556 Middlesex Rd, Darien, CT 06820
Property image
Property image
OFF MARKET

$4,498,400

Trulia Estimate
  • 6 Beds
  • 7 Baths
  • 5,262 sqft (on 2 acres)

556 Middlesex Rd, Darien, CT 06820

Est. Refi. Payment $31,474/mo*
Refinance Your Home
Currently Off Market - Sold Jun 29, 2016 for $2,695,000

Home Value

Trulia Estimate
$4.5M
Since last month
Increased$58K (+1.3%)
Since last year
Increased$771K (+20.5%)
Since last sale
Increased$2M (+68.2%)
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 +74% in the last 10 years
MonthEstimated value
2026
October 2026$4.53M
September 2026$4.5M
August 2026$4.48M
July 2026$4.42M
June 2026$4.52M
May 2026$4.21M
April 2026$4.11M
March 2026$4.17M
February 2026$3.97M
January 2026$3.92M
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
561 Middlesex Road, Darien, CT
0.08
Single-Family Home
$2,800,000
08/10/26
4
3.5
3,411
6 Cloudy Lane, Darien, CT
0.41
Single-Family Home
$4,500,000
05/29/26
5
5
5,864
316 Mansfield Avenue, Darien, CT
0.36
Single-Family Home
$5,625,000
07/24/26
5
6
9,039
19 Blueberry Lane, Darien, CT
0.15
Single-Family Home
$3,711,000
06/03/26
4
2.5
3,881
272 Mansfield Ave, Darien, CT
0.52
Single-Family Home
$5,550,000
08/06/26
6
6
7,496
30 Inwood Road, Darien, CT
0.66
Single-Family Home
$3,850,000
08/12/26
6
6.5
5,113
28 Crooked Mile Road, Darien, CT
0.67
Single-Family Home
$4,315,000
06/11/26
5
6
4,653
451 Mansfield Ave, Darien, CT
0.61
Single-Family Home
$3,380,000
04/13/26
5
6
7,652
21 Fox Hill Ln, Darien, CT
0.57
Single-Family Home
$4,597,500
06/29/26
5
6.5
6,308
5 Wheat Lane, Darien, CT
0.72
Single-Family Home
$3,308,000
04/15/26
5
4
3,509

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
2 Ox Ridge Ln, Darien, CT 06820
0.04
$4,186,200
5
4.5
6,449
Off Market
543 Middlesex Rd, Darien, CT 06820
0.04
$3,755,800
5
5.5
-
Off Market
18 Ox Ridge Ln, Darien, CT 06820
0.07
$3,156,300
5
3.5
3,629
Off Market
9 Blueberry Ln, Darien, CT 06820
0.08
$2,994,100
4
5
4,100
Off Market
525 Middlesex Rd, Darien, CT 06820
0.08
$3,497,700
4
3.5
5,321
Off Market
11 Blueberry Ln, Darien, CT 06820
0.08
$3,477,000
5
5.5
5,436
Off Market
561 Middlesex Road, Darien, CT 06820
0.08
$2,800,000
4
3.5
3,411
Recently Sold
537 Middlesex Rd, Darien, CT 06820
0.09
$1,601,000
5
4
3,300
Off Market
569 Middlesex Rd, Darien, CT 06820
0.10
$4,431,600
5
5
5,442
Off Market
15 Blueberry Ln, Darien, CT 06820
0.11
$3,801,300
4
4
4,861
Off Market
527 Middlesex Road, Darien, CT 06820
0.11
$6,315,300
6
7
8,007
Off Market
1 Ox Ridge Ln, Darien, CT 06820
0.11
$3,566,300
6
5
5,448
Off Market
16 Ox Ridge Ln, Darien, CT 06820
0.11
$5,721,500
5
2.5
2,614
Off Market
573 Middlesex Rd, Darien, CT 06820
0.13
$4,080,900
5
5
5,944
Off Market
6 Blueberry Lane, Darien, CT 06820
0.14
$2,300,000
3
2
2,043
Recently Sold
571 Middlesex Rd, Darien, CT 06820
0.14
$3,170,500
3
4
3,844
Off Market
19 Blueberry Lane, Darien, CT 06820
0.15
$3,711,000
4
2.5
3,881
Recently Sold
10 Blueberry Ln, Darien, CT 06820
0.15
$2,492,800
4
4
4,017
Off Market
20 Blueberry Ln, Darien, CT 06820
0.16
$2,083,400
3
2.5
3,000
Off Market
11 Ox Ridge Ln, Darien, CT 06820
0.17
$4,336,600
6
6
6,653
Off Market

