16 Mountaincrest Drive
Cheshire, Connecticut 06410
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 5,021
- Acres
- 1.90
- Year Built
- 1994
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Perched high above the landscape of South Cheshire, this extraordinary custom-built Colonial is a residence of uncommon beauty, privacy, and scale. Set against the natural backdrop of Bethany Mountain and surrounded by meticulously maintained, park-like grounds, this exceptional 4/5-bedroom home captures magnificent views, abundant sunshine, and a remarkable sense of tranquility. From the moment you arrive, there is an unmistakable feeling that this is something special. Thoughtfully designed and impeccably cared for, the home combines the timeless elegance of classic Colonial architecture with the openness and amenities expected of today's finest residences. Inside, soaring ceilings, gleaming hardwood floors, and an inviting open floor plan create an effortless connection between the home's gracious living spaces. At its center is a beautifully appointed gourmet kitchen, equally impressive as a gathering place for family and friends or as the culinary heart of sophisticated entertaining. The main level continues with an elegant formal living room, formal dining room, private library, laundry room, and oversized three-car garage, providing an exceptional balance of formal spaces, everyday comfort, and practical convenience.
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1994
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 4 full · 1 half
- Living Area
- 5,021 sq ft
- Lot Size
- 1.90 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $25,662 / 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
$1.59M
vs $634,450 median
2.5× the median
Price / Sq Ft
$317
vs $310 median
In line with median
Days on Market
0 days
vs 37 days median
37 days fresher 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
16 Mountaincrest Drive, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$8,259
- Property Taxes$2,139
- Insurance$530
- 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
- 1994
- New Construction
- No/Resale
- Living Area
- 5,021 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 1
- Laundry
- Lower LevelMain Level
- Appliances
- Electric CooktopWall OvenMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullFully FinishedFull With Walk-Out
- In-Law Apartment
- PossibleLower Level
- Additional Rooms
- Bonus RoomFoyer
Exterior & Lot
- Lot Size
- 1.90 acres
- Zoning
- R-80
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- HeatedLap Pool
- Construction
- Clapboard
- Roof
- Asphalt ShingleGable
- Foundation
- Concrete
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $25,662 / Annually
- Days on Market
- 0
- MLS #
- 24207532
- MLS Status
- Active
Similar Properties
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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 9:30 PM UTC.