369 Middlesex Rd, Darien, CT 06820
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OFF MARKET

369 Middlesex Rd
Darien, CT 06820

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

$2,777,000

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $17,940/mo*
Refinance Your Home

$2,777,000

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $17,940/mo*
Refinance Your Home
6 Beds
3 Baths
3,442 sqft
(on 2 acres)

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

Description

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. It is currently off market. The Trulia Estimate is $2,777,000, with a rent estimate of $7,823/month.

Home Highlights

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

Home Details for 369 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
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 History for 369 Middlesex Rd

DatePriceEventSource
06/22/2017$1,237,500Sold
Smart MLS #99143786
05/16/2017$1,295,000PendingAgent Provided
03/22/2017$1,295,000PriceChange
Agent Provided
02/02/2017$1,495,000PriceChange
Agent Provided
07/12/2016$1,550,000Listed For SaleAgent Provided
06/22/2016$1,237,500Sold
N/A
05/05/2016$1,725,000Listed For SaleAgent Provided
12/01/1975$103,000Sold
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$22,257
Assessment$1,437,800
Home facts updated by county records

Comparable Sales for 369 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
26 Holly Lane, Darien, CT
0.32
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
6 Old Parish Road, Darien, CT
0.43
Single-Family Home
$3,550,000
06/12/26
4
4.5
4,825
54 Stony Brook Rd, Darien, CT
0.41
Single-Family Home
$4,425,000
08/04/25
6
6
6,446
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
217 Mansfield Avenue, Darien, CT
0.68
Single-Family Home
$2,250,000
05/29/26
3
2.5
2,760
178 Christie Hill Road, Darien, CT
0.80
Single-Family Home
$2,150,000
07/31/25
4
4.5
3,436
326 Hollow Tree Ridge Road, Darien, CT
0.56
Single-Family Home
$3,650,000
08/20/25
5
4.5
6,860
25 Libby Lane, Darien, CT
0.38
Single-Family Home
$4,325,000
07/29/25
5
6
5,545

Nearby homes

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Assigned Schools

These are the assigned schools for 369 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. "
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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. "
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  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
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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 "
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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
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  • 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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17 rentals with a garage in Darien, CT

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Homes for sale near 369 Middlesex Rd

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Off Market Homes Near 369 Middlesex Rd

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