Homes for Sale near Woodstock Day School

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  /62

  $1,850,000

  • 3 Beds
  • 3 Baths
  • 3,319 Sq Ft

  9 Cooper Lake Rd, Bearsville, NY 12409

  A secluded mountain escape awaits you in one of Woodstock's preeminent neighborhoods. Tucked away on Cooper Lake Road—famous for its dramatic lake and mountain vistas—this home offers privacy while being just minutes from the town's legendary music venues, galleries, and fine dining. The welcoming front entry of this home unfolds to an airy and open layout accented by soaring beamed ceilings and

  

  Amy Lonas

  Coldwell Banker Village Green

  (845) 932-1530

  9 Cooper Lake Rd, Bearsville, NY 12409
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  Explore Woodstock Day School

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  /38

  $689,000

  • 2 Beds
  • 3 Baths
  • 1,208 Sq Ft

  18 Country Club Ln, Woodstock, NY 12498

  Stunning reimagined Ranch, just 1/2 Mile from the Center of Woodstock, 2/10 of a Mile to the NYC Bus Route, yet providing an excellent sense of privacy, and a perfect rural setting. Beautifully, and thoughtfully updated baths and kitchen, embracing the best of Modern Design principles and practicality. The perfect country escape, yet within easy access to restaurants, shopping and all outdoor

  

  Win Morrison

  Win Morrison Realty

  (845) 470-4906

  18 Country Club Ln, Woodstock, NY 12498
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  /43

  $1,199,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,942 Sq Ft

  178 Chestnut Hill Rd, Woodstock, NY 12498

  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

  Richard Vizzini Corcoran Country Living

  178 Chestnut Hill Rd, Woodstock, NY 12498
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  /31

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 2,316 Sq Ft

  11 Forestwood Dr, Woodstock, NY 12498

  Set in a quiet, welcoming neighborhood just minutes from Woodstock's center, this beautifully appointed home feels like a place where life can truly take shape. With 2,316 square feet of thoughtful living space, three generous bedrooms, and 2.5 baths, it offers comfort, warmth, and room to grow. The .86-acre property feels remarkably private, with no neighbors behind you and a serene backyard

  Laurie Ylvisaker Coldwell Banker Village Green

  11 Forestwood Dr, Woodstock, NY 12498
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  /35

  $799,000

  • 4 Beds
  • 2 Baths
  • 1,948 Sq Ft

  4 Munchkin Ln, Kingston, NY 12401

  Highwoods Haven rests on just over two 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

  Leslie Foti Coldwell Banker Village Green

  4 Munchkin Ln, Kingston, NY 12401
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  /52

  $1,340,000

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  66 Plochmann Ln, Woodstock, NY 12498

  So close yet so far away! Walk to town from your totally private and like-new timber frame home with soaring 23-foot ceilings and walls of windows to bring nature in. As you enter from one of Woodstock's most coveted roads, through the stately pillars, you will feel a sense of tranquility with nature on this 9.94-acre lot that is just a half mile from the village of Woodstock and less than a half

  Mercedes Ross Coldwell Banker Village Green

  66 Plochmann Ln, Woodstock, NY 12498
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  /41

  $825,000

  • 3 Beds
  • 3 Baths
  • 1,895 Sq Ft

  345 Glenford Wittenberg Rd, Glenford, NY 12433

  Set on three wooded and landscaped acres in the heart of the Catskills, this beautifully designed home blends modern comfort with timeless country charm. Offering 3 bedrooms, 3 bathrooms, including an attached ADU, the property is ideal for multi-generational living, guest accommodations, or additional rental income. Make your way to the top of the long tree lined driveway to be greeted by the

  Richard Vizzini Corcoran Country Living

  345 Glenford Wittenberg Rd, Glenford, NY 12433
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  /36

  $925,000

  • 3 Beds
  • 2 Baths
  • 1,998 Sq Ft

  64 Lower Byrdcliffe Rd, Woodstock, NY 12498

  This historic Woodstock home, complete with a legal short-term rental license, is ready for its next chapter. Just a short distance from the iconic village green and the heart of Woodstock, this recently restored 1897 Arts and Crafts farmhouse offers both privacy and convenience on one of the town's most desirable streets - a truly rare combination that seldom becomes available. The charming

  Victoria Stent Coldwell Banker Village Green

  64 Lower Byrdcliffe Rd, Woodstock, NY 12498
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  /31

  $525,000

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft

  233 Wittenberg Rd, Bearsville, NY 12409

  Picture yourself in this charming 1940 cottage with a roaring fire in its fieldstone double-height fireplace. If that doesn't capture your heart, the open living and dining areas with birch beamed ceilings will. Large expanses of windows flood the space with light, adding more charm essential to modern living. A wonderfully convenient full bath with claw-foot tub adds to the easy living. The

  Henry Ford Coldwell Banker Village Green

  233 Wittenberg Rd, Bearsville, NY 12409
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  /49

  $995,000

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

  1716 Route 212, Saugerties, NY 12477

  Live in an atmosphere you have always dreamed of. Become the talk of the town...your imagination escapes you...! Step back in time with this enchanting antique farmhouse nestled on a sprawling 10+-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.

