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$584,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • 2,247 Sq. Ft.
  • 2 Car Garage
  • Updated 5 hours ago
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Welcome to 106 Woodland Drive in highly sought-after Cheshire!! This stunning, fully renovated home has been beautifully reimagined from to top to bottom, offering modern style, comfort and functionality throughout. Featuring 3 bedrooms and 2 full bathrooms, this home is the definition of true move in ready living. Step inside to discover a showstopping, brand-new kitchen designed to impress, featuring sleek modern finishes, stylish custom cabinetry, and contemporary design that makes both everyday living and entertaining effortless. The completely renovated bathrooms showcase elegant finishes and a fresh, modern feel. The home continues to impress with a fully finished basement with electric heat and an additional bedroom and a cozy fireplace, providing the perfect space for guests, a private home office, in-law potential, or a recreation area-adding valuable extra living space. Central air ensures year-round comfort, while the renovations make everyday living effortless. Located in a quiet neighborhood yet close to shopping, dining, and major commuter routes, this home offers the ideal combination of space, updates, and convenience. Don't miss your opportunity to own this turnkey Cheshire home-schedule your private showing today! Professional photos will be uploaded soon!

Full Property Details for 106 Woodland Dr

General

  • Price: $584,900
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24157835
  • Updated: Today (3/7/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 8
  • Interior Features: Cable - Available
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Electric Range, Microwave, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 1
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Hardwood Floor, 13.6 x 13.7, Main
  • Bedroom 1: Bedroom - Hardwood Floor, 12.3 x 14.1, Main
  • Bedroom 2: Bedroom - Hardwood Floor, 8.11 x 14.1, Main

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, 24.8 x 14.1, Main
  • Dining Room: Dining Room - Balcony/Deck, Sliders, Hardwood Floor, 12.2 x 13.7, Main
  • Laundry: Main Level

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking: Attached Garage, Driveway

Location

  • County: New Haven
  • Driving Directions: GPS friendly- Whitney Avenue to Highland Ave to Country Club Rd to Woodland Drive

School Information

  • Elementary School: Chapman
  • Middle School: Dodd
  • High School: Cheshire

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Baseboard, Hot Water, Electric, Oil
  • Heating Fuel: Electric, Oil
  • Water Heater: Other, Oil, Electric, Tankless Hotwater

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Ranch
  • Construction Status: No/Resale
  • Exterior Const.: Shingle, Wood
  • Basement Desc.: Full, Heated, Fully Finished, Liveable Space, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,247
  • Above Ground: 1,516 Sq. Ft.
  • Below Ground: 731 Sq. Ft.
  • Year Built: 1959

Lot Features

  • Lot Size (Acres): 0.76
  • Driveway/Sidewalk: Private
  • Zoning: R-20
  • Lot Description: Level Lot, Sloping Lot

Financial Considerations

  • Assessment Amount: $242,130
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 2339047
Buyer's Brokerage Compensation: Contact Listing Agent
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— 106 Woodland Dr —

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NMLS#: 1598647

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NMLS#: 1598647

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Price & Sales History for 106 Woodland Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/07/2026
Listed
$584,900
60.25%
MLS
10/15/2025
Sold
$365,000
—
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 106 Woodland Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,201
8%
$242,130
—
2023
$6,649
6%
$242,130
36%
2023
$6,247
2%
$178,020
—
2022
$6,110
2%
$178,020
—
2021
$6,003
2%
$178,020
—
2020
$5,914
—
$178,020
—
2019
$5,914
1%
$178,020
—
2018
$5,830
2%
$178,730
—
2017
$5,709
2%
$178,730
—
2016
$5,575
2%
$178,730
—
2015
$5,485
1%
$178,730
—
2014
$5,407
-1%
$178,730
-9%
2011
$5,445
—
$197,270
—
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.

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106 Woodland Drive, Cheshire, CT 06410 (MLS# 24157835) is a Single Family property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 106 Woodland Drive is currently listed for $584,900 and was received on March 07, 2026. This property is listed by Felipe Segura from our Avon / Farmington Office.Want to learn more about 106 Woodland 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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