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$550,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,566 Sq. Ft.
  • 2 Car Garage
  • Updated 2 days ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 6/20 11:00 AM - 1:00 PM

16 Deepwood Drive,Cheshire, CT 06410

16 Deepwood DriveCheshireCT06410

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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!

Full Property Details for 16 Deepwood Dr

General

  • Price: $550,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24182948
  • Updated: 6/17/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 6
  • Interior Features: Auto Garage Door Opener, Open Floor Plan
  • Appliances: Electric Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Full Bath: Remodeled, Stall Shower, Main

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Hardwood Floor, Main
  • Bedroom 1: Bedroom - Hardwood Floor, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Hardwood Floor, Main
  • Kitchen: Kitchen - Remodeled, Balcony/Deck, Breakfast Bar, Quartz Counters, Main
  • Dining Room: Dining Room - Remodeled, Built-Ins, Main

Exterior

  • Exterior Features: Deck, Gutters, Garden Area

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking: Detached Garage

Location

  • County: New Haven
  • Driving Directions: Route 68 West Main St to Deepwood Drive - First House on Right

School Information

  • Elementary School: Per Board of Ed
  • High School: Cheshire

Heating & Cooling

  • Cooling Type: Window Unit
  • Heating Type: Hot Air, Gas In Street
  • Heating Fuel: Gas In Street
  • Water Heater: Natural Gas, 40 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Cape Cod
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding, Vertical Siding
  • Basement Desc.: Full, Unfinished, Concrete Floor
  • Roof: Asphalt Shingle
  • Square Feet: 1,566
  • Above Ground: 1,566 Sq. Ft.
  • Year Built: 1955

Lot Features

  • Lot Size (Acres): 0.42
  • Zoning: R-20
  • Lot Description: Level Lot

Green Features

  • Energy Features: Thermopane Windows

Financial Considerations

  • Assessment Amount: $192,080
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 2339301

Listed by Compass Connecticut, LLC, Lisa Rollins Team, Lisa Rollins and Compass Connecticut, LLC, Lisa Rollins Team, Lisa Szyndlar

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Listing agents

— 16 Deepwood Dr —

  • Lisa Rollins

    Compass Connecticut, LLC

  • Lisa Szyndlar

    Compass Connecticut, LLC

Agent Contact: (203) 671-0295 Office Contact: (203) 245-1593

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 16 Deepwood Dr

School District:Cheshire School District
NameGradesDistance
Highland School, Cheshire, CT
490 Highland Avenue, Cheshire, CT 06410
1-60.9 mi
Dodd Middle School
100 Park Place, Cheshire, CT 06410
7-80.5 mi
Cheshire High School
525 South Main Street, Cheshire, CT 06410
9-121.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 16 Deepwood Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/17/2026
Listed
$550,000
107.55%
MLS
2/06/2026
Sold
$265,001
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 16 Deepwood Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,712
8%
$192,080
—
2023
$5,275
18%
$192,080
51%
2023
$4,466
2%
$127,280
—
2022
$4,368
2%
$127,280
—
2021
$4,292
2%
$127,280
—
2020
$4,228
—
$127,280
—
2019
$4,228
-1%
$127,280
-3%
2018
$4,291
2%
$131,560
—
2017
$4,202
2%
$131,560
—
2016
$4,103
2%
$131,560
—
2015
$4,038
1%
$131,560
—
2014
$3,980
—
$131,560
-9%
2011
$3,981
—
$144,240
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 16 Deepwood Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Compass Connecticut, LLC, Lisa Rollins Team, Lisa Rollins and Compass Connecticut, LLC, Lisa Rollins Team, Lisa Szyndlar

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16 Deepwood Drive, Cheshire, CT 06410 (MLS# 24182948) is a Single Family property with 3 bedrooms and 2 full bathrooms. 16 Deepwood Drive is currently listed for $550,000 and was received on June 17, 2026. Want to learn more about 16 Deepwood Drive? Do you have questions about finding other Single Family real estate for sale in Cheshire? You can browse all Cheshire real estate or contact a Coldwell Banker agent to request more information.

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