305 Middlesex Rd, Darien, CT 06820
OFF MARKET

305 Middlesex Rd
Darien, CT 06820

  • 4 Beds
  • 3.5 Baths
  • 4,697 sqft (on 1.04 acres)

$3,052,300

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $19,776/mo*
Refinance Your Home

$3,052,300

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $19,776/mo*
Refinance Your Home
4 Beds
3.5 Baths
4,697 sqft
(on 1.04 acres)

Local Information

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

Description

Turn-key, close to town...Built in 2012, this contemporary colonial offers everything for today's lifestyle. The gourmet kitchen has a large island plus dining area overlooking the stone terrace. Opening from the kitchen, is the light-filled family room with wood-burning fireplace. The millwork, built-ins & gas fireplace in the formal dining/living room create a cozy space for entertaining. The master suite boasts vaulted ceilings, walk-in closet, bathroom with double vanity, separate tub & shower. In 2016, a playroom was added with high ceilings & hardwood floors. The walk-up 3rd floor with HVAC capability creates opportunity for add'l living quarters. Convenient in-town location within walking distance to high school. *Taxes are $1,191 for #309 Middlesex land, incorporated in sale.
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, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 305 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Forced Air, Other, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Number of Rooms: 10Types of Rooms: Walk In Closet, Dining Room, Family Room, Library, Master Bath, Mud Room, Recreation Room
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: WoodFoundation Type: Crawl RaisedLawnPatioSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2012
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.04 acres

Price History for 305 Middlesex Rd

DatePriceEventSource
06/15/2018$1,700,000Sold
Smart MLS #99173085
04/06/2018$1,745,000PendingAgent Provided
02/14/2018$1,745,000PriceChange
Agent Provided
10/06/2017$1,849,000PriceChange
Agent Provided
03/23/2017$1,995,000PriceChange
Agent Provided
02/03/2017$2,095,000Listed For SaleAgent Provided
11/19/2016$2,195,000ListingRemovedAgent Provided
07/12/2016$2,195,000PriceChange
Agent Provided
04/27/2016$2,245,000PriceChange
Agent Provided
03/29/2016$2,320,000PriceChange
Agent Provided
02/25/2016$2,395,000Listed For SaleAgent Provided
12/21/2012$1,910,000Sold
Smart MLS #98535927
11/27/2012$1,995,000PendingAgent Provided
10/06/2012$1,995,000PriceChange
Agent Provided
06/21/2012$2,199,000PriceChange
Agent Provided
03/28/2012$2,299,000Listed For SaleAgent Provided
01/29/2003$535,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$20,838
Assessment$1,346,100
Home facts updated by county records

Comparable Sales for 305 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
26 Holly Lane, Darien, CT
0.16
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
29 Stony Brook Road, Darien, CT
0.32
Single-Family Home
$4,200,000
07/14/25
4
4.5
5,308
25 Libby Lane, Darien, CT
0.19
Single-Family Home
$4,325,000
07/29/25
5
6
5,545
54 Stony Brook Rd, Darien, CT
0.27
Single-Family Home
$4,425,000
08/04/25
6
6
6,446
3 Revere Road, Darien, CT
0.36
Single-Family Home
$2,350,000
05/01/26
5
3
3,395
7 Lantern Lane, Darien, CT
0.80
Single-Family Home
$2,355,000
06/12/25
4
3.5
3,742
326 Hollow Tree Ridge Road, Darien, CT
0.54
Single-Family Home
$3,650,000
08/20/25
5
4.5
6,860
12 Kona Road, Darien, CT
0.34
Single-Family Home
$4,400,000
05/29/25
5
6.5
6,805
6 Priscilla Lane, Darien, CT
0.46
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
109 West Avenue, Darien, CT
0.47
Single-Family Home
$2,050,000
09/05/25
5
4.5
3,591

Nearby homes

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Assigned Schools

These are the assigned schools for 305 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"
    0
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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 "
    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
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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
    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
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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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305 Middlesex Rd, Darien, CT 06820 is a 4 bedroom, 4 bathroom, 4,697 sqft single-family home built in 2012. This property is not currently available for sale. 305 Middlesex Rd was last sold on Jun 15, 2018 for $1,700,000. The current Trulia Estimate for 305 Middlesex Rd is $3,052,300.