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256 Hammond Hill Road

Dover Plains, NY 12522
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Bed 3

Bed

Bath 2

Bath

SqFt1,900

Sqft

Acres3

Acres(Lot)

Privately nestled on 3 serene acres in the rolling hills of Dover Plains, this beautifully reimagined country retreat offers an exceptional blend of privacy, refined modern updates, and effortless indoor-outdoor living. Set far back from the road and surrounded by mature trees and picturesque natural scenery, 256 Hammond Hill Road delivers a peaceful lifestyle with extraordinary entertaining space both inside and out. Accessed via a deeded right-of-way, the property offers a uniquely private setting while maintaining convenient accessibility. This inviting 3-bedroom, 2-bath residence spans approximately 1,788 square feet and features a bright, open-concept layout filled with natural light and thoughtfully curated finishes throughout. Completely renovated kitchen and bathrooms elevate the h ome with a sophisticated, modern aesthetic while preserving its warmth and timeless character. The stunning kitchen flows seamlessly into the dining and living areas, creating an airy atmosphere ideal for both everyday living and entertaining on any scale. Rich hardwood flooring, oversized windows, freshly painted interiors, and newly installed designer light fixtures throughout the kitchen, bathrooms, exterior, and hallways further enhance the home’s polished presentation. Major mechanical and functional improvements provide additional peace of mind, including newer appliances with most approximately two years old, a refrigerator replaced within the last year, and a recently updated well pump. The home also includes a newer pellet stove, approximately 3–4 years old, accompanied by both pellets and wood for the wood-burning stove, offering warmth and ambiance throughout the colder seasons. In addition to the primary living spaces, the home features an expansive bonus room offering remarkable versatility for a home office, guest accommodations, recreation space, fitness studio, or additional lounge area tailored to a variety of lifestyle needs. One of the property’s most captivating features is the oversized rear deck spanning the back of the home, creating a spectacular extension of the living space with multiple seating and dining areas overlooking tranquil wooded surroundings. Whether hosting summer gatherings, enjoying quiet mornings with coffee, or relaxing beneath the stars, the outdoor setting captures the essence of refined country living. Additional highlights include central air conditioning, included washer and dryer, a SimpliSafe security system that may be expanded by future owners, and an oversized garage with an additional oil tank for supplemental heat. Town of Washington documentation reflects updated approvals and retroactive Certificates of Occupancy for prior improvements, with no known violations currently on file. Conveniently located in the heart of Dutchess County, just moments from local shops, restaurants, hiking trails, Metro-North, and the charming nearby towns of Pawling, Millbrook, and Amenia, this exceptional offering combines modern enhancements, flexible living space, expansive outdoor entertaining, and timeless country elegance less than two hours from Manhattan.

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Detail Ic Property Details

Property Type : Residential

Price : $499,000

AD Id : 78063646

MLS Id : 996553

Beds : 3

Lot Size : 3 Acres

Living Area Size : 1,900

Year Built : 1970

Garage : 2

County : Dutchess

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Map

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Feature Features

  • Bedroom Information

    Total beds: 3

    Bathroom Information

    Total Baths: 2 Full Baths: 2

    Room Information

    Rooms Total: 10 Basement: Crawl Space
  • Flooring Information

    Hardwood
  • Interior Features

    Built-in Features, Cathedral Ceiling(s), Eat-in Kitchen, Kitchen Island, Open Floorplan, Recessed Lighting Appliances: Dishwasher, Dryer, Oven, Refrigerator, Washer Laundry Features: Laundry Room
  • Heating & Cooling

    Has Heating: Yes Heating: Oil Has Cooling: Yes Cooling: Central Air

  • Building Information

    Year Built: 1970 Construction Materials: Block Private Pool: No

  • Lot Information

    Lot Size Acres: 3 Lot Size Square Feet: 130680

  • Listing Price Information

    Listing Price: $499000 Original Price: $529000

  • Tax Information

    Parcel Number: 135889-6963-00-573881-0000 Annual Tax: $6106

  • Parking Information

    Parking Total: 6 Detached, Driveway

    Garage Information

    Has Garage: Yes Garage Space: 2

  • School Information

    Elementary School: Dover Elementary School
    Junior High School: Dover Middle School
    Senior High School: Dover High School
  • Utility Information

    Cable Available, Cable Connected, Electricity Available, Electricity Connected, Phone Available, Water Available, Water Connected
  • Location Information

    WaterSource: Public, Private, Well
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
326 Old State Route 22, Dover Plains, NY, 12522 $479,000 3 2 1,540 1,540 SqFt
360 Old State Route 22, Dover Plains, NY, 12522 $815,000 4 4 2,234 2,234 SqFt
105 Sand Hill Road, Dover Plains, NY, 12522 $450,000 1 1 805 805 SqFt
105 Sand Hill Road, Dover Plains, NY, 12522 $450,000 1 1 805 805 SqFt
9 Evan Road, Dover Plains, NY, 12522 $429,000 3 3 2,004 2,004 SqFt
151 Benson Hill Road, Dover Plains, NY, 12522 $3,750,000 7 7 6,138 6,138 SqFt
30 Tally-ho Drive, Dover Plains, NY, 12522 $130,000 2 2 1,000 1,000 SqFt
110 Gina Drive Dr, Dover Plains, NY, 12522 $185,000 2 2 1,056 1,056 SqFt
21-23 Tinker Town Road, Dover Plains, NY, 12522 $1,950,000 3 1 1,482 1,482 SqFt
56 Northrup Road, Dover Plains, NY, 12522 $2,475,000 4 5 2,412 2,412 SqFt

The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively 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 deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

ByOwner last updated this listing 06/11/2026 @ 07:51

MLS: 996553 LISTED BY: Anna Proctor, Compass Greater NY, LLC 914-238-0676 SOURCE: OneKey MLS

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