Skip to main content

8 Dillon Road

Woodbridge, Connecticut 06525

ACTIVE$795,000
Beds
3
Baths
2 | 1
SqFt
4,637
Acres
1.50
Year Built
1750
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
Pool2-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,525

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Mark Fagan

Emerald Glen Associates

(203) 305-8640

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.