Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$575,000 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 14 Total Beds
  • 8 Car Garage
  • Updated 10 hours ago
See This Home
Save This Home
See This Home
Save This Home
A multi family residential property. The Building was built in 1958 and includes 4 units as well as a garage for multi purpose storage 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.

Full Property Details for 99 High St

General

  • Price: $575,000
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Multi-Family
  • Source: SMARTMLS
  • MLS ID: 24209933
  • Updated: 9/25/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 4

Rooms

Bathrooms

  • Total Bathrooms: 12
  • Full Bathrooms: 10
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 14

Parking

  • Garage: Yes
  • Garage Spaces: 8
  • Parking: Detached Garage

Location

  • County: Litchfield
  • Subdivision: Hartford
  • Neighborhood: Winsted
  • Driving Directions: Get on I-66 W in Warren County from US-522 N Take I-81 N, I-78 E, I-287 N, I-87 S, ... and CT-8 N to S Main St in Winchester Continue on S Main St. Drive to High St

School Information

  • Elementary School: Harry P. Hinsdale
  • Middle School: Pearson
  • Intermediate School: Per Board of Ed
  • High School: Per Board of Ed

Community

  • Community Name: Winsted

Heating & Cooling

  • Cooling Type: None
  • Heating Type: No Heat
  • Water Heater: No Hot Water

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: 4updown - Unit(s) per Floor
  • Construction Status: No/Resale
  • Exterior Const.: Wood
  • Basement Desc.: None
  • Roof: Shingle
  • Square Feet: 3,012
  • Above Ground: 3,012 Sq. Ft.
  • Year Built: 1900

Unit Information

Unit 1

  • Square Feet: 800
  • Total Bathrooms: 1
  • Bedrooms: 1

Unit 2

  • Square Feet: 10000
  • Total Bathrooms: 5
  • Partial Bathrooms: 1
  • Bedrooms: 6

Unit 3

  • Square Feet: 10000
  • Total Bathrooms: 5
  • Partial Bathrooms: 1
  • Bedrooms: 6

Unit 4

  • Square Feet: 800
  • Total Bathrooms: 1
  • Bedrooms: 1

Lot Features

  • Lot Size (Acres): 0.23
  • Zoning: Commercial
  • Lot Description: Corner Lot

Financial Considerations

  • Assessment Amount: $34,440
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 927680

Listed by ListWithFreedom.com, Ralph Harvey

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 99 High St —

  • Ralph Harvey

    ListWithFreedom.com

Agent Contact: (855) 456-4945 Office Contact: (855) 456-4945

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 99 High St

School District:Winchester School District
NameGradesDistance
Pearson Middle School
2 Wetmore Avenue, Winsted, CT 06098
3-60.3 mi
Batcheller Early Education Center
201 Pratt Street, Winsted, CT 06098
PK-20.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 99 High St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/25/2026
Listed
$575,000
43.75%
MLS
8/01/2024
Sold
$400,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 99 High St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,924
18%
$237,370
10%
2023
$5,888
3%
$216,160
—
2023
$5,704
2%
$216,160
29%
2022
$5,618
—
$167,510
—
2021
$5,618
—
$167,510
—
2020
$5,618
—
$167,510
—
2019
$5,618
—
$167,510
—
2018
$5,618
6%
$167,510
6%
2017
$5,292
—
$157,780
—
2016
$5,292
3%
$157,780
—
2015
$5,159
2%
$157,780
—
2014
$5,035
2%
$157,780
—
2011
$4,923
—
$157,780
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 99 High St

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by ListWithFreedom.com, Ralph Harvey

Just Listed near 99 High St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

220 Richards Rd, New Hartford, CT 06057 - Photo 1 Just Listed
$424,900

220 Richards Rd  New Hartford, CT 06057

  • Single Family
  • Active
  • Updated 1 hour ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,752
    Sq. Ft.
Listed by Linda Kessler (860) 836-6172
737 Litchfield Turnpike, New Hartford, CT 06057 - Photo 1 Just Listed
$199,000
Open House

737 Litchfield Turnpike  New Hartford, CT 06057

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,184
    Sq. Ft.
Listed by William Raveis Real Estate
168 W Pearl Rd, Torrington, CT 06790 - Photo 1 Just Listed
$314,900

168 W Pearl Rd  Torrington, CT 06790

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,082
    Sq. Ft.
Listed by Chris Clarke (860) 879-6650
110 Shirley Rd, Torrington, CT 06790 - Photo 1 Just Listed
$375,000
Open House

110 Shirley Rd  Torrington, CT 06790

  • Single Family
  • Active
  • Updated 1 hour ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,230
    Sq. Ft.
Listed by The Washington Agency

Price Reduced near 99 High St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

10 North St, Norfolk, CT 06058 - Photo 1 Price Reduced
-$74,000 (-14.83%)
$425,000

10 North St  Norfolk, CT 06058

  • Single Family
  • Active
  • Updated 4 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 3,523
    Sq. Ft.
Listed by eXp Realty
129 Sunset Ridge Rd, Norfolk, CT 06058 - Photo 1 Price Reduced
-$50,000 (-6.68%)
$699,000
Open House

129 Sunset Ridge Rd  Norfolk, CT 06058

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 3,514
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
10 North St, Norfolk, CT 06058 - Photo 1 Price Reduced
-$74,000 (-14.83%)
$425,000

10 North St  Norfolk, CT 06058

  • Multi-Family
  • Active
  • Updated 4 days ago
  • 5
    Total Beds
Listed by eXp Realty
1226 Litchfield Rd, Norfolk, CT 06058 - Photo 1 Price Reduced
-$50,000 (-9.11%)
$499,000

1226 Litchfield Rd  Norfolk, CT 06058

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,964
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l

Recent Sales near 99 High St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

162 Spencer Hill Rd, Winchester, CT 06098 - Photo 1 Sold
$650,000

162 Spencer Hill Rd  Winchester, CT 06098

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,144
    Sq. Ft.
Listed by Sullivan Real Estate Inc
Sold by Showcase Realty, Inc.
3651 Torringford St, Torrington, CT 06790 - Photo 1 Sold
$500,000

3651 Torringford St  Torrington, CT 06790

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 2,368
    Sq. Ft.
Listed by Re/Max Rise
Sold by Sullivan Real Estate Inc
736 W Wakefield Blvd, Winchester, CT 06098 - Photo 1 Sold
$525,000

736 W Wakefield Blvd  Winchester, CT 06098

  • Single Family
  • Closed
  • 1
    Bed
  • 2
    Total Baths
  • 1,308
    Sq. Ft.
Listed and Sold by Lakefront Living Realty, LLC
257 Wallens Hill Rd, Winchester, CT 06098 - Photo 1 Sold
$550,000

257 Wallens Hill Rd  Winchester, CT 06098

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,011
    Sq. Ft.
Listed by Sullivan Real Estate Inc
Sold by Marrin Santore Realty LLC

99 High Street, Winchester, CT 06098 (MLS# 24209933) is a Multi-Family property with 4 units containing 14 bedrooms, 10 full bathrooms and 2 partial bathrooms. 99 High Street is currently listed for $575,000 and was received on September 25, 2026. Want to learn more about 99 High Street? Do you have questions about finding other Multi-Family real estate for sale in Winsted? You can browse all Winsted real estate or contact a Coldwell Banker agent to request more information.

Tour this property