Homes for Sale near Reginald Bennett Elementary School

• 

  

  

  /41

  $799,900

  Open Sat 11AM - 1PM $129K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,736 Sq Ft

  85 Kelder Hwy, Olivebridge, NY 12461

  Low-Tax Olive Haven Set on 6.5 quiet acres with the Shawangunk Ridge rising to the east, this beautifully renovated farmhouse feels like the place you've been looking for. The chef's kitchen includes a center island for prep and conversation, a dining table ready for long Sunday breakfasts, game night, or entertaining guests. The heart of the home is the great room, where picture windows flood

  

  Stefan Bolz

  Hudson Dwellings Realty

  85 Kelder Hwy, Olivebridge, NY 12461
• 

  Explore Reginald Bennett Elementary School

• 

  

  

  /38

  $565,000

  $24K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,839 Sq Ft

  10 Norman Rd, Shandaken, NY 12480

  A private Catskills retreat with backyard access to the Hunter-West Kill Wilderness, a small seasonal waterfall on the property, and Belleayre Mountain just 13 minutes away. Set on 3 peaceful acres in Shandaken, this 3 bedroom, 2.5 bath home offers the kind of four season lifestyle buyers come to the Catskills for hiking, skiing, snowshoeing, fishing, quiet mornings, and space to unwind. Inside,

  

  Teresa Falkowski

  Keller Williams Realty HV Nort

  10 Norman Rd, Shandaken, NY 12480
• 

  

  

  /40

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  5 Streamside Terrace, Woodstock, NY 12498

  OPEN HOUSE! Sunday 7/19 from 12:00-2:00! Woodstock Village living doesn't get much better than this. Perfectly positioned on a quiet no outlet street just moments from the heart of town, this beautifully renovated three-bedroom, two-bath home offers the rare opportunity to enjoy both nature and village life without compromise. Step inside to bright, sun-filled interiors and an open, welcoming

  

  Amy Lonas

  Coldwell Banker Village Green

  5 Streamside Terrace, Woodstock, NY 12498
• 

  

  

  /42

  $999,000

  $351K PRICE DROP

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

  23 Traver Hollow Rd, Boiceville, NY 12412

  Custom-Built Modern Home with Dramatic Mountain Views There are homes with views - and then there are homes built for the view. Affectionately known as Mountain Thyme, the mountain is not simply a backdrop but the defining presence of the property. From the moment you arrive, it rises dramatically into view, close enough to feel immersive, yet expansive enough to inspire. Designed to showcase the

  

  Leigh Bokser

  Compass Greater NY, LLC

  23 Traver Hollow Rd, Boiceville, NY 12412
• 

  

  

  /16

  $229,000

  • 0.5 Baths
  • 4,173 Sq Ft

  8663 New York 28, Big Indian, NY 12410

  

  Elizabeth McGuire

  Listing by Keller Williams Upstate NY Properties

  

  8663 New York 28, Big Indian, NY 12410
• 

  

  /42

  $574,999

  • 6 Beds
  • 2 Baths
  • 1,842 Sq Ft

  2 Mountain Valley Rd, Boiceville, NY 12412

  A rare and remarkable multi-family opportunity nestled in the heart of the Catskills — 2 Mountain Valley Road, Boiceville, New York presents two fully self-contained units, each delivering a level of space, privacy, and independence that is virtually unheard of in the multi-family market. Set against the stunning natural backdrop of Ulster County's Catskill Mountains, this 1,842 total square foot

  

  Richard Baxter

  Keller Williams Realty

  2 Mountain Valley Rd, Boiceville, NY 12412
• 

  

  /21

  $329,900

  $120K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 6,000 Sq Ft

  7284 New York 28, Shandaken, NY 12480

  This is a prime mixed-use property boasting 6000 square feet of potential nestled in a highly visible location, capturing the attention of passing traffic. Currently featuring a separate rental building and an owner's residence upstairs, this property offers a multifaceted investment opportunity. The commercial space downstairs presents a charming opportunity awaiting revitalization. With