  Sara Gorman Maliha Coldwell Banker Village GreenK

  1716 Route 212, Saugerties, NY 12477
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  /43

  $1,085,000

  • 3 Beds
  • 2 Baths
  • 2,985 Sq Ft

  68 Cooper Hollow Rd, Bearsville, NY 12409

  Welcome to this very special Whimsical Storybook Contemporary, designed by Architect David Minch and built in 2004. Has been Meticulously maintained and ready for new owners to enjoy the tranquility and privacy this home has to offer. Home is situated at the end of a quiet road on 5.82 acres, 3 miles from the Village of Woodstock and close to Cooper Lake Reservoir. Three bedrooms, two full

  Nancy Berish BHHS Hudson Valley Properties

  68 Cooper Hollow Rd, Bearsville, NY 12409
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  /27

  $1,175,000

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  210 Dutchtown Rd, Saugerties, NY 12477

  Located on a quiet dead end road, with a tranquil and private 5.25 acre lot, find Highwoods - a stylish new construction home with all the comforts you could imagine in a full time residence or weekend getaway. Highwoods brings together a modern aesthetic and a practical design, with its spacious 2280 square foot 3 bedroom 2 bath layout. Thoughtfully crafted, this new build feels perfectly at

  Kayla Camstra Anatole House LLC

  210 Dutchtown Rd, Saugerties, NY 12477
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  /49

  $793,000

  • 4 Beds
  • 2.5 Baths
  • 2,034 Sq Ft

  90 Van Dale Rd, Woodstock, NY 12498

  Make your next transition an easy one in this move-in-ready Woodstock home, where timeless comfort meets sophisticated design. Recently updated and fully renovated—including a brand-new roof and a full-house water filtration system—the house is set on a large, level lot with expansive front and back yards, offering plenty of space to relax, entertain, and play. Just minutes from Woodstock’s

  Baris Demirel Serhant LLC

  90 Van Dale Rd, Woodstock, NY 12498
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  /25

  $795,000

  • 4 Beds
  • 2.5 Baths
  • 1,754 Sq Ft

  86 Rock City Rd, Woodstock, NY 12498

  Woodstock Charm Meets Modern Living at 86 Rock City Road!Step into a piece of Woodstock history with this beautifully updated 1910 home, ideally located less than half a mile from the vibrant heart of the village. This 4-bedroom, 2.5-bath property blends classic charm with thoughtful modern upgrades. The spacious, fully renovated kitchen features new appliances, updated countertops, and ample

  Michael Shaughnessy Halter Associates Realty

  86 Rock City Rd, Woodstock, NY 12498
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  /26

  $895,000

  • 4 Beds
  • 2 Baths
  • 2,572 Sq Ft

  55 Lennox Ave, Glenford, NY 12433

  Rarely available antique farmhouse offering history, privacy, and seasonal Ashokan Reservoir views—just minutes from Woodstock and Kingston yet tucked away on 6.9 acres. Once Glenford's post office under the Lennox family, this pre-1900 home blends timeless character with thoughtful updates. Light-filled interiors feature unusually high ceilings [on the main level] for its era, hand-cut oak and

  Harris Safier Compass Greater New York, LLC

  55 Lennox Ave, Glenford, NY 12433
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  /44

  $939,000

  • 3 Beds
  • 2.5 Baths
  • 2,430 Sq Ft

  220 John Joy Rd, Wood Stock, NY 12498

  Tucked back from the road, with beautifully landscaped grounds, bluestone walls, and mature plantings, this 3-bedroom contemporary home offers privacy, abundant natural light, and versatile living space on 4 tranquil acres. The airy open floor plan features hardwood floors and effortless flow between the living, dining, and kitchen areas. A first-floor primary suite with en-suite bath provides

  Lisa Cooper Serhant LLC

  220 John Joy Rd, Wood Stock, NY 12498
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  /42

  $1,199,000

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

  3207-3209 New York 212, Bearsville, NY 12409

  Enchanting Woodstock Compound with three separate buildings—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,

