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Street View
$499,000
Monthly Est:$2,484
3 Beds
- 2 Baths
2 full baths
1,900sqft
256 Hammond Hl Rd, Dover Plains, NY 12522
$499,000
$2,484/moEst:
Get Pre-Approved
Single Family Residence
Built in 1970
$-- HOA
3 acres lot
$263/sq.ft
Description
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 home 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.
- Houzeo last checked: 9 minutes ago
- Listing updated: September 18, 2026 at 3:53 pm
- Listing Provided by: Anna Proctor (845) 656-0692 | Compass Greater NY, LLC (914) 238-0676
- Source: OneKey MLS-NY as distributed by MLS GRID | MLS#: 996553

Property Details
Status
Pending
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1970
HOA Fees
-
Finished Area
1,900 sqft
Lot Size
3 acres lot
Basement Area
- sqft
MLS Name
OneKey MLS
MLS Number
996553
MLS Status
Pending
Days on Market
180
Cumulative Days on Market
112

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 3
Bathrooms: 2
Interior
Sewer
Septic Tank
Heating
Hydro Air, Oil
Cooling
Central Air
Appliances
Dishwasher, Dryer, Oven, Refrigerator, Washer
Interior Features
First Floor Bedroom, First Floor Full Bath, Built In Features, Cathedral Ceiling(s), Chefs Kitchen, Eat In Kitchen, Kitchen Island, Open Floorplan, Open Kitchen, Primary Bathroom, Recessed Lighting, Washer/dryer Hookup
Flooring
Hardwood
Construction
Year Built
Year Built: 1970
Home type
Single Family Residence
Construction Materials
Block
Architectural Style
Ranch
Utilities & Energy
Basement
Crawl Space
Water Source
Well
Parking Features
Detached, Driveway
Utilities
Cable Available, Cable Connected, Electricity Available, Electricity Connected, Phone Available, Water Available, Water Connected
Laundry Features
Laundry Room
Price History
| Date | Event | Price |
|---|---|---|
08/28/2026 Source: | Pending | $499,000 -5.67% $263/sqft |
05/07/2026 Source: | Listed for Sale | $529,000 $278/sqft |
Nearby Homes
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Based on information from OneKey MLS® through Nov 04, 2026, 12:31AM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 OneKey MLS. All rights reserved.
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