27 Middlesex Rd, Darien, CT 06820
OFF MARKET

27 Middlesex Rd
Darien, CT 06820

  • 4 Beds
  • 2.5 Baths
  • 3,270 sqft (on 0.44 acres)

$2,242,300

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $14,418/mo*
Refinance Your Home

$2,242,300

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $14,418/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,270 sqft
(on 0.44 acres)

Local Information

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

Description

Picture perfect, meticulously maintained 4 bed home, set back with a relaxing front porch, attached 2 car garage, & a fully fenced flat backyard. Entry welcomes you either to the kitchen, the office or upstairs. Kitchen is nestled between the dining room & breakfast area, a wonderful entertaining space (appliances updated last 5 years. The patio door leads off the open plan family room, seamless flow for inside outside living. Upstairs, the spacious landing guides you left, to any of the three bedrooms, the family bath, and right, laundry room & expansive primary suite. With a soaring ceiling, the primary has a walk-in closet, & whirlpool bath with double sinks - an oasis retreat. The lower level is a dream - media room, gym and slumber-party area.This home has everything
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
Porch, Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 27 Middlesex Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 9Types of Rooms: Recreation RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
Washer
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1994
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.44 acres

Price History for 27 Middlesex Rd

DatePriceEventSource
06/23/2023$1,875,000Sold
BHHS NE Properties sold #170555839_06820
05/03/2023$1,575,000ContingentBerkshire Hathaway HomeServices New England Properties #38104
04/20/2023$1,575,000Listed For SaleBerkshire Hathaway HomeServices New England Properties #38104
06/23/2010$1,150,000Sold
N/A
12/16/1994$469,500Sold
N/A
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Property Tax and Assessment

Year2023
Tax$11,875
Assessment$674,310
Home facts updated by county records

Comparable Sales for 27 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
11 Christie Hill Road, Darien, CT
0.10
Single-Family Home
$1,951,000
07/10/25
4
3
2,852
154 Holmes Avenue, Darien, CT
0.14
Single-Family Home
$2,160,000
07/30/25
5
3.5
3,108
20 Denhurst Place, Darien, CT
0.19
Single-Family Home
$1,580,000
11/17/25
4
2.5
2,120
12 Abbey Road, Darien, CT
0.10
Single-Family Home
$2,235,000
08/18/25
4
3.5
2,790
147 Holmes Avenue, Darien, CT
0.19
Single-Family Home
$1,850,000
07/21/25
5
3.5
2,974
8 Forest Road, Darien, CT
0.30
Single-Family Home
$1,650,000
11/21/25
4
3
2,707
3 Devon Road, Darien, CT
0.16
Single-Family Home
$1,950,000
10/23/25
4
3.5
2,568
86 Middlesex Road, Darien, CT
0.34
Single-Family Home
$2,400,000
05/19/26
4
2.5
2,850
6 Intervale Rd, Darien, CT
0.19
Single-Family Home
$2,330,000
07/28/25
5
4.5
3,496
16 Phillips Ln, Darien, CT
0.07
Single-Family Home
$3,650,000
04/27/26
4
5
4,750

Nearby homes

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Assigned Schools

These are the assigned schools for 27 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. "
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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
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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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27 Middlesex Rd, Darien, CT 06820 is a 4 bedroom, 3 bathroom, 3,270 sqft single-family home built in 1994. This property is not currently available for sale. 27 Middlesex Rd was last sold on Jun 23, 2023 for $1,875,000. The current Trulia Estimate for 27 Middlesex Rd is $2,242,300.