Homes for Sale in 12529

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  /54

  $1,100,000

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

  2666 New York 23, Hillsdale, NY 12529

  Unique investment opportunity in the hamlet of Hillsdale. This new-to-the-market commercial/residential property has been meticulously renovated by the current owner, a commercial builder, who over-engineered the project with high-end features throughout.The property consists of four distinct rental units:2666 Route 23, Main (Blue) Building- First-Floor Commercial Unit Right Side:

  Margaret Bower Avenia Columbia County RE Specialist

  2666 New York 23, Hillsdale, NY 12529
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  /42

  $900,000

  $200K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,495 Sq Ft

  309 Pine Ridge Ln, Hillsdale, NY 12529

  Nestled on a wooded hillside on one of Hillsdale's prettiest country roads is where you will discover this exceptional 2,500 sq.ft. custom-built home. The 5.5-acre parcel sits above Pine Ridge Lane; a lightly travelled country road located just off Mitchell Street in the heart of Hillsdale. Surrounded by nature in every direction, the peaceful, park-like setting is unique and as beautiful as any

  Margaret Bower Avenia Columbia County RE Specialist

  309 Pine Ridge Ln, Hillsdale, NY 12529
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  /31

  $725,000

  • 4 Beds
  • 2.5 Baths
  • 2,225 Sq Ft

  2999 New York 23, Hillsdale, NY 12529

  2999 Route 23, Hillsdale, New York - Historic Country Estate on 12.5 AcresStep into a piece of living history with this beautifully preserved 1915 home, perfectly situated on a private 12.5-acre parcel in the heart of the Berkshires. Offering four generous bedrooms and three baths (2 full, 1 Half), this classic residence blends timeless charm with everyday comfort, creating an ideal

  Tyler Bervy Stone House Properties, LLC

  2999 New York 23, Hillsdale, NY 12529
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  /25

  $575,000

  $74K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft

  416 Whippoorwill Rd, Hillsdale, NY 12529

  416 Whippoorwill Rd, Hillsdale, NY ~ PRIVATE SETTING!! Cape Cod style home, built in 2000, meticulously maintained and is in excellent condition inside and out. The main level features a functional kitchen, dining area, bathroom, and living room centered around a propane fireplace; all with hardwood floors. A 12x12 great room with hardwood floors was added to provide additional living space.

  Margaret Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

  416 Whippoorwill Rd, Hillsdale, NY 12529
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  /35

  $624,000

  $95K PRICE DROP

  • 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
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  /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
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  /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
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  /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
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  /7

  $255,000

  $4K PRICE DROP

  • 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
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  /4

  $195,000

  • Land
  • 2.54 Acres
  • $76,772 per Acre

  10 -Stonegate Off Birch Hill Rd, Copake, NY 12521

  Build your dream home at Stonegate, an exclusive, tranquil subdivision with 425 acre Copake Lake access, an HOA private community dock and available boat slip. Lot 10 is BOHA approved and offers serene natural surroundings with utilities available. Perfect for nature enthusiasts seeking a peaceful retreat. Enjoy convenient access to amenities and nearby attractions. The Berkshires offer endless

  Maria DiSalvo Coldwell Banker Prime

  10 -Stonegate Off Birch Hill Rd, Copake, NY 12521
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  /4

  $225,000

  • Land
  • 2.16 Acres
  • $104,167 per Acre

  9 Stonegate Off Birch Hill Rd, Copake, NY 12521

  Build your dream home at Stonegate, an exclusive, tranquil subdivision with 425 acre Copake Lake access, an HOA private community dock and available boat slip. This 2+ acre prime vacant lot (Lot 9 ) is BOHA approved and offers serene natural surroundings with utilities available. Perfect for nature enthusiasts seeking a peaceful retreat. Enjoy convenient access to amenities and nearby

  Maria DiSalvo Coldwell Banker Prime

  9 Stonegate Off Birch Hill Rd, Copake, NY 12521
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  /5

  $225,000

  • Land
  • 2.39 Acres
  • $94,142 per Acre

  8 Stonegate Off Birch Hill Rd, Copake, NY 12521

  Prime vacant land at Stonegate, a tranquil exclusive subdivision at Copake lake to build your dream home. Lot 8 is BOHA approved and offers serene natural surroundings with utilities available.Perfect for Lake enthusiasts and all that nature has to offer.Enjoy convenient access to amenities and nearby attractions. Plus, Copake Lake access with an HOA private community dock and available boat

  Maria DiSalvo Coldwell Banker Prime

  8 Stonegate Off Birch Hill Rd, Copake, NY 12521
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  /4

  $295,000

  • Land
  • 6.8 Acres
  • $43,382 per Acre

  5 Stonegate Off Birch Hill Rd, Copake, NY 12521

  Build your dream home at Stonegate, an exclusive, tranquil subdivision with 425 acre Copake Lake access, an HOA private community dock and available boat slip.This 6+ acre prime vacant lot (Lot 5) is BOHA approved and offers serene natural surroundings with utilities available. Lot 5 is at the end of a cul-de-sac. The mature four-trunk white oak, as you drive into the lot, estimated to be

  Maria DiSalvo Coldwell Banker Prime

  5 Stonegate Off Birch Hill Rd, Copake, NY 12521
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  /6

  $350,000

  • Land
  • 5.02 Acres
  • $69,721 per Acre

  6 Stonegate Off Birch Hill Rd, Copake, NY 12521

  Discover your dream home at Stonegate, an exclusive, tranquil subdivision with 425 acre Copake Lake access, an HOA private community dock and available boat slip.This 5+ acre prime vacant lot (Lot 6) is BOHA approved and offers serene natural surroundings with utilities available. An owners favorite, Lot #6 is a wooded, with a pond view and plenty of hardwoods, trails, seasonal stream and

  Maria DiSalvo Coldwell Banker Prime

  6 Stonegate Off Birch Hill Rd, Copake, NY 12521
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  /40

  $1,250,000

  New Construction Open Sun 12:30PM - 1:30PM $225K PRICE DROP

  • 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
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  /11

  $285,000

  $34K PRICE DROP

  • 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
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  /40

  $799,000

  $180K PRICE DROP

  • 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
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  /24

  $575,000

  $40K PRICE DROP

  • 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
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  /21

  $339,900

  $60K PRICE DROP

  • 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
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  /16

  $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
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  /44

  $1,250,000

  $45K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,395 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
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  /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
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  /6

  $175,000

  $120K PRICE DROP

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

  50 Dugway Rd, Hillsdale, NY 12529

  Escape to 33.31 acres of untouched beauty in Columbia County, NY. 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. This parcel features a dynamic topography of hills that reach an elevation of over 1,000 feet. With this parcel,

  Jeffrey McKinney Beach & Bartolo Realtors

  50 Dugway Rd, Hillsdale, NY 12529
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  /17

  $999,000

  $271K PRICE DROP

  • 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
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  /13

  $1,080,000

  $5K PRICE INCREASE

  • 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

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