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108 NY-344, Copake
$495,000
6 Baths ⋅ 202628204 MLS
Welcome to the Taconic Wayside Inn, a roadside tavern and boarding house dating to 1856, set on 1.2 acres in Copake Falls at the edge of Taconic State Park. The 5,512-square-foot main building holds a commercial kitchen, a tavern with a wraparound bar, 3 dining rooms, 5 guest rooms, and 3 apartments, with a large pole barn and additional outbuildings. Babe Ruth was a regular here, and for more than fifty years, under one family's care, the inn played host to weddings, reunions, and local bands. Commercial, agricultural, and residential zoning supports a restaurant, boutique inn, mixed-use investment, or private residence. The Taconic Wayside Inn stands ready to become the gathering place of Copake Falls once again, and a destination for the whole region.

108 NY-344, Copake
3493 County Road 7, Hillsdale
$650,000
3 Beds ⋅ 3 Baths ⋅ 202621523 MLS
Escape to your own private retreat where lake living, outdoor adventure, and timeless country charm come together! Just steps from scenic Copake Lake, this property offers access to one of Columbia County's premier recreational destinations. Copake Country Club features an 18-hole championship golf course and year-round dining. Conveniently located between Hudson and Great Barrington, and just a short drive to Catamount Mountain Resort, the area offers four-season recreation, with the tranquility of your own beautifully landscaped 4.66 acre setting. Inside, this home is rich with warmth and timeless character. The inviting eat-in kitchen features a breakfast bar, abundant cabinetry, and a pantry, creating a functional space that will delight any home chef. Just beyond, the dining area flows seamlessly into the spacious living room where a cozy wood-burning stove, custom built-in bookcases, and decorative wood trim create a welcoming atmosphere for everyday living and entertaining. The bright, glass enclosed sunroom provides the perfect spot for morning coffee, reading, or simply relaxing, while a handily located half bath completes the main level. Upstairs, you'll find three comfortable bedrooms and two full bathrooms. Gleaming hardwood floors span throughout both levels, and an abundance of natural light fills the home, enhancing the attractive appeal. Outside, the detached two-car garage includes ample room for a workshop, lawn equipment and recreational storage. The second floor of the garage offers endless possibilities as an artist's studio, home office, fitness room, or hobby space. . Unwind beneath the covered patio and enjoy the serenity of your surroundings. Whether you're searching for a full-time residence or the perfect weekend getaway, this exceptional property offers the ideal balance of privacy, recreation, and convenience--just minutes from the Taconic State Parkway and only 2.5 hours from New York City.

3493 County Road 7, Hillsdale
152 Main Street, Philmont
$295,000
3 Beds ⋅ 2 Baths ⋅ 202616964 MLS
Welcome to Hawthorne Cottage, a circa 1900 updated residence on Main Street in the heart of Philmont's historic district, set on a sloping lot with a stone wall and partial woodland in one of Columbia County's most authentic small villages. The home has been fully renovated. Open shelving and curated details create inviting living spaces full of warmth and character. The kitchen includes butcher block counters, a herringbone tile backsplash, stainless steel appliances, and striking navy cabinetry accented by brushed brass hardware. New laminate floors run through every room and bathrooms have been updated. The cozy layout spans 1,392 square feet, with a half bath on the first floor and three bedrooms and a full bath above. The unfinished walk-out basement adds approximately 360 square feet of flexible additional space, and is ready to be finished to your own specifications. Ideal as a home office, guest quarters, home gym, or creative studio. A brand new heating system completes a renovation that leaves little to do but move in. Philmont is a small Columbia County village with a growing creative community and a genuine historic fabric. Hawthorne Valley School and its beloved farm store are nearby, as is the High Falls Conservation Area, where trails wind through hemlock ravines to Columbia County's highest waterfall. Local 111 and other village favorites are close at hand for dining. Hudson's Warren Street galleries, restaurants, and Amtrak station are eighteen minutes away, Chatham is fifteen minutes, and New York City is two and a half hours by car. The farm stands, hiking trails, and country roads that define life in this part of the valley are all within easy reach.

152 Main Street, Philmont
1820 Co Rte 7, Ancram
$1,995,000
4 Beds ⋅ 3 Baths ⋅ 202523369 MLS
Ancram 194 acre abandoned farm with great potential for agriculture or development. Many buildings in various stages of repair: Main House 75x50 on 2 levels; Steel Barns:50x150; 60x100, 75x40; barn complex: 35x55+35x15, 5x10, 35x60, 25x60; 2nd barns complex: 30x100 + 2 silos. Long road frontage and level productive land

1820 Co Rte 7, Ancram

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