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

227 Middlesex Rd
Darien, CT 06820

  • 3 Beds
  • 2.5 Baths
  • 1,500 sqft (on 0.29 acres)

$1,705,400

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $11,074/mo*
Refinance Your Home

$1,705,400

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $11,074/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,500 sqft
(on 0.29 acres)

Local Information

  • Map ViewExplore the area around 227 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Location, Location! Fabulous, classic, chic updated Colonial in one of Darien's most desirable areas. Walk to Middle School, High School and Noroton Heights Train Station.  Featuring a completely updated kitchen with white quartz countertops, new cabinets, appliances and a Viking gas stove and range. An inviting, sundrenched and enclosed porch will greet you upon entering the open concept home. A bright LR with a gas fireplace and surround sound leads to a formal and chic DR.  The family room/play room is located off the kitchen. All bedrooms are on the 2nd floor and all have walk-in closets. Updated bathrooms. Lush landscaping. Private backyard with a large deck is great outdoor living and entertaining spaces. Minutes to Woodland Park, top rated elementary school, Metro-North train, town beaches, great restaurants and shopping
227 Middlesex Rd, Darien, CT 06820 is a 3 bedroom, 3 bathroom, 1,500 sqft single-family home built in 1924. It last sold for $1,095,000 on Feb 8, 2021. It is currently off market. The Trulia Estimate is $1,705,400, with a rent estimate of $6,131/month.

Home Highlights

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

Home Details for 227 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Other, OilAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle Not Wood, WoodPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1924Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Price History for 227 Middlesex Rd

DatePriceEventSource
02/08/2021$1,095,000Sold
Smart MLS #170357987
12/16/2020$1,095,000PendingAgent Provided
12/07/2020$1,095,000Listed For SaleAgent Provided
07/11/2014$950,000Sold
Smart MLS #99043782
01/28/2014$975,000PriceChange
Agent Provided
10/10/2013$995,000Listed For SaleAgent Provided
07/30/2010$675,000Sold
Smart MLS #98417566
04/14/2010$709,000PriceChange
Agent Provided
11/14/2009$729,000PriceChange
Agent Provided
09/14/2009$739,500PriceChange
Agent Provided
06/05/2009$749,500PriceChange
Agent Provided
04/17/2009$795,000Listed For SaleAgent Provided
01/29/1997$215,000Sold
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$11,796
Assessment$762,020
Home facts updated by county records

Comparable Sales for 227 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
223 Middlesex Road, Darien, CT
0.02
Single-Family Home
$1,540,000
03/16/26
3
1.5
1,840
223 Hollow Tree Ridge Rd, Darien, CT
0.39
Single-Family Home
$1,250,000
10/14/25
3
2
1,676
128 West Avenue, Darien, CT
0.53
Single-Family Home
$1,125,000
01/08/26
3
3
1,636
16 Fairfield Avenue, Darien, CT
0.44
Single-Family Home
$1,500,000
05/29/26
3
2
1,390
3 Revere Road, Darien, CT
0.04
Single-Family Home
$2,350,000
05/01/26
5
3
3,395
33 Ridgeley Street, Darien, CT
0.53
Single-Family Home
$1,675,000
08/14/25
3
2
2,343
14 Henry Street, Darien, CT
0.61
Single-Family Home
$1,275,000
06/04/26
3
2.5
1,493
281 West Avenue, Darien, CT
0.60
Single-Family Home
$1,519,000
05/29/26
3
1.5
1,658
7 Chestnut Street, Darien, CT
0.27
Single-Family Home
$855,000
11/21/25
2
1
1,056
182 Hollow Tree Ridge Road, Darien, CT
0.58
Single-Family Home
$1,825,000
06/30/26
4
2.5
2,067

Nearby homes

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Assigned Schools

These are the assigned schools for 227 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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Homes for sale near 227 Middlesex Rd

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Off Market Homes Near 227 Middlesex Rd

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