8 Dillon Road, Woodbridge, Connecticut

$795,000

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3

Beds

3

Baths

4,637

Square feet

1.50

Acres

About 8 Dillon Road

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.

Features of 8 Dillon Road

MLS® # 24182465
Price $795,000
Bedrooms 3
Bathrooms 3.00
Full Baths 2
Half Baths 1
Square Footage 4,637
Acres 1.50
Type Single Family For Sale
Style Contemporary
Status Active

Community Information

Address 8 Dillon Road
Area N/A
City Woodbridge
County New Haven
State Connecticut
Zip Code 06525

Amenities

Parking Spaces 10
Parking Under House Garage, Off Street Parking, Driveway
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool Yes
Pool Vinyl, Lap Pool

Interior

Interior Features Cable - Available, Open Floor Plan
Appliances Electric Range, Refrigerator
Heating Hot Air, Electric, Propane, Wood
Cooling Window Unit
Fireplace Yes
# of Fireplaces 1
Has Basement Yes
Basement Full, Unfinished, Interior Access, Full With Walk-Out

Exterior

Exterior Shingle, Stone
Exterior Features Balcony, Gazebo, Wrap Around Deck, Deck, Garden Area, Patio
Lot Description Treed, Rolling
Roof Asphalt Shingle
Foundation Masonry

School Information

Elementary Beecher Road
High Amity Regional

Additional Information

Date Listed June 9th, 2026
Days on Market 94
Zoning A
RE / Bank Owned No

Listing Details

OfficeEmerald Glen Associates

Listing Map

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Listing information last updated on September 10th, 2026 at 3:26pm EDT.