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Homes for Sale near Reginald Bennett Elementary School

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  • /39

    $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,

    Agent Photo

    Teresa Falkowski

    Keller Williams Realty HV Nort

    10 Norman Rd, Shandaken, NY 12480
  • /42

    $569,999

    $5K PRICE DROP
    • 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 hard to find in the multi-family market.Set against the stunning natural backdrop of Ulster County’s Catskill Mountains, this 1,842 total square foot

    Agent Photo

    Richard Baxter

    Keller Williams Realty

    2 Mountain Valley Rd, Boiceville, NY 12412
  • /26

    $299,900

    $150K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 6,000 Sq Ft

    7284 New York 28, Shandaken, NY 12480

    A rare opportunity for an entrepreneur, investor, or buyer with the vision to revive a historic Catskills property and give it new life. Prominently positioned along high-traffic Route 28 on the way to Belleayre Mountain and just minutes from Phoenicia, this commercially zoned property offers excellent visibility and a wide range of possibilities.The building requires significant work and

    Agent Photo

    Teresa Falkowski

    Keller Williams Realty HV Nort

    7284 New York 28, Shandaken, NY 12480
  • /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

    Agent Photo

    Teresa Falkowski

    Keller Williams Realty HV Nort

    Tbd New York 28, Boiceville, NY 12412
  • /30

    $900,000

    • 5 Beds
    • 2 Baths
    • 1,824 Sq Ft

    436 Dug Hill Rd, Hurley, NY 12443

    The Dug Hill Rd House A family legacy, offered for the first time. Some homes come to market. This one comes to light for the very first. Built in 1969 by the current owner's father, this home has been loved, cared for, and privately passed down through one family. Now it's ready for a new story to begin. Tucked into 13.9 private acres and bordered by over 300 acres of protected state land on two

    Agent Photo

    Mark McAlpine

    Compass Greater New York, LLC

    436 Dug Hill Rd, Hurley, NY 12443
  • /53

    $1,850,000

    $250K 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
  • /54

    $539,000

    $29K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,848 Sq Ft

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

    This exquisite 1900 Victorian is paired with an INCOME producing detached renovated apartment. The total living area for the 2 dwellings is 2657 SF. These dwellings sit on 0.78 acres of peaceful land with a small scenic stream in the rear surrounded by a mountain backdrop.HIGHLIGHTS of the 1900 Victorian Home: ONCE you step into this timeless masterpiece, you are bound to become aware of the

    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
  • /61

    $799,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,889 Sq Ft

    125 Stone Rd, West Hurley, NY 12491

    Stone ledges and breathtaking vistas are yours in this lovingly maintained custom log home created specifically for those who are searching for privacy, fresh air and peace of mind. Enjoy panoramic views off the wrap around rear deck overlooking a patchwork quilt of acres of state and town protected land. Perfectly situated off a quiet, country road just one mile from the Ashokan Reservoir and 10

    Mary McKinney Coldwell Banker Village GreenK

    125 Stone Rd, West Hurley, NY 12491
  • /52

    $849,000

    $50K PRICE DROP
    • 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
  • /32

    $775,000

    $50K PRICE DROP
    • 3 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

    $899,900

    $50K PRICE DROP
    • 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. The property also includes a 1,104 square foot barn that is perfect for equestrians or a studio, workshop, artisan/woodworker or equipment storage. Two overhead garage doors, extended wi-fi service, telephone/paging system and electricity can

    Mary McKinney Coldwell Banker Village Green

    52 Brodhead Rd, West Shokan, NY 12494
  • /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
  • /69

    $999,999

    $100K PRICE DROP
    • 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
  • /13

    $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
  • /31

    $499,000

    $26K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,502 Sq Ft

    18 Elting Ln, Bearsville, NY 12409

    Come and see this cute-as-a-button, circa 1950 brick cape on Elting Lane, one of Woodstock's most enchanting roads! This easy-to-manage home on just shy of an acre, boasts woodland surroundings plus seasonal meadow and mountain views and fruit trees.The main floor features a light flooded living room with fireplace, an efficient kitchen with adjacent dining area with double glass doors

