# 99 High Street, Winchester, CT 06098 > **TL;DR:** 14bd/12ba residential multi family, $575,000 ($191/sqft), built 1900, 3,012 sqft. > 8-car garage. Est. $3,076/mo. Listed 10 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $575,000 | | Price/sqft | $191 | | Bedrooms | 14 | | Bathrooms | 10 full, 2 half | | Square Feet | 3,012 | | Year Built | 1900 | | Lot Size | 10,019 sqft (0.23 acres) | | Garage | 8-car | | Property Type | Residential Multi Family (Other) | | Status | Active | | Days on Market | 10 | ## Why This Home Stands Out - **Large Garage** - 8-car garage ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,908 | | Estimated Insurance | $168 | | **Total** | **$3,076** | ## Nearby Schools - **Elementary:** Harry P. Hinsdale - **High:** Per Board of Ed ## Key Amenities - 8-car garage ## Property Highlights - Built in 1900 - 0.23 acre lot ## Description ### Agent Description 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. ## Location - **Address:** 99 High Street, Winchester, CT 06098 - **County:** Litchfield - **Neighborhood:** Hartford - **Coordinates:** 41.922621, -73.070991 - **Google Maps:** https://www.google.com/maps?q=41.922621,-73.070991 ## Listing Agent - **Name:** Ralph Harvey - **Brokerage:** ListWithFreedom.com - **Phone:** (855) 455-4945 - **Broker Phone:** (855) 455-4945 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/99-High-St_Winsted_CT_06098_M38283-83143?f=listhub&s=CTMLS&m=24209933&c=propsimple) ## Photos ![99 High Street - Photo 1](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f3236019201r.jpg) ![99 High Street - Photo 2](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f3442820678r.jpg) ![99 High Street - Photo 3](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f1947102843r.jpg) ![99 High Street - Photo 4](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f2266846262r.jpg) ![99 High Street - Photo 5](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f3154015613r.jpg) ![99 High Street - Photo 6](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f1393721660r.jpg) ![99 High Street - Photo 7](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f1861344863r.jpg) ![99 High Street - Photo 8](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f2311813488r.jpg) ![99 High Street - Photo 9](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f2807178685r.jpg) ![99 High Street - Photo 10](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f3730655421r.jpg) ![99 High Street - Photo 11](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f712124119r.jpg) ![99 High Street - Photo 12](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f1015708336r.jpg) ![99 High Street - Photo 13](http://lh.rdcpix.com/c20a679e3739e0e900e0e056b4f54a84l-f3440428108r.jpg) --- **MLS#:** 24209933 | **Updated:** 2026-10-02 **Source:** listhub *Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/99-high-street-winchester-ct-06098-24209933) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/99-high-street-winchester-ct-06098-24209933#listing", "url": "https://www.propertysimple.ai/listing/99-high-street-winchester-ct-06098-24209933", "name": "99 High Street, Winchester, CT 06098", "description": "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. 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