8 Dillon Road
Woodbridge, Connecticut 06525
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 4,637
- Acres
- 1.50
- Year Built
- 1750
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
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.
Key Facts
- City/Town
- Woodbridge
- Neighborhood
- N/A
- Property / Style
- Single Family · Contemporary
- Year Built
- 1750
- Days on Market
- 49 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 4,637 sq ft
- Lot Size
- 1.50 acres
- Garage / Parking
- 2 garage · 10 total
- Property Taxes
- $14,488 / Annually
Market Snapshot
The Woodbridge Market
Single Family · trailing 12 months
Active Listings
23
18 under contract
Median List Price
$985,000
23 active listings
Median Closed Price
$780,000
89 sales
Median Days on Market
57
23 active listings
Median $ / Sq Ft
$263
23 active listings
Sale-to-List Ratio
100.0%
89 sales
How this home compares
List Price
$795,000
vs $985,000 median
19.3% below median
Price / Sq Ft
$171
vs $263 median
35.0% below median
Days on Market
49 days
vs 57 days median
8 days fresher than median
Based on 23 active and 89 closed sales (trailing 12 mo) of single family in Woodbridge. Source: SmartMLS · As of July 28, 2026.
Location
8 Dillon Road, Woodbridge, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,053
- Property Taxes$1,207
- Insurance$265
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbridge
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 1750
- New Construction
- No/Resale
- Living Area
- 4,637 sq ft
Schools
- Elementary
- Beecher Road
- High
- Amity Regional
Interior
- Heating
- Hot Air
- Heat Fuel
- ElectricPropaneWood
- Cooling
- Window Unit
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Main level
- Appliances
- Electric RangeRefrigerator
- Basement
- FullUnfinishedInterior AccessFull With Walk-Out
- In-Law Apartment
- Possible
- Interior Features
- Cable - AvailableOpen Floor Plan
- Additional Rooms
- Bonus RoomExercise RoomLaundry RoomSitting Room
Exterior & Lot
- Lot Size
- 1.50 acres
- Zoning
- A
- Garage / Parking
- 2 garage spaces10 total parking spacesUnder House GarageOff Street ParkingDrivewayPrivate
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- VinylLap Pool
- Construction
- ShingleStone
- Roof
- Asphalt Shingle
- Foundation
- Masonry
- Exterior Features
- BalconyGazeboWrap Around DeckDeckGarden AreaPatio
- Lot Description
- TreedRolling
Listing & Financials
- Property Taxes
- $14,488 / Annually
- Days on Market
- 49
- MLS #
- 24182465
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 8:02 AM UTC.