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Hillsdale, NY Homes for Sale with Garage

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  • /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
  • /25

    $1,575,000

    • 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
  • /46

    $2,450,000

    • 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
  • /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
  • /38

    $1,100,000

    • 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
  • /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
  • /37

    $1,195,000

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

    11 Cold Water St, Hillsdale, NY 12529

    This stately Greek Revival sits proudly on a generous village lot in the historic Hamlet of Hillsdale. Dating back to c.1848, the home boasts beautiful architectural proportions and details. Pilasters accent the exterior corners of the house and a front- and side-gabled roof add additional grandeur. Arrive via a front porch — running the full width of the facade — framed with Doric columns. The

    MATTHEW CAREY Rouse + Co Real Estate LLC

    11 Cold Water St, 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
  • /19

    $799,000

    • 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
  • /62

    $8,850,000

    • 4 Beds
    • 4.5 Baths
    • 6,438 Sq Ft

    890 Bald Mountain Rd, Austerlitz, NY 12017

    Welcome to The Bald Mountain Estate, the premier family compound in the Upper Hudson Valley. What sets this property apart as one of the most invaluable parcels in the area, is the land- unique, secluded, and beautifully rugged. Inside a gated area of large acreage estates, this 4 building architectural masterpiece property sits on 85 private acres, with multiple trails and an additional building

    Rachel Haley Houlihan Lawrence Inc.

    890 Bald Mountain Rd, Austerlitz, NY 12017
  • /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
  • /33

    $665,000

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

    2657 New York 23, Hillsdale, NY 12529

    Turnkey Historic Home, Fully Renovated, No Work NeededThis 1810 Greek Revival in Hillsdale has been completely gut-renovated, offering historic charm with none of the hassle. With rising construction costs and new U.S. tariffs driving up renovation expenses. This move-in-ready home is a smart, stress-free investment.All major systems are brand new: HVAC, plumbing, water filters,

    Pamela King-Belfor Four Seasons Sothebys Intl

    2657 New York 23, Hillsdale, NY 12529
  • /41

    $2,495,000

    • 3 Beds
    • 3 Baths
    • 2,720 Sq Ft

    250 Island Dr, Craryville, NY 12521

    Rarely available private gated island property, offered below market value.Sought after and water-front home on a private island in the middle of the only high-speed motor boat lake in Columbia County. A modern lake cottage and carriage house on 1.1 acres with four-season hot tub, large private dock and over 100ft of direct water frontage.The main house has 2 proper bedrooms and 2 full bathrooms,

    John Barbato Compass, Hillsdale

    250 Island Dr, Craryville, NY 12521
  • /59

    $1,195,000

    • 3 Beds
    • 2 Baths
    • 2,134 Sq Ft

    515 Turnpike, Hillsdale, NY 12529

    A secluded estate just outside Spencertown with panoramic Taconic views, Camp George blends rustic charm with modern comforts for effortless year-round living. At its heart, a warm, updated log cabin with lofted ceilings and sunlit interiors. A stunning 1,700 sq ft 1850s barn—relocated from the Adirondacks—features vaulted ceilings, wet bar, outdoor kitchen, and sleeping lofts. Swim in the 1-acre

    Joseph Briggs William Pitt Sotheby's

    515 Turnpike, Hillsdale, NY 12529
  • /19

    $4,250,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 2,720 Sq Ft

    250 Island Dr, Craryville, NY 12521

    New construction home on a private gated island with the possibility to customize further for 2026 completion.Exclusive location on a private island in the middle of the only water ski motor boat lake in Columbia County. A contemporary house on 1.1 acres with a large private dock and over 120ft of direct water frontage on Lake Copake. This beautiful home has 5 proper bedrooms (with the

    John Barbato Compass, Hillsdale

    250 Island Dr, Craryville, NY 12521
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