5385 Main Street, Trumbull, CT 06611
Property image
Property image
UNDER CONTRACT
3D VIEW
0.84 ACRES

$699,000

  • 6 Beds
  • 3.5 Baths
  • 3,397 sqft (on 0.84 acres)

5385 Main Street, Trumbull, CT 06611

Est. Mortgage $4,660/mo*
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Home Highlights

Single-Family Home
Built in 1806
0.84 acre lot
$206/sqft
Garage

Local Information

  • Map ViewExplore the area around 5385 Main Street.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 4 hours ago
Listing courtesy of Michael DeBiase, (203) 209-9142
Keller Williams Realty, (203) 209-9142
Source: Smart MLS, MLS#24165858
Also Listed on Smart MLS.

Home Details for 5385 Main Street

Interior Features

Interior Details
Basement: Partial,UnfinishedNumber of Rooms: 12Types of Rooms: Master Bedroom, Bedroom, Den, Dining Room, Kitchen, Library, Living Room
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3397 Square Feet
Appliances & Utilities
Appliances: Gas Cooktop, Gas Range, Microwave, Refrigerator, Dishwasher, Water HeaterDishwasherLaundry: Upper Level,Mud RoomMicrowaveRefrigerator
Heating & Cooling
Heating: Hot Water,Oil,PropaneHas CoolingAir Conditioning: Attic Fan,Window Unit(s)Has HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckFencing: PartialFoundation: StoneNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageParking Spaces: 3Parking: Detached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3397 Square Feet

Days on Market

Days on Market: 147

Property Information

Year Built
Year Built: 1806
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 393773

Price & Status

Price
List Price: $699,000Price Per Sqft: $206
Status Change & Dates
Off Market Date: Thu Jul 16 2026Possession Timing: Tbd

Active Status

MLS Status: Under Contract

Media

Location

Direction & Address
City: TrumbullCommunity: Long Hill
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Agent Information

Listing Agent
Listing ID: 24165858

Building

Building Area
Building Area: 3397 Square Feet

Community

Community Features: Library, Park, Playground, Shopping/Mall
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.84 acres

Miscellaneous

BasementMls Number: 24165858Zillow Contingency Status: Under ContractAttic: Storage, Partially Finished, Walk-upAttribution Contact: (203) 209-9142Above Grade Unfinished Area: 3397

Additional Information

LibraryParkPlaygroundShopping/Mall

Around this home

What Locals Say about Trumbull

At least 235 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 86 % Say parking is easy

  • 85 % Say it's dog friendly

  • 82 % Say yards are well-kept

  • 77 % Say there's holiday spirit

  • 72 % Say there's wildlife

  • 66 % Say kids play outside

  • 66 % Say it's quiet

  • 65 % Say people would walk alone at night

  • 63 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 37 % Say streets are well-lit

