#24062280, Anthony Chabot, Listing Office: Chabot & Associates Real Estate

269 Jackson St Windham, CT 06226
Property details
About 269 Jackson St
Welcome to a rare opportunity for both savvy investors and future owner-occupants alike. This Colonial-style three-family home offers the ideal blend of character, functionality, and strong income potential. Whether you're looking to offset your mortgage with tenant income or expand your investment portfolio, this property is a smart choice. The owner's unit will be delivered vacant and features an oversized one-bedroom layout with an open-concept eat-in kitchen and dining area, a remodeled bathroom, a spacious living room with a wall of windows, and a bonus room perfect for a home office or den. Direct access to basement storage and abundant natural light complete the space. The second unit is a duplex-style one-bedroom, one-bath with an open kitchen/living room and a classic rocking chair porch, while the third unit features an oversized bedroom, an eat-in kitchen with sliding glass doors to a private deck, and access to a walk-up attic offering incredible storage. Each unit has its own electric meter, with tenants responsible for their own heat and hot water. Recent upgrades, including brand-new hot water heaters and updated electric panels, provide peace of mind. Set on nearly half an acre of land with parking for 8+ cars, the property also offers exciting potential for future expansion on the back portion of the lot, where a barn and four-car building once stood. A rare opportunity and a sound investment.
Highlights
Summary
- Full Bathrooms: 3
- Basement: Yes
- Total Bedroom Count: 3
- Attached Garage: No
- Private Pool: No
- Parking: None, Off Street Parking, Unpaved
- Exterior: Porch, Deck
- Architectural Style: Other
- Heating: Baseboard
- Cooling: None
- List Price: $290,000
- Price/SqFt: $121
- Lot: Level
- Directions: Main Street to Jackson Street to #269.
- Year Built: 1910
- Living Area: 2,382 SqFt
- Lot Size: 0.48 Acres
- MLS Number: 24086628
- Office Name: Giner Real Estate
- Office Phone: (914) 263-0345
- Office Email: Michael@TheTaralloTeam.com
- Listing Agent: Michael Tarallo
Copyright © 2025 Smart MLS. The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 5/2/2025, 4:20:52 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Get an agent. Get a mortgage. Save big.¹

$290,000
269 Jackson St
$3,444
closing credit¹
Sell your home with Rocket and save even more!
Seller rebate
0.5% sale price²
Price information
Property sales
We're sorry, we currently don't have property sales data for this listing.
Tax history
We're sorry, we currently don't have tax history data for this listing.
Nearby schools
3
Natchaug School
Public District KG-5
0.3 mi
•123 Jackson St
3
W. B. Sweeney School
Public District KG-5
1.4 mi
•60 Oak Hill Dr
2
Windham Center School
Public District KG-5
2.5 mi
•45 North Rd
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $35,242. Residents of Windham, CT typically earn less than $<35k each year. Residents typically live in single, no kids family. The most common level of education of people living in this area is high school diploma.
Similar homes for sale
This home is located at 269 Jackson St in Windham, CT and zip code 06226. This 2,382 square foot home, which was built in 1910, sits on a 0.48 acre lot. Features: 3 bedrooms, 3 bathrooms. It has been listed on Rocket Homes since April 27, 2025 and is currently priced at $290,000.
Windham, CT housing market in April 2025 saw over 2 listings sold above listed price, more than 2 sold at listed price and over 3 sold below. The number of listings in Windham, CT decreased by 8.9% between March and April 2025.