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16 Deepwood Drive

Cheshire, Connecticut 06410

ACTIVE$500,000

Reduced from $550,000

Beds
3
Baths
2
SqFt
1,566
Acres
0.42
Year Built
1955
Matt Caiola

Matt Caiola

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,192

per 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

Similar Properties

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

Listed By

Lisa Rollins

(203) 671-0295

Compass Connecticut, LLC

(203) 245-1593

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.