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)

$5,231,800

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $34,174/mo*
Refinance Your Home

$5,231,800

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $34,174/mo*
Refinance Your Home
5 Beds
6 Baths
5,492 sqft
(on 2.92 acres)

Home Value

Trulia Estimate
$5.23M
Since last month
Increased$12K (+0.2%)
Since last year
Increased$438K (+9.1%)
Since last sale
Increased$2M (+87%)
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 +38% in the last 10 years
MonthEstimated value
2026
August 2026$5.24M
July 2026$5.22M
June 2026$5.27M
May 2026$5.13M
April 2026$5.11M
March 2026$5.09M
February 2026$4.89M
January 2026$4.8M
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
23 Fox Hill Ln, Darien, CT
0.20
Single-Family Home
$7,523,000
07/15/26
5
5.5
7,400
21 Fox Hill Ln, Darien, CT
0.25
Single-Family Home
$4,597,500
06/29/26
5
6.5
6,308
561 Middlesex Road, Darien, CT
0.51
Single-Family Home
$2,800,000
08/10/26
4
3.5
3,411
202 Mansfield Ave, Darien, CT
0.62
Single-Family Home
$2,795,000
08/21/25
6
6
6,058
174 Leroy Avenue, Darien, CT
0.67
Single-Family Home
$4,475,000
08/17/26
5
4.5
5,506
6 Priscilla Lane, Darien, CT
0.52
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
316 Mansfield Avenue, Darien, CT
0.56
Single-Family Home
$5,625,000
07/24/26
5
6
9,039
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
58 Knollwood Lane, Darien, CT
0.56
Single-Family Home
$3,750,000
07/23/26
8
6
5,658

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
460 Middlesex Road, Darien, CT 06820
0.10
$7,500,000
5
7
10,213
For Sale
100 Hanson Road, Darien, CT 06820
0.20
$3,919,700
5
4.5
4,804
Off Market
22 Linda Lane, Darien, CT 06820
0.25
$3,641,500
4
3.5
3,943
Off Market
21 Fox Hill Ln, Darien, CT 06820
0.25
$4,597,500
5
6.5
6,308
Recently Sold
11 Linda Lane, Darien, CT 06820
0.27
$4,328,600
5
5
5,182
Off Market
114 Hanson Road, Darien, CT 06820
0.28
$3,905,300
5
7
4,786
Off Market
26 Peach Hill Road, Darien, CT 06820
0.27
$6,524,700
6
7
8,454
Off Market
527 Middlesex Road, Darien, CT 06820
0.33
$6,305,500
6
7
8,007
Off Market
24 Saddle Ridge Road, Darien, CT 06820
0.35
$4,743,000
5
6
6,546
Off Market
60 Hanson Road, Darien, CT 06820
0.38
$3,627,700
4
4.5
4,446
Off Market
19 Blueberry Lane, Darien, CT 06820
0.39
$3,711,000
4
2.5
3,881
Recently Sold
5 Fox Hill Lane, Darien, CT 06820
0.50
$3,781,500
5
4.5
4,900
Off Market

Local Information

  • Map ViewExplore the area around 459 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1988
Lot Size
2.92 acres
Living Area
5,492 sqft
Price/Sqft
$953
Parking
Garage

About this House

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.
459 Middlesex Rd, Darien, CT 06820 is a 5 bedroom, 7 bathroom, 5,492 sqft single-family home built in 1988. It last sold for $2,800,000 on Feb 22, 2018. It is currently off market. The Trulia Estimate is $5,231,800, with a rent estimate of $23,400/month.

Home Details for 459 Middlesex Rd

Interior Features

Interior Details
BasementNumber of Rooms: 12
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
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 and Tax history

DateEventPrice
Feb 22, 2018
Source: Smart MLS #99172740
Sold
$2,800,000
Jun 1, 2017
Source: Agent Provided
PriceChange
$3,295,000
Price decreased by 4%
Oct 20, 2016
Source: Agent Provided
PriceChange
$3,450,000
Price decreased by 13%
Apr 1, 2016
Source: Agent Provided
PriceChange
$3,950,000
Price decreased by 7%
Jan 19, 2016
Source: Agent Provided
Listed For Sale
$4,250,000

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

Frequently asked questions about 459 Middlesex Rd

  • What is 459 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 459 Middlesex Rd in Darien, CT is $5,231,800.
  • What is the price history for 459 Middlesex Rd?
    459 Middlesex Rd in Darien, CT last sold for $2,800,000 in February 2018.
  • 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.
  • How big is the lot at 459 Middlesex Rd?
    The lot at 459 Middlesex Rd in Darien, CT is about 2.9 acres.
  • Does 459 Middlesex Rd have a garage?
    Yes, 459 Middlesex Rd in Darien, CT has a garage.

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Off Market Homes Near 459 Middlesex Rd

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