  • 33 % Say there are sidewalks

  • 32 % Say there are community events

  • 29 % Say it's walkable to restaurants

  • 28 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Excellent schools, kid friendly town, swimming pools, plenty of parks and trails, quiet and clean area. "
    0
    Flag
  • Emily.stumph
    "The parks are great but there is no safe way to bike between them, you need a car to enjoy Trumbull’s nature "
    0
    Flag
  • Mjconstructionpro
    "Yes I do see people walking with their dogs, I love my neighbors. People are so nice… Trumbull is the town for me "
    0
    Flag
  • E Rocco
    "not bad. trumbull is nice and close to the merit. i grew up here and wouldn’t change a thing! its a safe and friendly town"
    0
    Flag
  • Xgv8mhqqpg
    "My commute is short with easy access to highway systems. Very little traffic lights and I am only limited by stop signs. Cars are on the road are friendly. "
    0
    Flag
  • Trulia User
    "The area is quiet and family oriented. Neighbors look out for neighbors to keep the peace and order. Nice park with playground area and sports events next to a nice library "
    0
    Flag
  • RMV
    "There are many young families and parks all over town. I live around the corner from the entrance of a walking trail that leads into a park that’s great for a hike or recreation. There are not many restaurants on my side of town except a wine bar, but Starbucks and Dunkin Donuts are walking distance."
    11
    Flag
  • Nicole D.
    "dog friendly area. plenty of state parks and trails for the dogs. just watch out for wildlife with the smaller dogs."
    1
    Flag
  • Jnapoli2521
    "I live in Trumbull Town Commons and some dog owners do not pick up after their dog despite the signs "
    2
    Flag
  • Msvindland
    "Town movies, town pools and block parties. They have a wonderful walking trail that my dog and I use frequently and a wonderful dog park. They have the Trumbull mall which is very well maintained and the movie theater that has security"
    5
    Flag
  • Rebeccalore
    "There are a lot of dogs in the neighborhood and they are well cared for. There is also a good dog park near by. "
    1
    Flag
  • Ashley U.
    "My neighborhood is almost perfect. The only problem is that everything is spaced out. The mall is in one direction, the movie theater in another and the small shops and such are all about. It’s quite boring here if you ask me. "
    9
    Flag
  • KMM
    "I’ve grown up/lived here for 25 years. Amazing town to grow up in! School system is great too. People are friendly and it feels like home."
    2
    Flag
  • Bruce S.
    "We have lived here for more than 50 years. I would never want to move. Beautiful year round, near nice beaches, excellent schools, safe neighborhoods and reasonably affordable. "
    6
    Flag
  • Heather Uva
    "Trumbull is very blue collar down to earth people.. we are friendly, nonjudgemental, who work hard, and love our children. It is a pleasure to live here. Trumbull is close to major highway also for quick ride to the major cities around her."
    2
    Flag
  • Olgui L.
    "Great school system. Very safe town. I have lived here for 42 years, have never had any bad experiences. "
    2
    Flag
  • KB
    "It’s a great residential neighborhood, however there aren’t a ton of options for restaurants in the city itself, however it is really close to surrounding towns with plenty of life."
    0
    Flag
  • Mike s.
    "You can get a fair amount of property that you can expand upon. Even though it’s a double yellow I feel safe when my little ones are playing. "
    1
    Flag
  • Adeliofpimenta
    "I love living here because of the neiborhoods are very nice , and quiet my kids can save ride a bike , and enjoy the weather outside with the beautiful parks around ! "
    0
    Flag
  • Mike s.
    "The school system is trumbull is amazing. Both of our boys are thriving thanks to TECEC. There are also some private school options which we have taken advantage of and have not been disappointed. "
    0
    Flag
  • Lsosa2007
    "This neighborhood is unique because of all the nice people that make it a neighborhood. All the fun things that happen in my neighborhood bring us together."
    1
    Flag
  • Tobiascarling
    "I’ve lived here for eight years and cherish the warm, friendly neighborhood. People are constantly out walking or running, kids playing, and neighbors are chatty."
    0
    Flag
  • Loveeherrr
    "It’s a gated community, everyone is friendly . There’s a gym, pool area, cookout area, guest lounge. You need a key to get in and there’s security that do hourly walks through the neighborhood to keep an eye for anything "
    0
    Flag
  • Tobiascarling
    "We have a very friendly neighborhood, full of families and empty nesters. I love being close to the Merritt, playgrounds, the Trumbull mall, and the grocery store."
    0
    Flag

Market trends in Trumbull

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$665K
$11.67KMoM
Sale-to-List Price
103.7%
Price per sq ft
$320
$12MoM
Available listings
83
5MoM

