Homes for Sale near Woodstock Day School

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  /35

  $749,000

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft

  1637 Glasco Turnpike, Woodstock, NY 12498

  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,

  Leslie Foti Coldwell Banker Village Green

  1637 Glasco Turnpike, Woodstock, NY 12498
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  /32

  $399,500

  • 4 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  43 Brittany Dr, West Hurley, NY 12491

  Classic Colonial Charm in Prime LocationFirst time on the market in decades. This lovingly maintained and stately Colonial sits on over half an acre just minutes to the heart of the Village of Woodstock. A perfect blend of tranquility and convenience.From the moment you arrive the curb appeal is apparent, with its expansive front lawn, mature trees and its timeless architecture.

  Marcia Weiss Halter Associates Realty

  43 Brittany Dr, West Hurley, NY 12491
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  /49

  $1,995,000

  • 2 Beds
  • 2 Baths
  • 1,531 Sq Ft

  128 Newcut Rd, Bearsville, NY 12409

  At the end of a private road and surrounded by forever-protected land, you'll find this serene 25-acre mountaintop escape—complete with an additional contiguous 10-acre buildable lot. Build your dream, expand your vision, or simply enjoy the privacy and open space. Breathtaking views, open meadows, and total seclusion create the perfect backdrop for peaceful living. The home itself is a

  Gary DiMauro Four Seasons Sotheby's Int'l-K

  128 Newcut Rd, Bearsville, NY 12409
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  /30

  $499,000

  • 3 Beds
  • 3 Baths
  • 2,003 Sq Ft

  17 Hickory Ln, Glenford, NY 12433

  Enjoy the best of both worlds: peaceful country living just minutes from the vibrant towns of Woodstock, Phoenicia, and Kingston's historic uptown district with its array of art galleries, shops, cafes, and farmers markets. Outdoor enthusiasts will love the nearby Ashokan Rail Trail and the magnificent Ashokan Reservoir, just a short drive away.Charming and Versatile Country Cape with

  Margaret Bryngelson Off The Wall Management LLC

  17 Hickory Ln, Glenford, NY 12433
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  /31

  $749,900

  • 4 Beds
  • 2.5 Baths
  • 2,657 Sq Ft

  49 Dorns Wood Rd, Woodstock, NY 12498

  Nestled on 10.6 private acres at the end of a quiet cul-de-sac, this custom-built contemporary home offers a rare blend of privacy, space, and modern comfort, highlighted by charming Arts & Crafts details. This spacious 4-bedroom, 2.5-bath home features stunning handcrafted cherry woodwork in the kitchen and stairway, beautifully complemented by gorgeous hardwood floors throughout. A skylit foyer

  Megan Rios Berardi Realty

  49 Dorns Wood Rd, Woodstock, NY 12498
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  /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
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  /36

  $299,000

  • Land
  • 8 Acres
  • $37,143 per Acre

  00 Lot 2 Church Rd, Woodstock, NY 12409

  Embrace the opportunity to build your dream home in the idyllic surroundings of Woodstock, in beautiful Ulster County. Situated amidst tall evergreens and broadleaf trees with winding bluestone walls you are instantly enveloped in peace and serenity, this parcel offers the perfect setting for your Catskill Mountain retreat.Conscientiously subdivided parcels provide privacy and tranquility

  Melissa McGill Coldwell Banker Village Green

  00 Lot 2 Church Rd, Woodstock, NY 12409
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  /30

  $299,000

  • Land
  • 8 Acres
  • $39,708 per Acre

  0 Lot 1 Church Rd, Woodstock, NY 12409

  Embrace the opportunity to build your dream home in the idyllic surroundings of Woodstock. Situated amidst beautiful evergreen and broadleaf trees with winding bluestone walls you are instantly enveloped in peace and serenity, this parcel offers the perfect setting for your Catskill Mountain retreat.Conscientiously subdivided parcels provide privacy and tranquility with stunning rock

