181 Middlesex Rd, Darien, CT 06820
OFF MARKET

181 Middlesex Rd
Darien, CT 06820

  • 6 Beds
  • 5.5 Baths
  • 5,066 sqft (on 0.69 acres)

$3,368,300

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $21,816/mo*
Refinance Your Home

$3,368,300

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $21,816/mo*
Refinance Your Home
6 Beds
5.5 Baths
5,066 sqft
(on 0.69 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Custom colonial with a refreshingly spacious layout for easy living and entertaining. Extensively renovated and expanded in 2011, this gracious home sits on 0.69 acres surrounded by stone walls close to the center of town. Six bedrooms including the master bedroom with en suite bath and walk-In closet. One bedroom perfect as an au pair suite or second bonus. Formal living room and adjacent dining room with skylights, library-Style built-Ins and wood burning fireplace. Updated kitchen and eat-In area. Bright and sunny family room. Large mudroom with custom cabinetry and extra storage. Desirable and convenient in-Town location, walkable to train, shopping, parks and school.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 181 Middlesex Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 14Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Sun Room
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: WoodLawnPatio
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1948Year Updated: 2012
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.69 acres

Price History for 181 Middlesex Rd

DatePriceEventSource
06/28/2017$1,750,000Sold
Smart MLS #99158212
05/12/2017$1,950,000PendingAgent Provided
01/06/2017$1,950,000PriceChange
Agent Provided
11/01/2016$2,000,000PriceChange
Agent Provided
09/30/2016$2,115,000PriceChange
Agent Provided
07/11/2016$2,218,000PriceChange
Agent Provided
06/20/2016$2,290,000PriceChange
Agent Provided
05/09/2016$2,395,000Listed For SaleAgent Provided
11/16/2006$1,265,000Sold
N/A
05/01/1998$709,500Sold
Smart MLS #98003636
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Property Tax and Assessment

Year2025
Tax$22,927
Assessment$1,481,060
Home facts updated by county records

Comparable Sales for 181 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
176 Middlesex Road, Darien, CT
0.09
Single-Family Home
$4,025,000
07/18/25
6
5.5
6,293
261 Hollow Tree Ridge Road, Darien, CT
0.15
Single-Family Home
$4,350,000
12/15/25
5
5.5
6,135
39 Deepwood Road, Darien, CT
0.22
Single-Family Home
$4,022,500
08/01/25
5
3.5
4,932
311 Noroton Avenue, Darien, CT
0.17
Single-Family Home
$3,550,000
12/17/25
5
5.5
5,356
108 Colony Road, Darien, CT
0.27
Single-Family Home
$1,850,000
06/20/25
4
2.5
2,869
6 Bouton Lane, Darien, CT
0.24
Single-Family Home
$3,250,000
07/02/25
6
8
6,233
3 Revere Road, Darien, CT
0.20
Single-Family Home
$2,350,000
05/01/26
5
3
3,395
7 Lantern Lane, Darien, CT
0.28
Single-Family Home
$2,355,000
06/12/25
4
3.5
3,742
300 Hollow Tree Ridge Road, Darien, CT
0.30
Single-Family Home
$4,900,000
09/02/25
5
7
6,118
76 Deepwood Road, Darien, CT
0.51
Single-Family Home
$2,287,500
02/27/26
5
4
3,897

Nearby homes

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Assigned Schools

These are the assigned schools for 181 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

  • 81 % 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
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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
    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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181 Middlesex Rd, Darien, CT 06820 is a 6 bedroom, 6 bathroom, 5,066 sqft single-family home built in 1948. This property is not currently available for sale. 181 Middlesex Rd was last sold on Jun 28, 2017 for $1,750,000. The current Trulia Estimate for 181 Middlesex Rd is $3,368,300.