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Houses for Sale in 12529

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  • /39

    $895,000

    • 5 Beds
    • 3.5 Baths
    • 2,834 Sq Ft

    11 Cold Water St, Hillsdale, NY 12529

    This handsome Greek Revival sits on a quiet street occupying a generous village lot in the historic Hamlet of Hillsdale. Built around 1848, the home feels historic and fresh with plenty of room to spread out. A wide front porch with Doric columns welcomes you inside to a central foyer. To one side, a front parlor opens to a spacious dining room with elegant moldings. The kitchen is a highlight,

    MATTHEW CAREY Rouse + Co Real Estate, LLC

    11 Cold Water St, Hillsdale, NY 12529
  • /38

    $1,295,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    2955 New York 23, Hillsdale, NY 12529

    Historic Upstate NY Sanctuary - 8.7 Magical Acres in Hillsdale, NY - known for its scenic beauty and small-town charmEscape to your own private paradise on this enchanting 8.7-acre property featuring a charming 1820's cottage, pristine swimming pond with waterfall, and endless outdoor adventures. This secluded sanctuary offers the perfect blend of historic character and natural beauty, just

    Chris Getman Houlihan Lawrence Inc.

    2955 New York 23, Hillsdale, NY 12529
  • /44

    $1,295,000

    • 4 Beds
    • 3 Baths
    • 3,282 Sq Ft

    9960 New York 22, Hillsdale, NY 12529

    Step into a world of timeless charm and understated luxury with this impeccably restored 18th-century farmhouse, nestled on over 6 acres of landscaped lawns, flowering gardens, and river frontage along the trout-rich Roe-Jan Kill. The residence exudes warmth and authenticity, offering luminous interiors and inviting outdoor living spaces ideal for entertaining or quiet retreat.The grand

    Pamela King-Belfor Four Seasons Sotheby's Int.

    9960 New York 22, Hillsdale, NY 12529
  • /25

    $1,525,000

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

    83 Schmeichel Rd, Hillsdale, NY 12529

    A Home of Distinction -- there are two distinct sections of this 4+ BR, 4.5 BA, 2 office spaces, 3,666 sf home that is sited on 18.5 private acres. Wood-burning fireplace, 2 gas wood stoves. Pond with gazebo. The main section has 3 BR's, living room, family room, eat-in kitchen, access to the deck with Catamount views and an attached 2-car garage. The addition has a welcoming entrance, 1 BR.

    Lindsay Lebrecht Copake Lake Realty Corp.

    83 Schmeichel Rd, Hillsdale, NY 12529
  • /25

    $1,495,000

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    161 Stagecoach Rd, Hillsdale, NY 12529

    Architecture meets nature in Hillsdale. A fully secluded getaway at the end of a private dead-end road on 7.3 pristine acres. This sunny 3-bedroom, 2-1/2 bath house is inspired by Scandinavian design and features 3 outdoor decks, with views of a spring-fed stream, a crystal clear pond, and deep green woodlands. Central AC for summer days and a wood stove for snowy nights. An ideal layout

    Owen Davidson Brown Harris Stevens HV LLC

    161 Stagecoach Rd, Hillsdale, NY 12529
  • /35

    $1,650,000

    • 2 Beds
    • 3 Baths
    • 1,152 Sq Ft

    501 Birch St, Copake Lake, NY 12521

    Price Drop Alert: 145K decrease.Modern Country Living at Copake LakeWelcome to your dream getaway in the heart of Columbia County! Built in 2022, this beautifully crafted modern home offers comfort with a rustic touch perfectly nestled on 3.3 private acres just steps from stunning Copake Lake, a 410-acre freshwater gem.This thoughtfully designed home features an

    Gerard Meenagh The Meenagh Group Realty

    501 Birch St, Copake Lake, NY 12521
  • /38

    $1,100,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    110 Meadow Ln, Hillsdale, NY 12529

