17-19 North Chestnut Street
Plainfield, Connecticut 06387
- Beds
- 6
- Baths
- 2
- SqFt
- 2,279
- Acres
- 0.18
- Year Built
- 1860
- Neighborhood
- Wauregan
- 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
A fantastic opportunity for investors or owner-occupants! This well-maintained two-family property offers three bedrooms on each side, full basements, city water and sewer, and a detached oversized 2car garage with workshop. The property has been lovingly maintained and improved over the past 20 years with numerous updates throughout. Improvements include double paned windows, newer heating systems, electrical system updates, and chimney improvements with new crowns. Fresh interior painting and ongoing updates reflect the care and attention this property has received. Both units offer spacious living while the full basements provide additional storage and utilities. One unit is currently occupied by a tenant on a month-to-month lease, offering flexibility for the next owner. With its excellent condition, substantial improvements and desirable two-family layout this property is a wonderful opportunity for investors seeking rental income or buyers looking to live in one unit while generating income from the other. DONT MISS THIS ONE!
Key Facts
- City/Town
- Plainfield
- Neighborhood
- Wauregan
- Property / Style
- Multi-Family · Units are Side-by-Side
- Year Built
- 1860
- Days on Market
- 0 days
- Beds
- 6
- Baths
- 2 full
- Living Area
- 2,279 sq ft
- Lot Size
- 0.18 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $3,218 / Annually
Market Snapshot
The Plainfield Market
Multi-Family · trailing 12 months
Active Listings
4
5 under contract
Median List Price
$384,950
4 active listings
Median Closed Price
$345,000
26 sales
Median Days on Market
33
4 active listings
Median $ / Sq Ft
$152
4 active listings
Sale-to-List Ratio
100.0%
26 sales
How this home compares
List Price
$349,900
vs $384,950 median
9.1% below median
Price / Sq Ft
$154
vs $152 median
In line with median
Days on Market
0 days
vs 33 days median
33 days fresher than median
Based on 4 active and 26 closed sales (trailing 12 mo) of multi-family in Plainfield. Source: SmartMLS · As of October 1, 2026.
Location
17-19 North Chestnut Street, Plainfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$1,868
- Property Taxes$268
- Insurance$117
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Plainfield
- Neighborhood
- Wauregan
- County
- Windham
Residence
- Property Type
- Multi-Family
- Subtype
- Duplex
- Style
- Units are Side-by-Side
- Year Built
- 1860
- New Construction
- No/Resale
- Living Area
- 2,279 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- BaseboardHot Water
- Heat Fuel
- Natural Gas
- Cooling
- None
- Basement
- FullInterior AccessConcrete Floor
Exterior & Lot
- Lot Size
- 0.18 acres
- Zoning
- RA19
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $3,218 / Annually
- Days on Market
- 0
- MLS #
- 24205261
- MLS Status
- Active
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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 10/1/2026. 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 10/1/2026 at 9:00 PM UTC.