38 Upland Road, Winsted, CT 06098
SOLD
MAR 11, 2026

$240,000

Last sold price
  • 3 Beds
  • 1.5 Baths
  • 1,736 sqft (on 0.34 acres)

38 Upland Road, Winsted, CT 06098

Est. Refi. Payment $1,676/mo*
Refinance Your Home
Currently Off Market - Sold Mar 11, 2026 for $240,000 (11% below list price)

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
30 Upland Road, Winsted, CT
0.02
Single-Family Home
$185,000
07/22/26
4
2
1,844
15 John Street, Winsted, CT
0.17
Single-Family Home
$288,557
10/29/25
3
2
1,538
22 Curtice Street, Winsted, CT
0.32
Single-Family Home
$243,000
11/17/25
3
1
1,334
9 John Street, Winsted, CT
0.16
Single-Family Home
$225,000
04/02/26
2
1.5
1,172
17 Adams Street, Winsted, CT
0.61
Single-Family Home
$315,000
09/29/25
3
1.5
1,747
18 Curtice Street, Winsted, CT
0.31
Single-Family Home
$229,000
02/09/26
2
1.5
1,252

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
30 Upland Road, Winsted, CT 06098
0.02
$185,000
4
2
1,844
Recently Sold
18 Upland Road, Winsted, CT 06098
0.05
$312,300
5
2
2,338
Off Market
830 Main Street, Winsted, CT 06098
0.06
$236,800
10
3
3,115
Off Market
42 Upland Road, Winsted, CT 06098
0.02
$246,600
2
1
1,236
Off Market
61 Spencer Street, Winsted, CT 06098
0.10
$334,300
Studio
3
2,550
Off Market
3 Brookside Avenue, Winsted, CT 06098
0.15
$280,700
Studio
-
2,421
Off Market
44 Spencer Street, Winsted, CT 06098
0.15
$367,300
3
1.5
2,008
Off Market
118 Meadow Street, Winsted, CT 06098
0.10
$259,000
3
2
1,652
For Sale
17 Front Street, Winsted, CT 06098
0.13
$242,500
4
1.5
1,600
Off Market
98 Meadow Street, Winsted, CT 06098
0.12
$297,900
4
2
2,006
Off Market
150 Meadow Street, Winsted, CT 06098
0.11
$273,200
4
2
2,094
Off Market

Local Information

  • Map ViewExplore the area around 38 Upland Road.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1870
0.34 acre lot
1,736 sqft
$138/sqft
Garage

About this House

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".
38 Upland Road, Winsted, CT 06098 is a 3 bedroom, 2 bathroom, 1,736 sqft single-family home built in 1870. It last sold for $240,000 on Mar 11, 2026 (11% below the $269,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $2,455/month.
Last check for updates: about 22 hours ago
Listed by Marshall Cohen, (860) 307-2594
Cohen Agency, (860) 618-5800
Holly Blinkoff, (860) 806-8010
Cohen Agency, (860) 618-5800
Bought with: Sharon Gilson, (860) 485-8844, Northwest CT Realty, (860) 379-7245
Source: Smart MLS, MLS#24131432

Home Details for 38 Upland Road

Interior Features

Interior Details
Basement: Full,Unfinished,Sump Pump,Storage Space,Interior Entry,ConcreteNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1736 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Electric Water Heater, Water HeaterDishwasherDryerLaundry: Main Level,Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Radiator,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Radiator
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Door: Storm Door(s)
Levels, Entrance, & Accessibility
Accessibility: Stair Lift

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Enclosed, PorchExterior: Rain Gutters, LightingFoundation: StoneNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageNo Attached GarageParking Spaces: 6Parking: Detached,Off Street,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1736 Square Feet

Property Information

Year Built
Year Built: 1870
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 926816

Price & Status

Price
List Price: $269,000Price Per Sqft: $138/sqft
Status Change & Dates
Off Market Date: Tue Dec 30 2025Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: WinchesterCommunity: Winsted
School Information
Elementary School: Harry P. HinsdaleJr High / Middle School: PearsonHigh School: Gilbert

Building

Building Area
Building Area: 1736 Square Feet

Community

Community Features: Golf, Lake, Library, Medical Facilities, Park, Playground, Shopping/Mall, Tennis Court(s)
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.34 acres

Energy

Energy Efficiency Features: Doors

Miscellaneous

BasementMls Number: 24131432Attic: Pull Down StairsAttribution Contact: (860) 307-2594Above Grade Unfinished Area: 1736

Additional Information

GolfLakeLibraryMedical FacilitiesParkPlaygroundShopping/MallTennis Court(s)

Price and Tax history

DateEventPrice
Mar 11, 2026
Source: Smart MLS #24131432
Sold
$240,000
Mar 10, 2026
Source: Smart MLS #24131432
Pending
$269,000
Oct 28, 2025
Source: Smart MLS #24131432
PriceChange
$269,000
Price decreased by 5%
Oct 6, 2025
Source: Smart MLS #24131432
Listed For Sale
$284,000
Oct 3, 2025
Source: Smart MLS #24103381
ListingRemoved
$299,000

