86 Chestnut Street
Windham, Connecticut 06226
- Beds
- 4
- Baths
- 2
- SqFt
- 1,560
- Acres
- 0.16
- Year Built
- 1887
- Neighborhood
- Willimantic
- Property Type
- 2 Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
INVESTOR OPPORTUNITY IN WILLIMANTIC! Bring your vision to 86 Chestnut Street, an approximately 1,560 SF multifamily property. Originally built in 1887, the property offers timeless architectural character and charm rarely found in newer construction. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shops, restaurants, services, and major area routes. Offered AS-IS, providing an opportunity to renovate and customize to your investment strategy. The property's character, layout, location, and value-add potential make this an excellent opportunity for an investor or owner-occupant. Cash or conventional financing only. No government financing. Buyer to conduct their own due diligence regarding condition, zoning, intended use, and renovation potential.
Key Facts
- City/Town
- Windham
- Neighborhood
- Willimantic
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1887
- Days on Market
- 1 day
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,560 sq ft
- Lot Size
- 0.16 acres
- Garage / Parking
- 1 garage
- Property Taxes
- $4,775 / Annually
Market Snapshot
The Windham Market
Multi-Family · trailing 12 months
Active Listings
5
Windham inventory
Median List Price
$299,900
5 active listings
Median Closed Price
$312,500
22 sales
Median Days on Market
68
5 active listings
Median $ / Sq Ft
$163
5 active listings
Sale-to-List Ratio
100.0%
22 sales
How this home compares
List Price
$290,000
vs $299,900 median
In line with median
Price / Sq Ft
$186
vs $163 median
14.1% above median
Days on Market
1 day
vs 68 days median
67 days fresher than median
Based on 5 active and 22 closed sales (trailing 12 mo) of multi-family in Windham. Source: SmartMLS · As of August 27, 2026.
Location
86 Chestnut Street, Windham, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per month
- Principal & Interest$1,489
- Property Taxes$398
- Insurance$97
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Windham
- Neighborhood
- Willimantic
- County
- Windham
Residence
- Property Type
- Multi-Family
- Subtype
- Duplex
- Style
- Units on different Floors
- Year Built
- 1887
- New Construction
- No/Resale
- Living Area
- 1,560 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- None
- Basement
- FullUnfinishedSump PumpStorageHatchway AccessInterior Access
Exterior & Lot
- Lot Size
- 0.16 acres
- Zoning
- NPR2
- Garage / Parking
- 1 garage spaceDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Clapboard
- Color
- Green
- Roof
- Asphalt ShingleGable
- Foundation
- Masonry
- Exterior Features
- BalconyPorch
- Lot Description
- Level LotHistoric District
Listing & Financials
- Property Taxes
- $4,775 / Annually
- Days on Market
- 1
- MLS #
- 24201649
- MLS Status
- Active
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 8/27/2026 at 3:10 AM UTC.