184 Smith Hill Road
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 4,387
- Acres
- 8.46
- Year Built
- 1988
- Neighborhood
- Smith Hill
- 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
Beautiful Private Brick/Clapboard Tudor set back on 8.46 private acres (which includes an extra 2+ acre abutting lot). New Hand Split Cedar Shingled Roof and new rebuilt brick chimney set off this custom elegant home. All warm cherry wood floors and special custom moldings throughout the home add charm. Classy center island Kit with new subzero, granite counters & bow window-Fireplaced Dining room opens to large back deck overlooking fenced in private backyard-Massive sunken fireplaced living room -1st floor office-Private fireplaced Family room-huge master suite with fireplaced sitting room,walk-in closet & thermo-spa master bath. Large upper level bonus room with cozy private office-CAIR& whole house generator system are pluses-Beautiful professionally landscaped private level yard add lasting ambiance to this special home
Key Facts
- City/Town
- Winchester
- Neighborhood
- Smith Hill
- Property / Style
- Single Family · European,Tudor
- Year Built
- 1988
- Days on Market
- 81 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 4,387 sq ft
- Lot Size
- 8.46 acres
- Garage / Parking
- 3 garage · 3 total
- Property Taxes
- $11,386 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
12
12 under contract
Median List Price
$524,900
12 active listings
Median Closed Price
$325,000
103 sales
Median Days on Market
39
12 active listings
Median $ / Sq Ft
$265
12 active listings
Sale-to-List Ratio
100.0%
103 sales
How this home compares
List Price
$765,000
vs $524,900 median
45.7% above median
Price / Sq Ft
$174
vs $265 median
34.3% below median
Days on Market
81 days
vs 39 days median
42 days longer than median
Based on 12 active and 103 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of July 28, 2026.
Location
184 Smith Hill Road, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,901
- Property Taxes$949
- Insurance$255
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- Smith Hill
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- European,Tudor
- Year Built
- 1988
- New Construction
- No/Resale
- Living Area
- 4,387 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Gilbert
Interior
- Heating
- Hot AirHydro AirZoned
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 3
- Laundry
- Main Level
- Appliances
- Gas CooktopWall OvenMicrowaveRange HoodSubzeroIcemakerDishwasherWasherDryer
- Basement
- FullUnfinishedInterior AccessConcrete Floor
- In-Law Apartment
- No
- Interior Features
- Auto Garage Door OpenerCable - AvailableOpen Floor PlanSecurity System
- Additional Rooms
- Bonus RoomSitting Room
Exterior & Lot
- Lot Size
- 8.46 acres
- Zoning
- R-2
- Garage / Parking
- 3 garage spaces3 total parking spacesAttached GarageCovered GarageDrivewayPrivate
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Construction
- ClapboardBrick
- Color
- BROWN
- Roof
- Wood Shingle
- Foundation
- Concrete
- Exterior Features
- Porch-Wrap AroundShedPorchDeckGuttersLightingStone WallFrench DoorsPatio
- Lot Description
- Fence - PrivacySecludedLightly WoodedLevel LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $11,386 / Annually
- Days on Market
- 81
- MLS #
- 24173895
- MLS Status
- Under Contract - Continue to Show
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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 6:10 AM UTC.