22-24 Woodland Street
Simsbury, Connecticut 06070
- Beds
- 5
- Baths
- 3
- SqFt
- 1,811
- Acres
- 0.34
- Year Built
- 1920
- Property Type
- 2 Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
1
Simsbury inventory
Median List Price
$585,000
1 active listing
Median Closed Price
$433,520
2 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per 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.
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.