  

  Teresa Falkowski

  Keller Williams Realty HV Nort

  7284 New York 28, Shandaken, NY 12480
• 

  

  /47

  $575,000

  • 6 Beds
  • 2 Baths
  • 1,842 Sq Ft

  2 Mountain Valley Rd, Boiceville, NY 12412

  A rare and remarkable multi-family opportunity nestled in the heart of the Catskills - 2 Mountain Valley Road, Boiceville, New York presents two fully self-contained units, each delivering a level of space, privacy, and independence that is virtually unheard of in the multi-family market. Set against the stunning natural backdrop of Ulster County's Catskill Mountains, this 1,842 total square foot

  

  Richard Baxter

  KELLER WILLIAMS REALTY

  2 Mountain Valley Rd, Boiceville, NY 12412
• 

  

  /11

  $749,900

  • Land
  • 27.9 Acres
  • $26,878 per Acre

  Tbd New York 28, Boiceville, NY 12412

  Incredible 27.9-acre development opportunity with mixed-use zoning and dual access from Route 28 and Upper Boiceville road. The front portion is zoned Highway Business with a 0.5-acre minimum, ideal for commercial use along this high-traffic corridor. The rear is zoned residential with a 1-acre minimum and could be subdivided for housing, a strip along the middle can go either way to be added to

  

  Teresa Falkowski

  Keller Williams Realty HV Nort

  Tbd New York 28, Boiceville, NY 12412
• 

  

  /48

  $1,349,000

  New Construction $150K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  99 W Shokan Heights Rd, West Shokan, NY 12494

  Tucked into the rolling landscape of West Shokan, where seasonal Catskill Mountain views emerge through the trees, this new construction contemporary home offers a rare blend of modern craftsmanship, warmth, and quiet luxury across 4.25 private acres. Surrounded by forest and designed to embrace its natural setting, the home captures the essence of elevated country living--where refined interiors

  Richard Vizzini Corcoran Country Living

  99 W Shokan Heights Rd, West Shokan, NY 12494
• 

  

  /51

  $899,000

  • 3 Beds
  • 4 Baths
  • 2,575 Sq Ft

  67 Private Road 24, Olivebridge, NY 12461

  Set at the end of a quiet private road, this custom-built cedar contemporary home is surrounded by nearly five acres of rolling lawn, mature woods, and sweeping mountain views. Thoughtfully positioned to embrace its natural setting, the property offers the kind of privacy that's increasingly difficult to find, while still being just minutes from the Ashokan Reservoir, hiking trails, local farm

  Richard Vizzini Corcoran Country Living

  67 Private Road 24, Olivebridge, NY 12461
• 

  

  /31

  $824,999

  • 2 Beds
  • 2 Baths
  • 1,910 Sq Ft

  18 Haberland Ln, Olivebridge, NY 12461

  There is something instantly comforting about this home. Warm, welcoming, and lovingly maintained, it offers the kind of easy living that never goes out of style. Whether gathering around the fireplace with friends, enjoying a quiet morning coffee, or unwinding after a long day, every space feels inviting, functional, and meant to be lived in. Set amidst peaceful natural surroundings with views

  Richard Vizzini Corcoran Country Living

  18 Haberland Ln, Olivebridge, NY 12461
• 

  

  /50

  $950,000

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  52 Brodhead Rd, West Shokan, NY 12494

  Where eagles fly and mountains kiss the sky, this beautifully maintained homestead showcases quality craftsmanship and thoughtful upgrades throughout. Whether you are an artisan, woodworker or equestrian, the well-equipped barn with Wi-Fi, telephone/paging system and electricity can easily meet your needs. The property features a thriving, fenced vegetable garden with separate well and shed

  Mary McKinney Coldwell Banker Village Green

  52 Brodhead Rd, West Shokan, NY 12494
• 

  

