49

Homes for Sale in 12529

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  • /44

    $1,475,000 New Construction

    • 3 Beds
    • 3 Baths
    • 2,350 Sq Ft

    501 Birch St, Craryville, NY 12521

    Newly constructed and thoughtfully designed, this home is ideally located within the Copake Lake community-Columbia County's only high-speed motorboat lake-and built by one of the area's most respected contractors. The property reflects quality craftsmanship throughout.The home offers 3 bedrooms and 3 full bathrooms, including two primary suites on the main level. The third bedroom is on the

    John Barbato Compass, Hillsdale

    501 Birch St, Craryville, NY 12521
  • /40

    $964,000

    • 3 Beds
    • 1.5 Baths
    • 1,293 Sq Ft

    44 SW Colony Rd, Hillsdale, NY 12529

    Set on the shores of Copake Lake, this charming waterfront home blends classic lake character with thoughtful modern updates. Offering three bedrooms and 1.5 baths, the home features a bright open kitchen, living, and dining area designed for easy lake living and entertaining. Recent renovations, including HVAC, septic system, and expansion to main floor, bring fresh style and comfort while

    Austin Urban Venture Fox Realty Group

    44 SW Colony Rd, Hillsdale, NY 12529
  • /37

    $799,000 Open House 5/23

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

    407 Lakeview Rd, Craryville, NY 12521

    A rare year-round Lakefront Opportunity on Copake Lake. Just 2 Hours from NYC -Charming Log Home with Private Dock and deck. Swim, boat, ski, and relax year-round at this lakefront home.Ideally located between Hudson and Great Barrington in the heart of the Hudson Valley-Berkshires region. Turn-key four-season log home with sweeping lake views, a 46-foot private waterfront deck and

    Maria DiSalvo Coldwell Banker Prime

    407 Lakeview Rd, Craryville, NY 12521
  • /28

    $1,275,000

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

    401 Collins St, Hillsdale, NY 12529

    Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County’s most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a

    Pamela King-Belfor Four Seasons Sothebys Intl

    401 Collins St, Hillsdale, NY 12529
  • /28

    $1,275,000

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

    401 Collins St Unit Stop 11, Hillsdale, NY 12529

    Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County's most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a

    Pamela King-Belfor Four Seasons Sotheby's Int.

    401 Collins St Unit Stop 11, Hillsdale, NY 12529
  • /28

    $810,000

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

    60 Anthony St, Hillsdale, NY 12529

    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 min ride to

    Gerard Meenagh The Meenagh Group Realty

    60 Anthony St, Hillsdale, NY 12529
  • /44

    $1,275,000

    • 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
  • /22

    $1,150,000

    • 3 Beds
    • 3 Baths
    • 2,880 Sq Ft

    143 Julianna Dr, Copake, NY 12516

    Set in the sought-after Copake Lake community, this custom Lindal home offers a compelling blend of modern post-and-beam architecture, curated interiors, and coveted lake access with an HOA boat slip—all set on 3.4 private acres with seasonal lake views and low-maintenance landscaping. Defined by its signature cedar construction, soaring ceilings, and expansive walls of glass, the home is filled

    TRACY DOBER Rouse + Co Real Estate LLC

    143 Julianna Dr, Copake, NY 12516
  • /17

    $999,000

    • 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, INC

    25 Nobletown Rd, Hillsdale, NY 12529
  • /25

    $325,000

    • 1 Bed
    • 1 Bath
    • 656 Sq Ft

    127 Hillside Dr, Copake Lake, NY 12521

    For those seeking a secluded cabin in the woods, this charming 1940s log home offers both privacy and the added benefit of deeded lake rights to Copake Lake. The main level features an open-concept layout, including a living room, dining area, kitchen, bedroom, and full bath. A thoughtful custom detail--a pull-down kitchen table--enhances both functionality and character. The walk-out lower level

    Lindsay Lebrecht Copake Lake Realty Corp.

    127 Hillside Dr, Copake Lake, NY 12521
  • /13

    $1,100,000

    • Land
    • 9.01 Acres
    • $122,087 per Acre

    197 Lk Rdg Ln, Copake Lake, NY 12521

    A special opportunity to enjoy lake living within a uniquely private setting. The Ridge at Copake Lake is a gated private road of 11 ready-to-build lots nestled in the lush landscape of an untouched mountain top. Each designated building site has been artfully tailored to visually isolate one home from another. The 9+ acres of Lot 8 embrace direct views of the Catskill mountains to the west, and

