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137 & 141 Main Street South

Woodbury, Connecticut 06798

ACTIVE - NEW$600,000
Beds
9
Baths
8
SqFt
4,492
Acres
1.15
Year Built
1800
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage

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

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

Property

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,875

per 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.

Listed By

Taylor O'Keefe-Hamel

(203) 578-5388

Drakeley Real Estate, Inc.

(203) 263-4336

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.