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368 Charles Drive

Cheshire, Connecticut 06410

ACTIVE - NEW$769,000
Beds
4
Baths
3
SqFt
2,324
Acres
0.94
Year Built
1968
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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1-Car Garage1 FireplaceVirtual Tour

About This Home

Welcome to this completely remodeled home w/ a private In-law apartment in a highly desirable Cheshire neighborhood! Set on a spacious 1-acre lot, this truly move-in-ready property has been extensively renovated from top to bottom. The main living level features 3 BR & 2 full BA, offering comfortable & inviting living spaces throughout. The newly renovated kitchen is the heart of the home, featuring brand-new appliances, perfect for everyday living & entertaining. All new flooring throughout! Step outside through the DR onto the new deck, the perfect setting for family gatherings. The professionally landscaped, level yard is enhanced by a charming stone wall, an irrigation system, & a brand-new patio. A truly exceptional feature of this property is the brand-new, beautifully finished in-law apartment, complete w/ its own private entrance. This thoughtfully designed living space offers a separate BR, full BA, living room, beautiful eat-in kitchen & washer dryer hookups. This private suite offers comfort, convenience, & endless possibilities. The extensive list of improvements includes a new roof, new windows, multiple new split-units heating & cooling system, new hot water heater, brand-new septic system, & solar panels. This is a rare opportunity to own a meticulously renovated Cheshire home with an in-law apartment that is set on a picturesque acre of land in a sought-after location. Simply unpack, settle in, and enjoy everything this extraordinary property has to offer!

Key Facts

City/Town
Cheshire
Neighborhood
N/A
Property / Style
Single Family · Raised Ranch
Year Built
1968
Days on Market
0 days
Beds
4
Baths
3 full
Living Area
2,324 sq ft
Lot Size
0.94 acres
Garage / Parking
1 garage
Property Taxes
$8,660 / Annually

Market Snapshot

The Cheshire Market

Single Family · trailing 12 months

Median Days on Market

23

26 active listings

Median $ / Sq Ft

$283

26 active listings

Sale-to-List Ratio

102.3%

256 sales

How this home compares

List Price

$769,000

vs $587,000 median

31.0% above median

Price / Sq Ft

$331

vs $283 median

17.0% above median

Days on Market

0 days

vs 23 days median

23 days fresher than median

Based on 26 active and 256 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of September 26, 2026.

Location

368 Charles Drive, Cheshire, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,083

per month

  • Principal & Interest$4,105
  • Property Taxes$722
  • Insurance$256
  • 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
Raised Ranch
Year Built
1968
New Construction
No/Resale
Living Area
2,324 sq ft
Below Grade
1,088 sq ft

Schools

Elementary
Per Board of Ed
High
Cheshire

Interior

Heating
Baseboard
Heat Fuel
Electric
Cooling
Split System
Fireplaces
1
Laundry
Lower Level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherDisposalWasherDryer
Basement
FullHeatedStorageFully FinishedApartmentWalk-outLiveable Space
In-Law Apartment
YesLower LevelSeparate Entry
Interior Features
Cable - AvailableOpen Floor Plan

Exterior & Lot

Lot Size
0.94 acres
Zoning
R-40
Garage / Parking
1 garage spaceAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckUnderground SprinklerPatio
Lot Description
Level Lot

Listing & Financials

Property Taxes
$8,660 / Annually
Days on Market
0
MLS #
24208525
MLS Status
Active
Financing
FHA,VA,CHFA

Similar Properties

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

Listed By

Kristy Agli

(203) 671-1625

Kelsey & Co. Real Estate

(203) 295-0432

Co-Listed By

Gerald Raccio

Kelsey & Co. Real Estate

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/26/2026. 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 9/26/2026 at 7:10 PM UTC.