19

Woodstock, NY Homes for Sale with Pool

Section Image Section Image
  • /63

    $1,150,000

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    109 the Middle Way, Mount Tremper, NY 12457

    Tucked away on over 7 private acres off a quiet road in coveted Mount Tremper, this striking 2-bedroom, 2.5-bath contemporary offers ultimate seclusion, panoramic mountain views, and the kind of indoor-outdoor living dreams are made of. With soaring windows and a bright open-concept layout, the living room flows effortlessly into the dining area and kitchen, complete with a breakfast bar for

    Agent Photo

    Catherine Quintard

    Compass Greater NY, LLC

    (845) 203-8492

    109 the Middle Way, Mount Tremper, NY 12457
  • /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
  • /50

    $4,999,000

    • 4 Beds
    • 4 Baths
    • 3,899 Sq Ft

    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

    Michelle Bergkamp Corcoran Country Living

    18 Striebel Rd, Woodstock, NY 12498
  • /45

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,080 Sq Ft

    11 Grogkill Rd, Willow, NY 12495

    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 views; all next door to your own country

    Sharon Breslau BHHS Hudson Valley Properties

    11 Grogkill Rd, Willow, NY 12495
  • /47

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,080 Sq Ft

    11 Grog Kill Rd, Willow, NY 12495

    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 (12') 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 views; all next door to your own

    Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

    11 Grog Kill Rd, Willow, NY 12495
  • /53

    $1,695,000

    • 3 Beds
    • 3.5 Baths
    • 3,072 Sq Ft

    253 Upper Byrdcliffe Rd, Woodstock, NY 12498

    Historic Byrdcliffe Estate on One of Woodstock's Most Beloved Roads.Step into a piece of Woodstock's storied past with this enchanting 1910 Arts & Crafts masterpiece, gracefully situated on nearly six bucolic acres along one of the town's most picturesque and sought-after roads.Originally owned by Jane BYRD Whitehead and Ralph RadCLIFFE Whitehead, two of the visionary founders of the

    John Kralik Compass Greater New York, LLC

    253 Upper Byrdcliffe Rd, Woodstock, NY 12498
  • /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

    $1,400,000

    • 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 Fresh Air Realty

    540 Mount Tobias Rd, Mount Tremper, NY 12457
  • /38

    $1,200,000

    • 3 Beds
    • 3.5 Baths
    • 2,337 Sq Ft

    94 the Middle Way, Mount Tremper, NY 12457

    Privately sited on a quiet back road in the Catskills, Noorden House is a modern retreat offering both seclusion and convenience—just 20 minutes to Woodstock, 15 to Phoenicia, and 30 to two ski mountains. Elevated on over 5 acres, the home enjoys distant mountain views, beautifully landscaped grounds, and serene natural features including a heated freeform pool, a small pond, and a picturesque

    Jennifer Grimes Country House Realty Inc

    94 the Middle Way, Mount Tremper, NY 12457
  • /32

    $1,749,900

    • 3 Beds
    • 2.5 Baths
    • 3,076 Sq Ft

    16 Juniper Ln, Woodstock, NY 12498

    Welcome to Juniper Woods. Nestled on four serene acres just minutes from the center of Woodstock, Juniper Woods is a custom-designed, exquisitely renovated residence offering the perfect balance of sophistication, tranquility, and convenience. With over 3,000 square feet of thoughtfully curated living space, this three-bedroom, three-bathroom home is rare, architecturally striking, and deeply

    Victoria Stent Coldwell Banker Village Green

    16 Juniper Ln, Woodstock, NY 12498
  • /40

    $1,395,000

    • 4 Beds
    • 5 Baths
    • 3,100 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, sunlight and bespoke stainglass throughout. The layout is wideopen to your own creativity and all the possibilities youcan conjure up. Permitted as asuccessful year ‘round Airbnb andcurrently configured with

    Jason Karadus Corcoran Country Living

    5 Downer Ln, Woodstock, NY 12498
  • /49

    $525,000

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    296 Maverick Rd, Woodstock, NY 12498

    This private and beautifully sited Woodstock home is set well off the road yet convenient to everything Woodstock and the Hudson Valley have to offer. The sunshine filled living room opens up to a dining area and kitchen plus 3 bedrooms and 1.5 baths all on the main level. A fully finished walk-out lower level offers flexible space with a rec room, laundry room plus an office, bedroom, workout

    Amy Lonas Coldwell Banker Village Green

    296 Maverick Rd, Woodstock, NY 12498
  • /25

    $499,500

    • 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
  • /38

    $899,000

    • 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
  • /56

    $899,000

    • 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
  • /25

    $595,000

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

    58 Baker Rd, Bearsville, NY 12409

    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 a warm and

    Heather Martin United RE Hudson Valley Edge

    58 Baker Rd, Bearsville, NY 12409
  • /42

    $899,000

    • 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
$1,165,000
Median Single Family Sale Price
$1,165,000
Average Price Per Sq Ft
$443
Number of Homes for Sale
4
Last 12 months Home Sales
26
Months of Supply
1.80
Median List Price
$999,750
Median Change From 1st List Price
-17%
Median Home Sale Price YoY Change
41%
How to Buy a Home How to Finance a Home How to Sell a Home