Back 27 Old Wagon Road
Off Market

27 Old Wagon Road

Woodstock NY 12498

4
5
6
3080 sq. ft.
152460 sq. ft.
Single-Family
Last sold for $1,315,000
Megan RiosMegan Rios, last sold this property on 18 August 2026 after 403 days on market.

Overview

Just a half mile from the center of Woodstock, this bucolic 3.7-acre compound offers a rare blend of architectural charm, natural beauty, and versatile living. The property includes the main house and two outbuildings, a one-bedroom cottage and a studio with an attached three-bay garage. Bedroom and bath layout described as the primary residence having three bedrooms and three full baths measuring 2200 sq. ft. The detached cottage has one bedroom with one full bath measuring 480 sq.ft and the detached studio has another full bath measuring 400 sq ft. The main house is a light-filled classic Woodstock modern home built around the original Woodstock's artist's cabin. Thoughtfully designed to frame the surrounding forest through expansive glass sightlines, allowing for views of deer, birds, and other wildlife throughout the seasons. Inside, the home showcases unique historical details such as chestnut beams in the dining room, a bluestone fireplace, a built-in library, and a mix of slate, Spanish tile, pine, and oak flooring. The multi-level living area features a lofted tongue-and-groove wood ceiling and five architectural skylights that bring the outdoors in. Upon entry, you're greeted by a bright and inviting sunroom that opens into a formal foyer. Just off the foyer is a room that can serve as a home office, reading nook, or playroom, conveniently located next to a full guest bathroom. This level also features a cozy bedroom and a hallway office nook--perfect for remote work or quiet study. The eat-in kitchen includes a charming breakfast nook that offers serene views of the surrounding landscape and seamlessly flows into the dining room, creating a warm and inviting connection between the spaces. The dining area doubles as a music room, enhanced by vintage wide-plank pine flooring and a wood-burning fireplace that adds warmth and character. Step down into the sunken living room, where high ceilings and built-in bookshelves create a bright, welcoming space ideal for relaxing or entertaining. The primary suite features an en-suite bathroom with Parisian influences, including a bidet and a deep, one-person soaking tub with jacuzzi jets. Sliders walk out to the private multi-level deck and your own private atrium. Just off the main area, a newly designed mason-laid bluestone patio features a seamless transition into an expansive deck, offering the perfect setting for quiet evenings or vibrant dinner parties. The second floor features a loft area, ideal as a TV or family room, providing a comfortable space to relax or entertain. Tucked away for privacy, the second primary suite includes a full bath, creating a serene retreat separate from the main living areas. The one-bedroom cottage evokes the feel of an English guesthouse, with wood floors, a full kitchen and bathroom, and its own dedicated utilities, making it a wonderful space for guests or potential rental income. The detached studio, adjoining the three-car garage, feels like a New York City loft, complete with wide-plank floors, an open-concept layout, a bathroom, and a kitchenette. With its own electric and utilities, the space lends itself well to use as an office, yoga or art studio, or another income-producing rental. The garage offers three bays--two for vehicles and one ideal for workshop or storage use. For decades, this special property has been a gathering place for artists, musicians and writers. The home is designed to inspire and connect, all within minutes of Woodstock's vibrant center. It's an exceptional retreat with comfort, character, and potential in every direction. Please see addendum for recent updates and improvements on the home.

Features

4 bedrooms
5 bathrooms
6 carspaces
3 garage spaces
3080 sq. ft. floor area
152460 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Woodstock over the last 12 months, the estimated median property value of 27 Old Wagon Road is $724.5k.

Median value
$724.5k
Estimated value range
$480k - $1.31m
Median days on market
56
Estimated value trend
-18%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Woodstock. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 27 Old Wagon Road

2026
Sold
$1,315,000
18 Aug 2026 by Megan Rios, of Berardi Realty

Happy sellers in Woodstock

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We have insufficient information to provide an overview of customer satisfaction for Woodstock. Viewing the agent profiles, reviews and sales for Woodstock can provide insights for this location.

Local market activity for 4 bedroom single-family properties in Woodstock

In the last 12 months, 17 four-bedroom single-family properties similar to 27 Old Wagon Road, have been sold.

This represents a 42% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

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