Woodstock NY Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,648
Status:
NEW LISTING
MLS#:
20251397
Type:
Single Family
Lot size:
0.95 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Century 21 Alliance-NP 845-255-6163
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ADDITIONAL INFORMATION

Welcome to this beautifully renovated 3-bedroom, 2-bathroom home located just minutes from the heart of Woodstock. With all-new carpeting throughout, a brand-new kitchen, and fully updated bathrooms, this turn-key property offers effortless comfort and style from the moment you step inside. Cozy up by the fireplace on chilly evenings, or enjoy warm-weather days in the expansive backyard—ideal for relaxing, entertaining, or soaking in the natural surroundings. The recent septic upgrade adds peace of mind, making this home as functional as it is beautiful. Conveniently located on a main road with easy access to the vibrant village of Woodstock, you're also just a short drive to Kingston and about 90 minutes to NYC. Whether you're seeking a full-time residence or a weekend getaway, this move-in ready home delivers style, comfort, and unbeatable proximity to all the best the Hudson Valley has to offer.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,065
Status:
NEW LISTING
MLS#:
863210
Type:
Single Family
Lot size:
0.49 Acres
Year built:
1950
A broker reciprocity listing Courtesy: BHHS Hudson Valley Properties 845-679-0006
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ADDITIONAL INFORMATION

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 cabinetry) making entertaining both inside or outside a snap. The Living Room is oversized and anchored by a large corner fireplace. The rounded red door of this unique cape style home (c.1950) ushers you through an adorable foyer and weather lock. Upstairs is a lovely, large bathroom with a herringbone tile shower/tub enclosure and a swinging glass door. There are also two large bedrooms with ample closets and plenty of room for a desk or in-home office. This is a magical spot that is basically right in town, yet it feels like you are remote. The house is tucked behind 2 other homes separating it from the road, and it backs up to 2 streams and some calming woods. This half acre leaves room for a stream-side fire pit, a garden, a place to play croquet, or a place to relax and lounge in the sun. A full basement with laundry adds to the comfort and storage options. Easy-peasy as you are on the NYC bus line and can jump out right in front of your driveway. Or drive up (under 2 hours from NYC) or your leave a car in the driveway that supports 4 or 5 cars. This is a place to enjoy the many delicious restaurants, shopping, and proximity to hiking, skiing, and everything the Catskills has to offer! Get comfortable in this ''move in and relax'' situation!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,960
Status:
Active
MLS#:
20251318
Type:
Single Family
Lot size:
7.64 Acres
Year built:
1982
A broker reciprocity listing Courtesy: Potter Realty 845-331-0898
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ADDITIONAL INFORMATION

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 this vibrant community has to offer. This architecturally forward home was ahead of its time, built with passive solar principles and energy efficiency in mind. Earth-sheltered northern walls provide natural insulation, while the southern-facing side is bathed in light and warmth from the sun. Designed by a professional chef, the kitchen is a culinary masterpiece. Thoughtfully laid out for efficiency, it features a spacious pantry within arm's reach of your prep space, and a true chef's range with six burners, a flattop griddle, broiler/salamander, and dual ovens, ideal for entertaining. The main level offers a warm, inviting layout including a large living room, formal dining room, and a charming three-season sunroom. The private primary suite includes a luxurious dressing room, a spa-like bath with a soaking tub, and a step-in shower. Ascend the spiral staircase to the upper level, where an expansive family room with gleaming hardwood floors and abundant natural light awaits, complete with its own ground-level exterior access. The east wing of the upper level features two additional bedrooms and a full bath. Step outside to enjoy the full in-ground pool, sweeping lawns, rolling meadows, and lush surrounding woods, offering a true sense of retreat while remaining minutes from town. This is more than a home, it's a legacy property ready to be treasured for generations.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,860
Status:
Active
MLS#:
861663
Type:
Single Family
Lot size:
1.95 Acres
Year built:
2000
A broker reciprocity listing Courtesy: Serhant LLC 646-480-7665
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ADDITIONAL INFORMATION

A head to toe renovation has transformed this home into almost brand new! Big ticket items such as new roof over main part of house, electrical wiring redone and new electric panel box upstairs, updated plumbing as well. This beautifully renovated 4-bedroom, 2.5-bathroom home is set on 2 private acres in a peaceful and highly desirable location just minutes from the villages of Woodstock and Saugerties. Surrounded by trees and tucked back from the road, this move-in-ready home offers both privacy and convenience, with easy access to shopping, dining, outdoor recreation, and the NY Thruway. Step inside to discover a bright, open interior with all-new wood flooring and tiled bathrooms and kitchen. The walls were taken down to the studs, new sheetrock installed and all the rooms were freshly painted. The heart of the home is the sunlit kitchen featuring ceramic tile flooring, ample counter space, and direct access to the dining area and back deck—perfect for indoor-outdoor entertaining. The living and dining rooms are welcoming and spacious, and the separate den features a cozy fireplace, creating the perfect spot to unwind. All bathrooms have been fully updated with new vanities, toilets, and stylish tub and shower installations. The primary suite offers comfort and privacy, while three additional bedrooms provide flexible space for a home office and more people! Other highlights include a covered front porch for enjoying quiet mornings, a 2-car attached garage with interior access, mud room with storage and a practical layout that offers both functionality and flow. With tasteful upgrades throughout and a warm, modern feel, this home is ideal as a full-time residence, weekend getaway, or investment opportunity in one of the Hudson Valley's most sought-after areas.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,944
Status:
Active
MLS#:
855509
Type:
Single Family
Lot size:
0.85 Acres
Year built:
1966
A broker reciprocity listing Courtesy: William Pitt Sothebys Int Rlty 845-677-9822
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ADDITIONAL INFORMATION

