385 Middlesex Rd, Darien, CT 06820
OFF MARKET

385 Middlesex Rd
Darien, CT 06820

  • 6 Beds
  • 8 Baths
  • 7,244 sqft (on 2 acres)

$5,499,100

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $35,655/mo*
Refinance Your Home

$5,499,100

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $35,655/mo*
Refinance Your Home
6 Beds
8 Baths
7,244 sqft
(on 2 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

This single-family home is located at 385 Middlesex Rd, Darien, CT. 385 Middlesex Rd is in Darien, CT and in ZIP code 06820. This property has 6 bedrooms, 8 bathrooms and approximately 7,244 sqft of floor space. This property has a lot size of 2.00 acres and was built in 1962.
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
Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 385 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Forced Air, Other, Radiant, Oil, OtherAir ConditioningCooling System: Central, OtherHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Number of Rooms: 12Wet Bar
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: BrickPatioSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1962Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price History for 385 Middlesex Rd

DatePriceEventSource
11/05/2014$2,700,000Sold
Smart MLS #99057657
06/28/2014$3,100,000PriceChange
Agent Provided
05/15/2014$3,200,000PriceChange
Agent Provided
03/25/2014$3,350,000Listed For SaleAgent Provided
06/28/2004$2,362,500Sold
Smart MLS #98186093
03/04/2002$1,900,000Sold
N/A
06/01/2000$1,500,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$47,399
Assessment$3,061,940
Home facts updated by county records

Comparable Sales for 385 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
26 Peach Hill Road, Darien, CT
0.38
Single-Family Home
$6,125,000
07/01/25
6
7
8,454
202 Mansfield Ave, Darien, CT
0.60
Single-Family Home
$2,795,000
08/21/25
6
6
6,058
6 Priscilla Lane, Darien, CT
0.30
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
54 Stony Brook Rd, Darien, CT
0.53
Single-Family Home
$4,425,000
08/04/25
6
6
6,446
10 Holly Lane, Darien, CT
0.48
Single-Family Home
$4,450,325
05/21/25
5
6
6,012
12 Kona Road, Darien, CT
0.55
Single-Family Home
$4,400,000
05/29/25
5
6.5
6,805
326 Hollow Tree Ridge Road, Darien, CT
0.67
Single-Family Home
$3,650,000
08/20/25
5
4.5
6,860
25 Libby Lane, Darien, CT
0.54
Single-Family Home
$4,325,000
07/29/25
5
6
5,545
276 Mansfield Avenue, Darien, CT
0.66
Single-Family Home
$4,800,000
07/08/25
6
6
8,972
50 Buttonwood Lane, Darien, CT
0.77
Single-Family Home
$4,500,000
12/03/25
7
6.5
7,200

Assigned Schools

These are the assigned schools for 385 Middlesex Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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
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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
    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

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385 Middlesex Rd, Darien, CT 06820 is a 6 bedroom, 8 bathroom, 7,244 sqft single-family home built in 1962. This property is not currently available for sale. 385 Middlesex Rd was last sold on Nov 5, 2014 for $2,700,000. The current Trulia Estimate for 385 Middlesex Rd is $5,499,100.