Date
Details
Price
Change
Source
7/23/2026
Listed
$1,748,600
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
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.
Full Property Details
Full Property Details for 25 Whispering Hollow Ct
General
- Price: $1,748,600
- Taxes: (July 2026-June 2027)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24190202
- Updated: 7/25/2026
- Added to Site: 32 day(s) ago
Interior
- Number of Rooms: 17
- Rooms/Areas: Bonus Room, Exercise Room, Foyer, Gym, Laundry Room, Sitting Room
- Interior Features: Central Vacuum
- Fireplace: Yes
- Number of Fireplaces: 4
- Appliances: Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Subzero, Dishwasher
Rooms
Bathrooms
- Total Bathrooms: 7
- Full Bathrooms: 5
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 6
- Primary Suite: Main
- Bedroom 1: Bedroom, Upper
- Bedroom 2: Bedroom - 9 ft+ Ceilings, 14 x 12, Upper
- Bedroom 3: Bedroom - 9 ft+ Ceilings, Jack & Jill Bath, Walk-In Closet, 14 x 14, Upper
- Bedroom 4: Bedroom - 9 ft+ Ceilings, Walk-In Closet, 18 x 18, Upper
- Bedroom 5: Bedroom - 9 ft+ Ceilings, Built-Ins, Jack & Jill Bath, Walk-In Closet, 23 x 14, Upper
Other Rooms
- Living Room: Living Room - 9 ft+ Ceilings, Gas Log Fireplace, Hardwood Floor, 16 x 14, Main
- Great Room: Great Room - Cathedral Ceiling, Beams, Built-Ins, Fireplace, Interior Balcony, Hardwood Floor, 25 x 26, Main
- Kitchen: Kitchen - Breakfast Bar, Pantry, 24 x 18, Main
- Dining Room: Dining Room - Bay/Bow Window, Patio/Terrace, Tile Floor, 17 x 13, Main
- Formal Dining Room: Formal Dining Room - 9 ft+ Ceilings, Hardwood Floor, 15 x 17, Main
- Study: Built-Ins, 14 x 14, Main
- Laundry: Upper Level
- In-Law/Au Pair Suite: Yes
Additional Information
- Pool: Yes
- Pool Description: Heated, Pool House, Safety Fence, Salt Water, In Ground Pool
Exterior
- Exterior Features: French Doors, Patio
- Color: Brick
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Total Spaces: 8
- Parking: Attached Garage, Paved, Driveway
Location
- County: New Haven
- Driving Directions: GPS Friendly
School Information
- Elementary School: Per Board of Ed
- High School: Per Board of Ed
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Oil
- Heating Fuel: Oil
- Water Heater: Oil, Tank Size Unknown
Utilities
- Sewer: Septic
- Water: Public Water Connected
Structural Information
- Architectural Style: Colonial
- Construction Status: No/Resale
- Exterior Const.: Brick
- Basement Desc.: Partial, Heated, Cooled, Interior Access, Walk-out, Liveable Space
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 10,485
- Above Ground: 7,675 Sq. Ft.
- Below Ground: 2,810 Sq. Ft.
- Year Built: 2004
Lot Features
- Lot Size (Acres): 1.84
- Driveway/Sidewalk: Paved
- Zoning: R-80
- Lot Description: Treed, Level Lot, On Cul-De-Sac
Financial Considerations
- Assessment Amount: $1,045,520
- Tax Year: July 2026-June 2027
Disclosures and Reports
- Exclusions: Waterford chandelier in dining room
- Property ID: 2341051
Listed by William Raveis Real Estate, Santos & Team, George Santos
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 25 Whispering Hollow Ct —
George Santos
William Raveis Real Estate
Agent Contact: (860) 558-8595 Office Contact: (860) 677-4661
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 25 Whispering Hollow Ct
School District:Cheshire School District
| Name | Grades | Distance |
|---|---|---|
Norton School 414 North Brooksvale Road, Cheshire, CT 06410 | 1-6 | 0.8 mi |
Dodd Middle School 100 Park Place, Cheshire, CT 06410 | 7-8 | 2.7 mi |
Cheshire High School 525 South Main Street, Cheshire, CT 06410 | 9-12 | 1.5 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 25 Whispering Hollow Ct
Tax History
Tax History for 25 Whispering Hollow Ct
Year
Property Taxes
Change
Tax Assessment
Change
2025
$31,094
8%
$1,045,520
—
2023
$28,710
-1%
$1,045,520
26%
2023
$29,072
2%
$828,500
—
2022
$28,434
2%
$828,500
—
2021
$27,937
2%
$828,500
—
2020
$27,523
—
$828,500
—
2019
$27,523
-8%
$828,500
-10%
2018
$30,038
2%
$920,840
—
2017
$29,412
2%
$920,840
—
2016
$28,721
2%
$920,840
—
2015
$28,261
1%
$920,840
—
2014
$27,855
7%
$920,840
-3%
2011
$26,082
—
$945,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 25 Whispering Hollow Ct
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Sold by Marsha Penna
25 Whispering Hollow Court, Cheshire, CT 06410 (MLS# 24190202) is a Single Family property with 6 bedrooms, 5 full bathrooms and 2 partial bathrooms. 25 Whispering Hollow Court is currently listed for $1,748,600 and was received on July 14, 2026. Want to learn more about 25 Whispering Hollow Court? Do you have questions about finding other Single Family real estate for sale in Cheshire? You can browse all Cheshire real estate or contact a Coldwell Banker agent to request more information.