Peaceful 4 Bedroom Home Just Minutes From Town - Move in Ready! Welcome to this beautifully updated 4 bedroom, 1.5 bath home in a quiet Woodstock Neighborhood, just minutes to the center of town. Enjoy the best of both worlds: serenity and privacy with a spacious back and front yard and easy access to shops, dining and all the charm that Woodstock has to offer. Inside you will find freshly painted interiors, refinished hardwood floors, new flooring downstairs and a rebuilt sunroom filled with natural light. The living space features a cozy Jotul wood stove, perfect for cold winter nights. The kitchen comes with a new high end stove and refrigerator, plus a new washer and dryer for your convenience. Additional updates include: a renovated back room, rebuilt sunroom, new landscaping and garden, new storm doors, resealed chimney, Navien Combi Boiler with Hot Water on Demand, septic was pumped in 2024 and the home passed a full inspection in 2023. Set on a peaceful street, this home offers a perfect mix of comfort, charm, and functionality. Move-in ready and full of warmth - don't miss this Woodstock Gem!

Open House:

Saturday, 5/24 11:00-1:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,928
Status:
Active
MLS#:
856159
Type:
Single Family
Lot size:
0.41 Acres
Year built:
1959
A broker reciprocity listing Courtesy: Corcoran Country Living 845-338-5832
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ADDITIONAL INFORMATION

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 property—offering a rare blend of tranquility and convenience. Step inside to a bright, open-concept interior where natural light floods the space, highlighting gleaming hardwood floors and thoughtful modern touches throughout. The stylish kitchen features updated finishes and flows seamlessly into the dining and living areas, creating the perfect setting for both daily life and effortless entertaining. A large room with soaring cathedral ceilings at the back of the home offers incredible versatility—ideal for a home office, creative studio, guest suite, or playroom. Outside, unwind on the spacious deck and enjoy peaceful views framed by mature trees—perfect for morning coffee, weekend gatherings, or quiet evenings under the stars. Cozy up by the sleek Scandinavian gas stove in the living room, enhanced by energy-efficient skylights that add both charm and warmth. Additional highlights include a two-car garage, generous closet space, whole house generator and two sheds for all your storage needs. Recent updates ensure move-in-ready ease, including new siding, hot/cold mini-splits, a high-efficiency boiler, a 500-gallon propane tank, and select appliances. Best of all, this home is just minutes from the Woodstock Village Green, Bearsville, and the beloved Sunfrost Market—placing you close to the best of local culture, shopping, and dining. This is more than a home—it's a lifestyle. Privacy, comfort, and convenience come together in this light-filled sanctuary. Don't miss your chance to make it yours!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,210
Status:
Active
MLS#:
853797
Type:
Single Family
Lot size:
3 Acres
Year built:
1995
A broker reciprocity listing Courtesy: Serhant LLC 646-480-7665
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ADDITIONAL INFORMATION

Accepted offer. 5/20/25 Live an Elevated Life Perched 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 designed for unforgettable entertaining. Designed by a California architect with a love of Mid-Century Modern styling, the home showcases signature Mid-Century elements—organic materials, and a strong connection to nature. A showstopping great room is wrapped in walls of glass that frame the ever-changing sky. The open-concept kitchen flows effortlessly into this lofty space and out to expansive decks, inviting you—and your guests—to linger over morning coffee or sunset cocktails with a view that never quits.

Open House:

Sunday, 5/25 12:00-3:00PM

More Open House Info >

Beds:
2
Baths:
1.00
Sq.Ft.:
704
Status:
Active
MLS#:
20251227
Type:
Single Family
Lot size:
1.01 Acres
Year built:
1966
A broker reciprocity listing Courtesy: Patty Conti Realty Group LLC 845-340-4480
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ADDITIONAL INFORMATION

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 being sold as is. Home now in trust/estate but owned since 1978. Rare opportunity to own a property like this and create your own paradise.. Property located in flood zone.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,868
Status:
Active
MLS#:
20251219
Type:
Single Family
Lot size:
1.52 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Coldwell Banker Village Green 845-679-2255
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ADDITIONAL INFORMATION

