Regency Key
Regency Real Estate
The Key To Your New Home
← Back to Search
MLS 24196454 For Sale Price Reduced Updated September 23, 2026
19 High Street

Middlefield, Connecticut 06455

$699,000
On market 39 days
19 High Street
1 / 18

About This Property

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.

Property Details

Interior

Heat
Hydro Air — Oil
Cooling
None
Fireplaces
1
Basement
Full
Interior Features
Open Floor Plan

Exterior & Lot

Roof
Asphalt Shingle
Construction
Construction
Exterior Features
Barn French Doors Patio
Lot Description
Level Lot
Garage & Parking
Barn Detached Garage

Utilities & Systems

Water Source
Private Well
Sewer
Septic

Community & Schools

Elementary
John Lyman
High
Coginchaug Regional
Nearby Amenities
Golf Course Lake Park Putting Green

Appliances

Included
Oven/Range Refrigerator Dishwasher

19 High Street

Middlefield , Connecticut 06455

$699,000

Was $850,000 Reduced

On market 39 days

Beds
4
Baths
3
SqFt
4,073
Type
Single Family
County Middlesex
Garage 12
Rooms -
Lot Size 1.20 Acres
Property Tax $10,617
Assessed Value $332,200
Year Built 1750
Style Antique
Zoning MD

Payment Estimate

30-year fixed. Includes taxes; estimates only.

Estimated Monthly Payment
—
Open the full mortgage calculator →

Property Map

Map location is based on the property address.

Listing information is deemed reliable but not guaranteed and is sourced from the local MLS feed. Brokerage shown: RLBR01.

Virtual Tour

Menu