105 Middlesex Rd, Darien, CT 06820
OFF MARKET

105 Middlesex Rd
Darien, CT 06820

  • 5 Beds
  • 4 Baths
  • 3,149 sqft (on 0.58 acres)

$2,661,600

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $17,086/mo*
Refinance Your Home

$2,661,600

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $17,086/mo*
Refinance Your Home
5 Beds
4 Baths
3,149 sqft
(on 0.58 acres)

Local Information

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

Description

Charming expanded Cape Cod with gracious formal and informal living spaces was fully renovated in 2002 by prior owner. Ideal nanny, teenager or parent bedroom in separate section of the house. Renovated kitchen with eating area, updated baths, lower level playroom, den that could double as another bedroom, screened porch, fenced portion of the yard and charming details make this house a winner. The view across the street is beautiful Woodland Park. Getting to the train, highways, shopping, schools and the beach are a snap!
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
Porch, Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 105 Middlesex Rd

Interior Features

Interior Details
BasementAtticTypes of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood, Slate
Fireplace & Spa
FireplaceJetted Bath Tub
Security
Security System

Property Information

Year Built
Year Built: 1950Year Updated: 2015
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Exterior Features

Exterior Home Features
Exterior: WoodLawnPatioPorchSprinkler System
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.58 acres

Price History for 105 Middlesex Rd

DatePriceEventSource
09/17/2021$1,705,000Sold
Smart MLS #170409187
01/11/2014$1,485,000ListingRemovedAgent Provided
09/25/2013$1,435,000Sold
Smart MLS #99032176
09/10/2013$1,485,000PendingToActiveAgent Provided
09/05/2013$1,485,000PendingAgent Provided
08/11/2013$1,485,000PendingToActiveAgent Provided
08/06/2013$1,485,000PendingAgent Provided
07/27/2013$1,485,000PendingToActiveAgent Provided
07/26/2013$1,485,000PendingAgent Provided
06/19/2013$1,485,000Listed For SaleAgent Provided
08/08/2002$1,228,500Sold
Smart MLS #98131683
12/19/1997$341,250Sold
N/A
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$17,639
Assessment$1,139,460
Home facts updated by county records

Comparable Sales for 105 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
76 Deepwood Road, Darien, CT
0.16
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
86 Middlesex Road, Darien, CT
0.07
Single-Family Home
$2,400,000
05/19/26
4
2.5
2,850
108 Colony Road, Darien, CT
0.37
Single-Family Home
$1,850,000
06/20/25
4
2.5
2,869
11 Christie Hill Road, Darien, CT
0.32
Single-Family Home
$1,951,000
07/10/25
4
3
2,852
8 Forest Road, Darien, CT
0.19
Single-Family Home
$1,650,000
11/21/25
4
3
2,707
7 Lantern Lane, Darien, CT
0.22
Single-Family Home
$2,355,000
06/12/25
4
3.5
3,742
147 Holmes Avenue, Darien, CT
0.41
Single-Family Home
$1,850,000
07/21/25
5
3.5
2,974
154 Holmes Avenue, Darien, CT
0.44
Single-Family Home
$2,160,000
07/30/25
5
3.5
3,108
10 Hillcrest Ave, Darien, CT
0.18
Single-Family Home
$2,925,000
07/01/25
5
3.5
3,750
53 Hoyt Street, Darien, CT
0.40
Single-Family Home
$1,725,000
05/14/26
3
3.5
2,180

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 105 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
    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

Homes for sale near 105 Middlesex Rd

Skip to last item
Skip to first item

Off Market Homes Near 105 Middlesex Rd

Skip to last item
Skip to first item

Homes for rent near 105 Middlesex Rd

Skip to last item
Skip to first item
105 Middlesex Rd, Darien, CT 06820 is a 5 bedroom, 4 bathroom, 3,149 sqft single-family home built in 1950. This property is not currently available for sale. 105 Middlesex Rd was last sold on Sep 17, 2021 for $1,705,000. The current Trulia Estimate for 105 Middlesex Rd is $2,661,600.