21 Bailey Ave, Darien, CT 06820
OFF MARKET

$1,636,300

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,116 sqft

21 Bailey Ave, Darien, CT 06820

Downtown
Est. Refi. Payment $10,705/mo*
Refinance Your Home
Currently Off Market - Sold Jun 13, 2000 for $565,000

Home Value

Trulia Estimate
$1.64M
Since last month
$100 (0%)
Since last year
Increased$124K (+8.2%)
Since last sale
Increased$1M (+189.5%)
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$1.64M
July 2026$1.64M
June 2026$1.65M
May 2026$1.63M
April 2026$1.58M
March 2026$1.59M
February 2026$1.53M
January 2026$1.5M
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
128 West Avenue, Darien, CT
0.30
Single-Family Home
$1,125,000
01/08/26
3
3
1,636
2 Robin Hood Ln, Darien, CT
0.30
Single-Family Home
$1,400,000
09/17/25
4
3
1,568
71 West Avenue, Darien, CT
0.06
Single-Family Home
$2,350,000
09/30/25
5
4.5
3,780
3 Rocaton Road, Darien, CT
0.22
Single-Family Home
$2,950,000
08/03/26
4
3.5
3,354
3 Andrews Drive, Darien, CT
0.45
Single-Family Home
$1,675,000
09/17/25
4
3
2,724
45 Hecker Avenue, Darien, CT
0.58
Single-Family Home
$1,050,000
12/23/25
5
2
2,844
109 West Avenue, Darien, CT
0.19
Single-Family Home
$2,050,000
09/05/25
5
4.5
3,591
25 Lakeside Avenue, Darien, CT
0.25
Single-Family Home
$1,700,000
06/17/26
2
1.5
1,292
64 Old Kings Highway South, Darien, CT
0.37
Single-Family Home
$1,135,000
10/08/25
5
3.5
3,327
33 Fairview Avenue, Darien, CT
0.56
Single-Family Home
$3,300,000
06/12/26
4
2.5
3,102

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
71 West Avenue, Darien, CT 06820
0.06
-
5
4.5
3,780
Off Market
74 West Avenue, Darien, CT 06820
0.09
$2,937,300
4
4
5,456
Off Market
4 Old Stone Road, Darien, CT 06820
0.11
-
3
2
1,550
Off Market
86 West Avenue, Darien, CT 06820
0.14
$2,153,500
5
3.5
3,266
Off Market
33 Hale Lane #33, Darien, CT 06820
0.17
-
1
1.5
900
Off Market
28 Rocaton Road, Darien, CT 06820
0.18
-
5
4
4,490
Off Market
39 Hale Lane #39, Darien, CT 06820
0.17
$783,800
1
1.5
900
Off Market
6 Stony Brook Road, Darien, CT 06820
0.18
$2,727,300
4
3.5
3,221
Off Market
43 Hale Lane #43, Darien, CT 06820
0.17
$1,384,300
2
2.5
1,800
Off Market
51 Hale Lane #51, Darien, CT 06820
0.18
$625,000
1
1.5
900
Recently Sold
107 Leroy Avenue, Darien, CT 06820
0.21
-
3
2.5
2,856
Off Market
3 Hale Lane #3, Darien, CT 06820
0.20
$822,300
1
1.5
900
Off Market

Local Information

  • Map ViewExplore the area around 21 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
1996
Living Area
2,116 sqft
Price/Sqft
$773
Parking
Garage

About this House

This single-family home is located at 21 Bailey Ave, Darien, CT. 21 Bailey Ave is in the Downtown neighborhood in Darien, CT and in ZIP code 06820. This property has 4 bedrooms, 3 bathrooms and approximately 2,116 sqft of floor space. This property has a lot size of 9147 sqft and was built in 1996.
21 Bailey Ave, Darien, CT 06820 is a 4 bedroom, 3 bathroom, 2,116 sqft single-family home in Downtown, built in 1996. It last sold for $565,000 on Jun 13, 2000. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,636,300, with a rent estimate of $6,703/month.

Home Details for 21 Bailey Ave

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 9147 sqft

Price and Tax history

DateEventPrice
Jun 13, 2000
Source: N/A
Sold
$565,000
Jun 16, 1997
Source: N/A
Sold
$422,000

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 21 Bailey Ave

  • What is 21 Bailey Ave estimated to be worth?
    Trulia's estimated value for 21 Bailey Ave in Darien, CT is $1,636,300.
  • What is the price history for 21 Bailey Ave?
    21 Bailey Ave in Darien, CT last sold for $565,000 in June 2000.
  • 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.
  • How big is the lot at 21 Bailey Ave?
    The lot at 21 Bailey Ave in Darien, CT is about 0.21 acres (9,147 sq ft).
  • Does 21 Bailey Ave have a garage?
    Yes, 21 Bailey Ave in Darien, CT has a garage.

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Apartments for Rent

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Off Market Homes Near 21 Bailey Ave

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Homes for sale near 21 Bailey Ave

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