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Homes for Sale in 12529

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  • /40

    $1,295,000

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    4 Bobolink Rd, Craryville, NY 12521

    Beautifully renovated circa-1900 lakefront cottage on Copake Lake, just over two hours from New York City and minutes from golf, dining, and year-round Hudson Valley and Berkshire attractions. Blending timeless charm with modern comforts, this four-bedroom, two-bath home offers the perfect waterfront retreat. Inside, exposed beams, hardwood floors, and an electric fireplace create a warm and

    Heather Cohen Compass, Hillsdale

    4 Bobolink Rd, Craryville, NY 12521
  • /7

    $39,900

    • Land
    • 26,571 Sq Ft
    • $65,410 per Acre

    0 Prach Road Extension Unit 20263433, Claverack, NY 12513

    Take advantage of this opportunity to build your dream home on this cleared, flat, .61 acre parcel (with well on property). Conveniently located just minutes to Hudson's restaurants, shops, and Amtrak station, or if you prefer outdoor activities e.g. hiking, kayaking, skiing, and ariel adventure, it's all within a short drive to Bash Bish Falls State Park, Copake Lake, and Catamount Mountain

    Wendy Kenney Davala Real Estate, LLC

    0 Prach Road Extension Unit 20263433, Claverack, NY 12513
  • /20

    $1,695,000

    • Land
    • 127 Acres
    • $13,346 per Acre

    0 Mitchell St Unit 249980, 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

    Tom Lynch COMPASS MASSACHUSETTS , LLC GB

    0 Mitchell St Unit 249980, Hillsdale, NY 12529
  • /33

    $389,000

    Open Sun 12PM - 2PM
    • 4 Beds
    • 1 Bath
    • 2,229 Sq Ft

    1953 County Road 11, Claverack, NY 12513

    Step into a home that feels like it has been quietly telling its story since the 1800's, where every beam and board carries the charm of a bygone era. This classic colonial residence preserves its original character with exposed beams stretching across the main floor and a layout that balances simplicity with purpose. The kitchen is modest yet functional, anchored by a traditional wood store that

    Karen Davala Davala Real Estate, LLC

    1953 County Road 11, Claverack, NY 12513
  • /7

    $95,000

    • Land
    • 12.95 Acres
    • $7,336 per Acre

    00 Stone Ledge Rd, Hillsdale, NY 12529

    Quiet location next to the Berkshires. Dead end road with a 12 acre parcel. Hiking trails throughout. Glorious views off the top. Great value. More land available.

    Tracy Tassinari Gabel Real Estate

    00 Stone Ledge Rd, Hillsdale, NY 12529
  • /31

    $995,000

    • 2 Beds
    • 2 Baths
    • 2,060 Sq Ft

    17 Memory Ln, Hillsdale, NY 12529

    Lakefront living in one of the most peaceful and serene locations on Copake Lake. An expansive 75 feet of private waterfront with an existing dock, this charming home offers beautiful eastern views across the lake, where sunrises and tranquil water vistas become part of everyday life.The home's inviting open-concept layout has a spacious kitchen, dining, and living area. A first-floor primary

    John Barbato Compass, Hillsdale

    17 Memory Ln, Hillsdale, NY 12529
  • /12

    $95,000

    • Land
    • 6.25 Acres
    • $15,200 per Acre

    0 Stone Ledge Rd, Hillsdale, NY 12529

    Quiet parcel with a small cabin and a shed. Shed with loft area and porch. Nestled on a dead end road in Hillsdale. Cleared paths with trails. Quiet location close to MA. Great value.

    Tracy Tassinari Gabel Real Estate

    0 Stone Ledge Rd, Hillsdale, NY 12529
  • /50

    $999,900

    Open Sat 11AM - 1PM
    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    2955 State Route 23, Hillsdale, NY 12529

    Steeped in Hillsdale’s rich history, this extraordinary property began its life as one of the area’s original grist mills, situated in the area of Hillsdale once known as Murray’s Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

    Jason Walch Coldwell Banker Advisor Realty

    2955 State Route 23, Hillsdale, NY 12529
  • /58

    $999,900

    Open Sat 11AM - 1PM
    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    2955 New York 23, Hillsdale, NY 12529

    Steeped in Hillsdale's rich history, this extraordinary property began its life as one of the area's original grist mills, situated in the area of Hillsdale once known as Murray's Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

    Jason Walch Coldwell Banker Advisor Realty

    2955 New York 23, Hillsdale, NY 12529
  • /5

    $225,000

    • Land
    • 6 Acres
    • $37,500 per Acre

    L135.2 Rockledge Rd, Hillsdale, NY 12529

    Escape to your own private sanctuary in the heart of Columbia County's coveted Hudson Valley. This 6 acre wooded parcel on scenic Rockledge Road offers the perfect canvas for your dream retreat, with mature trees providing natural privacy and a peaceful, secluded setting that feels worlds away from the everyday. Ideally situated in the Town of Hillsdale -- one of the region's most sought-after

