Homes for Sale near Reginald Bennett Elementary School

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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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  /35

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,975 Sq Ft

  7202 New York 28, Shandaken, NY 12480

  CATSKILLS LIVING AT ITS FINEST This Circa 1880 country home (totally renovated in 2007) sits on a grassy landscaped acre in the heart of the Catskill Mountains. This property has been a very successful Airbnb/VRBO. The fully insulated house has 1975 SF with 3 BRs, 2 BAs, large Foyer, open floor plan, stunning cobblestone fireplace, and a great cast iron clawfoot tub that leads to the main BR

  Alfred Peavy Ruth Gale Realty

  7202 New York 28, Shandaken, NY 12480
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  /17

  $389,000

  • 4 Beds
  • 2 Baths
  • 1,880 Sq Ft

  2832 New York 28, Shokan, NY 12481

  Interesting Multi-Unit Property in the Lovely Town of Olive. The Main house has 3 Bedrooms and 1 Bath with recent Renovations to the Kitchen, Bathroom, Mudroom and Breezeway. There's a Newer Roof also! On the far end of this elongated Ranch, separated by a Utility Room and Garage, is an Efficiency Apartment (currently rented). The house is well set back from the road with a wall of trees for

  Edwin Maldonado Howard Hanna Rand Realty

  2832 New York 28, Shokan, NY 12481
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  /41

  $1,375,000

  • 4 Beds
  • 4 Baths
  • 3,941 Sq Ft

  465 High Point Mountain Rd, West Shokan, NY 12494

  Available for the first time in 50-plus years, this iconic Hudson Valley home boasts extraordinary character and charm in the perfect setting -- a secluded 10-acre nook of ponds and woods just minutes from the Ashokan Reservoir. The house, a masterful blend of timeless farmhouse style, craftsmanship and luxury, is the polar opposite of cookie cutter, with classic window awnings, cedar shakes and

  Hayes Clement Compass Greater New York, LLC

  465 High Point Mountain Rd, West Shokan, NY 12494
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  /31

  $415,000

  • 3 Beds
  • 2 Baths
  • 2,343 Sq Ft

  62 Andrew Ln, Mount Tremper, NY 12457

  All the essentials are here—hardwood floors, an eat-in kitchen, and a light-filled living room that opens to a screened porch. Located in the Catskill foothills, just minutes from skiing, hiking, Woodstock, Kingston, and all the best of the Hudson Valley.This 3-bedroom, 2-bath home sits on 2.97 acres with a garage, barn, and outbuilding. With 2,343 sq ft and room to enjoy the outdoors,

  Robert Airhart Compass Greater New York, LLC

  62 Andrew Ln, Mount Tremper, NY 12457
• 

  

  /41

  $925,000

  • 6 Beds
  • 3.5 Baths
  • 2,610 Sq Ft

  204-208 New York 42, Shandaken, NY 12480

  Tucked away on 10 private, wooded acres in the heart of the Catskills, this unique compound offers the perfect blend of rustic charm, modern comfort, and income-generating potential. With a 4-bedroom, 2.5-bath main house and a separate 2-bedroom, 1-bath guest house, this serene escape is ideal for full-time living, weekend getaways, or as a turnkey investment property. The grounds feature a pool,

  Jason Nadeau Compass Greater NY, LLC

  204-208 New York 42, Shandaken, NY 12480
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  /28

  $275,000

  • 0.5 Baths
  • 3,297 Sq Ft

  71 Watson Hollow Rd, West Shokan, NY 12494

  If you are looking for a well maintained huge open light filled, heated space with a well and septic and water to convert into your home/studio look no further! Fantastic location with easy access to Boiceville and Route 28 this exceptional building has one half bathroom a double furnace and an additional wet sink area. Just minutes from Woodstock, Phoenicia and Boiceville with shopping and

  Faye Storms Ruth Gale Realty

  71 Watson Hollow Rd, West Shokan, NY 12494
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  /61

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  258 Watson Hollow Rd, West Shokan, NY 12494

  Spacious 3 bedroom home with breathtaking mountain views. Perched on a hill, this home offers panoramic mountain views and sits on 19.20 acres bordered by a serene stream. There is a front entrance to the home that brings you into the lower level foyer room with blue stone flooring.. On this level is a finished game room/ office space/TV room with plenty of finished space. You also have access to

