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57 Gay Head Road

Canterbury, Connecticut 06331

PENDING$300,000
Beds
3
Baths
1
SqFt
1,008
Acres
14.46
Year Built
1959
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage

About This Home

Set on approximately 14.46 acres, this well-loved 3-bedroom, 1-bath ranch offers a rare opportunity for investors, contractors, or buyers looking to create their dream country property. Whether you're seeking privacy, recreation, or future potential, the expansive acreage may offer subdivision potential (buyer to perform their own due diligence). The home features a functional layout with a sun-filled living room, a dining room, and a kitchen with a breakfast bar. Outside, you'll find a detached 2-car carriage shed/garage along with acres of land to enjoy, explore, or potentially develop. While the home is in need of updating and is being sold as a handyman special, the seller reports several important improvements completed within the past three years, including updated electrical wiring with a new electrical panel, a new well pump, new pressure tank, and a new water heater. Bring your vision and discover the possibilities this unique property has to offer.

Key Facts

City/Town
Canterbury
Neighborhood
N/A
Property / Style
Single Family · Ranch
Year Built
1959
Days on Market
33 days
Beds
3
Baths
1 full
Living Area
1,008 sq ft
Lot Size
14.46 acres
Garage / Parking
2 garage
Property Taxes
$3,183 / Annually

Market Snapshot

The Canterbury Market

Single Family · trailing 12 months

Median Days on Market

10

7 active listings

Median $ / Sq Ft

$290

7 active listings

Sale-to-List Ratio

101.7%

48 sales

How this home compares

List Price

$300,000

vs $595,000 median

49.6% below median

Price / Sq Ft

$298

vs $290 median

In line with median

Days on Market

33 days

vs 10 days median

23 days longer than median

Based on 7 active and 48 closed sales (trailing 12 mo) of single family in Canterbury. Source: SmartMLS · As of July 28, 2026.

Location

57 Gay Head Road, Canterbury, Connecticut

Property + 6 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,895

per month

  • Principal & Interest$1,530
  • Property Taxes$265
  • Insurance$100
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Canterbury
Neighborhood
N/A
County
Windham

Residence

Property Type
Single Family
Style
Ranch
Year Built
1959
New Construction
No/Resale
Living Area
1,008 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Per Board of Ed

Interior

Heating
No Heat
Cooling
None
Appliances
Oven/RangeRefrigerator
Basement
FullUnfinishedHatchway Access

Exterior & Lot

Lot Size
14.46 acres
Zoning
RES
Garage / Parking
2 garage spacesDetached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Wood
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Treed

Listing & Financials

Property Taxes
$3,183 / Annually
Days on Market
33
MLS #
24184766
MLS Status
Under Contract

Similar Properties

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

Listed By

Kara Mazzola

(860) 933-7337

First Choice Realty

(860) 779-7460

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 7:50 AM UTC.