    Agent Photo

    Jamie Mazuryk

    Venture Fox Realty Group LLC

    (518) 719-4612

    L135.2 Rockledge Rd, Hillsdale, NY 12529
  • /31

    $349,900

    • 4 Beds
    • 2 Baths
    • 2,080 Sq Ft

    9161 Ny-22, Copake, NY 12516

    Just minutes from the center of Hillsdale, Roe Jan Park, and the Harlem Valley Rail Trail, this split-level ranch offers a convenient location with easy access to some of the area's most popular outdoor and community amenities. The 2,080-square-foot home features four bedrooms and two bathrooms, providing a practical layout with space for everyday living. A bright sunroom serves as a natural

    Paige Backhaus William Raveis Real Estate

    9161 Ny-22, Copake, NY 12516
  • /5

    $399,000

    • Land
    • 12.18 Acres
    • $32,759 per Acre

    3551 County Rd 7, Copake, NY 12516

    A true beauty! Discover the perfect setting for your dream home on this stunning 12.18-acre parcel featuring mostly open, sprawling fields and breathtaking distant countryside views. With ample space for a private estate, hobby farm, gardens, or recreational enjoyment, this picturesque property offers the ideal blend of rural tranquility and convenient access to area amenities.Enjoy a prime

    Theresa Westlake Copake Lake Realty Corp.

    3551 County Rd 7, Copake, NY 12516
  • /48

    $3,850,000

    • 5 Beds
    • 5.5 Baths
    • 5,083 Sq Ft

    335 Dawson Rd, Hillsdale, NY 12529

    Presiding over 27 acres of rolling hills, meadows, and dramatic mountain views, Southview Farm is a fully reimagined country estate in the heart of Hillsdale farm country. Once part of a 300-acre dairy farm with a grand farmhouse on this site for over a century, the property has been expanded and rebuilt from the ground up to deliver modern luxury, efficiency, and comfort while honoring its

    Norah Burden Brown Harris Stevens HV LLC

    335 Dawson Rd, Hillsdale, NY 12529
  • /12

    $850,000

    • Land
    • 19.7 Acres
    • $43,147 per Acre

    2 Ridge Ln, Hillsdale, NY 12529

    Shangri - La Off of Overlook Drive, on Ridge Lane a harmonious, breathtakingly beautiful 19 acre property with outstanding views over rolling pastures, distant hills and the Catskill Mountains; privacy and peace pervade. A dirt drive gently curves around a lovely pond and through the woods landing in a high clearing and perfect building site. BOHA approved. For an interested buyer, a stunning

    Nicole Vidor Nicole Vidor Real Estate Inc.

    2 Ridge Ln, Hillsdale, NY 12529
  • /23

    $305,000

    $15K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 925 Sq Ft

    9377 New York 22, Hillsdale, NY 12529

    WELCOME HOME to this charming and stylishly updated retreat situated on a spacious, level lot in beautiful Hillsdale, NY! Offering a perfect blend of modern character and country appeal, this home is ideal for those looking for a peaceful getaway with fantastic outdoor space. As you arrive, the striking dark grey exterior, crisp white accents, and charming fenced-in front yard lead you to a

    Ronald Green KW Mid-Hudson

    9377 New York 22, Hillsdale, NY 12529
  • /57

    $795,000

    • 3 Beds
    • 2 Baths
    • 1,376 Sq Ft

    1 Breezy Hill Rd, Copake Falls, NY 12517

    This 1887 farmhouse sits on a quiet country road in Copake Falls and is one of the last remaining original farmhouses in this corner of Columbia County. Set on 1.3 grandfathered acres bordered by conserved land and larger neighboring parcels, it lives far bigger than its acreage suggests. Comprehensively renovated with an authentic farmhouse sensibility, the home features a chef's kitchen, a

    Anthony D'Argenzio Houlihan Lawrence

    1 Breezy Hill Rd, Copake Falls, NY 12517
  • /5

    $259,000

    • Land
    • 15.47 Acres
    • $16,742 per Acre

    191 Berkshire Rd, Hillsdale, NY 12529

    Discover the perfect opportunity to build your dream home on this expansive 15.47-acre parcel at 191 Berkshire Road, bordering Copake Country Club and just minutes from Copake Lake. This fully undeveloped property is part of the desirable Sam Hill Road community, offering shared waterfront access through the HOA. Ideally located just 25 minutes from Hudson and Great Barrington, MA, you'll enjoy

