444 Middlesex Rd, Darien, CT 06820
OFF MARKET

444 Middlesex Rd
Darien, CT 06820

  • 4 Beds
  • 4 Baths
  • 3,051 sqft (on 2.10 acres)

$2,395,000

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $15,521/mo*
Refinance Your Home

$2,395,000

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $15,521/mo*
Refinance Your Home
4 Beds
4 Baths
3,051 sqft
(on 2.10 acres)

Local Information

  • Map ViewExplore the area around 444 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

PART OF THE ORIGINAL ALTHEA FARM ESTATE NESTLED ON A TWO ACRE HILLSIDE. TWO STORY VAULTED, WOOD-BEAMED FOYER, STEP DOWN LIVING ROOM WITH 10' WOOD-BEAM CEILING PLUS ORIGINAL FIELD STONE FIREPLACE. OPEN KITCHEN AND FAMILY ROOM. WIDE PLANK FLOORING, WRAP AROUND DECK WITH STEP DOWN BRICK PATIO. PROPERTY INCLUDES ORIGINAL ESTATE FIELDSTONE "PUMP HOUSE" SET BACK ON UPPER HILLSIDE - A GENUINE SYMBOL OF AN ERA GONE BY. 1+ATTACHED GARAGE.
444 Middlesex Rd, Darien, CT 06820 is a 4 bedroom, 4 bathroom, 3,051 sqft single-family home built in 1910. It last sold for $1,148,750 on Aug 9, 2010. It is currently off market. The Trulia Estimate is $2,395,000, with a rent estimate of $16,000/month.

Home Highlights

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

Home Details for 444 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 8
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Exterior Features

Exterior Home Features
DeckExterior: WoodPatio
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 2.10 acres

Price History for 444 Middlesex Rd

DatePriceEventSource
08/09/2010$1,148,750Sold
N/A
07/14/2010$1,197,500Listed For SaleAgent Provided
06/09/2010$1,197,500ListingRemovedAgent Provided
05/23/2010$1,197,500Listed For SaleAgent Provided
06/18/2003$1,075,000Sold
Smart MLS #98154723
10/28/1992$575,000Sold
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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$15,165
Assessment$979,650
Home facts updated by county records

Comparable Sales for 444 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
217 Mansfield Avenue, Darien, CT
0.41
Single-Family Home
$2,250,000
05/29/26
3
2.5
2,760
19 Blueberry Lane, Darien, CT
0.50
Single-Family Home
$3,711,000
06/03/26
4
2.5
3,881
21 Fox Hill Ln, Darien, CT
0.11
Single-Family Home
$4,597,500
06/29/26
5
6.5
6,308
2 Knollwood Lane, Darien, CT
0.60
Single-Family Home
$2,300,000
08/19/25
4
3.5
3,678
6 Fox Hill Ln, Darien, CT
0.37
Single-Family Home
$4,000,000
08/11/25
5
5
5,330
26 Holly Lane, Darien, CT
0.73
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
1 Fox Hill Lane, Darien, CT
0.41
Single-Family Home
$4,500,000
08/12/25
4
4.5
5,561
178 Christie Hill Road, Darien, CT
0.94
Single-Family Home
$2,150,000
07/31/25
4
4.5
3,436
6 Priscilla Lane, Darien, CT
0.41
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
267 Brookside Road, Darien, CT
1.00
Single-Family Home
$2,850,000
05/29/26
4
3.5
3,416

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 444 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
    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

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

Explore by feature - Garage

18 rentals with a garage in Darien, CT

Explore by feature - Air Conditioning

21 rentals with air conditioning in Darien, CT

Explore by feature - Pool

Explore by feature - Washer/dryer

24 rentals with a washer/dryer in Darien, CT

Explore by feature - Outdoor Space

6 rentals with an outdoor space in Darien, CT

Homes for sale near 444 Middlesex Rd

Skip to last item
Skip to first item

Off Market Homes Near 444 Middlesex Rd

Skip to last item
Skip to first item