269 Jackson St

Windham, CT 06226

$290,000
Last Sold Price
3
Beds
2,382 Sq. Ft.
$122 / Sq. Ft.
2,382
Sq. Ft.
$122
per Sq. Ft.
Closed 10/1/25
Closed 10/1/25
Front of Home

Description

Back on the market - prior buyer unable to perform. Recently appraised above the current list price, this Colonial-style three-family home is now an even better value, with two units to be delivered vacant at closing. A rare opportunity for savvy investors, future owner-occupants, or those seeking space for extended family, it offers a flexibility that wasn't available before - the ability to occupy two units from day one. With its blend of character, functionality, and strong income potential, this...Back on the market - prior buyer unable to perform. Recently appraised above the current list price, this Colonial-style three-family home is now an even better value, with two units to be delivered vacant at closing. A rare opportunity for savvy investors, future owner-occupants, or those seeking space for extended family, it offers a flexibility that wasn't available before - the ability to occupy two units from day one. With its blend of character, functionality, and strong income potential, this property checks all the boxes. The owner's unit, to be delivered vacant, is an oversized one-bedroom 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. It enjoys direct access to basement storage and abundant natural light. The next unit, also to be delivered vacant, features an oversized bedroom, an eat-in kitchen with sliding glass doors to a private deck, and access to a walk-up attic offering exceptional storage. The last unit is occupied by a long-term tenant with a solid rental history and is a duplex-style one-bedroom/one-bath with an open kitchen/living area and a classic rocking chair porch. Each unit has its own electric meter, with tenants responsible for their own heat and hot water. Recent upgrades include brand-new hot water heaters and updated electric panels. Set on nearly half an acre with parking for 8+ cars, the property also offers pot
  1. Listed by Michael A Tarallo • Giner Real Estate
    P: (917)-374-0026 C: (917)-374-0026 Michael@TheTaralloTeam.com

Property Details for 269 Jackson Street

Basement Description
Full, Unfinished, Full With Walk-Out
Direct Waterfront
No
Neighborhood
Willimantic
Style
Other
Garage Parking Info
None, Off Street Parking, Unpaved
Swimming Pool
No
LISTING UPDATED: 10/02/2025 07:51 PM

Property Details for 269 Jackson Street

StatusClosed
MLS #24119791
Days on Market12
Taxes$5,805 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeMulti-Family / 3 Family
Year Built1910
Lot Size0.48 AC / 20,908 SF
CountyWindham County

Location

Listing Courtesy of Giner Real Estate, Michael A Tarallo

Sold By KW Legacy Partners, Julienne Jaber

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Building Information for 269 Jackson Street

Stories-Residences3Year Built1910Building Size-Lot Size0.48 AC / 20,908 SF

Payment Calculator

$1,897 per month

30 year fixed, 6.15% Interest

Principal and Interest

$1,413

Property Taxes

$484

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 269 Jackson Street

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Main Street to Jackson Street to #269.
  • Elementary School: Natchaug
  • Flood Zone: No
  • High School: Windham
  • Latitude: 41.71704
  • Longitude: -72.20404
  • Middle Jr High School: Windham
  • State: Connecticut
Parking
  • Parking Total Spaces: 8
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $5,805
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch, Deck
  • Waterfront Description: Not Applicable
Interior Features
  • Attic Description: Unfinished, Walk-up
  • Cooling System: None
  • Heat Type: Baseboard
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Laundry Room Info: None
  • Rooms Total: 13
Property
Property and Assessments
  • Color: Brown
  • Construction Description: Frame
  • Exclusions: Property is being sold as-is with two units being delivered vacant.
  • Exterior Siding: Clapboard
  • Foundation Type: Stone
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1910
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 2382
Lot Information
  • Lot Description: Level Lot
  • Parcel Number: 1733657
  • Sq Ft Est Heated Above Grade: 2382.0
  • Sq Ft Total: 2382.0
  • Zoning: NPR2
Utilities
  • Heat Fuel Type: Electric
  • Hot Water Description: Electric, Upright Tank
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Tenant
  • Total Number of Units: 3
  • Total Rooms Multi Family: 13
Unit 1
  • Unit Entry Order: 2
  • Unit Full Baths: 1
  • Unit Modified Date: 08-18-2025
  • Unit Num Bedrms: 1
  • Unit Num Rooms: 4
  • Unit Occupied By: Vacant
Unit 2
  • Lease: Leased
  • Lease Expires: 03-31-2026
  • Unit Entry Order: 3
  • Unit Full Baths: 1
  • Unit Modified Date: 08-18-2025
  • Unit Monthly Rent: $875
  • Unit Num Bedrms: 1
  • Unit Num Rooms: 4
  • Unit Occupied By: Tenant
Unit 3
  • Unit Entry Order: 1
  • Unit Full Baths: 1
  • Unit Modified Date: 08-18-2025
  • Unit Num Bedrms: 1
  • Unit Num Rooms: 5
  • Unit Occupied By: Vacant

Property History for 269 Jackson Street

DateEvent & SourcePriceAppreciation
Apr 5, 2019

Closed (Public Record)

Public Record #643004389

$157,000—
DateEvent & SourcePrice
04/05/2019

Closed (Public Record)

Public Record #643004389

$157,000

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

Public Records for 269 Jackson Street

Taxable ValueLand$26,190Additions$130,620Total$156,810
Tax Record2024$5,805 ($484 / month)
Home Facts
Baths3Total Finished SqFt2,382 SqFtAbove Grade Finished SqFt2,382 SqFtUnfinished Basement SqFt1,060 SqFtStories2Lot Size20,909 SqFtStyleTriplexYear Built1910ZoningNPR2CountyWINDHAMAPNWNDH M:14-03 B:108 L:36

Schools near 269 Jackson Street

This home is within Windham School District.
Rating
School
Type
Grades
Distance
Natchaug School
Public - K to 5
Windham Middle School
Public - 6 to 8
Windham High School
Public - 9 to 12
Eastern Regional Academy/Windham
Public - 5 to 12
Rating
School
Distance
Natchaug School
PublicK to 5

Windham Middle School
Public6 to 8

Windham High School
Public9 to 12

Eastern Regional Academy/Windham
Public5 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 descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Giner Real Estate, Michael A Tarallo

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.