CTHomeListings.com
Home › Homes for Sale › Winchester, CT › 99 High Street

99 High Street, Winchester, CT 06098

Multi-Family For Sale · 4 Family

$575,000
$191/sqft
99 High Street, Winchester, CT
Active
Photo 2
Photo 3
Photo 4
Photo 5
14
Bedrooms
12
Bathrooms
3,012
Sq Ft
0.23
Acres
1900
Year Built

About This Home

99 High St, Winsted, CT 06098 is a multi family residential property. The Building was built in 1958 and includes 4 units as well as a garage for multi purpose storage warehouse use. It has a large swing up garage door for excellent storage. There is also a small office with an interior bathroom. 1 unit is a 2 bedroom 1.5 bath. 3 units are a 1 bedroom, 1 bath. Each unit is rented with a stable long term paying tenant. The garage is also rented to a long term tenant. The driveway parking area was recently redone with new concrete for parking access. The exterior was recently painted and has been well maintained, a new furnace has been added as well, 3 of the 4 units have been updated.

Listed by Ralph Harvey (855) 456-4945 with ListWithFreedom.com (855) 456-4945

Listing Snapshot

Price $575,000 Days on Our Site 35 days
Property Tax $1,033/yr Style 4updown - Unit(s) per Floor
Year Built 1900 Total Sq Ft 3,012
Lot Size 0.23 acres HOA Fees N/A
Bedrooms 14 Full Bathrooms 10
Total Rooms 4 Half Baths 2

Structure & Parking

Construction Frame,Brick,Other
Roof Shingle
Garage Spaces 8
Garage Type Detached Garage

Systems & Utilities

Heat No Heat
Cooling None
Hot Water No Hot Water
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Harry P. Hinsdale
Middle Pearson
High Per Board of Ed

Mortgage Calculator

$
$
%
%
Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $86/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Sep 25, 2026 Listed $575,000

Frequently Asked Questions

How much does 99 High Street in Winchester, CT cost?
This property is listed at $575,000, which works out to $191 per square foot.
How many bedrooms does 99 High Street have?
This home has 14 bedrooms and 12 bathrooms.
What is the square footage of 99 High Street?
The home is 3,012 square feet, situated on 0.23 acres.
When was 99 High Street in Winchester built?
This property was built in 1900.
Is 99 High Street, Winchester, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 99 High Street, Winchester in?
This home is served by the Winchester public school system, with Harry P. Hinsdale as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 99 High Street, Winchester, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Ralph Harvey · (855) 456-4945

ListWithFreedom.com · (855) 456-4945

MLS# 24209933 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Oct 2, 2026 1:13 PM UTC