  Siobhan Scanlan Win Morrison Realty-K

  258 Watson Hollow Rd, West Shokan, NY 12494
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  /36

  $1,995,995

  • 7 Beds
  • 6 Baths
  • 7,020 Sq Ft

  589-595 Plank Rd, Phoenicia, NY 12464

  This beautiful estate must be seen. Owned by the same family for over 40 years, the compound has been lovingly expanded and restored. It is anchored by an 1870 farmhouse with many amenities. You enter the house to a wonderful chef's kitchen with cathedral ceilings accompanied by a walk-in pantry. There are granite countertops and top appliances. The first floor includes a spacious entertaining

  Michael Shaughnessy Halter Associates Realty Inc

  589-595 Plank Rd, Phoenicia, NY 12464
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  /36

  $1,400,000

  • 3 Beds
  • 4 Baths
  • 3,120 Sq Ft

  540 Mount Tobias Rd, Mount Tremper, NY 12457

  Step into the pages of Dwell magazine and immerse yourself in this architect-designed gem offering a harmonious blend of modern design and natural beauty. Feel a wave of calm wash over you, greeted by resplendent views, clean lines, and a wall of windows overlooking majestic mountain vistas. Modernists rejoice. Design aficionados delight. And nature enthusiasts revel. A minimalist aesthetic

  Alexander James Fresh Air Realty

  540 Mount Tobias Rd, Mount Tremper, NY 12457
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  /28

  $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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  /62

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft

  5221-5223 New York 28, Mount Tremper, NY 12457

  *One-of-a-Kind Mountain Farmhouse with Guest Cottage on the Esopus Creek*Discover this 4-bedroom, 2-bath farmhouse full of character and beauty nestled on 1.96 enchanting meadow-like acres in Mount Tremper. Built in 1890 and lovingly maintained, this timeless home blends vintage charm with tasteful updates. The interior features hardwood floors, a wood-burning stove in the living room and a

  Amy Owens Coldwell Banker Village Green

  5221-5223 New York 28, Mount Tremper, NY 12457
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  /38

  $1,200,000

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

  94 the Middle Way, Mount Tremper, NY 12457

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

  Jennifer Grimes Country House Realty Inc

  94 the Middle Way, Mount Tremper, NY 12457
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  /55

  $977,000

  • 4 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  23 Riseley Ln, Shandaken, NY 12480

  Nestled at the end of a quiet dead-end road and the only house on the road, in the heart of Panther Mountain Park, this stunning Mid-Century Saltbox-style home offers unmatched privacy & serenity. It's such a rare find—only the second time it's ever been on the market. Set on over 4 acres and directly bordering State Land, this home offers privacy, unforgettable stream views, and an intimate

  Richard Greenspan Ruth Gale Realty

  23 Riseley Ln, Shandaken, NY 12480
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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

  $1,749,900

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

  16 Juniper Ln, Woodstock, NY 12498

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

  Victoria Stent Coldwell Banker Village Green

  16 Juniper Ln, Woodstock, NY 12498
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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

  $899,000

  • 4 Beds
  • 3 Baths
  • 2,125 Sq Ft

  48 Cooper Hollow Rd, Bearsville, NY 12409

  Tucked away on a scenic country road just minutes from historic Woodstock, this stunning contemporary home offers the perfect balance of privacy, tranquility, and access to nature. Set on six acres in a highly desirable neighborhood, this serene retreat is surrounded by lush woods, artfully landscaped grounds, and a feeling of peace that begins the moment you arrive. With nearby hiking trails,

  Eric Amaral Coldwell Banker Village Green

  48 Cooper Hollow Rd, Bearsville, NY 12409
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  /19

  $249,000

  • Land
  • 5 Acres
  • $48,824 per Acre

  TBD New York 28a, West Hurley, NY 12491

  LOCATED A FEW PARCELS PASSED THE LIVING WORLD CHAPEL@ 1555 RT 28A WITH SIGN ON. CURB CUT IN PLACESerene 5± Acres Near the Ashokan Reservoir - A Blank Canvas for Your Dream HomeTucked away on a quiet country road just minutes from the shimmering waters of the Ashokan Reservoir, this peaceful 5± acre parcel offers the perfect balance of seclusion and accessibility. A harmonious mix of mature

  Jeanne Boice Howard Hanna Rand Realty

  TBD New York 28a, West Hurley, NY 12491
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  /42

  $410,000

  • 2 Beds
  • 2 Baths
  • 1,196 Sq Ft

  2 Shokan Park Rd, Shokan, NY 12481

  Two bedroom, two bath ranch style home. Updates include brand new carpet, Vinyl plank flooring and some sheetrock. Home is freshly painted and just ready for you to move in. Home features floor to ceiling windows in the kitchen and living room. We are sure you will absolutely enjoy all the natural light all day long and watching all the changing of the seasons through them. Yard has beautiful

