25 Whispering Hollow Court
Cheshire, Connecticut 06410
- Beds
- 6
- Baths
- 5 | 2
- SqFt
- 10,485
- Acres
- 1.84
- Year Built
- 2004
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to The Cheshire Estate on Whispering Hollow Court. Set on a private 1.84-acre lot in an intimate enclave of homes on a cul-de-sac, this modern brick Colonial offers over 10,000 sf of living space across three levels - a rare opportunity to live comfortably and entertain often. The two-story great room anchors the main level, with French doors opening to the patio, outdoor kitchen, and pool for effortless indoor/outdoor entertaining - enjoy quiet mornings by the water and evenings out back to socialize. The main level also features the primary suite, complete with a private sitting room and fireplace - a true retreat at the end of the day - along with a sunroom and a wood-paneled study. The finished lower level adds a home gym and an indoor basketball court, convertible to a squash or racquetball court, so game nights and workouts happen without ever leaving home. Adding rare flexibility, a semi-private au pair apartment (approx. 40' x 22') includes its own kitchen, full bath, living room, and bedroom - ideal for extended family, live-in help, or guests who want their own space to come and go as they please. This isn't just a home - it's a lifestyle built around space, privacy, and the freedom to live exactly how you want.
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2004
- Days on Market
- 63 days
- Beds
- 6
- Baths
- 5 full · 2 half
- Living Area
- 10,485 sq ft
- Lot Size
- 1.84 acres
- Garage / Parking
- 3 garage · 8 total
- Property Taxes
- $32,785 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
18
44 under contract
Median List Price
$634,450
18 active listings
Median Closed Price
$560,000
252 sales
Median Days on Market
37
18 active listings
Median $ / Sq Ft
$310
18 active listings
Sale-to-List Ratio
102.2%
252 sales
How this home compares
List Price
$1.75M
vs $634,450 median
2.8× the median
Price / Sq Ft
$167
vs $310 median
46.1% below median
Days on Market
63 days
vs 37 days median
26 days longer than median
Based on 18 active and 252 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of September 16, 2026.
Location
25 Whispering Hollow Court, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$9,082
- Property Taxes$2,732
- Insurance$583
- 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
- 2004
- New Construction
- No/Resale
- Living Area
- 10,485 sq ft
- Below Grade
- 2,810 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 4
- Laundry
- Upper Level
- Appliances
- Gas RangeWall OvenMicrowaveRange HoodRefrigeratorSubzeroDishwasher
- Basement
- PartialHeatedCooledInterior AccessWalk-outLiveable Space
- In-Law Apartment
- YesSecond Floor
- Interior Features
- Central Vacuum
- Additional Rooms
- Bonus RoomExercise RoomFoyerGymLaundry RoomSitting Room
Exterior & Lot
- Lot Size
- 1.84 acres
- Zoning
- R-80
- Garage / Parking
- 3 garage spaces8 total parking spacesAttached GaragePavedDrivewayPaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Pool
- HeatedPool HouseSafety FenceSalt WaterIn Ground Pool
- Construction
- Brick
- Color
- Brick
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- French DoorsPatio
- Lot Description
- TreedLevel LotOn Cul-De-Sac
Listing & Financials
- Property Taxes
- $32,785 / Annually
- Days on Market
- 63
- MLS #
- 24190202
- MLS Status
- Under Contract
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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 9/16/2026. 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 9/16/2026 at 9:40 PM UTC.