89 John Perry Road, Eastford, CT 06242 - Photo 1

1/1

$575,000

Sold
Closed
Single Family
4 Beds
2 Full Baths
1 Partial Bath
4,538 Sq. Ft.
Updated 8 days ago

1/1

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.

Full Property Details

Full Property Details for 89 John Perry Rd

General

Sold For: $575,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24099024
Added to Site: 370 day(s) ago

Interior

Number of Rooms: 8
Rooms/Areas: Laundry Room, Mud Room, Roughed-In Bath, Sitting Room, Workshop
Interior Features: Cable - Available, Elevator
Fireplace: Yes
Number of Fireplaces: 1
Appliances: Refrigerator

Rooms

Bathrooms

Total Bathrooms: 3
Full Bathrooms: 2
Half Bathrooms: 1

Bedrooms

Total Bedrooms: 4
Primary Bedroom: Primary Bedroom - Fireplace, Full Bath, Wide Board Floor, 14.8 x 17.5, Upper
Bedroom 1: Bedroom - Fireplace, Wide Board Floor, 14.7 x 12.2, Upper
Bedroom 2: Bedroom - Fireplace, Wide Board Floor, 14.7 x 13.5, Upper
Bedroom 3: Bedroom - Wide Board Floor, 14.9 x 9.1, Upper

Other Rooms

Living Room: Living Room - Fireplace, Wide Board Floor, 14.11 x 17.3, Main
Kitchen: Kitchen - Built-Ins, Fireplace, Half Bath, Laundry Hookup, Wide Board Floor, 17.1 x 13.3, Main
Dining Room: Dining Room - Book Shelves, Built-In Hutch, Fireplace, Wide Board Floor, 14.11 x 22.9, Main
Office: Office - Wide Board Floor, 14.7 x 9.1, Upper
Den: Den - Fireplace, Wide Board Floor, 12.8 x 13.8, Main
Laundry: Main Level
Other Room 1: Other - Palladian Window(s), Wide Board Floor, 9.8 x 19.1, Main
Other Room 2: Other - Built-Ins, Fireplace, Wide Board Floor, 19.11 x 20.6, Upper

Exterior

Exterior Features: Porch-Screened, Porch
Color: Yellow

Location

County: Windham
Driving Directions: gps

School Information

Elementary School: Eastford
High School: Woodstock Academy

Heating & Cooling

Cooling Type: None
Heating Type: Hot Water, Radiant, Oil
Heating Fuel: Oil
Water Heater: Oil, Domestic

Utilities

Sewer: Septic
Water: Private Well

Structural Information

Architectural Style: Colonial
Construction Status: No/Resale
Exterior Const.: Clapboard
Basement Desc.: Full
Roof: Asphalt Shingle
Attic: Yes
Square Feet: 4,538
Above Ground: 4,538 Sq. Ft.
Year Built: 1800

Lot Features

Lot Size (Acres): 3
Zoning: Res
Lot Description: Sloping Lot

Financial Considerations

Assessment Amount: $303,800
Tax Year: July 2025-June 2026

Disclosures and Reports

Exclusions: corner hutch in front tea room
Property ID: 1683630

Listed by Berkshire Hathaway NE Prop., Mary Collins
Sold by Berkshire Hathaway NE Prop., Kristen Kaskela

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Listing agent

— 89 John Perry Rd —

Mary Collins

Berkshire Hathaway NE Prop.

Agent Contact: (860) 336-6677 Office Contact: (860) 928-1995

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NMLS#: 1598647

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Schools

Schools serving 89 John Perry Rd

School District:Eastford School District

Name	Grades	Distance
Eastford Elementary School 12 Westford Road, Eastford, CT 06242	PK-8	0.2 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 89 John Perry Rd

Date

Details

Price

Change

Source

5/26/2026

Sold

$575,000

—

MLS

6/07/2025

Listed

$575,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

150 Krapf Rd, Ashford, CT 06278 - Photo 1

Just Listed

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150 Krapf Rd Ashford, CT 06278