Welcome to the Woodstock Retreat House. This exceptional multi-residential compound has been thoughtfully renovated to the highest standards and is fully furnished with a curated mix of vintage and contemporary pieces. A proven high-volume income producer, the property offers flexibility as a primary residence, part-time escape, or short-term rental investment. Set on 1.5 lush, park-like acres, the property comprises a charming one-bedroom, one-bath farmhouse; a stylish one-bedroom studio with a bathroom and kitchenette; a versatile shed with potential for additional guest accommodations; a raised-bed garden; a yoga platform; and a fire pit. The ornately carved wood entry door sets a welcoming tone from the moment you arrive, opening to a mudroom with bluestone tile floors. The farmhouse living space is rich with classic details—wide board floors, beamed ceilings, and farmhouse charm throughout. The renovated kitchen features custom shelving, drawer cabinetry, Cle tile, and Caesarstone countertops and opens to a deck ideal for al fresco dining. A spacious first-floor bath offers a deep soaking tub, laundry area, and thoughtful finishes. Upstairs, the primary suite feels like a private loft retreat filled with natural light. The studio offers a sleek, modern contrast, with polished concrete floors, Cle tile, custom built-ins, and an airy living area with sliders leading to a private patio and wood-fired cedar hot tub. A separate bedroom boasts an oversized en-suite bath with a walk-in shower and custom vanity. The property also includes a shed that could be reimagined as a creative studio or guest space, beautifully landscaped gardens, a yoga platform, and a fire pit—perfect for gathering under the stars. With extensive upgrades throughout, the Woodstock Retreat House balances original character with modern comforts. Enjoy the outdoor wood-fired sauna and the unbeatable location: walk to one of Woodstock's best restaurants and a soon-to-open general store, or take a short drive to the centers of Woodstock, Saugerties, or Kingston. With a Woodstock address yet falling within the Town of Saugerties municipality, this property offers the rare ability to serve multiple purposes—live, rent, or retreat. A complete list of improvements is available upon request. Don't miss the chance to make this private, thoughtfully curated Woodstock retreat your own.

Beds:
3
Baths:
1.00
Sq.Ft.:
894
Status:
Active
MLS#:
20251213
Type:
Single Family
Subdivision:
Other
Lot size:
0.22 Acres
Year built:
1954
A broker reciprocity listing Courtesy: Halter Associates Realty 845-679-2010
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ADDITIONAL INFORMATION

Charming 3-Bedroom Ranch in Prime Woodstock Location! 30 Dixon Ave in Woodstock is a sunny, well-maintained 3 bedroom, 1 bath ranch that sits on a quiet street just minutes from the heart of Woodstock. With single level living and community rich location, it offers a rare opportunity to own a home in this special part of the Hudson Valley. Sold As Is the home retains much of its original charm but has been thoughtfully updated with key improvements, including upgraded electric and plumbing, septic, renovated bathroom and freshened up kitchen for comfortable and move-in ready living. The large fenced backyard features mature trees and blooming perennial gardens, perfect for relaxing, gardening, or entertaining. It's just waiting for its next owners unique vision. The location is a standout. Across the street lies a wide open field above the protected Woodstock Reservoir. Just beyond is a local playground, and the new Woodstock Library is nearing completion at the other end of the street. You're also within short distance to the Bearsville Theater complex, restaurants, the post office, and other local favorites. An ideal full-time home, weekend retreat, or investment opportunity in a peaceful, convenient to everything neighborhood with lasting value.

Beds:
3
Baths:
5.00
Sq.Ft.:
2,896
Status:
Active
MLS#:
857832
Type:
Single Family
Lot size:
3.92 Acres
Year built:
1995
A broker reciprocity listing Courtesy: Serhant LLC 646-480-7665
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ADDITIONAL INFORMATION

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 caps. Walls of south-facing Pella windows flood the space with natural light year-round, offering passive solar warmth in winter and breathtaking views—extending all the way to the Ashokan Reservoir and even Mohonk in the distance. Warm cherry and oak floors run throughout, adding an organic elegance to the home's modern design. The current owners have lovingly enhanced the property over 25+ years with thoughtfully designed additions. A spacious two-car heated garage with a workshop and large storage closet was added, along with a fully equipped art studio featuring plumbing, A/C, and its own private deck and a full basement. In 2012, the home was expanded to include a stunning modern chef's kitchen with concrete and marble countertops and custom cabinetry, a large open dining room with built-ins, and a screened-in porch with an outdoor TV. Just beyond, you'll find a beautifully crafted stone barbecue area for al fresco entertaining. The primary suite features a spa-like bath renovated with a soaking tub, separate steam shower, and Toto Washlet. A second upstairs bedroom—currently used as a library—along with a half bath, was thoughtfully created from existing open space. Connected by an enclosed breezeway that doubles as a dramatic entry foyer, the guest wing offers its own private entrance and includes a living room, bedroom, and full bath—ideal for guests or a private work-from-home retreat. Or convert this to the primary suite for easy ground floor living. In addition, the guest wing has its own basement used for wine storage. A gorgeous 42-foot heated saline gunite pool, surrounded by expansive Brazilian hardwood decking, is complemented by a chic pool cabana, creating the perfect setting for summer gatherings and relaxation. Custom designed metal railings extend from interior curved stairway to the exterior patio and path leading to the pool below. Lush grasses and plantings enhance this mountain oasis. This iconic property is a one-of-a-kind offering that captures the spirit of Woodstock with modern luxury and architectural distinction. Nothing compares to this.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,100
Status:
Active
MLS#:
858172
Type:
Single Family
Lot size:
5.85 Acres
Year built:
2020
A broker reciprocity listing Courtesy: Corcoran Country Living 845-338-5832
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ADDITIONAL INFORMATION

