137-139 South Chestnut Street
Plainfield, Connecticut 06387
Reduced from $380,000
- Beds
- 8
- Baths
- 2
- SqFt
- 2,522
- Acres
- 0.20
- Year Built
- 1860
- Neighborhood
- Wauregan
- Property Type
- 2 Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Excellent opportunity to own a spacious two-family home offering flexibility for owner-occupants or investors. Each unit features 4 bedrooms and 1 full bath. Both units have their own utilities. Outdoors, each unit enjoys its own backyard area separated by fencing, creating defined outdoor spaces for each residence. A detached 2-car garage provides additional parking and storage, adding even more value. Whether you're looking to live in one unit while generating rental income from the other or add a multi-unit property to your investment portfolio, this two-family home is well worth a look!
Key Facts
- City/Town
- Plainfield
- Neighborhood
- Wauregan
- Property / Style
- Multi-Family · Units are Side-by-Side
- Year Built
- 1860
- Days on Market
- 49 days
- Beds
- 8
- Baths
- 2 full
- Living Area
- 2,522 sq ft
- Lot Size
- 0.20 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $3,306 / Annually
Market Snapshot
The Plainfield Market
Multi-Family · trailing 12 months
Active Listings
4
3 under contract
Median List Price
$389,950
4 active listings
Median Closed Price
$350,000
26 sales
Median Days on Market
33
4 active listings
Median $ / Sq Ft
$174
4 active listings
Sale-to-List Ratio
100.7%
26 sales
How this home compares
List Price
$365,000
vs $389,950 median
6.4% below median
Price / Sq Ft
$145
vs $174 median
16.7% below median
Days on Market
49 days
vs 33 days median
16 days longer than median
Based on 4 active and 26 closed sales (trailing 12 mo) of multi-family in Plainfield. Source: SmartMLS · As of November 9, 2026.
Location
137-139 South Chestnut Street, Plainfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$1,978
- Property Taxes$276
- Insurance$122
- 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
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Laundry
- All Units Have Hook-UpsBasement Hook-Up(s)
- Laundry Location
- Unit 139 main floorunit 137 in basemen
- Basement
- FullConcrete Floor
Exterior & Lot
- Lot Size
- 0.20 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
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $3,306 / Annually
- Days on Market
- 49
- MLS #
- 24208553
- MLS Status
- Active
- Financing
- FHA,CHFA
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 11/9/2026. 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 11/9/2026 at 8:50 AM UTC.