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$599,900

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,944 Sq. Ft.
  • 4 Car Garage
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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!

Full Property Details for 369 Thompson Rd

General

  • Price: $599,900
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24120638
  • Updated: 1/1/2026
  • Added to Site: 148 day(s) ago

Interior

  • Number of Rooms: 11
  • Rooms/Areas: Foyer
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Electric Cooktop, Oven/Range, Microwave, Refrigerator, Freezer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Remodeled, Full Bath, Stall Shower, Upper
  • Bedroom 1: Bedroom, Main
  • Bedroom 2: Bedroom - Walk-In Closet, Upper
  • Bedroom 3: Bedroom - Remodeled, Full Bath, Upper

Other Rooms

  • Living Room: Living Room - Remodeled, 9 ft+ Ceilings, Fireplace, Main
  • Family Room: Family Room - Remodeled, Beams, Main
  • Eat In Kitchen: Eat-In Kitchen - Remodeled, Vaulted Ceiling, Granite Counters, Dining Area, Isl, Main
  • Dining Room: Dining Room - Remodeled, 9 ft+ Ceilings, Built-In Hutch, Fireplace, Sliders, Main
  • Den: Den - On 3rd Floor, Other
  • Library: Library - Remodeled, Fireplace, Upper
  • Laundry: Main Level

Exterior

  • Color: White

Parking

  • Garage: Yes
  • Garage Spaces: 4
  • Total Spaces: 4
  • Parking: Detached Garage, Paved, Off Street Parking, Driveway

Location

  • County: Windham
  • Driving Directions: GPS Friendly

School Information

  • Elementary School: Per Board of Ed
  • Middle School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: Split System
  • Heating Type: Heat Pump, Electric
  • Heating Fuel: Electric
  • Water Heater: Electric, Tank Size Unknown

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial, Antique
  • Construction Status: No/Resale
  • Exterior Const.: Aluminum
  • Basement Desc.: Full, Hatchway Access
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,944
  • Above Ground: 2,944 Sq. Ft.
  • Year Built: 1814

Lot Features

  • Lot Size (Acres): 0.94
  • Driveway/Sidewalk: Shared
  • Zoning: TC80
  • Lot Description: Cleared, Open Lot

Financial Considerations

  • Assessment Amount: $245,800
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1721757

Listed by Real Broker CT, LLC, Sheena Ruggirello

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Listing agent

— 369 Thompson Rd —

  • Sheena Ruggirello

    Real Broker CT, LLC

Agent Contact: (860) 222-4734 Office Contact: (855) 450-0442

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 369 Thompson Rd

School District:Thompson School District
NameGradesDistance
Mary R. Fisher Elementary School
785 Riverside Dr., Thompson, CT 06255
PK-42.2 mi
Thompson Middle School
785 Riverside Dr., Thompson, CT 06255
5-82.2 mi
Tourtellotte Memorial High School
785 Riverside Dr., Thompson, CT 06255
9-122.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 369 Thompson Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/25/2025
Price Reduced
$599,900
-2.44%
MLS
8/20/2025
Listed
$614,900
192.81%
MLS
11/07/2002
Sold
$210,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 369 Thompson Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$4,670
-4%
$245,800
42%
2023
$4,869
8%
$173,200
—
2023
$4,503
4%
$173,200
—
2022
$4,333
—
$173,200
—
2021
$4,321
-19%
$173,200
-22%
2020
$5,365
8%
$221,400
23%
2019
$4,987
—
$179,700
—
2018
$4,987
6%
$179,700
—
2017
$4,683
—
$179,700
—
2016
$4,683
5%
$179,700
—
2015
$4,457
2%
$179,700
-6%
2014
$4,350
3%
$190,200
—
2012
$4,222
—
$190,200
—
2011
$4,222
—
$190,200
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 369 Thompson Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Real Broker CT, LLC, Sheena Ruggirello

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369 Thompson Road, Thompson, CT 06277 (MLS# 24120638) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 369 Thompson Road is currently listed for $599,900 and was received on August 20, 2025. Want to learn more about 369 Thompson Road? Do you have questions about finding other Single Family real estate for sale in Thompson? You can browse all Thompson real estate or contact a Coldwell Banker agent to request more information.

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