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!
Est. $2,649 per month, based on comparable rentals
Sale and tax history for 309 Oleary Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24176516
Aug 18, 2026
Listing Removed
—
Aug 17, 2026
Sold
$542,000
$219/sq ft
Jun 3, 2026
Pending
—
May 26, 2026
Listed
$479,900
$194/sq ft
May 18, 2026
Coming Soon
$479,900
$194/sq ft
Smart MLS #170428336
Sep 30, 2021
Sold
$370,000
$149/sq ft
Aug 11, 2021
Listed
$349,900
$141/sq ft
Spectacular Thompson location on a corner lot just. a few minutes from the RI and MA border!! Turn key condition this home features an open layout, an in-law apartment that is nearly 1000 SF with a separate entrance, and walkout to the exterior! The first floor has everything that you need. As you walk in you are greeted with a stunning great room with vaulted ceilings, TONS of light and access to the rear heated 4 season sun porch! To the right is a formal dining room/eating area, a spacious kitchen with an enormous amount of counter space and cabinets!! Access out to your HUGE composite deck through the kitchen makes this perfect for grilling and summer time entertaining!! The laundry doubles as a walk-in pantry as well! Rounding out the main floor you have 3 bedrooms, and a spare bathroom! The lower level has an in-law with tons of versatility; access not only to the home but a walkout too! One bedroom, living room, dining area of office and full kitchen and bath! Save some money with the solar panels (leased) on the roof! The yard and grounds need to be seen, along with the trickling stream on the property!! Composite deck, loads of updates, and ready of a new owner!!
Smart MLS #E10032771
May 29, 2015
Sold
$249,000
$100/sq ft
Apr 6, 2015
Listed
$247,900
$100/sq ft
Enjoy the tranquil sounds of a trickling brook flowing down your property from your oversized deck on a gorgeous corner lot and incredible yard! This is a rare find with this sprawling ranch with full in-law, separate access, and walkout basement! The great room is a welcomed addition to the home with a gorgeous heated sunroom off of it that leads to the oversized deck. Eat in kitchen with loads of counter space, eat in island, and beautiful dining room!! Open layout is great for entertaining all with one floor living! If that wasn't enough, there is a laundry room/pantry! The Lower level is a completely finished in-law with separate access, laundry, and in pristine condition! Nice living area, eat in kitchen, and den! Country setting on this corner lot, is just a few miles from 395, easy commute to Worcester, RI, or even Boston! This home offers it all, ready for a new owner! Tons of updates, and extremely well kept!
Year
Property tax
Land + Additions
Assessment*
2023
$4,519 (+3.9%)
$46,700 + $127,100
$173,800
2022
$4,348 (+0.3%)
$46,700 + $127,100
$173,800
2021
$4,336 (+3.0%)
$46,700 + $127,100
$173,800
2020
$4,211 (+0.9%)
$46,700 + $127,100
$173,800
2019
$4,174
$49,000 + $101,400
$150,400
2018
$4,174 (+6.5%)
$49,000 + $101,400
$150,400
2017
$3,919
$49,000 + $101,400
$150,400
2016
$3,919 (+9.1%)
$49,000 + $101,400
$150,400
2014
$3,593 (+3.0%)
$51,500 + $105,600
$157,100
2011
$3,488
$51,500 + $105,600
$157,100
Public record
Beds
4
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
2.03 Acres
Year renovated
—
Sq. Ft.
1,470
Year built
1989
Style
Single Family Residential
County
Windham County
APN
1722711
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 13, 2023.
Property details
Parking
Garage Information
Garage & Parking: Under House Garage, Off Street Parking, Driveway
Garages Number: 2
Parking Information
Parking Total Spaces: 8
Interior
Virtual Tour Information
Interior Information
Total Rooms: 10
Laundry Room Location: Hookups on both 1st floor & lower level
Laundry Room Info: Lower Level, Main Level
Interior Features: Auto Garage Door Opener, Open Floor Plan
In-Law Apartment: Yes
In-Law Access: Lower Level, Separate Entry
Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Electric Dryer
Bathroom Information
# of Baths (Full): 2
Bedroom Information
Beds Total: 4
Room Information
Basement Description: Full, Heated, Fully Finished, Apartment, Interior Access, Liveable Space, Full With Walk-Out
Has Attic
Attic Description: Access Via Hatch
Exterior
Exterior Features
Roof Information: Shingle
Exterior Siding: Vinyl Siding
Exterior Features: Sidewalk, Shed, Fruit Trees, Porch, Deck, Gutters, Stone Wall
Lot Information
Lot Description: Secluded, Corner Lot, Lightly Wooded, Level Lot, Rolling, Open Lot
Building Information
Foundation Type: Concrete
Construction Description: Frame
Property Information
Waterfront Description: Brook
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 1470
Driveway Type: Gravel
Financial
Assessments Information
Assessed Value: $301,600
Utilities
Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Tankless Hotwater
Heat Type: Baseboard
Heat Fuel Type: Electric, Oil
Fuel Tank Location: Above Ground
Energy Features: Active Solar, Programmable Thermostat
Location
School Information
High School: Per Board of Ed
Elementary School: Per Board of Ed
Location Information
State: Connecticut
Directions: GPS Friendly
Direct Waterfront
County: Windham
Public facts
Beds: 4
Baths: 2.0
Sq. Ft.: 1,470
Stories: 1.0
Lot Size: 2.03 acres
Style: Single Family Residential
Year Built: 1989
Year Renovated: —
County: Windham County
APN: 1722711
Home facts updated by county records on Jul 13, 2023
Other
Documents & Disclosures
Supplement Count Public: 2
Around this home
Schools
Mary R. Fisher Elementary School
Public PreK-4 • Assigned • 3.7mi
5/10
Thompson Middle School
Public 5-8 • Assigned • 3.7mi
6/10
Tourtellotte Memorial High School
Public 9-12 • Assigned • 3.7mi
5/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
3/10 Fire Factor
0.31% chance of being in a wildfire in next 30 years
3/10 Heat Factor
7 days above 95° expected this year, 15 days in 30 years
6/10 Wind Factor
52% chance of strong winds in next 30 years
2/10 Air Factor
2 unhealthy days expected this year, 2 days in 30 years
Provided by First Street
Historical weather
Thompson, CT • 06277
Average low and high temperatures (°F)
32
17
35
18
50
30
61
39
68
48
80
58
82
64
79
58
73
53
63
42
50
34
37
22
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
87/ 100
Very good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.2 hrs
5.7 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$477,000 – $577,000
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