580 Middlesex Rd, Darien, CT 06820
OFF MARKET

580 Middlesex Rd
Darien, CT 06820

  • 4 Beds
  • 4 Baths
  • 3,296 sqft (on 2.52 acres)

$2,850,600

Trulia Estimate
as of May 23, 2026
Est. Refi. Payment $18,444/mo*
Refinance Your Home

$2,850,600

Trulia Estimate
as of May 23, 2026
Est. Refi. Payment $18,444/mo*
Refinance Your Home
4 Beds
4 Baths
3,296 sqft
(on 2.52 acres)

Local Information

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

Description

Welcome to Whitegate Farm! This idyllic summer rental is for July 1-August 24th (or through Sept 4th for $60K) and provides country charm with a tree lined driveway set amid a 2.5 acre oasis with heated gunite pool and spa. The pool terrace is accessible from almost every room, making this four bedroom sun drenched home perfect for entertaining both indoors and outdoors on sunny summer days. Originally a horse stable, the cottage has been renovated to provide a spacious guest or pool house with full bath. Walk across the street to Highland Farm park where you can enjoy walks in this public open space. With easy access to both town beaches, town shopping, restaurants and the train, enjoy your summer in relaxed sophistication.NOTES: Owner is open to leasing through Sept 4th for $60K. Utilities paid by owner. Owner will guarantee a full tank of propane for pool heat, and tenant is responsible to refill tank at the end of lease term. Additionally, owner has plans to renovate kitchen prior to July 1 and will also consider providing access to their vehicle.
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, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 580 Middlesex Rd

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Interior Details
Number of Rooms: 9
Appliances & Utilities
DishwasherDryerWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1952
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Exterior Features

Exterior Home Features
Patio
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 2.52 acres

Price History for 580 Middlesex Rd

DatePriceEventSource
05/01/2024ListingRemovedZillow Rentals
03/26/2024$22,500PriceChange
Zillow Rentals
03/18/2024$25,000PriceChange
Zillow Rentals
03/12/2024$27,500Listed For RentZillow Rentals
06/02/2023ListingRemovedZillow Rentals
04/18/2023$27,500Listed For RentZillow Rentals
09/17/2016$24,000ListingRemovedAgent Provided
09/25/2014$10,500ListingRemovedAgent Provided
07/10/2014$10,500PriceChange
Agent Provided
06/28/2013$9,500PriceChange
Agent Provided
05/08/2013$10,500Listed For RentAgent Provided
08/23/2004$238,200Sold
N/A
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Property Tax and Assessment

Year2025
Tax$20,929
Assessment$1,351,980
Home facts updated by county records

Comparable Sales for 580 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
23 Maplewood Drive, Darien, CT
0.63
Single-Family Home
$2,710,000
12/08/25
5
3.5
3,506
37 Salisbury Road, Darien, CT
0.63
Single-Family Home
$2,795,000
08/11/25
4
3.5
3,261
6 Pilgrim Rd, Darien, CT
0.73
Single-Family Home
$3,400,000
06/16/25
5
3.5
3,257
2 Natures Way, Darien, CT
0.75
Single-Family Home
$2,750,000
06/17/25
4
4
3,815
2 Sherry Ln, Darien, CT
0.78
Single-Family Home
$2,585,000
10/29/25
4
4.5
3,186
63 Dorchester Road, Darien, CT
0.80
Single-Family Home
$3,500,000
05/12/26
4
4.5
3,470
451 Mansfield Ave, Darien, CT
0.46
Single-Family Home
$3,380,000
04/13/26
5
6
7,652
49 Salisbury Rd, Darien, CT
0.59
Single-Family Home
$2,865,000
04/20/26
5
4.5
4,000
109 Stephen Mather Road, Darien, CT
0.85
Single-Family Home
$3,000,000
03/02/26
5
3.5
4,817
20 Shady Acres Road, Darien, CT
0.99
Single-Family Home
$2,460,000
08/20/25
5
4
3,322

Nearby homes

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Assigned Schools

These are the assigned schools for 580 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"
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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
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  • 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!"
    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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580 Middlesex Rd, Darien, CT 06820 is a 4 bedroom, 4 bathroom, 3,296 sqft single-family home built in 1952. This property is not currently available for sale. 580 Middlesex Rd was last sold on Aug 23, 2004 for $238,200. The current Trulia Estimate for 580 Middlesex Rd is $2,850,600.