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$649,900 Coming Soon

  • For Sale
  • Coming Soon
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,214 Sq. Ft.
  • 2 Car Garage
  • Updated 3 days ago

Next open house:

Open House: 12:00 PM - 2:00 PM

Saturday 10/17 12:00 PM - 2:00 PM

385 Sir Walter Drive,Cheshire, CT 06410

385 Sir Walter DriveCheshireCT06410

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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!

Full Property Details for 385 Sir Walter Dr

General

  • Price: $649,900
  • Taxes: (July 2026-June 2027)
  • Status: Coming Soon
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24211153
  • Updated: 10/5/2026
  • Added to Site: 5 day(s) ago
  • Expected Market Date: 10/11/2026

Interior

  • Number of Rooms: 8
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Ceiling Fan, Dressing Room, Full Bath, Stall Shower, Hardwood Floor, Upper
  • Bedroom 1: Bedroom - Ceiling Fan, Hardwood Floor, Upper
  • Bedroom 2: Bedroom - Ceiling Fan, Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, Main
  • Family Room: Family Room - Vaulted Ceiling, Beams, Ceiling Fan, Main
  • Dining Room: Dining Room - Hardwood Floor, Main
  • Office: Office - Hardwood Floor, Main

Exterior

  • Exterior Features: Deck, Gutters, Hot Tub
  • Color: Cream

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 4
  • Parking: Attached Garage, Driveway

Location

  • County: New Haven
  • Driving Directions: Wallingford Rd to Sir Walter Drive

School Information

  • Elementary School: Per Board of Ed
  • High School: Cheshire

Heating & Cooling

  • Cooling Type: Split System
  • Heating Type: Baseboard, Electric
  • Heating Fuel: Electric
  • Water Heater: Electric, Upright Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,214
  • Above Ground: 2,214 Sq. Ft.
  • Year Built: 1961

Lot Features

  • Lot Size (Acres): 1.01
  • Driveway/Sidewalk: Private, Paved
  • Zoning: R-40
  • Lot Description: Level Lot

Financial Considerations

  • Assessment Amount: $300,860
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 1086074

Listed by Calcagni Real Estate, Daniela Volo

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Listing agent

— 385 Sir Walter Dr —

  • Daniela Volo

    Calcagni Real Estate

Agent Contact: (203) 265-1821 Office Contact: (203) 265-1821

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 385 Sir Walter Dr

School District:Cheshire School District
NameGradesDistance
Highland School, Cheshire, CT
490 Highland Avenue, Cheshire, CT 06410
1-61.8 mi
Dodd Middle School
100 Park Place, Cheshire, CT 06410
7-82.1 mi
Cheshire High School
525 South Main Street, Cheshire, CT 06410
9-121.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 385 Sir Walter Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/04/2026
Listed
$649,900
80.58%
MLS
6/13/2019
Sold
$359,900
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 385 Sir Walter Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,948
8%
$300,860
—
2023
$8,262
12%
$300,860
43%
2023
$7,368
2%
$209,970
—
2022
$7,206
2%
$209,970
—
2021
$7,080
2%
$209,970
—
2020
$6,975
—
$209,970
—
2019
$6,975
1%
$209,970
-1%
2018
$6,923
2%
$212,220
—
2017
$6,778
2%
$212,220
—
2016
$6,619
2%
$212,220
—
2015
$6,513
1%
$212,220
—
2014
$6,420
6%
$212,220
-4%
2011
$6,084
—
$220,450
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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with our affiliated lender
NMLS#: 1598647

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Listed by Calcagni Real Estate, Daniela Volo

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385 Sir Walter Drive, Cheshire, CT 06410 (MLS# 24211153) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 385 Sir Walter Drive is currently listed for $649,900 and was received on October 04, 2026. Want to learn more about 385 Sir Walter Drive? Do you have questions about finding other Single Family real estate for sale in Cheshire? You can browse all Cheshire real estate or contact a Coldwell Banker agent to request more information.

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