19 High Street
Middlefield, CT 06455
2
Bed
2
Bath
4,073Sqft
1.20Acres(Lot)
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 beautifully designed 2008 addition. The original 1750 home is not currently livable and is ready for renovation, providing the next owner the chance to restore an authentic piece of Connecticut history at their own pace. Everyday living takes place in the thoughtfully designed 2009 addition featuring 2,963 square feet of living space, a spacious country kitchen with an oversized island, 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, the impressive barn and detached ga
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total beds: 2Bathroom Information
Total Baths: 2 Full Baths: 1 Half Baths: 1Room Information
Rooms Total: 8 Has Basement: Yes Basement: Full -
Roofing Information
Asphalt -
Interior Features
Open Floorplan Roof: Asphalt Appliances: Dishwasher, Range, Oven, Refrigerator Laundry Features: Main Level -
Heating & Cooling
Has Heating: Yes Heating: Oil Cooling: None
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Building Information
Year Built: 1750 Building Area Total: 4073 Construction Materials: Wood Siding, Frame Patio And Porch Features: Patio Private Pool: No
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Lot Information
Lot Size Acres: 1.2 Lot Description: Level
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Listing Price Information
Listing Price: $850000
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Tax Information
Parcel Number: 1000699 Annual Tax: $10617
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Virtual Tour
Garage Information
Has Garage: Yes Garage Space: 12
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School Information
Elementary School: John LymanJunior High School:Senior High School: Coginchaug Regional -
Location Information
Direction: Baileyville Rd to Way to High St WaterSource: Well
How much is this property worth?
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 30 Cherry Ridge Road, Middlefield, CT, 06455 | $749,900 | 4 | 4 | 2,526 | 2,526 SqFt |
| 29 Jackson Hill Road, Middlefield, CT, 06455 | $750,000 | 4 | 5 | 4,718 | 4,718 SqFt |
| 46 Powder Hill Road, Middlefield, CT, 06455 | $625,000 | 3 | 2 | 2,150 | 2,150 SqFt |
| 88 Powder Hill Road, Middlefield, CT, 06455 | $749,900 | 4 | 3 | 2,458 | 2,458 SqFt |
| 123 Way Road, Middlefield, CT, 06455 | $729,999 | 3 | 3 | 2,278 | 2,278 SqFt |
| 18-A Lake Shore Drive, Middlefield, CT, 06455 | $600,000 | 2 | 1 | 961 | 961 SqFt |
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ByOwner last updated this listing 08/20/2026 @ 00:22
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