368 Charles Drive
Cheshire, Connecticut 06410
- Beds
- 4
- Baths
- 3
- SqFt
- 2,324
- Acres
- 0.94
- Year Built
- 1968
- 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
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
Active Listings
26
39 under contract
Median List Price
$587,000
26 active listings
Median Closed Price
$568,750
256 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per 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
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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.