    Pamela Hoveling Halter Associates Realty

    18 Elting Ln, Bearsville, NY 12409
  • /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
  • /33

    $749,000

    $50K PRICE DROP
    • 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

    $65,000

    $10K PRICE DROP
    • Land
    • 14,374 Sq Ft
    • $196,970 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
  • /13

    $599,000

    • Land
    • 7.18 Acres
    • $83,426 per Acre

    Lot 2 11 Marion's Way, Woodstock, NY 12498

    A once-in-a-generation opportunity to create your dream home in the heart of Woodstock, the coolest small town in America. Nestled on 7 shovel-ready acres just moments from the vibrant village center, this exceptional property offers the perfect balance of privacy, natural beauty, and convenience. Steeped in local history, the land is one of the last remaining vacant parcels from an historic

    Joel Craig Coldwell Banker Village Green

    Lot 2 11 Marion's Way, Woodstock, NY 12498
  • /19

    $399,000

    $26K PRICE DROP
    • 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
  • /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
  • /33

    $779,000

    $46K PRICE DROP
    • Land
    • 8.18 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,

    Anne Hilton Purvis Coldwell Banker Village GreenN

    281 Dewitt Rd, Olivebridge, NY 12461
  • /2

    $80,000

    $100K PRICE DROP
    • Land
    • 5.61 Acres
    • $14,260 per Acre

    00 Fischer Ln, Olive, NY 12461

    Location location location! This beautifully wooded lot is located on aprivate road with close proximity to Woodstock. Build your dream home or use it for your privacy buffer. and combine it with Kelder and 55 G Fischer for a total of 20 acres.

    Adrienne Volpe KW Mid-Hudson

    00 Fischer Ln, Olive, NY 12461
  • /2

    $24,000

    • Land
    • 16,552 Sq Ft
    • $63,158 per Acre

    Lot 48 Garfield Rd, Shandaken, NY 12464

    Lot 48 on Garfield Road sits quietly where the Catskills stop feeling like a destination and start feeling like home. Zoned R1.5, this parcel offers a rare balance of flexibility and restraint—enough land to build comfortably while preserving the sense of space and privacy that draws people to Shandaken in the first place. From the road, the property feels understated, but once you step onto the

    Thomas Santore Coldwell Banker Realty

    Lot 48 Garfield Rd, Shandaken, NY 12464
  • /31

    $647,000

    $112K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    48 Mountain View Ave, Woodstock, NY 12498

    For your client searching for the idyllic cottage on a charming county road, don't overlook Mountain View Ave. This peaceful location is well set back from the road yet walking distance to the center of vibrant Woodstock with all the charming shops, cafes and art galleries and music venues our town is known for. This charming cottage with Craftsman style features was built in 1923. Renovated

    Barbara Ellman BHHS HUDSON VALLEY PROP-WDST

    48 Mountain View Ave, Woodstock, NY 12498
  • /47

    $899,990

    $80K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,690 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 Inc.

    10 Kolb Rd, Boiceville, NY 12412
  • /42

    $815,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,368 Sq Ft

    285 Morgan Hill Rd, Hurley, NY 12443

    Welcome to this beautifully renovated country retreat. A turnkey property with an inground Kidney shaped pool, detached 1,300 sq ft 2 bedroom 1 bath cottage and a generous workshop. The main home showcases a modern eat in kitchen with stainless steel appliances, quartz counters, stone floors, abundant wood cabinetry and a floor to ceiling pantry. Light filled living and dining rooms both with

    Sharon Farley Corcoran Country Living

    285 Morgan Hill Rd, Hurley, NY 12443
  • /37

    $1,875,000

    • 3 Beds
    • 2 Baths
    • 2,800 Sq Ft

    101 Bristol Hill Rd, Glenford, NY 12433

    Massive style with minimal expenses: This stunning 2,800-square-foot one-level home, designed by an architect for his own family, delivers cutting-edge luxury in a sought-after neighborhood just minutes from Woodstock and the Ashokan Reservoir. Set on 1.5 wooded acres, the house delivers a seamless blend of big-impact, light-filled interior spaces with a beautiful and secluded wooded setting,

