22

Woodstock, NY Homes for Sale under $800,000

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  • /34

    $795,000

    • 3 Beds
    • 2 Baths
    • 1,709 Sq Ft

    2614 Glasco Turnpike, Woodstock, NY 12498

    Tucked into the Hillside at Byrdcliffe, halfway up and just below the legendary White Pines of the 300 acre Byrdcliffe sanctuary, is a truly special Woodstock jewel.Hardwood floors flow throughout the easy one-level layout. The spacious living and dining areas fold seamlessly into a generous, bright kitchen, the natural heart of the home. The dining table sits adjacent to a large picture

    Laurie Ylvisaker Coldwell Banker Village Green

    2614 Glasco Turnpike, Woodstock, NY 12498
  • /49

    $799,999

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,372 Sq Ft

    29 Maurizi Ln, Woodstock, NY 12498

    Set on an almost 3-acre wooded lot, this property has so much to offer in a quiet location close to the Village Green. On the main floor, you have a choice of rooms in which to entertain. A generous foyer leads to a comfortable living room with an actual dining room opposite. Beyond that space, a bright, recently redone, cheery eat-in kitchen awaits. Down the hall, for those cozy nights, a

    Henry Ford Coldwell Banker Village Green

    29 Maurizi Ln, Woodstock, NY 12498
  • /37

    $699,000

    $50K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,991 Sq Ft

    72 Van Dale Rd, Woodstock, NY 12498

    Nestled in a quiet Woodstock neighborhood five minutes from the village center and a short drive from Kingston, The Van Dale offers the privacy of nature without sacrificing convenience. Set on 1.36 acres in a quiet neighborhood, the property is bordered by a private creek that winds through the backyard, creating a peaceful natural setting just minutes from some of the Hudson Valley's most

    Leslie Foti Coldwell Banker Village Green

    72 Van Dale Rd, Woodstock, NY 12498
  • /34

    $539,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,265 Sq Ft

    110 Cottontail Ln, Woodstock, NY 12498

    Tucked away at the end of a quiet cul-de-sac in Woodstock, and set against a backdrop of woods, a gentle stream and mountain views, this well-maintained two-family home offers flexibility and income potential. The main residence features a welcoming living room, an eat-in kitchen, and a convenient half bath on the first floor. Upstairs, three bedrooms and a full bath provide a functional and

    Sally Sprogis Four Seasons Sothebys Intl

    110 Cottontail Ln, Woodstock, NY 12498
  • /13

    $599,000

    • Land
    • 7.18 Acres
    • $83,426 per Acre

    Lot 2 11 Marion's Way, Woodstock, NY 12498

    A once-in-a-generation opportunity to create your dream home in the heart of Woodstock, the coolest small town in America. Nestled on 7 shovel-ready acres just moments from the vibrant village center, this exceptional property offers the perfect balance of privacy, natural beauty, and convenience. Steeped in local history, the land is one of the last remaining vacant parcels from an historic

    Joel Craig Coldwell Banker Village Green

    Lot 2 11 Marion's Way, Woodstock, NY 12498
  • /31

    $599,000

    $160K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    48 Mountain View Ave, Woodstock, NY 12498

    For your client searching for the idyllic cottage on a charming county road, don't overlook Mountain View Ave. This peaceful location is well set back from the road yet walking distance to the center of vibrant Woodstock with all the charming shops, cafes and art galleries and music venues our town is known for.This charming cottage with Craftsman style features was built in 1923. Renovated

    Barbara Ellman BHHS HUDSON VALLEY PROP-WDST

    48 Mountain View Ave, Woodstock, NY 12498
  • /33

    $595,000

    • 2 Beds
    • 2 Baths
    • 1,321 Sq Ft

    419 Sickler Rd, Willow, NY 12495

    Relax, unwind, and take in the views from this charming cottage on one of the most bucolic and peaceful roads in the Woodstock hamlet of Willow--where every day feels like a weekend escape.The tranquility, mountain views, and picturesque valley setting have been cherished by one family for 47 years.Tucked away from the road and nearly invisible to passersby, the property welcomes

