27 Winchester Drive
Shelton, Connecticut 06484
- Beds
- 3
- Baths
- 1 | 1
- SqFt
- 1,649
- Acres
- 1.96
- Year Built
- 1969
- Neighborhood
- Huntington
- 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
Tucked away on nearly 2 private acres in the peaceful, sought-after Huntington neighborhood of Shelton, this modern and low maintenance Ranch style home is as move-in ready as it gets. The thoughtfully finished layout offers 3 well sized bedrooms including a full bath with tub on the main level and a convenient half bath plus laundry on the lower level. The lower level features a large rec room space for entertaining, storage in the extra closets, an attached two car under the home garage and sliders to the flat and nice sized backyard with shed for extra storage. The major mechanicals have been replaced for total peace of mind: a brand-new Navien propane combination furnace and water heater system, zoned separately for each floor, plus a new reverse osmosis water filtration system. Enjoy refinished hardwood floors throughout and the most perfect outdoor entertaining area complete with TV hookup for the sports fans. Recent updates also include all-new window screens, ceiling fans inside and out, and included exterior ambient lighting. This home seamlessly blends curb appeal, privacy, classic charm yet modern comfort, and nature while still being just minutes from Shelton's shops, restaurants, and commuter routes. Your chance to enjoy nearly 2 acres of privacy without sacrificing convenience or having to do any work awaits.
Key Facts
- City/Town
- Shelton
- Neighborhood
- Huntington
- Property / Style
- Single Family · Ranch
- Year Built
- 1969
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 1 full · 1 half
- Living Area
- 1,649 sq ft
- Lot Size
- 1.96 acres
- Garage / Parking
- 2 garage · 4 total
- Property Taxes
- $5,191 / Annually
Market Snapshot
The Shelton Market
Single Family · trailing 12 months
Active Listings
57
64 under contract
Median List Price
$609,900
57 active listings
Median Closed Price
$585,000
288 sales
Median Days on Market
36
57 active listings
Median $ / Sq Ft
$297
57 active listings
Sale-to-List Ratio
100.1%
288 sales
How this home compares
List Price
$613,900
vs $609,900 median
In line with median
Price / Sq Ft
$372
vs $297 median
25.3% above median
Days on Market
0 days
vs 36 days median
36 days fresher than median
Based on 57 active and 288 closed sales (trailing 12 mo) of single family in Shelton. Source: SmartMLS · As of August 16, 2026.
Location
27 Winchester Drive, Shelton, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per month
- Principal & Interest$3,159
- Property Taxes$433
- Insurance$205
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Shelton
- Neighborhood
- Huntington
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1969
- New Construction
- No/Resale
- Living Area
- 1,649 sq ft
- Below Grade
- 400 sq ft
Schools
- Elementary
- Mohegan
- High
- Shelton
Interior
- Heating
- Hot AirZoned
- Heat Fuel
- Propane
- Cooling
- Window Unit
- Fireplaces
- 1
- Laundry
- Lower Level
- Laundry Location
- Lower Level
- Appliances
- Electric RangeMicrowaveRefrigeratorFreezerDishwasherWasherDryer
- Basement
- FullStorageFully FinishedLiveable SpaceFull With Walk-Out
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 1.96 acres
- Zoning
- R-1
- Garage / Parking
- 2 garage spaces4 total parking spacesUnder House GaragePavedOn Street ParkingDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- Wood
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Masonry
- Exterior Features
- ShedDeckLightingCovered Deck
- Lot Description
- Rear LotLightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $5,191 / Annually
- Days on Market
- 0
- MLS #
- 24199568
- MLS Status
- Coming Soon
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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 8/16/2026. 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 8/16/2026 at 6:25 PM UTC.