68 Pleasant Drive
Cheshire, Connecticut 06410
- Beds
- 5
- Baths
- 3
- SqFt
- 1,478
- Acres
- 0.56
- Year Built
- 1964
- 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 68 Pleasant Drive, where a potential in-law suite with its own private entrance offers flexibility for extended family or guests. Hardwood floors, a spacious floor plan, and a convenient Cheshire location create a wonderful place to call home. Sidewalks line the road, adding to the appeal of this walkable setting close to shopping and local restaurants. The large backyard offers plenty of room for outdoor entertaining, gardening, or simply relaxing in privacy. Enjoy space, versatility, and everyday convenience in an established neighborhood. Showings begin tomorrow!
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Split Level
- Year Built
- 1964
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 3 full
- Living Area
- 1,478 sq ft
- Lot Size
- 0.56 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,890 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
26
37 under contract
Median List Price
$624,450
26 active listings
Median Closed Price
$575,000
255 sales
Median Days on Market
23
26 active listings
Median $ / Sq Ft
$278
26 active listings
Sale-to-List Ratio
102.6%
255 sales
How this home compares
List Price
$469,000
vs $624,450 median
24.9% below median
Price / Sq Ft
$317
vs $278 median
14.0% above median
Days on Market
0 days
vs 23 days median
23 days fresher than median
Based on 26 active and 255 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of October 15, 2026.
Location
68 Pleasant Drive, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per month
- Principal & Interest$2,598
- Property Taxes$658
- Insurance$156
- 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
- Split Level
- Year Built
- 1964
- New Construction
- No/Resale
- Living Area
- 1,478 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Cheshire
Interior
- Heating
- Baseboard
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Appliances
- Refrigerator
- Basement
- Partial
Exterior & Lot
- Lot Size
- 0.56 acres
- Zoning
- R-20
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- In SubdivisionTreedLevel Lot
Listing & Financials
- Property Taxes
- $7,890 / Annually
- Days on Market
- 0
- MLS #
- 24214579
- MLS Status
- Coming Soon
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/15/2026. 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 10/15/2026 at 9:06 PM UTC.