375 Middlesex Rd, Darien, CT 06820
OFF MARKET

$3,409,700

Trulia Estimate
  • 6 Beds
  • 6 Baths
  • 4,320 sqft (on 2.03 acres)

375 Middlesex Rd, Darien, CT 06820

Est. Refi. Payment $22,933/mo*
Refinance Your Home
Currently Off Market - Sold Jun 17, 2013 for $1,766,500

Home Value

Trulia Estimate
$3.41M
Since last month
Decreased$38K (-1.1%)
Since last year
Increased$159K (+4.9%)
Since last sale
Increased$2M (+92.7%)
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 +51% in the last 10 years
MonthEstimated value
2026
November 2026$3.4M
October 2026$3.43M
September 2026$3.44M
August 2026$3.55M
July 2026$3.5M
June 2026$3.59M
May 2026$3.5M
April 2026$3.45M
March 2026$3.43M
February 2026$3.29M
January 2026$3.2M
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
0.22
Single-Family Home
$2,711,000
09/21/26
4
3.5
4,100
174 Leroy Avenue, Darien, CT
0.42
Single-Family Home
$4,475,000
08/17/26
5
4.5
5,506
23 Fox Hill Ln, Darien, CT
0.29
Single-Family Home
$7,523,000
07/15/26
5
5.5
7,400
26 Holly Lane, Darien, CT
0.43
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
58 Knollwood Lane, Darien, CT
0.38
Single-Family Home
$3,750,000
07/23/26
8
6
5,658
6 Priscilla Lane, Darien, CT
0.28
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
21 Fox Hill Ln, Darien, CT
0.33
Single-Family Home
$4,597,500
06/29/26
5
6.5
6,308
6 Old Parish Road, Darien, CT
0.54
Single-Family Home
$3,550,000
06/12/26
4
4.5
4,825
28 Royle Road, Darien, CT
0.51
Single-Family Home
$3,050,000
09/10/26
5
3.5
3,829
366 Hollow Tree Ridge Rd, Darien, CT
0.54
Single-Family Home
$6,705,000
08/17/26
6
6
6,775

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
373 Middlesex Rd, Darien, CT 06820
0.04
$2,175,600
4
2.5
3,660
Off Market
385 Middlesex Rd, Darien, CT 06820
0.05
$5,475,400
6
8
7,244
Off Market
383 Middlesex Rd, Darien, CT 06820
0.05
$3,240,700
4
4.5
4,508
Off Market
371 Middlesex Rd, Darien, CT 06820
0.08
$3,454,000
6
6.5
6,539
Off Market
114 Hanson Road, Darien, CT 06820
0.08
$3,782,600
5
7
4,786
Off Market
393 Middlesex Rd, Darien, CT 06820
0.10
$3,320,400
7
5
4,193
Off Market
388 Middlesex Rd, Darien, CT 06820
0.10
$4,742,400
5
4.5
7,703
Off Market
12 Linda Ln, Darien, CT 06820
0.11
$3,032,100
5
4.5
3,942
Off Market
10 Linda Ln, Darien, CT 06820
0.11
$3,924,300
5
5
4,843
Off Market
369 Middlesex Rd, Darien, CT 06820
0.12
$2,668,700
6
3
3,442
Off Market
390 Middlesex Rd, Darien, CT 06820
0.12
$3,542,000
5
3.5
4,334
Off Market
110 Hanson Rd, Darien, CT 06820
0.14
$4,466,200
6
4.5
4,922
Off Market
397 Middlesex Rd, Darien, CT 06820
0.14
$2,474,000
4
3.5
3,520
Off Market
8 Linda Ln, Darien, CT 06820
0.15
$2,390,900
4
4
3,612
Off Market
14 Linda Ln, Darien, CT 06820
0.15
$2,826,500
4
3
3,420
Off Market
394 Middlesex Rd, Darien, CT 06820
0.15
$2,744,400
5
3.5
4,034
Off Market
11 Linda Lane, Darien, CT 06820
0.16
$4,234,300
5
5
5,182
Off Market
69 Saint Nicholas Rd, Darien, CT 06820
0.17
$6,286,700
8
7
8,723
Off Market
350 Middlesex Rd, Darien, CT 06820
0.18
$2,763,800
5
3.5
3,519
Off Market
6 Linda Ln, Darien, CT 06820
0.18
$2,167,900
5
4
3,275
Off Market

Local Information

  • Map ViewExplore the area around 375 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1954
2.03 acre lot
4,320 sqft
$789/sqft
Garage

About this House

Large beautifully maintained center hall colonial home on over 2 acres with circular drive and flexible floor plan. The wrap-around deck and large patio overlook the professionally landscaped grounds. All rooms are generous in size w/fireplaces in the LR, library and play room. French doors in the LR open to the deck as do two doors in library. Large eat-in KIT w/center island w/breakfast bar, a separate breakfast rm and sun room w/patio. Upstairs are 6 BRs and 4 baths. The master bedroom has full bath, a dressing room with walk up stairs to the attic. The lower level play room with fireplace has doors that open to the back yard. Plenty of storage. South-facing deck with pergola and full length deck along rear of house. 3 car garage.
375 Middlesex Rd, Darien, CT 06820 is a 6 bedroom, 7 bathroom, 4,320 sqft single-family home built in 1954. It last sold for $1,766,500 on Jun 17, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,409,700.

Home Details for 375 Middlesex Rd

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 12
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1954
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
DeckExterior: WoodPatioSprinkler System
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 2.03 acres

Price and Tax history

DateEventPrice
Jun 17, 2013
Source: Smart MLS #99003861
Sold
$1,766,500
Feb 13, 2013
Source: Agent Provided
Listed For Sale
$1,895,000
Jan 3, 2013
Source: Agent Provided
ListingRemoved
$1,895,000
Sep 11, 2012
Source: Agent Provided
Listed For Sale
$1,895,000

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 375 Middlesex Rd

  • What is 375 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 375 Middlesex Rd in Darien, CT is $3,409,700.
  • What is the price history for 375 Middlesex Rd?
    375 Middlesex Rd in Darien, CT last sold for $1,766,500 in June 2013.
  • 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.
  • How big is the lot at 375 Middlesex Rd?
    The lot at 375 Middlesex Rd in Darien, CT is about 2 acres.
  • Does 375 Middlesex Rd have a garage?
    Yes, 375 Middlesex Rd in Darien, CT has a garage.

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Off Market Homes Near 375 Middlesex Rd

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