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Woodstock, NY Homes for Sale with Pool

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  • /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
  • /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
  • /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
  • /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
  • /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
  • /109

    $6,700,000

    • 3 Beds
    • 6 Baths
    • 2,417 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
  • /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
  • /74

    $2,950,000

    • 3 Beds
    • 3 Baths
    • 2,608 Sq Ft

    235 California Quarry Rd, Woodstock, NY 12498

    Architect-Designed Modern Retreat with Unparalleled Views Over WoodstockPerched high above the town of Woodstock, this rare and exceptional home offers a front-row seat to breathtaking panoramic views that stretch from the mountains to the Ashokan Reservoir. Designed by noted architect Les Walker, this contemporary residence evokes the magic of living in a luxurious treehouse—where every

    Ellen Osgood Coldwell Banker Village Green

    235 California Quarry Rd, Woodstock, NY 12498
  • /25

    $479,500

    • 3 Beds
    • 1 Bath
    • 1,164 Sq Ft

    44 Overlook Dr, Woodstock, NY 12498

    Three bedroom, one bath, 1124 ft.2 in Woodstock. Walking distance to the Bearsville theater formally owned by Bob Dylan's manager, Albert Grossman with music and restaurants. New refrigerator, new dishwasher, stove like new ( three years old). Hot water tank(3 years old) microwave, new carpet, professionally painted inside and out, living room and large multi use room (could be 4th bedroom) not

    Qizhan Yao Realmart Realty, LLC

    44 Overlook Dr, 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
  • /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
$700,000
Median Townhouse Sale Price
$607,500
Average Price Per Sq Ft
$426
Number of Homes for Sale
32
Last 12 months Home Sales
123
Months of Supply
3.10
Median List Price
$749,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
2%
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