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369 Thompson Road

Thompson, Connecticut 06277

ACTIVE - NEW$584,900
Beds
4
Baths
3 | 1
SqFt
2,944
Acres
0.94
Year Built
1814
Matt Caiola

Matt Caiola

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About This Home

Step into the Quiet Corner's storied past at this beautifully renovated 1814 Greek Revival and Italianate farmhouse, set on nearly an acre in the heart of the Thompson Hill Historic District, a 550-acre National Register district anchored by the town green. This 4-bedroom, 3.5-bath antique colonial blends original detail with modern comfort, including a grand entry staircase, two fireplace-warmed sitting rooms, a formal dining room, and an eat-in kitchen with stainless appliances that walks out to a private deck. A main-floor bedroom and half bath add flexibility. Upstairs, three bedrooms, two with private ensuites, and a bonus parlor. Outside, a spacious 30x40, two-story, three-bay barn with a workshop opens up real possibilities, from a car enthusiast, hobbyist, extra storage or even a home-based venture. Anyone interested in a B&B, event space, or short-term rental use should confirm zoning with the Town of Thompson. The location is a true draw: minutes from Lord Thompson Manor, a 1918 historic wedding estate, the William Mason House, and ANYA, an acclaimed fine dining destination that draws visitors from across New England. For those who want small-town history, architectural character, and a genuine sense of place, this is a rare opportunity.

Key Facts

City/Town
Thompson
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1814
Days on Market
0 days
Beds
4
Baths
3 full · 1 half
Living Area
2,944 sq ft
Lot Size
0.94 acres
Garage / Parking
3 garage · 4 total
Property Taxes
$4,670 / Annually

Market Snapshot

The Thompson Market

Single Family · trailing 12 months

Median Days on Market

17

15 active listings

Median $ / Sq Ft

$305

15 active listings

Sale-to-List Ratio

101.0%

98 sales

How this home compares

List Price

$584,900

vs $549,000 median

6.5% above median

Price / Sq Ft

$199

vs $305 median

34.8% below median

Days on Market

0 days

vs 17 days median

17 days fresher than median

Based on 15 active and 98 closed sales (trailing 12 mo) of single family in Thompson. Source: SmartMLS · As of August 24, 2026.

Location

369 Thompson Road, Thompson, Connecticut

Property + 9 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,588

per month

  • Principal & Interest$3,004
  • Property Taxes$389
  • Insurance$195
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Thompson
Neighborhood
N/A
County
Windham

Residence

Property Type
Single Family
Style
Colonial
Year Built
1814
New Construction
No/Resale
Living Area
2,944 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Electric
Cooling
Split System
Laundry
Main Level
Appliances
Electric RangeMicrowaveRefrigeratorDishwasher
Basement
FullHatchway Access
In-Law Apartment
No

Exterior & Lot

Lot Size
0.94 acres
Zoning
TCVD
Garage / Parking
3 garage spaces4 total parking spacesBarnPavedOff Street ParkingDrivewaySharedPaved
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Aluminum
Color
White
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
Wrap Around DeckBarn
Lot Description
Level Lot

Listing & Financials

Property Taxes
$4,670 / Annually
Days on Market
0
MLS #
24200678
MLS Status
Active

Similar Properties

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

Listed By

Shiloh Therrien

(774) 230-3781

The Neighborhood Realty Group

(508) 459-1876

Co-Listed By

Pamela Therrien

The Neighborhood Realty Group

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/24/2026. 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 8/24/2026 at 9:45 PM UTC.