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)

$5,778,400

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $37,767/mo*
Refinance Your Home

$5,778,400

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $37,767/mo*
Refinance Your Home
5 Beds
5.5 Baths
9,033 sqft
(on 1.05 acres)

Home Value

Trulia Estimate
$5.78M
Since last month
Decreased$124K (-2.1%)
Since last year
Increased$355K (+6.5%)
Since last sale
Increased$1M (+31.4%)
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 +58% in the last 10 years
MonthEstimated value
2026
August 2026$5.78M
July 2026$5.9M
June 2026$5.96M
May 2026$5.93M
April 2026$5.73M
March 2026$5.84M
February 2026$5.6M
January 2026$5.61M
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
8 Haskell Ln, Darien, CT
0.28
Single-Family Home
$4,750,000
06/22/26
6
5
6,810
43 Stony Brook Rd, Darien, CT
0.38
Single-Family Home
$3,775,000
06/23/26
5
6.5
7,200
261 Hollow Tree Ridge Road, Darien, CT
0.42
Single-Family Home
$4,350,000
12/15/25
5
5.5
6,135
16 Libby Lane, Darien, CT
0.09
Single-Family Home
$2,976,000
06/24/26
4
4.5
2,928
6 Old Parish Road, Darien, CT
0.22
Single-Family Home
$3,550,000
06/12/26
4
4.5
4,825
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
14 Revere Road, Darien, CT
0.16
Single-Family Home
$3,250,000
08/07/26
5
5.5
5,226

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
259 Middlesex Road, Darien, CT 06820
0.03
$6,563,300
6
8
8,552
Off Market
16 Libby Lane, Darien, CT 06820
0.09
$2,976,000
4
4.5
2,928
Recently Sold
5 Shields Lane, Darien, CT 06820
0.13
$4,602,000
4
6
4,748
Recently Sold
223 Middlesex Road, Darien, CT 06820
0.15
$1,540,000
3
1.5
1,840
Recently Sold
3 Revere Road, Darien, CT 06820
0.15
$2,350,000
5
3
3,395
Recently Sold
25 Libby Lane, Darien, CT 06820
0.13
$4,603,800
5
6
5,545
Off Market
14 Revere Road, Darien, CT 06820
0.16
$3,250,000
5
5.5
5,226
Recently Sold
16 Parsons Walk, Darien, CT 06820
0.16
$5,060,300
6
7.5
6,643
Off Market
311 Noroton Avenue, Darien, CT 06820
0.20
$3,550,000
5
5.5
5,356
Recently Sold
10 Holly Lane, Darien, CT 06820
0.17
$4,748,000
5
6
6,012
Off Market
6 Bouton Lane, Darien, CT 06820
0.21
$3,462,000
6
8
6,233
Off Market

Local Information

  • Map ViewExplore the area around 253 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
2007
Lot Size
1.05 acres
Living Area
9,033 sqft
Price/Sqft
$640
Parking
5 Car Garage

About this House

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.
253 Middlesex Road, Darien, CT 06820 is a 5 bedroom, 6 bathroom, 9,033 sqft single-family home built in 2007. It last sold for $4,398,000 on Aug 12, 2024 (2% below the $4,475,000 asking price). It is currently off market. The Trulia Estimate is $5,778,400, with a rent estimate of $25,238/month.
Last check for updates: about 8 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

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

Price and Tax history

DateEventPrice
Aug 12, 2024
Source: Smart MLS #24000108
Sold
$4,398,000
Apr 19, 2024
Source: Smart MLS #24000108
Pending
$4,475,000
Apr 3, 2024
Source: Smart MLS #24000108
Listed For Sale
$4,475,000
Aug 4, 2014
Source: Smart MLS #99066064
Sold
$3,700,000
May 23, 2014
Source: Agent Provided
Listed For Sale
$3,825,000

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 253 Middlesex Road

  • What is 253 Middlesex Road estimated to be worth?
    Trulia's estimated value for 253 Middlesex Road in Darien, CT is $5,778,400.
  • What is the price history for 253 Middlesex Road?
    253 Middlesex Road in Darien, CT last sold for $4,398,000 in August 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 253 Middlesex Road have air conditioning?
    Yes, 253 Middlesex Road in Darien, CT has air conditioning.
  • Does 253 Middlesex Road have a pool?
    Yes, 253 Middlesex Road in Darien, CT has a pool.

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