27 Bailey Ave, Darien, CT 06820
OFF MARKET

27 Bailey Ave
Darien, CT 06820

Downtown
  • 5 Beds
  • 4 Baths
  • 3,200 sqft (on 0.30 acres)

$2,133,300

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $13,709/mo*
Refinance Your Home

$2,133,300

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $13,709/mo*
Refinance Your Home
5 Beds
4 Baths
3,200 sqft
(on 0.30 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

This single-family home is located at 27 Bailey Ave, Darien, CT. 27 Bailey Ave is in the Downtown neighborhood in Darien, CT and in ZIP code 06820. This property has 5 bedrooms, 4 bathrooms and approximately 3,200 sqft of floor space. This property has a lot size of 0.30 acres and was built in 1997.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

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

Home Details for 27 Bailey Ave

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Recreation RoomWet BarCeiling Fan
Heating & Cooling
Heating: Other, Oil, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Security
Security System

Property Information

Year Built
Year Built: 1997Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.30 acres

Price History for 27 Bailey Ave

DatePriceEventSource
06/04/2021$1,451,000Sold
Smart MLS #170376545
03/23/2021$1,395,000ContingentSmart MLS #170376545
03/10/2021$1,395,000Listed For SaleSmart MLS #170376545
07/24/2000$720,000Sold
N/A
08/29/1997$535,000Sold
N/A
12/05/1996$110,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$16,029
Assessment$1,035,440
Home facts updated by county records

Comparable Sales for 27 Bailey Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
109 West Avenue, Darien, CT
0.12
Single-Family Home
$2,050,000
09/05/25
5
4.5
3,591
71 West Avenue, Darien, CT
0.11
Single-Family Home
$2,350,000
09/30/25
5
4.5
3,780
64 Old Kings Highway South, Darien, CT
0.43
Single-Family Home
$1,135,000
10/08/25
5
3.5
3,327
128 West Avenue, Darien, CT
0.22
Single-Family Home
$1,125,000
01/08/26
3
3
1,636
4 Old Stone Road, Darien, CT
0.16
Single-Family Home
$1,534,500
08/20/25
3
2
1,550
2 Robin Hood Ln, Darien, CT
0.35
Single-Family Home
$1,400,000
09/17/25
4
3
1,568
3 Andrews Drive, Darien, CT
0.49
Single-Family Home
$1,675,000
09/17/25
4
3
2,724
11 Cedar Gate Road, Darien, CT
0.62
Single-Family Home
$1,800,000
08/21/25
4
3
3,023
50 Mansfield Avenue, Darien, CT
0.46
Single-Family Home
$3,000,750
06/30/25
5
3.5
4,376
2 Tanglewood Trail, Darien, CT
0.23
Single-Family Home
$4,500,000
07/16/25
5
4.5
5,338

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Bailey Ave.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Downtown
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Downtown

At least 1 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 100 % Say they plan to stay for at least 5 years

  • 100 % Say there's holiday spirit

  • 100 % Say yards are well-kept

  • 100 % Say it's quiet

  • 100 % Say there's wildlife

  • 100 % Say it's walkable to restaurants

  • 100 % Say car is needed

  • 100 % Say neighbors are friendly

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

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Off Market Homes Near 27 Bailey Ave

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Homes for rent near 27 Bailey Ave

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27 Bailey Ave, Darien, CT 06820 is a 5 bedroom, 4 bathroom, 3,200 sqft single-family home built in 1997. 27 Bailey Ave is located in Downtown, Darien. This property is not currently available for sale. 27 Bailey Ave was last sold on Jun 4, 2021 for $1,451,000. The current Trulia Estimate for 27 Bailey Ave is $2,133,300.