106 Woodland Drive, Cheshire, CT 06410 - Photo 1

1/1

$605,000

Sold
Closed
Single Family
3 Beds
2 Full Baths
2,247 Sq. Ft.
2 Car Garage

1/1

Property Description

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 show stopping, 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. Major upgrades provide peace of mind, including central air (2026), 200-amp electrical service (2026), and newer roof and windows. These significant improvements deliver efficiency and long term value. 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

Full Property Details

Full Property Details for 106 Woodland Dr

General

Sold For: $605,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24157835
Added to Site: 55 day(s) ago

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: 2

Bedrooms

Total Bedrooms: 3
Primary Bedroom: Primary Bedroom - Hardwood Floor, 12.9 x 13.7, Main
Bedroom 1: Bedroom - Hardwood Floor, 11.9 x 13.2, Main
Bedroom 2: Bedroom - Hardwood Floor, 9.1 x 13.2, Main

Other Rooms

Living Room: Living Room - Fireplace, Hardwood Floor, 24.5 x 13.2, Main
Dining Room: Dining Room - Balcony/Deck, Sliders, Hardwood Floor, 11.11 x 13.8, 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

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Meet the listing and selling agents

— 106 Woodland Dr —

Felipe Segura

Email Me

(860) 305-4640 direct
Odalys Bekanich

Email Me

(860) 965-3652 direct
Right Move Team

Email Us

(203) 974-3531 direct

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NMLS#: 1598647

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Schools

Schools serving 106 Woodland Dr

School District:Cheshire School District

Name	Grades	Distance
Chapman School 38 Country Club Road, Cheshire, CT 06410	1-6	0.2 mi
Dodd Middle School 100 Park Place, Cheshire, CT 06410	7-8	0.8 mi
Cheshire High School 525 South Main Street, Cheshire, CT 06410	9-12	2.1 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 106 Woodland Dr

Date

Details

Price

Change

Source

4/01/2026

Sold

$605,000

3.44%

MLS

3/07/2026

Listed

$584,900

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Updated 2 days ago

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Beds
3
Total Baths
2,314
Sq. Ft.

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Just Listed

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Updated 8 hours ago

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3
Total Baths
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Just Listed

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Total Baths
1,586
Sq. Ft.

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Just Listed

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Condo
Active
Updated 3 days ago

2
Beds
1
Total Bath
1,034
Sq. Ft.

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Price Reduced

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Land Residential
Active
Updated 22 hours ago

2.18
Acres

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Price Reduced

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$650,000

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Updated 4 days ago

4
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2
Total Baths
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Price Reduced

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$475,000

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Active
Updated 3 hours ago

4
Beds
3
Total Baths
2,042
Sq. Ft.

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Price Reduced

-$20,000 (-4%)

$479,900

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Multi-Family
Active
Updated 4 days ago

6
Total Beds

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$530,000

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Single Family
Closed

3
Beds
3
Total Baths
2,085
Sq. Ft.

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Sold by Kary Apanovitch

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Sold

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Single Family
Closed

3
Beds
3
Total Baths
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$585,000

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Single Family
Closed
Updated 7 days ago

2
Beds
2
Total Baths
1,810
Sq. Ft.

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Sold

$620,000

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Condo
Closed

3
Beds
3
Total Baths
2,637
Sq. Ft.

Listed by Press/Cuozzo Realtors
Sold by William Pitt Sotheby's Int'l

106 Woodland Drive, Cheshire, CT 06410 (MLS# 24157835) is a Single Family property that was sold at $605,000 on April 01, 2026. This property was 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.

106 Woodland Dr Cheshire, CT 06410