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369 Thompson Road

Thompson, Connecticut 06277

ACTIVE$584,900

Reduced from $594,900

Beds
4
Baths
2 | 1
SqFt
2,944
Acres
0.94
Year Built
1814
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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4-Car GaragePrice Reduced

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

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

Property + 8 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,566

per 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

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Listed By

Sheena Ruggirello

(860) 222-4734

Real Broker CT, LLC

(855) 450-0442

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.