Woodstock, NY Houses for Sale

Tucked away at the end of a long, meandering private drive, this country retreat offers the opportunity to embrace serenity, privacy, and refined rural living. Set on an idyllic 4.4-acre parcel, this residence was designed to harmonize effortlessly with the surrounding woodlands.The home's expansive picture windows and open-concept great room create a seamless flow between indoors and out, making

Joseph Satto Fresh Air Realty

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

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

Nestled along one of the most beautiful, meandering roads in Woodstock, this stunning five-bedroom contemporary ranch offers the perfect blend of modern convenience and serene country living. Set on five gently sloped and landscaped acres adorned with floral gardens, native plants, bluestone walkways, and partial fencing to keep pets in and deer at bay, this home is a true Hudson Valley gem. All

Ellen Osgood Coldwell Banker Village Green

First Time Ever on the Market - A Truly Rare Generational Gem in the Heart of Woodstock!Discover an extraordinary opportunity to own a one-of-a-kind property that blends ultimate privacy with unbeatable proximity. Nestled on nearly 8 private acres just a short walk from the center of Woodstock, this magical estate offers the best of both worlds, serene seclusion and immediate access to everything

Nan Potter Potter Realty

Accepted offer. 5/20/25 Live an Elevated LifePerched high on iconic Overlook Mountain near the end of a private road — just minutes from the heart of Woodstock—this striking Modern contemporary home delivers jaw-dropping, panoramic views that stretch from the Catskills to the Hudson River, including Mohonk and the Ashokan Reservoir. It’s the ultimate mountaintop escape: private, peaceful, and

Lisa Cooper Serhant LLC

Enchanting Woodstock Compound with 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, featuring three distinct

Michelle Bergkamp Corcoran Country Living

Just moments from the heart of Woodstock, this thoughtfully sited property on 1.5 acres offers exceptional privacy and the ease of one-level living. Set back from the road and enveloped by nature, the home exudes a sense of calm from the moment you step through the front door.Built in 1955, this cedar-sided ranch has the subtle mid-century sensibility and sun-drenched interiors. The home feels

Leslie Foti Coldwell Banker Village Green

Architect-Designed Mid-Century Modern Retreat Overlooking a Year-Round Stream!Tucked away at the end of a quiet cul-de-sac and perched high above a meandering year-round stream, this architect-designed mid-century modern home offers the rare combination of total privacy and effortless access to the heart of Woodstock, NY.With its signature California-style high ceilings and clean lines, the

Mark Kanter BHHS HUDSON VALLEY PROP-WDST

Turn key Opportunity - whether you are looking for a full time residence or second home. Often referred to as Zena Cottage by Airbnb guests, this charming home is 3 minutes to the Village of Woodstock, and a short drive to hip uptown Kingston, Rhinebeck and the NYS Thruway. 2 hrs from NYC.Set against a private wooded backdrop, this 1957 home on 1/3 of an acre has a lush lawn, spectacular

Benjamin Armento Coldwell Banker Village Green

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

Spacious, Light-Filled Ranch Minutes from Woodstock .Welcome to your dream retreat just minutes from the heart of Woodstock! This beautifully updated 3-bedroom, 2-bathroom ranch home is tucked away on a quiet cul-de-sac in a peaceful, well-established neighborhood. From the moment you arrive, you'll be charmed by the mature, enclosed front garden and the wooded privacy that surrounds the

Brenda Graf Corcoran Country Living

Perched high on Overlook Mountain just a mile from the heart of Woodstock, this striking contemporary residence—designed and built in 1995 by the iconic Bananas of Woodstock—is a rare architectural gem that seamlessly blends creativity, quality, and comfort.Privately sited among the trees, the home's unique design is constructed with steel beams throughout, cleverly concealed beneath rich wood

Baris Demirel Serhant LLC

Located down private country lane with the Sawkill Creek across lane. Beautiful setting for this two bedroom ranch home that is all cabin feel. Dead end lane with only 5 homes on it. Beautiful location and setting. Easy drive to Woodstock, Hurley and Kingston. Close to Ashokan Reservoir. Just across from entrance to Cottonwood is 60 acre Thorne Preserve with hiking trails. Home and appliances

