5385 Main Street, Trumbull, CT 06611
FOR SALE
0.84 ACRES

5385 Main Street
Trumbull, CT 06611

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

$699,000

Est. Mortgage $3,619/mo*
Get Pre-Qualified

$699,000

Est. Mortgage $3,619/mo*
Get Pre-Qualified
6 Beds
3.5 Baths
3,397 sqft
(on 0.84 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
$206
Listed
27 days ago

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: 27

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
Possession Timing: Tbd

Active Status

MLS Status: Active

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: 24165858Attic: Storage, Partially Finished, Walk-upAttribution Contact: (203) 209-9142Above Grade Unfinished Area: 3397

Additional Information

LibraryParkPlaygroundShopping/Mall
Last check for updates: about 8 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.

Price History for 5385 Main Street

DatePriceEventSource
04/09/2026$699,000Listed For SaleSmart MLS #24165858
04/09/2026$725,000ListingRemovedSmart MLS #24152666
03/13/2026$725,000Listed For SaleSmart MLS #24152666
04/30/2024$650,000Sold
Smart MLS #170591447
04/29/2024$699,000PendingSmart MLS #170591447
08/23/2023$699,000Listed For SaleSmart MLS #170591447
09/02/1988$365,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$11,765
Assessment$320,180
Home facts updated by county records

Comparable Sales for 5385 Main Street

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
31 Old Barn Road, Trumbull, CT
0.42
Single-Family Home
$903,000
07/14/25
4
2.5
3,015
3 Paulina Place, Trumbull, CT
0.21
Single-Family Home
$1,000,000
07/08/25
4
3.5
3,215
94 Grove Street, Trumbull, CT
0.22
Single-Family Home
$855,000
05/01/26
4
2.5
3,122
2 Fairchild Circle, Trumbull, CT
0.43
Single-Family Home
$925,000
11/07/25
4
3.5
3,374
5338 Main Street, Trumbull, CT
0.09
Single-Family Home
$555,000
09/17/25
3
1.5
1,658
48 Lafayette Drive, Trumbull, CT
0.52
Single-Family Home
$740,000
08/21/25
4
3.5
3,924
64 Regina Street, Trumbull, CT
0.55
Single-Family Home
$683,000
07/25/25
4
2.5
2,502
9 MacArthur Road, Trumbull, CT
0.65
Single-Family Home
$770,000
05/07/25
5
3
3,142
4293 Madison Avenue, Trumbull, CT
0.56
Single-Family Home
$655,000
12/15/25
4
2.5
1,886

Assigned Schools

These are the assigned schools for 5385 Main Street.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Trumbull

At least 234 Trulia users voted on each feature.

  • 92 % 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

  • 31 % Say there are community events

  • 29 % Say it's walkable to restaurants

  • 28 % Say it's walkable to grocery stores

Learn more about our methodology.
  • 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

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.
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.