For Sale
Price CutPrice Drop: $50K (09/21)
Single family home for sale at 19 High St, Middlefield, CT 06455 | MLS# 24196454 | Listing updated on 2026-09-21
Photo 1 of Single family home for sale at 19 High St, Middlefield, CT 06455 | MLS# 24196454 | Listing updated on 2026-09-21
Photo 2 of Single family home for sale at 19 High St, Middlefield, CT 06455 | MLS# 24196454 | Listing updated on 2026-09-21
Photo 3 of Single family home for sale at 19 High St, Middlefield, CT 06455 | MLS# 24196454 | Listing updated on 2026-09-21
Photo 4 of Single family home for sale at 19 High St, Middlefield, CT 06455 | MLS# 24196454 | Listing updated on 2026-09-21
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$699,000

Monthly Est:$3,479

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon4,073sqft

19 High St, Middlefield, CT 06455

$3,479/moEst:

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  • Single Family Residence

  • Built in 1750

  • $-- HOA

  • 1.2 acres lot

  • $172/sq.ft

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.

  • Houzeo last checked: 12 hours ago
  • Listing updated: September 21, 2026 at 4:49 pm
  • Listing Provided by: Debbie Huscher | Real Broker CT, LLC
  • Source: SMART MLS-CT | MLS#: 24196454 SMART MLS-CT

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Middlesex County

  • City

    Middlefield

  • Neighborhood

    --

  • Year Built

    1750

  • HOA Fees

    -

  • Finished Area

    4,073 sqft

  • Lot Size

    1.2 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24196454

  • MLS Status

    Active

  • Days on Market

    67

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 3

Interior

  • Interior Features

    Open Floor Plan

  • Appliances

    Oven/range, Refrigerator, Dishwasher

  • Sewer

    Septic

  • Heating

    Oil

  • Cooling

    None

  • Exterior Features

    Barn, French Doors, Patio

Construction

  • Year Built

    Year Built: 1750

  • Home type

    Single Family Residence

  • Architectural Style

    Antique

  • Foundation Details

    Concrete

  • Roof

    Asphalt Shingle

Utilities & Energy

  • Laundry Features

    Main Level

  • Parking Features

    Barn, Detached Garage

  • Basement

    Full

  • Water Source

    Private Well

Other Features

  • Subdivision Name

    N/a

  • Lot Features

    Level Lot

Price History

DateEventPrice

09/21/2026

Source: mls_logoSMART MLS-CT #24196454

Price Decreased

$699,000 -6.68%

$172/sqft

08/19/2026

Source: mls_logoSMART MLS-CT #24196454

Price Decreased

$749,000 -11.88%

$184/sqft

08/14/2026

Source: mls_logoSMART MLS-CT #24196454

Listed for Sale

$850,000

$209/sqft

08/03/2026

Source: mls_logoSMART MLS-CT #24196454

Coming Soon

$850,000

$209/sqft

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Oct 09, 2026, 02:30PM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group