare blend of privacy, style, and resort-like amenities—all just minutes from Woodstock and the best of the Catskills. At the heart of this beautifully updated home is a truly remarkable feature: a 40x60 indoor pool and sauna, creating an all-season sanctuary that's as perfect for quiet morning swims as it is for

    Leigh Wagner-Quintana Keller Williams Realty HV Nort

    40 Maxs Place, Kingston, NY 12401
  • /59

    $769,000

    • 4 Beds
    • 3 Baths
    • 1,804 Sq Ft

    26 Cowboy Trail, Saugerties, NY 12477

    Expansive Cape Cod Retreat in Saugerties - Style, Space & Versatility on 3.6 Private AcresWelcome to your dream home in the heart of Saugerties! This 4000+ sq ft home perfectly blends design with everyday comfort, all set on 3.6 peaceful and private acres in the beautiful Hudson Valley.Inside, you'll find 3 spacious bedrooms and 3 full bathrooms on the main level, along with a

    Ron Knowles Century 21 Alliance-NP

    26 Cowboy Trail, Saugerties, NY 12477

Home Trends in Woodstock, NY

Housing Trends

Median Sale Price
$668,500
Median Single Family Sale Price
$699,000
Median Townhouse Sale Price
$607,500
Average Price Per Sq Ft
$425
Number of Homes for Sale
32
Last 12 months Home Sales
123
Months of Supply
3.10
Median List Price
$744,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
1%
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