397 Middlesex Rd, Darien, CT 06820
OFF MARKET

$2,474,000

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,520 sqft (on 2.07 acres)

397 Middlesex Rd, Darien, CT 06820

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Home Value

Trulia Estimate
$2.47M
Since last month
Decreased$47K (-1.9%)
Since last year
Increased$91K (+3.9%)
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 +54% in the last 10 years
MonthEstimated value
2026
November 2026$2.45M
October 2026$2.47M
September 2026$2.5M
August 2026$2.55M
July 2026$2.55M
June 2026$2.59M
May 2026$2.57M
April 2026$2.52M
March 2026$2.51M
February 2026$2.4M
January 2026$2.34M
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
18 Linda Lane, Darien, CT
0.23
Single-Family Home
$2,711,000
09/21/26
4
3.5
4,100
23 Fox Hill Ln, Darien, CT
0.18
Single-Family Home
$7,523,000
07/15/26
5
5.5
7,400
19 Blueberry Lane, Darien, CT
0.59
Single-Family Home
$3,711,000
06/03/26
4
2.5
3,881
28 Royle Road, Darien, CT
0.54
Single-Family Home
$3,050,000
09/10/26
5
3.5
3,829
561 Middlesex Road, Darien, CT
0.70
Single-Family Home
$2,800,000
08/10/26
4
3.5
3,411
26 Holly Lane, Darien, CT
0.57
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
174 Leroy Avenue, Darien, CT
0.50
Single-Family Home
$4,475,000
08/17/26
5
4.5
5,506
21 Fox Hill Ln, Darien, CT
0.23
Single-Family Home
$4,597,500
06/29/26
5
6.5
6,308
6 Priscilla Lane, Darien, CT
0.34
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
217 Mansfield Avenue, Darien, CT
0.52
Single-Family Home
$2,250,000
05/29/26
3
2.5
2,760

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
393 Middlesex Rd, Darien, CT 06820
0.04
$3,320,400
7
5
4,193
Off Market
110 Hanson Rd, Darien, CT 06820
0.07
$4,466,200
6
4.5
4,922
Off Market
2 Althea Ln, Darien, CT 06820
0.07
$3,010,600
4
4
3,593
Off Market
141 Hanson Rd, Darien, CT 06820
0.08
$2,860,500
5
5
3,352
Off Market
400 Middlesex Rd, Darien, CT 06820
0.09
$3,195,200
4
4
3,653
Off Market
385 Middlesex Rd, Darien, CT 06820
0.09
$5,475,400
6
8
7,244
Off Market
394 Middlesex Rd, Darien, CT 06820
0.09
$2,744,400
5
3.5
4,034
Off Market
127 Hanson Rd, Darien, CT 06820
0.10
$2,785,500
4
3
4,032
Off Market
438 Middlesex Rd, Darien, CT 06820
0.10
$2,962,600
5
4
3,451
Off Market
114 Hanson Road, Darien, CT 06820
0.11
$3,782,600
5
7
4,786
Off Market
Hanson Rd, Darien, CT 06820
0.11
$2,217,600
4
4.5
4,446
Off Market
390 Middlesex Rd, Darien, CT 06820
0.11
$3,516,300
5
3.5
4,334
Off Market
8 Linda Ln, Darien, CT 06820
0.11
$2,411,100
4
4
3,612
Off Market
6 Linda Ln, Darien, CT 06820
0.12
$2,167,900
5
4
3,275
Off Market
440 Middlesex Rd, Darien, CT 06820
0.12
$5,566,200
6
7
7,300
Off Market
10 Linda Ln, Darien, CT 06820
0.13
$3,924,300
5
5
4,843
Off Market
4 Linda Ln, Darien, CT 06820
0.13
$5,470,900
6
7
6,800
Off Market
1 Althea Ln, Darien, CT 06820
0.14
$6,292,400
5
7.5
7,504
Off Market
375 Middlesex Rd, Darien, CT 06820
0.14
$3,409,700
6
6
4,320
Off Market
388 Middlesex Rd, Darien, CT 06820
0.14
$4,742,400
5
4.5
7,703
Off Market

Local Information

  • Map ViewExplore the area around 397 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1960
2.07 acre lot
3,520 sqft
$703/sqft
Garage

About this House

Renovated in 2018, new kitchen, new bathrooms, refinished and new floors, new int/ext paint, new roof. 2 acre property, large Family Rm w/walkout to patio, Sunroom/or Office w/walkout to patio. En suite Master BR w/walk-in closet. HW floors, large rooms, eat in kitchen. New Washer/Dryer. Lots of finished storage space and convenient 1/2 bath on lower level. 1.6 miles to train, .4 to Darien High. Tenant to provide renters insurance. No pets.
397 Middlesex Rd, Darien, CT 06820 is a 4 bedroom, 4 bathroom, 3,520 sqft single-family home built in 1960. More recently, it was listed as a rental in January 2019 with an asking price of $6,800 per month. That rental listing was removed on May 1, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,474,000, with a rent estimate of $9,491/month.

Home Details for 397 Middlesex Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8Types of Rooms: Breakfast Nook, Recreation Room
Heating & Cooling
Heating: BaseboardAir ConditioningHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Other
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: OtherPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1960Year Updated: 2018
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 2.07 acres

Price and Tax history

DateEventPrice
May 1, 2019
Source: Agent Provided
ListingRemoved
$6,500
Apr 30, 2019
Source: Agent Provided
PriceChange
$6,500
Price decreased by 2%
Feb 20, 2019
Source: Agent Provided
PriceChange
$6,600
Price decreased by 3%
Jan 6, 2019
Source: Agent Provided
Listed For Rent
$6,800
Sep 6, 2018
Source: Agent Provided
ListingRemoved
$1,395,000

Market trends in Darien

Last updated October 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
36
2MoM
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 397 Middlesex Rd

  • What is 397 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 397 Middlesex Rd in Darien, CT is $2,474,000.
  • 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.
  • What are the closest schools to 397 Middlesex Rd?
    The closest schools to 397 Middlesex Rd in Darien, CT are Darien High School (rated 10/10), Middlesex Middle School (rated 10/10), Ox Ridge Elementary School (Pre-K, rated 10/10).
  • Does 397 Middlesex Rd have laundry facilities?
    Yes, 397 Middlesex Rd in Darien, CT has in-unit laundry.
  • How big is the lot at 397 Middlesex Rd?
    The lot at 397 Middlesex Rd in Darien, CT is about 2.1 acres.

Explore by feature - Pet Friendly

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

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Off Market Homes Near 397 Middlesex Rd

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