Buckle up! 5 Downer Lane may be the most interesting property you see all year! This 19th century hand-hewn barn-to-house conversion has 35 foot ceilings, sunlight and bespoke stain glass throughout. The layout is wide open to your own creativity and all the possibilities you can conjure up. Permitted as a successful year ‘round Airbnb and currently configured with three bedrooms (two in the turret!) and two additional sleeping areas, it has FIVE designer bathrooms, a grand living/ dining space - with a fireplace and the chandelier of your dreams. This magical abode should not be missed, if fun and FABULOUS are what you are looking for! With bluestone kitchen including Eisenhower pink retro-style appliances by Big Chill, and a screening room for 20 people, this home at more than 3100 square feet offers plenty of space to dream! A cabana with 2nd kitchen opens onto a huge circular deck over 3000 sq ft with complete southern exposure. It completely surrounds the heated pool and hot tub with a view of the mountains and plenty of sky. The 5.85 acres offers up additional amenities, such as a dry sauna, custom-built tiny house, and a separate gym complete with electricity and matted floors. Dream BIG and make this classic Woodstock retreat all yours. A PERFECT reason to call the Hudson Valley, HOME.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,899
Status:
Active
MLS#:
849335
Type:
Single Family
Lot size:
71.69 Acres
Year built:
1914
A broker reciprocity listing Courtesy: William Pitt Sothebys Int Rlty 845-677-9822
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ADDITIONAL INFORMATION

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 bedrooms, 2 full baths, and 2 half baths, with rich period details throughout—including original carved woodwork, wide-plank floors, historic fireplaces, and Dutch doors that enhance both charm and function. One of the home's standout features is the spacious and inviting living area with brick flooring, original bluestone walls, and a dramatic wood-burning fireplace—perfect for cozy evenings or sophisticated entertaining. A gracious covered front porch offers a peaceful place to take in the natural landscape, while a deep soaking tub and light-filled meditation/yoga room provide quiet spaces for rest and renewal. In the 1920s and '30s, the home was owned by famed cartoonist John Striebel, creator of the Dixie Dugan comic strip. Over the years, its walls have echoed with the voices of Bob Dylan, Janis Joplin, Allen Ginsberg, George Harrison, and many other cultural legends. A true cornerstone of Woodstock's creative legacy, the estate was once owned by Albert Grossman, legendary music manager and founder of Bearsville Records and Studios. It was here, in 1965, that the iconic album cover for Bringing It All Back Home was photographed, capturing Bob Dylan and Sally Grossman in the home's elegant living room. Later, the home welcomed talents ranging from Johnny Cash and William Kennedy to Bjork and the Dave Matthews Band. Viking Hall, next door to the main house, offers an exceptional space designed to inspire. This stunning building features a bright and open studio area, ideal for artists, musicians, wellness practitioners, or remote work. With hand-hewn beams, loft space, French doors, and spa-like amenities—including a sauna, steam shower, and soaking tub—the space combines rustic elegance with modern comfort, perfect for creative retreats, workshops, or wellness sessions. Beyond Viking Hall, a private apartment with a stone fireplace, bedroom, and full bath once served as Albert Grossman's personal retreat, where he ran Bearsville Records. His legendary vinyl collection remains, and the lower level offers a gym area with ample storage. The estate includes the Farmhouse at Speare Road, a recently updated 4-bedroom, 2-bathroom residence. With its own private setting, this charming home is well-suited for guests, caretakers, or multi-generational living—offering flexibility for a variety of lifestyle needs. In the surrounding woods, discover a charming cabin complete with a bedroom, bathroom, and cozy kitchen. This private hideaway is ideal for long-term guests, studio rentals, or a secluded creative workspace. Both ready for a variety of uses, a spacious workshop building offers room for artistic or hands-on pursuits, while a classic barn adds rustic charm and versatile storage or studio space. Gardening enthusiasts will appreciate the sun-filled greenhouse, designed for year-round cultivation. A meditation gazebo—ideal for yoga, writing, or reflection in nature and an amphitheater complete with electricity, seating, and platform are among the estate's many distinctive features. Outdoor amenities include a heated, saline gunite pool, garden areas, spring-fed pond, seasonal mountain views, and woodland trails that offer total immersion in the natural beauty of the Catskills. This iconic Woodstock estate is two hours from NYC and in close proximity to the area's most beloved destinations. Whether inspired by its profound cultural roots or artisanal architecture, this property is a once-in-a-generation opportunity. This property is co-listed with Michelle Bergkamp, Corcoran Country Living.

