59 Middlesex Rd, Darien, CT 06820
OFF MARKET

59 Middlesex Rd
Darien, CT 06820

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

$1,561,500

Trulia Estimate
as of May 13, 2026
Est. Refi. Payment $9,909/mo*
Refinance Your Home

$1,561,500

Trulia Estimate
as of May 13, 2026
Est. Refi. Payment $9,909/mo*
Refinance Your Home
3 Beds
2 Baths
1,617 sqft
(on 0.26 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 59 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
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 History for 59 Middlesex Rd

DatePriceEventSource
11/07/2013$640,000Sold
Smart MLS #99040011
09/04/2013$639,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$12,144
Assessment$784,490
Home facts updated by county records

Comparable Sales for 59 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
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
415 West Avenue, 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
35 Intervale Road, Darien, CT
0.13
Single-Family Home
$1,976,000
05/27/25
4
2
1,918
71 Hoyt St, Darien, CT
0.35
Single-Family Home
$900,000
08/11/25
3
3
1,968
19 Park Lane, Darien, CT
0.31
Single-Family Home
$1,350,000
10/24/25
3
1.5
1,502
64 Middlesex Road, Darien, CT
0.03
Single-Family Home
$2,150,000
05/15/25
4
3
2,513
223 Hollow Tree Ridge Rd, Darien, CT
0.59
Single-Family Home
$1,250,000
10/14/25
3
2
1,676
102 Rose Lane, Darien, CT
0.38
Single-Family Home
$1,225,000
09/10/25
3
1.5
1,828

Assigned Schools

These are the assigned schools for 59 Middlesex Rd.
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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

  • 81 % 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

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
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  • 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
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  • 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
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  • 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

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59 Middlesex Rd, Darien, CT 06820 is a 3 bedroom, 2 bathroom, 1,617 sqft single-family home built in 1949. This property is not currently available for sale. 59 Middlesex Rd was last sold on Nov 7, 2013 for $640,000. The current Trulia Estimate for 59 Middlesex Rd is $1,561,500.