    John Barbato Compass, Hillsdale

    197 Lk Rdg Ln, Copake Lake, NY 12521
  • /6

    $175,000

    • Land
    • 33.31 Acres
    • $5,254 per Acre

    50 Dugway Rd, Hillsdale, NY 12529

    Create Your Own Vision.Escape to 33.31 acres of untouched beauty in Columbia County, NY, and close to Great Barrington, MA. This stunning parcel of wooded land offers complete privacy with no neighbors in sight just you and the tranquility of nature. Imagine the possibilities as you explore the lush, wooded landscape teeming with wildlife. Over 1,677 feet of road frontage, and an old roadway that

    Jeffrey McKinney Beach & Bartolo Realtors

    50 Dugway Rd, Hillsdale, NY 12529
  • /32

    $339,000

    • 3 Beds
    • 1 Bath
    • 1,470 Sq Ft

    9539 New York 22, Hillsdale, NY 12529

    Newly Renovated Hillsdale Gem! Welcome to this beautifully renovated 3-bedroom home in the heart of Hillsdale. Thoughtfully updated with today's buyer in mind, this residence blends modern comfort with timeless charm. Inside, you'll find a bright, welcoming kitchen featuring quartz countertops, high-end vinyl plank flooring, and a suite of updated appliances designed for both style and

    Marie Rodriguez Red Apple Realty

    9539 New York 22, Hillsdale, NY 12529
  • /24

    $615,000

    • 3 Beds
    • 1.5 Baths
    • 864 Sq Ft

    5 Adams Dr, Hillsdale, NY 12529

    This charming 3 BR, 1.5 Bath cottage is located across the street from Copake Lake and the HOA Waterfront, Marina and Beach area. Unlike some of the other homes in the area, the house is situated on an elevated, oversized lot with a big front yard and spectacular sunset views. Inside, the house features real wood paneling and a wood burning stove in the living room, a cozy kitchen with a new gas

    Russ Stein Compass Greater NY LLC

    5 Adams Dr, Hillsdale, NY 12529
  • /23

    $419,000

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

    16 Robin Rd, Craryville, NY 12521

    JUST IN TIME FOR SUMMER AT COPAKE LAKE!This home has undergone a complete transformation. Much of the structure was taken down to the frame and rebuilt with precision, resulting in a modern, energy-efficient retreat designed for comfort, style, and long-term durability.Today, the home offers new interior and exterior walls, roof, plumbing, electrical, insulation, and high-efficiency

    Blanche Mackey Copake Lake Realty Corp.

    16 Robin Rd, Craryville, NY 12521
  • /6

    $3,490,000

    • 3 Beds
    • 4 Baths
    • 7,571 Sq Ft

    351 Lakeview Rd, Craryville, NY 12521

    Welcome to Mickey's Marina, a rare waterfront opportunity located at 351 Lakeview Road. Set along the shoreline with beautiful lake views, this unique property blends recreation, income potential, and lifestyle in one exceptional offering. The marina features direct water access with multiple boat slips, making it an ideal destination for boating enthusiasts and seasonal visitors alike. With its

    Austin Urban Venture Fox Realty Group

    351 Lakeview Rd, Craryville, NY 12521
  • /7

    $259,000

    • 3 Beds
    • 3 Baths
    • 2,304 Sq Ft

    9249 Route 22 Rd, Hillsdale, NY 12516

    Mixed Residential/Commercial building, with 3 rentable spaces. Current RR 30,540. One side of building has commercial reception area down and 1BR apartment above. Rental 1395/m. Other side is studio apartment up and storefront down. Can be rented to same party for commercial downstairs. Current rental is 795 + 550. Ideal for live/work. Building in excellent condition, roof less than 5 years old.

    David Birch Barns & Farms Realty, LLC

    9249 Route 22 Rd, Hillsdale, NY 12516
  • /20

    $5,100,000

    • Land
    • 517 Acres
    • $9,865 per Acre

    4 W Hill Rd, Austerlitz, NY 12017

    517 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.

    4 W Hill Rd, Austerlitz, NY 12017
  • /13

    $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
  • /21

    $349,900

    • 3 Beds
    • 1 Bath
    • 1,381 Sq Ft

    9659 New York 22, Hillsdale, NY 12529

    Come see the new me!. I've had a face lift and you are sure to enjoy the gleaming hardwood floors and the updated kitchen with granite counters and new appliances. It's one level of easy living, and offers many wonderful features. Enjoy the spacious living room framed by a fireplace, or the cozy den which has one as well..The middle bedroom features sliders that open onto a deck, great to enjoy

    Tammy Molinski Coldwell Banker Advisor Realty

    9659 New York 22, Hillsdale, NY 12529
  • /15

    $2,999,000

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

    00 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.

