$995,000

40 Plaster House Road, Southbury, CT 06488

4 beds |
2 baths |
2,877 sqft

Single-Family Home
Built in 1800
3.21acre lot
2 car garage
$346/sqft
Listed 1 month ago

Property Description

Welcome to Hennessey Farm, where heritage, craftsmanship, and modern living converge. Once a 60-plus-acre working dairy farm, this storied property was thoughtfully subdivided in 1980 and later transformed into a reimagined farmhouse Cape that has been restored, expanded, and elevated for the 21st century. Every inch of this home has been intentionally loved. The current owners approached each enhancement with reverence for the past and an eye toward timeless design. Reclaimed barnwood from the original horse stables now warms the custom kitchen cabinetry, while the solid chestnut front doors, crafted from beams salvaged from the original 1800s structure, announce both history and heart the moment you arrive. A brand-new septic system and a 2025 addition blend seamlessly with the historic envelope. Inside, expanded ceiling heights, natural textures, and an inviting, grounded aesthetic create a true sense of home. Step outside, and the property unfolds into its own private compound. A beautiful detached office, perfect for creative or remote work, adjoins a two-car garage with impressive 14-foot ceilings, an ideal space for collectors, hobbyists, or future expansion. Hennessey Farm is far more than a Cape Cod farmhouse. It is a thoughtfully reimagined heirloom, an 1800s structure renewed for modern life without sacrificing the soul that makes it unforgettable.

Listing Status:: Active
Date Added:: November 20, 2025 at 05:21PM
Listing Office:: Compass Connecticut, LLC : (203) 290-2477
Listing Agent:: Sam Campolo : (914) 584-9799
MLS ID:: 24140686

General: Cable - AvailableSecurity System
Appliances: Oven/RangeRange HoodRefrigeratorDishwasherDryer
Basement: FullUnfinished
A/C: Central Air
Heating: Hot AirOil
Fireplace: Fireplaces: 1

General: Barn
Style: Farm House
Parking: Parking spaces: 2

Roofing: Asphalt Shingle

County: New Haven

Driveway: Private
Zoning: R-601332800

Water: Private Well
Sewer: Septic

This listing courtesy of Sam Campolo, Compass Connecticut, LLC

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Pomperaug School

607 Main St S, Southbury, CT, 06488

Grades KG-5

3.24 miles away

Rochambeau Middle School

100 Peter Rd, Southbury, CT, 06488

Grades 6-8

3.08 miles away

Pomperaug Regional High School

234 Judd Rd, Southbury, CT, 06488

Grades 9-12

3.45 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.