5 Middlesex Road

Darien CT 06820

6195 sq. ft.

0.69 ac.

Single-Family

Last sold for $2,995,000

Allison Santopietro, last sold this property on 31 August 2026 after 151 days on market.

Overview

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.

Features

5 bedrooms

5 bathrooms

6 carspaces

2 garage spaces

6195 sq. ft. floor area

0.69 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Darien over the last 12 months, the estimated median property value of 5 Middlesex Road is $3.6m.

Median value

$3.6m

Estimated value range

$1.05m - $13m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Darien. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 5 Middlesex Road

2026

Sold

$2,995,000

31 Aug 2026 by Allison Santopietro, of William Raveis Real Estate

2022

Sold

$2,615,000

02 May 2022 by Chichi Mayhew, of Compass Connecticut, LLC

Happy sellers in Darien

We have insufficient information to provide an overview of customer satisfaction for Darien. Viewing the agent profiles, reviews and sales for Darien can provide insights for this location.