    00 Dugway Rd, Austerlitz, NY 12017
  • /19

    $850,000

    • Land
    • 150 Acres
    • $5,667 per Acre

    400 Overlook Dr, Hillsdale, NY 12529

    Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

    MATTHEW CAREY Rouse + Co Real Estate

    400 Overlook Dr, Hillsdale, NY 12529
  • /43

    $2,195,000

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

    292 White Hill Rd, 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 captures 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

    Jennifer Harvey Compass Greater NY LLC

    292 White Hill Rd, Hillsdale, NY 12529
  • /31

    $1,695,000

    • Land
    • 127.1 Acres
    • $13,336 per Acre

    0 Mitchell St Unit 20251360, Hillsdale, NY 12529

    Mitchell St is one of the most picturesque roads in Hillsdale and this property has a beautiful gentleness to it. Comprising of three separate contiguous lots (35.2 acres, 43.1 acres and 48.8 acres per assessor); access comes in off the southern most lot (43.10) and meanders through the property by a pond site, open meadows, old fruit trees and views of the hills around. The middle lot takes you

    Jennifer Harvey Compass Greater NY LLC

    0 Mitchell St Unit 20251360, Hillsdale, NY 12529
  • /10

    $3,600,000

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

    90 W End Rd, Hillsdale, NY 12529

    For the first time on the market in 50 years, Underwood Farm, with its late 18th century cedar shake 3200 square foot salt box house, is 281 acres of primo hilltop exposure. Driving the property, the entire expanse is the high ground between West End Road and Rockledge Road with its equal parts woods, open meadows and fields with the rolling Taconics to the East. Below, the neighborhood is

    Parker Meyer Four Seasons Sotheby's Int.

    90 W End Rd, Hillsdale, NY 12529
  • /19

    $850,000

    • Land
    • 150 Acres
    • $5,667 per Acre

    0 Overlook Dr, Hillsdale, NY 12529

    Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

    MATTHEW CAREY Rouse + Co Real Estate

    0 Overlook Dr, Hillsdale, NY 12529
  • /37

    $695,000 New Construction

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

    30 Ridge Ln, Hillsdale, NY 12529

    Offering privacy, quality construction, and an ideal location. Set in the heart of the Roe-Jan region of the Hudson Valley and at the edge of the Berkshires, this home is tucked privately among mature trees on nearly eight acres while remaining close to the center of town. Recently constructed by one of the region's top builders, the residence was designed with both quality and longevity in mind.

    John Barbato Compass, Hillsdale

    30 Ridge Ln, Hillsdale, NY 12529
  • /72

    $775,000 Open Sun 11AM - 2PM

    • 7 Beds
    • 5 Baths
    • 4,608 Sq Ft

    9161 New York 22, Hillsdale, NY 12529

    A rare and versatile offering making its debut to the market for the very first time, this exceptional mixed-use property presents a unique opportunity to live, work, invest, and create. Set on just under two acres in a prime location, the property has long been owned and occupied by a respected local builder with thoughtful planning and flexibility throughout. Conveniently located just minutes

    Paige Backhaus William Raveis Real Estate

    9161 New York 22, Hillsdale, NY 12529
  • /16

    $689,000

    • 3 Beds
    • 2.5 Baths
    • 2,256 Sq Ft

    621 County Route 21, Hillsdale, NY 12529

    This updated contemporary home in Hillsdale offers a perfect blend of comfort and style on 10 private acres. The interior features a mix of hardwood, carpet, and nearly new vinyl flooring complemented by fresh paint and trim throughout. The kitchen comes fully equipped with a refrigerator, microwave, and stove. Enjoy a semi-finished basement. Key updates include new electric and plumbing, an

    Derek Greene The Greene Realty Group

    621 County Route 21, Hillsdale, NY 12529
  • /23

    $495,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,375 Sq Ft

    217 Anthony St, Hillsdale, NY 12529

    A newly built home ideally located on the edge of the charming hamlet of Hillsdale, NY, this home offers the convenience of true walkability--just steps to everyday essentials including the local hardware store, grocery market, wine shop, post office, town hall, coffee shops, restaurants, and boutique shops. With 3-bedrooms and 2-bathrooms, the home spans approximately 1,350 square feet of modern

    John Barbato Compass, Hillsdale

    217 Anthony St, Hillsdale, NY 12529
  • /25

    $770,000 New Construction

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

    801 Rodman Rd, Hillsdale, NY 12529

    New listing in Hillsdale, set high on a quiet dirt road where privacy, peace, and panoramic views define your backdrop. Why wait a year and a half for a new house to be built? This brand-new construction is being sold as it stands today, as a blank unfinished canvas ready for you to make it your own. The structure is in place with a brand-new drilled well, septic system, and 200-amp electrical

