Sold on Jul 2026

$185,000

•

1,844

sq ft

30 Upland Rd, Winsted, CT 06098

Track this home’s value and nearby sales activity

About this home

Located in the charming community of Winsted, this 4-bedroom home is tucked away in a quiet, low-traffic neighborhood while still being close to many local amenities. Hardwood floors run throughout the home, adding warmth and character, and the tree-lined backyard offers a private outdoor setting to enjoy year round. This home also features a beautiful enclosed second-floor sun porch, perfect for relaxing with morning coffee, reading, or enjoying the changing seasons. A large walk-up attic provides abundant storage space and may offer the potential to be finished for additional living area, office space, or a hobby room. Just a short distance away, you will find the local library, coffee shops, parks, restaurants, and a variety of neighborhood shops and conveniences. Outdoor enthusiasts will appreciate nearby Highland Lake, offering opportunities for boating, swimming, and recreation throughout the warmer months. This home does need some TLC and updating, but with vision and effort, it has the potential to truly shine. Whether you are looking for a primary residence or an investment opportunity, this property offers excellent potential in a desirable location. **Audio & Video surveillance present**

Single-familyProperty Type

1869Year Built

7,405 sq ftLot Size

$100Price/Sq.Ft.

1 spaceParking

Listed by Jeffrey Liskin • Northwest CT Realty

Listed by David Sartirana • Northwest CT Realty

Contact: Agent Attribution Contact: (860) 601-0991 | Office Attribution Contact: (860) 379-7245

Bought with Gabriela Pesantez • William Raveis Real Estate

Source:Smart MLS #24176921

Redfin Estimate

$197,350

$12K since sold in July 2026$18K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 49.6% lower than the average sale price ($392K) of 6 comparable homes.

SOLD JUL 2, 2026
$210,000
A
4 beds2 baths1,874 sq ft
107 Birdsall St, Winsted, CT 06098
SOLD JUN 16, 2026
$368,500
B
3 beds2 baths1,898 sq ft
102 Wallens St, Winsted, CT 06098
SOLD MAY 27, 2026
$276,000
C
4 beds1.5 baths1,416 sq ft
57 Bridge St, Winsted, CT 06098
SOLD FEB 27, 2026
$330,000
D
4 beds2 baths2,345 sq ft
123 Wetmore Ave, Winsted, CT 06098
SOLD JUN 4, 2026
$925,000
E
4 beds2 baths1,373 sq ft
258 Perch Rock Trl, Winsted, CT 06098
SOLD MAR 11, 2026
$240,000
F
3 beds1.5 baths1,736 sq ft
38 Upland Rd, Winsted, CT 06098

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Market trends in 06098, CT

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

103.0%

+4.2% MoM

Median sale price

$325K

$9K MoM

Avg. days on market

43d

1 days MoM

Recently sold homes

12 MoM

New listings for sale

$275,000
2 beds1 bath912 sq ft
1 Division St, Winsted, CT 06098
OPEN TODAY, 1PM TO 3PM
$319,900
2 beds2 baths1,192 sq ft
325 E Wakefield Blvd, Winsted, CT 06098
$325,000
4 beds2.5 baths2,257 sq ft
48 Center St, Winsted, CT 06098
$629,900
3 beds1.5 baths1,168 sq ft
837 E Wakefield Blvd, Winsted, CT 06098
COMING SOON
$309,900
2 beds2 baths1,346 sq ft
94 Colony Dr, Winsted, CT 06098
$600,000
4 beds2.5 baths3,486 sq ft
205 Wallens St, Winsted, CT 06098
OPEN TODAY, 1:30PM TO 3:30PM
$799,900
2 beds1 bath1,044 sq ft
804 W Wakefield Blvd, Winsted, CT 06098
See all

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Rental estimate

Est. $2,602 per month, based on comparable rentals

Sale and tax history for 30 Upland Rd

Sale History
Tax History

Date

Event

Price

Smart MLS #24176921

Jul 22, 2026

Sold

$185,000

$100/sq ft

Jul 6, 2026

Pending

—

Jun 5, 2026

Relisted

—

May 29, 2026

Contingent

—

May 19, 2026

Listed

$220,000

$119/sq ft

Smart MLS #170090607

Sep 28, 2018

Sold

$110,000

$60/sq ft

Aug 4, 2018

Contingent

—

Jun 1, 2018

Listed

$115,000

$62/sq ft

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

7,405 Sq. Ft.

