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Rare investment opportunity in Woodstock: a collection of five unique cottages on six wooded acres located just minutes from the Village's vibrant shops, dining, and nightlife. Each home boasts a distinct personality and peaceful forest views, and all five have been successfully rented with a combination of short- and long-term tenants. Possibilities include renting all five cottages or living in one while renting the other four. Another option is to create a warm and inviting 5-cottage compound for group living. Imagine enjoying the Woodstock lifestyle with loved ones just a door-knock away. For a writer, artist, or home-business owner, perhaps one or more of the cottages could be used as a studio or office separate from home. Cottage 1 is a delightful two bedroom/one bath with a fireplace and Craftsman kitchen. Cottage 2, with one bed and one bath, was reimagined and fully renovated in 2024. Cottage 3 is peak contemporary treehouse: a stunning two bedroom/two bath, featuring dramatic windows, balcony, and fireplace, with a spiral staircase up to the primary bedroom. Bright and airy Cottage 4 is a cheerful one bedroom/two bath that is wheelchair-accessible. The first thing you'll notice about Cottage 5 is the cool roofline with a clerestory that fills the living area with light. When not relaxing at home, there's plenty to do in the area: hiking, swimming, skiing, listening to live music, visiting art galleries and antique shops, dining and shopping in Woodstock and beyond. The bus from NYC stops near Woodstock's Village Green. Amtrak is across the Hudson in the hamlet of Rhinecliff. NYC's George Washington Bridge is about 100 miles away. The short-term rental license conveys. The 2025 cap rate with all cottages rented (either short-term or long-term) was 7%, and for 2024 it was closer to 10%. Financials and rental history are available. If you're seeking an investment property, live-work dream spot, or sweet group compound in Woodstock, consider viewing this fantastic 6-acre, 5-cottage property in beautiful, famous, ever-inspiring Woodstock.
This mortgage calculator can be used to figure out monthly payments of a home mortgage loan, based on the home's sale price, the term of the loan desired, buyer's down payment percentage, and the loan's interest rate.
Listing information last updated on June 16th, 2026 at 8:20am EDT.