    Ultra-private dead-end lot overlooking Hillsdale, this extraordinary home offers some of the most breathtaking panoramic views in the entire Hudson Valley. Set on 11.9 totally private acres, the property is a rare combination of refined living and natural serenity, with a gentle stream meandering below and a charming footbridge crossing over—straight out of a storybook. There is even a pond with

    Michael Castellano Gilcrest Properties

    110 Meadow Ln, Hillsdale, NY 12529
  • /20

    $1,100,000

    • 2 Beds
    • 2 Baths
    • 1,419 Sq Ft

    75 Upper Hollow Rd, Hillsdale, NY 12529

    Nestled along a picturesque, secluded country dirt road--surrounded by a serene pond, a flowing creek, and wooded acreage--this charming 2 bedroom log cabin offers the perfect escape. The expansive property spans 193 acres, with 18 acres located outside the Columbia Land Conservancy and Forestry Program, allowing for reduced taxes and enhanced privacy.An additional structure on the

    Janet Kain The Kinderhook Group, Inc.

    75 Upper Hollow Rd, Hillsdale, NY 12529
  • /15

    $1,095,000

    • 4 Beds
    • 2.5 Baths
    • 1,344 Sq Ft

    25 Nobletown Rd, Hillsdale, NY 12529

    Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim

    Andrew Gates Houlihan Lawrence

    25 Nobletown Rd, Hillsdale, NY 12529
  • /36

    $650,000

    • 3 Beds
    • 2 Baths
    • 2,057 Sq Ft

    2657 New York 23, Hillsdale, NY 12529

    Proudly offering one of Hillsdale's most iconic and enduring homes—an exquisite piece of the Hudson Valley's heritage, perfectly positioned at the crossroads between Hudson, NY and Great Barrington, MA. Set in the vibrant and historic hamlet center, this timeless 3-bedroom, 2-bathroom residence is simply beautiful colonial charm.Thoughtfully renovated from top to bottom, the home retains its

    John Barbato Compass, Hillsdale

    2657 New York 23, Hillsdale, NY 12529
  • /38

    $795,000

    • 3 Beds
    • 3 Baths
    • 1,876 Sq Ft

    441 Overlook Dr, Hillsdale, NY 12529

    1940's stone cottage sited on 10 acres along the Green River. Main house has a lovely kitchen, with center island and soapstone counters, open to the dining area with French doors to screened porch. Stone fireplace in the living room with recent gas insert for ease of use. There is also a small den, full bath and laundry on this level. Upstairs there are two bedrooms, a hall bath and landing

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    441 Overlook Dr, Hillsdale, NY 12529
  • /8

    $399,000

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft

    251 Overlook Dr, Hillsdale, NY 12529

    Location location. Picturesque Overlook Dr in Hillsdale. Surrounded by large estates. The perfect early 1900s cottage on a gorgeous parcel. Lightly wooded with the potential for bigger views. Seasonal Berkshire views and stream that runs year round. Massive stone fireplace newly lined perfect for fall and winter nights. New enameled wood stove perfect for apres ski enjoyment. Close to Catamount

    Tracy Tassinari Gabel Real Estate

    251 Overlook Dr, Hillsdale, NY 12529
  • /9

    $220,000

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    10011 New York 22, Hillsdale, NY 12529

    Centrally located in Hillsdale, Columbia County, NY. Just about equal distance to Great Barrington, MA and Hudson, NY.This three bedroom, one bathroom, 1,000+ sf home offers a great level yard and a view of your own pond!The area is full of activities such as found at Catamount, the Harlem Valley Rail Trail (nothing motorized), Tanglewood, Copake Country Club, Copake Lake, organic farms, farmer

    Theresa Westlake Copake Lake Realty Corp.

