81 Chestnut St

Windham, CT 06226

$309,000
Price
3
Beds
2,412 Sq. Ft.
$128 / Sq. Ft.
2,412
Sq. Ft.
$128
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Incredible entry with small, covered porch and benches on both sides inside entry door
Sits up on a hill
Detached Garage and small shed great storage
Nice one car garage with small storage area
Has a nice back yard
This is just a stunning Home
Lots of original features here, windows, original mail shoot, nice benches
Beautiful, covered porch to enjoy
Fireplace makes for a nice cozy living room
Large windows let's in lots of natural light
Harwood floors are beautiful in this formal dining room
Original Pantry All original woodwork is stunning
Original deep porcelain sinks and drying rack
Good size eat in area
original porcelain sink
From kitchen looking into hallway
First floor bedroom
First floor bathroom
Stunning stairway
Top of Stairs
Top of stairs both windows open in
Second Floor Family room with entry to sleeping porch
Lots of built ins
Original sleeping porch
Bedroom on second floor
Hallway on second floor with built in
Second floor set up as second kitchen could be bedroom an office or craft room
Second floor set up as kitchen
Second floor full bathroom
electrical Panel
Newer Furnace
First Floor
Second Floor
Attic
Basement Floor plan

Description

Step into timeless elegance with this beautiful Colonial home, nestled in the historic Hill section of town. Built in 1918, this character-filled residence showcases the original charm and craftsmanship that make historic homes so special. From the moment you enter, you'll appreciate the stunning original woodwork, period lighting fixtures, welcoming entryway, and classic fireplace. Large windows throughout the home fill every room with natural light, highlighting the beautiful hardwood floors and...Step into timeless elegance with this beautiful Colonial home, nestled in the historic Hill section of town. Built in 1918, this character-filled residence showcases the original charm and craftsmanship that make historic homes so special. From the moment you enter, you'll appreciate the stunning original woodwork, period lighting fixtures, welcoming entryway, and classic fireplace. Large windows throughout the home fill every room with natural light, highlighting the beautiful hardwood floors and architectural details. The main level features a spacious living room, formal dining room, kitchen, full bathroom, and a convenient first-floor bedroom. Upstairs, you'll find two to three additional bedrooms, a second full bathroom, and a large family room offering flexible living space for today's lifestyle. Enjoy relaxing on the covered front porch or take advantage of the home's original sleeping porch, a unique feature that adds to its historic appeal. Many of the home's mechanical systems have been updated, providing peace of mind while preserving its vintage character. Ideally located within walking distance to downtown, you'll have easy access to local restaurants, galleries, shops, and community events. This is a rare opportunity to own a home filled with charm, character, and history.
  1. Listed by Jeanne L Crum • Home Selling Team
    P: (860)-942-4970 C: (860)-942-4970 jeanne@homesellingteam.com

Property Details for 81 Chestnut Street

Basement Description
Full, Unfinished, Storage, Interior Access, Concrete Floor, Full With Hatchway
Direct Waterfront
No
Garages Number
1
Neighborhood
Willimantic
Style
Colonial
Garage Parking Info
Detached Garage, Off Street Parking
Swimming Pool
No
LISTING UPDATED: 06/12/2026 03:45 PM

Property Details for 81 Chestnut Street

StatusActive
MLS #24180787
Days on Market4
Taxes$8,020 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1918
Lot Size0.36 AC / 15,681 SF
CountyWindham County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Home Selling Team, Jeanne L Crum
Add your commute

Building Information for 81 Chestnut Street

Stories-Year Built1918Building Size-Lot Size0.36 AC / 15,681 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$2,208 per month

30 year fixed, 6.36% Interest

Principal and Interest

$1,540

Property Taxes

$668

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 81 Chestnut Street

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Prospect St to Chestnut Street
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • Latitude: 41.717128
  • Longitude: -72.21243
  • Middle Jr High School: Per Board of Ed
  • Neighborhood Amenities: Commuter Bus, Health Club, Library, Medical Facilities, Park, Public Transportation, Shopping/Mall, Walk to Bus Lines
  • State: Connecticut
Parking
  • Parking Total Spaces: 2
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $8,020
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch-Screened, Porch-Enclosed, Sidewalk, Shed, Porch, Garden Area, Stone Wall
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Washer
  • Attic Description: Unfinished, Storage Space, Walk-up
  • Cooling System: None
  • Heat Type: Steam
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Cable - Available
  • Laundry Room Info: Main Level
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 23.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 13.0
Room 2
  • Room Entry Order: 2
  • Room Features: French Doors,Hardwood Floor
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 13.0
Room 3
  • Room Entry Order: 3
  • Room Features: Built-In Hutch,Eating Space,Laundry Hookup
  • Room Length: 22.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 22.0
Room 4
  • Room Entry Order: 4
  • Room Features: Hardwood Floor
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 10.0
Room 5
  • Listing Key: 535BAA4C6395E1E8E0631A01100A46AE
  • Room Entry Order: 5
  • Room Features: Hardwood Floor
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 6
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 13.0
Room 7
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Office
  • Room Width: 10.0
Room 8
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Family Room
  • Room Width: 14.0
Property
Property and Assessments
  • Color: Brown and Brick
  • Construction Description: Frame, Brick
  • Exterior Siding: Shingle, Brick
  • Foundation Type: Stone
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1918
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Second Floor
  • In Law Apartment: Possible
  • Living Area SQFT Per Public Records: 2412
Lot Information
  • Lot Description: Historic District
  • Parcel Number: 2291324
  • Sq Ft Est Heated Above Grade: 2412.0
  • Sq Ft Total: 2412.0
  • Zoning: NPR2
Utilities
  • Energy Features: Storm Doors
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Electric, Domestic
  • 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: Owner

Public Records for 81 Chestnut Street

Taxable ValueLand$31,220Additions$185,410Total$216,630
Tax Record2024$8,020 ($668 / month)
Home Facts
Beds3Baths2Total Finished SqFt2,412 SqFtAbove Grade Finished SqFt2,412 SqFtUnfinished Basement SqFt1,206 SqFtStories2Lot Size15,682 SqFtStyleSingle Family ResidenceYear Built1918ZoningNPR2CountySOUTHEASTERN CONNECTICUTAPNWNDH M:13-03 B:049 L:19Fireplace TypeHas Fireplace

Schools near 81 Chestnut Street

This home is within Windham School District.
Rating
School
Type
Grades
Distance
W. B. Sweeney 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
W. B. Sweeney 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.

Similar Homes

Explore Nearby Homes

More information about 81 Chestnut Street, Windham, CT 06226

81 Chestnut Street is a single family home for sale in Windham, CT 06226. This property was listed for sale on June 12, 2026 by Home Selling Team, it's currently listed at $309,000. This listing's school district is Windham School District. Nearby schools include W. B. Sweeney School, Windham Middle School and Windham High School. 81 Chestnut Street is a 3-bed, 2-bath, 2,412 sqft single family home built in 1918.

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 Home Selling Team, Jeanne L Crum

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.