537 Middlesex Rd, Darien, CT 06820
OFF MARKET

537 Middlesex Rd
Darien, CT 06820

  • 5 Beds
  • 4 Baths
  • 3,300 sqft (on 0.59 acres)

$1,463,400

Trulia Estimate
as of May 12, 2026
Est. Refi. Payment $9,291/mo*
Refinance Your Home

$1,463,400

Trulia Estimate
as of May 12, 2026
Est. Refi. Payment $9,291/mo*
Refinance Your Home
5 Beds
4 Baths
3,300 sqft
(on 0.59 acres)

Homes for sale near 537 Middlesex Rd

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Apartments for Rent

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Local Information

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

Description

Price reflects new assessment. Circa 1780 ''Middlesex Cottage''. Charming vintage home with surprising living room and cathedral ceiling family room. Maturely landscaped property directly across from Ox Ridge Hunt Club, great opportunity.
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 only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 537 Middlesex Rd

Interior Features

Interior Details
BasementNumber of Rooms: 10Ceiling Fan
Heating & Cooling
Heating: Other, OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDisposalRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1920
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 0.59 acres

Price History for 537 Middlesex Rd

DatePriceEventSource
04/30/2019$805,000Sold
Smart MLS #170155802
01/14/2019$895,000PriceChange
Agent Provided
09/26/2018$1,095,000PriceChange
Agent Provided
06/11/2018$1,195,000PriceChange
Agent Provided
05/21/2018$1,249,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$9,082
Assessment$586,670
Home facts updated by county records

Comparable Sales for 537 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2 Natures Way, Darien, CT
0.49
Single-Family Home
$2,750,000
06/17/25
4
4
3,815
2 Knollwood Lane, Darien, CT
0.93
Single-Family Home
$2,300,000
08/19/25
4
3.5
3,678
49 Salisbury Rd, Darien, CT
0.81
Single-Family Home
$2,865,000
04/20/26
5
4.5
4,000
6 Fox Hill Ln, Darien, CT
0.68
Single-Family Home
$4,000,000
08/11/25
5
5
5,330
489 Hoyt Street, Darien, CT
1.03
Single-Family Home
$1,600,000
11/10/25
4
2.5
3,630
37 Salisbury Road, Darien, CT
0.85
Single-Family Home
$2,795,000
08/11/25
4
3.5
3,261
8 Leeds Lane, Darien, CT
1.05
Single-Family Home
$2,237,500
11/03/25
4
2.5
3,777
23 Maplewood Drive, Darien, CT
0.86
Single-Family Home
$2,710,000
12/08/25
5
3.5
3,506
5 Wheat Lane, Darien, CT
0.75
Single-Family Home
$3,308,000
04/15/26
5
4
3,509
4 Rabbit Lane, Darien, CT
1.06
Single-Family Home
$2,675,000
08/11/25
5
3.5
3,690

Assigned Schools

These are the assigned schools for 537 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

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
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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
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  • 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!"
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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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Homes for rent near 537 Middlesex Rd

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Off Market Homes Near 537 Middlesex Rd

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Explore by feature

537 Middlesex Rd, Darien, CT 06820 is a 5 bedroom, 4 bathroom, 3,300 sqft single-family home built in 1920. This property is not currently available for sale. 537 Middlesex Rd was last sold on Apr 30, 2019 for $805,000. The current Trulia Estimate for 537 Middlesex Rd is $1,463,400.