5 Middlesex Road, Darien, CT 06820
Property image
Property image
UNDER CONTRACT
0.69 ACRES

5 Middlesex Road
Darien, CT 06820

  • 5 Beds
  • 4.5 Baths
  • 6,195 sqft (on 0.69 acres)

$2,995,000

Est. Mortgage $19,611/mo*
Get Pre-Qualified

$2,995,000

Est. Mortgage $19,611/mo*
Get Pre-Qualified
5 Beds
4.5 Baths
6,195 sqft
(on 0.69 acres)

Home Highlights

Parking
2 Car Garage
Outdoor
Patio, Deck
Price/Sqft
$483
Listed
67 days ago
Climate Control
Natural Gas, Hot Water & Central Air, Zoned

Local Information

  • Map ViewExplore the area around 5 Middlesex Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Step into a truly special offering- a stately New England home, thoughtfully RENOVATED and completely MOVE-IN READY. Conveniently located close to the train, elementary school, downtown shopping/dining, and parks. Situated on over half an acre this home also enjoys access to a private Cul de sac ideal for bike rides and walks, creating a true neighborhood feel. As you enter the home, you are greeted by a two-story foyer and 6,195 sqft of character, elegance, and modern convenience. The gourmet kitchen is thoughtfully appointed with a large center island, six-burner gas range, Sub-Zero refrigeration, warming drawer, wet bar, and a convenient back staircase to the second level. Two potential primary suites provide exceptional flexibility, each offering spa-like baths and peaceful retreats. SOME RECENT UPDATES include all new central air(2023 & 2024), new boiler, water heater, natural gas conversion & new flat roof. Integrated sound runs throughout the main living areas, primary suite, and veranda. A stunning formal living room with a soaring 12-ft ceiling is among the home's most impressive features, highlighted by a beautiful bow window and opening to the veranda and sun-filled garden room with heated slate floors. This extraordinary space creates an unforgettable first impression and is even more impressive in person than photos can capture. Rich hardwood flooring, natural wood beams, intricate moldings, and three fireplaces showcase timeless craftsmanship rarely found today. Designed for both comfortable living and elegant entertaining, the home also features a formal dining room for large gatherings and an inviting family room for relaxing. The EXPANSIVE THIRD FLOOR offers exceptional flexibility, featuring additional living space that could easily accommodate TWO ADDITIONAL BEDROOMS(6 & 7), a sitting area, home office or recreation space. Configured much like an apartment it provides an ideal retreat for extended family, guests, an au pair or multi generational living. Refer to FLOOR PLANS. Beautiful outdoor spaces, along with FRONT AND REAR DRIVEWAYS for additional privacy, complete this exceptional offering.
Last check for updates: about 14 hours ago
Listing courtesy of Allison Santopietro, (203) 216-2462
William Raveis Real Estate, (203) 216-2462
Source: Smart MLS, MLS#24184412
Also Listed on Smart MLS.

Home Details for 5 Middlesex Road

Interior Features

Interior Details
Basement: Partial,UnfinishedNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Den, Dining Room, Family Room, Kitchen, Library, Living Room, Other, Sun Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 6195 Square Feet
Appliances & Utilities
Appliances: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Cooler, Water HeaterDishwasherDryerLaundry: Upper LevelMicrowaveWasher
Heating & Cooling
Heating: Hot Water,Natural GasHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Terrace, Deck, PatioFencing: PartialExterior: Rain Gutters, Garden, Lighting, Stone Wall, Underground SprinklerFoundation: StoneGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Paved,Driveway,Garage Door Opener,Private
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 6195 Square Feet

Days on Market

Days on Market: 67

Property Information

Year Built
Year Built: 1880
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 105522

Price & Status

Price
List Price: $2,995,000Price Per Sqft: $483
Status Change & Dates
Off Market Date: Tue Jul 14 2026Possession Timing: Negotiable

Active Status

MLS Status: Under Contract

Location

Direction & Address
City: Darien
School Information
Elementary School: HolmesJr High / Middle School: MiddlesexHigh School: Darien

Agent Information

Listing Agent
Listing ID: 24184412

Building

Building Area
Building Area: 6195 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.69 acres

Miscellaneous

BasementMls Number: 24184412Zillow Contingency Status: Under ContractAttic: Access Via HatchAttribution Contact: (203) 216-2462Above Grade Unfinished Area: 6195

