105-107 South Chestnut Street
Plainfield, Connecticut 06387
- Beds
- 6
- Baths
- 4
- SqFt
- 2,522
- Acres
- 0.20
- 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
Welcome to this well-maintained side-by-side two-family home, offering an excellent opportunity for both owner-occupants and investors! Each spacious unit features 3 bedrooms and 2 full bathrooms, providing comfortable and functional living spaces with plenty of room to grow. Whether you're looking to live in one unit while generating rental income from the other, or seeking a solid investment property, this versatile two-family offers a great opportunity. Conveniently located near major highways, shopping, dining, schools, and other local amenities, making commuting and everyday living a breeze. Don't miss your chance to own this fantastic income-producing property in a convenient location!
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
- 4 full
- Living Area
- 2,522 sq ft
- Lot Size
- 0.20 acres
- Property Taxes
- $2,809 / Annually
Market Snapshot
The Plainfield Market
Multi-Family · trailing 12 months
Active Listings
4
4 under contract
Median List Price
$369,450
4 active listings
Median Closed Price
$345,000
26 sales
Median Days on Market
19
4 active listings
Median $ / Sq Ft
$168
4 active listings
Sale-to-List Ratio
100.0%
26 sales
How this home compares
List Price
$309,900
vs $369,450 median
16.1% below median
Price / Sq Ft
$123
vs $168 median
26.8% below median
Days on Market
0 days
vs 19 days median
19 days fresher than median
Based on 4 active and 26 closed sales (trailing 12 mo) of multi-family in Plainfield. Source: SmartMLS · As of September 11, 2026.
Location
105-107 South Chestnut Street, Plainfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$1,610
- Property Taxes$234
- Insurance$103
- 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
- 2,522 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Plainfield
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- None
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.20 acres
- Zoning
- RA19
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Shingle
- Foundation
- Concrete
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $2,809 / Annually
- Days on Market
- 0
- MLS #
- 24206012
- MLS Status
- Active
- Financing
- FHA,VA,USDA
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Daniel Deojay
RE/MAX Bell Park Realty
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/11/2026. 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 9/11/2026 at 3:30 PM UTC.