Market trends in Winsted

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
12
2MoM

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winsted

At least 82 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 85 % Say there's wildlife

  • 82 % Say it's dog friendly

  • 67 % Say it's walkable to restaurants

  • 67 % Say there's holiday spirit

  • 67 % Say yards are well-kept

  • 67 % Say parking is easy

  • 62 % Say streets are well-lit

  • 59 % Say kids play outside

  • 58 % Say there are sidewalks

  • 57 % Say neighbors are friendly

  • 52 % Say people would walk alone at night

  • 44 % Say it's quiet

  • 39 % Say they plan to stay for at least 5 years

  • 30 % Say it's walkable to grocery stores

  • 18 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Amber Matarainen
    "Takes forever to get anywhere worthy of being. Traffic gets backed up midday, and people speed through lights all the time"
    0
    Flag
  • Linda Kaiser
    "Small town feel with all of the required amenities. People are friendly and there are several excellent eateries. "
    0
    Flag
  • Nick W.
    " great schools nice tonw friendly people and streets are fimmaly getting repaved though some aren't even tho they need it Really badly "
    2
    Flag
  • Tammy W.
    "I really like it here just really wish that we had a grocery store in walking distance. There is only one in this town and if you don’t have a car you can not get to it."
    0
    Flag
  • Tammy W.
    "It’s not a bad place to live. Most of the people are nice and it is a clean place. I am just looking for a place with a bigger yard and closer to grocery stores. That is the biggest problem with this town. If you don’t have a car it is very hard to live here. If they could fix that problem I would not be looking to move out of town."
    0
    Flag
  • Tammy W.
    "People are always walking their dogs around my neighborhood. Just have to remind a few of them that they need to clean up after their dogs and not leave it there. But it is nice to see that family’s still walk around and enjoy themselves."
    2
    Flag
  • Tammy W.
    "This is a nice place to raise your kids. And it is a very safe place as well. I have lived here my whole life."
    5
    Flag
  • Tammy W.
    "Great. The driver was very nice and helpful when needed. It is not expensive to ride the bus. I would recommend public transit to everybody that needs it. The drivers are very nice about stopping close to your designation."
    1
    Flag
  • Trulia User
    "My neighborhood is close to downtown, close to the Main Street and easily accessible for the public transportation "
    0
    Flag
  • Nick W.
    "I think most of the surrounding areas within Winsted are Gradually getting better, Great schools, Awsome neighbors(Most) small town feel is good for me."
    0
    Flag
  • Shanura G.
    "I've lived here for over 25 yrs and love...very great neighborhood and friendly people...school system is great"
    0
    Flag
  • Ericka A.
    "watch out for walkways they need work and the best parks for kids is the baseball/memorial park and peirson elementary park there enclosed "
    0
    Flag
  • Jennifer M.
    "Winsted is a small working class town. the schools are improving and you g families should definitely consider moving here. "
    0
    Flag
  • Bruinssox1
    "No dog parks to bring your dog too. The parks we do have are no dogs allowed.There is a lot of traffic to watch out for"
    0
    Flag
  • Kaeabalan
    "There are a million dogs on my street and the surrounding streets. I see people out walking dogs frequently, day and night. On the occasion my dog gets loose, the neighbors are a great help in bringing him home. "
    2
    Flag
  • Eric R.
    "Great access to parks and public activities. Close to local community college, private neighbors, easy access to local hospitals."
    1
    Flag
  • Choiniere j.
    "Been here almost a year, and its what you make of it. Could be better her and there, but its a nice town for your family. Not too much in the cost of living, which is a plus!"
    6
    Flag
  • liz
    "Nice and quiet area where neighbors look out for each other's property."
    1
    Flag

LGBTQ Local Legal Protections

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Frequently asked questions about 38 Upland Road

  • What is the price history for 38 Upland Road?
    38 Upland Road in Winsted, CT last sold for $240,000 in March 2026.
  • Is Winsted a buyer's or seller's market?
    Winsted is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Winsted?
    Residents describe Winsted, CT as dog-friendly, walkable to restaurants, and well-kept. See recently sold homes in Winsted, CT.
  • What are the closest schools to 38 Upland Road?
    The closest schools to 38 Upland Road in Winsted, CT are Mary P. Hinsdale School (Pre-K/Elementary), Pearson Middle School (Elementary, rated 6/10).
  • Does 38 Upland Road have laundry facilities?
    Yes, 38 Upland Road in Winsted, CT has in-unit laundry.
  • How big is the lot at 38 Upland Road?
    The lot at 38 Upland Road in Winsted, CT is about 0.34 acres (14,810 sq ft).

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