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16 Mountaincrest Drive

Cheshire, Connecticut 06410

ACTIVE - NEW$1,590,000
Beds
5
Baths
4 | 1
SqFt
5,021
Acres
1.90
Year Built
1994
Matt Caiola

Matt Caiola

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Pool3-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$10,928

per 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

Homes with a close match in area, property type, and price.

Listed By

E. Tyler Della Valle

(203) 507-3010

Dow Della Valle

(203) 481-0000

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.