    Michael Castellano Gilcrest Properties

    801 Rodman 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
  • /34

    $719,000

    • 4 Beds
    • 3 Baths
    • 1,475 Sq Ft

    81 Black Grocery Rd, Hillsdale, NY 12529

    On a quiet country road, sit's the prettiest sunshine yellow house you've ever seen.Welcome to a property where outdoor splendor and indoor comfort merge seamlessly, where everything has been taken care of, and all you need to do is arrive and exhale. Rolling hills and open farmland stretch out before you, and they're all yours to enjoy.Inside, the dining room flows into an open kitchen

    Shaina Marron Houlihan Lawrence Inc.

    81 Black Grocery Rd, Hillsdale, NY 12529
  • /11

    $319,000

    • 2 Beds
    • 1 Bath
    • 728 Sq Ft

    15 Melvin Rd, Craryville, NY 12521

    Move right into this 1960 Copake Lake cottage with deeded lake rights! On a quiet road just a five minute walk to the lake is your quaint oasis lovingly restored in 2023. Upgrades include a new open concept kitchen, living and dining area. Bathroom completely remodeled with walk-in shower. Upgraded mechanicals include furnace, oil tank, hot water heater, well pump and plumbing. The backyard

    John Peterson THE TRUSS GROUP LLC

    15 Melvin Rd, Craryville, NY 12521
  • /27

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 2,093 Sq Ft

    149 Julianna Dr, Copake, NY 12516

    This approximately 2,100-square-foot ranch is sited on ~10 acres within The Birches HOA. The home offers three bedrooms and two-and-a-half bathrooms, an eat-in kitchen, and a dining room that opens to the living room. Both a wood-burning fireplace and a wood stove provide warmth and character. The land is a standout feature, with established fruit-bearing trees and a fenced vegetable garden. An

    Lindsay Lebrecht Copake Lake Realty Corp.

    149 Julianna Dr, Copake, NY 12516
  • /21

    $1,650,000

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

    75 Upper Hollow Rd, Hillsdale, NY 12529

    A rare 193-acre estate in Austerlitz/Hillsdale, very close to the Berkshire border. The charming 3-bed cottage overlooks a pristine pond with a bordering creek. The wooded land has clearly marked and maintained hiking trails. Recently renovated, the cottage features an updated bathroom and an expanded living room, blending modern comfort with rustic charm. Geothermal heating and air conditioning

    Janet Kain The Kinderhook Group, Inc.

    75 Upper Hollow Rd, Hillsdale, NY 12529
  • /13

    $1,080,000

    • Land
    • 72 Acres
    • $15,000 per Acre

    0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529

    Picturesque farmland located close to the Village of Hillsdale, only 1.8 to Catamount Ski Area, and 9.5 miles to Great Barrington. Extensive road frontage, totaling 3979 feet on Yonderview Road and Route 23. Barn complex. This parcel is zoned RU in the Town of Hillsdale. Property currently enjoys an agricultural exemption. Survey available. Inspect Now!

    Robert D Ferris R. Ferris Real Estate, LLC

    0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529
  • /69

    $2,995,000

    • 4 Beds
    • 3 Baths
    • 3,641 Sq Ft

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

    Welcome to Wolverton Creative Compound, a 119-acre estate in Claverack, NY, offering total privacy, wide southern light, integrated live-work studios, and a large swimmable pond with pebble beach. The 1830s farmhouse features four bedrooms, two baths, original moldings and Dutch doors, a whole-house water filter, and a bright layout for indoor-outdoor living. A fully insulated studio barn is

    Anthony D'Argenzio Houlihan Lawrence

    88 Mac Brown Rd, Claverack-Red Mills, NY 12513
  • /45

    $3,395,000 New Construction

    • 4 Beds
    • 4 Baths
    • 3,855 Sq Ft

    110 Mansfield Rd, Hillsdale, NY 12529

    Welcome to a newly built modern farmhouse set on 11.7 private acres in the heart of magical Hillsdale. Arriving via a sweeping driveway, rolling, manicured lawns unfold into cultivated fields. Designed for indoor-outdoor living, this 4-bedroom, 4-bath home features a dramatic great room with floor-to-ceiling glass for uninterrupted, far-reaching views.The residence offers a rare blend of

    Peter Yates Four Seasons Sotheby's Int.

    110 Mansfield Rd, Hillsdale, NY 12529
  • /19

    $325,000

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    81 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! Property

    Margaret Bower Avenia Columbia County RE Specialist

    81 SW Colony Rd, Hillsdale, NY 12529

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