385 Sir Walter Drive
Cheshire, Connecticut 06410
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,214
- Acres
- 1.01
- Year Built
- 1961
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to this immaculate Colonial nestled in a desirable neighborhood on a level, one-acre lot! This move-in-ready, 3-bedroom, 2.5-bath home offers numerous updates and exceptional living spaces with so much flexibility. The spacious and bright front to back living room features crown molding and fireplace while the formal dining room showcases classic shadow box trim. The custom renovated kitchen features abundant cabinetry, quartz countertops, tile backsplash, newer appliances, and a breakfast bar overlooking the family room which offers built-ins and a window seat. The spectacular sun drenched Great Room boasts a soaring ceiling punctuated with exposed beams, walls of windows, and a stone fireplace with pellet-stove insert that can heat the entire first floor. Upstairs, the expanded primary bedroom includes a fully updated bath and two custom California closets. Additional updates include a new roof, updated windows, and more! This home features fully paid-off solar panels that generate approximately 114% of the home's annual electricity usage, resulting in no electric bills over the past year, making electric heating even more desirable and are under warranty through 2048! Outside, enjoy the level yard with professional landscaping and newer composite deck-perfect for relaxing or entertaining. A wonderful blend of character, comfort, updates, energy efficiency and no electric bills, this home will check all the boxes!
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1961
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 2,214 sq ft
- Lot Size
- 1.01 acres
- Garage / Parking
- 2 garage · 4 total
- Property Taxes
- $9,435 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
29
35 under contract
Median List Price
$599,000
29 active listings
Median Closed Price
$575,000
255 sales
Median Days on Market
22
29 active listings
Median $ / Sq Ft
$278
29 active listings
Sale-to-List Ratio
102.3%
255 sales
How this home compares
List Price
$649,900
vs $599,000 median
8.5% above median
Price / Sq Ft
$294
vs $278 median
5.8% above median
Days on Market
0 days
vs 22 days median
22 days fresher than median
Based on 29 active and 255 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of October 5, 2026.
Location
385 Sir Walter Drive, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 1, 2026per month
- Principal & Interest$3,557
- Property Taxes$786
- Insurance$217
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Cheshire
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1961
- New Construction
- No/Resale
- Living Area
- 2,214 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Cheshire
Interior
- Heating
- Baseboard
- Heat Fuel
- Electric
- Cooling
- Split System
- Fireplaces
- 2
- Appliances
- Oven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- Full
- Interior Features
- Auto Garage Door OpenerCable - Available
Exterior & Lot
- Lot Size
- 1.01 acres
- Zoning
- R-40
- Garage / Parking
- 2 garage spaces4 total parking spacesAttached GarageDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Color
- Cream
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGuttersHot Tub
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $9,435 / Annually
- Days on Market
- 0
- MLS #
- 24211153
- 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 10/5/2026. 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 10/5/2026 at 5:50 PM UTC.