    Austin Urban Venture Fox Realty Group

    191 Berkshire Rd, Hillsdale, NY 12529
  • /55

    $1,525,000

    • 4 Beds
    • 4.5 Baths
    • 3,666 Sq Ft

    83 Schmeichel Rd, Hillsdale, NY 12529

    Custom contemporary home built in 1996 with thoughtful gathering spaces. Main floor has a vaulted ceiling living room with fireplace, open to dining and the eat-in-kitchen. Down a hall to the south end there is the primary suite, a powder room, laundry, the den with a vaulted ceiling and a woodstove and access to the garage. On the north side of the main living room is a large entry foyer, a

    Jennifer Harvey Compass Greater NY LLC

    83 Schmeichel Rd, Hillsdale, NY 12529
  • /39

    $649,000

    • 3 Beds
    • 2 Baths
    • 1,753 Sq Ft

    51 Sabeff Rd, Hillsdale, NY 12529

    51 Sabeff Road is new to the market for the first time since the original owner, Sabcho Sabeff, sold it in 1981. It has been enjoyed as a family compound by the current owners since that time. Entering the property from Sabeff Road, a town maintained dead end road in the heart of Hillsdale, is like taking a step back in time. This spectacular parcel is a nice mix of flat lawn and slightly sloping

    John Avenia Columbia County RE Specialist

    51 Sabeff Rd, Hillsdale, NY 12529
  • /45

    $1,150,000

    • 5 Beds
    • 3 Baths
    • 1,708 Sq Ft

    1 van Bueran Dr, Hillsdale, NY 12529

    Set just off the banks of Copake Lake and privately positioned on five wooded acres, The Van Bueran House offers a rare blend of modern design, an inground pool, and deeded lake rights to one of Columbia County's most sought-after motorboat lakes. Recently renovated with forever in mind, the home pairs thoughtful design with meaningful infrastructure: white oak and radiant heated floors

    Jessica Scott Compass Greater NY, LLC

    1 van Bueran Dr, Hillsdale, NY 12529
  • /41

    $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

    Tom Lynch COMPASS MASSACHUSETTS , LLC GB

    292 White Hill Rd, Hillsdale, NY 12529
  • /26

    $1,195,000

    Open Sat 11AM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 1,931 Sq Ft

    523 Breezy Hill Rd, Hillsdale, NY 12529

    Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The

    Mimi Harson William Pitt Sotheby's

    523 Breezy Hill Rd, Hillsdale, NY 12529
  • /20

    $325,000

    • Land
    • 22.84 Acres
    • $14,229 per Acre

    0 County Route 21, Hillsdale, NY 12529

    Welcome to DREAMLAND.Set along a quiet country road, this exceptional 22 acre parcel offers the rare combination of privacy, curated natural beauty, and effortless access from New York City. Just minutes from the Taconic State Parkway, the property is ideally positioned for seamless weekend escapes or full-time living. A sun-drenched open meadow--perfectly oriented for southern

    Pamela King-Belfor Four Seasons Sotheby's Int.

    0 County Route 21, Hillsdale, NY 12529
  • /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: 360

    Margaret Bower Avenia Columbia County RE Specialist

    2666 New York 23, Hillsdale, NY 12529
  • /42

    $1,100,000

    • 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
  • /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 Acres Step 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 setting for

    Tyler Bervy Stone House Properties, LLC

    2999 New York 23, Hillsdale, NY 12529
  • /31

    $890,000

    • 4 Beds
    • 3 Baths
    • 2,040 Sq Ft

    49 Knapp Hollow Ln, Hillsdale, NY 12529

    Sited on 5 beautifully landscaped acres on a very quiet, park-like setting off a private road, this well maintained and thoughtfully designed home overlooks a tranquil pond and offers the perfect country escape. Designed by architect Dennis Wedlick, to maximize space and ease of living, the home features 3-4 bedrooms, and 3 baths, of which one is a primary ensuite and another a separate guest

    marylou Kersten Copake Lake Realty Corp.

    49 Knapp Hollow Ln, Hillsdale, NY 12529
  • /25

    $649,000

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

    416 Whippoorwill Rd, Hillsdale, NY 12529

    416 Whippoorwill Rd, Hillsdale, one of the prettiest country roads Columbia County has to offer!! This one checks all of the boxes. Our newly listed two bedroom, two bath Cape Cod style home in Hillsdale has been 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

    Margaret Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

    416 Whippoorwill Rd, Hillsdale, NY 12529
  • /23

    $370,000

    Open Sat 10:30AM - 1PM $49K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,303 Sq Ft

    16 Robin Rd, Craryville, NY 12521

    PRICE IMPROVEMENT! WOWZA!!! THIS IS AN AMAZING NEW PRICE AND 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,

    Blanche Mackey Copake Lake Realty Corp.

    16 Robin Rd, Craryville, NY 12521
  • /25

    $310,000

    $15K PRICE DROP
    • 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
  • /34

    $695,000

    $24K 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
  • /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
  • /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
  • /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

    $257,000

    $2K 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
  • /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
  • /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
  • /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
  • /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
  • /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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