Dana Robyn Chubb
Licensed Real Estate Salesperson, PSA
PSA, REALTOR®
Delhi, NY
Office: (607) 746-7400 (518) 522-6779
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144 Underhill Road, Hillsdale, NY 12529

New - 11 Hours Ago

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Property Description

This architect-owned and thoughtfully renovated 1880s Hudson Valley farmhouse in the hamlet of Hillsdale effortlessly brings together historic character and contemporary design. Original details and a striking modern addition create a home that feels timeless, warm, and modern. Distinctive, beautifully maintained, and move-in ready, this home is perfect for weekend getaways or year-round living offering privacy, and convenience--set in one of the regions most sought-after landscapes.Enter the dramatic addition with its 12-foot ceilings and abundant natural light -- built to expand the living and dining spaces which flow into the beautifully designed kitchen. Thoughtful details and an intuitive layout make the heart of the home equally inviting for both quiet mornings and effortless entertaining.Approximately 1,800 square feet, the three-bedroom, two-bath home is layered with original character, including hand-hewn beams and hardwood floors. A wood-burning stove adds warmth and atmosphere on winter evenings, while two well-appointed bathrooms feature custom details and generous storage. The home sits on 1.3 acres.The convenient mudroom off the kitchen hallway, complete with washer and dryer, provides a practical transition from country life to indoors. Throughout, ample storage and carefully considered spaces make the home remarkably functional without compromising its relaxed, welcoming feel.Outside, the gardens are as appealing as the house itself. Stone walls, mature plantings, generous flower beds, and a spacious wood deck create a series of inviting outdoor spaces for summer barbecues, long afternoons, and enjoying the changing seasons. An upstate barn, ready for its next chapter, adds another layer of character and possibility.The location offers an exceptional balance of privacy and access. Catamount Ski Resort and the Harlem Valley Rail Trail are just minutes away, while Great Barrington is less than 20 minutes by car and Hudson and the Amtrak station are approximately 30 minutes away. Manhattan is a little over two hours by car, or accessible by train to Grand Central, making this an ideal year-round home and an effortless weekend escape.

144 Underhill Road | MLS# 20265936

This single family home located at 144 Underhill Road, Hillsdale, NY 12529 is currently listed for sale with an asking price of $725,000. This property was built in 1880 and has 3 bedrooms and 2 full baths with 1800 sq. ft. Underhill Road is located within the Taconic Hills Central Schools school district. Search Hillsdale real estate on dana-chubb.timberlandproperties.com today.

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Property Features

Property Type: Residential - Single Family
Basement: Yes
Cooling: Central Air, See Remarks
Fuel Type: Oil
Heating: Oil, Wood Stove
Home Style: Farmhouse
Lot Size: 1.30 Acres
Taxes: $1
Year Built: 1880

Feature Descriptions

Flooring: Hardwood
Parcel #: 156.-2-6
SQFT Total: 1800

Local Schools

School District: Taconic Hills Central Schools

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Estimated Payment

$ 1,825.08 per month $1,613.54 Principal & Interest $0.08 Property Tax $211.46 Homeowner's Insurance

Change Payment Information

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yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Houlihan Lawrence Inc.

Shown By

Agent Name: Dana Robyn Chubb
Agent Phone: (518) 522-6779
Agency Title: Timberland Properties

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All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 10/07/2026. The listing information on this page last changed on 10/07/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 10/07/2026 12:00:47 AM EST) or Global MLS (last updated Tue 10/06/2026 8:13:18 AM EST) or New York State Alliance MLS (last updated Tue 10/06/2026 11:58:57 PM EST) or Hudson Valley Catskill Region MLS (last updated Tue 10/06/2026 11:51:15 PM EST) or OneKey MLS (last updated Tue 10/06/2026 11:53:19 PM EST). Real estate listings held by brokerage firms other than Timberland Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless.

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