  /35

  $815,000

  • 2 Beds
  • 2 Baths
  • 2,856 Sq Ft

  376 Abbey Rd, Mount Tremper, NY 12457

  This classic contemporary retreat owned by the same family for over 2 decades is privately nestled on five picturesque acres along one of Woodstock's most coveted roads. Tucked away on a town-maintained dead-end lane, the property offers exceptional privacy and a true escape, all while remaining just minutes from the heart of Woodstock.Filled with natural light, this two-bedroom, two-bathroom

  Victoria Stent Coldwell Banker Village Green

  376 Abbey Rd, Mount Tremper, NY 12457
• 

  

  /33

  $599,000

  • 3 Beds
  • 1 Bath
  • 1,043 Sq Ft

  60 Muddy Brook Rd, Phoenicia, NY 12464

  Nestled in Woodland Valley, one of the Catskills' most sought-after private mountain enclaves, this charming country retreat offers a seamless blend of rustic character, modern updates, and natural beauty. Set on over 3 wooded acres and just a five-minute drive from the vibrant hamlet of Phoenicia, the property offers a peaceful sense of seclusion while keeping the region's most beloved

  Laurie Ylvisaker Coldwell Banker Village Green

  60 Muddy Brook Rd, Phoenicia, NY 12464
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  /34

  $855,000

  $44K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,795 Sq Ft

  4266 New York 212, Lake Hill, NY 12448

  Classic Woodstock Farmhouse with Pool, Valley Views & Storybook Grounds Come settle into the quintessential Woodstock lifestyle, a warm, welcoming farmhouse that invites both quiet mornings and spirited gatherings. The wide rocking-chair front porch sets the tone from the moment you arrive, the perfect place to linger with friends over a drink or lose yourself in a book through the long, golden

  Laurie Ylvisaker Coldwell Banker Village Green

  4266 New York 212, Lake Hill, NY 12448
• 

  

  /28

  $379,000

  $21K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 934 Sq Ft

  391 New York 375, West Hurley, NY 12491

  A compact, character-filled Hudson Valley retreat just minutes from Woodstock, this newly renovated Cape offers an unconventional two-level layout designed around charm, privacy, and relaxed country living. The 934 sq ft home features wood floors throughout, a cozy wood burning stove, with built-in dining area seating, and a stylish streamlined kitchen with subway tile, copper sink, stainless

  Ann Levine Coldwell Banker Village Green

  391 New York 375, West Hurley, NY 12491
• 

  

  /70

  $899,990

  $280K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,670 Sq Ft

  10 Kolb Rd, Boiceville, NY 12412

  Dear buyer, I want you to know the story of this house. My family bought it three years ago and we did a total renovation to all the bathrooms and kitchen with new appliances and tile and all new fixtures. We also changed the back of the house and opened it up with a huge dormer facing the mountain since before the main view was to the expansive side meadow. We thought this was going to be our

  Jasmine Jordaan Halter Associates Realty

  10 Kolb Rd, Boiceville, NY 12412
• 

  

  /50

  $2,000,000

  $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,671 Sq Ft

  53 Freeman Avery Rd, Olivebridge, NY 12461

  An architectural gem tucked away on 40 acres of pristine forest, this striking 3,671-square-foot residence is a stunning fusion of modern architecture and natural beauty. Crafted by the acclaimed Resolution: 4 Architecture, incorporating all of their most coveted features that converge in this divine mid century modern design. Travel down the tree lined driveway past a cascading waterfall to a

  Richard Vizzini Corcoran Country Living

  53 Freeman Avery Rd, Olivebridge, NY 12461
• 

  

  /53

  $1,995,000

  $105K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 5,199 Sq Ft

  250 Brodhead Rd, West Shokan, NY 12494

  A rare sanctuary where wellness, nature, and inspired country living converge across 17 idyllic acres. Framed by meadows, woodland, and a serene pond, the property offers a rare sense of escape--an immersive landscape designed as much for gathering and inspiration as for quiet retreat. At the heart of the grounds, the pond becomes a focal point for a lifestyle centered around wellness and

