155 Paine Road
Woodstock, Connecticut 06281
- Beds
- 4
- Baths
- 5 | 1
- SqFt
- 4,873
- Acres
- 3.29
- Year Built
- 2006
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
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
Key Facts
- City/Town
- Woodstock
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2006
- Days on Market
- 130 days
- Beds
- 4
- Baths
- 5 full · 1 half
- Living Area
- 4,873 sq ft
- Lot Size
- 3.29 acres
- Garage / Parking
- 3 garage · 10 total
- Property Taxes
- $17,365 / Annually
Market Snapshot
The Woodstock Market
Single Family · trailing 12 months
Active Listings
20
15 under contract
Median List Price
$664,500
20 active listings
Median Closed Price
$435,000
108 sales
Median Days on Market
60
20 active listings
Median $ / Sq Ft
$260
20 active listings
Sale-to-List Ratio
100.0%
108 sales
How this home compares
List Price
$1.65M
vs $664,500 median
2.5× the median
Price / Sq Ft
$339
vs $260 median
30.4% above median
Days on Market
130 days
vs 60 days median
70 days longer than median
Based on 20 active and 108 closed sales (trailing 12 mo) of single family in Woodstock. Source: SmartMLS · As of September 17, 2026.
Location
155 Paine Road, Woodstock, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$8,570
- Property Taxes$1,447
- Insurance$550
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodstock
- Neighborhood
- N/A
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2006
- New Construction
- No/Resale
- Living Area
- 4,873 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Other
- Cooling
- Central Air
- Fireplaces
- 5
- Laundry
- Main Level
- Laundry Location
- Main floorprivate laundry room
- Appliances
- Gas RangeOven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherElectric DryerWine Chiller
- Basement
- FullUnfinished
- In-Law Apartment
- PossibleSecond Floor
- Interior Features
- Audio SystemAuto Garage Door Opener
Exterior & Lot
- Lot Size
- 3.29 acres
- Zoning
- 0
- Garage / Parking
- 3 garage spaces10 total parking spacesAttached GarageDrivewayUnpavedPrivateCrushed Stone
- Waterfront
- Direct waterfront
- Waterfront Details
- PondAccess
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- GuniteHeatedPool HouseSpaSalt WaterIn Ground Pool
- Construction
- Hardie Board
- Color
- White
- Roof
- Shake
- Foundation
- BrickConcrete
- Exterior Features
- BarnLightingHot TubPatioBalconyGarden AreaStableStone WallPaddock
- Lot Description
- TreedFarm LandClearedProfessionally LandscapedRolling
Listing & Financials
- Property Taxes
- $17,365 / Annually
- Days on Market
- 130
- MLS #
- 24174159
- MLS Status
- Under Contract - Continue to Show
- Financing
- FHA,VA,CHFA,USDA
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/17/2026. This information is provided 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 or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/17/2026 at 12:15 AM UTC.