  Melissa McGill Coldwell Banker Village Green

  0 Lot 1 Church Rd, Woodstock, NY 12409
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  /39

  $749,000

  • 3 Beds
  • 2.5 Baths
  • 1,592 Sq Ft

  194 Wittenberg Rd, Bearsville, NY 12409

  Tucked away just three miles from the heart of Woodstock, this timeless 1845 farmhouse is a rare and soulful offering. The property is nestled on 1.8 acres of artfully landscaped gardens, all framed by dramatic rock ledges and outcroppings. At the heart of the property is the beautifully restored main home and a striking 700-square-foot heated yurt. The yurt is seamlessly integrated into the

  Leslie Foti Coldwell Banker Village Green

  194 Wittenberg Rd, Bearsville, NY 12409
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  /41

  $495,000

  • 3 Beds
  • 1.5 Baths
  • 1,506 Sq Ft

  3523 Route 212, Bearsville, NY 12409

  WHIMSICAL WOODSTOCK ARTS AND CRAFTS - Live in a home steeped in history while making your own. Welcome to ''Quixote'', built in 1905 by Woodstock builder and former Artificer in the Civil War, John ''Barney'' Hoyt. Vintage character blends seamlessly with modern convenience. Original details of this 3 bedroom, 2.5 bath gem include wide plank floor boards, pressed tin ceilings, custom built-ins

  Peter Cantine Halter Associates Realty

  3523 Route 212, Bearsville, NY 12409
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  /30

  $2,100,000

  • 9 Beds
  • 10 Baths
  • 8,452 Sq Ft

  0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498

  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 Hudson

  0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498
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  /38

  $795,000

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft

  276 Chestnut Hill Rd, Woodstock, NY 12498

  Tucked back on a six acre lot just minutes to the town of Woodstock sits this fairytale two bedroom cottage. The woodland view is yours to explore, the deep forest of evergreens, ferns and moss. Inside, you're tucked into charming spaces or enjoying the expansive Great Room, with a stone fireplace at the center and vaulted ceilings with beautiful exposed beams. A wall of windows frames the view.

  Annabel Taylor Four Seasons Sotheby's Int.

  276 Chestnut Hill Rd, Woodstock, NY 12498
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  /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
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  /10

  $168,000

  • Land
  • 2.10 Acres
  • $80,000 per Acre

  00 Whites Ln, Woodstock, NY 12498

  Prime location offering both privacy and proximity to the heart of Woodstock Village. Although the parcel's address is Whites Lane it is a fully wooded lot fronting Playhouse Lane Extension, a private and secluded road starting at the junction of Whites Lane and Playhouse. This setting is ideal for building your dream home while enjoying the convenience of walking to the Village. This parcel is

  Daniel Hauspurg Potter Realty

  00 Whites Ln, Woodstock, NY 12498
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  /33

  $2,175,000

  • 3 Beds
  • 2 Baths
  • 3,100 Sq Ft

  44 Old Wagon Rd, Wood Stock, NY 12498

  Just a short walk from the vibrant village of Woodstock, this exceptional modern contemporary home is truly one-of-a-kind. Designed by a renowned Park Avenue architect, this residence perfectly blends modern design and comfortable living, with no detail overlooked. As you enter through the foyer, you're immediately struck by the abundance of natural light streaming through the wall-to-wall

  Megan Rios Berardi Realty

  44 Old Wagon Rd, Wood Stock, NY 12498
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  /25

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,746 Sq Ft

  88 Boyce Rd, Glenford, NY 12433

  Set back from the road and nestled on 1.40 acres atop a gentle hill, sits a sprawling ranch , surrounded by woods and nature. This lovely three-bedroom, two-bath home has been thoughtfully maintained over the years, offering peace, privacy, and a true sense of seclusion. The open floor plan features hardwood floors and large windows throughout, filling the home with natural sunlight and warmth.

