27 Bailey Ave, Darien, CT 06820
Property image
Property image
OFF MARKET

$2,137,400

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

27 Bailey Ave, Darien, CT 06820

Downtown
Est. Refi. Payment $14,006/mo*
Refinance Your Home
Currently Off Market - Sold Jun 4, 2021 for $1,451,000

Home Value

Trulia Estimate
$2.14M
Since last month
Decreased$17K (-0.8%)
Since last year
Increased$163K (+8.3%)
Since last sale
Increased$683K (+47.1%)
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 +75% in the last 10 years
MonthEstimated value
2026
August 2026$2.13M
July 2026$2.15M
June 2026$2.16M
May 2026$2.13M
April 2026$2.11M
March 2026$2.1M
February 2026$2M
January 2026$2M
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
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
3 Rocaton Road, Darien, CT
0.26
Single-Family Home
$2,950,000
08/03/26
4
3.5
3,354
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
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
21 Fairfield Avenue, Darien, CT
0.64
Single-Family Home
$2,446,000
06/24/26
4
3.5
3,147
130 West Avenue, Darien, CT
0.23
Single-Family Home
$2,800,000
12/31/25
6
5.5
6,794
45 Hecker Avenue, Darien, CT
0.55
Single-Family Home
$1,050,000
12/23/25
5
2
2,844

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
86 West Avenue, Darien, CT 06820
0.10
$2,166,000
5
3.5
3,266
Off Market
109 West Avenue, Darien, CT 06820
0.12
$2,206,400
5
4.5
3,591
Off Market
6 Stony Brook Road, Darien, CT 06820
0.13
$2,739,700
4
3.5
3,221
Off Market
71 West Avenue, Darien, CT 06820
0.11
$2,526,100
5
4.5
3,780
Off Market
74 West Avenue, Darien, CT 06820
0.12
$2,954,500
4
4
5,456
Off Market
10 Stony Brook Rd, Darien, CT 06820
0.16
$5,660,000
6
7.5
8,680
Recently Sold
51 Hale Lane #51, Darien, CT 06820
0.15
$625,000
1
1.5
900
Recently Sold
43 Hale Lane #43, Darien, CT 06820
0.16
$1,384,300
2
2.5
1,800
Off Market
55 Hale Lane, Darien, CT 06820
0.16
$1,413,500
2
2.5
1,460
Off Market
39 Hale Lane #39, Darien, CT 06820
0.16
$783,900
1
1.5
900
Off Market
28 Rocaton Road, Darien, CT 06820
0.18
$3,944,700
5
4
4,490
Off Market
33 Hale Lane #33, Darien, CT 06820
0.17
$814,700
1
1.5
900
Off Market

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
1997
Lot Size
0.3 acres
Living Area
3,200 sqft
Price/Sqft
$668
Parking
Garage

About this House

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.
27 Bailey Ave, Darien, CT 06820 is a 5 bedroom, 4 bathroom, 3,200 sqft single-family home in Downtown, built in 1997. It last sold for $1,451,000 on Jun 4, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,137,400, with a rent estimate of $7,527/month.

Home Details for 27 Bailey Ave

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Recreation RoomWet BarCeiling Fan
Heating & Cooling
Heating: Oil, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Oil
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 and Tax history

DateEventPrice
Jun 4, 2021
Source: Smart MLS #170376545
Sold
$1,451,000
Mar 23, 2021
Source: Smart MLS #170376545
Contingent
$1,395,000
Mar 10, 2021
Source: Smart MLS #170376545
Listed For Sale
$1,395,000
Jul 24, 2000
Source: N/A
Sold
$720,000
Aug 29, 1997
Source: N/A
Sold
$535,000

Market trends in Darien

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.98M
$246KMoM
Sale-to-List Price
108.9%
3.3%MoM
Price per sq ft
$800
$12MoM
Available listings
36
18MoM

Around this home

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

Frequently asked questions about 27 Bailey Ave

  • What is 27 Bailey Ave estimated to be worth?
    Trulia's estimated value for 27 Bailey Ave in Darien, CT is $2,137,400.
  • What is the price history for 27 Bailey Ave?
    27 Bailey Ave in Darien, CT last sold for $1,451,000 in June 2021.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Darien?
    The median sale price in Darien is $2.98M. That is up $246K from the prior month.
  • Does 27 Bailey Ave have air conditioning?
    Yes, 27 Bailey Ave in Darien, CT has air conditioning.
  • Does 27 Bailey Ave have laundry facilities?
    Yes, 27 Bailey Ave in Darien, CT has in-unit laundry.

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Apartments for Rent

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Off Market Homes Near 27 Bailey Ave

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