253 Middlesex Road, Darien, CT 06820
OFF MARKET

253 Middlesex Road
Darien, CT 06820

  • 5 Beds
  • 5.5 Baths
  • 9,033 sqft (on 1.05 acres)

$5,854,500

Trulia Estimate
as of May 23, 2026
Est. Refi. Payment $37,800/mo*
Refinance Your Home

$5,854,500

Trulia Estimate
as of May 23, 2026
Est. Refi. Payment $37,800/mo*
Refinance Your Home
5 Beds
5.5 Baths
9,033 sqft
(on 1.05 acres)

Local Information

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

Description

Welcome to luxury living at its finest! This impressive stone and shingle home redefines sophistication with meticulous craftsmanship and attention to detail. Nestled in the most convenient location, close to Schools, Metro-North, Darien Commons & all town amenities, offering the ultimate in lifestyle & convenience. Step inside to discover a world of elegance, where natural light floods the interiors, creating a warm & inviting atmosphere featuring custom millwork, soaring ceilings and fine details throughout. Entertain with style in the gourmet eat-in kitchen with a large island and butler's pantry, perfect for hosting gatherings of all sizes. French doors lead from the kitchen and living areas to covered porches, inviting you to bask in the serene views of the sparkling pool and lush surroundings. The main house boasts impeccable formal rooms and 5 spacious bedrooms, each with en suite baths, offering comfort and privacy for the entire family. 3-finished floors of living space, plus the bonus of a stunning separate structure featuring a private studio/office space with a cozy fireplace & cathedral ceiling paired with an additional two-car garage making a total of 5 garage spaces with Tesla charging station. The separate studio offers endless possibilities, be it a home office, artist's sanctuary, or private retreat. Experience the pinnacle of stone & shingle style living, from cozy family nights to grand celebrations, every moment will be cherished in this stunning home.
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
5 Car Garage
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 253 Middlesex Road

Interior Features

Interior Details
Basement: Full,Heated,Storage Space,Cooled,Interior Entry,Partially FinishedNumber of Rooms: 16Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Great Room, Kitchen, Library, Living Room, Rec Play Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 9033 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Gas Range, Oven, Microwave, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Forced Air,Radiant,Zoned,Oil,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 5Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane WindowsDoor: French Doors
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: WoodPatio / Porch: Covered, PatioFencing: PartialOther Structures: Guest House, Pool HouseExterior: Balcony, Rain Gutters, Stone Wall, Underground SprinklerFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 5Number of Covered Spaces: 5No CarportHas a GarageHas an Attached GarageParking Spaces: 5Parking: Attached,Garage Door Opener
Pool
Pool: Gunite, Heated, Pool/Spa Combo, In GroundPool
Frontage
Waterfront: Beach AccessNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 7933 Square FeetFinished Area (below surface): 1100 Square Feet

Property Information

Year Built
Year Built: 2007
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Shingle Siding, Stone, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Not Included in Sale: See AddendumParcel Number: 103873

Price & Status

Price
List Price: $4,475,000
Status Change & Dates
Off Market Date: Fri Apr 19 2024Possession Timing: Negotiable

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: 9033 Square Feet

Community

Community Features: Library, Medical Facilities, Park, Playground, Public Rec Facilities, Near Public Transport, Shopping/Mall
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 1.05 Acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24000108Attic: Walk-upAbove Grade Unfinished Area: 7933

Additional Information

LibraryMedical FacilitiesParkPlaygroundPublic Rec FacilitiesNear Public TransportShopping/Mall
Last check for updates: about 4 hours ago
Listed by Taylor Tait, (203) 644-0026
Houlihan Lawrence, (203) 966-3507
Bought with: Stephanie Hanford, (917) 499-5402, Compass Connecticut, LLC, (203) 423-3100
Source: Smart MLS, MLS#24000108

Price History for 253 Middlesex Road

DatePriceEventSource
08/12/2024$4,398,000Sold
Smart MLS #24000108
04/19/2024$4,475,000PendingSmart MLS #24000108
04/03/2024$4,475,000Listed For SaleSmart MLS #24000108
08/04/2014$3,700,000Sold
Smart MLS #99066064
05/23/2014$3,825,000Listed For SaleAgent Provided
03/05/2007$1,200,000Sold
N/A
07/30/1992$305,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$46,609
Assessment$3,010,910
Home facts updated by county records

Comparable Sales for 253 Middlesex Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
25 Libby Lane, Darien, CT
0.13
Single-Family Home
$4,325,000
07/29/25
5
6
5,545
261 Hollow Tree Ridge Road, Darien, CT
0.42
Single-Family Home
$4,350,000
12/15/25
5
5.5
6,135
12 Kona Road, Darien, CT
0.52
Single-Family Home
$4,400,000
05/29/25
5
6.5
6,805
300 Hollow Tree Ridge Road, Darien, CT
0.40
Single-Family Home
$4,900,000
09/02/25
5
7
6,118
5 Shields Lane, Darien, CT
0.13
Single-Family Home
$4,602,000
05/01/26
4
6
4,748
311 Noroton Avenue, Darien, CT
0.20
Single-Family Home
$3,550,000
12/17/25
5
5.5
5,356
26 Holly Lane, Darien, CT
0.18
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
326 Hollow Tree Ridge Road, Darien, CT
0.47
Single-Family Home
$3,650,000
08/20/25
5
4.5
6,860
29 Stony Brook Road, Darien, CT
0.41
Single-Family Home
$4,200,000
07/14/25
4
4.5
5,308

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Assigned Schools

These are the assigned schools for 253 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
    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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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.

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253 Middlesex Road, Darien, CT 06820 is a 5 bedroom, 6 bathroom, 9,033 sqft single-family home built in 2007. This property is not currently available for sale. 253 Middlesex Road was last sold on Aug 12, 2024 for $4,398,000 (2% lower than the asking price of $4,475,000). The current Trulia Estimate for 253 Middlesex Road is $5,854,500.