This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/21
$499,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/21
Property 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.
Full Property Details
Full Property Details for 256 Hammond Hill Rd
General
- Price: $499,000
- Taxes: $6,106
- Status: Active
- Type: Single Family
- Source: Long_Island
- MLS ID: 996553
- Updated: 5/18/2026
- Added to Site: 68 day(s) ago
Interior
- Number of Rooms: 10
- 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
- Fireplace: Yes
- Number of Fireplaces: 2
- Appliances: Dishwasher, Dryer, Oven, Refrigerator, Washer
- Laundry Facilities: Yes
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Laundry Room
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 6
- Parking Features: Detached, Driveway
Location
- County: Dutchess County
School Information
- High School District: Dover
- Elementary School: Dover Elementary School
- Middle School: Dover Middle School
- High School: Dover High School
Heating & Cooling
- Central air: Yes
- Cooling Type: Central Air
- Heating Type: Hydro Air, Oil
Utilities
- Sewer: Septic Tank
- Water: Well
- Utility Description: Cable Available, Cable Connected, Electricity Available, Electricity Connected, Phone Available, Water Available, Water Connected
Structural Information
- Architectural Style: Ranch
- Detached/Attached: Detached
- Construction: Block
- Basement: Yes
- Basement Desc.: Crawl Space
- Sq. Ft. Source: Public Records
- Year Built: 1970
Lot Features
- Lot Size (Acres): 3
- Lot Size (Sq. Ft.): 130,680
Financial Considerations
- Tax Amount: $6,106
Disclosures and Reports
- Special Conditions: None
- Property ID: 135889-6963-00-573881-0000
Listed by Compass Greater NY, LLC
Get Pre-Approved Today
Schools
Schools serving 256 Hammond Hill Rd
School District:Dover Union Free School District
| Name | Grades | Distance |
|---|---|---|
Dover Elementary School 9 School Street, Dover Plains, NY 12522 | 3-5 | 2.1 mi |
Wingdale Elementary School 6413 State Route 55, Wingdale, NY 12594 | K-2 | 7.6 mi |
Dover Middle School, Dover Plains, NY 2368 New York 22, Dover Plains, NY 12522 | 6-8 | 5 mi |
Dover High School, Dover Plains, NY 2368 New York 22, Dover Plains, NY 12522 | 9-12 | 5 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 256 Hammond Hill Rd
Date
Details
Price
Change
Source
5/18/2026
Price Reduced
$499,000
-5.67%
MLS
5/07/2026
Listed
$529,000
33.92%
MLS
10/06/2023
Sold
$395,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 256 Hammond Hill Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,048
33%
$257,100
—
2024
$4,550
20%
$257,100
5%
2016
$3,796
26%
$245,400
—
2020
$3,002
-22%
$245,400
—
2018
$3,858
-1%
$245,400
—
2017
$3,916
-1%
$245,400
—
2016
$3,970
32%
$245,400
17%
2015
$3,005
-31%
$210,000
—
2015
$4,365
—
$210,000
—
2013
$4,365
—
$210,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 256 Hammond Hill Rd
256 Hammond Hill Road, Dover Plains, NY 12522 (MLS# 996553) is a Single Family property with 3 bedrooms and 2 full bathrooms. 256 Hammond Hill Road is currently listed for $499,000 and was received on May 07, 2026. Want to learn more about 256 Hammond Hill Road? Do you have questions about finding other Single Family real estate for sale in Dover Plains? You can browse all Dover Plains real estate or contact a Coldwell Banker agent to request more information.
