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)

$2,142,200

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $13,879/mo*
Refinance Your Home

$2,142,200

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $13,879/mo*
Refinance Your Home
4 Beds
3.5 Baths
2,994 sqft
(on 0.47 acres)

Local Information

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

Description

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.
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. This description is from August 01, 2023

Home Highlights

Parking
2 Car Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

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
Last check for updates: about 2 hours 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

Price History for 21 Middlesex Road

DatePriceEventSource
07/31/2023$1,656,000Sold
Smart MLS #170579437
07/17/2023$1,499,999PendingSmart MLS #170579437
06/23/2023$1,499,999Listed For SaleSmart MLS #170579437
01/07/2010$1,125,000Sold
Smart MLS #98441430
12/25/2009$1,125,000Listed For SaleAgent Provided
06/27/2008$1,167,500Sold
Smart MLS #98377744
07/18/2000$640,000Sold
N/A
05/14/1996$425,000Sold
N/A
10/31/1995$422,000Sold
N/A
07/23/1992$430,000Sold
N/A
07/01/1988$385,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$15,148
Assessment$978,530
Home facts updated by county records

Comparable Sales for 21 Middlesex Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
11 Christie Hill Road, Darien, CT
0.14
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
0.12
Single-Family Home
$2,235,000
08/18/25
4
3.5
2,790
147 Holmes Avenue, Darien, CT
0.21
Single-Family Home
$1,850,000
07/21/25
5
3.5
2,974
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
53 Hoyt Street, Darien, CT
0.32
Single-Family Home
$1,725,000
05/14/26
3
3.5
2,180

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Assigned Schools

These are the assigned schools for 21 Middlesex Road.
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
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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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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Homes for rent near 21 Middlesex Road

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21 Middlesex Road, Darien, CT 06820 is a 4 bedroom, 4 bathroom, 2,994 sqft single-family home built in 1967. This property is not currently available for sale. 21 Middlesex Road was last sold on Jul 31, 2023 for $1,656,000 (10% higher than the asking price of $1,499,999). The current Trulia Estimate for 21 Middlesex Road is $2,142,200.