340 Middlesex Rd, Darien, CT 06820
Property image
Property image
OFF MARKET

340 Middlesex Rd
Darien, CT 06820

  • 6 Beds
  • 7 Baths
  • 6,554 sqft (on 4.48 acres)

$5,213,400

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $33,697/mo*
Refinance Your Home

$5,213,400

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $33,697/mo*
Refinance Your Home
6 Beds
7 Baths
6,554 sqft
(on 4.48 acres)

Local Information

  • Map ViewExplore the area around 340 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This magnificent 4.5 acre country estate sits atop a rolling hillside enhanced by a lovely pond and beautifully landscaped grounds. Built in 1906 as a carriage house, the owners maintained much of the original charm, character and architecture throughout major renovations. Features include hardwood and brick flooring, open spiral staircase with wrought iron railings, three-story turret, gourmet kitchen and 3 fpls with antique mantels. Large media/game room, solarium, screened porch, gym, indoor spa room and a heated 3 car garage. The roman-style gunite pool is the focal point of the back yard. Separate guesthouse with studio/office, pool cabana, 2 full baths and heated 2 car garage. Classic Turf tennis court with lights for evening play.
340 Middlesex Rd, Darien, CT 06820 is a 6 bedroom, 7 bathroom, 6,554 sqft single-family home built in 1906. It last sold for $300,000 on Oct 1, 2018. It is currently off market. The Trulia Estimate is $5,213,400, with a rent estimate of $23,382/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 340 Middlesex Rd

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 12Types of Rooms: Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Recreation Room, Solarium AtriumWet Bar
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: ShingleLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1906Year Updated: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 4.48 acres

Mobile R/V

RV Parking
Rv Parking

Building

Fitness & Sports
Basketball CourtTennis Court
Pool
Sauna

Additional Information

Intercom

Price History for 340 Middlesex Rd

DatePriceEventSource
10/01/2018$300,000Sold
N/A
12/31/2012$2,900,000Sold
Smart MLS #98523383
09/04/2012$3,650,000PriceChange
Agent Provided
03/16/2012$3,870,000PriceChange
Agent Provided
01/01/2012$3,970,000PriceChange
Agent Provided
04/10/2011$4,150,000PriceChange
Agent Provided
03/20/2011$4,250,000PriceChange
Agent Provided
12/04/2010$4,350,000PriceChange
Agent Provided
09/29/2010$4,480,000PriceChange
Agent Provided
06/25/2010$4,650,000PriceChange
Agent Provided
05/08/2010$4,850,000Listed For SaleAgent Provided
08/02/1995$942,500Sold
N/A

Market trends in Darien

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.73M
Sale-to-List Price
105.6%
Price per sq ft
$787
Available listings
54
11MoM
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Property Tax and Assessment

Year2025
Tax$34,576
Assessment$2,233,560
Home facts updated by county records

Comparable Sales for 340 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
54 Stony Brook Rd, Darien, CT
0.28
Single-Family Home
$4,425,000
08/04/25
6
6
6,446
6 Priscilla Lane, Darien, CT
0.20
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
43 Stony Brook Rd, Darien, CT
0.33
Single-Family Home
$3,775,000
06/23/26
5
6.5
7,200
25 Libby Lane, Darien, CT
0.42
Single-Family Home
$4,325,000
07/29/25
5
6
5,545
21 Fox Hill Ln, Darien, CT
0.46
Single-Family Home
$4,597,500
06/29/26
5
6.5
6,308
10 Stony Brook Rd, Darien, CT
0.48
Single-Family Home
$5,660,000
04/14/26
6
7.5
8,680
6 Old Parish Road, Darien, CT
0.37
Single-Family Home
$3,550,000
06/12/26
4
4.5
4,825
202 Mansfield Ave, Darien, CT
0.64
Single-Family Home
$2,795,000
08/21/25
6
6
6,058
130 West Avenue, Darien, CT
0.59
Single-Family Home
$2,800,000
12/31/25
6
5.5
6,794
26 Holly Lane, Darien, CT
0.37
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260

Nearby homes

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Assigned Schools

These are the assigned schools for 340 Middlesex Rd.
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

  • 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
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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 "
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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
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  • dwenger
    "Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 340 Middlesex Rd

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Off Market Homes Near 340 Middlesex Rd

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