  Richard Vizzini Corcoran Country Living

  250 Brodhead Rd, West Shokan, NY 12494
• 

  

  /56

  $2,300,000

  • 3 Beds
  • 4 Baths
  • 2,613 Sq Ft

  56 Lauren Ct, Woodstock, NY 12498

  Exceptional 3 bedroom, 4 bath light-filled contemporary home offering refined nouvelle living set on over 4 private acres in Woodstock, NY. This home has had a complete interior high-end designer renovation that has been thoughtfully curated with sophisticated finishes and fine craftsmanship blending seamless luxury, comfort, and architectural elegance.A dramatic great room framed by soaring

  Amy Owens Coldwell Banker Village Green

  56 Lauren Ct, Woodstock, NY 12498
• 

  

  /62

  $949,000

  • 5 Beds
  • 7 Baths
  • 1,995 Sq Ft

  5355 New York 212, Mount Tremper, NY 12457

  A rare opportunity to acquire a hospitality property in the heart of the Catskills, Catskill Rose combines boutique lodging, a fully operational restaurant, and owner-occupant living quarters into a compelling live-work offering. Long recognized as a destination for travelers seeking an authentic Catskills experience, the property is thoughtfully designed to serve overnight guests, dining

  Richard Vizzini Corcoran Country Living

  5355 New York 212, Mount Tremper, NY 12457
• 

  

  /48

  $548,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,848 Sq Ft

  26-30 Fire House Rd, Big Indian, NY 12410

  Beautifully restored 1900 Victorian paired with a fully renovated, detached 2-bedroom apartment--a rare Catskills offering that seamlessly blends historic elegance, modern comfort, and exceptional income potential. Whether you're searching for a full-time residence, a weekend retreat, multigenerational living, or a property where rental income can help offset your mortgage, this remarkable

  Susan Lennon Coldwell Banker Timberland

  26-30 Fire House Rd, Big Indian, NY 12410
• 

  

  /44

  $3,325,000

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

  35 Van Wagner Rd, Willow, NY 12495

  More than a century in the making, and unlike anything else on the market, this extraordinary multi-residential estate began as a historic Hudson Valley farm before being thoughtfully transformed into a modern lifestyle retreat of remarkable scale and character. Over the years, musicians, entrepreneurs, and creative thinkers have called it home. Prior to that, it served as the Woodstock Farm

  Laurie Ylvisaker Coldwell Banker Village Green

  35 Van Wagner Rd, Willow, NY 12495
• 

  

  /69

  $1,100,000

  • 2 Beds
  • 6 Baths
  • 3,162 Sq Ft

  8479 Route 28, Big Indian, NY 12410

  Welcome to 8479 Route 28, Big Indian, NY. Big Indian is a scenic hamlet within the Town of Shandaken in Ulster County, NY, located in the heart of Catskill Park along State Route 28. The area is celebrated for its rugged wilderness and mountainous terrain. This parcel displays all that character: 172.1 +/- acres of diverse forest and mountainous terrain, blended with open and brushy fields

  Clint Carlson Whitetail Properties Real Estate

  8479 Route 28, Big Indian, NY 12410
• 

  

  /8

  $249,000

  • Land
  • 10 Acres
  • $24,900 per Acre

  4912 Ny-212, Willow, NY 12495

  Discover the opportunity to create your dream escape on this serene 10-acre parcel nestled in the quiet hamlet of Willow, NY. Tucked away in nature yet just a short drive from the vibrant village of Woodstock, this expansive property offers the perfect blend of privacy and proximity. Towering trees, dappled sunlight, and the calming sounds of nature create a peaceful setting for your future home,

  Richard Vizzini Corcoran Country Living

  4912 Ny-212, Willow, NY 12495
• 

  

