105 Middlesex Rd, Darien, CT 06820
Property image
Property image
OFF MARKET

$2,640,600

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

105 Middlesex Rd, Darien, CT 06820

Est. Refi. Payment $17,397/mo*
Refinance Your Home
Currently Off Market - Sold Sep 17, 2021 for $1,705,000

Home Value

Trulia Estimate
$2.64M
Since last month
Decreased$19K (-0.7%)
Since last year
Increased$207K (+8.5%)
Since last sale
Increased$928K (+54.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +84% in the last 10 years
MonthEstimated value
2026
August 2026$2.63M
July 2026$2.65M
June 2026$2.7M
May 2026$2.66M
April 2026$2.59M
March 2026$2.63M
February 2026$2.49M
January 2026$2.45M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
29 Hillcrest Avenue, Darien, CT
0.04
Single-Family Home
$3,352,000
08/19/26
5
3.5
3,621
19 Chester Road, Darien, CT
0.15
Single-Family Home
$2,365,000
07/31/26
4
2.5
3,264
76 Deepwood Road, Darien, CT
0.16
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
3 Hickory Lane, Darien, CT
0.19
Single-Family Home
$2,875,000
07/01/26
4
4
2,920
12 Laurel Lane, Darien, CT
0.13
Single-Family Home
$2,052,000
08/26/26
3
2.5
3,151
86 Middlesex Road, Darien, CT
0.07
Single-Family Home
$2,400,000
05/19/26
4
2.5
2,850
8 Forest Road, Darien, CT
0.19
Single-Family Home
$1,650,000
11/21/25
4
3
2,707
53 Hoyt Street, Darien, CT
0.40
Single-Family Home
$1,725,000
05/14/26
3
3.5
2,180
3 Devon Road, Darien, CT
0.25
Single-Family Home
$1,950,000
10/23/25
4
3.5
2,568
34 Intervale Road, Darien, CT
0.24
Single-Family Home
$2,850,000
06/22/26
4
3.5
3,180

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
29 Hillcrest Avenue, Darien, CT 06820
0.04
$3,352,000
5
3.5
3,621
Recently Sold
30 Hillcrest Avenue, Darien, CT 06820
0.06
$2,318,300
4
2.5
2,338
Off Market
86 Middlesex Road, Darien, CT 06820
0.07
$2,400,000
4
2.5
2,850
Recently Sold
4 Laurel Lane, Darien, CT 06820
0.11
$2,943,200
5
4
4,058
Off Market
12 Laurel Lane, Darien, CT 06820
0.13
$2,052,000
3
2.5
3,151
Recently Sold
121 Middlesex Road, Darien, CT 06820
0.14
$2,336,900
4
2.5
3,074
Off Market
6 Chester Road, Darien, CT 06820
0.12
$2,589,200
4
2.5
4,376
Off Market
15 Chester Road, Darien, CT 06820
0.13
$2,968,500
4
3.5
3,204
Off Market
76 Deepwood Road, Darien, CT 06820
0.16
$2,287,500
5
4
3,897
Recently Sold
12 Chester Rd, Darien, CT 06820
0.14
$2,171,000
4
2.5
2,075
Off Market
1 Hickory Lane, Darien, CT 06820
0.17
$2,712,700
4
3.5
3,094
Off Market
25 Devon Road, Darien, CT 06820
0.15
$1,710,000
4
1.5
1,953
Recently Sold

Local Information

  • Map ViewExplore the area around 105 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1950
Lot Size
0.58 acres
Living Area
3,149 sqft
Price/Sqft
$839
Parking
Garage

About this House

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!
105 Middlesex Rd, Darien, CT 06820 is a 5 bedroom, 4 bathroom, 3,149 sqft single-family home built in 1950. It last sold for $1,705,000 on Sep 17, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,640,600, with a rent estimate of $7,265/month.

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 and Tax history

DateEventPrice
Sep 17, 2021
Source: Smart MLS #170409187
Sold
$1,705,000
Jan 11, 2014
Source: Agent Provided
ListingRemoved
$1,485,000
Sep 25, 2013
Source: Smart MLS #99032176
Sold
$1,435,000
Sep 10, 2013
Source: Agent Provided
PendingToActive
$1,485,000
Sep 5, 2013
Source: Agent Provided
Pending
$1,485,000

Market trends in Darien

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.98M
$246KMoM
Sale-to-List Price
108.9%
3.3%MoM
Price per sq ft
$800
$12MoM
Available listings
36
18MoM

Around this home

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

  • 82 % 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

Frequently asked questions about 105 Middlesex Rd

  • What is 105 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 105 Middlesex Rd in Darien, CT is $2,640,600.
  • What is the price history for 105 Middlesex Rd?
    105 Middlesex Rd in Darien, CT last sold for $1,705,000 in September 2021.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Darien?
    The median sale price in Darien is $2.98M. That is up $246K from the prior month.
  • Does 105 Middlesex Rd have air conditioning?
    Yes, 105 Middlesex Rd in Darien, CT has air conditioning.
  • Does 105 Middlesex Rd have laundry facilities?
    Yes, 105 Middlesex Rd in Darien, CT has laundry facilities.

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Off Market Homes Near 105 Middlesex Rd

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