    Marcia Weiss Halter Associates Realty

    419 Sickler Rd, Willow, NY 12495
  • /13

    $599,000

    • Land
    • 7.18 Acres
    • $83,426 per Acre

    Lot 2 11 Marions Way, Woodstock, NY 12498

    A once-in-a-generation opportunity to create your dream home in the heart of Woodstock, the coolest small town in America. Nestled on 7 shovel-ready acres just moments from the vibrant village center, this exceptional property offers the perfect balance of privacy, natural beauty, and convenience. Steeped in local history, the land is one of the last remaining vacant parcels from an historic

    Joel Craig Coldwell Banker Village Green

    Lot 2 11 Marions Way, Woodstock, NY 12498
  • /37

    $625,000

    • 3 Beds
    • 1.5 Baths
    • 1,814 Sq Ft

    40 Simmons Dr, Woodstock, NY 12498

    Originally built by the developer of Simmons Drive as his personal home, this spacious Woodstock property offers a rare combination of Village convenience, mountain views, and a peaceful park-like setting.Situated on a quiet no-outlet street, it's just a five-minute stroll to Good Night restaurant, Tinker Street shopping, cafés, galleries, and everything the Village of Woodstock has to

    James Angelakis BHHS HUDSON VALLEY PROP-WDST

    40 Simmons Dr, Woodstock, NY 12498
  • /34

    $799,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,584 Sq Ft

    1 Stone Ridge Ct, Woodstock, NY 12498

    Private Woodstock retreat with a heated in-ground pool, set on 1.21 beautifully landscaped acres located on a quiet cul-de-sac. This spacious 4-bedroom, 2.5-bath home offers 2,584 square feet of versatile living space.The heart of the property is the outdoor space, with a heated 18' x 36' in-ground pool, bluestone patio and mature landscaping creating your own private summer retreat. A

    Susanna Scott-Mitchell Compass Greater NY, LLC

    1 Stone Ridge Ct, Woodstock, NY 12498
  • /91

    $795,000

    • 5 Beds
    • 3 Baths
    • 2,044 Sq Ft

    4868 State Route 212, Willow, NY 12495

    Income Opportunity! This residential property includes a transferable short-term rental license, excellent investment and income-producing potential.Beautifully renovated and thoughtfully updated with numerous high-end upgrades, see below, this versatile 4-5 bedroom, 3-full bath home sits on 3.6 private acres with breathtaking views of Ohayo Mountain, Mount Guardian, Mount Tremper, and

    Ruti kabel Keller Williams Realty HV Nort

    4868 State Route 212, Willow, NY 12495
  • /42

    $749,000

    • 3 Beds
    • 2 Baths
    • 1,553 Sq Ft

    145 Tinker St, Woodstock, NY 12498

    In the heart of Woodstock Village, this beautifully reimagined Colonial offers the rare combination of historic character, modern comfort, and true **walk anywhere convenience**. Set beside Tannery Brook, the home is designed to make the most of its stream side setting, with light-filled interiors, an open-concept layout, and two sets of French doors that create an effortless connection to the

    James Billingsley Halter Associates Realty Inc

    145 Tinker St, Woodstock, NY 12498
  • /24

    $600,000

    • Land
    • 28.17 Acres
    • $21,299 per Acre

    465 Sickler Rd, Willow, NY 12495

    28+ Acres in Woodstock with Views Set at the foot of Mt. Tobias and surrounded by protected state and conservancy land on all sides, this exceptional 28+ acre parcel offers a rare opportunity to build with lasting privacy just minutes from the heart of Woodstock. An established driveway leads to a thoughtfully cleared build site where expansive valley and mountain views create a stunning backdrop

    Leigh Bokser Compass Greater NY, LLC

    465 Sickler Rd, Willow, NY 12495
  • /51

    $730,000

    • 2 Beds
    • 1.5 Baths
    • 1,410 Sq Ft

    15 Lake View Dr, Lake Hill, NY 12448

    15 Lake View Drive | Lake Hill, NYA modern Catskills retreat with thoughtful architecture, natural beauty, and Cooper Lake just across the road.Set on three wooded acres in Lake Hill, this distinctive architect-designed contemporary offers a rare combination of privacy, design, and proximity to the best of the Hudson Valley. Tucked among mature trees and dramatic natural

