106 Woodland Drive, Cheshire, CT 06410 - Photo 1

1/1

$365,000

Sold
Closed
Single Family
3 Beds
1 Full Bath
1 Partial Bath
1,516 Sq. Ft.
2 Car Garage

1/1

Property Description

Endless potential in this 3-bedroom, 1.5-bath ranch in Cheshire. Set on a quiet lot with a spacious deck, backyard, and two fireplaces, this home is ready for your updates and personal touch. The lower level offers excellent potential for an in-law suite or flexible living space. Major improvements have already been made, including a newer roof, oil tank, and furnace, providing a strong starting point. Conveniently located near Main Street, shopping, schools, and restaurants-this is an ideal opportunity for investors or buyers looking to create their dream home. Home is being sold AS IS.

Full Property Details

Full Property Details for 106 Woodland Dr

General

Sold For: $365,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24128648
Added to Site: 113 day(s) ago

Interior

Number of Rooms: 8
Interior Features: Cable - Available
Fireplace: Yes
Number of Fireplaces: 2
Appliances: Electric Cooktop, Oven/Range, Microwave, Refrigerator, Freezer, Washer, Dryer

Rooms

Bathrooms

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

Bedrooms

Total Bedrooms: 3
Primary Bedroom: Primary Bedroom, 13.6 x 13.7, Main
Bedroom 1: Bedroom, 12.3 x 14.1, Main
Bedroom 2: Bedroom, 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 - Sliders, Hardwood Floor, 12.2 x 13.7, Main
Laundry: Main Level

Exterior

Exterior Features: Deck, French Doors, Patio
Color: White

Parking

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

Location

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

School Information

Elementary School: Per Board of Ed
Middle School: Per Board of Ed
Intermediate School: Per Board of Ed
High School: Cheshire

Heating & Cooling

Cooling Type: Window Unit
Heating Type: Hot Water, Oil
Heating Fuel: Oil
Water Heater: Oil, 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, Partially Finished, Full With Walk-Out
Roof: Asphalt Shingle
Square Feet: 1,516
Above Ground: 1,516 Sq. Ft.
Year Built: 1959

Lot Features

Lot Size (Acres): 0.76
Driveway/Sidewalk: Private
Zoning: R-20
Lot Description: Lightly Wooded, 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 selling agent

— 106 Woodland Dr —

Felipe Segura

Email Me

(860) 305-4640 direct

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender

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 Pitney Bowes 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

10/16/2025

Sold

$365,000

4.32%

MLS

10/04/2025

Listed

$349,900

—

MLS

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

125 Salem Rd, Prospect, CT 06712 - Photo 1

Just Listed

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Single Family
Active
Updated 1 day ago

2
Beds
1
Total Bath
2,381
Sq. Ft.

Listed by Regency Real Estate, LLC

22 Salem Rd, Prospect, CT 06712 - Photo 1

Just Listed

$389,900

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Single Family
Active
Updated 2 days ago

2
Beds
2
Total Baths
1,390
Sq. Ft.

Listed by Century 21 Bette Real Estate

7 Sunbright Dr S, Meriden, CT 06450 - Photo 1

Just Listed

$374,900

Open House

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Single Family
Active
Updated 1 day ago

3
Beds
2
Total Baths
1,280
Sq. Ft.

Listed by Lindsay Lionetti (203) 843-7363

54 Parker Farms Rd, Wallingford, CT 06492 - Photo 1

Just Listed

$249,900

54 Parker Farms Rd Wallingford, CT 06492

Single Family
Active
Updated 5 days ago

2
Beds
1
Total Bath
1,070
Sq. Ft.

Listed by Paul Pender (203) 213-1651

60 Capitol Ave, Meriden, CT 06451 - Photo 1

Price Reduced

-$7,000 (-2.29%)

$299,000

60 Capitol Ave Meriden, CT 06451

Single Family
Active
Updated 3 days ago

4
Beds
2
Total Baths
1,850
Sq. Ft.

Listed by Creative Realty of CT LLC

198 Mildred Rd, Meriden, CT 06450 - Photo 1

Price Reduced

-$25,000 (-6.67%)

$350,000

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Single Family
Active
Updated 3 days ago

4
Beds
2
Total Baths
1,312
Sq. Ft.

Listed by JV Real Estate & Insurance Co.

230 W Main St, Meriden, CT 06451 - Photo 1

Price Reduced

-$5,000 (-0.69%)

$720,000

230 W Main St Meriden, CT 06451

Multi-Family
Active
Updated 2 days ago

10
Total Beds

Listed by Kazantzis Real Estate, LLC

10 Pilgrim Harbor, Wallingford, CT 06492 - Photo 1

Price Reduced

-$6,000 (-1.97%)

$299,000

10 Pilgrim Harbor #C Wallingford, CT 06492

Condo
Active
Updated 4 days ago

2
Beds
2
Total Baths
1,038
Sq. Ft.

Listed by William Raveis Real Estate

68 Woodland Dr, Cheshire, CT 06410 - Photo 1

Sold

$382,000

68 Woodland Dr Cheshire, CT 06410

Single Family
Closed

4
Beds
2
Total Baths
2,227
Sq. Ft.

Listed by New England Realty Assoc LLC
Sold by Reddy Realty, LLC

90 Cedar Ln, Cheshire, CT 06410 - Photo 1

Sold

$370,000

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Single Family
Closed

2
Beds
1
Total Bath
1,055
Sq. Ft.

Listed by William Raveis Real Estate
Sold by Bottom Line Realty

148 Fairway Dr, Cheshire, CT 06410 - Photo 1

Sold

$315,000

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Townhouse
Closed

2
Beds
2
Total Baths
1,052
Sq. Ft.

Listed by Amy Lapierre
Sold by Tier 1 Real Estate

125 Curve Hill Rd, Cheshire, CT 06410 - Photo 1

Sold

$405,000

125 Curve Hill Rd Cheshire, CT 06410

Single Family
Closed

3
Beds
2
Total Baths
1,282
Sq. Ft.

Listed by Calcagni Real Estate
Sold by William Raveis Real Estate

106 Woodland Drive, Cheshire, CT 06410 (MLS# 24128648) is a Single Family property that was sold at $365,000 on October 16, 2025. This property was sold 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