369 Middlesex Rd, Darien, CT 06820
Property image
Property image
OFF MARKET

$2,659,100

Trulia Estimate
  • 6 Beds
  • 3 Baths
  • 3,442 sqft (on 2 acres)

369 Middlesex Rd, Darien, CT 06820

Est. Refi. Payment $18,578/mo*
Refinance Your Home
Currently Off Market - Sold Jun 22, 2017 for $1,237,500

Home Value

Trulia Estimate
$2.66M
Since last month
Decreased$172K (-6.1%)
Since last year
Increased$273K (+11.4%)
Since last sale
Increased$1M (+114.9%)
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 +123% in the last 10 years
MonthEstimated value
2026
September 2026$2.66M
September 2026$2.66M
August 2026$2.83M
July 2026$2.81M
June 2026$2.87M
May 2026$2.75M
April 2026$2.69M
March 2026$2.75M
February 2026$2.68M
January 2026$2.58M
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
0.24
Single-Family Home
$2,711,000
09/21/26
4
3.5
4,100
26 Holly Lane, Darien, CT
0.32
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
28 Royle Road, Darien, CT
0.56
Single-Family Home
$3,050,000
09/10/26
5
3.5
3,829
174 Leroy Avenue, Darien, CT
0.43
Single-Family Home
$4,475,000
08/17/26
5
4.5
5,506
6 Old Parish Road, Darien, CT
0.43
Single-Family Home
$3,550,000
06/12/26
4
4.5
4,825
12 Libby Lane, Darien, CT
0.48
Single-Family Home
$2,870,000
09/02/26
4
3.5
2,750
16 Libby Lane, Darien, CT
0.47
Single-Family Home
$2,976,000
06/24/26
4
4.5
2,928
3 Revere Road, Darien, CT
0.58
Single-Family Home
$2,350,000
05/01/26
5
3
3,395
6 Priscilla Lane, Darien, CT
0.32
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
366 Hollow Tree Ridge Rd, Darien, CT
0.49
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
371 Middlesex Rd, Darien, CT 06820
0.04
$3,488,700
6
6.5
6,539
Off Market
373 Middlesex Rd, Darien, CT 06820
0.08
$2,203,500
4
2.5
3,660
Off Market
350 Middlesex Rd, Darien, CT 06820
0.08
$2,803,400
5
3.5
3,519
Off Market
383 Middlesex Rd, Darien, CT 06820
0.11
$3,272,300
4
4.5
4,508
Off Market
348 Middlesex Rd, Darien, CT 06820
0.11
$2,476,200
4
3
2,720
Off Market
375 Middlesex Rd, Darien, CT 06820
0.12
$3,441,700
6
6
4,320
Off Market
3 High School Ln, Darien, CT 06820
0.13
$2,696,500
5
4
4,000
Off Market
332 Middlesex Rd, Darien, CT 06820
0.15
$2,497,600
4
4
3,217
Off Market
340 Middlesex Rd, Darien, CT 06820
0.15
$5,103,600
6
7
6,554
Off Market
12 Linda Ln, Darien, CT 06820
0.16
$3,060,500
5
4.5
3,942
Off Market
5 High School Ln, Darien, CT 06820
0.16
$2,588,600
5
3.5
3,167
Off Market
338 Middlesex Rd, Darien, CT 06820
0.16
$2,640,600
4
4
3,459
Off Market
337 Middlesex Rd, Darien, CT 06820
0.16
-
Studio
-
-
Off Market
385 Middlesex Rd, Darien, CT 06820
0.17
$5,459,400
6
8
7,244
Off Market
114 Hanson Road, Darien, CT 06820
0.17
$3,826,000
5
7
4,786
Off Market
14 Linda Ln, Darien, CT 06820
0.18
$2,869,200
4
3
3,420
Off Market
330 Middlesex Rd, Darien, CT 06820
0.18
$2,779,900
4
3.5
3,618
Off Market
10 Linda Ln, Darien, CT 06820
0.19
$3,958,200
5
5
4,843
Off Market
210 Leroy Ave, Darien, CT 06820
0.19
$5,443,400
6
5.5
7,500
Off Market
11 High School Ln, Darien, CT 06820
0.19
$1,686,900
5
3
2,849
Off Market

Local Information

  • Map ViewExplore the area around 369 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1756
2 acre lot
3,442 sqft
$773/sqft

About this House

Original main house of Stony Brook Farm, updated and renovated, but still maintaining original character. Enter the large foyer into this 3442 sf 6 bedroom colonial. Wainscoting and beautiful old wood floors create character. Large dining room with fireplace leads to butler's pantry and country kitchen, which also opens onto bright sun room. Unique living room and connecting parlor create great flow, and move seamlessly into the 20 x 10 family room with fireplace leading to terrace, overlooking 2 beautiful acres. Master on 2nd floor with dressing room, and 2 other bedrooms, with 3 more on top floor plus office. Close to High School and easy to train. Charm plus function. Best of both worlds.
369 Middlesex Rd, Darien, CT 06820 is a 6 bedroom, 3 bathroom, 3,442 sqft single-family home built in 1756. It last sold for $1,237,500 on Jun 22, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,659,100, with a rent estimate of $9,519/month.

Home Details for 369 Middlesex Rd

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Interior Details
Number of Rooms: 12
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Vinyl

Property Information

Year Built
Year Built: 1756Year Updated: 2023
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price and Tax history

DateEventPrice
Jun 22, 2017
Source: Smart MLS #99143786
Sold
$1,237,500
May 16, 2017
Source: Agent Provided
Pending
$1,295,000
Mar 22, 2017
Source: Agent Provided
PriceChange
$1,295,000
Price decreased by 13%
Feb 2, 2017
Source: Agent Provided
PriceChange
$1,495,000
Price decreased by 4%
Jul 12, 2016
Source: Agent Provided
Listed For Sale
$1,550,000

Market trends in Darien

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.82M
$155KMoM
Sale-to-List Price
110.3%
1.4%MoM
Price per sq ft
$821
$21MoM
Available listings
29
7MoM

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.
  • 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
  • dwenger
    "Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 369 Middlesex Rd

  • What is 369 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 369 Middlesex Rd in Darien, CT is $2,659,100.
  • What is the price history for 369 Middlesex Rd?
    369 Middlesex Rd in Darien, CT last sold for $1,237,500 in June 2017.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Darien?
    The median sale price in Darien is $2.82M. That is down $155K from the prior month.
  • Does 369 Middlesex Rd have laundry facilities?
    Yes, 369 Middlesex Rd in Darien, CT has in-unit laundry.
  • How big is the lot at 369 Middlesex Rd?
    The lot at 369 Middlesex Rd in Darien, CT is about 2 acres.

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