  Michelle Bergkamp William Pitt Sotheby's Interna

  3207-3209 New York 212, Bearsville, NY 12409
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  /45

  $1,495,000

  • 6 Beds
  • 6 Baths
  • 6,164 Sq Ft

  174 Bristol Hill Rd, Glenford, NY 12433

  Secluded 6-Bedroom Estate with Seasonal Reservoir Views and Stunning Sunrises !sauna, reservoir view, Woodstock, luxury kitchen, elevator shaft, accessibility and grand staircase Nestled on a quiet, picturesque road just 4 miles from the heart of Woodstock, this extraordinary 6-bedroom, 6-bathroom estate offers privacy, craftsmanship, and timeless character on nearly 2 acres of lush, serene

  Thomas Pignone Green Ventures Realty

  174 Bristol Hill Rd, Glenford, NY 12433
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  /29

  $898,000

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  14 Old Forge Rd, Woodstock, NY 12498

  PROPERTY HIGHLIGHTS. Historic Meets Modern: Exquisitely renovated 1900 carriage house blending timeless charm with contemporary luxury. Layout: 2 bedrooms and 2 bathrooms. Exceptionally rare construction featuring Steel floor and ceiling joists with comprehensive Energy Efficient Upgrades throughout. INTERIOR FEATURESKITCHEN: Energy Efficient and dependable Bosch appliances. Custom

  Danielle Sevier Compass Greater NY, LLC

  14 Old Forge Rd, Woodstock, NY 12498
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  /31

  $948,880 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,252 Sq Ft

  32 Maurizi Ln, Woodstock, NY 12498

  Blending classic country charm with modern sophistication, this newly built modern farmhouse offers over 3,000 square feet of beautifully finished living space. Designed with clean lines, a neutral palette, and layered textures, it delivers a timeless aesthetic full of warmth and character. The home features four spacious bedrooms, three and a half baths, a fully finished lower level, and

  Richard Vizzini Corcoran Country Living

  32 Maurizi Ln, Woodstock, NY 12498
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  /45

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,968 Sq Ft

  132 Dutchtown Rd, Saugerties, NY 12477

  *PCS DO NOT SHOW* This beautiful high ranch has stunning mountain and water views. It's located on one of the most desireable country roads in Saugerties. You can stroll safely down this low traffic dead end road with your kids and/or pets. A public 40 acre conservation land half way down the road is great for hiking This home three bedrooms and two full baths. The kitchen and both baths have

  William Chris St. John Win Morrison Realty

  132 Dutchtown Rd, Saugerties, NY 12477
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  /50

  $324,000

  • 2 Beds
  • 1 Bath
  • 1,087 Sq Ft

  77 Pine St, West Hurley, NY 12491

  Discover this charming 1,087 sq ft, single-level cottage featuring hardwood floors, a cozy brick propane fireplace, and bright, open living spaces. Set on two adjoining parcels totaling 1.46 acres, the property offers peace and room to expand and there’s even space for a pool. A heated 2-car detached garage provides year-round convenience, while multiple outbuildings including gazebos, sheds, and

  Maureen Mayone Howard Hanna Rand Realty

  77 Pine St, West Hurley, NY 12491
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  /10

  $125,000

  • Land
  • 0.58 Acre
  • $215,517 per Acre

  5485 New York 212, Shandaken, NY 12480

  CAUTION ! The garage on the property has previously caught fire .Must be torn down .DO NOT ENTER THE GARAGE Prime Catskills Land Listing - HB Commercial/Residential ZoningPerfectly positioned in the heart of the Catskills, this 1⁄2+ acre parcel offers dream-worthy mountain views and unbeatable access to the region's most sought-after outdoor attractions. Whether you're planning a

  Stephanie Berryann United Real Estate HV Edge

  5485 New York 212, Shandaken, NY 12480
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  /46

  $649,900

  • 3 Beds
  • 2.5 Baths
  • 2,275 Sq Ft

  176 Old State Route 28, Glenford, NY 12433

  Welcome to “The Glenford” – a stunning newly renovated ranch home that perfectly blends modern comfort with timeless charm. Nestled just minutes away from the picturesque Village of Woodstock this delightful property offers a serene escape with all the amenities you desire. The floor plan consists of 3 spacious bedrooms and 2.5 bathrooms; each designed with comfort and relaxation in mind.

