Off market oct 2022 for $201K

$225,498

Est. refi paymentEst. refi $1,613/mo

•

576

sq ft

108 West Rd, Winsted, CT 06098

About this home

Charming, historic home in Winchester Center with modern updates and the convenience of single level living! Once an old schoolhouse built in 1800, this adorable home has been transformed into quite the cozy abode. This home offers a lovely new enclosed porch with wood-plank walls and ceiling, as well as hardwood floors throughout the home, and a sunny living room with a distinctive, high arching ceiling. Kitchen has been nicely updated with granite counters, tile backsplash and stainless steel appliances. The bedroom has a private, full bath and stairs leading to a great loft space with skylight for overnight guests or a convenient home office. An additional loft space is also available for use or storage. New well and septic recently installed and new double insulated stainless steel oil tank! Crushed stone driveway has also been recently redone. Home feels like a quiet, country retreat with nature's surroundings in this private backyard with perennials, fence and wooded borders. Store your lawn and garden equipment in the 24x14 shed. Minutes from Lake Winchester, Highland Lake and Crystal Lake for more ways to enjoy the outdoors close by! Tour this adorable home today!

Single-familyProperty Type

1800Year Built

0.32 acresLot Size

$391Est. Price/Sq.Ft.

Listed by Jonathan Hastings • KW Legacy Partners

Listed by Sandie Terenzi • KW Legacy Partners

Bought with Michael Price • KW Legacy Partners

Source:Smart MLS #170515495

Redfin Estimate

$225,498

$24K since sold in October 2022$14K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 55.3% lower than the average sale price ($505K) of 6 comparable homes.

SOLD SEP 17, 2026
$320,000
A
2 beds1 bath1,128 sq ft
729 W Wakefield Blvd, Winsted, CT 06098
SOLD SEP 4, 2026
$721,000
B
2 beds1 bath760 sq ft
812 W Wakefield Blvd, Winsted, CT 06098
SOLD JUL 21, 2026
$525,000
C
1 bed1.5 baths1,308 sq ft
736 W Wakefield Blvd, Winsted, CT 06098
SOLD SEP 1, 2026
$960,000
D
2 beds1.5 baths1,472 sq ft
204 E Wakefield Blvd, Winsted, CT 06098
SOLD FEB 20, 2026
$231,000
E
2 beds1 bath1,051 sq ft
817 E Wakefield Blvd, Winsted, CT 06098
SOLD AUG 6, 2026
$270,000
F
3 beds1 bath1,008 sq ft
104 Maloney Ct, Winsted, CT 06098

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Earn from this home

Sell

$61,470

Est. take-home

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Refinance

Est. cash available

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Rent

$1,453/mo

Redfin rental estimate

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Market trends in 06098, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.4%

0.8% MoM

Median sale price

$355K

$8K MoM

Avg. days on market

48d

6 days MoM

Recently sold homes

1 MoM

New listings for sale

OPEN TODAY, 12PM TO 2PM
$239,900
3 beds1 bath1,201 sq ft
35 Prospect St, Winsted, CT 06098
$215,000
2 beds1.5 baths1,204 sq ft
111 Riverton Rd #79, Winsted, CT 06098
$300,000
4 beds2.5 baths2,407 sq ft
205 Perch Rock Trl, Winsted, CT 06098
$449,000
3 beds2.5 baths1,659 sq ft
150 E Lake St, Winsted, CT 06098
$289,900
4 beds1.5 baths1,664 sq ft
173 Gilbert Ave, Winsted, CT 06098
$339,900
3 beds1 bath1,488 sq ft
50 Overlook Rd, Winsted, CT 06098
$575,000
14 beds11 baths3,012 sq ft
99 High St, Winsted, CT 06098
$374,900
6 beds3 baths2,887 sq ft
95 Williams Ave, Winsted, CT 06098
See all

Provided by Redfin

Sale history for 108 West Rd

Date

Event

Price

Smart MLS #170515495

Oct 4, 2022

Sold

$201,000

$349/sq ft

Aug 10, 2022

Listed

$185,000

$321/sq ft

Smart MLS #170334710

Oct 30, 2020

Sold

$137,500

$239/sq ft

Sep 15, 2020

Contingent

—

Sep 11, 2020

Listed

$137,500

$239/sq ft

Absolutely adorable year round Cottage in historic Winchester center! This 1800 cottage was once an old school house. Minutes from 2 lakes & private pond. Completely redone, kitchen with granite counters and stainless steel appliances, bedroom with a loft area, gleaming hardwood flooring, cathedral ceilings, 24X14 storage shed, beautiful 1/2 acre lot, walking distance to Winchester Lake, the perfect little getaway spot!

