441 Platt Hill Road
Winchester, Connecticut 06098
Reduced from $499,900
- Beds
- 5
- Baths
- 3
- SqFt
- 3,404
- Acres
- 2.09
- Year Built
- 1975
- Neighborhood
- Sucker Brook
- 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 2.09 private acres in the desirable Platt Hill area of Winchester, this custom-built contemporary offers the perfect blend of architectural character, space, and recent updates. With over 3,400 square feet, 5 bedrooms, 3 full baths, and a 2-car garage, this home provides flexibility for everyday living, entertaining, or multi-generational needs. Inside, you'll find a thoughtfully designed layout with an open, airy feel, highlighted by hardwood floors in the living room, two fireplaces, and abundant natural light throughout. The spacious main living areas offer the ideal balance of openness and comfort, creating inviting spaces to gather while still maintaining warmth and definition. Major improvements including a newer roof and windows provide peace of mind, while the expansive yard offers endless possibilities for outdoor enjoyment, recreation, gardening, or simply enjoying the privacy and natural surroundings. A rare opportunity to own a distinctive contemporary home with room to grow in one of Winchester's most scenic settings.
Key Facts
- City/Town
- Winchester
- Neighborhood
- Sucker Brook
- Property / Style
- Single Family · Contemporary
- Year Built
- 1975
- Days on Market
- 63 days
- Beds
- 5
- Baths
- 3 full
- Living Area
- 3,404 sq ft
- Lot Size
- 2.09 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $6,716 / 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
40
12 active listings
Median $ / Sq Ft
$265
12 active listings
Sale-to-List Ratio
100.0%
103 sales
How this home compares
List Price
$474,900
vs $524,900 median
9.5% below median
Price / Sq Ft
$140
vs $265 median
47.2% below median
Days on Market
63 days
vs 40 days median
23 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 29, 2026.
Location
441 Platt Hill Road, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,421
- Property Taxes$560
- Insurance$158
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- Sucker Brook
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 1975
- New Construction
- No/Resale
- Living Area
- 3,404 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Oven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinishedFull With Hatchway
- Interior Features
- Central Vacuum
Exterior & Lot
- Lot Size
- 2.09 acres
- Zoning
- RU-3
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Shingle
- Color
- Grey
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedDeckGarden Area
- Lot Description
- ClearedRolling
Listing & Financials
- Property Taxes
- $6,716 / Annually
- Days on Market
- 63
- MLS #
- 24178677
- MLS Status
- Under Contract
- Financing
- FHA,VA,CHFA,Renovation,USDA
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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 7/29/2026. 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 7/29/2026 at 11:05 AM UTC.