Local Information

  • Map ViewExplore the area around 556 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1954
2 acre lot
5,262 sqft
$855/sqft
Garage

About this House

Fabulous colonial located on two beautiful acres offering privacy at its best all within a few minutes of town. this wonderful home was totally remodeled in 2007 boasts a formal living room with fireplace and french doors leading to a flagstone patio overlooking an expansive backyard. there is large library, a gourmet kitchen with stainless steel appliances adjacent to the family room with a fireplace, wet bar and french doors which open to the patio. Lower level includes a finished playroom and
556 Middlesex Rd, Darien, CT 06820 is a 6 bedroom, 7 bathroom, 5,262 sqft single-family home built in 1954. It last sold for $2,695,000 on Jun 29, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,498,400.

Home Details for 556 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 12Types of Rooms: Recreation Room
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1954Year Updated: 2007
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price and Tax history

DateEventPrice
Jun 29, 2016
Source: N/A
Sold
$2,695,000
Apr 13, 2016
Source: Agent Provided
Listed For Sale
$2,695,000
May 24, 2011
Source: N/A
Sold
$2,550,000
Mar 24, 2011
Source: Agent Provided
Pending
$2,775,000
Mar 24, 2011
Source: Agent Provided
Listed For Sale
$2,775,000

Market trends in Darien

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.82M
$155KMoM
Sale-to-List Price
110.3%
1.4%MoM
Price per sq ft
$821
$21MoM
Available listings
29
7MoM

Around this home

What Locals Say about Darien

At least 147 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 89 % Say yards are well-kept

  • 88 % Say parking is easy

  • 87 % Say car is needed

  • 84 % Say there's holiday spirit

  • 82 % Say people would walk alone at night

  • 80 % Say kids play outside

  • 73 % Say there's wildlife

  • 71 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 58 % Say neighbors are friendly

  • 58 % Say there are community events

  • 58 % Say there are sidewalks

  • 55 % Say it's walkable to restaurants

  • 48 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Kimrichardnyc
    "Happy, safe and friendly place to live and raise children. Need more diversification like in wesport CT though. "
    0
    Flag
  • Trulia User
    "This is the best town to raise kids and build friendships. The beaches, parks, restaurants, nature and proximity to NYC also makes a great place to live. We have found the people generally friendly and welcoming. "
    0
    Flag
  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
    Flag
  • Jessica_hatch7
    "NA commute to the city is an easy 65 minute train ride. We have two stations in Darien, both easily accessible. "
    3
    Flag
  • Peter S.
    "Holidays and school events. Dining and activities such as sports, the arts and many many social events"
    0
    Flag
  • Mzengo8
    "My neighborhood plays kid lacrosse/ basketball or football games. And we have parties on almost every holiday. Which is very fun for all of the kids on the block "
    0
    Flag
  • Bill T.
    "Dead end but on a hill and has a loop so kids can run around, play and explore. Lots of trees and woods surround the neighborhood."
    3
    Flag
  • Tad
    "My commute is five minutes to the train station, five minute walk from parking lot to the tracks, then an hour on the train to grand central each work day. "
    1
    Flag
  • Allison w.
    "They would love it, such a friendly area. Dogs are everywhere and appreciated. I have 2 dogs and I am so glad there are a ton of dogs around. "
    0
    Flag
  • Chad W.
    "Darien is as family friendly as it gets. There is a lot of money here. Some are kind, but many are snobby. It's a bit of a bubble, which is why many families move here."
    0
    Flag
  • Jessica_hatch7
    "The people are amazing and the schools are fantastic. We are only 60 minutes from the city and the trains run very frequently. "
    2
    Flag
  • Victoria_belluscio
    "Great place to raise children- excellent schools- everything is 5-10 min away so good for busy schedules! 2 train stations for easy commuting, beaches, parks and more!"
    0
    Flag
  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
    Flag
  • Bill T.
    "Big circle where no cars or trucks visit unless they live here or have business in the neighborhood... great place for kids"
    1
    Flag
  • dwenger
    "Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 556 Middlesex Rd

  • What is 556 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 556 Middlesex Rd in Darien, CT is $4,498,400.
  • What is the price history for 556 Middlesex Rd?
    556 Middlesex Rd in Darien, CT last sold for $2,695,000 in June 2016.
  • 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 $2.82M. That is down $155K from the prior month.
  • Does 556 Middlesex Rd have air conditioning?
    Yes, 556 Middlesex Rd in Darien, CT has air conditioning.
  • How big is the lot at 556 Middlesex Rd?
    The lot at 556 Middlesex Rd in Darien, CT is about 2 acres.

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