459 Middlesex Rd, Darien, CT 06820
OFF MARKET

459 Middlesex Rd
Darien, CT 06820

  • 5 Beds
  • 6 Baths
  • 5,492 sqft (on 2.92 acres)

$5,097,900

Trulia Estimate
as of Jun 10, 2026
Est. Refi. Payment $32,765/mo*
Refinance Your Home

$5,097,900

Trulia Estimate
as of Jun 10, 2026
Est. Refi. Payment $32,765/mo*
Refinance Your Home
5 Beds
6 Baths
5,492 sqft
(on 2.92 acres)

Local Information

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

Description

Classic Wee Burn Golf Course location, unfettered views of sunsets, ponds and rolling fairways yet three minutes to school and five minutes to the train and town. Tastefully maintained and perfectly presented on nearly three acres, this five bedroom home with all en suite baths boasts 5,500 square feet. Gracious formal rooms, cozy study, four fireplaces and updates throughout. Fantastic flow for entertaining, plus large terrace overlooking the private professionally landscaped grounds. Large unfinished lower level room for gym ,wine cellar play room. Your home for a generation at an incredible value.Updated A/C system 2017.
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.

Home Highlights

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

Home Details for 459 Middlesex Rd

Interior Features

Interior Details
BasementNumber of Rooms: 12
Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: OtherPatio
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 2.92 acres

Price History for 459 Middlesex Rd

DatePriceEventSource
02/22/2018$2,800,000Sold
Smart MLS #99172740
06/01/2017$3,295,000PriceChange
Agent Provided
10/20/2016$3,450,000PriceChange
Agent Provided
04/01/2016$3,950,000PriceChange
Agent Provided
01/19/2016$4,250,000Listed For SaleAgent Provided
12/20/1989$1,912,000Sold
N/A

Market trends in Darien

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
14MoM
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Property Tax and Assessment

Year2025
Tax$37,760
Assessment$2,439,290
Home facts updated by county records

Homeowner tools

Estimated monthly rent$23,400/mo
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Homes for rent near 459 Middlesex Rd

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Comparable Sales for 459 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
26 Peach Hill Road, Darien, CT
0.27
Single-Family Home
$6,125,000
07/01/25
6
7
8,454
6 Fox Hill Ln, Darien, CT
0.51
Single-Family Home
$4,000,000
08/11/25
5
5
5,330
202 Mansfield Ave, Darien, CT
0.62
Single-Family Home
$2,795,000
08/21/25
6
6
6,058
1 Fox Hill Lane, Darien, CT
0.54
Single-Family Home
$4,500,000
08/12/25
4
4.5
5,561
6 Priscilla Lane, Darien, CT
0.52
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
19 Blueberry Lane, Darien, CT
0.39
Single-Family Home
$3,711,000
06/03/26
4
2.5
3,881
6 Cloudy Lane, Darien, CT
0.84
Single-Family Home
$4,500,000
05/29/26
5
5
5,864
276 Mansfield Avenue, Darien, CT
0.50
Single-Family Home
$4,800,000
07/08/25
6
6
8,972
5 Wheat Lane, Darien, CT
0.82
Single-Family Home
$3,308,000
04/15/26
5
4
3,509
15 Allwood Road, Darien, CT
0.86
Single-Family Home
$4,550,000
07/25/25
6
5.5
6,947

Nearby homes

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Assigned Schools

These are the assigned schools for 459 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

  • 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 "
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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
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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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Homes for sale near 459 Middlesex Rd

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Off Market Homes Near 459 Middlesex Rd

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459 Middlesex Rd, Darien, CT 06820 is a 5 bedroom, 7 bathroom, 5,492 sqft single-family home built in 1988. This property is not currently available for sale. 459 Middlesex Rd was last sold on Feb 22, 2018 for $2,800,000. The current Trulia Estimate for 459 Middlesex Rd is $5,097,900.