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

205 Middlesex Rd
Darien, CT 06820

  • 3 Beds
  • 1,666 sqft (on 0.40 acres)

$3,729,900

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $24,130/mo*
Refinance Your Home

$3,729,900

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $24,130/mo*
Refinance Your Home
3 Beds
1,666 sqft
(on 0.40 acres)

Local Information

  • Map ViewExplore the area around 205 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Darien gem in a storybook setting with all the excitement of living in town and near fabulous new Darien Commons. Close to schools, trains and town, this charming 3-bedroom 2 full bath sunlit cape boasts a large private backyard of almost half an acre. Enter into the freshly updated living room with a wall of windows and F/P, and move easily into the separate dining room, family room/ office/ first floor bedroom near full bath. The charming country kitchen is off the lovely breezeway which connects to the garage and leads to back deck and yard. The large basement provides you with many options. Two lovely public beaches, many parks, and the new wonderful downtown Darien, all just 55 minutes from NYC!
205 Middlesex Rd, Darien, CT 06820 is a 3 bedroom, 1,666 sqft single-family home built in 1952. It last sold for $3,600,000 on Nov 7, 2024. It is currently off market. The Trulia Estimate is $3,729,900, with a rent estimate of $5,312/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 205 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Interior Details
Number of Rooms: 15
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1952
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
DeckExterior: WoodPatio
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.40 acres

Price History for 205 Middlesex Rd

DatePriceEventSource
11/07/2024$3,600,000Sold
N/A
10/26/2022$1,100,000Sold
Smart MLS #170515222
09/23/2022$1,200,000ContingentSmart MLS #170515222
08/10/2022$1,200,000Listed For SaleHalstead / Brown Harris Stevens #170515222
12/01/1999$452,250Sold
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$29,147
Assessment$1,882,860
Home facts updated by county records

Comparable Sales for 205 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
223 Middlesex Road, Darien, CT
0.09
Single-Family Home
$1,540,000
03/16/26
3
1.5
1,840
311 Noroton Avenue, Darien, CT
0.08
Single-Family Home
$3,550,000
12/17/25
5
5.5
5,356
3 Revere Road, Darien, CT
0.09
Single-Family Home
$2,350,000
05/01/26
5
3
3,395
5 Shields Lane, Darien, CT
0.24
Single-Family Home
$4,602,000
05/01/26
4
6
4,748
223 Hollow Tree Ridge Rd, Darien, CT
0.28
Single-Family Home
$1,250,000
10/14/25
3
2
1,676
16 Libby Lane, Darien, CT
0.20
Single-Family Home
$2,976,000
06/24/26
4
4.5
2,928
176 Middlesex Road, Darien, CT
0.19
Single-Family Home
$4,025,000
07/18/25
6
5.5
6,293
33 Ridgeley Street, Darien, CT
0.45
Single-Family Home
$1,675,000
08/14/25
3
2
2,343
182 Hollow Tree Ridge Road, Darien, CT
0.49
Single-Family Home
$1,825,000
06/30/26
4
2.5
2,067
229 West Avenue, Darien, CT
0.54
Single-Family Home
$1,852,000
06/30/26
3
1.5
2,752

Nearby homes

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Assigned Schools

These are the assigned schools for 205 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 "
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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 205 Middlesex Rd

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Off Market Homes Near 205 Middlesex Rd

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