  Toni Scalici Asset Property Services

  2 Shokan Park Rd, Shokan, NY 12481
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  /30

  $2,400,000

  • 13 Beds
  • 5 Baths
  • 8,000 Sq Ft

  540 New York 42, Shandaken, NY 12480

  Experience the best of Catskills living at the Mountain Brook Inn, a beautifully restored historic home in Shandaken, NY. Originally built in 1805 and extensively renovated for 2025, this remarkable residence offers nearly 8,000 square feet of living space on a picturesque 1-acre lot along the tranquil Bushnellsville Creek. The home spans three levels, featuring seven spacious bedrooms on the

  Alicia Goldman Christie's Int. Real Estate

  540 New York 42, Shandaken, NY 12480
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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

  $1,700,000 Open Sun 12PM - 2PM

  • 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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  /11

  $35,000

  • Land
  • 2.00 Acres
  • $17,500 per Acre

  Tbd New York 28, Oliverea, NY 12725

  2 acres of raw beauty in Big Indian NYNestled in the heart of the Catskill Mountains along the scenic route 28 corridor, this lush 2-acre parcel offers endless potential for the nature lover, investor or visionary dreamers. Surrounded by a peaceful mountain ridgeline and a tranquil stream, this peaceful haven invites you to escape the bustle and reconnect with nature.Located in the

  Jeivan Castro Keller Williams Realty HV Nort

  Tbd New York 28, Oliverea, NY 12725
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  /27

  $399,000

  • 2 Beds
  • 1 Bath
  • 999 Sq Ft

  894 Woodland Valley Rd, Phoenicia, NY 12464

  Phoenicia-Woodland Valley HomeWelcome to Woodland Valley-Phoenicia, one of the most desirable locations in the beautiful Catskill Mountains. Built in 1985 this 2 BR, 1 BA, 999 SF house is set on a half acre parcel. There is a full basement, 108 SF rear deck, oversize shed/carport for yard work equipment/toys and a whole house backup generator. It's perfect as a full-time residence or a

  Alfred Peavy Ruth Gale Realty

  894 Woodland Valley Rd, Phoenicia, NY 12464
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  /33

  $779,000

  • Land
  • 8 Acres
  • $95,232 per Acre

  281 Dewitt Rd, Olivebridge, NY 12461

  ONE OF THE MOST SPECTACULAR WATERFALLS IN ULSTER COUNTY is front and center on this extremely rare and unusual land offering. The visual beauty of the waterfall, stream, cliffs and land is unparalleled. Calming audio of the waterfall and rushing Mettacahonts stream is 24/7 and year-round. Pulling into the circular driveway you are greeted by a master stone worker's hand-built raised garden bed,

  Hilton Purvis Coldwell Banker Village GreenN

  281 Dewitt Rd, Olivebridge, NY 12461
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  /31

  $239,000

  • 3 Beds
  • 1.5 Baths
  • 1,257 Sq Ft

  594 New York 42, Shandaken, NY 12480

  This beautiful modern completely redone home features 3 BRs, 1.5 BAs, a large open living room/kitchen/dining room and a new drilled well, new roof and a brand-new kitchen. Enter thru the 3-season game room into the light filled living space. Beautiful french doors open out to the level back yard overlooking the year-round stream featuring a firepit and barbecue area. Imagine all of those great

  Faye Storms Ruth Gale Realty

  594 New York 42, Shandaken, NY 12480
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  /30

  $1,175,000

  • 3 Beds
  • 2.5 Baths
  • 3,033 Sq Ft

  48 Hillside Dr, West Shokan, NY 12494

  Secluded Luxury Log Home with Spectacular Ashokan Reservoir Views + Additional ParcelWelcome to your dream retreat in the heart of the Catskills. Nestled on a private, serene hillside overlooking the stunning Ashokan Reservoir, this impeccably built 2006 log home combines rustic charm with modern luxury and energy efficiency.Crafted with top-of-the-line mechanicals and highly

