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19 High Street

Middlefield, CT 06455
  • $699,000
  • STATUS: Active
  • ON SITE: 73 Days
  • MLS #: 24196454
UPDATED: 52 min ago
$699,000
  • 4
    BEDS
  • 1.2
    ACRES
  • 2
    BATHS
  • 1
    1/2 BATHS
  • 4,073
    SQFT
  • $172
    $/SQFT
Type:
Single-Family Home
Built:
1750
County:
Area:

School Information

Elementary School:
High School:

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.

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-10-16T10:10:45.077.
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19 High Street Middlefield, CT 06455

  • Price: $699,000
  • Status: Active
  • On Site: 73 Days
  • Updated: 52 min ago
  • MLS #: 24196454
4
Beds
2
Baths
1
½ Baths
1.2
Acres
4,073
SQFT
$172
$/SQFT
1750
Built
County:
Middlesex
Area:
Middlefield
Elementary School:
John Lyman
High School:
Coginchaug Regional
Property 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.
Exterior Features

Direct Waterfront YN No Exterior Features BarnFrench DoorsPatio Exterior Siding Wood Garage And Parking BarnDetached Garage Lot Description Level Lot Nearby Amenities Golf CourseLakeParkPutting Green Roof Information Asphalt Shingle Style Antique Swimming Pool YN No Waterfront Description Not Applicable

Interior Features

Appliances Included Oven/RangeRefrigeratorDishwasher Attic Description Walk-up Attic YN Yes Basement Description Full Cooling System None Fireplaces Total 1 Heat Type Hydro Air Interior Features Open Floor Plan Laundry Room Info Main Level Living Area SQFTPer Public Record 4073 Rooms Living Room (Main Level FireplaceWide Board Floor) Bedroom (Upper Level) Primary Bedroom (Main Level Full Bath) Kitchen (Main Level) Bedroom (Upper Level) Dining Room (Main Level) Bedroom (Upper Level) Sq Ft Est Heated Above Grade 4073 Total Rooms 8

Property Features

Agent Owner YN No Bank Owned Property No Foundation Type Concrete Fuel Tank Location In Basement Heat Fuel Type Oil Home Owners Assocation No Home Warranty Offered YN No Hot Water Description Tank Size Unknown New Construction Type No/Resale Potential Short Sale No Sewage System Septic Tax Year July 2026-June 2027 Under Agreement Yn No Water Source Private Well Zoning MD

Listing information © 2026 Smart MLS
Listing provided courtesy of Debbie Huscher of Real Broker CT, LLC: (855) 450-0442.


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-10-16T10:10:45.077.
 
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