# 30 Upland Road, Winchester, CT 06098

> **TL;DR:** 4bd/2ba single family, $220,000 ($119/sqft), built 1869, 1,844 sqft. Est. $953/mo. Listed 18 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $220,000 |
| Price/sqft | $119 |
| Bedrooms | 4 |
| Bathrooms | 2 full |
| Square Feet | 1,844 |
| Year Built | 1869 |
| Lot Size | 7,405 sqft (0.17 acres) |
| Property Type | Single Family (Other) |
| Status | For Sale |
| Days on Market | 18 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $953 |
| **Total** | **$953** |

## Nearby Schools

- **Elementary:** Per Board of Ed
- **High:** Per Board of Ed

## Property Highlights

- Built in 1869
- 0.17 acre lot
- 1 parking spaces

## Description

### Agent Description
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**

## Location

- **Address:** 30 Upland Road, Winchester, CT 06098
- **County:** Litchfield
- **Coordinates:** 41.929206, -73.077054
- **Google Maps:** https://www.google.com/maps?q=41.929206,-73.077054

## Listing Agent

- **Name:** Jeffrey Liskin
- **Brokerage:** Northwest CT Realty
- **Phone:** 8606010991
- **Email:** jliskinrealty@gmail.com

## Primary Photo

![30 Upland Road - Primary Photo](http://lh.rdcpix.com/0f229ce5837855c575eaa5f5d5d329a4l-f754279677r.jpg)

*26 total photos available on [listing page](https://www.propertysimple.com/listing/30-upland-road-winchester-ct-06098-24176921)*

---

**MLS#:** 24176921 | **Updated:** 2026-06-18
**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.com/listing/30-upland-road-winchester-ct-06098-24176921)

---

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