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$269,000 Contingent

  • For Sale
  • Contingent
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • 1,736 Sq. Ft.
  • 1 Car Garage
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TO SETTLE ESTATE: Available for Immediate Occupancy is this Immaculate 3 to 4 Bedroom Colonial tucked away on a quiet street. Features Hardwood Floors throughout the house, 24' x 14' Family Room with Propane Gas Stove, Country Kitchen. Primary Bedroom with it's own office area. Oversized Full Bath. 3-Season 21' x 8' Enclosed Porch. 26' x 10' Concrete Patio. Detached One Car Garage. Attractive Park-Like Landscaped Grounds. Off Street Parking for 6 Vehicles. City Water and Sewer. All Kitchen Appliance as well as Washer & Dryer remain with the property. Close Proximity to Town Center for General Shopping, Medical, Variety of Food Venues. "MOVE-IN CONDITION".

Full Property Details for 38 Upland Rd

General

  • Price: $269,000
  • Taxes: (July 2025-June 2026)
  • Status: Contingent
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24131432
  • Updated: 12/30/2025
  • Added to Site: 104 day(s) ago

Interior

  • Number of Rooms: 7
  • Rooms/Areas: Laundry Room, Mud Room
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 1
  • Half Bathrooms: 1
  • Full Bath: Tile Floor, Upper
  • Partial Bath: Main

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Ceiling Fan, Hardwood Floor, 11.25 x 14, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, 12 x 10.75, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, 12 x 9.6, Upper

Other Rooms

  • Living Room: Living Room - Bay/Bow Window, Wall/Wall Carpet, 17 x 12, Main
  • Family Room: Family Room - Wall/Wall Carpet, 24 x 14, Main
  • Eat In Kitchen: Eat-In Kitchen - Vinyl Floor, 22 x 16.3, Main
  • Dining Room: Dining Room - Wall/Wall Carpet, 14 x 12, Main
  • Office: Office, 11.6 x 5.5, Upper
  • Laundry: Main Level

Exterior

  • Exterior Features: Porch-Enclosed, Porch, Gutters, Lighting
  • Color: White

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Total Spaces: 6
  • Parking: Detached Garage, Off Street Parking

Location

  • County: Litchfield
  • Neighborhood: Winsted
  • Driving Directions: Main Street to Spencer Street. Left on Upland Road. Address #38 is on the Right. GPS Friendly.

School Information

  • Elementary School: Harry P. Hinsdale
  • Middle School: Pearson
  • High School: Gilbert

Community

  • Community Name: Winsted

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Radiator, Oil
  • Heating Fuel: Oil
  • Water Heater: Electric, 40 Gallon Tank

Utilities

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

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Unfinished, Sump Pump, Storage, Interior Access, Concrete Floor, Full With Hatchway
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Disability Access: Chair Lift
  • Square Feet: 1,736
  • Above Ground: 1,736 Sq. Ft.
  • Year Built: 1870

Lot Features

  • Lot Size (Acres): 0.34
  • Zoning: TG
  • Lot Description: Level Lot, Professionally Landscaped

Green Features

  • Energy Features: Storm Doors

Financial Considerations

  • Assessment Amount: $136,220
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 926816

Listed by Cohen Agency, Marshall Cohen and Cohen Agency, Holly Blinkoff

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Listing agents

— 38 Upland Rd —

  • Marshall Cohen

    Cohen Agency

  • Holly Blinkoff

    Cohen Agency

Agent Contact: (860) 307-2594 Office Contact: (860) 618-5800

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 38 Upland Rd

School District:Winchester School District
NameGradesDistance
Pearson Middle School
2 Wetmore Avenue, Winsted, CT 06098
3-60.6 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 38 Upland Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/28/2025
Price Reduced
$269,000
-5.28%
MLS
10/04/2025
Listed
$284,000
—
MLS
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 38 Upland Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$3,974
7%
$136,220
—
2023
$3,711
3%
$136,220
—
2023
$3,595
9%
$136,220
39%
2022
$3,294
—
$98,210
—
2021
$3,294
—
$98,210
—
2020
$3,294
—
$98,210
—
2019
$3,294
—
$98,210
—
2018
$3,294
5%
$98,210
5%
2017
$3,125
—
$93,170
—
2016
$3,125
3%
$93,170
—
2015
$3,047
2%
$93,170
—
2014
$2,973
2%
$93,170
—
2011
$2,907
—
$93,170
—
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 38 Upland Rd

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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 Cohen Agency, Marshall Cohen and Cohen Agency, Holly Blinkoff

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38 Upland Road, Winchester, CT 06098 (MLS# 24131432) is a Single Family property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 38 Upland Road is currently listed for $269,000 and was received on October 04, 2025. Want to learn more about 38 Upland Road? Do you have questions about finding other Single Family real estate for sale in Winsted? You can browse all Winsted real estate or contact a Coldwell Banker agent to request more information.

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