155 Paine Road, Woodstock, Connecticut

$1,650,000

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4

Beds

6

Baths

4,873

Square feet

3.29

Acres

About 155 Paine Road

Set on a breathtaking stretch of rolling countryside in historic Woodstock, this extraordinary Federal Colonial reproduction blends timeless New England craftsmanship with modern luxury across a remarkable multi-parcel estate. Approached by a long winding driveway, the home is perfectly positioned to capture sweeping pastoral views, overlooking fenced fields, hay meadows, and distant farmsteads. Designed with exceptional attention to detail, the residence features a handcrafted artisan kitchen with Wolf and Sub-Zero appliances, soapstone and marble countertops, cooling drawers, wine chillers, and sun-filled gathering spaces framed by French doors and endless views. The home offers five Rumford fireplaces, luxurious bedroom suites each with private baths, a stunning primary suite with reading nook, spa-inspired bath, custom wardrobes, and private deck overlooking the heated gunite pool, pool house, stone patio, and outdoor fireplace. A dramatic central staircase leads through all three finished levels, including a third-floor bonus retreat with full bath, while an elegant private in-law suite offers its own entrance, living area, fireplace, and full bath and the home is geothermal. Complementing the property is a remarkable reconstructed 1800s post-and-beam barn featuring eight stalls, lofts, hay and equipment storage, paddocks, turnouts, hydrants, and 200-amp electrical service-ideal for equestrian use, entertaining, events, hobby farming, endless country living at its finest

Features of 155 Paine Road

MLS® # 24174159
Price $1,650,000
Bedrooms 4
Bathrooms 6.00
Full Baths 5
Half Baths 1
Square Footage 4,873
Acres 3.29
Type Single Family For Sale
Style Colonial
Status Under Contract - Continue to Show

Community Information

Address 155 Paine Road
Area N/A
City Woodstock
County Windham
State Connecticut
Zip Code 06281

Amenities

Features Generator, Geothermal Heat
Parking Spaces 10
Parking Attached Garage, Driveway, Unpaved
# of Garages 3
Is Waterfront Yes
Waterfront Pond, Access
Has Pool Yes
Pool Gunite, Heated, Pool House, Spa, Salt Water, In Ground Pool

Interior

Interior Features Audio System, Auto Garage Door Opener
Appliances Gas Range, Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer, Wine Chiller
Heating Other
Cooling Central Air
Fireplace Yes
# of Fireplaces 5
Has Basement Yes
Basement Full, Unfinished

Exterior

Exterior Hardie Board
Exterior Features Barn, Lighting, Hot Tub, Patio, Balcony, Garden Area, Stable, Stone Wall, Paddock
Lot Description Treed, Farm Land, Cleared, Professionally Landscaped, Rolling
Roof Shake
Foundation Brick, Concrete

School Information

Elementary Per Board of Ed
Middle Per Board of Ed
High Per Board of Ed

Additional Information

Date Listed May 9th, 2026
Days on Market 124
RE / Bank Owned No

Listing Details

OfficeReal Broker CT, LLC

Listing Map

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Listing information last updated on September 10th, 2026 at 12:57pm EDT.