309 Oleary Road
Thompson, Connecticut 06277
- Beds
- 4
- Baths
- 2
- SqFt
- 2,478
- Acres
- 2.03
- Year Built
- 1989
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
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!
Key Facts
- City/Town
- Thompson
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch
- Year Built
- 1989
- Days on Market
- 70 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 2,478 sq ft
- Lot Size
- 2.03 acres
- Garage / Parking
- 2 garage · 8 total
- Property Taxes
- $5,730 / 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
$479,900
vs $480,000 median
In line with median
Price / Sq Ft
$194
vs $271 median
28.4% below median
Days on Market
70 days
vs 46 days median
24 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
309 Oleary Road, Thompson, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,447
- Property Taxes$478
- Insurance$160
- 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
- Ranch
- Year Built
- 1989
- New Construction
- No/Resale
- Living Area
- 2,478 sq ft
- Below Grade
- 1,008 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- ElectricOil
- Cooling
- None
- Laundry
- Lower LevelMain Level
- Laundry Location
- Hookups on both 1st floor & lower level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherElectric Dryer
- Basement
- FullHeatedFully FinishedApartmentInterior AccessLiveable SpaceFull With Walk-Out
- In-Law Apartment
- YesLower LevelSeparate Entry
- Interior Features
- Auto Garage Door OpenerOpen Floor Plan
Exterior & Lot
- Lot Size
- 2.03 acres
- Zoning
- RRAD
- Garage / Parking
- 2 garage spaces8 total parking spacesUnder House GarageOff Street ParkingDrivewayGravel
- Waterfront
- Direct waterfront
- Waterfront Details
- Brook
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Vinyl Siding
- Roof
- Shingle
- Foundation
- Concrete
- Exterior Features
- SidewalkShedFruit TreesPorchDeckGuttersStone Wall
- Lot Description
- SecludedCorner LotLightly WoodedLevel LotRollingOpen Lot
Listing & Financials
- Property Taxes
- $5,730 / Annually
- Days on Market
- 70
- MLS #
- 24176516
- MLS Status
- Under Contract
- Financing
- FHA,VA,CHFA
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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 6:15 AM UTC.