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357 Chestnut Hill Road, 
Woodstock, NY 12498

$595,000


2

Beds


1

Bath


1,338

Sq Ft


Single Family

Active

Listed by

Jacob Miles

Brown Harris Stevens Hudson

518-828-0181

Last updated:

September 15, 2026, 01:06 AM

MLS#

20265197

Source:

NY MLSUC

About This Home

357 Chestnut Hill Road

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.

Home Facts

Single Family

1 Bath

2 Bedrooms

Built in 1970

Price Summary

595,000

$444 per Sq. Ft.

MLS #:

20265197

Last Updated:

September 15, 2026, 01:06 AM

Added:

8 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

2

Bathrooms

Total Bathrooms:

1

Full Bathrooms:

1

Interior

Living Area:

1,338 Sq. Ft.


Structure

Structure

Architectural Style:

Contemporary

Building Area:

1,338 Sq. Ft.

Year Built:

1970


Lot

Lot Size (Sq. Ft):

74,052


Finances & Disclosures

Finances

Price:

$595,000

Price per Sq. Ft:

$444 per Sq. Ft.

Source:NY MLSUC
The information being provided by Hudson Valley Catskill Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Hudson Valley Catskill Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.