# 50 Overlook Road, Winchester, CT 06098

> **TL;DR:** 3bd/1ba single family, $339,900 ($228/sqft), built 1949, 1,488 sqft.
> 3-car garage. Est. $1,818/mo. Listed 34 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $339,900 |
| Price/sqft | $228 |
| Bedrooms | 3 |
| Bathrooms | 1 full |
| Square Feet | 1,488 |
| Year Built | 1949 |
| Lot Size | 42,253 sqft (0.97 acres) |
| Garage | 3-car |
| Property Type | Single Family (Other) |
| Status | Active Under Contract |
| Days on Market | 34 |

## Why This Home Stands Out

- **Large Garage** - 3-car garage

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $1,719 |
| Estimated Insurance | $99 |
| **Total** | **$1,818** |

## Nearby Schools

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

## Key Amenities

- 3-car garage

## Property Highlights

- Built in 1949
- 0.97 acre lot
- 8 parking spaces

## Description

### Agent Description
Lovingly maintained by the same family since it was built in 1949, this 3-bedroom Colonial offers approximately 1,500 sq. ft. of living space on a 1-acre lot on the outskirts of town, yet within walking distance to the beach at Highland Lake. The main level features a spacious living room, large kitchen, dining room, full bath and inviting 3-season porch. Upstairs are three comfortable bedrooms with ample closet space. Hardwood floors run throughout the home, adding to its classic charm. Energy-conscious features include three heating sources: an oil-fired boiler, pellet stove in the living room and a magnificent soapstone wood stove in the lower level. The home also offers plenty of insulation, thermopane windows and a roof installed in 2021. Outside, you'll find excellent garage and storage space, including a large barn/garage with room for vehicles and a workshop, plus an additional detached garage. Set on nearly an acre with convenient access to Highland Lake and town amenities, this well-cared-for home is ready for its next chapter. This one is worth seeing!

## Location

- **Address:** 50 Overlook Road, Winchester, CT 06098
- **County:** Litchfield
- **Coordinates:** 41.921196, -73.092103
- **Google Maps:** https://www.google.com/maps?q=41.921196,-73.092103

## Listing Agent

- **Name:** David Sartirana
- **Brokerage:** Northwest CT Realty
- **Broker Phone:** (860) 379-7245
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/50-Overlook-Rd_Winsted_CT_06098_M36926-51685?f=listhub&s=CTMLS&m=24210012&c=propsimple)

## Photos

![50 Overlook Road - Photo 1](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f2752563784r.jpg)

![50 Overlook Road - Photo 2](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f4137626212r.jpg)

![50 Overlook Road - Photo 3](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f1159082392r.jpg)

![50 Overlook Road - Photo 4](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f3805609231r.jpg)

![50 Overlook Road - Photo 5](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f3227049773r.jpg)

![50 Overlook Road - Photo 6](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f3060888730r.jpg)

![50 Overlook Road - Photo 7](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f3890649545r.jpg)

![50 Overlook Road - Photo 8](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f1247564817r.jpg)

![50 Overlook Road - Photo 9](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f2943047320r.jpg)

![50 Overlook Road - Photo 10](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f3112031856r.jpg)

![50 Overlook Road - Photo 11](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f4243942542r.jpg)

![50 Overlook Road - Photo 12](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f1374067360r.jpg)

![50 Overlook Road - Photo 13](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f218256643r.jpg)

![50 Overlook Road - Photo 14](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f1191997448r.jpg)

![50 Overlook Road - Photo 15](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f3736665682r.jpg)

![50 Overlook Road - Photo 16](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f711916927r.jpg)

![50 Overlook Road - Photo 17](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f976150105r.jpg)

![50 Overlook Road - Photo 18](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f997724077r.jpg)

![50 Overlook Road - Photo 19](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f3379845867r.jpg)

![50 Overlook Road - Photo 20](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f1077508869r.jpg)

![50 Overlook Road - Photo 21](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f2416711761r.jpg)

![50 Overlook Road - Photo 22](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f3919210525r.jpg)

![50 Overlook Road - Photo 23](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f674816990r.jpg)

![50 Overlook Road - Photo 24](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f2074334247r.jpg)

![50 Overlook Road - Photo 25](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f745598341r.jpg)

![50 Overlook Road - Photo 26](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f1461059408r.jpg)

![50 Overlook Road - Photo 27](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f931620787r.jpg)

![50 Overlook Road - Photo 28](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f4110009476r.jpg)

![50 Overlook Road - Photo 29](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f3322426648r.jpg)

![50 Overlook Road - Photo 30](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f1351281739r.jpg)

![50 Overlook Road - Photo 31](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f2368573569r.jpg)

![50 Overlook Road - Photo 32](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f3857766043r.jpg)

![50 Overlook Road - Photo 33](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f2008547751r.jpg)

![50 Overlook Road - Photo 34](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f1505282440r.jpg)

![50 Overlook Road - Photo 35](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f1404754427r.jpg)

![50 Overlook Road - Photo 36](http://lh.rdcpix.com/c51e28d7ad91ec68089ad1d8baeccb71l-f2810946282r.jpg)

---

**MLS#:** 24210012 | **Updated:** 2026-10-25
**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/50-overlook-road-winchester-ct-06098-932a3cd8ed0d4a52923fa4e62653aa0b)

---

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