388 Middlesex Rd, Darien, CT 06820
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OFF MARKET

388 Middlesex Rd
Darien, CT 06820

  • 5 Beds
  • 4.5 Baths
  • 7,703 sqft (on 2.70 acres)

$4,751,700

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $30,644/mo*
Refinance Your Home

$4,751,700

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $30,644/mo*
Refinance Your Home
5 Beds
4.5 Baths
7,703 sqft
(on 2.70 acres)

Local Information

  • Map ViewExplore the area around 388 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This is it! This exceptional center hall colonial on 2.7 acres simply has it all. Generously sized rooms and fantastic flow for both living and entertaining. This fabulous 5 bedroom home offers a fabuous white kitchen with newly done floors and top of the line appliances. It opens to a spectacular family room with coffered ceiling, fireplace and magnificent views of the private back yard. Other highlights include a luxurious master suite, a media room equipped with a projector, 100 screen and custom bar as well as a fully finished basement beyond compare. The 2.77 bucolic professionally landscaped yard offers a heated free form pool and a pond for all seasons that is safely fenced in. This outstanding home is nestled privately off the road and conveniently located in central Darien.
388 Middlesex Rd, Darien, CT 06820 is a 5 bedroom, 5 bathroom, 7,703 sqft single-family home built in 1965. It last sold for $2,500,000 on Apr 12, 2019. It is currently off market. The Trulia Estimate is $4,751,700, with a rent estimate of $21,612/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 388 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Other, OilAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 13
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1965Year Updated: 2004
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 2.70 acres

Additional Information

On Site Laundry Available

Price History for 388 Middlesex Rd

DatePriceEventSource
04/12/2019$2,500,000Sold
Smart MLS #170159847
02/19/2019$2,595,000PendingAgent Provided
02/05/2019$2,595,000Listed For SaleAgent Provided
11/23/2018$2,695,000ListingRemovedAgent Provided
09/16/2018$2,695,000PriceChange
Agent Provided
08/04/2018$2,795,000PriceChange
Agent Provided
02/12/2018$2,995,000PriceChange
Agent Provided
09/11/2017$3,275,000PriceChange
Agent Provided
05/22/2017$3,395,000Listed For SaleAgent Provided
04/03/2006$3,550,000Sold
N/A
01/14/2002$1,600,000Sold
Smart MLS #98106340
05/20/1999$1,395,000Sold
Smart MLS #98033818
08/30/1991$620,000Sold
N/A

Market trends in Darien

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.73M
Sale-to-List Price
105.6%
Price per sq ft
$787
Available listings
54
11MoM
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Property Tax and Assessment

Year2025
Tax$34,737
Assessment$2,243,990
Home facts updated by county records

Comparable Sales for 388 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
6 Priscilla Lane, Darien, CT
0.21
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
21 Fox Hill Ln, Darien, CT
0.26
Single-Family Home
$4,597,500
06/29/26
5
6.5
6,308
6 Fox Hill Ln, Darien, CT
0.41
Single-Family Home
$4,000,000
08/11/25
5
5
5,330
54 Stony Brook Rd, Darien, CT
0.48
Single-Family Home
$4,425,000
08/04/25
6
6
6,446
26 Holly Lane, Darien, CT
0.51
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
326 Hollow Tree Ridge Road, Darien, CT
0.74
Single-Family Home
$3,650,000
08/20/25
5
4.5
6,860
202 Mansfield Ave, Darien, CT
0.53
Single-Family Home
$2,795,000
08/21/25
6
6
6,058
6 Old Parish Road, Darien, CT
0.57
Single-Family Home
$3,550,000
06/12/26
4
4.5
4,825
43 Stony Brook Rd, Darien, CT
0.54
Single-Family Home
$3,775,000
06/23/26
5
6.5
7,200
1 Fox Hill Lane, Darien, CT
0.47
Single-Family Home
$4,500,000
08/12/25
4
4.5
5,561

Nearby homes

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Assigned Schools

These are the assigned schools for 388 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

  • 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
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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
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  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
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  • 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
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Apartments for Rent

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Homes for sale near 388 Middlesex Rd

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Off Market Homes Near 388 Middlesex Rd

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