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251 Overlook Drive, Hillsdale, NY - Historic Mountain Cabin Retreat with Stream & Scenic Views Discover the magic of Hillsdale, NY, in this idyllic 1900 cabin sanctuary, perched atop a private mountaintop with breathtaking views of the foothills of the Berkshires. Set on 4.5 acres with wide frontage and a gently flowing active stream, this rare property blends rustic charm with modern comfort, offering a true four-season escape in the heart of Columbia County. As you turn onto Overlook Drive, a long, gently winding road leads you to this mountaintop retreat, building a sense of anticipation and timeless charm with every turn. Step inside to experience the warmth of an enormous original stone fireplace, soaring cathedral ceilings, and a brand-new enamel stove with thermal glass doors and fully lined chimney"”perfect for cozy evenings after skiing or exploring. A whimsical children's loft with a spy hole greets you above the entry, adding character and charm that make this mountain getaway feel like home. Enjoy the serenity of rural mountaintop living without sacrificing connectivity, thanks to available high-speed internet (Spectrum 1Gbps). Wake to the sight of a mist-covered field at sunrise, or savor the serenity of fresh snowfall blanketing your land in absolute quiet. In summer, enjoy the expansive lawn"”ideal for a pool or tennis court"”or explore your own woodland stream. Just minutes from Catamount Ski Area and its exhilarating Aerial Adventure Park, this home is both a winter ski chalet and a summer adventure hub. Nestled between the charming, historic town of Hudson, NY, and the picturesque, culturally rich village of Great Barrington, MA, Hillsdale offers farm-to-table dining, vibrant cultural attractions, and easy access to both the Hudson Valley and the Berkshires"”making it an ideal weekend escape or year-round retreat. With seasonal mountain views, wide-open acreage, and unmatched character, 251 Overlook Drive is a rare opportunity to own a piece of Columbia County's history while embracing the lifestyle of the Hudson Valley. Only about 2 hours by car or Amtrak from Midtown Manhattan! Don't miss the chance to make this mountain cabin retreat your own. Though believed accurate, all information"”including taxes and schools"”must be independently verified. Information has been provided by the Seller and has not been verified by the Broker. Taxes are stated for 2024-2025. Schools are reported by Niche. Information is deemed reliable but not guaranteed. Owner, Listing Agent & Broker are not responsible for inaccuracies; prospective buyers and their agents must confirm all facts.
| DAYS ON MARKET | 3 | LAST UPDATED | 10/2/2025 |
|---|---|---|---|
| YEAR BUILT | 1900 | COUNTY | Columbia |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| Elementary School | Taconic Hills Elementary School |
|---|---|
| Jr. High School | Taconic Hills Junior/Senior High |
| High School | Taconic Hills Junior/Senior High |
| ADDITIONAL DETAILS | |
| AIR | None |
|---|---|
| APPLIANCES | Electric Cooktop, Electric Oven, Microwave, Refrigerator |
| CONSTRUCTION | Frame |
| FIREPLACE | Yes |
| HEAT | Baseboard, Electric |
| INTERIOR | Beamed Ceilings, Cathedral Ceiling(s), Open Floorplan |
| LOT | 4.5 acre(s) |
| PARKING | Driveway |
| SEWER | Septic Tank |
| STYLE | Cabin |
| TAXES | 2704 |
| UTILITIES | Electricity Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Mountain(s), Panoramic, Trees/Woods |
| WATER | Private, Well |
| WATERFRONT DESCRIPTION | Waterfront Access |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listed with DynamicEdge Realty LLC
Copyright 2025 Hudson Gateway Multiple Listing Service, Inc. All rights reserved.
The data relating to real estate for sale or lease on this web site comes in part from HGMLS. Real estate listings held by brokerage firms other than Verdeschi & Walsh Realty are marked with the HGMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. Information deemed reliable but not guaranteed.
Date Last Updated: 10/3/25 4:27 PM PDT
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