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)

$2,313,400

Trulia Estimate
as of May 23, 2026
Est. Refi. Payment $14,982/mo*
Refinance Your Home

$2,313,400

Trulia Estimate
as of May 23, 2026
Est. Refi. Payment $14,982/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,074 sqft
(on 0.64 acres)

Local Information

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

Description

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.
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. This description is from July 21, 2023

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

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
Last check for updates: about 4 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

Price History for 121 Middlesex Road

DatePriceEventSource
07/20/2023$1,800,000Sold
Smart MLS #170558842
07/10/2023$1,595,000PendingSmart MLS #170558842
04/07/2023$1,595,000ContingentSmart MLS #170558842
03/29/2023$1,595,000Listed For SaleSmart MLS #170558842
03/24/2021ListingRemovedN/A
08/10/2009$1,185,000ListingRemovedN/A
03/09/2009$1,185,000Listed For SaleN/A
06/10/2005$1,185,000Sold
Smart MLS #98223524
09/16/1997$580,000Sold
N/A
09/30/1996$607,500Sold
N/A
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$16,461
Assessment$1,063,370
Home facts updated by county records

Comparable Sales for 121 Middlesex Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
108 Colony Road, Darien, CT
0.26
Single-Family Home
$1,850,000
06/20/25
4
2.5
2,869
7 Lantern Lane, Darien, CT
0.08
Single-Family Home
$2,355,000
06/12/25
4
3.5
3,742
86 Middlesex Road, Darien, CT
0.20
Single-Family Home
$2,400,000
05/19/26
4
2.5
2,850
11 Christie Hill Road, Darien, CT
0.46
Single-Family Home
$1,951,000
07/10/25
4
3
2,852
8 Forest Road, Darien, CT
0.28
Single-Family Home
$1,650,000
11/21/25
4
3
2,707
76 Deepwood Road, Darien, CT
0.20
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
6 Chester Road, Darien, CT
0.24
Single-Family Home
$2,400,000
06/26/25
4
2.5
4,376
25 Devon Road, Darien, CT
0.27
Single-Family Home
$1,710,000
04/27/26
4
1.5
1,953
39 Deepwood Road, Darien, CT
0.22
Single-Family Home
$4,022,500
08/01/25
5
3.5
4,932

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 121 Middlesex Road.
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 121 Middlesex Road

Skip to last item
Skip to first item

Off Market Homes Near 121 Middlesex Road

Skip to last item
Skip to first item
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Homes for rent near 121 Middlesex Road

Skip to last item
  • Results are loading
Skip to first item
121 Middlesex Road, Darien, CT 06820 is a 4 bedroom, 3 bathroom, 3,074 sqft single-family home built in 1920. This property is not currently available for sale. 121 Middlesex Road was last sold on Jul 20, 2023 for $1,800,000 (13% higher than the asking price of $1,595,000). The current Trulia Estimate for 121 Middlesex Road is $2,313,400.