25

Houses for Sale in 12529

Section Image Section Image
  • /27

    $1,290,000 New Construction

    • 3 Beds
    • 3 Baths
    • 1,474 Sq Ft

    120 Pumpkin Hollow Rd N, Hillsdale, NY 12529

    A WORK OF ART IN HILLSDALETucked into the quiet beauty of Hillsdale, this stunning new build is anything but ordinary. Designed by award-winning architecture firm FORMA, this is their debut in the Hudson Valley. The home feels like a modern sculpture in nature—bold, thoughtful, and completely at ease in its surroundings.From the moment you arrive, there's a sense of calm and

    Agent Photo

    Steven Gray

    Compass Greater NY, LLC

    (518) 808-2502

    120 Pumpkin Hollow Rd N, Hillsdale, NY 12529
  • /44

    $1,295,000 Open Sat 12:30PM - 2:30PM

    • 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

    $1,575,000

    • 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
  • /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

    • 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
  • /39

    $1,195,000

    • 4 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 façade — framed with Doric columns. The

    MATTHEW CAREY Rouse + Co Real Estate, LLC

    11 Cold Water St, 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
  • /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
  • /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
  • /28

    $359,000

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft

    840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529

    As the original farmhouse on this road, this is the epitome of a charming south-facing Upstate home with an abundance of natural light and privacy. Cool in the summer and cozy in the winter, this home is a peaceful retreat all year long.Seated between the Hudson Valley and the Berkshires, the home is just two short miles from Copake Lake. A brief drive in any direction and you'll arrive at

    Theresa Westlake Copake Lake Realty Corp.

    840 Pumpkin Hollow Rd S Unit 1, 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
  • /24

    $875,000

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft

    407 Lakeview Rd, Craryville, NY 12521

    Copake Lake, New YorkA Lifetime of MemoriesNow is the time for the next generation. There is no shortage of views from this 2 BR + sleeping loft, 2 BA, 1574 sf log home. Be it the rocking chair porch or the 46' deck on the water this is the place to be for those famous ''Copake Lake Sunsets''. Copake Lake is ~425 acre motorboat lake strategically located equal-distance

    Lindsay Lebrecht Copake Lake Realty Corp.

    407 Lakeview Rd, Craryville, NY 12521
  • /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
  • /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 road.Set on a

    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
  • /18

    $274,900

    • 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
    • 3.5 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
  • /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
  • /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
  • /36

    $449,900

    • 2 Beds
    • 1 Bath
    • 1,012 Sq Ft

    69 SW Colony Rd, Hillsdale, NY 12529

    A Lake house in the country is perfect for those seeking a simple way of life. You'll feel like you're living in a storybook. Watch your story unfold before your eyes. Leona's Country Cottage is not your average cottage. It was architecturally designed and built to last many years to come. A new rebuild from the foundation up between 2020-2021 With all new requirements for efficiency and new code

    Michelle Ayala BHHS Hudson Valley Properties

    69 SW Colony 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
How to Buy a Home How to Finance a Home How to Sell a Home