    Mackenzie Grate The Machree Group, LLC

    15 Lake View Dr, Lake Hill, NY 12448
  • /19

    $799,000

    $60K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,562 Sq Ft

    2323 Glasco Turnpike, Woodstock, NY 12498

    A rare Byrdcliffe Colony offering, this 1911 Woodstock artist home sits just off Lower Byrdcliffe Road on a private half-acre of garden, lawn, patio, and woods. Rich with history and creative spirit, the original structure features the classic north-facing artist's window designed for painter's light, along with original beams and woodwork that speak to the home's early 20th-century

    Mark Kanter BHHS HUDSON VALLEY PROP-WDST

    2323 Glasco Turnpike, Woodstock, NY 12498
  • /33

    $569,000

    $30K PRICE DROP
    • 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
  • /28

    $599,000

    $19K PRICE INCREASE
    • 3 Beds
    • 3 Baths
    • 1,824 Sq Ft

    171 Van Dale Rd, Woodstock, NY 12498

    Step into this meticulously maintained and tastefully updated Woodstock split-level. Set way back from the road on one beautifully landscaped acre, featuring stately mature shade trees, ornamental shrubs, huge rhododendrons and plenty of sun. The interior of the home was just completely repainted including the garage. The main living level has been renovated to create a new, more modern great

    Brian Cafferty Halter Associates Realty

    171 Van Dale Rd, Woodstock, NY 12498
  • /44

    $599,000

    $150K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 2,355 Sq Ft

    11 Nordic Dr, Woodstock, NY 12498

    Welcome to this distinctive Woodstock retreat, a home shaped by the creativity and vision of the artists who have called it their own since 2001. Originally built in 1937, this charming mountaintop home has evolved over the years through thoughtful additions, including an impressive upper-level studio with a separate entrance, plus a vaulted deck overlooking the property's picturesque grounds.

    Lisa Halter HALTER ASSOCIATES REALTY INC

    11 Nordic Dr, Woodstock, NY 12498
  • /42

    $799,900

    $195K PRICE DROP
    • 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

    Dominique Musialkiewicz Howard Hanna Rand Realty

    5 Maverick Terrace, Woodstock, NY 12498
  • /38

    $695,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,067 Sq Ft

    18 Playhouse Ln, Woodstock, NY 12498

    Perfectly situated in the heart of Woodstock Village, this charming move-in-ready single-level country cottage is complemented by a separate permitted studio cottage (STR)--an ideal artist's studio, guest cottage, home office, creative retreat, or potential income-producing opportunity. Together, they offer exceptional flexibility just moments from Woodstock's renowned restaurants, galleries,

    Jeanne Rakowski Corcoran Country Living

    18 Playhouse Ln, Woodstock, NY 12498
  • /91

    $795,000

    • 5 Beds
    • 3 Baths
    • 2,044 Sq Ft

    4868 New York 212, Willow, NY 12495

    Income Opportunity! This property includes a transferable short-term rental license, excellent investment and income-producing potential.Beautifully renovated and thoughtfully updated with numerous high-end upgrades, see below, this versatile 4-5 bedroom, 3-bath home sits on 3.6 private acres with breathtaking views of Ohayo Mountain, Mount Guardian, Mount Tremper, and Panther Mountain.

    Ruti kabel Keller Williams Realty HV Nort

    4868 New York 212, Willow, NY 12495
  • /21

    $595,000

    • 2 Beds
    • 1 Bath
    • 1,338 Sq Ft

    357 Chestnut Hill Rd, Woodstock, NY 12498

    A STORYBOOK WOODSTOCK RETREAT IN THE WOODSSome homes provide shelter; others provide sanctuary. 357 Chestnut Hill Road is a sanctuary in the woods--a soulful Woodstock retreat where sunlight spills through skylights, pine glows underfoot, and the forest seems to lean in and whisper, ''stay awhile.''Set on 1.6 wooded acres with approximately 257 feet of road frontage, this

    Jacob Miles Brown Harris Stevens Hudson

    357 Chestnut Hill Rd, Woodstock, NY 12498

Home Price Trends

Median Sale Price
$720,750
Median Single Family Sale Price
$750,000
Median Townhouse Sale Price
$770,000
Median 2 Bedroom Sale Price
$600,000
Median 1 Bedroom Sale Price
$531,000
Average Price Per Sq Ft
$459
Number of Homes for Sale
22
Last 12 months Home Sales
118
Months of Supply
3.60
Median List Price
$755,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
5%
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