259 Middlesex Road, Darien, CT 06820
OFF MARKET

259 Middlesex Road
Darien, CT 06820

  • 6 Beds
  • 8 Baths
  • 8,552 sqft (on 1.06 acres)

$6,563,300

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $42,886/mo*
Refinance Your Home

$6,563,300

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $42,886/mo*
Refinance Your Home
6 Beds
8 Baths
8,552 sqft
(on 1.06 acres)

Home Value

Trulia Estimate
$6.56M
Since last month
Increased$12K (+0.2%)
Since last year
Increased$349K (+5.6%)
Since last sale
Increased$449K (+7.4%)
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 +561% in the last 10 years
MonthEstimated value
2026
August 2026$6.55M
July 2026$6.54M
June 2026$6.49M
May 2026$6.45M
April 2026$6.35M
March 2026$6.36M
February 2026$6.36M
January 2026$6.24M
2025
2023
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
0.31
Single-Family Home
$4,750,000
06/22/26
6
5
6,810
10 Stony Brook Rd, Darien, CT
0.52
Single-Family Home
$5,660,000
04/14/26
6
7.5
8,680
43 Stony Brook Rd, Darien, CT
0.35
Single-Family Home
$3,775,000
06/23/26
5
6.5
7,200
300 Hollow Tree Ridge Road, Darien, CT
0.43
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
261 Hollow Tree Ridge Road, Darien, CT
0.45
Single-Family Home
$4,350,000
12/15/25
5
5.5
6,135
6 Old Parish Road, Darien, CT
0.19
Single-Family Home
$3,550,000
06/12/26
4
4.5
4,825
16 Libby Lane, Darien, CT
0.12
Single-Family Home
$2,976,000
06/24/26
4
4.5
2,928
130 West Avenue, Darien, CT
0.42
Single-Family Home
$2,800,000
12/31/25
6
5.5
6,794

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
253 Middlesex Road, Darien, CT 06820
0.03
$5,778,400
5
5.5
9,033
Off Market
5 Shields Lane, Darien, CT 06820
0.13
$4,602,000
4
6
4,748
Recently Sold
16 Parsons Walk, Darien, CT 06820
0.14
$5,060,300
6
7.5
6,643
Off Market
16 Libby Lane, Darien, CT 06820
0.12
$2,976,000
4
4.5
2,928
Recently Sold
25 Libby Lane, Darien, CT 06820
0.14
$4,603,800
5
6
5,545
Off Market
10 Holly Lane, Darien, CT 06820
0.16
$4,748,000
5
6
6,012
Off Market
223 Middlesex Road, Darien, CT 06820
0.18
$1,540,000
3
1.5
1,840
Recently Sold
6 Old Parish Road, Darien, CT 06820
0.19
$3,550,000
4
4.5
4,825
Recently Sold
3 Revere Road, Darien, CT 06820
0.18
$2,350,000
5
3
3,395
Recently Sold
14 Revere Road, Darien, CT 06820
0.19
$3,250,000
5
5.5
5,226
Recently Sold
2 Old Parish Road, Darien, CT 06820
0.20
$3,220,900
5
3.5
4,553
Off Market

Local Information

  • Map ViewExplore the area around 259 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
2024
Lot Size
1.06 acres
Living Area
8,552 sqft
Price/Sqft
$767
Parking
3 Car Garage