Beds:
2
Baths:
2.00
Sq.Ft.:
900
Status:
Active
MLS#:
20251195
Type:
Single Family
Lot size:
0.2 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 914-238-0676
View additional info

ADDITIONAL INFORMATION

Discover the perfect blend of historic charm and modern luxury in this meticulously renovated 1900 carriage house. This exquisite home features 2 bedrooms and 2 bathrooms, offering a harmonious balance of classic elegance and contemporary convenience. Step into the brand new kitchen, equipped with state of the art Bosch appliances and custom cabinetry from Transformad.com, features a high-tech, anti-fingerprint, impact and scratch-resistant, auto-regenerative, super matt lacquered finish. The kitchen is further enhanced by quartz countertops and solid walnut and steel open shelves, and an ample high gloss lacquered pantry, creating a space that is both functional and visually stunning. Enjoy the tranquility of the new screened-in porch, featuring bronze screens, exquisite carpentry, and elegant French doors. The bathrooms have been transformed with European tiles, custom artisan quality installations, Kohler Purist fixtures, and cedar plank ceilings, providing a luxurious retreat within your home. Throughout the home, you'll find reclaimed Oak floors from the original structure upstairs and new Oak floors downstairs, maintaining the home's historical integrity. A Le Feu Bioethanol Fireplace adds warmth and ambiance, while thoughtfully sourced vintage and modern lighting fixtures illuminate the space beautifully. Energy efficiency is prioritized with an Asko washer and dryer, Pella windows and doors, and a central air and heat system powered by an energy-efficient Mitsubishi heat pump. The entire home is insulated with spray foam and mineral wool, ensuring comfort year-round. All new plumbing and electrical systems have been installed, and the crawl space features a Clean Space System for added peace of mind. Outside features a new Bluestone and brick walkway. Step across the west branch of the Tannery Brook to your renovated garage, which retains some of its original details, preserving its unique character. This carriage house is a testament to thoughtful design and quality craftsmanship, offering a rare opportunity to own a piece of history with all the conveniences of modern living. Nestled in the heart of Woodstock, this prime location offers not only the charm of a historic carriage house but also the serenity of nature. A beautiful stream meanders through the property, providing a tranquil backdrop to your daily life. Enjoy mountain views, while in the center of town, that enhance the picturesque setting, making this home a true sanctuary in one of the most sought-after areas. Whether you're relaxing on the screened-in porch or exploring the vibrant local community, this property offers a unique blend of natural beauty and convenient access to all that Woodstock has to offer. Listing agent is also the owner.

Beds:
4
Baths:
5.00
Sq.Ft.:
2,980
Status:
Active
MLS#:
20251193
Type:
Single Family
Lot size:
0.25 Acres
Year built:
1875
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 914-238-0676
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ADDITIONAL INFORMATION

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 rich heritage and modern versatility, situated on a coveted .25-acre parcel at the vibrant Village Green— the epicenter of town life. Property Highlights: Historic Charm & Modern Convenience: This property offers 8 convenient parking spaces, setting the stage for both residential and commercial possibilities. A charming barn at the end of the parking lot offers additional storage or an opportunity to create something new. Mixed-Use Flexibility: Ideal for savvy investors or visionary homeowners, the property is currently configured with two commercial tenants whose shops face the bustling Village Green, ensuring a steady income stream. Creative Ground Floor Studio: The ground level features radiant heated cement floors and a full bathroom, previously an artist's studio, perfect for creative explorations or versatile living adaptations. Operable Bed and Breakfast: The second floor operates as a licensed Bed and Breakfast, with two elegantly appointed bedrooms, each with its en suite bathroom, alongside a cozy living room, and a well-equipped kitchen and dining area. The license can seamlessly transfer to the new owner, offering immediate business potential. Private Owner's Haven: The top floor is a serene one-bedroom apartment, offering a private retreat with all the comforts of home. Endless Possibilities: Whether you envision converting this historic structure into a grand single-family residence, maintaining its current mixed-use appeal, or purely maximizing its investment potential, the possibilities are truly extensive. Unbeatable Location: Situated in the heart of Woodstock on the Village Green, local shops, galleries, dining, and cultural landmarks are all around. Plus, the convenience of the NY bus stop right outside your door ensures easy access to and from the city. Property Condition: The property is being sold as is, presenting an incredible opportunity to bring your architect and explore all the creative potential this space has to offer. Don't miss this chance to own a piece of Woodstock's storied past with limitless future possibilities. Schedule your tour today and explore the potential of this exceptional property!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,500
Status:
Active
MLS#:
856482
Type:
Single Family
Lot size:
0.39 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Four Seasons Sothebys Intl 845-684-0084
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ADDITIONAL INFORMATION

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 heritage and adding timeless appeal. The main level features a formal dining room that flows effortlessly from the kitchen and living room—an ideal layout for both everyday living and entertaining. A convenient half bath completes the first floor. Upstairs, you'll find three bedrooms—including one with a walk-in closet—along with a full bath. An attic offers additional flexible space, ideal for a studio, office, or creative retreat, especially fitting in this art-inspired community. Outdoor living is equally inviting, with a welcoming front porch, a landscaped level yard, an enclosed back porch, and a practical mudroom entry. The detached garage adds versatility for use as a workshop or additional storage space. Located just a stone's throw from Woodstock's vibrant cultural scene and the iconic Byrdcliffe Art Colony, this restored gem offers a rare opportunity to live where creativity, history, and modern comfort converge.

