5 Middlesex Road

Closed 8/31/26
Closed 8/31/26
Side yard showing veranda, Living room and garden room
Sold
Last Sold Price
$2,995,000
5 beds6,195 sqft$483/sqft
5 Middlesex Rd, Darien, CT 06820
Single FamilyProperty Type
0.69 acresLot Size
1880Year Built
$483/sq ftPrice per sq ft
6 carsParking Spaces

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...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.
  • Listed by: Allison Santopietro 203.216.2462 allison.santopietro@raveis.com • William Raveis Real Estate
Listing closed: 08/31/2026 12:00 AM • Source: SMARTMLS, MLS#: 24184412
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Location

Listing Courtesy of William Raveis Real Estate, Allison Santopietro

Sold By Brown Harris Stevens, Serena A Richards

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$17,142 per month

30 year fixed, 6.55% Interest

Principal and Interest

$15,223

Property Taxes

$1,919

HOA Dues

$0

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Property Information for 5 Middlesex Road

Property Details
  • Taxes: $23,029 / year
  • MLS Type: Residential
  • County: Fairfield County
  • Basement Description: Partial, Unfinished
  • Direct Waterfront: No
  • Garages Number: 2
  • Style: Colonial
  • Garage Parking Info: Attached Garage, Paved, Driveway
  • Swimming Pool: No
Building Information
  • Year Built: 1880
  • Lot Size: 0.69 AC / 30,056 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Middlesex to #5. Please use front driveway. Enter thru stone pillars
  • Elementary School: Holmes
  • High School: Darien
  • Latitude: 41.076195
  • Longitude: -73.51464
  • Middle Jr High School: Middlesex
  • State: Connecticut
Parking
  • Parking Total Spaces: 6
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $23,029
Interior and Exterior Features
Exterior Features
  • Exterior Features: Terrace, Deck, Gutters, Garden Area, Lighting, Stone Wall, Underground Sprinkler, Patio
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Gas Dryer, Wine Chiller
  • Attic Description: Unfinished, Access Via Hatch
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Audio System, Auto Garage Door Opener, Security System
  • Laundry Room Info: Upper Level
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: Balcony/Deck,Breakfast Bar,Wet Bar,Eating Space,Island,Hardwood Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 2
  • Room Entry Order: 10
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 11
  • Room Features: Wet Bar,Slate Floor
  • Room Level: Main
  • Room Type: Sun Room
Room 4
  • Room Entry Order: 12
  • Room Features: Hardwood Floor,On 3rd Floor
  • Room Level: Upper
  • Room Type: Den
Room 5
  • Listing Key: 545F8A4D22CD4186E0631A01100AF91B
  • Room Entry Order: 13
  • Room Features: Hardwood Floor,On 3rd Floor
  • Room Level: Upper
  • Room Type: Other
Room 6
  • Room Entry Order: 14
  • Room Features: Full Bath,Hardwood Floor,On 3rd Floor
  • Room Level: Upper
  • Room Type: Other
Room 7
  • Room Entry Order: 2
  • Room Features: Bay/Bow Window,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 8
  • Room Entry Order: 3
  • Room Features: Bay/Bow Window,9 ft+ Ceilings,Fireplace,Patio/Terrace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 9
  • Listing Key: 545F8A4D22CD4186E0631A01100AF91B
  • Room Entry Order: 4
  • Room Features: Built-Ins,Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Family Room
Room 10
  • Room Entry Order: 5
  • Room Features: Book Shelves,Hardwood Floor
  • Room Level: Main
  • Room Type: Library
Room 11
  • Room Entry Order: 6
  • Room Features: Balcony/Deck,Beams,Gas Log Fireplace,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 12
  • Room Entry Order: 7
  • Room Features: Beams,Full Bath,Wide Board Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 13
  • Room Entry Order: 8
  • Room Features: Bay/Bow Window,Wide Board Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 14
  • Room Entry Order: 9
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Driveway Type: Private, Paved, Crushed Stone
  • Exterior Siding: Clapboard
  • Foundation Type: Stone
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1880
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 6195
Lot Information
  • Lot Description: Fence - Partial, Treed, Level Lot, Professionally Landscaped
  • Parcel Number: 105522
  • Sq Ft Est Heated Above Grade: 6195.0
  • Sq Ft Total: 6195.0
  • Zoning: R13
Utilities
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Other
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 5 Middlesex Road

DateEvent & SourcePriceAppreciation
May 2, 2022

Closed (Public Record)

Public Record #1489525362

$2,615,000

+4.4% / yr

Nov 16, 2009

Closed (Public Record)

Public Record #279651002

$1,525,000

+17032.4% / yr

Feb 9, 2007

Closed (Public Record)

Public Record #327034812

$1—
DateEvent & SourcePrice
05/02/2022

Closed (Public Record)

Public Record #1489525362

$2,615,000

+4.4% / yr

11/16/2009

Closed (Public Record)

Public Record #279651002

$1,525,000

+17032.4% / yr

02/09/2007

Closed (Public Record)

Public Record #327034812

$1

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 5 Middlesex Road

Taxable ValueLand$663,950Additions$823,690Total$1,487,640
Tax Record2025$23,029 ($1,919 / month)
Home Facts
Beds5Baths4.5Total Finished SqFt6,195 SqFtAbove Grade Finished SqFt6,195 SqFtUnfinished Basement SqFt432 SqFtStories2Lot Size25,003 SqFtStyleSingle Family ResidenceYear Built1880Year Renovated2006ZoningR13CountyWESTERN CONNECTICUTAPNDARI M:25 B:93

Schools near 5 Middlesex Road

This home is within Darien School District.
Rating
School
Type
Grades
Distance
Holmes Elementary School
Public - PK to 5
Middlesex Middle School
Public - 6 to 8
Darien High School
Public - 9 to 12
Rating
School
Distance
Holmes Elementary School
PublicPK to 5

Middlesex Middle School
Public6 to 8

Darien High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Darien
Darien
A coastal Connecticut town with a strong sense of community. Incorporated in 1820, Darien is a popular coastal town situated between Stamford and Norwalk. Just a 1 hour train ride from Manhattan via Metro North, Darien is an ideal commuter town that boasts spectacular shoreline activities...
Darien Guide

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Raveis Real Estate, Allison Santopietro

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.