16 Deepwood Drive Cheshire, CT $ 550,000
16 Deepwood Drive
$ 550,000
Open House 6/20 11am - 1pm
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16 Deepwood Drive

Cheshire, CT, 06410
$ 550,000
Bedrooms3 Baths2.0 Sq 1,486

Monthly Estimate*

$ 3,386

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Single Family Home for sale in Cheshire, CT

for $550,000 with 3 bedrooms and 2 full baths. This 1,486 square foot home was built in 1955 on a lot size of 0.42.

A striking transformation awaits with this stunningly remodeled 3 bedrm, 2 bath Gambrel Cape and its spacious oversized barn. Completely updated from top to bottom, this is a rare move in ready gem where every detail has been done for you. Enjoy an unbeatable location near dining, shops and a 3 minute stroll to the 11 mile Farmington Canal Heritage Trail! The exterior makes an unforgettable first impression with its beautiful new vertical board and batten siding, brand-new shingle roof, and a level, private backyard shaded by mature trees. The property boasts a massive barn/garage with a spacious, fully insulated loft-ideal for a home studio, workshop, or gym. Step inside to find a sun-drenched floor plan showcasing gleaming hardwood floors and brand-new luxury laminate. The main level offers ultimate flexibility with a primary bedroom that can easily double as a home office. The fully renovated kitchen features sleek quartz countertops and stainless steel appliances, opening directly to a durable composite deck for seamless outdoor entertaining. The dining area is accented by beautiful, custom built-ins. Every system is upgraded for maximum efficiency and peace of mind: energy-efficient windows and doors, new recessed lighting, a new 100-amp electrical panel, natural gas heat, a brand-new hot water heater, city water/sewer connections and underground utilities. All of this in a fantastic community that invests heavily in its top-tier education system.

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Open House

6/20/2026 11:00 AM - 1:00 PM
16 Deepwood Drive Cheshire, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Coming Soon

Price

$ 550,000

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 5,712

Style

Lot Size

0.42

Year Built

1955

Town/City

Cheshire

MLS | Web ID

24182948

Features
General
Zoning R-20
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Coming Soon
Acres 0.42
Directions Route 68 West Main St to Deepwood Drive - First House on Right
High School Cheshire
City Cheshire
Elementary School Per Board of Ed
Sq Ft Total 1486
Year Built 1955
Style Cape Cod
Year Built Source Public Records
Energy Features Thermopane Windows
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Interior
Cooling System Window Unit
Total Rooms 6
Basement Description Full Unfinished Concrete Floor
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Exterior
Water Source Public Water Connected
Lot Description Level Lot
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* Excluded Features
List By
Lisa Rollins

Listing Agent

Compass Connecticut, Llc

Broker

Lisa.Rollins@Compass.com

Email

Affordability Calculator

$3,862
Per Month
88%
12%
0%
Monthly Principal & Interest
$3,386
Monthly Property Taxes
$476
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3041960 Elementary School
1232875 Middle School
Cheshire High School High School
Pricing History
DatePricePrice ChangeDescription
6/15/2026$550,000 Listed Price

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16 Deepwood Drive, Cheshire, CT, 06410 is a Single Family Home for sale at $550,000 with 1,486 sqft and a lot size of 0.42. 16 Deepwood Drive has 3 bedrooms, 2.0 baths, and was built in 1955. The property's zip code is 06410 which is in Cheshire, CT