121 Middlesex Road, Darien, CT 06820
OFF MARKET

121 Middlesex Road
Darien, CT 06820

  • 4 Beds
  • 2.5 Baths
  • 3,074 sqft (on 0.64 acres)

$2,354,600

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $15,434/mo*
Refinance Your Home

$2,354,600

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $15,434/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,074 sqft
(on 0.64 acres)

Home Value

Trulia Estimate
$2.35M
Since last month
Increased$6K (+0.2%)
Since last year
Increased$213K (+9.9%)
Since last sale
Increased$556K (+30.9%)
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 +78% in the last 10 years
MonthEstimated value
2026
August 2026$2.36M
July 2026$2.35M
June 2026$2.37M
May 2026$2.34M
April 2026$2.33M
March 2026$2.33M
February 2026$2.23M
January 2026$2.17M
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
19 Chester Road, Darien, CT
0.22
Single-Family Home
$2,365,000
07/31/26
4
2.5
3,264
3 Hickory Lane, Darien, CT
0.17
Single-Family Home
$2,875,000
07/01/26
4
4
2,920
86 Middlesex Road, Darien, CT
0.20
Single-Family Home
$2,400,000
05/19/26
4
2.5
2,850
8 Forest Road, Darien, CT
0.28
Single-Family Home
$1,650,000
11/21/25
4
3
2,707
29 Hillcrest Avenue, Darien, CT
0.18
Single-Family Home
$3,352,000
08/19/26
5
3.5
3,621
76 Deepwood Road, Darien, CT
0.20
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
201 Middlesex Road, Darien, CT
0.45
Single-Family Home
$2,760,000
08/20/26
4
2.5
3,293
25 Devon Road, Darien, CT
0.27
Single-Family Home
$1,710,000
04/27/26
4
1.5
1,953
182 Hollow Tree Ridge Road, Darien, CT
0.46
Single-Family Home
$1,825,000
06/30/26
4
2.5
2,067

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
4 Laurel Lane, Darien, CT 06820
0.04
$2,931,300
5
4
4,058
Off Market
7 Lantern Lane, Darien, CT 06820
0.08
$2,510,200
4
3.5
3,742
Off Market
1 Hickory Lane, Darien, CT 06820
0.18
$2,684,200
4
3.5
3,094
Off Market
3 Hickory Lane, Darien, CT 06820
0.17
$2,875,000
4
4
2,920
Recently Sold
29 Hillcrest Avenue, Darien, CT 06820
0.18
$3,352,000
5
3.5
3,621
Recently Sold
76 Deepwood Road, Darien, CT 06820
0.20
$2,287,500
5
4
3,897
Recently Sold
30 Hillcrest Avenue, Darien, CT 06820
0.20
$2,283,600
4
2.5
2,338
Off Market
86 Middlesex Road, Darien, CT 06820
0.20
$2,400,000
4
2.5
2,850
Recently Sold
15 Chester Road, Darien, CT 06820
0.21
$2,971,700
4
3.5
3,204
Off Market
19 Chester Road, Darien, CT 06820
0.22
$2,365,000
4
2.5
3,264
Recently Sold
6 Chester Road, Darien, CT 06820
0.24
$2,557,000
4
2.5
4,376
Off Market

Local Information

  • Map ViewExplore the area around 121 Middlesex Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1920
Lot Size
0.64 acres
Living Area
3,074 sqft
Price/Sqft
$766

About this House

The risers of the steps leading from the road to 121 Middlesex are inscribed with “White Oak Farm,” welcoming you to one of Darien’s most treasured properties. This pre-1900s farmstead was enlarged circa 1920, and the solid concrete walls that were added make the home virtually draft-free. Charming details abound, from antique-glass windows to original longleaf pine flooring and period appropriate crown moldings. While the home has been meticulously maintained in its historic roots it has also been thoughtfully renovated & modernized for high efficiency. The renovated areas have large, top of the line low-e casement windows bringing tons of sunlight throughout house. Kitchen elements include a butterflied black walnut island made out of a single flitch of wood. A LaCanche duel fuel range w/french top & Liebherr Refrigerator. The downstairs has an easy flow from kitchen to family room with a cozy wood-burning original fireplace. Four light-filled bedrooms including an oversized master suite w/ sitting room round out the upstairs. The large yard is an award-winning gardenscape complete with a low-maintenance koi pond, whimsical red maple treehouse & a built in outdoor Lynx grill with fridge & ice maker. A geothermal heating/cooling system is in place for optimum efficiency. This is a rare opportunity to own a local treasure in a prime location, an easy walk to elementary, middle, and high schools, as well as the train and new Darien Commons shopping center. Not to be missed.
121 Middlesex Road, Darien, CT 06820 is a 4 bedroom, 3 bathroom, 3,074 sqft single-family home built in 1920. It last sold for $1,800,000 on Jul 20, 2023 (13% above the $1,595,000 asking price). It is currently off market. The Trulia Estimate is $2,354,600, with a rent estimate of $7,479/month.
Last check for updates: about 8 hours ago
Listed by Kathryn Bates, (203) 554-1143
Compass Connecticut, LLC, (203) 423-3100
Bought with: Sarah Caras, (917) 407-1447, Houlihan Lawrence, (203) 655-8238
Source: Smart MLS, MLS#170558842

Home Details for 121 Middlesex Road

Interior Features

Interior Details
Basement: PartialNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3074 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Dishwasher, Tankless Water HeaterDishwasherLaundry: Main Level
Heating & Cooling
Heating: Forced Air,GeothermalHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls
Window: Storm Window(s)

Exterior Features

Exterior Home Features
Roof: TileFoundation: StoneNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Other
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3074 Square Feet

Property Information

Year Built
Year Built: 1920
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Farm House,Mediterranean
Building
Construction Materials: StuccoNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 105533

Price & Status

Price
List Price: $1,595,000
Status Change & Dates
Off Market Date: Fri Apr 07 2023Possession Timing: Flexible

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Darien
School Information
Elementary School: HolmesHigh School: Darien

Building

Building Area
Building Area: 3074 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.64 acres

Energy

Energy Efficiency Features: Insulation, HVAC, Windows

Miscellaneous

BasementMls Number: 170558842Above Grade Unfinished Area: 3074

Price and Tax history

DateEventPrice
Jul 20, 2023
Source: Smart MLS #170558842
Sold
$1,800,000
Jul 10, 2023
Source: Smart MLS #170558842
Pending
$1,595,000
Apr 7, 2023
Source: Smart MLS #170558842
Contingent
$1,595,000
Mar 29, 2023
Source: Smart MLS #170558842
Listed For Sale
$1,595,000
Mar 24, 2021
Source: N/A
ListingRemoved

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

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Frequently asked questions about 121 Middlesex Road

  • What is 121 Middlesex Road estimated to be worth?
    Trulia's estimated value for 121 Middlesex Road in Darien, CT is $2,354,600.
  • What is the price history for 121 Middlesex Road?
    121 Middlesex Road in Darien, CT last sold for $1,800,000 in July 2023.
  • 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 121 Middlesex Road have air conditioning?
    Yes, 121 Middlesex Road in Darien, CT has air conditioning.
  • Does 121 Middlesex Road have laundry facilities?
    Yes, 121 Middlesex Road in Darien, CT has laundry facilities.

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