55 Middlesex Rd, Darien, CT 06820
OFF MARKET

$2,075,400

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 1,784 sqft (on 0.28 acres)

55 Middlesex Rd, Darien, CT 06820

Est. Refi. Payment $14,178/mo*
Refinance Your Home
Currently Off Market - Sold Feb 5, 2010 for $785,000

Home Value

Trulia Estimate
$2.08M
Since last month
Decreased$64K (-3%)
Since last year
Increased$119K (+6.1%)
Since last sale
Increased$1M (+165.5%)
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 +59% in the last 10 years
MonthEstimated value
2026
October 2026$2.08M
October 2026$2.08M
September 2026$2.15M
August 2026$2.14M
July 2026$2.12M
June 2026$2.19M
May 2026$2.15M
April 2026$2.09M
March 2026$2.09M
February 2026$2M
January 2026$1.95M
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
13 Devon Road, Darien, CT
0.08
Single-Family Home
$1,325,000
08/13/26
4
2
1,402
17 Sunnyside Avenue, Darien, CT
0.07
Single-Family Home
$1,675,000
03/26/26
3
2.5
2,234
25 Devon Road, Darien, CT
0.12
Single-Family Home
$1,710,000
04/27/26
4
1.5
1,953
8 Forest Road, Darien, CT
0.18
Single-Family Home
$1,650,000
11/21/25
4
3
2,707
30 Devon Rd, Darien, CT
0.16
Single-Family Home
$2,200,000
12/16/25
4
2.5
2,424
3 Abbey Road, Darien, CT
0.17
Single-Family Home
$2,258,000
06/01/26
4
2.5
2,450
28 Lake Dr, Darien, CT
0.40
Single-Family Home
$950,000
07/20/26
4
3
1,544
20 Denhurst Place, Darien, CT
0.29
Single-Family Home
$1,580,000
11/17/25
4
2.5
2,120
6 Park Lane, Darien, CT
0.35
Single-Family Home
$1,550,000
06/29/26
4
2.5
2,108
139 Holmes Avenue, Darien, CT
0.25
Single-Family Home
$1,735,000
08/28/26
3
2.5
2,184

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
57 Middlesex Rd, Darien, CT 06820
0.02
$1,311,600
3
2
1,676
Off Market
13 Glenvale Avenue, Darien, CT 06820
0.02
$1,611,300
3
2
1,662
Off Market
49 Middlesex Rd, Darien, CT 06820
0.02
$2,015,500
5
3
2,968
Off Market
59 Middlesex Rd, Darien, CT 06820
0.03
$1,518,500
3
2
1,617
Off Market
11 Glenvale Ave, Darien, CT 06820
0.03
$1,442,300
3
2
1,352
Off Market
56 Middlesex Rd, Darien, CT 06820
0.04
$1,216,400
2
2
1,266
Off Market
47 Middlesex Rd, Darien, CT 06820
0.04
$1,678,800
4
3
2,679
Off Market
58 Middlesex Rd, Darien, CT 06820
0.04
$2,216,200
4
2.5
2,346
Off Market
14 Sunnyside Ave, Darien, CT 06820
0.04
$2,427,900
3
2.5
2,200
Off Market
54 Middlesex Rd, Darien, CT 06820
0.04
$1,785,500
4
3
1,992
Off Market
16 Sunnyside Ave, Darien, CT 06820
0.04
$2,301,200
4
2.5
3,032
Off Market
9 Glenvale Ave, Darien, CT 06820
0.04
$1,953,200
4
3
2,390
Off Market
8 Glenvale Ave, Darien, CT 06820
0.04
$1,444,900
3
2
1,636
Off Market
61 Middlesex Rd, Darien, CT 06820
0.04
$1,780,200
3
2
2,397
Off Market
12 Sunnyside Ave, Darien, CT 06820
0.04
$2,683,500
4
3.5
3,008
Off Market
52 Middlesex Rd, Darien, CT 06820
0.04
$1,744,800
4
2.5
1,914
Off Market
45 Middlesex Rd, Darien, CT 06820
0.05
$2,182,700
4
2.5
2,851
Off Market
50 Middlesex Rd, Darien, CT 06820
0.05
$2,035,500
4
2.5
3,000
Off Market
64 Middlesex Road, Darien, CT 06820
0.05
$2,310,400
4
3
2,513
Off Market
10 Sunnyside Ave, Darien, CT 06820
0.05
$2,060,600
4
2
1,948
Off Market

Local Information

  • Map ViewExplore the area around 55 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1925
0.28 acre lot
1,784 sqft
$1,163/sqft
Garage

About this House

This single-family home is located at 55 Middlesex Rd, Darien, CT. 55 Middlesex Rd is in Darien, CT and in ZIP code 06820. This property has 4 bedrooms, 3 bathrooms and approximately 1,784 sqft of floor space. This property has a lot size of 10890 sqft and was built in 1925.
55 Middlesex Rd, Darien, CT 06820 is a 4 bedroom, 3 bathroom, 1,784 sqft single-family home built in 1925. It last sold for $785,000 on Feb 5, 2010. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,075,400, with a rent estimate of $7,269/month.

Home Details for 55 Middlesex Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 8Types of Rooms: Recreation RoomCeiling Fan
Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: StuccoGardenLawnPatio
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1925Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Price and Tax history

DateEventPrice
Feb 5, 2010
Source: Smart MLS #98431102
Sold
$785,000

Market trends in Darien

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
34
5MoM
Sourced by Trulia Market Trends

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.
  • David Holst-grubbe
    "The city is entirely safe and heavily patrolled by town cops. The school system is second to none anywhere. The city spends a great deal of money to keep everything clean and well maintained."
    0
    Flag
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 55 Middlesex Rd

  • What is 55 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 55 Middlesex Rd in Darien, CT is $2,075,400.
  • What is the price history for 55 Middlesex Rd?
    55 Middlesex Rd in Darien, CT last sold for $785,000 in February 2010.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Darien?
    Residents describe Darien, CT as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Darien, CT.
  • How big is the lot at 55 Middlesex Rd?
    The lot at 55 Middlesex Rd in Darien, CT is about 0.25 acres (10,890 sq ft).
  • Does 55 Middlesex Rd have a garage?
    Yes, 55 Middlesex Rd in Darien, CT has a garage.

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Off Market Homes Near 55 Middlesex Rd

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