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155 Paine Road

Woodstock, Connecticut 06281

PENDING$1,650,000
Beds
4
Baths
5 | 1
SqFt
4,873
Acres
3.29
Year Built
2006
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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WaterfrontPool3-Car Garage5 Fireplaces

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

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

Property + 6 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$10,567

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Sheena Ruggirello

(860) 222-4734

Real Broker CT, LLC

(855) 450-0442

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.