Active

357 Chestnut Hill Road

Woodstock, NY 12498
Mark as Favorite
Bed 2

Bed

Bath 1

Bath

SqFt1,338

Sqft

Acres1.70

Acres(Lot)

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 pri mary 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.

Read More Expand
Tour with a ByOwner Agent

Detail Ic Property Details

Property Type : Residential

Price : $595,000

AD Id : 91100056

MLS Id : 20265197

Beds : 2

Lot Size : 1.70 Acres

Living Area Size : 1,338

Tax Amount : 12867.00

Year Built : 1970

Garage : 1

County : Ulster

  • Map Map

Map

Map What's Nearby

Map Nearby Areas

Feature Features

  • Bedroom Information

    Total beds: 2

    Bathroom Information

    Total Baths: 1 Full Baths: 1

    Room Information

    Rooms Total: 4 Has Basement: Yes Basement: Exterior Entry, Partial, Partially Finished, Storage Space, Unfinished
  • Flooring Information

    Hardwood, Wood
  • Roofing Information

    Shingle
  • Interior Features

    Beamed Ceilings, High Ceilings, Natural Woodwork, Other, See Remarks, Master Downstairs Roof: Shingle Appliances: Built-In Electric Range, Built-In Electric Oven, Built-In Range, Dryer, Dishwasher, Exhaust Fan, Electric Range, Electric Water Heater, Free-Standing Freezer, Free-Standing Refrigerator, Freezer, Oven, Range, Refrigerator, Range Hood, Washer, Washer/Dryer, Water Heater Laundry Features: In Kitchen, Main Level Window Features: Screens
  • Heating & Cooling

    Has Heating: Yes Heating: Exhaust Fan, Fireplace(s), Forced Air Has Cooling: Yes Cooling: Electric

  • Building Information

    Year Built: 1970 Building Area Total: 1338 Construction Materials: Wood Siding Stories: 1 Frontage Length: 257 feet Patio And Porch Features: Enclosed, Front Porch, Patio, Screened, Side Porch, Terrace, Wrap Around Pool Features: None Private Pool: No View: Trees/Woods
  • Exterior Features

    Exterior Features: Other

  • Lot Information

    Main Square Feet: 1.7 Acres Lot Size Acres: 1.7 Lot Size Square Feet: 74052 Lot Description: Irregular Lot, Secluded, Sloped, Sloped Up

  • Listing Price Information

    Listing Price: $595000

  • Tax Information

    Parcel Number: 515800274127 Tax Lot: 27 Tax Block: 1 Annual Tax: $12867 Tax Legal Desc: Liber: 7101, Page: 138

  • Parking Information

    Driveway, Outside, Private, Storage, Workshop in Garage

    Garage Information

    Has Garage: Yes Garage Space: 1

  • School Information

    Elementary School: Crosby K-4
    Junior High School:
    Senior High School:
  • Utility Information

    Natural Gas Available, Electricity Available, Electricity Connected, Natural Gas Not Available, Phone Available, Sewer Not Available, Water Available, Water Connected
  • Location Information

    WaterSource: Private, Well Security Features: Smoke Detector(s)
Sell a home like this and save $35,201 Find out How

How much is this property worth?

Curious about this home's true market value? Use our free Home Evaluation Tool to instantly get a personalized Comparative Market Analysis (CMA) report. Make smarter, data-driven decisions before you buy.

Images
Loading, please wait...

Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
56 Lauren Court, Woodstock, NY, 12498 $2,300,000 3 4 2,613 4.39 Acres
328 John Joy Road, Woodstock, NY, 12498 $569,000 2 2 1,300 --
110 Cottontail Lane, Woodstock, NY, 12498 $539,000 4 3 2,265 0.37 Acre
110 Cottontail Lane, Woodstock, NY, 12498 $539,000 4 3 2,265 0.37 Acre
72 Van Dale Road, Woodstock, NY, 12498 $699,000 3 3 1,991 1.36 Acres
15 Chipmunk Lane, Woodstock, NY, 12498 $915,000 3 3 2,265 1.09 Acres
639 W Saugerties Road, Woodstock, NY, 12498 $2,200,000 3 2 3,530 46.68 Acres
29 Maurizi Lane, Woodstock, NY, 12498 $799,999 4 3 2,372 2.60 Acres
171 Van Dale Road, Woodstock, NY, 12498 $599,000 3 3 1,824 0.93 Acre
5 Downer Lane, Woodstock, NY, 12498 $1,200,000 4 4 3,172 5.85 Acres

The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the Ulster County Board of REALTORS®. IDX information is provided exclusively for consumers' personal, non - commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright ©2026 Ulster County Board of REALTORS®, Inc.

ByOwner last updated this listing 09/09/2026 @ 14:17

MLS: 20265197 LISTED BY: Jacob Miles, Brown Harris Stevens Hudson SOURCE: Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS)

Homes around $595,000

Selling? Save $35,201 when you sell a home like this

Tour with a ByOwner Agent