Public Records

Oct 17, 2011

Sold

$107,000

$186/sq ft

Smart MLS #L135576

Aug 4, 2010

Listed

$115,000

$200/sq ft

Smart MLS #L108010

Oct 9, 2003

Listed

$128,000

$222/sq ft

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Tax history for 108 West Rd

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.32 Acres

Year renovated

—

Sq. Ft.

576

Year built

1800

Style

Single Family Residential

County

Litchfield County

APN

925394

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on May 25, 2023.

Property details

Parking

Garage Information
Garage & Parking: Driveway

Interior

Interior Information
Total Rooms: 4
Cooling System: Ceiling Fans, Window Unit
Appliances Included: Oven/Range, Range Hood, Refrigerator, Washer, Dryer

Bathroom Information
# of Baths (Full): 1

Bedroom Information
Beds Total: 1

Room Information
Room Count: 5
Basement Description: Crawl Space

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Wood
Exterior Features: Gutters, Porch-Enclosed, Shed

Lot Information
Lot Description: Level Lot

Building Information
Foundation Type: Stone
Construction Description: Frame

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 576
Driveway Type: Crushed Stone

Financial

Assessments Information
Assessed Value: $75,530

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Oil
Heat Type: Baseboard
Heat Fuel Type: Oil
Fuel Tank Location: Above Ground
Energy Features: Storm Doors, Storm Windows

Location

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

Location Information
State: Connecticut
Nearby Amenities: Lake, Park, Playground/Tot Lot
Directions: Newfield Rd to West Rd.
County: Litchfield

Public facts

Beds: 1
Baths: 1.0
Sq. Ft.: 576
Stories: 1.0
Lot Size: 0.32 acres
Style: Single Family Residential
Year Built: 1800
Year Renovated: —
County: Litchfield County
APN: 925394

Home facts updated by county records on May 24, 2023

Other

Documents & Disclosures
Supplement Count Public: 5

Around this home

Schools

Mary P. Hinsdale School

Public PreK-2 • Assigned • 3.8mi

The Gilbert School

Public 7-12 • Assigned • 4.0mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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

In this area, properties receive around 8.7 hours in June and 4.1 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.1 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$215,000 – $260,000

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New listings for sale in 06098

OPEN TODAY, 12PM TO 2PM

$239,900

3 beds1 bath1,201 sq ft

35 Prospect St, Winsted, CT 06098

$215,000

2 beds1.5 baths1,204 sq ft

111 Riverton Rd #79, Winsted, CT 06098

$300,000

4 beds2.5 baths2,407 sq ft

205 Perch Rock Trl, Winsted, CT 06098

$449,000

3 beds2.5 baths1,659 sq ft

150 E Lake St, Winsted, CT 06098

$289,900

4 beds1.5 baths1,664 sq ft

173 Gilbert Ave, Winsted, CT 06098

$339,900

3 beds1 bath1,488 sq ft

50 Overlook Rd, Winsted, CT 06098

$575,000

14 beds11 baths3,012 sq ft

99 High St, Winsted, CT 06098

$374,900

6 beds3 baths2,887 sq ft

95 Williams Ave, Winsted, CT 06098

Home values near 108 West Rd

Data from public records.

Address	Redfin Estimate
105 West Rd, Winsted, CT 4 Beds \| 1 Baths \| 1114 Sq. Ft.	$353,207
104 West Rd, Winsted, CT 3 Beds \| 1 Baths \| 1544 Sq. Ft.	$330,995

Address	Redfin Estimate
102 West Rd, Winsted, CT 2 Beds \| 2 Baths \| 2144 Sq. Ft.	$498,689
122 West Rd, Winsted, CT 3 Beds \| 2.5 Baths \| 2611 Sq. Ft.	$546,186

Address	Redfin Estimate
127 West Rd, Winsted, CT 2 Beds \| 1 Baths \| 900 Sq. Ft.	$305,231
107 West Rd, Winsted, CT 2 Beds \| 2 Baths \| 2208 Sq. Ft.	$382,723

Property information provided by Smart MLS when last listed in 2022. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06098, CT

Sale history for 108 West Rd

Tax history for 108 West Rd

Public record

Property details

Around this home

Schools

Lifestyle

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06098

Home values near 108 West Rd

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