599 Middlesex Rd, Darien, CT 06820
OFF MARKET

599 Middlesex Rd
Darien, CT 06820

  • 8 Beds
  • 9 Baths
  • 11,764 sqft (on 2 acres)

$5,398,900

Trulia Estimate
as of Jun 5, 2026

$5,398,900

Trulia Estimate
as of Jun 5, 2026
8 Beds
9 Baths
11,764 sqft
(on 2 acres)

Local Information

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

Description

This single-family home is located at 599 Middlesex Rd, Darien, CT. 599 Middlesex Rd is in Darien, CT and in ZIP code 06820. This property has 8 bedrooms, 10 bathrooms and approximately 11,764 sqft of floor space. This property has a lot size of 2.00 acres and was built in 1998.
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, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 599 Middlesex Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 14Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Pantry, Recreation Room, Workshop, Sun RoomWet Bar
Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 4Floors: Tile, Carpet, HardwoodGated Entry
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Property Information

Year Built
Year Built: 1998Year Updated: 2024
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
DeckExterior: Stone, WoodGardenLawnPatioSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Building

Community rooms
Fitness Center

Price History for 599 Middlesex Rd

DatePriceEventSource
04/18/2022$4,125,000Sold
Smart MLS #170459687
01/28/2022$4,295,000ContingentSmart MLS #170459687
01/05/2022$4,295,000Listed For SaleSmart MLS #170459687
06/27/2007$4,000,000Sold
Smart MLS #98313656
09/25/2003$4,800,000Sold
N/A

Market trends in Darien

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
14MoM
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Property Tax and Assessment

Year2025
Tax$45,291
Assessment$2,925,790
Home facts updated by county records

Comparable Sales for 599 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
276 Mansfield Avenue, Darien, CT
0.39
Single-Family Home
$4,800,000
07/08/25
6
6
8,972
6 Cloudy Lane, Darien, CT
0.33
Single-Family Home
$4,500,000
05/29/26
5
5
5,864
451 Mansfield Ave, Darien, CT
0.47
Single-Family Home
$3,380,000
04/13/26
5
6
7,652
26 Peach Hill Road, Darien, CT
0.54
Single-Family Home
$6,125,000
07/01/25
6
7
8,454
50 Buttonwood Lane, Darien, CT
0.71
Single-Family Home
$4,500,000
12/03/25
7
6.5
7,200
48 Dorchester Road, Darien, CT
0.65
Single-Family Home
$5,295,000
07/22/25
5
6
6,242
15 Marianne Road, Darien, CT
0.81
Single-Family Home
$4,600,000
05/08/26
5
5
6,325
19 Blueberry Lane, Darien, CT
0.40
Single-Family Home
$3,711,000
06/03/26
4
2.5
3,881
15 Allwood Road, Darien, CT
0.94
Single-Family Home
$4,550,000
07/25/25
6
5.5
6,947
202 Mansfield Ave, Darien, CT
0.77
Single-Family Home
$2,795,000
08/21/25
6
6
6,058

Nearby homes

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Assigned Schools

These are the assigned schools for 599 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
    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
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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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599 Middlesex Rd, Darien, CT 06820 is a 8 bedroom, 10 bathroom, 11,764 sqft single-family home built in 1998. This property is not currently available for sale. 599 Middlesex Rd was last sold on Apr 18, 2022 for $4,125,000. The current Trulia Estimate for 599 Middlesex Rd is $5,398,900.