137 & 141 Main Street South
Woodbury, Connecticut 06798
- Beds
- 9
- Baths
- 8
- SqFt
- 4,492
- Acres
- 1.15
- Year Built
- 1800
- Property Type
- 5+ 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
Rare mixed-use investment opportunity on over an acre along Woodbury's desirable Main Street South. This unique property features a seven-unit residential building, a detached garage with an additional apartment above, and a separate commercial building offering approximately 2,000 square feet with its own dedicated entrance and access. Three of the residential units are currently occupied, while the remaining units present an opportunity for renovation and value-add potential. The separate commercial building offers flexibility for a variety of business, office, or retail uses, creating multiple income opportunities on a single property. Properties offering this combination of residential and commercial space in such a prime Woodbury location rarely become available. Whether you're looking to expand your investment portfolio or reimagine a mixed-use property with significant upside, this is an opportunity not to be missed. Property is being sold as-is.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Other
- Year Built
- 1800
- Days on Market
- 0 days
- Beds
- 9
- Baths
- 8 full
- Living Area
- 4,492 sq ft
- Lot Size
- 1.15 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,082 / Annually
Market Snapshot
The Woodbury Market
Multi-Family · trailing 12 months
Active Listings
1
Woodbury inventory
Median List Price
$600,000
1 active listing
Median Closed Price
$370,000
3 sales
Median Days on Market
0
1 active listing
Median $ / Sq Ft
$134
1 active listing
Sale-to-List Ratio
103.3%
3 sales
How this home compares
List Price
$600,000
vs $600,000 median
In line with median
Price / Sq Ft
$134
vs $134 median
In line with median
Days on Market
--
vs 0 days median
Limited comparable data
Based on 1 active and 3 closed sales (trailing 12 mo) of multi-family in Woodbury. Source: SmartMLS · As of August 5, 2026.
Location
137 & 141 Main Street South, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 30, 2026per month
- Principal & Interest$3,085
- Property Taxes$590
- Insurance$200
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Multi-Family
- Subtype
- 5 Family+
- Style
- Other
- Year Built
- 1800
- New Construction
- No/Resale
- Living Area
- 4,492 sq ft
Schools
- Elementary
- Mitchell
- High
- Nonnewaug
Interior
- Heating
- BaseboardHot Air
- Heat Fuel
- ElectricOil
- Cooling
- None
- Laundry
- None
- Basement
- PartialFullFull With Hatchway
Exterior & Lot
- Lot Size
- 1.15 acres
- Zoning
- MSD
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- PorchDeck
- Lot Description
- Lightly WoodedLevel LotSloping Lot
Listing & Financials
- Property Taxes
- $7,082 / Annually
- Days on Market
- 0
- MLS #
- 24195107
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Timothy Drakeley
Drakeley Real Estate, Inc.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/5/2026. 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 8/5/2026 at 8:25 PM UTC.