Beds:
3
Baths:
1.50
Sq.Ft.:
1,568
Status:
Active
MLS#:
20251094
Type:
Single Family
Subdivision:
Other
Lot size:
0.92 Acres
Year built:
1964
A broker reciprocity listing Courtesy: Coldwell Banker Village Green 845-679-2255
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ADDITIONAL INFORMATION

Situated on a generous lot in a fantastic location close to schools, shopping, restaurants, and easy commuting routes, this home is a rare find with tons of potential. A true diamond in the rough, this 1964 ranch home is just waiting for some cosmetic creativity to bring it to life. Step inside to discover a spacious, functional layout featuring a large living area, original hardwood floors, 3 bedrooms and 1.5 baths and an inviting kitchen that opens to a large backyard deck perfect for morning coffee or evening barbecues. The bedrooms are generously sized, and there's plenty of storage throughout. The full basement provides ample extra storage, workshop areas and the potential to expand your living space. The .92 acre lot is set off the road with a yard in front and a beautiful tree lined back yard. There is a fenced in area for pets or a garden. Come explore this classic home that is brimming with possibilities!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,498
Status:
Active
MLS#:
20251087
Type:
Single Family
Lot size:
2 Acres
Year built:
1922
A broker reciprocity listing Courtesy: Win Morrison Realty - W 845-679-9444
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ADDITIONAL INFORMATION

In the heart of the storied Byrdcliffe Colony, you will find this classic Woodstock retreat. Cited perfectly on 2 landscaped acres, featuring flowering trees , fruit trees and a variety of seasonal blooms. Just one mile from the center of town and everything Woodstock has to offer. Four bedrooms and 2 Full baths provide room and comfort for family and friends. Heated and plumbed outbuildings are options for additional living or studio spaces

Beds:
4
Baths:
2.00
Sq.Ft.:
1,923
Status:
Active
MLS#:
853456
Type:
Single Family
Lot size:
3.69 Acres
Year built:
1976
A broker reciprocity listing Courtesy: Corcoran Country Living 845-338-5832
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ADDITIONAL INFORMATION

Experience the Best of Upstate Living in the Heart of Woodstock Discover this enchanting four-bedroom, two-bathroom home located on one of Woodstock’s most sought-after streets. Privately set back from the road and directly across from the storied Thorne Preserve, with its scenic trails and sweeping views of Overlook Mountain, this turnkey residence offers both privacy and direct access to nature. All of this while being just minutes from the vibrant energy of Tinker Street, known for its eclectic restaurants, charming shops, and legendary music venues. Step into your own private backyard oasis featuring lush gardens, a luxurious pool, a hot tub, and an outdoor shower. It is a perfect setting for entertaining or simply unwinding under the stars. Inside, the home is filled with natural light and anchored by rich dark oak hardwood floors. The modern kitchen includes stainless steel appliances and a sleek new induction cooktop, while the recently renovated bathrooms provide a spa-like retreat. Two wood-burning stoves bring warmth and timeless charm to the living spaces. Thoughtful updates include a brand-new roof completed in 2024 and a whole-house Generac generator that ensures comfort and reliability no matter the season. A finished garage offers a versatile space that can serve as a home office or creative studio. Enjoy a peaceful setting without sacrificing convenience. This location offers quick access to all that Woodstock has to offer, a short drive to Uptown Kingston, and less than two hours from New York City. Whether you are seeking a weekend escape or a full-time residence, this exceptional property brings together modern comfort and natural beauty in a rare opportunity to own a piece of Woodstock’s unique charm.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,430
Status:
Active
MLS#:
849213
Type:
Single Family
Lot size:
4.09 Acres
Year built:
2017
A broker reciprocity listing Courtesy: Redfin Real Estate 631-337-8238
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ADDITIONAL INFORMATION

Welcome to 220 John Joy Road, a meticulously maintained and thoughtfully upgraded home tucked away in the heart of Woodstock, NY. Featuring three spacious bedrooms and two and a half baths, this property combines modern amenities with timeless charm, offering a rare opportunity to live comfortably and securely in one of the Hudson Valley’s most beloved areas. Built with concrete walls for superior insulation and airtight living, the home includes an advanced air filtration system and is prepped for a radon mitigation system—only a fan needs to be installed. A full house generator ensures peace of mind in every season, and an extensive alarm system, including alarmed window screens, adds an extra layer of security. Inside, the open and inviting floor plan is highlighted by recessed lighting, a cozy gas fireplace, and thoughtful design touches throughout. The first floor features a versatile office space and a private bedroom with an ensuite bath, offering convenient one-level living options. An attached garage provides easy access and additional storage. The fenced backyard is a private oasis, perfect for entertaining or relaxation, with a lovely patio area and professionally installed landscaping and hardscaping. The irrigation system makes it easy to maintain the lush grounds, keeping them vibrant year-round. The home's basement offers a unique finished flooring design and completed closet installations, providing even more functional living space. Upstairs, the additional shower has never been used but has been carefully maintained. From the welcoming wrap-around porch to the home's solid, efficient construction, every detail here was designed for comfort, beauty, and security. Whether you're seeking a peaceful weekend getaway or a full-time residence, 220 John Joy Road offers the perfect balance of serenity, modern upgrades, and natural beauty, all just minutes from Woodstock’s vibrant shops, dining, and outdoor adventures.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,266
Status:
Active
MLS#:
853306
Type:
Single Family
Lot size:
0.23 Acres
Year built:
1961
A broker reciprocity listing Courtesy: Halter Associates Realty Inc 845-679-2010
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ADDITIONAL INFORMATION

