10 Whispering Hollow Court
Cheshire, Connecticut 06410
Reduced from $1,300,888
- Beds
- 4
- Baths
- 4 | 1
- SqFt
- 4,163
- Acres
- 1.84
- Year Built
- 2005
- 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
A rare opportunity to own a home in one of Cheshire's premier subdivisions. This custom-built brick residence showcases exceptional craftsmanship, featuring 9-foot ceilings and beautiful hardwood floors throughout. The gourmet kitchen blends function and style, complete with granite countertops, a Viking gas range with professional-grade exhaust hood, Viking refrigerator, built-in wall oven, and a wine cooler-perfect for any culinary enthusiast. The spacious primary suite offers a true private retreat, highlighted by a cozy gas fireplace, whirlpool tub, walk-in closet, dressing area, and a charming private reading loft. Designed for both everyday living and entertaining, the home features an open, flowing floor plan that seamlessly connects each living space. Additional highlights include two freshly remodeled bathrooms, a finished basement, and a new high-efficiency boiler and hot water system. Homes in this highly desirable area rarely become available-schedule your showing today and experience it for yourself.
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2005
- Days on Market
- 112 days
- Beds
- 4
- Baths
- 4 full · 1 half
- Living Area
- 4,163 sq ft
- Lot Size
- 1.84 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $20,173 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
20
58 under contract
Median List Price
$642,000
20 active listings
Median Closed Price
$555,000
239 sales
Median Days on Market
31
20 active listings
Median $ / Sq Ft
$271
20 active listings
Sale-to-List Ratio
101.6%
239 sales
How this home compares
List Price
$1.08M
vs $642,000 median
68.4% above median
Price / Sq Ft
$260
vs $271 median
In line with median
Days on Market
112 days
vs 31 days median
81 days longer than median
Based on 20 active and 239 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of July 29, 2026.
Location
10 Whispering Hollow Court, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$5,511
- Property Taxes$1,681
- Insurance$360
- 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
- 2005
- New Construction
- No/Resale
- Living Area
- 4,163 sq ft
- Below Grade
- 900 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Cheshire
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Upper Level
- Laundry Location
- Second floor
- Appliances
- Gas RangeOven/RangeWall OvenMicrowaveRange HoodRefrigeratorSubzeroDishwasherWasherElectric DryerWine Chiller
- Basement
- FullPartially Finished
- Interior Features
- Auto Garage Door OpenerCable - AvailableOpen Floor PlanSecurity System
Exterior & Lot
- Lot Size
- 1.84 acres
- Zoning
- R-80
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- Brick
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Underground UtilitiesGuttersPatio
- Lot Description
- In SubdivisionLightly WoodedLevel LotOn Cul-De-SacProfessionally Landscaped
Listing & Financials
- Property Taxes
- $20,173 / Annually
- Days on Market
- 112
- MLS #
- 24165619
- MLS Status
- Under Contract - Continue to Show
- Financing
- FHA,VA,CHFA,USDA
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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 7/29/2026. 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 7/29/2026 at 12:40 PM UTC.