  Mark Kanter BHHS HUDSON VALLEY PROP-WDST

  48 Hillside Dr, West Shokan, NY 12494
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  /38

  $1,182,750

  • 3 Beds
  • 2.5 Baths
  • 2,644 Sq Ft

  241 Silver Hollow Rd, Willow, NY 12495

  A whimsical compound just minutes to the village of Woodstock. On the two acre property you'll find a rushing stream and scenic pond, a three bedroom house, a cabin and a beautiful, modern barn that the current owners use for gatherings, yoga & music. The barn has been entirely rebuilt from the ground up so you'll find new electrical, a new heating & cooling system, local custom millwork, and

  Annabel Taylor Four Seasons Sothebys Intl

  241 Silver Hollow Rd, Willow, NY 12495
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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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  /47

  $525,000

  • 3 Beds
  • 3 Baths
  • 1,794 Sq Ft

  44 Dogwood Dr, Shokan, NY 12481

  Located in a highly desired part of the Catskill park! This home is perched on a hill with neighbors far enough away for your privacy, but close enough for security. Just minutes for the Ashokan reservoir, rail trail, skiing, hiking, fishing, Woodstock & Kingston. The home features a beautiful fireplace, pellet stove, hardwood floors, sauna, and lots of space to play or work from home. The large

  George Denise Keller Williams Realty HV Nort

  44 Dogwood Dr, Shokan, NY 12481
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  /7

  $110,000

  • Land
  • 2.60 Acres
  • $42,308 per Acre

  291 Acorn Hill Rd, Olivebridge, NY 12461

  Nestled off a private drive on Acorn Hill Road in the picturesque town of Olive, this 2.60-acre wooded lot offers the perfect blend of seclusion and natural beauty. Tucked away yet easily accessible via a deeded right of way, the property features stunning mountain views, rock outcroppings, and a peaceful, private setting surrounded by mature trees.Whether you're looking to build a serene weekend

  Paige McClintock Howard Hanna Rand Realty

  291 Acorn Hill Rd, Olivebridge, NY 12461
• 

  

  /38

  $650,000

  • 6 Beds
  • 3 Baths
  • 3,059 Sq Ft

  1441 County Road 2, Olivebridge, NY 12461

  Welcome to 1441 County Road 2 in Olivebridge, NY—a beautifully renovated 6-bedroom, 3-bathroom home nestled on 2.32 acres in the heart of the Catskills. This spacious 3,059 sq ft retreat features a brand-new kitchen, three cozy fireplaces, a sun-drenched great room, and a primary en suite on the main floor. With three bedrooms on each level, a full walk-out basement, and a large deck over the

  Nicholas Cuomo Keller Williams Realty

  1441 County Road 2, Olivebridge, NY 12461
• 

  

  /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
• 

  

  /24

  $349,000

  • 4 Beds
  • 2.5 Baths
  • 3,330 Sq Ft

  31 Lang Rd, West Shokan, NY 12494

  Bring your vision to this charming home in West Shokan, nestled amidst the Catskill Mountains. This spacious 4-bedroom, 2.5-bath home offers a generous 3,330 square feet of living space, situated on 1 acre of land. The charming 1 bed 1 bath accessory apartment holds significant potential for a guest/in-law suite or rental opportunity. This homes thoughtful floor plan seamlessly connects the

  Richard Vizzini Corcoran Country Living

  31 Lang Rd, West Shokan, NY 12494
• 

  

  /42

  $899,000

  • 4 Beds
  • 3 Baths
  • 1,456 Sq Ft

  40 Maxs Place, Kingston, NY 12401

  Tucked away on a quiet private road, this exceptional property offers a rare blend of privacy, style, and resort-like amenities—all just minutes from Woodstock and the best of the Catskills. At the heart of this beautifully updated home is a truly remarkable feature: a 40x60 indoor pool and sauna, creating an all-season sanctuary that's as perfect for quiet morning swims as it is for

  Leigh Wagner-Quintana Keller Williams Realty HV Nort

  40 Maxs Place, Kingston, NY 12401
• 

  

  /47

  $1,449,000

  • 3 Beds
  • 3 Baths
  • 2,327 Sq Ft

  263 California Quarry Rd, Woodstock, NY 12498

  Live above the clouds over Woodstock, the world's most famous little town. This remarkable contemporary home is just a few minutes from the bustling center of the village, in an absolutely tranquil setting! The views are breath-taking and expansive, and seen from almost every room. The Ashokan Reservoir, the entire Shawangunk Mountain Ridge (from Mohonk to Sam's Point) Ohayo Mountain, and, even

  Daniel Winn Halter Associates Realty

  263 California Quarry Rd, Woodstock, NY 12498
• 

  

  /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

Showing Results 81 - 120, Page 3 of 4