    Hayes Clement Compass Greater New York, LLC

    101 Bristol Hill Rd, Glenford, NY 12433
  • /50

    $595,000

    $54K PRICE DROP
    • 7 Beds
    • 5 Baths
    • 3,968 Sq Ft

    8643 New York 28, Big Indian, NY 12410

    Welcome to The Gather House located at 8643 New York 28 in Big Indian - a Four-Season Mountain Retreat in the Heart of the Catskills.There's a certain kind of quiet you only find in the Catskills - the kind that settles in your shoulders, slows your breathing, and reminds you that life can be simpler, softer, more intentional.As Route 28 winds through the valley, the mountains

    Matthew Horton Coldwell Banker Village Green

    8643 New York 28, Big Indian, NY 12410
  • /32

    $749,000

    • 4 Beds
    • 2 Baths
    • 2,412 Sq Ft

    325 Morgan Hill Rd, Hurley, NY 12443

    Tucked into more than 6.5 tranquil acres in low-tax Hurley, this cedar-sided Cape offers warmth, privacy, and a connection to its natural surroundings. Inside you will find well proportioned spaces, flowing from an ample dining room and open kitchen to a cozy living room warmed by a woodstove. The beautiful custom kitchen features solid wood cabinetry, Wolf and Subzero appliances, and striking

    Sarah Finch The Kinderhook Group, Inc.

    325 Morgan Hill Rd, Hurley, NY 12443
  • /49

    $1,295,000

    $200K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,731 Sq Ft

    41 Wittenberg Rd, Bearsville, NY 12409

    Hidden among the trees and just seven minutes from the center of Woodstock, this 1970s contemporary feels like a private creative compound, untouched in all the right ways.Set on 2 wooded acres with the Sawkill Creek at the rear of the property, the home unfolds through a series of unexpected spaces and strong architectural moments. A dramatic sunken living room anchors the house,

    Michelle Bergkamp William Pitt Sotheby's Interna

    41 Wittenberg Rd, Bearsville, NY 12409
  • /28

    $549,000

    • 3 Beds
    • 2 Baths
    • 2,112 Sq Ft

    22 Park Rd, Chichester, NY 12416

    Own a piece of local history in this lovely 1920's three-bedroom Cape-style home on a .93 acre lot abutting protected state land. It's perfect for nature lovers! Only 2 miles to the town of Phoenicia. This home offers a large kitchen with a customized granite island, an updated master bath, newly added living room bay window, Navian tankless water heater, washer, dryer, refrigerator, and detached

    Carol Graham Corcoran Country Living

    22 Park Rd, Chichester, NY 12416
  • /49

    $475,000

    • 4 Beds
    • 3.5 Baths
    • 2,636 Sq Ft

    6283-6285 New York 28, Phoenicia, NY 12464

    Some homes simply have a way of growing with the people who live in them.Located less than two miles from the charmed Village of Phoenicia, this one-of-a-kind property combines a spacious multi-level home, an independent lower-level apartment and a former legal commercial space - a rare combination that's becoming increasingly difficult to find in the Catskills.Quality

    Amy Rosen Ruth Gale Realty

    6283-6285 New York 28, Phoenicia, NY 12464
  • /26

    $399,000

    • 1,000 Sq Ft

    281 Cold Brook Rd, Bearsville, NY 12409

    There are homes that ask you to compromise, and then there are homes that ask you to dream.Set against a backdrop of sweeping mountain views, this is a rare opportunity to create something that’s unmistakably yours. The hardest work has already been done. What’s left is the part that reflects your style, your vision, and the way you want to live.Picture slow mornings with coffee

    Ron Knowles Century 21 Alliance Rlty Group

    281 Cold Brook Rd, Bearsville, NY 12409
  • /7

    $149,000

    29 Reservoir Rd, Shokan, NY 12481

    Property has a 3BR, 1bath house which needs complete Renovation or Demolition. BEING SOLD AS-IS This is an ideal quiet location just a few lots off route 28 and walkable to The Asokan Reservoir. Minutes from all services and shopping. Kingston and Woodstock are near-by. Onteora school system right down the road. Rail Trail around the corner. Live in a country location and work in Kingston with

    Faye Storms Ruth Gale Realty

    29 Reservoir Rd, Shokan, NY 12481

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