25 Charter Oak Drive
Cheshire, Connecticut 06410
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,440
- Acres
- 2.16
- Year Built
- 1996
- 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
Tucked away in a quiet neighborhood, this 4-bedroom Colonial showcases exceptional pride of ownership inside and out. Set on beautifully manicured, park-like grounds, the backyard is a destination all its own, designed for entertaining, recreation, and relaxation. Enjoy a half-court basketball court that also accommodates pickleball, a putting green, a spacious patio, a covered pavilion with TV and surround sound, an above-ground pool, and plenty of room to gather and enjoy the outdoors. Inside, hardwood flooring flows throughout the home, while inviting living spaces and a spacious kitchen provide the perfect setting for both entertaining and unwinding. The flexible layout offers comfortable spaces for hosting guests, celebrating special occasions, or simply enjoying a quiet evening at home. Meticulously maintained and thoughtfully improved, this home reflects a level of care that is rarely found. With substantial recent investment and an extensive list of improvements available for review, this property offers a unique opportunity to enjoy a home that has been exceptionally cared for and designed to be enjoyed for years to come.
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1996
- Days on Market
- 44 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,440 sq ft
- Lot Size
- 2.16 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $11,294 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
24
54 under contract
Median List Price
$642,000
24 active listings
Median Closed Price
$553,750
238 sales
Median Days on Market
33
24 active listings
Median $ / Sq Ft
$270
24 active listings
Sale-to-List Ratio
101.6%
238 sales
How this home compares
List Price
$749,900
vs $642,000 median
16.8% above median
Price / Sq Ft
$307
vs $270 median
13.7% above median
Days on Market
44 days
vs 33 days median
11 days longer than median
Based on 24 active and 238 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of July 28, 2026.
Location
25 Charter Oak Drive, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,824
- Property Taxes$941
- Insurance$250
- 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
- 1996
- New Construction
- No/Resale
- Living Area
- 2,440 sq ft
Schools
- Elementary
- Barnum Elementary
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Ceiling FansCentral AirSplit System
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Cook TopWall OvenMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinishedStorageInterior AccessConcrete FloorFull With Hatchway
- Interior Features
- Auto Garage Door OpenerCable - AvailableCentral Vacuum
Exterior & Lot
- Lot Size
- 2.16 acres
- Zoning
- R-80
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- VinylAbove Ground Pool
- Construction
- Vinyl Siding
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedCabanaGuttersGarden AreaStone WallUnderground SprinklerPatio
- Lot Description
- SecludedIn SubdivisionLightly WoodedDryProfessionally LandscapedOpen Lot
Listing & Financials
- Property Taxes
- $11,294 / Annually
- Days on Market
- 44
- MLS #
- 24183898
- MLS Status
- Under Contract - Continue to Show
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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 7/28/2026. 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 7/28/2026 at 6:01 AM UTC.