27 Middlesex Rd, Darien, CT 06820
OFF MARKET

$2,197,000

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,408 sqft (on 0.44 acres)

27 Middlesex Rd, Darien, CT 06820

Est. Refi. Payment $14,336/mo*
Refinance Your Home
Currently Off Market - Sold Jun 23, 2023 for $1,875,000

Home Value

Trulia Estimate
$2.2M
Since last month
Decreased$6K (-0.3%)
Since last year
Increased$122K (+5.9%)
Since last sale
Increased$322K (+17.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +80% in the last 10 years
MonthEstimated value
2026
August 2026$2.2M
July 2026$2.2M
June 2026$2.24M
May 2026$2.23M
April 2026$2.21M
March 2026$2.23M
February 2026$2.13M
January 2026$2.12M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
20 Denhurst Place, Darien, CT
0.19
Single-Family Home
$1,580,000
11/17/25
4
2.5
2,120
3 Abbey Road, Darien, CT
0.15
Single-Family Home
$2,258,000
06/01/26
4
2.5
2,450
3 Devon Road, Darien, CT
0.16
Single-Family Home
$1,950,000
10/23/25
4
3.5
2,568
8 Forest Road, Darien, CT
0.30
Single-Family Home
$1,650,000
11/21/25
4
3
2,707
19 Chester Road, Darien, CT
0.36
Single-Family Home
$2,365,000
07/31/26
4
2.5
3,264
30 Devon Rd, Darien, CT
0.30
Single-Family Home
$2,200,000
12/16/25
4
2.5
2,424
86 Middlesex Road, Darien, CT
0.34
Single-Family Home
$2,400,000
05/19/26
4
2.5
2,850
15 Sunnyside Avenue, Darien, CT
0.22
Single-Family Home
$1,875,000
12/01/25
3
2
2,308
25 Devon Road, Darien, CT
0.27
Single-Family Home
$1,710,000
04/27/26
4
1.5
1,953
105 Holmes Avenue, Darien, CT
0.40
Single-Family Home
$1,776,000
08/24/26
4
3
2,745

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
25 Middlesex Road, Darien, CT 06820
0.02
-
4
2.5
2,388
Off Market
21 Middlesex Road, Darien, CT 06820
0.06
$2,123,200
4
3.5
2,994
Off Market
12 Abbey Road, Darien, CT 06820
0.10
-
4
3.5
2,790
Off Market
2 Red Barn Road, Darien, CT 06820
0.12
$2,523,400
4
2.5
3,358
Off Market
154 Holmes Avenue, Darien, CT 06820
0.14
-
5
3.5
3,108
Off Market
15 Phillips Lane, Darien, CT 06820
0.11
-
4
3.5
3,599
Off Market
11 Stanley Road, Darien, CT 06820
0.13
$2,628,400
5
3
2,656
Off Market
11 Christie Hill Road, Darien, CT 06820
0.10
-
4
3
2,852
Off Market
8 Christie Hill Road, Darien, CT 06820
0.10
-
3
3.5
2,070
Off Market
3 Abbey Road, Darien, CT 06820
0.15
$2,258,000
4
2.5
2,450
Recently Sold
17 Stanley Road, Darien, CT 06820
0.16
-
2
1
1,290
Off Market
9 Fresh Meadows Lane, Darien, CT 06820
0.17
$2,926,600
4
3.5
3,884
Off Market

Local Information

  • Map ViewExplore the area around 27 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
0.44 acres
Living Area
2,408 sqft
Price/Sqft
$912
Parking
Garage

About this House

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
27 Middlesex Rd, Darien, CT 06820 is a 4 bedroom, 3 bathroom, 2,408 sqft single-family home built in 1994. It last sold for $1,875,000 on Jun 23, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,197,000, with a rent estimate of $7,764/month.

Home Details for 27 Middlesex Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 9Types of Rooms: Recreation Room
Heating & Cooling
Heating: OilAir ConditioningCooling System: CentralHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Washer
Fireplace & Spa
Fireplace

Property Information

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

Exterior Features

Exterior Home Features
Exterior: Wood
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.44 acres

Price and Tax history

DateEventPrice
Jun 23, 2023
Source: BHHS NE Properties sold #170555839_06820
Sold
$1,875,000
May 3, 2023
Source: Berkshire Hathaway HomeServices New England Properties #38104
Contingent
$1,575,000
Apr 20, 2023
Source: Berkshire Hathaway HomeServices New England Properties #38104
Listed For Sale
$1,575,000
Jun 23, 2010
Source: N/A
Sold
$1,150,000
Dec 16, 1994
Source: N/A
Sold
$469,500

Market trends in Darien

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.98M
$246KMoM
Sale-to-List Price
108.9%
3.3%MoM
Price per sq ft
$800
$12MoM
Available listings
36
18MoM

Around this home

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
    Flag
  • 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
    Flag
  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 27 Middlesex Rd

  • What is 27 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 27 Middlesex Rd in Darien, CT is $2,197,000.
  • What is the price history for 27 Middlesex Rd?
    27 Middlesex Rd in Darien, CT last sold for $1,875,000 in June 2023.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Darien?
    The median sale price in Darien is $2.98M. That is up $246K from the prior month.
  • Does 27 Middlesex Rd have air conditioning?
    Yes, 27 Middlesex Rd in Darien, CT has air conditioning.
  • Does 27 Middlesex Rd have a pool?
    Yes, 27 Middlesex Rd in Darien, CT has a pool.

Explore by feature - Pet Friendly

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