37 Main Street
North Stonington, Connecticut 06359
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 3,538
- Acres
- 1.49
- Year Built
- 1791
- 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
Set in the heart of North Stonington Village, this 1791 home is sure to have many stories to tell. The current owner has called it home for more than 40 years and, as a local carpenter and woodworker, thoughtfully updated and cared for the property throughout the 1980s and beyond. The kitchen is truly the heart of the home, featuring custom cabinetry, a cozy wood stove, and a charming window seat. All of the fireplaces remain in working condition, and many of the windows have been rebuilt or replaced by the current owner. The first floor also offers a study/office with an adjoining powder room that could potentially be converted into a small first-floor bedroom. At the rear of the home is a woodshop, which allowed much of the restoration and woodworking to be done on-site. Upstairs, numerous bedrooms and flexible spaces await your vision. A rear living room connects to a laundry room, study, small bedroom, and storage, with a second staircase leading down to the first floor. The basement features high ceilings and a garage sized for a small car. Nearly 11/2 acres provide the best of both worlds-the charm of village living with the feeling of a country property. Two sheds sit in the rear field/pasture, while beautiful stone steps lead down to the stream along the property's rear boundary, where an old shed once sheltered the sheep that lived here for 30 years. A truly magical property, inside and out.
Key Facts
- City/Town
- North Stonington
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1791
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 3,538 sq ft
- Lot Size
- 1.49 acres
- Property Taxes
- $6,761 / Annually
Market Snapshot
The North Stonington Market
Single Family · trailing 12 months
Active Listings
14
8 under contract
Median List Price
$389,950
14 active listings
Median Closed Price
$474,900
61 sales
Median Days on Market
68
14 active listings
Median $ / Sq Ft
$272
14 active listings
Sale-to-List Ratio
101.1%
61 sales
How this home compares
List Price
$750,000
vs $389,950 median
92.3% above median
Price / Sq Ft
$212
vs $272 median
22.1% below median
Days on Market
0 days
vs 68 days median
68 days fresher than median
Based on 14 active and 61 closed sales (trailing 12 mo) of single family in North Stonington. Source: SmartMLS · As of September 4, 2026.
Location
37 Main Street, North Stonington, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$3,856
- Property Taxes$563
- Insurance$250
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- North Stonington
- Neighborhood
- N/A
- County
- New London
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1791
- New Construction
- No/Resale
- Living Area
- 3,538 sq ft
Schools
- Elementary
- North Stonington
- High
- Wheeler
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Upper Level
- Appliances
- Gas CooktopOven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullConcrete Floor
Exterior & Lot
- Lot Size
- 1.49 acres
- Zoning
- R40
- Waterfront Details
- Not Applicable
- Water Source
- Public Water In StreetPrivate Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- olive green/tan
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Rolling
Listing & Financials
- Property Taxes
- $6,761 / Annually
- Days on Market
- 0
- MLS #
- 24201984
- MLS Status
- Coming Soon
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Co-Listed By
Erika Rossetto
Willow Properties
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/4/2026. 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 9/4/2026 at 2:11 AM UTC.