Home Value

Trulia Estimate
$685K
Since last month
Increased$3K (+0.5%)
Since last year
Decreased$17K (-2.5%)
Since last sale
Increased$35K (+5.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +53% in the last 10 years
MonthEstimated value
2026
August 2026$685K
August 2026$683K
July 2026$682K
June 2026$691K
May 2026$702K
April 2026$708K
March 2026$746K
February 2026$824K
January 2026$821K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
81 Plymouth Avenue, Trumbull, CT
0.26
Single-Family Home
$875,000
11/20/25
5
3.5
2,883
58 Colony Avenue, Trumbull, CT
0.12
Single-Family Home
$730,000
07/24/26
4
2.5
2,174
94 Grove Street, Trumbull, CT
0.22
Single-Family Home
$855,000
05/01/26
4
2.5
3,122
85 Canterbury Lane, Trumbull, CT
0.42
Single-Family Home
$822,000
07/31/26
4
3
3,800
2 Fairchild Circle, Trumbull, CT
0.43
Single-Family Home
$925,000
11/07/25
4
3.5
3,374
26 Grove Street, Trumbull, CT
0.11
Single-Family Home
$639,900
06/05/26
4
2.5
1,753
5338 Main Street, Trumbull, CT
0.09
Single-Family Home
$555,000
09/17/25
3
1.5
1,658
78 Chestnut Hill Road, Trumbull, CT
0.40
Single-Family Home
$835,000
08/25/26
4
2.5
3,121
4293 Madison Avenue, Trumbull, CT
0.56
Single-Family Home
$655,000
12/15/25
4
2.5
1,886
8 Koger Road, Trumbull, CT
0.46
Single-Family Home
$701,000
05/18/26
4
3
2,964

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5338 Main Street, Trumbull, CT 06611
0.09
$630,500
3
1.5
1,658
Off Market
44 Rosemond Terrace, Trumbull, CT 06611
0.13
$575,800
4
2
1,620
Off Market
58 Colony Avenue, Trumbull, CT 06611
0.12
$730,000
4
2.5
2,174
Recently Sold
5418 Main Street, Trumbull, CT 06611
0.08
$651,600
3
2
1,820
Off Market
19 Wilmot Avenue, Trumbull, CT 06611
0.09
$599,000
3
2
1,478
Off Market
5419 Main Street, Trumbull, CT 06611
0.08
$721,900
4
2.5
2,656
Off Market
59 Springwood Drive, Trumbull, CT 06611
0.09
$580,000
3
2
1,760
For Sale
610 Garden Street, Trumbull, CT 06611
0.12
$791,600
4
2.5
2,438
Off Market
26 Grove Street, Trumbull, CT 06611
0.11
$639,900
4
2.5
1,753
Recently Sold
56 Inwood Road, Trumbull, CT 06611
0.13
$543,200
3
1
1,510
Off Market
53 Grove Street, Trumbull, CT 06611
0.17
$536,700
3
2
1,569
Off Market
25 Plymouth Avenue, Trumbull, CT 06611
0.23
$725,000
3
2
2,287
Recently Sold

Price and Tax history

DateEventPrice
Aug 19, 2026
Source: Smart MLS #24165858
Pending
$699,000
Apr 9, 2026
Source: Smart MLS #24165858
Listed For Sale
$699,000
Apr 9, 2026
Source: Smart MLS #24152666
ListingRemoved
$725,000
Mar 13, 2026
Source: Smart MLS #24152666
Listed For Sale
$725,000
Apr 30, 2024
Source: Smart MLS #170591447
Sold
$650,000

LGBTQ Local Legal Protections

Michael DeBiase, Keller Williams Realty, (203) 209-9142
Agent Phone: (203) 209-9142
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 5385 Main Street

  • What is the estimated monthly payment for 5385 Main Street?
    Based on a $699,000 list price with 20% down at today's rates, the estimated monthly payment for 5385 Main Street in Trumbull, CT is approximately $4,737 (about $3,678 principal & interest, $984 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 5385 Main Street compare to homes in Trumbull?
    5385 Main Street in Trumbull, CT is listed at $699,000, about 5% above the $665K median sale price in Trumbull.
  • What do residents say about Trumbull?
    Residents describe Trumbull, CT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See homes for sale in Trumbull, CT.
  • What are the closest schools to 5385 Main Street?
    The closest schools to 5385 Main Street in Trumbull, CT are Frenchtown Elementary (rated 9/10), Madison Middle School (rated 8/10), Trumbull High School (rated 10/10).
  • Does 5385 Main Street have air conditioning?
    Yes, 5385 Main Street in Trumbull, CT has air conditioning.
  • Does 5385 Main Street have laundry facilities?
    Yes, 5385 Main Street in Trumbull, CT has laundry facilities.
5385 Main Street, Trumbull, CT 06611 is a 6 bedroom, 4 bathroom, 3,397 sqft single-family home built in 1806. This property is currently available for sale and was listed by Smart MLS on Apr 9, 2026. The MLS # for this home is MLS# 24165858.