8 Dillon Road, Woodbridge, CT 06525

• 3 beds |
• 3 baths |
• 4,637 sqft

Property Description

One of the Most Unique & Eclectic Homes in Connecticut! Originally built as a barn in 1750, this expansive and delightfully quirky home is truly one-of-a-kind. From the moment you step inside, you'll be captivated by its whimsical character; starting with the once fully functional cement mixer that has been creatively repurposed as a fireplace with pellet stove. Beyond this conversation piece is a cozy sitting area with fireplace, leading to a serene enclosed porch that overlooks the private in-ground lap pool (8x60) surrounded by lush gardens. The dramatic two-story wood beamed living room is accented by a loft that looks down over the space, adding architectural intrigue. Throughout the home, you'll find an array of alcoves, balconies, lofts, nooks, and crannies-each offering unique charm and functionality. Multiple fireplaces, custom built-in lighting, and intricate architectural details-including stained glass windows-make every corner of this home feel like a discovery. The versatile floorplan includes a private primary suite with steam shower and access to balcony. Adjacent office area leading to a loft with half bath and second stairway. A separate suite of additional bedrooms, each on its own level, sharing a bath and a fireplace in the sitting room. Numerous flexible spaces for bedrooms, offices, studios, or quiet retreats. The peaceful setting enjoys tranquil views over a pond surrounded by mature trees and gardens; offering a true sense of privacy and serenity.

Listing Status:

Active

Date Added:

June 9, 2026

Data Last Updated:

June 26, 2026 at 4:50AM

Listing Office:

Emerald Glen Associates : (203) 305-8640

Listing Agent:

Mark Fagan : (203) 305-8640

MLS ID:

24182465

Interior

• General: Cable - AvailableOpen Floor Plan
• Rooms: Bonus RoomExercise RoomLaundry RoomSitting Room
• Appliances: Electric RangeRefrigerator
• Laundry: Main Level
• Basement: FullUnfinishedInterior AccessFull With Walk-Out
• A/C: Window Unit
• Heating: Hot AirElectricPropaneWood
• Fireplace: Fireplaces: 1

Exterior

• General: BalconyGazeboWrap Around DeckDeckGarden AreaPatio
• Style: Contemporary
• Pool: VinylLap Pool
• Parking: Parking spaces: 10

Construction

• Roofing: Asphalt Shingle

Location

• County: New Haven

Lot

• Driveway: Private
• Zoning: A1451355

Utilities

• Water: Private Well
• Sewer: Septic