309 Oleary Road

Windham County CT 06277

2478 sq. ft.

2.03 ac.

Single-Family

Last sold for $542,000

Jared Meehan, last sold this property on 17 August 2026 after 83 days on market.

Overview

OFFERS DUE 5/30 8PM. Welcome to 309 O'Leary Rd in Thompson, CT, a spacious & versatile property offering 1,400+ SF of main-level living plus 1,000+ SF in the finished lower-level in-law apartment! The main level features a dramatic living room w/ soaring vaulted ceilings that opens to a bright 4-season sunroom, creating an impressive flow of natural light & usable living space. Step outside to the enormous composite deck overlooking the oversized backyard, babbling brook & corner lot setting, ideal for entertaining or relaxing. The main floor also offers 3 bedrooms, a full bath w/ tiled tub surround, & an eat-in kitchen w/ breakfast bar, tile flooring, large pantry & laundry area. The walkout lower level provides a full in-law setup w/ separate access, featuring 1 bedroom, living room, kitchen, den, full bath & laundry. Additional highlights include energy savings w/ solar, plenty of parking, 2-car garage, generous yard space & a great commuter location w/ access to Worcester, Boston, Providence & Hartford. Don't miss out on the beautiful home where pride of ownership shines throughout in a location thats hard to beat!

Features

4 bedrooms

2 bathrooms

8 carspaces

2 garage spaces

2478 sq. ft. floor area

2.03 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Windham County over the last 12 months, the estimated median property value of 309 Oleary Road is $541k.

Median value

$541k

Estimated value range

$457k - $726k

Median days on market

Estimated value trend

-11%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Windham County. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 309 Oleary Road

2026

Sold

$542,000

17 Aug 2026 by Jared Meehan, of REMAX Bell Park Realty | Killingly

2021

Sold

$370,000

30 Sep 2021 by Jared Meehan, of REMAX Bell Park Realty | Killingly

2015

Sold

$249,000

29 May 2015 by Jared Meehan, of RE/MAX Bell Park Realty

Happy sellers in Windham County

We have insufficient information to provide an overview of customer satisfaction for Windham County. Viewing the agent profiles, reviews and sales for Windham County can provide insights for this location.