16 Deepwood Drive
Cheshire, Connecticut 06410
Reduced from $550,000
- Beds
- 3
- Baths
- 2
- SqFt
- 1,566
- Acres
- 0.42
- Year Built
- 1955
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
A striking transformation awaits with this stunningly remodeled 3 BR, 2 bath Gambrel Cape and its spacious oversized garage. 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 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 garage with a spacious 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. This home has been upgraded for maximum efficiency and peace of mind with its new 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. Enjoy a fantastic community investing $166M in top-tier education with 2 brand new elementary schools opening this fall! Agent related.
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1955
- Days on Market
- 42 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 1,566 sq ft
- Lot Size
- 0.42 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $5,712 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
24
54 under contract
Median List Price
$642,000
24 active listings
Median Closed Price
$553,750
238 sales
Median Days on Market
33
24 active listings
Median $ / Sq Ft
$270
24 active listings
Sale-to-List Ratio
101.6%
238 sales
How this home compares
List Price
$500,000
vs $642,000 median
22.1% below median
Price / Sq Ft
$319
vs $270 median
18.1% above median
Days on Market
42 days
vs 33 days median
9 days longer than median
Based on 24 active and 238 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of July 28, 2026.
Location
16 Deepwood Drive, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,549
- Property Taxes$476
- Insurance$167
- 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
- Cape Cod
- Year Built
- 1955
- New Construction
- No/Resale
- Living Area
- 1,566 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Cheshire
Interior
- Heating
- Hot Air
- Heat Fuel
- Gas In Street
- Cooling
- Window Unit
- Laundry Location
- Basement
- Appliances
- Electric RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinishedConcrete Floor
- Interior Features
- Auto Garage Door OpenerOpen Floor Plan
Exterior & Lot
- Lot Size
- 0.42 acres
- Zoning
- R-20
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl SidingVertical Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGuttersGarden Area
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $5,712 / Annually
- Days on Market
- 42
- MLS #
- 24182948
- MLS Status
- Active
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Co-Listed By
Lisa Szyndlar
Compass Connecticut, LLC
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:55 AM UTC.