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155 Paine Road
Woodstock CT 06281 US

$1,650,000

Active Under Contract Listing ID 24174159
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4 bed
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6.00 Bath (5 Full , 1 Half)
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Lot: 3.29 Acres
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Other

$1,650,000

Active Under Contract Listing ID 24174159
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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

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Property Features

  • Facts
  • Lot Size: 3.29 Acres
  • Property Type: Residential
  • Property Sub-type: Other
  • Features
  • Full Bathrooms: 5
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air
  • Exterior Finish: Barn, Lighting, Hot Tub, Patio, Balcony, Garden Area, Stable, Stone Wall, Paddock
  • Additional Features
  • Basement
  • Fireplace
  • Patio
  • Waterfront

School Information

  • School
  • Per Board of Ed(Elementary)
  • Per Board of Ed(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Other
  • listprice: 1650000
  • unparsedaddress: 155 Paine Road
  • postalcity: Woodstock
  • stateorprovince: CT
  • country: US
  • postalcode: 06281
  • bathroomsfull: 5
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 3.29
  • lotsizeunits: Acres
  • lotsizearea: 3.29
  • livingarea: 4873
  • livingareaunits: Square Feet
  • latitude: 41.991235
  • longitude: -71.95475
  • listagentfullname: Sheena Ruggirello
  • listagentemail: sheena.ruggirellos@gmail.com
  • listagentkey: 3yd-CTMLS-RUGGIRES
  • listagentmlsid: RUGGIRES
  • listagentpreferredphone: 8602224734
  • listagentofficephone: 8554500442
  • listofficekey: 3yd-CTMLS-RLBR01
  • listofficemlsid: RLBR01
  • disclaimer: Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: CTMLS
  • yearbuilt: 2006
  • listingcontractdate: 2026-05-09
  • listagenturl: https://www.onereal.com
  • countyorparish: Windham
  • elementaryschool: Per Board of Ed
  • highschool: Per Board of Ed
  • appliances: Gas Range, Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer, Wine Chiller
  • cooling: Central Air
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 10
  • waterfrontyn: True
  • franchiseaffiliation: None
  • interiorfeatures: Audio System, Auto Garage Door Opener
  • exteriorfeatures: Barn, Lighting, Hot Tub, Patio, Balcony, Garden Area, Stable, Stone Wall, Paddock
  • waterfrontfeatures: Pond
  • architecturalstyle: Colonial
  • rooms: Bedroom 1, Bedroom 3, Bathroom 6, Basement, Bedroom 4, Bathroom 5, Bedroom 2, Bathroom 2, Bathroom 3, Bathroom 1, Bathroom 4
  • patioandporchfeatures: Patio
  • basement: Full, Unfinished
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -71.95475, 41.991234
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Real Broker CT, LLC", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"sheena.ruggirellos@gmail.com", "ListBrokerageCity":"Hartford", "ListBrokerageCountry":"US", "ListBrokerageEmail":"ctbroker@therealbrokerage.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Real Broker CT, LLC", "ListBrokeragePhone":"(855) 450-0442", "ListBrokeragePostalCode":"06103-4500", "ListBrokerageStateOrProvince":"CT", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"100 Pearl St., FL 14", "ListBrokerageWebsiteUrl":"https://www.onereal.com", "ListOfficeAddress1":"100 Pearl Street, 14th Floor ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"RLBR01", "ListOfficeCity":"Hartford", "ListOfficeCountry":"US", "ListOfficeEmail":"Membership@therealbrokerage.com", "ListOfficePostalCode":"06103", "ListOfficeStateOrProvince":"CT", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Woodstock, CT", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/155-Paine-Rd_Woodstock_CT_06281_M33140-59791?f=listhub&s=CTMLS&m=24174159&c=rexren", "MLSModificationTimestamp":"2026-05-13 19:52:57", "Neighborhoods":[], "PostalCode":null, "RoomCount":10, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":16892, "TaxDescription":null, "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 5/31/2026 12:53:52 PM GMT
Source Updated Date: 6/4/2026 12:54:43 AM GMT

Courtesy of: Sheena Ruggirello, Real Broker CT, LLC, sheena.ruggirellos@gmail.com

Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.