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Hillsdale, NY Homes for Sale with Water View

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  • /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
  • /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
  • /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

    $1,290,000

    • 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
  • /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
  • /44

    $725,000

    • 3 Beds
    • 2 Baths
    • 2,268 Sq Ft

    15 Tory Hill Rd, Hillsdale, NY 12529

    Nestled on a hillside just outside the vibrant hamlet of Hillsdale sits this exceptional 2007 Cape Cod cedar sided home. The views are simply one-of-a-kind, directly overlooking the Rheinstrom Hill Audubon Sanctuary and offering distant views reaching from the Taconic Range to the Catskill peaks. Energy saving features include a geo-thermal heating and cooling system, fully conditioned

    John Avenia Columbia County RE Specialist

    15 Tory Hill Rd, Hillsdale, NY 12529
  • /43

    $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

    Jennifer Harvey Compass Greater NY LLC

    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
  • /7

    $595,000

    • Land
    • 30 Acres
    • $19,833 per Acre

    0 Labranch Unit 20252234, Hillsdale, NY 12529

    Wonderful southern exposure on one of the most scenic byways in Columbia County. Large parcels and restrictive covenants on abutting land. High fields and ancient tree lines dotted with maples and old stone walls. Nice mix of open and wooded to tuck your home into the hedge row without another home in site. Distant views of Catamount Mountain. Close to Hawthorne Valley School and the Berkshires.

    Tracy Tassinari Gabel Real Estate

    0 Labranch Unit 20252234, 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
  • /18

    $2,999,000

    • Land
    • 242 Acres
    • $12,393 per Acre

    2 Dugway Rd, Austerlitz, NY 12017

    242 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

    Michael Tellerday Houlihan Lawrence, Inc.

    2 Dugway Rd, Austerlitz, NY 12017
  • /16

    $999,000

    • Land
    • 300.8 Acres
    • $3,321 per Acre

    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.

    Andrew Gates Houlihan Lawrence, Inc.

    25 Nobletown Rd, Hillsdale, NY 12529
  • /41

    $2,199,000

    • 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
  • /9

    $799,000

    • Land
    • 56.9 Acres
    • $14,042 per Acre

    3244 Cr 7, Hillsdale, NY 12529

    Beautiful 56+ private acres with views of Copake Lake and Catskill Mountain sunsets. After entering the gates, the forest lined driveway meanders to the sweet spot. There are plenty of options for a home site or 2! Be tucked away but so close to it all! Equidistant to Hudson, NY and Great Barrington, MA., there is so much the area has to offer. From Catamount Ski/Adventure Park to Tangelwood,

    Theresa Westlake Copake Lake Realty Corp.

    3244 Cr 7, Hillsdale, NY 12529
  • /19

    $3,999,000 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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