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385 Sir Walter Drive

Cheshire, Connecticut 06410

COMING SOON - NEW$649,900
Beds
3
Baths
2 | 1
SqFt
2,214
Acres
1.01
Year Built
1961
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage2 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,560

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Daniela Volo

Calcagni Real Estate

(203) 265-1821

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.