369 Thompson Road
Thompson, Connecticut 06277
Reduced from $594,900
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,944
- Acres
- 0.94
- Year Built
- 1814
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
In the heart of Thompson Hill, step into history with the Jeremiah Olney House owned by the famous banker Jeremiah Olney in 1860, with its significant Greek Revival and Italianate features. This stunning 4-bed, 3.5-bath colonial farmhouse sits on nearly an acre of picturesque land and has been completely renovated. Overflowing with character, this home blends classic charm with modern convenience, offering spacious living areas and timeless architectural details. The grand entryway welcomes you with a beautiful original staircase, setting the tone for the elegance found throughout. The main floor features two inviting sitting rooms with original fireplaces, a formal dining room, and an eat-in kitchen with stainless steel appliances and a walk-out to the private deck-perfect for entertaining. A main-floor bedroom and half bath provide convenience and flexibility. Upstairs, the second floor boasts three well-appointed bedrooms, two of which feature private ensuites, plus an additional parlor that offers cozy charm and versatility. The partially finished attic on the third floor presents the perfect space for a playroom, studio, or creative retreat. Outside, a spacious two-story barn with three bays and a workshop offers endless opportunities-ideal for hobbyists, storage, or even a small business venture. This one-of-a-kind historic home is waiting for its next chapter!
Key Facts
- City/Town
- Thompson
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1814
- Days on Market
- 60 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,944 sq ft
- Lot Size
- 0.94 acres
- Garage / Parking
- 4 garage · 4 total
- Property Taxes
- $4,670 / Annually
Market Snapshot
The Thompson Market
Single Family · trailing 12 months
Active Listings
11
24 under contract
Median List Price
$480,000
11 active listings
Median Closed Price
$400,000
90 sales
Median Days on Market
46
11 active listings
Median $ / Sq Ft
$271
11 active listings
Sale-to-List Ratio
100.9%
90 sales
How this home compares
List Price
$584,900
vs $480,000 median
21.9% above median
Price / Sq Ft
$199
vs $271 median
26.6% below median
Days on Market
60 days
vs 46 days median
14 days longer than median
Based on 11 active and 90 closed sales (trailing 12 mo) of single family in Thompson. Source: SmartMLS · As of July 28, 2026.
Location
369 Thompson Road, Thompson, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,982
- 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
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Electric
- Cooling
- Split System
- Laundry
- Main Level
- Appliances
- Electric CooktopOven/RangeMicrowaveRefrigeratorFreezer
- Basement
- FullHatchway Access
- Additional Rooms
- Foyer
Exterior & Lot
- Lot Size
- 0.94 acres
- Zoning
- TCVD
- Garage / Parking
- 4 garage spaces4 total parking spacesDetached GaragePavedOff Street ParkingDrivewayShared
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Aluminum
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- ClearedOpen Lot
Listing & Financials
- Property Taxes
- $4,670 / Annually
- Days on Market
- 60
- MLS #
- 24179305
- MLS Status
- Active
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:01 AM UTC.