  /15

  $10,299,000

  • Land
  • 686.6 Acres
  • $15,000 per Acre

  0 Dug Hill Rd Unit KEY909201, Hurley, NY 12443

  Now on the market: one of the most significant undeveloped land holdings in Ulster County, stretching from Kingston to the Ashokan Reservoir. Spanning over 686 acres, this rare offering is set in the ideal location: right in the heart of the Rondout Valley and just 90 minutes from New York City. Perfectly positioned between Kingston, Accord, and Saugerties/Woodstock. Surrounded by protected state

  Emily Haas-Godsil McRee Compass Greater NY, LLC

  0 Dug Hill Rd Unit KEY909201, Hurley, NY 12443
• 

  

  /26

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft

  11 Rose Mountain Rd, Big Indian, NY 12410

  ONLY A 5 MINUTE DRIVE TO BELLEAYRE MOUNTAIN SKI CENTER! This home is perfect for ski season and all year round. Cross over the gentle stream running alongside Rose Mountain Road and enter the setting of this cozy and well-maintained home, which offers a sense of privacy while still having a convenient location with easy maintenance. The interior has been carefully updated over time, and looks

  Joshua Slater The Catskill Dream Team

  11 Rose Mountain Rd, Big Indian, NY 12410
• 

  

  /50

  $1,350,000

  • 4 Beds
  • 4 Baths
  • 2,443 Sq Ft

  77 Lower Sahler Mill Rd, Olivebridge, NY 12461

  Tucked away on a sleepy country road, this gut-renovated and completely re-imagined 1930s retreat offers the perfect blend of privacy, natural beauty, and modern comfort. The main house is defined by a copious amount of windows and skylights which drenches the home in natural light and creates a perpetual connection to the outdoors. The kitchen boasts new appliances, soapstone counters and a

  Joseph Satto Compass Greater NY, LLC

  77 Lower Sahler Mill Rd, Olivebridge, NY 12461
• 

  

  /11

  $435,000

  $64K PRICE DROP

  • Land
  • 15.23 Acres
  • $28,562 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 has

  Laurie Osmond BHHS HUDSON VALLEY PROP-WDST

  Tbd Wardwell Ln, Woodstock, NY 12498
• 

  

  /14

  $295,000

  • Land
  • 41.73 Acres
  • $7,069 per Acre

  TBD NY-28 Route, Phoenicia, NY 12464

  An extraordinary 41.73-acre parcel along Route 28 in the heart of the Catskills, offering the ideal blend of accessibility, natural beauty, and development potential. This expansive tract features gently rolling topography with multiple elevated building sites surrounded by mature forest and mountain vistas. Whether you envision a private estate, compound, or small-scale subdivision, the

  Greg Berardi Berardi Realty

  TBD NY-28 Route, Phoenicia, NY 12464
• 

  

  /56

  $825,000

  • 8 Beds
  • 4.5 Baths
  • 2,623 Sq Ft

  7376 New York 28, Shandaken, NY 12480

  Take a look at this 8 bedroom, 4 full bathroom home with 4 floors of living space along with 1.77 fenced in acres. Completely renovated with modern fixtures and amenities, nothing to do but move in or rent immediately. The outside of the property features a front porch, Tesla charging station, spacious back deck with pergola and hot tub, large open yard and firepit area. Located right down the

  Jamie Sittner Find Advisors

  7376 New York 28, Shandaken, NY 12480
• 

  

  /32

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 2,157 Sq Ft

  4248 State Route 28, Boiceville, NY 12412

  Welcome to the most charming 1920s Arts & Crafts masterpiece. Whether you're plotting a full-time escape from the city or a weekend sanctuary, this light-soaked gem in the historic hamlet of Boiceville is the ultimate choice.Step through the center entry hall and prepare to swoon: beamed ceilings, historic charm, and a living room anchored by a fireplace with a cozy wood-burning stove.

