21 Berkshire Court
Cheshire, Connecticut 06410
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,873
- Acres
- 0.59
- Year Built
- 1986
- 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 21 Berkshire Court, a beautifully updated 4-bedroom, 2.5-bath Colonial offering 2,373 square feet of living space plus approximately 500 additional square feet in the beautifully finished lower level. Set on a manicured .59-acre lot, this impressive home features thoughtfully designed renovations, wonderful living spaces, and exceptional curb appeal. The heart of the home is the gorgeous expanded kitchen featuring a breakfast bar, abundant cabinetry, and custom built-ins, all opening seamlessly to the inviting family room with additional custom built-ins and French doors leading to the large deck. Just off the kitchen is a highly functional laundry area with additional cabinetry and a convenient coffee bar, along with access to the half bath and attached two-car garage. A formal dining room, spacious living room, and beautiful entryway complete the main level, which features hardwood flooring throughout. Upstairs, the primary suite offers a walk-in closet and beautifully appointed full bath with double sinks and a walk-in shower. Three additional bedrooms and a second full bath complete the upper level. The beautifully finished lower-level rec room is perfect for entertaining, a home gym, playroom, media room, or home office, while still offering plenty of storage. Outside, enjoy the beautifully manicured yard and large deck overlooking the private backyard. Conveniently located close to the center of town with easy access to parks, restaurants & shopping!!
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1986
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,873 sq ft
- Lot Size
- 0.59 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $10,857 / Annually
- HOA Fee
- $350 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
31
36 under contract
Median List Price
$599,000
31 active listings
Median Closed Price
$572,500
254 sales
Median Days on Market
19
31 active listings
Median $ / Sq Ft
$278
31 active listings
Sale-to-List Ratio
102.4%
254 sales
How this home compares
List Price
$725,000
vs $599,000 median
21.0% above median
Price / Sq Ft
$252
vs $278 median
9.4% below median
Days on Market
0 days
vs 19 days median
19 days fresher than median
Based on 31 active and 254 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of October 1, 2026.
Location
21 Berkshire Court, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$3,870
- Property Taxes$905
- Insurance$242
- HOA$29
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
- 1986
- New Construction
- No/Resale
- Living Area
- 2,873 sq ft
- Below Grade
- 500 sq ft
Schools
- Elementary
- Highland
- High
- Cheshire
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Off of Kitchen
- Appliances
- Gas RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullHeatedSump PumpFully FinishedCooledFull With Walk-Out
- Interior Features
- Auto Garage Door OpenerCable - Available
- Additional Rooms
- FoyerLaundry Room
Exterior & Lot
- Lot Size
- 0.59 acres
- Zoning
- R-40
- Garage / Parking
- 2 garage spaces6 total parking spacesAttached GaragePavedDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Wood
- Color
- Blue
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGutters
- Lot Description
- Borders Open SpaceLevel LotOn Cul-De-Sac
HOA / Association
- Fee
- $350 / Annually
Listing & Financials
- Property Taxes
- $10,857 / Annually
- Days on Market
- 0
- MLS #
- 24210753
- MLS Status
- Active
- Financing
- FHA,VA,CHFA
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Co-Listed By
Katie Smith
Berkshire Hathaway NE Prop.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/1/2026. 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 10/1/2026 at 5:05 PM UTC.