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22-24 Woodland Street

Simsbury, Connecticut 06070

ACTIVE - NEW$585,000
Beds
5
Baths
3
SqFt
1,811
Acres
0.34
Year Built
1920
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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About This Home

A rare opportunity to own a distinctive two-family home combining Simsbury history, comfortable living, income potential, and an exceptional natural setting along Stratton Brook. Tucked away at the end of a quiet residential street yet remarkably convenient to the heart of Simsbury, 22-24 Woodland Street offers the privacy of a neighborhood setting with easy access to the shops, restaurants, library, recreation, trails, and the amenities of Simsbury Center. An original Ensign-Bickford home, the property is part of an important chapter in Simsbury's history. Ensign-Bickford constructed housing in this area for its employees as the company and surrounding community grew, and Woodland Street remains a tangible connection to the town's industrial heritage. Today, the property offers something equally compelling: two comfortable and distinct residences under one roof. Unit 22 features 3 bedrooms and 2 full baths, while Unit 24 offers 2 bedrooms and 1 full bath, providing a total of 5 bedrooms and 3 full baths. The units offer comfortable living spaces and kitchens with appliances, allowing each residence to function as a complete and independent home. Basement space provides additional utility and storage, including laundry facilities for each unit, while tankless hot-water systems enhance the property's functionality, and gas heat and hot water keep the utilities affordable. The versatility is outstanding.

Key Facts

City/Town
Simsbury
Neighborhood
N/A
Property / Style
Multi-Family · Units are Side-by-Side
Year Built
1920
Days on Market
0 days
Beds
5
Baths
3 full
Living Area
1,811 sq ft
Lot Size
0.34 acres
Garage / Parking
2 total
Property Taxes
$6,454 / Annually

Market Snapshot

The Simsbury Market

Multi-Family · trailing 12 months

Median Days on Market

0

1 active listing

Median $ / Sq Ft

$323

1 active listing

Sale-to-List Ratio

97.1%

2 sales

How this home compares

List Price

$585,000

vs $585,000 median

In line with median

Price / Sq Ft

$323

vs $323 median

In line with median

Days on Market

--

vs 0 days median

Limited comparable data

Based on 1 active and 2 closed sales (trailing 12 mo) of multi-family in Simsbury. Source: SmartMLS · As of August 25, 2026.

Location

22-24 Woodland Street, Simsbury, Connecticut

Property

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,737

per month

  • Principal & Interest$3,004
  • Property Taxes$538
  • Insurance$195
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Simsbury
Neighborhood
N/A
County
Hartford

Residence

Property Type
Multi-Family
Subtype
Duplex
Style
Units are Side-by-Side
Year Built
1920
New Construction
No/Resale
Living Area
1,811 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Simsbury

Interior

Heating
Gas on Gas
Cooling
Ceiling FansWindow Unit
Laundry
Common Laundry Area
Laundry Location
In Basement
Basement
FullFull With Hatchway

Exterior & Lot

Lot Size
0.34 acres
Zoning
I-2
Garage / Parking
2 total parking spacesOn Street ParkingOff Street Parking
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Flood Zone
No
Construction
Vinyl Siding
Color
Biege
Roof
Shingle
Foundation
Stone
Exterior Features
PorchGutters
Lot Description
Lightly WoodedLevel LotOn Cul-De-Sac

Listing & Financials

Property Taxes
$6,454 / Annually
Days on Market
0
MLS #
24198047
MLS Status
Active
Financing
FHA,VA

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Mike Daly

(860) 729-7433

Berkshire Hathaway NE Prop.

(860) 633-3674

Co-Listed By

Chester Malley

Berkshire Hathaway NE Prop.

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/25/2026. 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 8/25/2026 at 10:55 PM UTC.