  Carol Graham Corcoran Country Living

  4248 State Route 28, Boiceville, NY 12412
• 

  

  /5

  $67,500

  $8K PRICE DROP

  • Land
  • 14,374 Sq Ft
  • $204,545 per Acre

  1470 County Road 2, Olivebridge, NY 12461

  Looking to build a quaint, country escape on a low maintenance buildable lot? 1470 County Road 2 is the perfect location to do so! Equipped with a survey, BOH approval for a 2 bedroom home and zoning board of appeals approval from the local municipality, authorizes this lot as buildable for a 24x40 home. Bring your minimalistic 960 square foot country home to vision on this 0.44 acre lot in

  Zachary Jarvis BHHS Nutshell Realty

  1470 County Road 2, Olivebridge, NY 12461
• 

  

  /17

  $1,300,000

  • 3 Beds
  • 3.5 Baths
  • 2,822 Sq Ft

  60 Morgan Hill Rd, Hurley, NY 12443

  Modern design meets natural serenity in this exceptional new construction, set on 3.2 private wooded acres in Hurley and slated for completion by the fall of 2026. Offering over 2,800 square feet of thoughtfully designed living space, the home features 3 bedrooms, 3.5 baths, and two dedicated offices, blending contemporary architecture with everyday functionality. Just minutes from Woodstock,

  Baris Demirel Serhant LLC

  60 Morgan Hill Rd, Hurley, NY 12443
• 

  

  /50

  $2,499,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,462 Sq Ft

  760 Ohayo Mountain Rd, Glenford, NY 12433

  Six minutes from Woodstock and a world away from the typical upstate house, this new-construction courtyard home on 2.22 wooded acres in Glenford was designed by Amin Tadj Studio to near-Passive House standards. The kind of architectural home your architect wishes they lived in has been featured in Curbed, Dwell, Interior Design, Architect magazine, Upstate Diary, and more. Clad in thermally

  Arlena Armstrong Anatole House LLC

  760 Ohayo Mountain Rd, Glenford, NY 12433
• 

  

  /19

  $425,000

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  1906 County Road 3, Olivebridge, NY 12461

  This charming cottage in Olivebridge NY proves that great things really do come in small packages. Thoughtfully designed for easy living, it's the kind of home that lets you spend less time maintaining and more time enjoying everything the Hudson Valley has to offer.Inside, warm and inviting spaces feel instantly welcoming, while an airy loft provides the perfect spot for a home office,

  Jason Nadeau Compass Greater NY, LLC

  1906 County Road 3, Olivebridge, NY 12461
• 

  

  /17

  $99,900

  $50K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 800 Sq Ft

  244 Upper Samsonville Rd, Olivebridge, NY 12461

  Perfect 1 acre Catskill Mountain property with old mobile home in need of total rehabilitation. No well or septic on site. No existing heat source.

  Timothy Ayers Berardi Realty

  244 Upper Samsonville Rd, Olivebridge, NY 12461
• 

  

  /31

  $335,000

  • 3 Beds
  • 1 Bath
  • 1,272 Sq Ft

  42 Dixon Ave, Woodstock, NY 12498

  Situated on a large level lot and a quiet road near the heart of town. Some recent updates and fresh paint make this 4 brdm ranch home a terrific find in today's market. A covered porch in the front and rear allow for convenient outdoor entertainment. There is also plenty of off street parking and a detached shed for additional storage. Central location just minutes to Woodstock's vibrant music

  Rodney Batista Howard Hanna Rand Realty

  42 Dixon Ave, Woodstock, NY 12498
• 

  

  /35

  $599,900

  • 3 Beds
  • 3 Baths
  • 1,568 Sq Ft

  90 Jomar Ln, Olivebridge, NY 12461

  Welcome to 90 Jomar Lane, a beautifully maintained, move-in-ready ranch offering the perfect blend of comfort, space, and privacy. The main level features 1,568 square feet of thoughtfully designed living space, complemented by an additional 920 square feet in the fully finished basement, providing plenty of room for entertaining, recreation, a home office, or guest accommodations. This inviting

  Chris Weber BHHS HUDSON VALLEY PROP-NP

  90 Jomar Ln, Olivebridge, NY 12461

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