14 Upland Rd, Winsted, CT 06098
Bedroom
Kichen
OFF MARKET
  • 3 Beds
  • 1 Bath
  • 1,000 sqft

14 Upland Rd, Winsted, CT 06098

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
35 Riveredge Dr, Winsted, CT
0.91
Apartment
$151,000
06/11/26
2
2
992
134 Maple St, Winsted, CT
0.92
Apartment
$300,000
05/13/26
3
1.5
1,700
Home facts updated by county records

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
18 Upland Road, Winsted, CT 06098
0.02
$313,300
5
2
2,338
Off Market
61 Spencer Street, Winsted, CT 06098
0.03
$366,700
Studio
3
2,550
Off Market
30 Upland Road, Winsted, CT 06098
0.05
$185,000
4
2
1,844
Recently Sold
3 Brookside Avenue, Winsted, CT 06098
0.08
$277,600
Studio
-
2,421
Off Market
830 Main Street, Winsted, CT 06098
0.07
$237,600
10
3
3,115
Off Market
38 Upland Road, Winsted, CT 06098
0.07
$240,000
3
1.5
1,736
Recently Sold
44 Spencer Street, Winsted, CT 06098
0.09
$368,700
3
1.5
2,008
Off Market
42 Upland Road, Winsted, CT 06098
0.08
$247,900
2
1
1,236
Off Market
17 Front Street, Winsted, CT 06098
0.15
$242,100
4
1.5
1,600
Off Market
118 Meadow Street, Winsted, CT 06098
0.16
$260,000
3
2
1,652
For Sale
98 Meadow Street, Winsted, CT 06098
0.16
$301,800
4
2
2,006
Off Market
141 Spencer Street, Winsted, CT 06098
0.17
$305,500
4
1
1,540
Off Market

Local Information

  • Map ViewExplore the area around 14 Upland Rd.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Apartment
Built in 1900
1,000 sqft

About this House

Quiet neighborhood. ... no traffic street... duplex unit ... multiple levels. .. washer and dryer included

Owner pays trash,sewer and water .... tenant pays rent ,electric and gas .... must have references
14 Upland Rd, Winsted, CT 06098 is a 3 bedroom, 1 bathroom, 1,000 sqft apartment built in 1900. More recently, it was listed as a rental in October 2017 with an asking price of $850 per month. That rental listing was removed on March 24, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $1,534/month.

Home Details for 14 Upland Rd

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Interior Details
Number of Rooms: 6Types of Rooms: Dining Room
Appliances & Utilities
Cable ReadyRefrigeratorWasher
Windows, Doors, Floors & Walls
Double Paned Windows
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: ApartmentArchitecture: Other

Exterior Features

Exterior Home Features
Lawn
Parking & Garage
Parking: On Street

Price and Tax history

DateEventPrice
Mar 24, 2021
Source: N/A
ListingRemoved
Nov 16, 2017
Source: N/A
ListingRemoved
$850
Oct 21, 2017
Source: N/A
Listed For Rent
$850
May 11, 2014
Source: Agent Provided
ListingRemoved
$825
May 1, 2014
Source: Agent Provided
Listed For Rent
$825

Market trends in Winsted

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
15
3MoM

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

Frequently asked questions about 14 Upland Rd

  • Is Winsted a buyer's or seller's market?
    Winsted is currently a seller's 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 14 Upland Rd?
    The closest schools to 14 Upland Rd in Winsted, CT are Mary P. Hinsdale School (Pre-K/Elementary), Pearson Middle School (Elementary, rated 6/10).
  • Does 14 Upland Rd have parking?
    Yes, 14 Upland Rd in Winsted, CT has on-site parking.

Explore by feature - Pet Friendly

11 pet-friendly rentals in Winsted, CT

Explore by feature - Washer/dryer

9 rentals with a washer/dryer in Winsted, CT

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 14 Upland Rd

Skip to last item
Skip to first item

Homes for sale near 14 Upland Rd

Skip to last item
  • Results are loading
Skip to first item
Skip to last item
  • Results are loading
Skip to first item