5 Middlesex Road, Darien, CT 06820 - Photo 1

1/1

$2,995,000

Sold
Closed
Single Family
5 Beds
4 Full Baths
1 Partial Bath
6,195 Sq. Ft.
2 Car Garage

1/1

Property Description

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.

Full Property Details

Full Property Details for 5 Middlesex Rd

General

Sold For: $2,995,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24184412
Added to Site: 117 day(s) ago

Interior

Number of Rooms: 10
Interior Features: Audio System, Auto Garage Door Opener, Security System
Fireplace: Yes
Number of Fireplaces: 1
Appliances: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Gas Dryer, Wine Chiller

Rooms

Bathrooms

Total Bathrooms: 5
Full Bathrooms: 4
Half Bathrooms: 1

Bedrooms

Total Bedrooms: 5
Primary Bedroom: Primary Bedroom - Balcony/Deck, Beams, Gas Log Fireplace, Full Bath, Walk-In Closet, Hardwood Floor, Upper
Bedroom 1: Bedroom - Beams, Full Bath, Wide Board Floor, Upper
Bedroom 2: Bedroom - Hardwood Floor, Upper
Bedroom 3: Bedroom - Bay/Bow Window, Wide Board Floor, Upper
Bedroom 4: Bedroom - Hardwood Floor, Upper

Other Rooms

Living Room: Living Room - Bay/Bow Window, 9 ft+ Ceilings, Fireplace, Patio/Terrace, Hardwood Floor, Main
Family Room: Family Room - Built-Ins, Fireplace, Hardwood Floor, Main
Eat In Kitchen: Eat-In Kitchen - Balcony/Deck, Breakfast Bar, Wet Bar, Eating Space, Island, Har, Main
Dining Room: Dining Room - Bay/Bow Window, Hardwood Floor, Main
Den: Den - Hardwood Floor, On 3rd Floor, Upper
Library: Library - Book Shelves, Hardwood Floor, Main
Laundry: Upper Level
Other Room 1: Other - Hardwood Floor, On 3rd Floor, Upper
Other Room 2: Other - Full Bath, Hardwood Floor, On 3rd Floor, Upper

Exterior

Exterior Features: Terrace, Deck, Gutters, Garden Area, Lighting, Stone Wall, Underground Sprinkler, Patio
Color: White

Parking

Garage: Yes
Attached garage: Yes
Garage Spaces: 2
Total Spaces: 6
Parking: Attached Garage, Paved, Driveway

Location

County: Fairfield
Driving Directions: Middlesex to #5. Please use front driveway. Enter thru stone pillars

School Information

Elementary School: Holmes
Middle School: Middlesex
High School: Darien

Heating & Cooling

Cooling Type: Central Air, Zoned
Heating Type: Hot Water, Natural Gas
Heating Fuel: Natural Gas
Water Heater: Other

Utilities

Sewer: Septic
Water: Public Water Connected

Structural Information

Architectural Style: Colonial
Construction Status: No/Resale
Exterior Const.: Clapboard
Basement Desc.: Partial, Unfinished
Roof: Asphalt Shingle
Attic: Yes
Square Feet: 6,195
Above Ground: 6,195 Sq. Ft.
Year Built: 1880

Lot Features

Lot Size (Acres): 0.69
Driveway/Sidewalk: Private, Paved, Crushed Stone
Zoning: R13
Lot Description: Fence - Partial, Treed, Level Lot, Professionally Landscaped

Financial Considerations

Assessment Amount: $1,487,640
Tax Year: July 2025-June 2026

Disclosures and Reports

Property ID: 105522

Listed by William Raveis Real Estate, Team AFA at William Raveis Real Estate, Allison Santopietro
Sold by Brown Harris Stevens, Serena Richards

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Listing agent

— 5 Middlesex Rd —

Allison Santopietro

William Raveis Real Estate

Agent Contact: (203) 216-2462 Office Contact: (203) 255-6841

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Schools

Schools serving 5 Middlesex Rd

School District:Darien School District

Name	Grades	Distance
Holmes Elementary School, Darien, CT 18 Hoyt Street, Darien, CT 06820	K-5	0.2 mi
Middlesex Middle School 204 Hollow Tree Ridge Road, Darien, CT 06820	6-8	0.9 mi
Darien High School 80 High School Lane, Darien, CT 06820	9-12	1.4 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5 Middlesex Rd

Date

Details

Price

Change

Source

8/31/2026

Sold

$2,995,000

—

MLS

6/17/2026

Listed

$2,995,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Updated 2 days ago

3
Beds
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Total Baths
1,888
Sq. Ft.

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Active
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4
Beds
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Total Baths
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Sq. Ft.

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2
Beds
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Total Baths
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Sq. Ft.

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Just Listed

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Single Family
Active
Updated 2 days ago

2
Beds
2
Total Baths
2,265
Sq. Ft.

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Condo
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Updated 2 days ago

3
Beds
2
Total Baths
1,317
Sq. Ft.

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Price Reduced

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1
Total Bath
429
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Active
Updated 2 days ago

3
Beds
3
Total Baths
1,646
Sq. Ft.

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Price Reduced

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$275,000

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Condo
Active
Updated 6 days ago

1
Bed
1
Total Bath
739
Sq. Ft.

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Sold

$2,850,000

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Single Family
Closed

4
Beds
4
Total Baths
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Sq. Ft.

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Single Family
Closed

5
Beds
4
Total Baths
3,621
Sq. Ft.

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Sold

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Single Family
Closed

5
Beds
6
Total Baths
4,515
Sq. Ft.

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Sold

$2,875,000

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Single Family
Closed

4
Beds
4
Total Baths
2,920
Sq. Ft.

Listed by Compass Connecticut, LLC
Sold by Compass Connecticut, LLC

5 Middlesex Road, Darien, CT 06820 (MLS# 24184412) is a Single Family property that was sold at $2,995,000 on August 31, 2026. Want to learn more about 5 Middlesex Road? Do you have questions about finding other Single Family real estate for sale in Darien? You can browse all Darien real estate or contact a Coldwell Banker agent to request more information.

5 Middlesex Rd Darien, CT 06820