527 Middlesex Road, Darien, CT 06820
OFF MARKET

527 Middlesex Road
Darien, CT 06820

  • 6 Beds
  • 7 Baths
  • 8,007 sqft (on 2 acres)

$6,305,500

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $41,238/mo*
Refinance Your Home

$6,305,500

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $41,238/mo*
Refinance Your Home
6 Beds
7 Baths
8,007 sqft
(on 2 acres)

Home Value

Trulia Estimate
$6.31M
Since last month
Increased$12K (+0.2%)
Since last year
Increased$750K (+13.5%)
Since last sale
Increased$1M (+18.8%)
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 +48% in the last 10 years
MonthEstimated value
2026
August 2026$6.32M
July 2026$6.31M
June 2026$6.37M
May 2026$6.09M
April 2026$6.02M
March 2026$6.06M
February 2026$5.82M
January 2026$5.77M
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
0.34
Single-Family Home
$5,625,000
07/24/26
5
6
9,039
6 Cloudy Lane, Darien, CT
0.51
Single-Family Home
$4,500,000
05/29/26
5
5
5,864
21 Fox Hill Ln, Darien, CT
0.46
Single-Family Home
$4,597,500
06/29/26
5
6.5
6,308
50 Buttonwood Lane, Darien, CT
0.75
Single-Family Home
$4,500,000
12/03/25
7
6.5
7,200
19 Blueberry Lane, Darien, CT
0.16
Single-Family Home
$3,711,000
06/03/26
4
2.5
3,881
561 Middlesex Road, Darien, CT
0.17
Single-Family Home
$2,800,000
08/10/26
4
3.5
3,411
28 Crooked Mile Road, Darien, CT
0.77
Single-Family Home
$4,315,000
06/11/26
5
6
4,653

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
19 Blueberry Lane, Darien, CT 06820
0.16
$3,711,000
4
2.5
3,881
Recently Sold
561 Middlesex Road, Darien, CT 06820
0.17
$2,800,000
4
3.5
3,411
Recently Sold
6 Blueberry Lane, Darien, CT 06820
0.23
$2,300,000
3
2
2,043
Recently Sold
24 Saddle Ridge Road, Darien, CT 06820
0.33
$4,743,000
5
6
6,546
Off Market
316 Mansfield Avenue, Darien, CT 06820
0.34
$5,625,000
5
6
9,039
Recently Sold
55 Blueberry Lane, Darien, CT 06820
0.38
$5,709,300
6
8.5
9,203
Off Market
26 Peach Hill Road, Darien, CT 06820
0.39
$6,524,700
6
7
8,454
Off Market
660 Hollow Tree Ridge Rd, Darien, CT 06820
0.43
$2,649,500
5
5
5,362
Off Market
276 Mansfield Avenue, Darien, CT 06820
0.42
$5,112,300
6
6
8,972
Off Market
21 Fox Hill Ln, Darien, CT 06820
0.46
$4,597,500
5
6.5
6,308
Recently Sold
10 Cloudy Lane, Darien, CT 06820
0.46
$3,774,500
6
4.5
3,880
Off Market

Local Information

  • Map ViewExplore the area around 527 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
2008
Lot Size
2 acres
Living Area
8,007 sqft
Price/Sqft
$787
Parking
3 Car Garage

About this House

Immerse yourself in the exceptional setting and architectural elegance of 527 Middlesex Road. Every aspect of this home was thoughtfully designed to complement its surroundings. The generous open layout effortlessly guides you through the home, offering views of the tree-lined driveway, and picturesque Highland Farm. The grand terrace with ample seating and fire pit overlooks the views of the sprawling landscaped yard and the serene woodlands that adjoin the Wee Burn Country Club. The stunning Gunite pool is the perfect finishing touch to this special property. The home showcases expert craftsmanship with a classic layout designed to incorporate formal areas and private spaces, while maximizing natural light and cardinal point orientation. The gourmet kitchen and family room provide a warm and inviting space for gatherings. The dining, library, and living rooms are elegantly arranged around a grand main hall, creating a seamless connection between the main and upper levels. This spectacular home and property are not to be missed.
527 Middlesex Road, Darien, CT 06820 is a 6 bedroom, 8 bathroom, 8,007 sqft single-family home built in 2008. It last sold for $5,320,000 on Sep 5, 2024 (2% above the $5,199,000 asking price). It is currently off market. The Trulia Estimate is $6,305,500, with a rent estimate of $30,615/month.
Last check for updates: about 2 hours ago
Listed by Lynne Somerville, (203) 984-9040
Compass Connecticut, LLC, (203) 423-3100
Bought with: Peter Stuart, (203) 219-5427, Houlihan Lawrence, (203) 655-8238
Source: Smart MLS, MLS#24017718

Home Details for 527 Middlesex Road

Interior Features

Interior Details
Basement: Full,Partially FinishedNumber of Rooms: 14Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Media Room, Office, Rec Play Room, Study, Sun Room
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 8Number of Bathrooms (full): 6Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 8007 Square Feet
Appliances & Utilities
Utilities: Underground UtilitiesAppliances: Oven/Range, Oven, Refrigerator, Dishwasher, Washer, Dryer, Wine Cooler, Water HeaterDishwasherDryerLaundry: Upper Level,Mud RoomRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 4Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: WoodPatio / Porch: TerraceExterior: Rain Gutters, Underground SprinklerFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Attached,Garage Door Opener
Pool
Pool: Gunite, In GroundPool
Frontage
Waterfront: Beach AccessNot on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 8007 Square Feet

Property Information

Year Built
Year Built: 2008
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Shingle SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Not Included in Sale: Front Entry & DR Chandelier, Front Hall Sconces, FR Drapes (hardware incl.) TV's (brackets incl.) Sonos Equip. Incl: Media Room Seating & ProjectorParcel Number: 103354

Price & Status

Price
List Price: $5,199,000
Status Change & Dates
Off Market Date: Fri May 24 2024Possession Timing: Negot

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 8007 Square Feet

Community

Community Features: Library, Park, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 2 Acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24017718Attic: Storage, Floored, Walk-upAbove Grade Unfinished Area: 8007

Additional Information

LibraryParkTennis Court(s)

Price and Tax history

DateEventPrice
Sep 5, 2024
Source: Smart MLS #24017718
Sold
$5,320,000
May 24, 2024
Source: Smart MLS #24017718
Pending
$5,199,000
May 15, 2024
Source: Smart MLS #24017718
Listed For Sale
$5,199,000
Jun 17, 2015
Source: Smart MLS #99095465
Sold
$4,375,000
Mar 11, 2015
Source: Agent Provided
Listed For Sale
$4,495,000

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

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Frequently asked questions about 527 Middlesex Road

  • What is 527 Middlesex Road estimated to be worth?
    Trulia's estimated value for 527 Middlesex Road in Darien, CT is $6,305,500.
  • What is the price history for 527 Middlesex Road?
    527 Middlesex Road in Darien, CT last sold for $5,320,000 in September 2024.
  • 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 527 Middlesex Road have air conditioning?
    Yes, 527 Middlesex Road in Darien, CT has air conditioning.
  • Does 527 Middlesex Road have a pool?
    Yes, 527 Middlesex Road in Darien, CT has a pool.

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