5385 Main Street
Trumbull, Connecticut 06611
- Beds
- 6
- Baths
- 3 | 1
- SqFt
- 3,397
- Acres
- 0.84
- Year Built
- 1806
- Neighborhood
- Long Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Magnificent opportunity to embrace historic charm. This spacious Victorian home is filled with character and timeless architectural details while offering the comfort of modern updates. A beautifully updated kitchen with a massive island that blends classic charm with modern convenience. The home's signature wrap-around porch provides the perfect spot to relax and enjoy the outdoors. Inside, the generous formal dining room is ideal for hosting family gatherings and holiday celebrations. Designed with entertaining in mind, the home offers a wonderful flow between indoor and outdoor living spaces. Flexible room layouts allow the home to easily adapt to a variety of needs. With five to six bedrooms, there is plenty of space for a large household, or rooms can be transformed into home offices, guest suites, a gym, or creative studios. Rich in history, the property was originally owned by individuals involved in the early development of the Town of Trumbull, adding a unique story to this special home. Make sure to check out the attic and the "hidden" room. Fully fenced flat yard set back from the street. A gorgeous home you don't want to miss.
Key Facts
- City/Town
- Trumbull
- Neighborhood
- Long Hill
- Property / Style
- Single Family · Colonial
- Year Built
- 1806
- Days on Market
- 110 days
- Beds
- 6
- Baths
- 3 full · 1 half
- Living Area
- 3,397 sq ft
- Lot Size
- 0.84 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $11,765 / Annually
Market Snapshot
The Trumbull Market
Single Family · trailing 12 months
Active Listings
40
61 under contract
Median List Price
$784,450
40 active listings
Median Closed Price
$680,860
322 sales
Median Days on Market
27
40 active listings
Median $ / Sq Ft
$290
40 active listings
Sale-to-List Ratio
102.3%
322 sales
How this home compares
List Price
$699,000
vs $784,450 median
10.9% below median
Price / Sq Ft
$206
vs $290 median
29.0% below median
Days on Market
110 days
vs 27 days median
83 days longer than median
Based on 40 active and 322 closed sales (trailing 12 mo) of single family in Trumbull. Source: SmartMLS · As of July 28, 2026.
Location
5385 Main Street, Trumbull, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,564
- Property Taxes$980
- Insurance$233
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Trumbull
- Neighborhood
- Long Hill
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1806
- New Construction
- No/Resale
- Living Area
- 3,397 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- OilPropane
- Cooling
- Attic FanWindow Unit
- Fireplaces
- 3
- Laundry
- Upper Level
- Appliances
- Gas CooktopGas RangeMicrowaveRefrigeratorDishwasher
- Basement
- PartialUnfinished
- Additional Rooms
- FoyerLaundry RoomMud Room
Exterior & Lot
- Lot Size
- 0.84 acres
- Zoning
- A
- Garage / Parking
- 3 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Wood
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- Deck
- Lot Description
- Fence - PartialLightly WoodedTreedDryLevel Lot
Listing & Financials
- Property Taxes
- $11,765 / Annually
- Days on Market
- 110
- MLS #
- 24165858
- MLS Status
- Under Contract - Continue to Show
Similar Properties
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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 7:01 AM UTC.