For Sale
Price CutPrice Drop: $10K (10/13)
Single family home for sale at 16 Deepwood Dr, Cheshire, CT 06410 | MLS# 24182948 | Listing updated on 2026-11-04
Photo 1 of Single family home for sale at 16 Deepwood Dr, Cheshire, CT 06410 | MLS# 24182948 | Listing updated on 2026-11-04
Photo 2 of Single family home for sale at 16 Deepwood Dr, Cheshire, CT 06410 | MLS# 24182948 | Listing updated on 2026-11-04
Photo 3 of Single family home for sale at 16 Deepwood Dr, Cheshire, CT 06410 | MLS# 24182948 | Listing updated on 2026-11-04
Photo 4 of Single family home for sale at 16 Deepwood Dr, Cheshire, CT 06410 | MLS# 24182948 | Listing updated on 2026-11-04
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$465,000

Monthly Est:$2,314

  • Beds Icon3 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,566sqft

16 Deepwood Dr, Cheshire, CT 06410

$2,314/moEst:

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  • Single Family Residence

  • Built in 1955

  • $-- HOA

  • 18,295.2 sqft lot

  • $297/sq.ft

Description

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.

  • Houzeo last checked: 10 minutes ago
  • Listing updated: November 4, 2026 at 4:14 pm
  • Listing Provided by: Lisa Rollins | Compass Connecticut, LLC
  • Source: SMART MLS-CT | MLS#: 24182948 SMART MLS-CT

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    New Haven County

  • City

    Cheshire

  • Neighborhood

    --

  • Year Built

    1955

  • HOA Fees

    -

  • Finished Area

    1,566 sqft

  • Lot Size

    18,295.2 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24182948

  • MLS Status

    Active

  • Days on Market

    144

Open House

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 2

Interior

  • Sewer

    Public Sewer Connected

  • Exterior Features

    Deck, Gutters, Garden Area

  • Cooling

    Window Unit

  • Interior Features

    Auto Garage Door Opener, Open Floor Plan

  • Appliances

    Electric Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Construction

  • Year Built

    Year Built: 1955

  • Home type

    Single Family Residence

  • Architectural Style

    Cape Cod

  • Foundation Details

    Concrete

  • Roof

    Asphalt Shingle

Utilities & Energy

  • Parking Features

    Detached Garage

  • Water Source

    Public Water Connected

  • Basement

    Full, Unfinished, Concrete Floor

Other Features

  • Subdivision Name

    N/a

  • Lot Features

    Level Lot

Price History

DateEventPrice

10/13/2026

Source: mls_logoSMART MLS-CT #24182948

Price Decreased

$465,000 -2.11%

$297/sqft

09/10/2026

Source: mls_logoSMART MLS-CT #24182948

Price Decreased

$475,000 -2.96%

$303/sqft

08/25/2026

Source: mls_logoSMART MLS-CT #24182948

Price Decreased

$489,500 -1.09%

$313/sqft

08/11/2026

Source: mls_logoSMART MLS-CT #24182948

Price Decreased

$494,900 -1.02%

$316/sqft

07/24/2026

Source: mls_logoSMART MLS-CT #24182948

Price Decreased

$500,000 -4.76%

$319/sqft

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Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Nov 07, 2026, 04:45AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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