# 19 High Street, Middlefield, CT 06455

> **TL;DR:** 4bd/3ba single family, $699,000 ($172/sqft), 4,073 sqft.
> Fireplace, Solar, 12-car garage. Est. $3,739/mo. Listed 56 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $699,000 |
| Price/sqft | $172 |
| Bedrooms | 4 |
| Bathrooms | 2 full, 1 half |
| Square Feet | 4,073 |
| Lot Size | 52,272 sqft (1.20 acres) |
| Garage | 12-car |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 56 |

## Why This Home Stands Out

- **Solar Panels** - Solar panels listed
- **Large Garage** - 12-car garage

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $3,535 |
| Estimated Insurance | $204 |
| **Total** | **$3,739** |

## Nearby Schools

- **Elementary:** John Lyman
- **High:** Coginchaug Regional

## Key Amenities

- Fireplace
- Solar
- 12-car garage

## Property Highlights

- Built in 1750
- 1.20 acre lot
- Fireplace

## Description

### Agent Description
Older than America, the historic Chilson Bailey House offers a rare opportunity to own a true circa 1750 center-chimney Colonial while enjoying the comfort of a thoughtfully designed 2008 addition. Offering four bedrooms in total, two bedrooms are located within the original 1750 portion of the home, which is not currently livable and requires renovation. This gives the next owner the opportunity to restore an authentic piece of Connecticut history at their own pace while enjoying comfortable living from day one. Everyday living takes place in the 2,963-square-foot addition, featuring a spacious country kitchen with an oversized island, a soaring great room with a floor-to-ceiling stone fireplace, wide-plank pine floors, a first-floor primary suite, and an expansive second-floor loft ideal for a home office, family room, or creative space. Outside, an impressive barn and detached garage offer exceptional space for car collectors, hobbyists, contractors, woodworking enthusiasts, or anyone needing room for projects, equipment, or recreational vehicles. Significant improvements have already been completed, including the addition, detached garage, septic system, 200-amp electrical service, leased solar, and new windows in the original home. For the buyer who sees possibility where others see a project, this is a chance to live comfortably today while bringing the historic heart of an extraordinary Connecticut property back to life.

## Location

- **Address:** 19 High Street, Middlefield, CT 06455
- **County:** Middlesex
- **Coordinates:** 41.515732, -72.72606
- **Google Maps:** https://www.google.com/maps?q=41.515732,-72.72606

## Virtual Tour & Media

- **Video Tour:** https://chilsonbailey.netlify.app/

## Listing Agent

- **Name:** Debbie Huscher
- **Brokerage:** Real Broker CT, LLC
- **Phone:** 8609184580
- **Broker Phone:** (855) 450-0442
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/19-High-St_Middlefield_CT_06455_M49091-52888?f=listhub&s=CTMLS&m=24196454&c=propsimple)

## Photos

![19 High Street - Photo 1](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f3215210312r.jpg)

![19 High Street - Photo 2](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f935994779r.jpg)

![19 High Street - Photo 3](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f1058903727r.jpg)

![19 High Street - Photo 4](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f2313126507r.jpg)

![19 High Street - Photo 5](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f2795556936r.jpg)

![19 High Street - Photo 6](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f2142002667r.jpg)

![19 High Street - Photo 7](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f1158332416r.jpg)

![19 High Street - Photo 8](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f468865991r.jpg)

![19 High Street - Photo 9](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f667770647r.jpg)

![19 High Street - Photo 10](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f1021810144r.jpg)

![19 High Street - Photo 11](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f601202963r.jpg)

![19 High Street - Photo 12](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f2179635165r.jpg)

![19 High Street - Photo 13](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f3569046679r.jpg)

![19 High Street - Photo 14](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f191430524r.jpg)

![19 High Street - Photo 15](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f3088308445r.jpg)

![19 High Street - Photo 16](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f259649359r.jpg)

![19 High Street - Photo 17](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f792672865r.jpg)

![19 High Street - Photo 18](http://lh.rdcpix.com/5ac7a195c673d52b4bfc4313653e2a46l-f120271127r.jpg)

---

**MLS#:** 24196454 | **Updated:** 2026-09-21
**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/19-high-street-middlefield-ct-06455-24196454)

---

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