309 O'Leary Rd

Thompson, CT 06277

$479,900
Price
4
Beds
2,478 Sq. Ft.
$194 / Sq. Ft.
2,478
Sq. Ft.
$194
per Sq. Ft.
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Under Contract
Under Contract
a view of a garden with a fountain
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a large kitchen with stainless steel appliances granite countertop a refrigerator a sink and a stove
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Description

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...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!
  1. Listed by Jared Meehan • RE/MAX Bell Park Realty
    P: (508)-561-0249 C: (508)-561-0249 jaredmeehan@remax.net

Property Details for 309 O'Leary Road

Basement Description
Full, Heated, Fully Finished, Apartment, Interior Access, Liveable Space, Full With Walk-Out
Direct Waterfront
Yes
Expected Active Date
05-26-2026
Garages Number
2
Neighborhood
N/A
Style
Ranch
Garage Parking Info
Under House Garage, Off Street Parking, Driveway
Swimming Pool
No
LISTING UPDATED: 06/03/2026 11:57 PM

Property Details for 309 O'Leary Road

StatusUnder Contract
MLS #24176516
Days on Market7
Taxes$5,730 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1989
Lot Size2.03 AC / 88,426 SF
CountyWindham County
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Location

Listing Courtesy of RE/MAX Bell Park Realty, Jared Meehan
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Building Information for 309 O'Leary Road

Stories-Year Built1989Building Size-Lot Size2.03 AC / 88,426 SF

Payment Calculator

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$2,869 per month

30 year fixed, 6.36% Interest

Principal and Interest

$2,391

Property Taxes

$478

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 309 O'Leary Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS Friendly
  • Elementary School: Per Board of Ed
  • Flood Zone: No
  • High School: Per Board of Ed
  • Latitude: 41.947913
  • Longitude: -71.836576
  • State: Connecticut
Parking
  • Parking Total Spaces: 8
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $5,730
Interior and Exterior Features
Exterior Features
  • Exterior Features: Sidewalk, Shed, Fruit Trees, Porch, Deck, Gutters, Stone Wall
  • Waterfront Description: Brook
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Electric Dryer
  • Attic Description: Unfinished, Access Via Hatch
  • Cooling System: None
  • Heat Type: Baseboard
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Interior Features: Auto Garage Door Opener, Open Floor Plan
  • Laundry Room Info: Lower Level, Main Level
  • Laundry Room Location: Hookups on both 1st floor & lower level
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: Vaulted Ceiling,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 10
  • Room Features: Wall/Wall Carpet
  • Room Level: Lower
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 11
  • Room Features: Wall/Wall Carpet
  • Room Level: Lower
  • Room Type: Family Room
Room 4
  • Room Entry Order: 12
  • Room Features: Tile Floor
  • Room Level: Lower
  • Room Type: Den
Room 5
  • Listing Key: 521CBFBDA0E22E66E0631A01100A2018
  • Room Entry Order: 2
  • Room Features: Tile Floor
  • Room Level: Main
  • Room Type: Sun Room
Room 6
  • Room Entry Order: 3
  • Room Features: Breakfast Bar,Tile Floor
  • Room Level: Main
  • Room Type: Kitchen
Room 7
  • Room Entry Order: 4
  • Room Features: Tile Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 8
  • Room Entry Order: 5
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 9
  • Listing Key: 521CBFBDA0E22E66E0631A01100A2018
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 10
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 11
  • Room Entry Order: 8
  • Room Level: Main
  • Room Type: Full Bath
Room 12
  • Room Entry Order: 9
  • Room Features: Tile Floor
  • Room Level: Lower
  • Room Type: Kitchen
Property
Property and Assessments
  • Construction Description: Frame
  • Driveway Type: Gravel
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: Above Ground
  • New Construction Type: No/Resale
  • Roof: Shingle
  • Year Built: 1989
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Lower Level, Separate Entry
  • In Law Apartment: Yes
  • Sq Ft Est Heated Below Grade: 1008
  • Living Area SQFT Per Public Records: 1470
Lot Information
  • Lot Description: Secluded, Corner Lot, Lightly Wooded, Level Lot, Rolling, Open Lot
  • Parcel Number: 1722711
  • Sq Ft Est Heated Above Grade: 1470.0
  • Sq Ft Total: 2478.0
  • Zoning: RRAD
Utilities
  • Energy Features: Active Solar, Programmable Thermostat
  • Heat Fuel Type: Electric, Oil
  • Hot Water Description: Tankless Hotwater
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 309 O'Leary Road

DateEvent & SourcePriceAppreciation
May 29, 2015

Closed (Public Record)

Public Record #550463914

$249,000—
DateEvent & SourcePrice
05/29/2015

Closed (Public Record)

Public Record #550463914

$249,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 309 O'Leary Road

Taxable ValueLand$65,900Additions$235,700Total$301,600
Tax Record2024$5,730 ($478 / month)
Home Facts
Beds4Baths2Total Finished SqFt1,470 SqFtAbove Grade Finished SqFt1,470 SqFtStories1Lot Size88,427 SqFtStyleSingle Family ResidenceYear Built1989ZoningRRADCountyNORTHEASTERN CONNECTICUTAPNTPSN M:126 B:16 L:18-A

Schools near 309 O'Leary Road

This home is within Thompson School District.
Rating
School
Type
Grades
Distance
Mary R. Fisher Elementary School
Public - PK to 4
Thompson Middle School
Public - 5 to 8
Tourtellotte Memorial High School
Public - 9 to 12
Rating
School
Distance
Mary R. Fisher Elementary School
PublicPK to 4

Thompson Middle School
Public5 to 8

Tourtellotte Memorial High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of RE/MAX Bell Park Realty, Jared Meehan

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.