Year renovated

—

Sq. Ft.

1,844

Year built

1869

Style

Single Family Residential

County

Litchfield County

APN

926817

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on May 25, 2023.

Property details

Parking

Garage Information
Garage & Parking: Driveway

Parking Information
Parking Total Spaces: 1

Interior

Interior Information
Total Rooms: 8
Laundry Room Location: Hallway
Laundry Room Info: Main Level
In-Law Apartment: No
Appliances Included: Oven/Range, Refrigerator, Washer, Dryer

Bathroom Information
# of Baths (Full): 2

Bedroom Information
Beds Total: 4

Room Information
Rooms Additional: Bonus Room
Basement Description: Full, Unfinished
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Metal
Exterior Siding: Vinyl Siding
Exterior Features: Porch

Lot Information
Lot Description: Level Lot, Sloping Lot

Building Information
Foundation Type: Stone
Construction Description: Frame
Color: White

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 1844
Driveway Type: Paved

Financial

Assessments Information
Assessed Value: $109,830

Utilities

Utility Information
Water Source: Public Water Connected
Sewer Usage Fee Annual: $600
Sewer Assess Description: Metered
Sewage System: Public Sewer Connected
Hot Water Description: Electric, 40 Gallon Tank
Heat Type: Hot Air
Heat Fuel Type: Oil
Fuel Tank Location: In Basement

Location

School Information
High School: Per Board of Ed
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Nearby Amenities: Health Club, Lake, Library, Medical Facilities, Park, Public Rec Facilities
Directions: Route 44 Main Street to Upland Rd
County: Litchfield

Public facts

Beds: 4
Baths: 2.0
Sq. Ft.: 1,844
Stories: 2.0
Lot Size: 7,405 square feet
Style: Single Family Residential
Year Built: 1869
Year Renovated: —
County: Litchfield County
APN: 926817

Home facts updated by county records on May 24, 2023

Other

Documents & Disclosures
Supplement Count Public: 2

Around this home

Schools

Mary P. Hinsdale School

Public PreK-2 • Assigned • 0.2mi

The Gilbert School

Public 7-12 • Assigned • 0.3mi

3/10

Provided by GreatSchools

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

3/10 Heat Factor

8 days above 93° expected this year, 18 days in 30 years

5/10 Wind Factor

26% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Winsted, CT • 06098

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

80/ 100

Very good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.7 hrs

5.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$188,000 – $227,000

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Nearby similar homes

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New listings for sale in 06098

$275,000

2 beds1 bath912 sq ft

1 Division St, Winsted, CT 06098

OPEN TODAY, 1PM TO 3PM

$319,900

2 beds2 baths1,192 sq ft

325 E Wakefield Blvd, Winsted, CT 06098

$325,000

4 beds2.5 baths2,257 sq ft

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COMING SOON

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2 beds2 baths1,346 sq ft

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4 beds2.5 baths3,486 sq ft

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OPEN TODAY, 1:30PM TO 3:30PM

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Home values near 30 Upland Rd

Data from public records.

Address	Redfin Estimate
39 Upland Rd, Winsted, CT 4 Beds \| 2 Baths \| 1801 Sq. Ft.	$280,837
12 Upland Rd, Winsted, CT 4 Beds \| 2 Baths \| 2366 Sq. Ft.	$291,224

Address	Redfin Estimate
38 Upland Rd, Winsted, CT 3 Beds \| 1.5 Baths \| 1736 Sq. Ft.	$336,101
18 Upland Rd, Winsted, CT 5 Beds \| 2 Baths \| 2338 Sq. Ft.	$342,793

Address	Redfin Estimate
11 Upland Rd, Winsted, CT 4 Beds \| 3.5 Baths \| 2620 Sq. Ft.	$426,000
42 Upland Rd, Winsted, CT 2 Beds \| 1 Baths \| 1236 Sq. Ft.	$257,451

Property information provided by Smart MLS when last listed in 2026. This data may not match . Learn more.

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