Single Family
Active
Updated 21 hours ago

4
Beds
2
Total Baths
1,648
Sq. Ft.

Listed by Raphael Vergnaud (860) 500-3525

186 Brickyard Rd, Woodstock Valley, CT 06281 - Photo 1

Just Listed

$589,000

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Single Family
Active
Updated 2 days ago

3
Beds
2
Total Baths
1,970
Sq. Ft.

Listed by Pine Knoll Real Estate

608 English Neighborhood Rd, Woodstock Valley, CT 06281 - Photo 1

Just Listed

$440,000

Open House

608 English Neighborhood Rd Woodstock Valley, CT 06281

Single Family
Active
Updated 3 hours ago

4
Beds
4
Total Baths
1,728
Sq. Ft.

Listed by Real Broker CT, LLC

133 Route 198, Woodstock Valley, CT 06282 - Photo 1

Just Listed

$349,900

Open House

133 Route 198 Woodstock Valley, CT 06282

Single Family
Active
Updated 2 days ago

2
Beds
2
Total Baths
1,894
Sq. Ft.

Listed by RE/MAX Bell Park Realty

101 Child Hill Rd, Woodstock Valley, CT 06281 - Photo 1

101 Child Hill Rd Woodstock Valley, CT 06281

Single Family
Active
Updated 6 days ago

4
Beds
3
Total Baths
2,150
Sq. Ft.

Listed by Berkshire Hathaway NE Prop.

69 Meadowside Rd, Woodstock Valley, CT 06281 - Photo 1

Price Reduced

-$10,000 (-11.76%)

$75,000

69 Meadowside Rd Woodstock Valley, CT 06281

Mobile Home
Active
Updated 4 days ago

2
Beds
1
Total Bath
592
Sq. Ft.

Listed by RE/MAX One

1250 Route 171, Woodstock Valley, CT 06281 - Photo 1

Price Reduced

-$7,500 (-2.65%)

$275,000

1250 Route 171 Woodstock Valley, CT 06281

Single Family
Active
Updated 3 days ago

3
Beds
2
Total Baths
1,640
Sq. Ft.

Listed by First Choice Realty

863 Route 198, Woodstock Valley, CT 06281 - Photo 1

863 Route 198 Woodstock Valley, CT 06281

Single Family
Active
Updated 21 hours ago

3
Beds
3
Total Baths
2,672
Sq. Ft.

Listed by RE/MAX Bell Park Realty

86A County Rd, Eastford, CT 06242 - Photo 1

Sold

$580,000

86A County Rd Eastford, CT 06242

Single Family
Closed

3
Beds
3
Total Baths
1,672
Sq. Ft.

Listed by Brunet and Company Real Estate
Sold by Coldwell Banker Realty

16 Pilfershire Rd, Eastford, CT 06242 - Photo 1

Sold

$575,000

16 Pilfershire Rd Eastford, CT 06242

Single Family
Closed

3
Beds
3
Total Baths
2,854
Sq. Ft.

Listed by Berkshire Hathaway NE Prop.
Sold by Berkshire Hathaway NE Prop.

698 Brayman Hollow Rd, Pomfret, CT 06259 - Photo 1

Sold

$515,000

698 Brayman Hollow Rd Pomfret, CT 06259

Single Family
Closed

4
Beds
3
Total Baths
2,364
Sq. Ft.

Listed by CR Premier Properties
Sold by Signature Properties of NewEng

23 Little Bunggee Hill Rd, Woodstock Valley, CT 06282 - Photo 1

Sold

$559,000

23 Little Bunggee Hill Rd Woodstock Valley, CT 06282

Single Family
Closed

4
Beds
2
Total Baths
2,160
Sq. Ft.

Listed by Signature Properties of NewEng
Sold by CR Premier Properties

89 John Perry Road, Eastford, CT 06242 (MLS# 24099024) is a Single Family property that was sold at $575,000 on May 26, 2026. Want to learn more about 89 John Perry Road? Do you have questions about finding other Single Family real estate for sale in Eastford? You can browse all Eastford real estate or contact a Coldwell Banker agent to request more information.

89 John Perry Rd Eastford, CT 06242