    10011 New York 22, Hillsdale, NY 12529
  • /32

    $600,000

    • 3 Beds
    • 1 Bath
    • 1,303 Sq Ft

    16 Robin Rd, Craryville, NY 12521

    To say that the owner had vision when he purchased the home in 2018 is an understatement. The last listing said ''Bring your tools and fix this one up.'' The owner did just that. Removal of the interior walls, roof, exterior walls down to the frame & portions of the foundation occurred shortly after purchase. What occurred over the next two years was nothing short of miraculous. Brand new

    Mark Saxby Berkshire Hathaway HomeService

    16 Robin Rd, Craryville, NY 12521
  • /18

    $540,000

    • 2 Beds
    • 2 Baths
    • 1,493 Sq Ft

    2253 County Route 21, Hillsdale, NY 12529

    Introducing the Kinderhook Cabin, a well cared-for home where every detail has been thoughtfully considered and hand-finished by a master carpenter. Built in 2021, this ranch-style residence offers easy one-level living, a rustic-modern aesthetic and plenty of privacy, set on 5 acres along a beautiful winding country road between Kinderhook and Ghent. Step inside to a large entry hall

    Jeffries Blackerby Houlihan Lawrence Inc.

    2253 County Route 21, Hillsdale, NY 12529
  • /50

    $3,199,000

    • 4 Beds
    • 4.5 Baths
    • 4,635 Sq Ft

    211 Mitchell St, Hillsdale, NY 12529

    Elevate Your Lifestyle in Columbia CountyDiscover the pinnacle of modern luxury in this extraordinary Columbia County estate, set against the breathtaking backdrop of the Berkshire Hills and Catamount Mountains. Spanning over 10 meticulously landscaped acres, this architectural gem blends serene country living with sophisticated design.Step into a grand double-height foyer that

    Christopher Halliburton Beach & Bartolo Realtors

    211 Mitchell St, Hillsdale, NY 12529
  • /50

    $3,300,000

    • 4 Beds
    • 3 Baths
    • 2,825 Sq Ft

    88 Mac Brown Rd, Claverack-Red Mills, NY 12513

    Welcome to Mac Brown Waterhouse, a storied 119-acre estate set within a hidden valley offering complete seclusion and timeless beauty. The original 1830s farmhouse is tucked away at the end of a private lane in Claverack, NY, where the road terminates in a round gravel driveway anchored by the property’s original stone well. Two large ponds grace the land, one directly in front of the house that

    Anthony D'Argenzio Houlihan Lawrence, Inc

    88 Mac Brown Rd, Claverack-Red Mills, NY 12513
  • /85

    $3,995,000

    • 4 Beds
    • 5 Baths
    • 6,442 Sq Ft

    350 Tory Hill Farm Rd, Hillsdale, NY 12529

    Peace and seclusion on a private road.Pass through a stone gate and travel a long, winding driveway to reach this exceptional property, quietly nestled into the mountainside. The setting is serene, with only the sounds of birds and the breeze in the air. From its elevated position, the home offers uninterrupted, layered views of the Berkshire mountains stretching far beyond to distant

    John Barbato Compass, Hillsdale

    350 Tory Hill Farm Rd, Hillsdale, NY 12529
  • /38

    $649,000

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    47 Cherokee Dr, Hillsdale, NY 12529

    Kick off your flip flops and enjoy lake life. Tucked above Copake Lake in Hillsdale, NY, Lakelight is a freshly renovated chalet with deeded lake access, two sunny decks, and something most lake houses don’t offer: privacy. This isn’t a shoulder-to-shoulder shoreline setup. You’ve got space, trees, light, and breathing room—with the water just two minutes away down a quiet private

    Arlena Armstrong Anatole House LLC

    47 Cherokee Dr, Hillsdale, NY 12529
  • /19

    $347,000

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    81 SW Sw Colony Rd, Hillsdale, NY 12529

    Welcome to Copake Lake!! Sweet two-bedroom, one bath cottage, eat in kitchen, views of the lake from living room and one of the two bedrooms, nice big yard to enjoy outdoor fun. All appliances included. PLUS (As per Seller) water rights along that 20-foot stretch, a buyer may be able to agree with others in the area to extend the existing dock, which could be up to 60 feet into the lake!

