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89 John Perry Road

Eastford, CT 06242
  • $575,000
  • STATUS: Active Under Contract
  • ON SITE: 236 Days
  • MLS #: 24099024
Under Contract
$575,000
  • 4
    BEDS
  • 3
    ACRES
  • 2
    BATHS
  • 1
    1/2 BATHS
  • 4,538
    SQFT
  • $127
    $/SQFT
Type:
Single-Family Home
Built:
1800
County:
Area:

School Information

Elementary School:
High School:

Description

Welcome to the Benjamin Bosworth House, affectionately known locally as "The Castle." This extraordinary Federal-style home, Circa 1796, blends timeless craftsmanship with historic character. Set on 3 private acres, this 4,538 sq ft estate features 4 bedrooms, 2.5 baths, and 11 fireplaces across a thoughtfully designed layout. Notable architectural details include hand-carved mantels, doors, and windows-crafted by a woodworker who lived onsite through a winter. The centerpiece is a rare full-height monitor, originally a Masonic meeting hall, complete with fireplaces and built-in benches. Inside you'll find grand halls, a formal parlor, Dining room with bookcases & original China closet, tea room or keeping room gets afternoon sun, office, Studio, workshop, pantry, and laundry.1/2 bath with original wooden drain board & copper sink, Kitchen has antique basin, custom cherry wood pantry, hand painted stenciled floors. Primary Bed with private shower bathroom, 3 beds & office and full bath finish 2nd floor. Listed on the National Register of Historic Places, this one-of-a-kind home offers the charm of 18th-century design with the potential for modern customization. Own a piece of Connecticut history in peaceful Eastford. The house features a two-story main block topped by a hip roof, with a distinctive full-height monitor section projecting from the center. Benjamin Bosworth, for whom the house was built, was a significant figure in Eastford's history. He served on the building committee of the local Congregational Church and was instrumental in relocating the previous meeting house from the site. His desire for a distinctive residence led to the creation of this unique structure, which has since become a landmark in the area. Today, the Benjamin Bosworth House stands as a testament to early American architecture and the rich history of Eastford, Connecticut.

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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: 2026-01-22T00:09:49.833.
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89 John Perry Road Eastford, CT 06242

  • Price: $575,000
  • Status: Active Under Contract
  • On Site: 236 Days
  • MLS #: 24099024
4
Beds
2
Baths
1
½ Baths
3
Acres
4,538
SQFT
$127
$/SQFT
1800
Built
County:
Windham
Area:
Eastford
Elementary School:
Eastford
High School:
Woodstock Academy
Property Description
Welcome to the Benjamin Bosworth House, affectionately known locally as "The Castle." This extraordinary Federal-style home, Circa 1796, blends timeless craftsmanship with historic character. Set on 3 private acres, this 4,538 sq ft estate features 4 bedrooms, 2.5 baths, and 11 fireplaces across a thoughtfully designed layout. Notable architectural details include hand-carved mantels, doors, and windows-crafted by a woodworker who lived onsite through a winter. The centerpiece is a rare full-height monitor, originally a Masonic meeting hall, complete with fireplaces and built-in benches. Inside you'll find grand halls, a formal parlor, Dining room with bookcases & original China closet, tea room or keeping room gets afternoon sun, office, Studio, workshop, pantry, and laundry.1/2 bath with original wooden drain board & copper sink, Kitchen has antique basin, custom cherry wood pantry, hand painted stenciled floors. Primary Bed with private shower bathroom, 3 beds & office and full bath finish 2nd floor. Listed on the National Register of Historic Places, this one-of-a-kind home offers the charm of 18th-century design with the potential for modern customization. Own a piece of Connecticut history in peaceful Eastford. The house features a two-story main block topped by a hip roof, with a distinctive full-height monitor section projecting from the center. Benjamin Bosworth, for whom the house was built, was a significant figure in Eastford's history. He served on the building committee of the local Congregational Church and was instrumental in relocating the previous meeting house from the site. His desire for a distinctive residence led to the creation of this unique structure, which has since become a landmark in the area. Today, the Benjamin Bosworth House stands as a testament to early American architecture and the rich history of Eastford, Connecticut.
Exterior Features

Color Yellow Direct Waterfront YN No Exterior Features Porch-ScreenedPorch Exterior Siding Clapboard Garage And Parking None Lot Description Sloping Lot Roof Information Asphalt Shingle Style Colonial Swimming Pool YN No Waterfront Description Not Applicable

Interior Features

Appliances Included Refrigerator Attic Description Walk-up Attic YN Yes Basement Description Full Cooling System None Fireplaces Total 1 Heat Type Hot WaterRadiant Interior Features Cable - AvailableElevator Laundry Room Info Main Level Laundry Room Location off kitchen Rooms Bedroom (Upper Level FireplaceWide Board Floor) Other (Main Level Palladian Window(s)Wide Board Floor) Den (Main Level FireplaceWide Board Floor) Other (Upper Level Built-InsFireplaceWide Board Floor) Dining Room (Main Level Book ShelvesBuilt-In HutchFireplaceWide Board Floor) Bedroom (Upper Level Wide Board Floor) Living Room (Main Level FireplaceWide Board Floor) Bedroom (Upper Level FireplaceWide Board Floor) Office (Upper Level Wide Board Floor) Kitchen (Main Leve Rooms Additional Laundry RoomMud RoomRoughed-In BathSitting RoomWorkshop Sq Ft Est Heated Above Grade 4538 Sq Ft Total 4538 Total Rooms 8

Property Features

Agent Owner YN No Bank Owned Property No Exclusions corner hutch in front tea room Foundation Type Stone Fuel Tank Location In Basement Heat Fuel Type Oil Home Owners Assocation No Home Warranty Offered YN No Hot Water Description OilDomestic New Construction Type No/Resale Potential Short Sale No Sewage System Septic Tax Year July 2025-June 2026 Under Agreement Yn No Water Source Private Well Zoning Res

Listing information © 2026 Smart MLS
Listing provided courtesy of Mary Collins of Berkshire Hathaway NE Prop.: (860) 928-1995.


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: 2026-01-22T00:09:49.833.
 
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212 Route 32
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