599 Middlesex Rd, Darien, CT 06820
OFF MARKET

$5,634,400

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

599 Middlesex Rd, Darien, CT 06820

Est. Refi. Payment $37,036/mo*
Refinance Your Home
Currently Off Market - Sold Apr 18, 2022 for $4,125,000

Home Value

Trulia Estimate
$5.63M
Since last month
Increased$96K (+1.7%)
Since last year
Increased$525K (+10.2%)
Since last sale
Increased$2M (+37.4%)
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 +39% in the last 10 years
MonthEstimated value
2026
August 2026$5.67M
July 2026$5.57M
June 2026$5.55M
May 2026$5.4M
April 2026$5.37M
March 2026$5.47M
February 2026$5.17M
January 2026$5.18M
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
316 Mansfield Avenue, Darien, CT
0.19
Single-Family Home
$5,625,000
07/24/26
5
6
9,039
272 Mansfield Ave, Darien, CT
0.43
Single-Family Home
$5,550,000
08/06/26
6
6
7,496
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
225 Brookside Rd, Darien, CT
0.65
Single-Family Home
$4,650,000
06/09/26
6
6
8,000
50 Buttonwood Lane, Darien, CT
0.71
Single-Family Home
$4,500,000
12/03/25
7
6.5
7,200
304 Brookside Road, Darien, CT
0.69
Single-Family Home
$6,095,000
07/16/26
6
6.5
7,344
74 Salisbury Road, Darien, CT
0.62
Single-Family Home
$4,795,000
06/23/26
5
5
6,798
561 Middlesex Road, Darien, CT
0.18
Single-Family Home
$2,800,000
08/10/26
4
3.5
3,411
234 Brookside Road, Darien, CT
0.72
Single-Family Home
$4,750,000
08/14/26
6
6.5
6,829

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
316 Mansfield Avenue, Darien, CT 06820
0.19
$5,625,000
5
6
9,039
Recently Sold
561 Middlesex Road, Darien, CT 06820
0.18
$2,800,000
4
3.5
3,411
Recently Sold
527 Middlesex Road, Darien, CT 06820
0.29
$6,213,200
6
7
8,007
Off Market
10 Cloudy Lane, Darien, CT 06820
0.30
$3,744,700
6
4.5
3,880
Off Market
276 Mansfield Avenue, Darien, CT 06820
0.39
$5,176,100
6
6
8,972
Off Market
6 Cloudy Lane, Darien, CT 06820
0.33
$4,500,000
5
5
5,864
Recently Sold
6 Blueberry Lane, Darien, CT 06820
0.35
$2,300,000
3
2
2,043
Recently Sold
24 Saddle Ridge Road, Darien, CT 06820
0.40
$4,751,200
5
6
6,546
Off Market
19 Blueberry Lane, Darien, CT 06820
0.40
$3,711,000
4
2.5
3,881
Recently Sold
11 Half Mile Road, Darien, CT 06820
0.41
$5,003,800
5
5.5
6,656
Off Market
55 Blueberry Lane, Darien, CT 06820
0.47
$5,769,800
6
8.5
9,203
Off Market
700 Hollow Tree Ridge Road, Darien, CT 06820
0.48
$3,950,000
5
5.5
5,500
For Sale

Local Information

  • Map ViewExplore the area around 599 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
1998
Lot Size
2 acres
Living Area
11,764 sqft
Price/Sqft
$479
Parking
Garage

About this House

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.
599 Middlesex Rd, Darien, CT 06820 is a 8 bedroom, 10 bathroom, 11,764 sqft single-family home built in 1998. It last sold for $4,125,000 on Apr 18, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,634,400, with a rent estimate of $7,775/month.

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: OilAir ConditioningHeating Fuel: Oil
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 and Tax history

DateEventPrice
Apr 18, 2022
Source: Smart MLS #170459687
Sold
$4,125,000
Jan 28, 2022
Source: Smart MLS #170459687
Contingent
$4,295,000
Jan 5, 2022
Source: Smart MLS #170459687
Listed For Sale
$4,295,000
Jun 27, 2007
Source: Smart MLS #98313656
Sold
$4,000,000
Sep 25, 2003
Source: N/A
Sold
$4,800,000

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

Frequently asked questions about 599 Middlesex Rd

  • What is 599 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 599 Middlesex Rd in Darien, CT is $5,634,400.
  • What is the price history for 599 Middlesex Rd?
    599 Middlesex Rd in Darien, CT last sold for $4,125,000 in April 2022.
  • 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 599 Middlesex Rd have a pool?
    Yes, 599 Middlesex Rd in Darien, CT has a pool.
  • Does 599 Middlesex Rd have laundry facilities?
    Yes, 599 Middlesex Rd in Darien, CT has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Pool

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Apartments for Rent

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Off Market Homes Near 599 Middlesex Rd

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