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Residential Land with Home for Sale in Woodstock, New York

27 Old Wagon Rd, Woodstock, NY 12498

$1,295,000
3.65 acres
Active
$55k drop
Est $7,290/mo

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.

3,080
Sq feet
4
Beds
5
Full baths
1978
Built

Location

Street address
27 Old Wagon Rd
Community
Woodstock
School district
Onteora Central School District
Elevation
574 feet
Coordinates
42.0347, -74.1181

Directions

Tannery Brook to LEFT onto Millstream to RIGHT onto Old Wagon Road. Home will be on the left, see sign.

Property details

Acreage
3.65 acres
Zoning
R3
MLS #
UCMLS 20252879
Posted

Property taxes

Recent
$11,340 - 27.14-2-17

Parcels

  • 27.14

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Lot

Features
Back Yard, Front Yard, Gentle Sloping, Landscaped, Private, Wooded

Exterior

Parking
Driveway, Garage, Off Street
Pool
Deck, Patio
Structures
Greenhouse, Storage
Features
Garden, Lighting, Private Yard

Structure

Style
Contemporary
Stories
2
Basement
Crawl Space, Partial, Unfinished
Water
Well
Sewer
Septic Tank
Heating
Baseboard, Electric, Oil
Cooling
Ceiling Fan(s), Wall/Window Unit(s), Window Unit(s)
Materials
Board & Batten Siding, Frame, Vertical Siding, Wood Siding
Roof
Asphalt, Built-Up, Membrane, Rubber
Windows
Double Pane Windows, Insulated Windows, Skylight(s), Storm Window(s)

Interior

Room Count
11
Rooms
Basement, Bathroom x 5, Bedroom x 4, Dining Room, Family Room
Flooring
Carpet, Ceramic Tile, Tile, Wood
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Features
Beamed Ceilings, Bidet, Bookcases, Built-In Features, Ceiling Fan(s), Eat-In Kitchen, Entrance Foyer, High Ceilings, High Speed Internet, Primary Downstairs, Track Lighting, Vaulted Ceiling(s), Walk-In Closet(s)

Nearby schools

NameLevelDistrictDescription
Woodstock K-3ElementaryOnteora Central School District

Listing history

DateEventPriceChangeSource
Oct 25, 2025Back on market$1,295,000UCMLS
Oct 10, 2025Under contract$1,295,000UCMLS
Oct 4, 2025Price drop$1,295,000$55,000 -4.1%UCMLS
Aug 21, 2025Price drop$1,350,000$100,000 -6.9%UCMLS
July 10, 2025New listing$1,450,000UCMLS
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This 3.65-acre property is located at 27 Old Wagon Rd in Woodstock, NY 12498. The property is available for sale for $1,295,000. It has a 3,080 sq ft 4 bedroom, 5 bath house built in 1978.

Checked 9 mins ago — Updated

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