357 Chestnut Hill Road Woodstock, NY $ 595,000
357 Chestnut Hill Road
$ 595,000
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357 Chestnut Hill Road

Woodstock, NY, 12498
$ 595,000
Bedrooms2 Baths1.0 Sq 1,338

Monthly Estimate*

$ 3,757

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Single Family Home for sale in Woodstock, NY

for $595,000 with 2 bedrooms and 1 full bath. This 1,338 square foot home was built in 1970 on a lot size of 1.7.

A STORYBOOK WOODSTOCK RETREAT IN THE WOODS Some homes provide shelter; others provide sanctuary. 357 Chestnut Hill Road is a sanctuary in the woods--a soulful Woodstock retreat where sunlight spills through skylights, pine glows underfoot, and the forest seems to lean in and whisper, ''stay awhile.'' Set on 1.6 wooded acres with approximately 257 feet of road frontage, this enchanting red-clad hideaway has been treasured by one close family since 1970. Follow the gravel drive beneath a leafy canopy and the home gradually reveals itself among the trees, its warm wood exterior appearing almost organically from the landscape. Secluded without feeling isolated, it captures the creative, carefree spirit that has long made Woodstock irresistible. Inside, 1,338 square feet includes a primary bedroom, a bath, a kitchen, a wonderfully versatile loft, and the home's showpiece: a spacious, cozy living room where an exposed beamed-wood ceiling creates an architectural rhythm overhead, while skylights pour pools of daylight across pine floors below. Windows frame the surrounding woodland. A characterful brick fireplace anchors it all. On crisp Catskills evenings, the hearth becomes the heart of the house--a natural gathering place for conversation, contemplation, and fireside nights. Rustic textures, warm woods, and natural light lend the room an atmosphere at once dramatic and deeply comfortable. The adjoining kitchen and dining area anchor the country cabin's soul with wood cabinetry, exposed beams, a vaulted ceiling, and an overhead skylight. Equipped with a refrigerator, range/oven, dishwasher, and washer/dryer, it is an inviting, unpretentious space for everything from pancakes at sunrise to pasta and pinot after a day exploring. And then there is the porch! Wrapping around two sides of the kitchen, the sprawling screened porch creates an irresistible indoor-outdoor area suspended within the trees. Here, the forest becomes the wallpaper and birdsong the soundtrack. Rain can patter overhead, leaves can rustle beyond the screens, and summer evenings can linger long after the sun disappears. The upper loft adds an unexpected dimension to the home's mostly single-level layout. Wrapped in warm wood, this flexible aerie can readily accommodate an additional sleeping space and a home office, library, studio, meditation area, or creative escape. Space creates possibility, and possibility gives a home room to evolve. Four split-system units add modern comfort, while a 260-square-foot partial basement provides additional utility. The house's roof was replaced in 2020. Outside, the property becomes a private woodland world. Mature trees tower overhead, sunlight dapples the forest floor, and the home's distinctive red exterior provides a warm counterpoint to the seemingly endless green. The gently winding gravel drive continues uphill to a particularly valuable feature: an oversized detached garage. With its dedicated entrance, windows, and loft storage above, the garage offers far more than parking. Think workshop, equipment storage, hobby headquarters, or simply the rare luxury of having room for all the things that make country life more enjoyable. Its roof was replaced in 2023. Yet the real luxury here cannot be quantified by acreage or square footage. It is privacy, peace, and place. For more than half a century, one family has returned to this home, lovingly cared for it, gathered within it, and called it their retreat. That continuity gives 357 Chestnut Hill Road something no renovation can manufacture: soul. The house does not ask to be something it isn't; its weathered woods, exposed beams, skylights, fireplace, loft, porch, and forest setting tell an authentic story of Woodstock country living--and invite a new owner to write its next chapter. Retreat becomes refuge; refuge becomes home; and every great story needs a place to begin--make 357 Chestnut Hill Road the beginning of yours.

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Single Family Active

Price

$ 595,000

Bedrooms

2

Full Bath

1

Property Type

Single Family

Taxes

$ 12,867

Style

Contemporary

Lot Size

1.7

Year Built

1970

Town/City

Woodstock

County/Region

Ulster

MLS | Web ID

20265197

Features
General
Sewer Septic Tank
Heating Fireplace(s) Forced Air
Cooling Electric
Utilities Electricity Available Electricity Connected Natural Gas Not Available Phone Available Sewer Not Available Water Available Water Connected
Roof Shingle
Appliances Water Heater Washer/Dryer Washer Refrigerator Range Hood Range Oven Freezer Free-Standing Refrigerator Free-Standing Freezer Exhaust Fan Electric Water Heater Electric Range Dryer Dishwasher Built-In Range Built-In Electric Range Built-In Electric Oven
Zoning R3
Garage Spaces 1
Patio/Porch Features Enclosed Front Porch Patio Screened Side Porch Terrace Wrap Around
Architectural Style Contemporary
Pool Features None
Security Features Smoke Detector(s)
Construction Materials Wood Siding
Year Built 1970
View Trees/Woods
Stories Count 1
Township Woodstock
Levels One and One Half
Property Subtype Single Family Residence
County Ulster
New Construction false false
Property Type Residential
Attached Garage false
Garage Y/N true
Other Structures Garage(s) Storage Workshop
Total Rooms 4
Full Baths 1
Status Active
City Woodstock
High School District Kingston Consolidated
Zoning Description low-density residential district
MLS Area Woodstock
Lot Size Units Acres
Lot Size Square Feet 74052
Elementary School Crosby K-4
Tax Annual Amount 12867
Property Condition Fixer
MLS Area Minor Woodstock
Structure Type Cabin House
Standard Status Active
Tax Assessed Value 290800
Tax Lot 27
Legal Description Liber: 7101 Page: 138
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Interior
Interior Amenities Beamed Ceilings High Ceilings Natural Woodwork Other See Remarks
Basement Exterior Entry Partial Partially Finished Storage Space Unfinished
Flooring Hardwood Plank Wood
Basement (Y/N) true
Air Conditioning Y/N true
Heating Y/N true
Window Features Screens
Above Grade Finished Area 1338
Half Baths 0
Laundry Features In Kitchen Main Level
Total Bedrooms 2
Below Grade Finished Area 260
Total Baths 1
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Exterior
Exterior Amenities Other
Fencing None
Parking Features Private Storage Workshop in Garage Outside Driveway
Lot Features Irregular Lot Secluded Sloped Sloped Up
Water Source Well
Lot Size Area 1.7
Foundation Details Concrete Perimeter
Building Area Total 1338
Lot Size Acres 1.7
Road Surface Type Asphalt Gravel
Road Frontage Type Town
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* Excluded Features
List By
Jacob Miles

Listing Agent

Brown Harris Stevens Hudson

Broker

jacob@miles.me

Email

Affordability Calculator

$4,829
Per Month
78%
22%
0%
Monthly Principal & Interest
$3,757
Monthly Property Taxes
$1,072
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% 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
4645949 Elementary School
0 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
9/8/2026$595,000 Listed Price

Map


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357 Chestnut Hill Road, Woodstock, NY, 12498 is a Single Family Home for sale at $595,000 with 1,338 sqft and a lot size of 1.7. 357 Chestnut Hill Road has 2 bedrooms, 1.0 baths, and was built in 1970. The property's zip code is 12498 which is in Woodstock, NY