276 Chestnut Hill Road Woodstock, NY $ 755,000
276 Chestnut Hill Road
$ 755,000
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Open House 5/24 11am - 2pm
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276 Chestnut Hill Road

Woodstock, NY, 12498
$ 755,000
Bedrooms2 Baths1.0 Sq 1,250

Monthly Estimate*

$ 4,649

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Single Family Home for sale in Woodstock, NY

for $755,000 with 2 bedrooms and 1 full bath. This 1,250 square foot home was built in 1975 on a lot size of 6.01.

Tucked away on six secluded acres just moments from the heart of Woodstock, this enchanting two-bedroom cottage has been impeccably reimagined, blending timeless character with newly curated finishes. Surrounded by towering evergreens, carpets of moss, and fern-lined woodlands, the property creates a peaceful retreat among the trees. A skylit foyer with glass brick wall opens into a dramatic great room where vaulted ceilings, exposed wood beams, and a striking stone fireplace create a warm centerpiece. A wall of windows brings the forest indoors, filling the open living and dining area with natural light and ever-changing seasonal views. The home is defined by carefully considered details throughout. Designer lighting fixtures illuminate the dining and kitchen areas. A beautifully curated kitchen features custom maple cabinetry, rare Inax tile imported from Japan, handcrafted wood pulls by Green River Project and premium Smeg appliances. Two bedrooms sit on opposite ends of the home offering both comfort and privacy. The primary with its own sunroom overlooking the woods. Positioned between the two bedrooms is a thoughtfully appointed bath. Finished with Waterworks tiles and polished nickel fixtures, the spa-like bath features a clawfoot soaking tub and a large tiled walk-in shower with rainfall fixture. Smart Wi-Fi enabled controls for the heating/cooling units makes it easy to manage the home, even while you're away. Beyond the cottage, perennial gardens and a stone-lined path lead to a barrel sauna and a wood-fired Goodland hot tub overlooking the forest. The property also includes a detached garage, carport and a shed — offering a versatile space for storage or creative projects. Just two miles to town, Woodstock offers a vibrant mix of wonderful restaurants, live music, boutiques, swimming holes, hiking, and the creative energy that has made it an enduring cultural destination. A hidden retreat in the woods, this turnkey cottage offers a rare sense of beauty, privacy and quiet charm.

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Open House

5/24/2026 11:00 AM - 2:00 PM
276 Chestnut Hill Road Woodstock, NY
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 755,000

Bedrooms

2

Full Bath

1

Property Type

Single Family

Taxes

$ 9,734

Style

Cottage

Lot Size

6.01

Year Built

1975

Town/City

Woodstock

County/Region

Ulster

MLS | Web ID

1000815

Features
Interior
Interior Amenities Beamed Ceilings Entrance Foyer Tile Counters
Basement Crawl Space
Flooring Hardwood Other Tile
Fireplace Features Wood Burning
Basement Features Crawl Space
Basement (Y/N) N
Fireplace Y/N Y
Half Baths 0
Total Bedrooms 2
Total Baths 1
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General
Sewer Septic Tank
Heating Electric Heat Pump
Cooling Electric
Utilities Electricity Connected
Appliances Dryer Gas Range Refrigerator Tankless Water Heater Washer
Garage Spaces 1
Patio/Porch Features Patio
Architectural Style Cottage
Construction Materials Frame
Year Built 1975
View Trees/Woods
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 5800-027.019-0002-025.000-0000
County Ulster County
Property Type Residential
HOA N
Garage Y/N Y
Other Structures Shed(s)
Total Rooms 6
Full Baths 1
Directions The house is at the end of a shared long private drive. The private drive starts at the stop sign intersection across form Witchtree Rd. House is at the end beyond a wooden gate.
High School Kingston High School
City Woodstock
Senior Community Y/N N
High School District Kingston
Carport Spaces 1
Carport Y/N Y
Elementary School E R Crosby Elementary School
Property Attached Y/N N
Tax Annual Amount 9734.13
Middle/Junior High School M Clifford Miller Middle School
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Kingston
Elementary School District Kingston
Tax Assessed Value 220000
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Exterior
Exterior Amenities Fire Pit
Fencing Fenced
Parking Features Carport Driveway Garage Carport Driveway Garage
Water Source Well
Waterfront Y/N N
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Internal Only
Street Number 1 276
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* Excluded Features
List By
Hailey Kiesewetter

Listing Agent

Upstate Down

Broker

845-516-5123

Contact

Affordability Calculator

$5,460
Per Month
85%
15%
0%
Monthly Principal & Interest
$4,649
Monthly Property Taxes
$811
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4101451 Elementary School
4100906 Middle School
Kingston High School High School
Pricing History
DatePricePrice ChangeDescription
5/20/2026$755,000 Listed Price

Map


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276 Chestnut Hill Road, Woodstock, NY, 12498 is a Single Family Home for sale at $755,000 with 1,250 sqft and a lot size of 6.01. 276 Chestnut Hill Road has 2 bedrooms, 1.0 baths, and was built in 1975. The property's zip code is 12498 which is in Woodstock, NY