155 Paine Rd

Woodstock, CT 06281

$1,650,000
Price
4
Beds
4,873 Sq. Ft.
$339 / Sq. Ft.
4,873
Sq. Ft.
$339
per Sq. Ft.
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Under Contract - Continue To Show
Under Contract - Continue To Show
an aerial view of residential houses with outdoor space and street view
a view of a swimming pool with a patio
a kitchen with kitchen island granite countertop a sink counter top space and a center island
a kitchen with granite countertop a sink a window and cabinets
a view of a dining room with furniture window and wooden floor
a dining room with furniture window and wooden floor
a view of a livingroom with furniture window and wooden floor
a living room with furniture window and wooden floor
a living room with furniture and a fireplace
a living room with furniture fireplace and flat screen tv
a large kitchen with kitchen island a sink counter space and living room view
a kitchen with stainless steel appliances granite countertop a sink and a window
a view of a dining room with furniture and chandelier
a bathroom with a tub sink and mirror
a view of an entryway with a livingroom
a bedroom with a bed and a view of en suite bathroom
a bathroom with a toilet a sink and mirror
a view of kitchen with furniture and wooden floor
a view of a hallway with wooden floor and stairs
a bathroom with a sink a toilet and mirror
a living room with furniture and a fireplace
a bedroom with furniture and a fireplace
a spacious bedroom with a bed and a desk
a view of an house with outdoor space and parking
a front view of a house with a garden

Description

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...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
  1. Listed by Sheena Ruggirello • Real Broker CT, LLC
    P: (860)-222-4734 C: (860)-222-4734 sheena.ruggirellos@gmail.com

Property Details for 155 Paine Road

Basement Description
Full, Unfinished
Direct Waterfront
Yes
Garages Number
3
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Attached Garage, Driveway, Unpaved
Swimming Pool
Yes
LISTING UPDATED: 06/29/2026 07:01 AM

Property Details for 155 Paine Road

StatusUnder Contract - Continue To Show
MLS #24174159
Days on Market52
Taxes$17,365 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built2006
Lot Size3.29 AC / 143,312 SF
CountyWindham County
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Location

Listing Courtesy of Real Broker CT, LLC, Sheena Ruggirello
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Building Information for 155 Paine Road

Stories-Year Built2006Building Size-Lot Size3.29 AC / 143,312 SF

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$9,669 per month

30 year fixed, 6.36% Interest

Principal and Interest

$8,222

Property Taxes

$1,447

HOA Dues

$0

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Property Information for 155 Paine Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Paine district rd to Paine rd long driveway.
  • Elementary School: Per Board of Ed
  • Flood Zone: No
  • High School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • Latitude: 41.989714
  • Longitude: -71.956441
  • Middle Jr High School: Per Board of Ed
  • State: Connecticut
Parking
  • Parking Total Spaces: 10
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2026-June 2027
  • Property Tax: $17,365
Interior and Exterior Features
Exterior Features
  • Exterior Features: Barn, Lighting, Hot Tub, Patio, Balcony, Garden Area, Stable, Stone Wall, Paddock
  • Pool Description: Gunite, Heated, Pool House, Spa, Salt Water, In Ground Pool
  • Waterfront Description: Pond, Access
Interior Features
  • Appliances Included: Gas Range, Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer, Wine Chiller
  • Attic Description: Heated, Storage Space, Finished, Walk-up
  • Cooling System: Central Air
  • Heat Type: Other
  • Attic YN: Yes
  • Fireplaces Total: 5
  • Interior Features: Audio System, Auto Garage Door Opener
  • Laundry Room Info: Main Level
  • Laundry Room Location: Main floor, private laundry room
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Country,Island,Pantry,Wide Board Floor
  • Room Length: 30.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 11.0
Room 2
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Combination Liv/Din Rm,Fireplace,French Doors,Wide Board Floor
  • Room Length: 19.6
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 15.0
Room 3
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Fireplace
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 15.0
Room 4
  • Room Entry Order: 4
  • Room Features: 9 ft+ Ceilings,Balcony/Deck,Dressing Room,Full Bath,Whirlpool Tub,Wide Board Floor
  • Room Length: 27.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 15.0
Room 5
  • Listing Key: 515955236FFB631AE063E201100A086D
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,Bedroom Suite,Ceiling Fan,Full Bath,Wide Board Floor
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 6
  • Room Entry Order: 6
  • Room Features: 9 ft+ Ceilings,Bedroom Suite,Ceiling Fan,Full Bath,Wide Board Floor
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 7
  • Room Entry Order: 7
  • Room Features: Vaulted Ceiling,Balcony/Deck,Bedroom Suite,Ceiling Fan,Fireplace,French Doors
  • Room Length: 18.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 8
  • Room Entry Order: 8
  • Room Features: 9 ft+ Ceilings,French Doors,Wide Board Floor
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Study
  • Room Width: 17.0
Room 9
  • Listing Key: 515955236FFB631AE063E201100A086D
  • Room Entry Order: 9
  • Room Features: Built-Ins,Full Bath,Wide Board Floor,On 3rd Floor
  • Room Level: Upper
  • Room Type: Rec/Play Room
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Driveway Type: Private, Crushed Stone
  • Exterior Siding: Hardie Board
  • Foundation Type: Brick, Concrete
  • New Construction Type: No/Resale
  • Roof: Shake
  • Year Built: 2006
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Second Floor
  • In Law Apartment: Possible
  • Living Area SQFT Per Public Records: 4873
Lot Information
  • Lot Description: Treed, Farm Land, Cleared, Professionally Landscaped, Rolling
  • Parcel Number: 2493389
  • Sq Ft Est Heated Above Grade: 4873.0
  • Sq Ft Total: 4873.0
  • Zoning: 0
Utilities
  • Energy Features: Generator, Geothermal Heat
  • Hot Water Description: Other
  • Radon Mitigation Air: Yes
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Estimated Annual Heat Cost: 0
  • Occupied By: Owner

Public Records for 155 Paine Road

Taxable ValueLand$52,400Additions$639,600Total$692,000
Tax Record2024$16,892 ($1,408 / month)
Home Facts
Beds4Baths5.5Total Finished SqFt4,873 SqFtAbove Grade Finished SqFt4,873 SqFtStories2Lot Size143,312 SqFtStyleSingle Family ResidenceYear Built2006Zoning0CountyNORTHEASTERN CONNECTICUTAPNWSTK M:5165 B:08 L:04-5Fireplace TypeHas Fireplace

Schools near 155 Paine Road

This home is within Woodstock School District.
Rating
School
Type
Grades
Distance
Woodstock Elementary School
Public - PK to 4
Woodstock Middle School
Public - 5 to 8
Rating
School
Distance
Woodstock Elementary School
PublicPK to 4

Woodstock Middle School
Public5 to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Real Broker CT, LLC, Sheena Ruggirello

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.