  Megan Rios Berardi Realty

  88 Boyce Rd, Glenford, NY 12433
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  /39

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 2,209 Sq Ft

  11 Louie Way, Woodstock, NY 12498

  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

  11 Louie Way, Woodstock, NY 12498
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  /32

  $1,649,000

  • 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
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  /50

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 3,439 Sq Ft

  1716 Route 212, Saugerties, NY 12477

  Step back in time with this enchanting antique farmhouse nestled on a sprawling 14-acre semi-rural retreat. This historical gem, built in the early 1800s, captures the rustic elegance of a bygone era while offering a tranquil sanctuary for nature lovers and history enthusiasts alike. Once the cherished residence of Jody Wolcott Carson (Johnny Carson's first wife) and Donald Bright Buckley, an

  Sara Gorman Maliha Coldwell Banker Village GreenK

  1716 Route 212, Saugerties, NY 12477
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  /44

  $1,299,000

  • 5 Beds
  • 3 Baths
  • 3,696 Sq Ft

  3207-3209 New York 212, Bearsville, NY 12409

  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

  3207-3209 New York 212, Bearsville, NY 12409
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  /56

  $549,000

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  680 Zena Rd, Woodstock, NY 12498

  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

  680 Zena Rd, Woodstock, NY 12498
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  /17

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  1145 Glasco Turnpike, Saugerties, NY 12477

  Stone walls line the beautiful wooded lot, featuring rock outcroppings and glacial boulders. Walk through the woods to truly feel the magic of this land. The home, built in 1979, has electric, well, and septic system; however, the condition of all systems is unknown, as the house has been vacant for years. A driveway is already in place. The house is set back from Glasco Turnpike, with the

  Shana Altstaetter Halter Associates Realty

  1145 Glasco Turnpike, Saugerties, NY 12477
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  /28

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft

  196 Tinker St, Woodstock, NY 12498

  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

  196 Tinker St, Woodstock, NY 12498
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  /34

  $1,495,000

  • 3 Beds
  • 2 Baths
  • 2,496 Sq Ft

  8 Tannery Brook Rd, Woodstock, NY 12498

  Positioned just moments from the vibrant energy of Tinker Street and the heart of Woodstock, this 2,496 sqft mixed-use property offers an exceptional opportunity to live, work, and invest in one of the Hudson Valley’s most iconic artistic communities. The first floor is owner-occupied, the upstairs serves as a well-established Airbnb, while the street-level commercial space is separately rented,

  STEVEN WROBEL JR. Serhant LLC

  8 Tannery Brook Rd, Woodstock, NY 12498
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  /50

  $1,450,000

  • 4 Beds
  • 4 Baths
  • 3,193 Sq Ft

  279 Cooper Lake Rd, Bearsville, NY 12409

  Nestled along one of the most enchanting, winding roads in Woodstock, this stunning contemporary ranch offers the perfect blend of modern convenience and serene country living with the bonus of a lot of extra space in the form of a lower-level accessory dwelling unit with a separate entrance; it adds two bedrooms and provides an ideal space for guests. Alternatively, it might be used as a

  Ellen Osgood Coldwell Banker Village Green

  279 Cooper Lake Rd, Bearsville, NY 12409
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  /66

  $1,450,000

  • 4 Beds
  • 4 Baths
  • 1,867 Sq Ft

  279 Cooper Lake Rd, Woodstock, NY 12498

  Nestled along one of the most enchanting, winding roads in Woodstock, this stunning contemporary ranch offers the perfect blend of modern convenience and serene country living with the addition of a lot of extra space in the form of a lower-level accessory dwelling unit with a separate entrance; it adds two bedrooms and provides an ideal space for guests. Alternatively, it might be used as a

  Ellen Osgood Coldwell Banker Village Green

  279 Cooper Lake Rd, Woodstock, NY 12498
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  /33

  $1,999,999

  • 4 Beds
  • 3 Baths
  • 4,312 Sq Ft

  115 Band Camp Rd, Saugerties, NY 12477

  Nestled on a country road at the end of a long driveway, this unique home offers complete privacy on a stunning 13-acre property. Located just minutes from the town centers of Saugerties and Woodstock, you'll have access to great restaurants and shopping. This house perfectly balances the need for seclusion with exciting local activities, providing the best of the Hudson Valley experience.