Create Your Dream Home in Woodstock - Perfect for DIY Enthusiasts! Embrace the opportunity to finish this one-level, 3-bedroom home in the heart of Woodstock. With renovations already underway, this property is ideal for hands-on buyers ready to bring their vision to life. The flexible extra room offers endless possibilities—finish it out for additional living space, convert it back into a garage, or transform it into a studio, home office, gym, or guest room. Enjoy the outdoors in comfort from the screened-in back porch—perfect for relaxing, dining, or entertaining while overlooking the backyard. The spacious yard also features two large storage sheds that convey with the property, offering plenty of room for tools, equipment, or creative endeavors. Recent updates include: brand new roof and gutters, new exterior wood siding, upgraded 200 amp electrical panel, new underlayment, new baseboard heaters in the living room and bathroom, 3 new picture windows in front of the house, plus many more. Located in a quiet, charming neighborhood just a short walk to the Bearsville complex and only minutes from Woodstock Village, this home offers proximity to the natural beauty of the Catskills and the vibrant culture of the Mid-Hudson Valley. Due to the nature of the renovations in progress, this property is being sold strictly AS-IS. Bring your imagination and make this unique home your own!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,948
Status:
Active
MLS#:
20251053
Type:
Single Family
Lot size:
2.17 Acres
Year built:
1977
A broker reciprocity listing Courtesy: Coldwell Banker Village Green 845-679-2255
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ADDITIONAL INFORMATION

Highwoods Haven rests on just over two whisper-quiet acres where sunlight filters through tall hardwoods and birdsong fills the air. Although the setting feels miles from anywhere, the property lies barely five minutes from Woodstock's Village Green and within a short, scenic drive of Kingston and Saugerties. A comprehensive 2021 renovation infused the four-bedroom, two-bath residence with modern comfort while preserving its artistic soul. Former owner and Woodstock author Helen Weaver once welcomed Jack Kerouac, Allen Ginsberg, and other luminaries beneath this very roof. Step through the front door and an airy great room unfolds - chef's kitchen, dining area, and living space flowing together beneath vaulted ceilings. Four glass sliders invite daylight to wander inside, then open wide to an expansive wrap-around deck and a deep screened porch. Mornings begin with coffee among the treetops, afternoons drift into alfresco lunches in summer shade, and evenings conclude with cocktails under a sky alive with stars. Inside, rich oak floors and understated finishes lend warmth without distraction, allowing the surrounding landscape to remain the home's quiet centerpiece. The bi-level layout is thoughtfully conceived for flexibility and privacy. Upstairs, a generous primary suite accommodates a king bed; one enjoys the romance of a wood-burning fireplace that casts a golden glow on winter evenings. A spa-style bath, finished in polished stone and brushed brass, serves this level with a deep soaking tub that invites an unhurried exhale. On the main floor, two additional bedrooms offer space for guests or a dedicated office, sharing a crisp, contemporary bath that echoes the home's calm aesthetic. Downstairs, a second living area gathers friends around a vintage cast-iron stove whose gentle heat amplifies the invitation to linger over movies or board games when snow drifts beyond the windows. There is a second primary suite bedroom with a bath, allowing guests to choose which floor to rest on. Comfort is engineered into every detail: a high-efficiency heat-pump system installed in 2023 provides room-by-room climate control; a brand-new well delivers excellent pressure; and smart-home technology allows you to adjust temperature or lighting from anywhere in the world. Life at Highwoods Haven extends well beyond its walls. Three minutes down the lane, members-only Zena Recreation Club offers a pool, tennis courts, and year-round community events. Trailheads leading to hidden waterfalls, glass-clear swimming holes, and protected nature preserves lace the surrounding hills. At the same time, farm-to-table restaurants, galleries, and live-music venues sustain Woodstock's legendary creative heartbeat. Rhinecliff Amtrak lies twenty minutes away, placing New York City less than two hours from your front door. In a region celebrated for its harmony of culture and wilderness, Highwoods Haven stands apartprivate yet convenient, historic yet turnkey, effortless yet inspiring. It is a home designed not merely to be occupied, but to be experienced, savored, and remembered.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,077
Status:
Active
MLS#:
846083
Type:
Single Family
Lot size:
2.2 Acres
Year built:
1989
A broker reciprocity listing Courtesy: William Pitt Sothebys Int Rlty 845-677-9822
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ADDITIONAL INFORMATION

