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38 Main Street

Simsbury, Connecticut 06081

ACTIVE - NEW$299,000
Beds
0
Baths
2
SqFt
1,392
Acres
0.08
Year Built
1900
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,987

per 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

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Listed By

Stephanie Stone

(860) 324-7253

William Raveis/First Town RE

(860) 688-1868

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.