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16 Deepwood Drive, Cheshire, CT 06410

Single Family For Sale

16 Deepwood Drive, Cheshire, CT
Active
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$465,000
Est. Payment: $3,158/mo  Get Pre-Approved
3
Beds
2
Baths
1,566
Sq Ft
0.42
Acres
1955
Yr Built

About This Home

RENOVATED & REIMAGINED - move in for less than the average Cheshire rent! A seller-paid first-year rate buydown currently saves you $246 per month (ask for details). This 3-bed, 2-bath renovated Gambrel Cape on a sunny corner lot has been rebuilt top to bottom: new roof, board-and-batten siding, new windows and doors, a quartz-and-stainless kitchen, composite deck, NATURAL GAS heat, new water heater, 100-amp service, and city water and sewer. This home has truly been upgraded for maximum efficiency and peace of mind! There's a first-floor primary (or office), a private tree-shaded backyard, and an oversized detached 2-car garage with a loft overhead - room for the cars, the workshop, and the hobby you keep meaning to start. The location sells itself: the house sits just off West Main Street, right where the Farmington Canal Heritage Trail crosses - with miles of paved trail running from New Haven to the Massachusetts line for morning rides, runs, and dog walks, and trailhead parking minutes from your door. Everyday life is close, too: coal-fired pizza, coffee shops, the Cheshire Public Library, and a hardware and lumber yard are all within about a mile, with easy access to I-691 and I-84. Bonus: you'll join a community that truly puts education first-featuring two brand-new elementary schools backed by a massive $166M investment. Agent related.

Listed by Lisa Rollins (203) 671-0295 with Compass Connecticut, LLC (203) 245-1593

Listing Snapshot

Price $465,000 Days on Our Site 147 days
Property Tax $6,024/yr Style Cape Cod
Year Built 1955 Total Sq Ft 1,566
Lot Size 0.42 acres HOA Fees N/A
Bedrooms 3 Full Bathrooms 2
Total Rooms 6 Half Baths 0

Key Features

Interior
  • Auto Garage Door Opener
  • Open Floor Plan
Appliances
  • Electric Range
  • Microwave
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer
Outdoor
  • Deck
  • Gutters
  • Garden Area

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 2
Garage Type Detached Garage

Systems & Utilities

Heat Hot Air
Fuel Gas In Street
Cooling Window Unit
Hot Water Natural Gas, 40 Gallon Tank
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Per Board of Ed
High Cheshire

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $502/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Oct 13, 2026 Price Reduced $465,000
Jun 15, 2026 Listed $550,000

Frequently Asked Questions

How much does 16 Deepwood Drive in Cheshire, CT cost?
This property is listed at $465,000, which works out to $297 per square foot.
How many bedrooms does 16 Deepwood Drive have?
This home has 3 bedrooms and 2 bathrooms.
What is the square footage of 16 Deepwood Drive?
The home is 1,566 square feet, situated on 0.42 acres.
When was 16 Deepwood Drive in Cheshire built?
This property was built in 1955.
Is 16 Deepwood Drive, Cheshire, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 16 Deepwood Drive, Cheshire in?
This home is served by the Cheshire public school system, with Per Board of Ed as the elementary school and Cheshire as the high school.
How do I schedule a tour of 16 Deepwood Drive, Cheshire, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Lisa Rollins · (203) 671-0295

Compass Connecticut, LLC · (203) 245-1593

MLS# 24182948 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Nov 7, 2026 11:40 PM UTC

Est. $3,158/mo
$465,000
3 bd · 2 ba · 1,566 sqft
16 Deepwood Drive, Cheshire, CT 06410