Skip to main content

5385 Main Street

Trumbull, Connecticut 06611

PENDING$699,000
Beds
6
Baths
3 | 1
SqFt
3,397
Acres
0.84
Year Built
1806
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
3-Car Garage3 FireplacesVirtual Tour

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,777

per 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

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

Listed By

Michael DeBiase

(203) 209-9142

Keller Williams Realty

(203) 429-4020

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.