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37 Main Street

North Stonington, Connecticut 06359

COMING SOON - NEW$750,000
Beds
4
Baths
2 | 1
SqFt
3,538
Acres
1.49
Year Built
1791
Matt Caiola

Matt Caiola

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2 Fireplaces

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

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

Property + 8 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,669

per 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

Similar Properties

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

Listed By

Ann Bergendahl

(860) 460-3909

Willow Properties

(860) 415-8374

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.