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

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

Home Value

Trulia Estimate
$3.08M
Since last month
Decreased$3K (-0.1%)
Since last year
Decreased$346K (-10.5%)
Since last sale
Increased$344K (+13.1%)
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 +39% in the last 10 years
MonthEstimated value
2026
August 2026$2.96M
July 2026$2.96M
May 2026$3.15M
April 2026$3.28M
March 2026$3.58M
February 2026$3.39M
January 2026$3.36M
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 Georgian Lane, Darien, CT
0.49
Single-Family Home
$3,250,000
03/02/26
6
5.5
6,407
30 Lake Drive, Darien, CT
0.32
Single-Family Home
$2,700,000
01/14/26
6
3.5
4,000
29 Hillcrest Avenue, Darien, CT
0.48
Single-Family Home
$3,352,000
08/19/26
5
3.5
3,621
76 Deepwood Road, Darien, CT
0.59
Single-Family Home
$2,287,500
02/27/26
5
4
3,897
34 Intervale Road, Darien, CT
0.31
Single-Family Home
$2,850,000
06/22/26
4
3.5
3,180
19 Chester Road, Darien, CT
0.44
Single-Family Home
$2,365,000
07/31/26
4
2.5
3,264
35 Hazel Street, Darien, CT
0.53
Single-Family Home
$3,150,000
06/16/26
5
5.5
4,515
20 Denhurst Place, Darien, CT
0.12
Single-Family Home
$1,580,000
11/17/25
4
2.5
2,120
3 Abbey Road, Darien, CT
0.18
Single-Family Home
$2,258,000
06/01/26
4
2.5
2,450

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
2 Red Barn Road, Darien, CT 06820
0.03
$2,526,900
4
2.5
3,358
Off Market
9 Fresh Meadows Lane, Darien, CT 06820
0.10
$2,909,200
4
3.5
3,884
Off Market
668 Glenbrook Rd #17, Stamford, CT 06907
0.13
$682,600
3
3.5
1,660
Off Market
668 Glenbrook Road #9, Stamford, CT 06906
0.13
$703,000
2
2.5
2,184
Off Market
668 Glenbrook Road #17, Stamford, CT 06906
0.13
$699,000
3
3.5
2,051
For Sale
668 Glenbrook Road #22, Stamford, CT 06906
0.13
$608,300
2
2.5
1,896
Off Market
668 Glenbrook Road #25, Stamford, CT 06906
0.13
$578,300
2
1.5
1,114
Off Market
668 Glenbrook Road #28, Stamford, CT 06906
0.13
$665,900
3
2.5
2,184
Off Market
21 Middlesex Road, Darien, CT 06820
0.09
$2,134,500
4
3.5
2,994
Off Market
154 Holmes Avenue, Darien, CT 06820
0.10
$2,299,200
5
3.5
3,108
Off Market
20 Denhurst Place, Darien, CT 06820
0.12
$1,580,000
4
2.5
2,120
Recently Sold
12 Abbey Road, Darien, CT 06820
0.11
$2,377,400
4
3.5
2,790
Off Market

Price and Tax history

DateEventPrice
Jul 14, 2026
Source: Smart MLS #24184412
Pending
$2,995,000
Jun 17, 2026
Source: Smart MLS #24184412
Listed For Sale
$2,995,000
Jun 16, 2026
Source: Smart MLS #24157558
ListingRemoved
$3,245,000
May 12, 2026
Source: Smart MLS #24157558
PriceChange
$3,245,000
Price decreased by 3%
Apr 22, 2026
Source: Smart MLS #24157558
PriceChange
$3,345,000
Price decreased by 4%

LGBTQ Local Legal Protections

Allison Santopietro, William Raveis Real Estate, (203) 216-2462
Agent Phone: (203) 216-2462
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.

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Frequently asked questions about 5 Middlesex Road

  • What is the estimated monthly payment for 5 Middlesex Road?
    Based on a $2,995,000 list price with 20% down at today's rates, the estimated monthly payment for 5 Middlesex Road in Darien, CT is approximately $19,951 (about $15,658 principal & interest, $4,218 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 5 Middlesex Road compare to homes in Darien?
    5 Middlesex Road in Darien, CT is listed at $2,995,000, about 1% above the $2.98M median sale price in Darien.
  • What do residents say about Darien?
    Residents describe Darien, CT as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See homes for sale in Darien, CT.
  • What are the closest schools to 5 Middlesex Road?
    The closest schools to 5 Middlesex Road in Darien, CT are Darien High School (rated 10/10), Holmes Elementary School (Pre-K, rated 9/10), Middlesex Middle School (rated 10/10).
  • Does 5 Middlesex Road have air conditioning?
    Yes, 5 Middlesex Road in Darien, CT has air conditioning.
  • Does 5 Middlesex Road have laundry facilities?
    Yes, 5 Middlesex Road in Darien, CT has in-unit laundry.
5 Middlesex Road, Darien, CT 06820 is a 5 bedroom, 5 bathroom, 6,195 sqft single-family home built in 1880. This property is currently available for sale and was listed by Smart MLS on Jun 17, 2026. The MLS # for this home is MLS# 24184412.