  Darnell Williams R New York

  176 Old State Route 28, Glenford, NY 12433
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  /30

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,489 Sq Ft

  34 Forestwood Dr, Woodstock, NY 12498

  34 Forestwood Drive | Woodstock, NY Set along a quiet Woodstock road, this inviting raised ranch blends space, comfort, and mid-century charm. With 4 bedrooms, 2.5 baths, and 10 well-proportioned rooms, the home offers flexibility for both everyday living and weekend getaways in one of the Hudson Valley's most sought-after areas. Step inside the split open entry to a bright, welcoming layout. The

  Brenda Graf Corcoran Country Living

  34 Forestwood Dr, Woodstock, NY 12498
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  /22

  $350,000

  • 4 Beds
  • 1 Bath
  • 1,284 Sq Ft

  376 Band Camp Rd, Saugerties, NY 12477

  Bring your things and move right into this well maintained 4 bedroom home. Enjoy cooking in the large eat-in kitchen or relaxing in the bright and sunny living room. Sit by the outdoor fire pit on autumn days or BBQ with friends during the summer. The layout of the house has a great flow making the house feel spacious and perfect for entertaining or simply relaxing after a long day. Two of the

  Rose Noone BHHS HUDSON VALLEY PROP-WDST

  376 Band Camp Rd, Saugerties, NY 12477
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  /20

  $69,900

  • 3 Beds
  • 1.5 Baths
  • 1,000 Sq Ft

  130 Timberwall Rd Unit 24, Saugerties, NY 12477

  Bright, refurbished mobile home in quiet park with nice level lot. All taxes included in the 675 monthly lot fee. HUD NTA 259857

  Timothy Ayers Berardi Realty

  130 Timberwall Rd Unit 24, Saugerties, NY 12477
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  /39

  $575,000

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

  40 Lower Byrdcliffe Rd, Woodstock, NY 12498

  Just a stone's throw away from Woodstock’s vibrant cultural scene, this charming Arts and Crafts home blends original character with modern updates. A comprehensive renovation includes a brand-new septic and heating system, updated kitchen and baths, new flooring, lighting, paint, and enhanced insulation. Original stained-glass windows remain 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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  /40

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,077 Sq Ft

  1521 Glasco Turnpike, Saugerties, NY 12477

  An exceptional convergence of wish-list features comes together in one remarkable package. This well-built Colonial enjoys an ideal location — a perfect balance of privacy and convenience — situated right on the border of Woodstock and Saugerties, with easy access to Kingston. Tucked away at the end of a long driveway, the home sits amid a picturesque mix of forest and open meadow, creating a

  Sean Zimmerman Halter Associates Realty Inc

  1521 Glasco Turnpike, Saugerties, NY 12477
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  /34

  $1,475,000

  • Land
  • 25.38 Acres
  • $58,117 per Acre

  132 Valley View Way, Woodstock, NY 12448

  The Ledges at Valley View High above the Beaverkill River, where the Catskills unfold in a sweep of peaks and light, lies The Ledges at Valley View - a design-ready estate site where modern architecture meets the mountain. Sited on more than 25 private acres, this south-facing ridgeline property captures cinematic views of Twin, Indian Head, Overlook, and Mount Guardian. The land adjoins

  Margaret Bellar The Catskill Dream Team

  132 Valley View Way, Woodstock, NY 12448
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  /35

  $599,000

  • 4 Beds
  • 3 Baths
  • 2,480 Sq Ft

  5 Lazy Brook Ln, Woodstock, NY 12498

  Step inside for a huge surprise! This tasteful ranch home hides 3 large living spaces, 4 spacious bedrooms 3 bathrooms, as well as an enormous pantry and dining space. You enter and the first living space is on your right with room for a full sized seating area. Down the hall to your left are two bedrooms, a hall bath and a primary en suite with room for a king sized bed. Through a door in the

  Richard Stoll Halter Associates Realty

  5 Lazy Brook Ln, Woodstock, NY 12498
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  /15

  $625,000

  • Land
  • 22 Acres
  • $28,409 per Acre

  0 Band Camp Unit 20255121, Saugerties, NY 12477

  Whispering Winds — 22 Acres of History and HarmonyPerfect for those seeking privacy, inspiration, and connection to the land, this remarkable 22.1 acre property offers quiet beauty and deep history. A spring-fed 2.2-acre pond, woodland trails, and the peaceful songs of nature create a timeless sense of serenity and retreat nestled between Woodstock and Saugerties.Once home to the

  Nancy Felcetto Brown Harris Stevens Hudson

  0 Band Camp Unit 20255121, Saugerties, NY 12477
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  /49

  $3,500,000

  • 4 Beds
  • 4 Baths
  • 4,201 Sq Ft

  289 Upper Byrdcliffe Rd, Woodstock, NY 12498

  Set on nearly 9 serene acres in the heart of Woodstock's historic Byrdcliffe Arts Colony is a rare synthesis of architectural precision and natural harmony—an embodiment of award-winning architect John Storyk's deep understanding of space, sound, and site. Designed in 1969 at the very beginning of Storyk's now-legendary career—just after his groundbreaking work on Jimi Hendrix's Electric Lady

  Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

  289 Upper Byrdcliffe Rd, Woodstock, NY 12498
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  /14

  $625,000

  • Land
  • 22.1 Acres
  • $28,281 per Acre

  O Band Camp Rd, Saugerties, NY 12477

  Whispering Winds — 22 Acres of History and HarmonyPerfect for those seeking privacy, inspiration, and connection to the land, this remarkable 22.1-acre property offers quiet beauty and deep history. A spring-fed 2.2-acre pond, woodland trails, and the peaceful songs of nature create a timeless sense of serenity and retreat nestled between Woodstock and Saugerties.Once home to the

  Nancy Felcetto Brown Harris Stevens HV LLC

  O Band Camp Rd, Saugerties, NY 12477
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  /51

  $4,200,000

  • 2 Beds
  • 4 Baths
  • 3,024 Sq Ft

  306 Meads Mountain Rd, Woodstock, NY 12498

  Swoop House is a residence with two great rooms, one of which was designed as a professional art studio. Designed by FT Architecture & Interiors, and inspired by the Diller Scofidio Slow House, the 5000 square feet span three levels. This singular residence is sited at the end of a long driveway on Overlook Mountain on 16 peaceful and private acres. This property provides you with both distant

  Kimberly Cantine Halter Associates Realty

  306 Meads Mountain Rd, Woodstock, NY 12498
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  /6

  $775,000

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft

  31 Pond Park Rd, Woodstock, NY 12498

  Woodstock Condo at Maverick Knolls Discover an exceptional opportunity to own a single-level corner condo in the desirable Maverick Knolls community of Woodstock, NY. This bright and airy residence combines convenience, modern updates, and the natural beauty of the Catskills, making it ideal for year-round living or as a low-maintenance retreat. The home has been refreshed with all new appliances

  Frank Lumia Frank Lumia Real Estate Plus

  31 Pond Park Rd, Woodstock, NY 12498
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  /37

  $1,200,000

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  8 Tannery Brook Rd, Woodstock, NY 12498

  Large shade trees filter dappled sunlight across this property's private waterside retreat, where the ancient stone wall of the streambed tells the story of millennia, smoothed by the eternal passage of water. Just steps from the vibrant rhythm of Tinker Street and the creative heartbeat of Woodstock, this nearly 2,500 square foot mixed-use property is more than a home or an investment, it is a

  Leslie Foti Coldwell Banker Village Green

  8 Tannery Brook Rd, Woodstock, NY 12498
• 

  

  /23

  $750,000

  • Land
  • 5.45 Acres
  • $137,615 per Acre

  326 Raycliffe Dr, Woodstock, NY 12498

  Discover a rare opportunity to own 5.45 acres atop one of Woodstock's most coveted locations. This private, east-facing lot offers panoramic views that stretch endlessly over the Catskill Mountains, providing an awe-inspiring backdrop for your dream home. With the space and natural beauty to build a sleek, modern estate, this land is the perfect canvas for a luxury retreat. Surrounded by the

  Alexis Li Corcoran Country Living

  326 Raycliffe Dr, Woodstock, NY 12498
• 

  

  /11

  $499,000

  • Land
  • 15.23 Acres
  • $32,764 per Acre

  Tbd Wardwell Ln, Woodstock, NY 12498

  A rarely available large, 15+ acre parcel in Woodstock -- less than a mile from the center of town! Completely private yet moments away from restaurants, music venues, shops, golf course and hiking. A mixture of mature deciduous and conifer trees offer a forest haven, with level land, rock features and an elevated knoll building site, ready for your next chapter.Much of the heavy lifting

  Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

  Tbd Wardwell Ln, Woodstock, NY 12498
• 

  

  /44

  $2,250,000

  • 4 Beds
  • 4 Baths
  • 4,730 Sq Ft

  9 Estate Rd, Saugerties, NY 12477

  Wind along quiet country roads to the end of a private cul-de-sac and discover a magical retreat where timeless elegance meets modern comfort. Beyond the electronic gates, manicured grounds framed by mature woodland set the stage for this four-bedroom, four-bathroom, 4,700-square-foot custom residence.Outdoor living is at its finest with a sweeping bluestone patio and hot tub, a serene

  Laurie Ylvisaker Coldwell Banker Village Green

  9 Estate Rd, Saugerties, NY 12477

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