397 Middlesex Rd, Darien, CT 06820
OFF MARKET

397 Middlesex Rd
Darien, CT 06820

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

$2,570,700

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $16,613/mo*
Refinance Your Home

$2,570,700

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $16,613/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,520 sqft
(on 2.07 acres)

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

Description

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. It is currently off market. The Trulia Estimate is $2,570,700, with a rent estimate of $15,000/month.

Home Highlights

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

Home Details for 397 Middlesex Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8Types of Rooms: Breakfast Nook, Recreation Room
Heating & Cooling
Heating: Baseboard, OtherAir 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 History for 397 Middlesex Rd

DatePriceEventSource
05/01/2019$6,500ListingRemovedAgent Provided
04/30/2019$6,500PriceChange
Agent Provided
02/20/2019$6,600PriceChange
Agent Provided
01/06/2019$6,800Listed For RentAgent Provided
09/06/2018$1,395,000ListingRemovedAgent Provided
06/01/2018$1,395,000PriceChange
Agent Provided
05/26/2017$1,495,000PriceChange
Agent Provided
03/17/2017$1,595,000PriceChange
Agent Provided
01/13/2017$1,699,000Listed For SaleAgent Provided
12/02/2016$1,665,000ListingRemovedAgent Provided
08/04/2016$1,665,000PriceChange
Agent Provided
06/17/2016$1,675,000PriceChange
Agent Provided
05/19/2016$1,695,000PriceChange
Agent Provided
05/16/2016$1,699,000PriceChange
Agent Provided
03/21/2016$1,795,000PriceChange
Agent Provided
10/27/2015$1,875,000Listed For SaleAgent Provided

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$17,409
Assessment$1,124,620
Home facts updated by county records

Comparable Sales for 397 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
19 Blueberry Lane, Darien, CT
0.59
Single-Family Home
$3,711,000
06/03/26
4
2.5
3,881
26 Holly Lane, Darien, CT
0.57
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
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
6 Old Parish Road, Darien, CT
0.68
Single-Family Home
$3,550,000
06/12/26
4
4.5
4,825
6 Fox Hill Ln, Darien, CT
0.45
Single-Family Home
$4,000,000
08/11/25
5
5
5,330
345 Hollow Tree Ridge Road, Darien, CT
0.70
Single-Family Home
$100,000
04/14/26
4
2.5
2,913
1 Fox Hill Lane, Darien, CT
0.51
Single-Family Home
$4,500,000
08/12/25
4
4.5
5,561
178 Christie Hill Road, Darien, CT
0.83
Single-Family Home
$2,150,000
07/31/25
4
4.5
3,436

Nearby homes

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Assigned Schools

These are the assigned schools for 397 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
    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
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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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Explore by feature - Pet Friendly

Explore by feature - Garage

17 rentals with a garage in Darien, CT

Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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Homes for sale near 397 Middlesex Rd

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Off Market Homes Near 397 Middlesex Rd

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