527 Middlesex Road, Darien, CT 06820
OFF MARKET

527 Middlesex Road
Darien, CT 06820

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

$6,015,600

Trulia Estimate
as of May 13, 2026
Est. Refi. Payment $37,960/mo*
Refinance Your Home

$6,015,600

Trulia Estimate
as of May 13, 2026
Est. Refi. Payment $37,960/mo*
Refinance Your Home
6 Beds
7 Baths
8,007 sqft
(on 2 acres)

Local Information

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

Description

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.
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 October 01, 2024

Home Highlights

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

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)
Last check for updates: about 8 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

Price History for 527 Middlesex Road

DatePriceEventSource
09/05/2024$5,320,000Sold
Smart MLS #24017718
05/24/2024$5,199,000PendingSmart MLS #24017718
05/15/2024$5,199,000Listed For SaleSmart MLS #24017718
06/17/2015$4,375,000Sold
Smart MLS #99095465
03/11/2015$4,495,000Listed For SaleAgent Provided
03/27/2013$4,495,000ListingRemovedAgent Provided
03/12/2013$4,495,000Listed For SaleAgent Provided
09/28/2009$4,100,000Sold
Smart MLS #98401530
01/30/2009$5,950,000ListingRemovedAgent Provided
11/06/2008$5,950,000Listed For SaleAgent Provided
08/16/2007$1,620,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$50,056
Assessment$3,233,580
Home facts updated by county records

Comparable Sales for 527 Middlesex Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
276 Mansfield Avenue, Darien, CT
0.42
Single-Family Home
$4,800,000
07/08/25
6
6
8,972
26 Peach Hill Road, Darien, CT
0.39
Single-Family Home
$6,125,000
07/01/25
6
7
8,454
50 Buttonwood Lane, Darien, CT
0.75
Single-Family Home
$4,500,000
12/03/25
7
6.5
7,200
15 Allwood Road, Darien, CT
0.76
Single-Family Home
$4,550,000
07/25/25
6
5.5
6,947
92 Half Mile Road, Darien, CT
0.69
Single-Family Home
$7,400,000
05/29/25
6
7.5
10,829
202 Mansfield Ave, Darien, CT
0.73
Single-Family Home
$2,795,000
08/21/25
6
6
6,058
1 Fox Hill Lane, Darien, CT
0.65
Single-Family Home
$4,500,000
08/12/25
4
4.5
5,561
48 Dorchester Road, Darien, CT
0.94
Single-Family Home
$5,295,000
07/22/25
5
6
6,242

Assigned Schools

These are the assigned schools for 527 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

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
    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
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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
    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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527 Middlesex Road, Darien, CT 06820 is a 6 bedroom, 8 bathroom, 8,007 sqft single-family home built in 2008. This property is not currently available for sale. 527 Middlesex Road was last sold on Sep 5, 2024 for $5,320,000 (2% higher than the asking price of $5,199,000). The current Trulia Estimate for 527 Middlesex Road is $6,015,600.