556 Middlesex Rd, Darien, CT 06820
OFF MARKET

556 Middlesex Rd
Darien, CT 06820

  • 6 Beds
  • 7 Baths
  • 5,262 sqft (on 2 acres)

$4,151,800

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $26,286/mo*
Refinance Your Home

$4,151,800

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $26,286/mo*
Refinance Your Home
6 Beds
7 Baths
5,262 sqft
(on 2 acres)

Local Information

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

Description

Fabulous colonial located on two beautiful acres offering privacy at its best all within a few minutes of town. this wonderful home was totally remodeled in 2007 boasts a formal living room with fireplace and french doors leading to a flagstone patio overlooking an expansive backyard. there is large library, a gourmet kitchen with stainless steel appliances adjacent to the family room with a fireplace, wet bar and french doors which open to the patio. Lower level includes a finished playroom and
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
No Info

Home Details for 556 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 12Types of Rooms: Recreation Room
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1954Year Updated: 2007
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price History for 556 Middlesex Rd

DatePriceEventSource
06/29/2016$2,695,000Sold
N/A
04/13/2016$2,695,000Listed For SaleAgent Provided
05/24/2011$2,550,000Sold
N/A
03/24/2011$2,775,000PendingAgent Provided
03/24/2011$2,775,000Listed For SaleAgent Provided
10/11/2010$9,500ListingRemovedAgent Provided
10/04/2010$9,500PriceChange
Agent Provided
09/26/2010$2,775,000PriceChange
Agent Provided
09/18/2010$9,500PriceChange
Agent Provided
04/10/2010$2,775,000Listed For SaleAgent Provided
08/15/2009$2,995,000ListingRemovedAgent Provided
04/05/2009$2,995,000Listed For SaleAgent Provided
07/06/2005$2,980,000Sold
N/A
03/30/1995$710,000Sold
N/A
11/22/1991$575,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$27,917
Assessment$1,803,410
Home facts updated by county records

Comparable Sales for 556 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2 Natures Way, Darien, CT
0.46
Single-Family Home
$2,750,000
06/17/25
4
4
3,815
451 Mansfield Ave, Darien, CT
0.61
Single-Family Home
$3,380,000
04/13/26
5
6
7,652
276 Mansfield Avenue, Darien, CT
0.49
Single-Family Home
$4,800,000
07/08/25
6
6
8,972
202 Mansfield Ave, Darien, CT
0.82
Single-Family Home
$2,795,000
08/21/25
6
6
6,058
26 Peach Hill Road, Darien, CT
0.50
Single-Family Home
$6,125,000
07/01/25
6
7
8,454
5 Wheat Lane, Darien, CT
0.72
Single-Family Home
$3,308,000
04/15/26
5
4
3,509
15 Allwood Road, Darien, CT
0.72
Single-Family Home
$4,550,000
07/25/25
6
5.5
6,947
23 Maplewood Drive, Darien, CT
0.80
Single-Family Home
$2,710,000
12/08/25
5
3.5
3,506
50 Buttonwood Lane, Darien, CT
0.82
Single-Family Home
$4,500,000
12/03/25
7
6.5
7,200
2 Sherry Ln, Darien, CT
0.82
Single-Family Home
$2,585,000
10/29/25
4
4.5
3,186

Assigned Schools

These are the assigned schools for 556 Middlesex Rd.
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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

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
    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
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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
    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

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Off Market Homes Near 556 Middlesex Rd

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556 Middlesex Rd, Darien, CT 06820 is a 6 bedroom, 7 bathroom, 5,262 sqft single-family home built in 1954. This property is not currently available for sale. 556 Middlesex Rd was last sold on Jun 29, 2016 for $2,695,000. The current Trulia Estimate for 556 Middlesex Rd is $4,151,800.