38 Main Street
Simsbury, Connecticut 06081
- Beds
- 0
- Baths
- 2
- SqFt
- 1,392
- Acres
- 0.08
- Year Built
- 1900
- Neighborhood
- Tariffville
- Property Type
- Single 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
Steeped in history and overlooking the picturesque Tariffville Green for more than a century, this charming antique Colonial offers a rare combination of character and exceptional versatility. Due to the property's unique zoning, the possibilities are endless-create a charming single-family home, convert it to a two-family residence by adding a kitchen to the main level, enjoy multi-generational living with an in-law suite, or take advantage of the property's commercial potential. The upper level is currently configured as a comfortable apartment featuring a spacious eat-in kitchen, two bedrooms, a full bath with tub and shower, and a partially finished walk-up attic offering additional space or future expansion possibilities. The main level offers three large, sun-filled rooms and a full bath with a step-in shower, providing flexible space for living, working, or a business opportunity. The basement includes laundry and ample storage, while outside you'll appreciate off-street parking for 5-6 vehicles-a valuable amenity in this desirable village setting. Just steps from the heart of Tariffville, you'll enjoy easy access to local restaurants, shops, parks, and community events. Whether you're searching for a distinctive home, an income-producing property, or a live/work opportunity, this one-of-a-kind property is ready for its next chapter.
Key Facts
- City/Town
- Simsbury
- Neighborhood
- Tariffville
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1900
- Days on Market
- 8 days
- Beds
- 0
- Baths
- 2 full
- Living Area
- 1,392 sq ft
- Lot Size
- 0.08 acres
- Garage / Parking
- 5 total
- Property Taxes
- $4,338 / Annually
Market Snapshot
The Simsbury Market
Single Family · trailing 12 months
Active Listings
17
56 under contract
Median List Price
$710,000
17 active listings
Median Closed Price
$575,000
249 sales
Median Days on Market
31
17 active listings
Median $ / Sq Ft
$220
17 active listings
Sale-to-List Ratio
107.2%
249 sales
How this home compares
List Price
$299,000
vs $710,000 median
57.9% below median
Price / Sq Ft
$215
vs $220 median
In line with median
Days on Market
8 days
vs 31 days median
23 days fresher than median
Based on 17 active and 249 closed sales (trailing 12 mo) of single family in Simsbury. Source: SmartMLS · As of July 28, 2026.
Location
38 Main Street, Simsbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,525
- Property Taxes$362
- Insurance$100
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Simsbury
- Neighborhood
- Tariffville
- County
- Hartford
Residence
- Property Type
- Single Family
- Style
- Colonial,Antique
- Year Built
- 1900
- New Construction
- No/Resale
- Living Area
- 1,392 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Wall Unit
- Laundry
- Lower Level
- Laundry Location
- Basement
- Appliances
- RefrigeratorOven/Range
- Basement
- Full
- In-Law Apartment
- PossibleFirst FloorSeparate Entry
- Interior Features
- Cable - AvailableOpen Floor Plan
- Accessibility
- Ramps
Exterior & Lot
- Lot Size
- 0.08 acres
- Zoning
- B-2
- Garage / Parking
- 5 total parking spacesOff Street ParkingDrivewayPrivate
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Color
- White
- Roof
- Shingle
- Foundation
- Block
- Exterior Features
- Porch
- Lot Description
- TreedLevel LotHistoric District
Listing & Financials
- Property Taxes
- $4,338 / Annually
- Days on Market
- 8
- MLS #
- 24192818
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 4:25 AM UTC.