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4 Beds
3 Baths
4,073 sqft

$749,000

19 High Street, Middlefield CT, 06455

Price per sqft$183.89
Built in1750
Property size4,073 sqft
Property typeResidential

Overview

Active

Listed Aug 3, 2026

Updated 13 days ago

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.

$4,983/mo

Est. mortgage payment based on a $749,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
24196454

Interior Features

Bedrooms
4
Bathrooms
3
Fireplace
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
1.2 Acres

Other Property Details

Taxes
$10,617
Tax Frequency
Annually
Garage
Yes
MLS provider logo

Listed by Debbie Huscher with Real Broker CT, LLC (860) 918-4580

The IDX display contains information sourced from SmartMLS, Inc. as of 9/7/2026. This information is for personal, non-commercial use only and may not be used for any purpose other than identifying properties the viewer may be interested in purchasing. MLS data is generally considered reliable but is not guaranteed accurate by the MLS. Buyers are responsible for verifying all information and should conduct their own investigation or consult a professional. Some MLS data may have been provided by sources other than the listing agent. Unless stated in writing, the Broker/Agent has not verified information obtained from outside sources. The Broker/Agent may or may not have been the listing and/or selling agent, and cannot guarantee the accuracy of any property location shown on a map. Any offer of compensation is made only to participants of the MLS where the listing is filed.

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Data last updated on 9/7/2026 at 2:14 AM UTC.

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