57 Gay Head Road
Canterbury, Connecticut 06331
- Beds
- 3
- Baths
- 1
- SqFt
- 1,008
- Acres
- 14.46
- Year Built
- 1959
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
7
7 under contract
Median List Price
$595,000
7 active listings
Median Closed Price
$448,000
48 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.