James Murphy Patty Conti Realty Group LLC

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 four bedrooms (two in the

Casey Kearns Corcoran Country Living

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 features 4

Michelle Bergkamp Corcoran Country Living

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

Sally Sprogis Four Seasons Sothebys Intl

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 approach is unforgettable: a wide

Kathryn Johnson William Pitt Sothebys Int Rlty

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

It's not just about the view! Don't get me wrong, the views are amazing and expansive, and from almost every room. The Ashokan Reservoir, the entire Shawangunk ridge from Mohonk to Sam's Point, Ohayo Mountain and even a bird's eye view of the buildings in the center of town anchored by the old Dutch Church steeple. But this three level designer inspired contemporary has so much more to offer!

Daniel Winn Halter Associates Realty

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

Introducing an exquisite four bedroom two and a half bath Woodstock home that perfectly balances modern updates with timeless charm. Nestled on nearly an acre of land, this beautifully renovated property boasts an abundance of natural light that floods its spacious, high-ceilinged interiors. Step into the heart of the home, where the kitchen dazzles with unique Moroccan tile, creating a stunning

Jeanne Boice Howard Hanna Rand Realty

Tucked away on a private road, this stylish saltbox contemporary offers the perfect blend of modern comfort and natural beauty. Being sold furnished and set on 4.81 acres of lush greenery, rock outcroppings, and abundant wildlife it provides a peaceful retreat just minutes from Woodstock.Designed to embrace the sun-drenched setting, the home features an airy, open floor plan highlighting a

Laurie Ylvisaker Coldwell Banker Village Green

Nestled in the heart of Woodstock, this beautifully remodeled 4-bedroom, 2.5- bathroom home seamlessly blends modern comfort with timeless charms. With an open-concept layout and soaring vaulted ceilings, the home feels both spacious and inviting. Original hardwood floors run throughout, adding warmth and character. The custom-designed kitchen is a chef's dream, featuring brand new cabinetry,

Eliana Amodio Amodio Real Estate & Prop

A One-of-a-Kind Renovated Barn & Creative Haven in WoodstockSet on three peaceful acres with a small stream and meandering mossy paths, this beautifully renovated 1910 barn blends historic charm with modern upgrades. Designed as both a unique home and an inspiring creative space, this property has been meticulously upgraded with radiant heating, all-new insulation, updated electrical and

Baris Demirel Serhant LLC

The perfect Upstate compound. Located in one of the most beautiful locations in Woodstock, this 3 bedroom 2 bath home includes a new 550 square ft guest house for a total of 1973 square feet, an in-ground pool and many recent upgrades and improvements. Just across the way from the Thorne Preserve with its peaceful trails, one can take in nature and glorious mountain views while being only 5

Amy Lonas Coldwell Banker Village Green

WOODSTOCK-Rustic ranch in a convenient location, is available immediately! Open living area has cathedral ceilings, a wall of windows and a nice dining area leading to the deck. There are two nice size bedrooms, one being en-suite, both with walk-in closets. A second full bath is down the hall. The kitchen has an entrance from the dining area or hallway, with plenty of cabinets, including a

Dana Goldberg Houlihan Lawrence-R

Discover modern living at its finest with this newly built contemporary home, perfectly nestled on 2 private acres along the enchanting Sawkill Creek in Woodstock. Designed with both style and practicality in mind, this property seamlessly blends sleek modern amenities with the natural beauty of its surroundings.Built above the floodplain in accordance with FEMA standards, the home offers peace

Jeanne Boice Howard Hanna Rand Realty

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 with

Richard Vizzini Corcoran Country Living

Discover the perfect blend of comfort and opportunity in this charming duplex situated near the heart of Woodstock. This legal two-family home, each unit approximately 900 square feet, offers a unique chance to live in one side while renting out the other, making it an ideal investment property or a cozy haven for extended families.As you approach the property, a separate driveway for each unit

Pieta Williams Halter Associates Realty