27 Bailey St, Trumbull, CT 06611
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Property image
OFF MARKET

27 Bailey St
Trumbull, CT 06611

  • 4 Beds
  • 2.5 Baths
  • 3,468 sqft (on 0.25 acres)

$917,700

Trulia Estimate
as of Jul 20, 2026
Est. Refi. Payment $6,003/mo*
Refinance Your Home

$917,700

Trulia Estimate
as of Jul 20, 2026
Est. Refi. Payment $6,003/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,468 sqft
(on 0.25 acres)

Local Information

  • Map ViewExplore the area around 27 Bailey St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Everything you are looking for and more! Move right into this meticulously maintained 4 bedroom 2.5 bath colonial in a wonderful, sought after neighborhood, on a cul-de-sac in Trumbull. Built in 2000, this amazing home has over 3000 square feet of living space, an open floor plan and central air conditioning. The beautifully updated kitchen has granite countertops, stainless steel appliances and newly finished hardwood floors. The kitchen overlooks a gorgeous family room with cathedral ceilings and sliders leading to wood deck. The layout of the first floor flows beautifully and is perfect for entertaining guests; including a dining room with chair rails and crown molding, as well as a sun-filled, spacious living room. The second floor includes, a large master bedroom with an updated master bath, spa tub and walk in closet; generously- sized bedrooms and laundry area. Additional features include, two-zone heating/cooling, recessed lighting through-out home, finished basement, 2 car attached garage, private backyard and energy efficient solar panels. In an award-winning school district, conveniently located, close to parks, restaurants, biking/walking trail, and shopping malls, this home is a true GEM!
27 Bailey St, Trumbull, CT 06611 is a 4 bedroom, 3 bathroom, 3,468 sqft single-family home built in 2000. It last sold for $630,000 on Jun 30, 2021. It is currently off market. The Trulia Estimate is $917,700, with a rent estimate of $4,393/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 27 Bailey St

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: OtherPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 10890 sqft

Price History for 27 Bailey St

DatePriceEventSource
06/30/2021$630,000Sold
Smart MLS #170386299
04/19/2021$629,900ContingentSmart MLS #170386299
04/08/2021$629,900Listed For SaleSmart MLS #170386299
06/28/2019$470,000Sold
Smart MLS #170176735
04/19/2019$478,000PriceChange
Agent Provided
04/10/2019$485,000PriceChange
Agent Provided
03/28/2019$499,999Listed For SaleAgent Provided
03/25/2010$579,000ListingRemovedAgent Provided
03/14/2010$579,000Listed For SaleAgent Provided
10/27/2000$359,900Sold
Smart MLS #98076211

Market trends in Trumbull

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$653K
Sale-to-List Price
103.8%
Price per sq ft
$309
Available listings
88
14MoM
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Property Tax and Assessment

Year2025
Tax$14,160
Assessment$383,530
Home facts updated by county records

Comparable Sales for 27 Bailey St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
8 Bailey Street, Trumbull, CT
0.10
Single-Family Home
$650,000
09/05/25
4
3
2,143
5 Arrowhead Road, Trumbull, CT
0.16
Single-Family Home
$815,000
06/30/26
4
2.5
2,230
26 Craig Lane, Trumbull, CT
0.10
Single-Family Home
$605,000
06/15/26
3
1.5
1,395
10 Gibson Avenue, Trumbull, CT
0.26
Single-Family Home
$675,000
07/31/25
3
2
2,524
94 Grove Street, Trumbull, CT
0.47
Single-Family Home
$855,000
05/01/26
4
2.5
3,122
4 Woodridge Circle, Trumbull, CT
0.39
Single-Family Home
$676,000
05/06/26
3
1.5
2,255
8 Koger Road, Trumbull, CT
0.57
Single-Family Home
$701,000
05/18/26
4
3
2,964
101 Grove St, Trumbull, CT
0.47
Single-Family Home
$595,000
05/04/26
3
1.5
2,249
30 Windy Ridge, Trumbull, CT
0.40
Single-Family Home
$831,000
03/23/26
3
2.5
2,259
36 Craig Lane, Trumbull, CT
0.10
Single-Family Home
$566,000
01/30/26
3
1
1,526

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Bailey St.
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.

  • 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

  • 31 % 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 27 Bailey St

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Off Market Homes Near 27 Bailey St

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