Is Darien, CT dog-friendly?

As of early 2026, 92% of users say it's dog friendly

Are yards well-kept in Darien, CT?

As of early 2026, 89% of users say yards are well-kept

Is parking easy in Darien, CT?

As of early 2026, 88% of users say parking is easy

Is a car needed in Darien, CT?

As of early 2026, 87% of users say car is needed

Does Darien, CT show holiday spirit?

As of early 2026, 84% of users say there's holiday spirit

Would people walk alone at night in Darien, CT?

As of early 2026, 81% of users say people would walk alone at night

Do kids play outside in Darien, CT?

As of early 2026, 80% of users say kids play outside

Is there wildlife in Darien, CT?

As of early 2026, 73% of users say there's wildlife

As of early 2026, 71% of users say it's quiet

Do residents of Darien, CT plan to stay at least 5 years?

As of early 2026, 70% of users say they plan to stay for at least 5 years

Are neighbors friendly in Darien, CT?

As of early 2026, 58% of users say neighbors are friendly

Are there community events in Darien, CT?

As of early 2026, 58% of users say there are community events

Does Darien, CT have sidewalks?

As of early 2026, 58% of users say there are sidewalks

Is Darien, CT walkable to restaurants?

As of early 2026, 55% of users say it's walkable to restaurants

Is Darien, CT walkable to grocery stores?

As of early 2026, 48% of users say it's walkable to grocery stores

Are the streets well-lit in Darien, CT?

As of early 2026, 44% of users say streets are well-lit

FOR SALE

0.69 ACRES

5 Middlesex Road
Darien, CT 06820

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

$3,345,000

$3,495,000

Est. Mortgage $21,350/mo*

Get Pre-Qualified

$3,345,000

$3,495,000

Est. Mortgage $21,350/mo*

Get Pre-Qualified

5 Beds

4.5 Baths

6,195 sqft

(on 0.69 acres)

Local Information

-- mins to

Commute Destination

Description

Step into a truly special offering- a stately New England home, thoughtfully RENOVATED and completely MOVE-IN READY. Conveniently located close to train, elementary school, downtown shopping/dining, and parks. South-facing and situated on over half an acre, this gracious residence offers 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. Recent updates include central air, a new boiler, natural gas conversion and a 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. Multiple outdoor spaces, along with FRONT AND REAR DRIVEWAYS for additional privacy, complete this exceptional offering.

Home Highlights

Parking

2 Car Garage

Outdoor

Patio, Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

$540

Listed

39 days ago

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: Forced Air,Zoned,Natural GasHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Forced Air
Fireplace & Spa Number of Fireplaces: 3Has 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: 39

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: $3,345,000Price Per Sqft: $540
Status Change & Dates Possession Timing: Negotiable

Active Status
MLS Status: Active

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

Agent Information
Listing Agent Listing ID: 24157558

Building
Building Area Building Area: 6195 Square Feet

HOA
No HOA

Lot Information
Lot Area: 0.69 acres

Miscellaneous
BasementMls Number: 24157558Attic: Access Via HatchAttribution Contact: (203) 216-2462Above Grade Unfinished Area: 6195Activation Date: Thu Apr 02 2026

Last check for updates: about 8 hours ago

Listing courtesy of Allison Santopietro, (203) 216-2462

William Raveis Real Estate, (203) 216-2462

Source: Smart MLS, MLS#24157558

Also Listed on Smart MLS.

Price History for 5 Middlesex Road

Date	Price	Event	Source
04/22/2026	$3,345,000	PriceChange	Smart MLS #24157558
Price Change $150,000 (-4%)
04/02/2026	$3,495,000	Listed For Sale	Smart MLS #24157558

05/02/2022	$2,615,000	Sold	Smart MLS #170468463
Recording Date 05/02/2022 County Transfer Tax N/A Total Transfer Tax N/A
03/05/2022	$2,490,000	Contingent	Smart MLS #170468463

02/24/2022	$2,490,000	Listed For Sale	Smart MLS #170468463

11/16/2009	$1,525,000	Sold	N/A
Recording Date 11/16/2009 County Transfer Tax N/A Total Transfer Tax N/A
05/27/2004	$1,501,000	Sold	Smart MLS #98192386
Recording Date 05/27/2004 County Transfer Tax N/A Total Transfer Tax N/A
12/16/1998	$775,000	Sold	N/A
Recording Date 12/16/1998 County Transfer Tax N/A Total Transfer Tax N/A
02/21/1996	$465,000	Sold	N/A
Recording Date 02/21/1996 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$23,029
Assessment	$1,487,640

Home facts updated by county records

Comparable Sales for 5 Middlesex Road

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
154 Holmes Avenue, Darien, CT	0.10	Single-Family Home	$2,160,000	07/30/25	5	3.5	3,108
19 Georgian Lane, Darien, CT	0.49	Single-Family Home	$3,250,000	03/02/26	6	5.5	6,407
12 Abbey Road, Darien, CT	0.11	Single-Family Home	$2,235,000	08/18/25	4	3.5	2,790
147 Holmes Avenue, Darien, CT	0.17	Single-Family Home	$1,850,000	07/21/25	5	3.5	2,974
11 Christie Hill Road, Darien, CT	0.22	Single-Family Home	$1,951,000	07/10/25	4	3	2,852
30 Lake Drive, Darien, CT	0.32	Single-Family Home	$2,700,000	01/14/26	6	3.5	4,000
4 Echo Drive, Darien, CT	0.45	Single-Family Home	$3,500,000	08/06/25	5	5	5,348
76 Deepwood Road, Darien, CT	0.59	Single-Family Home	$2,287,500	02/27/26	5	4	3,897

Assigned Schools

These are the assigned schools for 5 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

Learn more about our methodology.

Kimrichardnyc
Resident
1y ago
"Happy, safe and friendly place to live and raise children. Need more diversification like in wesport CT though. "
0
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Trulia User
Resident
1y ago
"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
Resident
2y ago
"great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
0
Flag
Jessica_hatch7
Resident
6y ago
"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.
Resident
6y ago
"Holidays and school events. Dining and activities such as sports, the arts and many many social events"
0
Flag
Mzengo8
Resident
7y ago
"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.
Prev. Resident
7y ago
"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
Resident
7y ago
"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.
Resident
7y ago
"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.
Resident
7y ago
"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
Resident
7y ago
"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
Resident
7y ago
"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
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Kathrynquirk445
Resident
8y ago
"Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
0
Flag
Bill T.
Prev. Resident
8y ago
"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
11y ago
"Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
0
Flag

LGBTQ Local Legal Protections

Additional Cost

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.

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 Mar 30, 2026. The MLS # for this home is MLS# 24157558.

5 Middlesex Road
Darien, CT 06820

$3,345,000

$3,345,000

Local Information