  Sheena Lepez Compass Greater NY, LLC

  115 Band Camp Rd, Saugerties, NY 12477
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  /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
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  /34

  $599,000

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  40 Lower Byrdcliffe Rd, Woodstock, NY 12498

  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

  40 Lower Byrdcliffe Rd, Woodstock, NY 12498
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  /23

  $450,000

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft

  55 John St, West Hurley, NY 12491

  Nestled in the picturesque hamlet of West Hurley, New York, this charming residence offers a wonderful opportunity to embrace the tranquility and natural beauty of the Catskill Mountains. Situated in a beautiful neighborhood, this property provides a true escape while remaining conveniently located to local amenities.

  Alexander Rokicki Pennywise Properties

  55 John St, West Hurley, NY 12491
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  /23

  $250,000

  • Land
  • 2.19 Acres
  • $114,155 per Acre

  1145 Glasco Turnpike, Saugerties, NY 12477

  2.19 acres. Stone walls line the beautiful wooded lot, featuring rock outcroppings and glacial boulders. The home, built in 1979, has electric, well, and a septic system; however, the condition of all systems is unknown, as the house has been vacant for years. A driveway is already in place. The house is set back from Glasco Turnpike, with the garage situated further back. The property is being

  Shana Altstaetter Halter Associates Realty Inc

  1145 Glasco Turnpike, Saugerties, NY 12477
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  /33

  $599,000

  • 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

  Michael Alpert Daniel Gale Sothebys Intl Rlty

  328 John Joy Rd, Woodstock, NY 12498
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  /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
• 

  

  /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
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  /79

  $2,500,000

  • 7 Beds
  • 7 Baths
  • 3,960 Sq Ft

  2465 Glasco Turnpike, Woodstock, NY 12498

  Discover a rare opportunity in the heart of Woodstock, NY— with special status, granted by NYS supreme court, which allows rentals of any length, anytime, not subject to any restrictions from the town of Woodstock, or the county. This five-cabin retreat is on over 6 private acres, offering multiple possibilities: a thriving short-term rental, a secluded family/friends compound, or a unique

  Mirav Ozeri The Machree Group, LLC

  2465 Glasco Turnpike, Woodstock, NY 12498
• 

  

  /25

  $500,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  3271 Route 212, Bearsville, NY 12409

  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

  Pieta Williams Halter Associates Realty

  3271 Route 212, Bearsville, NY 12409
• 

  

  /25

  $500,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  3271 Route 212, Bearsville, NY 12409

  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

  Pieta Williams Halter Associates Realty

  3271 Route 212, Bearsville, NY 12409
• 

  

  /33

  $1,888,000

  • Land
  • 61 Acres
  • $30,981 per Acre

  TBD Zena Rd, Woodstock, NY 12498

  An incredible, rare opportunity in Woodstock. It has been very long time since a parcel of this magnitude has available for sale in Woodstock. This contiguous 60-acre property, consisting of two 30-acre lots, features rolling hills, stunning rock outcroppings, mountain views, and diverse mature trees, uniquely offering both beauty and potential. A privately built road, completed by the owners,

  Baris Demirel Serhant LLC

  TBD Zena Rd, Woodstock, NY 12498
• 

  

  /28

  $1,888,000

  • Land
  • 61 Acres
  • $30,981 per Acre

  TBD 60 Acre Zena Rd, Woodstock, NY 12498

  An incredible, rare opportunity in Woodstock.It has been very long time since a parcel of this magnitude has available for sale in Woodstock. This contiguous 60-acre property, consisting of two 30-acre lots, features rolling hills, stunning rock outcroppings, mountain views, and diverse mature trees, uniquely offering both beauty and potential. A privately built road, completed by the

  Baris Demirel Serhant LLC

  TBD 60 Acre Zena Rd, Woodstock, NY 12498
• 

  

  /31

  $219,000

  • Land
  • 3.43 Acres
  • $63,848 per Acre

  2 John Joy Rd, Woodstock, NY 12498

  Embrace the opportunity to build your dream home on this shovel-ready building lot in the idyllic surroundings of Woodstock, New York. Situated amidst incredible trees and enveloped in peace and tranquility, this parcel offers the perfect setting for your Catskill Mountain retreat. With approvals for septic already in place and a potential building site identified, the land has been meticulously

  Eric Amaral Coldwell Banker Village Green

  2 John Joy Rd, Woodstock, NY 12498

Showing Results 41 - 80, Page 2 of 3