21 Middlesex Road, Darien, CT 06820
OFF MARKET

21 Middlesex Road
Darien, CT 06820

  • 4 Beds
  • 3.5 Baths
  • 2,994 sqft (on 0.47 acres)

$2,134,500

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $13,998/mo*
Refinance Your Home

$2,134,500

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $13,998/mo*
Refinance Your Home
4 Beds
3.5 Baths
2,994 sqft
(on 0.47 acres)

Home Value

Trulia Estimate
$2.13M
Since last month
Decreased$23K (-1.1%)
Since last year
Increased$145K (+7.3%)
Since last sale
Increased$479K (+28.9%)
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 +76% in the last 10 years
MonthEstimated value
2026
August 2026$2.13M
July 2026$2.16M
June 2026$2.2M
May 2026$2.17M
April 2026$2.14M
March 2026$2.17M
February 2026$2.06M
January 2026$2.03M
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
8 Forest Road, Darien, CT
0.35
Single-Family Home
$1,650,000
11/21/25
4
3
2,707
3 Devon Road, Darien, CT
0.21
Single-Family Home
$1,950,000
10/23/25
4
3.5
2,568
3 Abbey Road, Darien, CT
0.18
Single-Family Home
$2,258,000
06/01/26
4
2.5
2,450
19 Chester Road, Darien, CT
0.42
Single-Family Home
$2,365,000
07/31/26
4
2.5
3,264
53 Hoyt Street, Darien, CT
0.32
Single-Family Home
$1,725,000
05/14/26
3
3.5
2,180
86 Middlesex Road, Darien, CT
0.39
Single-Family Home
$2,400,000
05/19/26
4
2.5
2,850
34 Intervale Road, Darien, CT
0.30
Single-Family Home
$2,850,000
06/22/26
4
3.5
3,180
6 Park Lane, Darien, CT
0.33
Single-Family Home
$1,550,000
06/29/26
4
2.5
2,108

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
0.05
$1,915,500
4
2.5
2,388
Off Market
2 Red Barn Road, Darien, CT 06820
0.08
$2,526,900
4
2.5
3,358
Off Market
15 Phillips Lane, Darien, CT 06820
0.07
$2,455,500
4
3.5
3,599
Off Market
12 Abbey Road, Darien, CT 06820
0.12
$2,377,400
4
3.5
2,790
Off Market
9 Fresh Meadows Lane, Darien, CT 06820
0.11
$2,909,200
4
3.5
3,884
Off Market
154 Holmes Avenue, Darien, CT 06820
0.14
$2,299,200
5
3.5
3,108
Off Market
11 Christie Hill Road, Darien, CT 06820
0.14
$2,077,800
4
3
2,852
Off Market
20 Denhurst Place, Darien, CT 06820
0.19
$1,580,000
4
2.5
2,120
Recently Sold
11 Stanley Road, Darien, CT 06820
0.17
$2,639,200
5
3
2,656
Off Market
3 Abbey Road, Darien, CT 06820
0.18
$2,258,000
4
2.5
2,450
Recently Sold
8 Christie Hill Road, Darien, CT 06820
0.16
$2,041,300
3
3.5
2,070
Off Market

Local Information

  • Map ViewExplore the area around 21 Middlesex Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1967
Lot Size
0.47 acres
Living Area
2,994 sqft
Price/Sqft
$713
Parking
2 Car Garage

About this House

Move right Into this updated colonial featuring a spectacular kitchen, His & Hers Baths and closets in Primary Bedroom suite. Lower Level with office and playroom adds an additional 700 sq.ft. Set well back from the street on half an acre. Close proximity to school and train.
21 Middlesex Road, Darien, CT 06820 is a 4 bedroom, 4 bathroom, 2,994 sqft single-family home built in 1967. It last sold for $1,656,000 on Jul 31, 2023 (10% above the $1,499,999 asking price). It is currently off market. The Trulia Estimate is $2,134,500, with a rent estimate of $7,311/month.
Last check for updates: about 1 hour ago
Listed by Bernadette Fischer, (917) 734-2417
Houlihan Lawrence, (203) 655-8238
Bought with: Michael Carriero, (203) 253-5737, Compass Connecticut, LLC
Source: Smart MLS, MLS#170579437

Home Details for 21 Middlesex Road

Interior Features

Interior Details
Basement: Full,Partially Finished,Storage SpaceNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Office, Rec Play Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2994 Square Feet
Appliances & Utilities
Appliances: Electric Cooktop, Oven, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PatioFencing: PartialExterior: Underground SprinklerFoundation: Block, Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Attached,Garage Door Opener,Shared Driveway,Paved
Frontage
Waterfront: Beach AccessNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2294 Square FeetFinished Area (below surface): 700 Square Feet

Property Information

Year Built
Year Built: 1967
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Shingle Siding, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 105530

Price & Status

Price
List Price: $1,499,999
Status Change & Dates
Off Market Date: Wed Jul 12 2023Possession Timing: Negotiable

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Darien
School Information
Elementary School: HolmesJr High / Middle School: MiddlesexHigh School: Darien

Building

Building Area
Building Area: 2994 Square Feet

Community

Community Features: Playground, Pool
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.47 acres

Miscellaneous

BasementMls Number: 170579437Attic: Pull Down Stairs, StorageAbove Grade Unfinished Area: 2294

Additional Information

PlaygroundPool

Price and Tax history

DateEventPrice
Jul 31, 2023
Source: Smart MLS #170579437
Sold
$1,656,000
Jul 17, 2023
Source: Smart MLS #170579437
Pending
$1,499,999
Jun 23, 2023
Source: Smart MLS #170579437
Listed For Sale
$1,499,999
Jan 7, 2010
Source: Smart MLS #98441430
Sold
$1,125,000
Dec 25, 2009
Source: Agent Provided
Listed For Sale
$1,125,000

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

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Frequently asked questions about 21 Middlesex Road

  • What is 21 Middlesex Road estimated to be worth?
    Trulia's estimated value for 21 Middlesex Road in Darien, CT is $2,134,500.
  • What is the price history for 21 Middlesex Road?
    21 Middlesex Road in Darien, CT last sold for $1,656,000 in July 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 21 Middlesex Road have air conditioning?
    Yes, 21 Middlesex Road in Darien, CT has air conditioning.
  • Does 21 Middlesex Road have a pool?
    Yes, 21 Middlesex Road in Darien, CT has a pool.

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