369 Thompson Road
Thompson, Connecticut 06277
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,944
- Acres
- 0.94
- Year Built
- 1814
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
15
18 under contract
Median List Price
$549,000
15 active listings
Median Closed Price
$423,000
98 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per 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
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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.