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 rocking-chair front porch stretches across the front of the house, welcoming slow mornings, sunset conversations, and everything in between. The sun-drenched front yard offers endless potential—from garden parties and outdoor games (especially for your furry friends ball chasing delight!) to quiet, contemplative afternoons under the sky. Inside, the home offers over 2,000+ square feet of well-planned living space, filled with natural light and warm, easy elegance. Plenty of room for visiting family and friends, with 3 bedrooms and 2 full baths upstairs and wonderful places to be both all together and to enjoy their own quiet time, that include a gorgeous skylit sun room, a family room for cozy evenings by the fireplace, a sitting room and a formal dining room. The generous eat-in kitchen which opens to a large entertaining deck—is perfect for summer BBQs or al fresco dinners under the stars. From there, step down into the backyard framed by stone walls and old-growth trees for added seclusion. The attached garage provides both convenience and practicality, with ample storage and direct entry into the home. Every element of the property has been thoughtfully considered, from the layout that encourages connection with nature, to the placement of the home that ensures a sense of peaceful remove—without sacrificing access to daily essentials. A large sized shed with AC and power has been used by the current owner as a recording studio, and the unfinished full basement with it high ceilings, abundant storage space and dance floor, are both open to be whatever suits your needs or your imagination desires... Whether you’re seeking a full-time residence or a weekend refuge, this is a home where tranquility meets possibility. Walking distance to the wonderful Woodstock Day school, less than 10 minutes to the town of Woodstock and 1 hour and 45 minutes to Manhattan

Beds:
4
Baths:
3.00
Sq.Ft.:
2,320
Status:
Active
MLS#:
850015
Type:
Single Family
Lot size:
1.34 Acres
Year built:
1972
A broker reciprocity listing Courtesy: Serhant LLC 646-480-7665
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ADDITIONAL INFORMATION

Searching for the perfect blend of style, comfort, and convenience? It's here! This remarkable contemporary in one of Woodstock's most sought-after neighborhoods is ready to welcome you home. Set on a spacious and private 1.34-acre lot, this beautifully maintained four-bedroom, 2.5-bath residence offers a seamless mix of modern updates and inviting charm. The heart of the home is the stunning renovated kitchen, featuring stainless steel appliances, and a oversized islandâ€''perfect for cooking, gathering, and entertaining. The open living room/dining room kitchen provides a gracious space for entertaining and relaxing. A gas fireplace with stone mantel and built in display cupboards above is a central focal point in the living room. Three of the bedrooms are down the hallway with an added flex room for office or den. Downstairs is another large living room with gas fireplace and additional bedroom and 1/2 bathroom. A tidy utilitarian laundry room has recently been renovated. There is an extra refrigerator in there. The drive under garage is where the utilities are housed and electric vehicle charger has been installed. Don't miss this opportunity to own a move-in-ready home in a prime location - a short drive to the center of Woodstock, Hannefords grocery store and Route 28 corridor to Kingston and points west.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,300
Status:
Active
MLS#:
849001
Type:
Single Family
Year built:
1983
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 516-677-0030
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ADDITIONAL INFORMATION

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 Next To The Wood Burning Stove! The Perfect Home For Retreat Or Year Round Use. Great Opportunity For Those Looking To Host A Vacation Rental. A Must See!, Additional information: Appearance:Diamond

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS. Real estate listings held by brokerage firms other than Xome are marked with IDX logo and the detailed information about them includes the name of the listing broker. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025 by the Hudson Valley Catskill Region MLS and Ulster County Board of Realtors, Inc. All Rights Reserved.

Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025, OneKey MLS, Inc. All Rights Reserved.



Woodstock Real Estate

Woodstock is located in New York. Woodstock, New York has a population of 6,215. Woodstock is less family-centric than the surrounding county with 20.17% of the households containing married families with children. The county average for households married with children is 25.39%.

The median household income in Woodstock, New York is $66,181. The median household income for the surrounding county is $71,040 compared to the national median of $69,021. The median age of people living in Woodstock is 60.2 years.

Woodstock Weather

The average high temperature in July is 83 degrees, with an average low temperature in January of 12.3 degrees. The average rainfall is approximately 48.2 inches per year, with 51.1 inches of snow per year.

Woodstock Map

Woodstock Real Estate Market Conditions

  • Median sales price

    $953,700
    24.5%
    change since last quarter
  • # Active listings

    48
    30-day change

Woodstock Schools and Demographics

Education near Woodstock, NY

City County
High School Graduates 96.67 91.42
College Degree - 2 year 6.79 10.4
College Degree - 4 year 60.31 34.48
Graduate Degree 19.92 11.78
Expenditures per Student 30,766 30,766
Students per Teacher 11.2 11.2

Elementary Schools near Woodstock, NY

Grades Students P/T Ratio ZIP
Cahill School KG - 06 358 15.1 12477
E R Crosby Elementary School KG - 04 346 14.2 12449
Ernest C MYER School KG - 04 204 13.7 12443
Morse School KG - 06 338 15.8 12477
Mount Marion Elementary School KG - 06 310 13.5 12477
Riccardi Elementary School KG - 06 298 13.8 12432
Woodstock Elementary School KG - 03 244 11.9 12498

Middle Schools near Woodstock, NY

Grades Students P/T Ratio ZIP
M Clifford Miller Middle School 05 - 08 878 11.9 12449
Saugerties Junior High School 07 - 08 421 16.4 12477

High Schools near Woodstock, NY

Grades Students P/T Ratio ZIP
Saugerties Senior High School 09 - 12 925 19.2 12477

Demographics near Woodstock, NY

City County
Neighborhood Type Small town
Population 6,215 181,862
Population Density 92 162
Median Age 60.2 44.2
People per Household 1.9 2.4
Median Household Income 66,181 71,040
Average Income per Capita 61,299 38,966

Real estate near Woodstock