59 Middlesex Rd, Darien, CT 06820
OFF MARKET

$1,557,900

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,617 sqft (on 0.26 acres)

59 Middlesex Rd, Darien, CT 06820

Est. Refi. Payment $11,001/mo*
Refinance Your Home
Currently Off Market - Sold Nov 7, 2013 for $640,000

Home Value

Trulia Estimate
$1.56M
Since last month
Decreased$7K (-0.4%)
Since last year
Increased$132K (+9.3%)
Since last sale
Increased$911K (+142.3%)
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 +90% in the last 10 years
MonthEstimated value
2026
October 2026$1.55M
September 2026$1.56M
August 2026$1.56M
July 2026$1.54M
June 2026$1.61M
May 2026$1.58M
April 2026$1.54M
March 2026$1.53M
February 2026$1.45M
January 2026$1.44M
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
0.07
Single-Family Home
$1,325,000
08/13/26
4
2
1,402
15 Sunnyside Avenue, Darien, CT
0.05
Single-Family Home
$1,875,000
12/01/25
3
2
2,308
25 Devon Road, Darien, CT
0.10
Single-Family Home
$1,710,000
04/27/26
4
1.5
1,953
83 Hoyt Street, Darien, CT
0.42
Single-Family Home
$850,000
07/23/26
3
1.5
1,546
415 West Ave, Darien, CT
0.41
Single-Family Home
$875,000
12/12/25
3
1.5
1,883
17 Sunnyside Avenue, Darien, CT
0.04
Single-Family Home
$1,675,000
03/26/26
3
2.5
2,234
19 Park Lane, Darien, CT
0.31
Single-Family Home
$1,350,000
10/24/25
3
1.5
1,502
28 Lake Dr, Darien, CT
0.42
Single-Family Home
$950,000
07/20/26
4
3
1,544
139 Holmes Avenue, Darien, CT
0.26
Single-Family Home
$1,735,000
08/28/26
3
2.5
2,184
223 Hollow Tree Ridge Rd, Darien, CT
0.59
Single-Family Home
$1,250,000
10/14/25
3
2
1,676

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
61 Middlesex Rd, Darien, CT 06820
0.01
$1,801,600
3
2
2,397
Off Market
57 Middlesex Rd, Darien, CT 06820
0.01
$1,364,500
3
2
1,676
Off Market
16 Sunnyside Ave, Darien, CT 06820
0.02
$2,336,500
4
2.5
3,032
Off Market
55 Middlesex Rd, Darien, CT 06820
0.03
$2,148,400
4
3
1,784
Off Market
14 Sunnyside Ave, Darien, CT 06820
0.03
$2,453,300
3
2.5
2,200
Off Market
Hillcrest Ave, Darien, CT 06820
0.03
-
-
-
-
Off Market
64 Middlesex Road, Darien, CT 06820
0.03
$2,311,100
4
3
2,513
Off Market
67 Middlesex Rd, Darien, CT 06820
0.04
$2,354,500
4
3.5
3,300
Off Market
13 Glenvale Avenue, Darien, CT 06820
0.04
$1,631,200
3
2
1,662
Off Market
62 Middlesex Rd, Darien, CT 06820
0.04
$2,118,700
4
3
2,156
Off Market
58 Middlesex Rd, Darien, CT 06820
0.04
$2,224,500
4
2.5
2,346
Off Market
17 Sunnyside Avenue, Darien, CT 06820
0.04
$1,675,000
3
2.5
2,234
Recently Sold
12 Sunnyside Ave, Darien, CT 06820
0.05
$2,676,500
4
3.5
3,008
Off Market
15 Sunnyside Avenue, Darien, CT 06820
0.05
$1,984,500
3
2
2,308
Off Market
19 Sunnyside Ave, Darien, CT 06820
0.05
$2,707,300
5
3.5
4,100
Off Market
56 Middlesex Rd, Darien, CT 06820
0.05
$1,279,900
2
2
1,266
Off Market
11 Glenvale Ave, Darien, CT 06820
0.05
$1,470,500
3
2
1,352
Off Market
66 Middlesex Rd, Darien, CT 06820
0.05
$1,568,100
3
2
1,870
Off Market
69 Middlesex Rd, Darien, CT 06820
0.05
$1,561,600
4
2
2,341
Off Market
49 Middlesex Rd, Darien, CT 06820
0.05
$2,065,100
5
3
2,968
Off Market

Local Information

  • Map ViewExplore the area around 59 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1949
0.26 acre lot
1,617 sqft
$963/sqft
Garage

About this House

This little gem is all about location, quality and value. Privately sited in a much loved neighborhood, this home is filled with the quality and charm of 1940's craftsmanship. A large living room, formal dining room with fireplace, an eat-in kitchen and a screened-in porch offer endless space for family and entertaining. Three large bedrooms, two full baths and a very private back yard complete the home.
59 Middlesex Rd, Darien, CT 06820 is a 3 bedroom, 2 bathroom, 1,617 sqft single-family home built in 1949. It last sold for $640,000 on Nov 7, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,557,900, with a rent estimate of $7,537/month.

Home Details for 59 Middlesex Rd

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 6
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1949Year Updated: 2014
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
Nov 7, 2013
Source: Smart MLS #99040011
Sold
$640,000
Sep 4, 2013
Source: Agent Provided
Listed For Sale
$639,000

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 59 Middlesex Rd

  • What is 59 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 59 Middlesex Rd in Darien, CT is $1,557,900.
  • What is the price history for 59 Middlesex Rd?
    59 Middlesex Rd in Darien, CT last sold for $640,000 in November 2013.
  • 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.
  • How big is the lot at 59 Middlesex Rd?
    The lot at 59 Middlesex Rd in Darien, CT is about 0.26 acres (11,326 sq ft).
  • Does 59 Middlesex Rd have a garage?
    Yes, 59 Middlesex Rd in Darien, CT has a garage.

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