19 High Street

A rare opportunity featuring a beautifully crafted 2008 addition, the original circa-1750 central chimney Colonial awaiting restoration, detached garage, expansive barn, and picturesque grounds.
Thoughtfully designed 2008 addition offers comfortable modern living with a welcoming covered porch and seamless connection to the original circa-1750 Colonial.
Exceptional outbuildings include a detached garage and large barn with leased solar panels, offering incredible versatility for vehicles, hobbies, storage, and workshop space.
The great room showcases wide-plank floors, abundant natural light, and a stunning stone fireplace.
Expansive great room with soaring vaulted ceilings, wide-plank pine floors, oversized windows, and French doors opening to the covered porch and grounds.
An impressive fieldstone fireplace with a reclaimed timber mantel adds warmth and architectural character.
The open-concept design seamlessly connects the soaring great room, country kitchen, and second-floor loft, while French doors open to the covered porch for effortless indoor-outdoor living.
A beautifully appointed kitchen with handcrafted details, abundant cabinetry, and an oversized island made for entertaining.
The custom country kitchen features an oversized gathering island and opens seamlessly to the soaring great room, creating an ideal space for entertaining and everyday living.
The custom country kitchen with its oversized gathering island seamlessly connects the 2008 addition to the original 1750 center chimney Colonial, offering the rare opportunity to enjoy modern living while restoring a true piece of Connecticut history.
Striking open-concept design features soaring ceilings, an impressive open staircase, expansive second-story loft, and beautiful wide-plank pine floors that bring warmth and character throughout.
Expansive second-floor loft overlooking the soaring great room provides exceptional flexible space for a home office, media room, fitness area, studio, or additional living space.
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Spacious first-floor primary suite offers convenient one-level living with wide-plank pine floors and generous natural light.
Spacious primary bath offers a spa-like retreat with a jetted soaking tub, separate shower, expansive dual-sink vanity, and plenty of room to unwind.
Imagine Restoring 275 Years of History While Living Comfortably in the Modern Addition.
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Active
$749,000
4 beds4,073 sqft$184/sqft
19 High St, Middlefield, CT 06455
Est: $4,692/moGet pre-approved
Single FamilyProperty Type
1.2 acresLot Size
1750Year Built
$184/sq ftPrice per sq ft
12 carsParking Spaces

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...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.
25 days on Market
  • Listed by: Debbie D Huscher 860.918.4580 dhuscher@comcast.net • Real Broker CT, LLC
Last updated: 09/06/2026 02:30 PM • Source: SMARTMLS, MLS#: 24196454

Location

Listing Courtesy of Real Broker CT, LLC, Debbie D Huscher
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Property Information for 19 High Street

Property Details
  • Taxes: $10,617 / year
  • MLS Type: Residential
  • County: Middlesex County
  • Basement Description: Full
  • Direct Waterfront: No
  • Expected Active Date: 08-14-2026
  • Garages Number: 12
  • Style: Antique
  • Garage Parking Info: Barn, Detached Garage
  • Swimming Pool: No
  • Expected On Market Date: 08-14-2026
Building Information
  • Year Built: 1750
  • Lot Size: 1.20 AC / 52,272 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Baileyville Rd to Way to High St
  • Elementary School: John Lyman
  • High School: Coginchaug Regional
  • Latitude: 41.515909
  • Longitude: -72.725837
  • Neighborhood Amenities: Golf Course, Lake, Park, Putting Green
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2026-June 2027
  • Property Tax: $10,617
Virtual Tour
Interior and Exterior Features
Exterior Features
  • Exterior Features: Barn, French Doors, Patio
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Dishwasher
  • Attic Description: Walk-up
  • Cooling System: None
  • Heat Type: Hydro Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Open Floor Plan
  • Laundry Room Info: Main Level
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Wide Board Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: Full Bath
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 4
  • Room Entry Order: 4
  • Room Level: Upper
  • Room Type: Bedroom
Room 5
  • Listing Key: 5828CFBFADE314FFE0631A01100AE075
  • Room Entry Order: 5
  • Room Level: Main
  • Room Type: Kitchen
Room 6
  • Room Entry Order: 6
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Wood
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1750
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 4073
Lot Information
  • Lot Description: Level Lot
  • Parcel Number: 1000699
  • Sq Ft Est Heated Above Grade: 4073.0
  • Sq Ft Total: 4073.0
  • Zoning: MD
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Tank Size Unknown
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Vacant

Property History for 19 High Street

DateEvent & SourcePriceAppreciation
Dec 28, 2004

Closed (Public Record)

Public Record #154012969

$138,000—
DateEvent & SourcePrice
12/28/2004

Closed (Public Record)

Public Record #154012969

$138,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 19 High Street

Taxable ValueLand$91,900Additions$240,300Total$332,200
Tax Record2025$9,900 ($825 / month)
Home Facts
Beds2Baths1.5Total Finished SqFt4,073 SqFtAbove Grade Finished SqFt4,073 SqFtUnfinished Basement SqFt3,109 SqFtStories2Lot Size52,272 SqFtStyleSingle Family ResidenceYear Built1760Year Renovated1760ZoningMDCountyLOWER CONNECTICUT RIVERAPNMFLD M:10 B:10.5 L:82-1

Schools near 19 High Street

This home is within Regional School District 13.
Rating
School
Type
Grades
Distance
John Lyman School
Public - 2 to 3
Frank Ward Strong School
Public - 6 to 8
Coginchaug Regional High School
Public - 9 to 12
Middlefield Memorial School
Public - 4 to 5
Rating
School
Distance
John Lyman School
Public2 to 3

Frank Ward Strong School
Public6 to 8

Coginchaug Regional High School
Public9 to 12

Middlefield Memorial School
Public4 to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 19 High Street, Middlefield, CT 06455

19 High Street is a single family home for sale in Middlefield, CT 06455. This property was listed for sale on August 3, 2026 by Real Broker CT, LLC, it's currently listed at $749,000. It has been on the market for a total of 25 days and was last sold on December 28, 2004. This listing's school district is Regional School District 13. Nearby schools include John Lyman School, Frank Ward Strong School and Coginchaug Regional High School. 19 High Street is a 4-bed, 3-bath, 4,073 sqft single family home built in 1750.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Real Broker CT, LLC, Debbie D Huscher

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.