About this House

Discover the epitome of luxury living in this newly constructed 8,552 square foot home, meticulously designed to cater to a sophisticated lifestyle. Nestled within easy access to Darien and Noroton Heights train stations, this residence offers a seamless commute to New York City, blending convenience with upscale suburbia.The heart of the home, an exquisitely appointed chef's kitchen, features Subzero / Wolf appliances, a generous island, and a Julian workstation sink - sure to delight culinary enthusiasts. Luxury resonates in the primary suite, a sanctuary embellished with a vaulted ceiling, limestone FP, two stunning closets, and two lavish bathrooms. Every bedroom in this six-bedroom abode is an ensuite, promising personal retreats for all. Entertain and unwind in your outdoor oasis, complete with exquisite stone work, a Gunite pool with a spa, an outdoor kitchen area, and dual patios - one covered with an architectural stone fireplace, the other featuring a cozy gas fire-pit. Working from home is a pleasure in the dedicated office complete with a fireplace, French doors and a bar. Venture down to the lower level where a family room equipped with a fireplace, bedroom and full bath awaits. Six fireplaces, impeccable millwork, designer lighting, and high-efficiency mechanicals elevate this property into a league of its own. With its blend of extraordinary craftsmanship and prime location, this home isn't just a statement-it's a conversation starter. (taxes TBD)
259 Middlesex Road, Darien, CT 06820 is a 6 bedroom, 9 bathroom, 8,552 sqft single-family home built in 2024. It last sold for $6,100,000 on Mar 26, 2025 (6% below the $6,470,000 asking price). It is currently off market. The Trulia Estimate is $6,563,300, with a rent estimate of $7,253/month.
Last check for updates: about 1 hour ago
Listed by Diane Dupont, (203) 506-4218
William Pitt Sotheby's Int'l, (203) 245-6700
Bought with: Stephanie O'Grady, (561) 504-5504, Houlihan Lawrence, (203) 655-8238
Source: Smart MLS, MLS#24048979

Home Details for 259 Middlesex Road

Interior Features

Interior Details
Basement: Full,Heated,Cooled,Partially Finished,Liveable SpaceNumber of Rooms: 14Types of Rooms: Master Bedroom, Bedroom, Dining Room, Great Room, Kitchen, Library, Office, Other, Rec Play Room
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 9Number of Bathrooms (full): 7Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 8552 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Gas Cooktop, Oven, Microwave, Range Hood, Freezer, Subzero, Dishwasher, Disposal, Washer, Dryer, Wine Cooler, Water Heater, Tankless Water HeaterDishwasherDisposalDryerLaundry: Upper Level,Mud RoomMicrowaveWasher
Heating & Cooling
Heating: Hydro Air,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hydro Air
Fireplace & Spa
Number of Fireplaces: 6Spa: HeatedHas a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane WindowsDoor: French Doors
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Patio, Porch, CoveredExterior: Lighting, Garden, Stone Wall, Underground SprinklerFoundation: Concrete PerimeterGardenHas 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, Heated, Pool/Spa Combo, Alarm, Salt Water, In GroundPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 6952 Square FeetFinished Area (below surface): 1600 Square Feet

Property Information

Year Built
Year Built: 2024
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Farm House
Building
Construction Materials: Cedar, Stone, Metal SidingIncludes Home Warranty
Property Information
Condition: Completed/Never OccupiedParcel Number: 103874

Price & Status

Price
List Price: $6,470,000
Status Change & Dates
Off Market Date: Thu Jan 16 2025Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: Darien
School Information
Elementary School: Ox RidgeJr High / Middle School: Per Board of EdHigh School: Darien

Building

Building Area
Building Area: 8552 Square Feet

Community

Community Features: Golf, Library, Medical Facilities, Paddle Tennis, Public Rec Facilities, Shopping/Mall, Stables/Riding, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 1.06 Acres

Energy

Energy Efficiency Features: Insulation, Thermostat, Windows

Miscellaneous

BasementMls Number: 24048979Attic: Floored, Walk-upAbove Grade Unfinished Area: 6952

Additional Information

GolfLibraryMedical FacilitiesPaddle TennisPublic Rec FacilitiesShopping/MallStables/RidingTennis Court(s)

Price and Tax history

DateEventPrice
Mar 26, 2025
Source: Smart MLS #24048979
Sold
$6,100,000
Jan 18, 2025
Source: Smart MLS #24048979
Pending
$6,470,000
Nov 1, 2024
Source: Smart MLS #24048979
Listed For Sale
$6,470,000
Jan 31, 2022
Source: Smart MLS #170456783
Sold
$1,490,000
Jan 14, 2022
Source: Smart MLS #170456783
Contingent
$1,490,000

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

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Frequently asked questions about 259 Middlesex Road

  • What is 259 Middlesex Road estimated to be worth?
    Trulia's estimated value for 259 Middlesex Road in Darien, CT is $6,563,300.
  • What is the price history for 259 Middlesex Road?
    259 Middlesex Road in Darien, CT last sold for $6,100,000 in March 2025.
  • 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 259 Middlesex Road have air conditioning?
    Yes, 259 Middlesex Road in Darien, CT has air conditioning.
  • Does 259 Middlesex Road have a pool?
    Yes, 259 Middlesex Road in Darien, CT has a pool.

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