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19 High Street, Middlefield, CT 06455

Single Family For Sale

$749,000
$184/sqft
19 High Street, Middlefield, CT
Active
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4
Bedrooms
3
Bathrooms
4,073
Sq Ft
1.2
Acres
1750
Year Built

About This Home

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.

Listed by Debbie Huscher (860) 918-4580 with Real Broker CT, LLC (855) 450-0442

Listing Snapshot

Price $749,000 Days on Our Site 43 days
Property Tax $10,617/yr Style Antique
Year Built 1750 Total Sq Ft 4,073
Lot Size 1.2 acres HOA Fees N/A
Bedrooms 4 Full Bathrooms 2
Total Rooms 8 Half Baths 1

Key Features

Interior
  • Open Floor Plan
Appliances
  • Oven/Range
  • Refrigerator
  • Dishwasher
Outdoor
  • Barn
  • French Doors
  • Patio
Nearby
  • Golf Course
  • Lake
  • Park
  • Putting Green

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 12
Garage Type Barn, Detached Garage

Systems & Utilities

Heat Hydro Air
Fuel Oil
Cooling None
Hot Water Tank Size Unknown
Water Private Well
Sewer Septic

Schools

Elem John Lyman
High Coginchaug Regional

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $885/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Aug 19, 2026 Price Reduced $749,000
Aug 3, 2026 Listed $850,000

Frequently Asked Questions

How much does 19 High Street in Middlefield, CT cost?
This property is listed at $749,000, which works out to $184 per square foot.
How many bedrooms does 19 High Street have?
This home has 4 bedrooms and 3 bathrooms.
What is the square footage of 19 High Street?
The home is 4,073 square feet, situated on 1.2 acres.
When was 19 High Street in Middlefield built?
This property was built in 1750.
Is 19 High Street, Middlefield, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 19 High Street, Middlefield in?
This home is served by the Middlefield public school system, with John Lyman as the elementary school and Coginchaug Regional as the high school.
How do I schedule a tour of 19 High Street, Middlefield, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Debbie Huscher · (860) 918-4580

Real Broker CT, LLC · (855) 450-0442

MLS# 24196454 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Sep 6, 2026 2:30 PM UTC