    Margaret Bower Avenia Columbia County RE Specialist

    81 SW Sw Colony Rd, Hillsdale, NY 12529
  • /24

    $845,000

    • 6 Beds
    • 2 Baths
    • 2,998 Sq Ft

    60 Anthony St, Hillsdale, NY 12529

    Price reduction.1800s farm house. Just waiting for some TLC. This property consists of the main farm house. one very large barn. Addtional 3 out building. One of the back building contains an attractive apartment.The property butts up to the Harlem Valley Rail Trail. Walking distant to the Hamlet of Hillsdale. Including the Roe Jan Brewing Co. IGA, The Hillsdale House, The town park. Less then 5

    Gerard Meenagh The Meenagh Group Realty

    60 Anthony St, Hillsdale, NY 12529
  • /46

    $2,250,000

    • 2 Beds
    • 2 Baths
    • 2,755 Sq Ft

    292 White Hill Ln, Hillsdale, NY 12529

    Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side brings in the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    292 White Hill Ln, Hillsdale, NY 12529
  • /19

    $249,900

    • 2 Beds
    • 2 Baths
    • 794 Sq Ft

    2227 County Route 21, Hillsdale, NY 12529

    Tucked away on over 17 serene, subdividable acres in the Town of Kinderhook, this rare offering includes a half-finished 2-bedroom home (a shell awaiting your vision) with a brand-new raised-bed septic system and drilled well (newer pump) & new pressure tank already in place. With frontage on two quiet country roads; County Route 21 and Fowler Lake Rd. this land is a mix of old stone walls,

    Michael Castellano Gilcrest Properties

    2227 County Route 21, Hillsdale, NY 12529
  • /45

    $1,268,500

    • 2 Beds
    • 2 Baths
    • 1,700 Sq Ft

    401 Collins Street Stop 11, Hillsdale, NY 12529

    A Visionary Masterpiece in Columbia County Redefining Country Living. Tucked away on over four serene, wooded acres along one of Columbia County's most coveted roads, this extraordinary 1,700-square-foot contemporary barn home is an architectural work of art a one-of-a-kind residence conceived and crafted by acclaimed designer Angela Patterson. Marrying bold architectural innovation with the

    DeWayne A. Powell William Pitt Sotheby's Int'l

    401 Collins Street Stop 11, Hillsdale, NY 12529
  • /16

    $725,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    30 Ridge Ln, Hillsdale, NY 12529

    Ridge Lane in Hillsdale is the perfect country retreat. Set on 7+ acres on a quiet dead end road. This newly built farmhouse captures the charm and solitude that make Hillsdale so desired. Come in to the mudroom, kick off your shoes and enjoy the space of a real country kitchen. The open living space flows easily to the dining area and living room or out to the deck to enjoy the blue sky. An

    Emma French Gabel Real Estate

    30 Ridge Ln, Hillsdale, NY 12529
  • /40

    $2,995,000

    • 5 Beds
    • 5.5 Baths
    • 7,200 Sq Ft

    35 Harlemville Rd, Hillsdale, NY 12529

    Where Norman charm meets Hudson Valley splendor, "Dragonfly" stands as a fine example of country living - a rare 130-acre estate that marries grand European sophistication with the pastoral beauty of Claverack. Just twenty minutes from the cultural centers of Hudson and the Berkshires, this property strikes a balance between secluded sanctuary and connected countryside living.A winding private

    Chris Getman Houlihan Lawrence Inc.

    35 Harlemville Rd, Hillsdale, NY 12529
  • /31

    $495,000

    • 2 Beds
    • 2 Baths
    • 1,832 Sq Ft

    117 Spring St, Craryville, NY 12521

    A Modern Retreat with Rustic Charm at the End of a Quiet Road.Nestled at the very end of a peaceful country road, this contemporary home with rustic flair offers the perfect blend of modern comfort and natural warmth. Privately set and surrounded by nature, this home is a tranquil haven ideal for year-round living or a weekend getaway.Step inside to discover thoughtfully crafted

    Maria DiSalvo Coldwell Banker Prime

    117 Spring St, Craryville, NY 12521
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