5 Middlesex Rd

Darien, CT 06820

$3,495,000
Price
5
Beds
6,195 Sq. Ft.
$564 / Sq. Ft.
6,195
Sq. Ft.
$564
per Sq. Ft.
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a front view of a house with a garden and yard
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Description

Step into a rare offering that captures the essence of classic New England living-a stately 1880s residence set in one of the Gold Coast's most desirable towns. South-facing and beautifully sited on over half an acre, this gracious home offers more than 6,100 sqft of character, elegance, and modern comfort. A stunning formal living room with a soaring 12-foot ceiling is among the home's most impressive features, highlighted by a beautiful bow window and opening to the veranda and sun-filled garden...Step into a rare offering that captures the essence of classic New England living-a stately 1880s residence set in one of the Gold Coast's most desirable towns. South-facing and beautifully sited on over half an acre, this gracious home offers more than 6,100 sqft of character, elegance, and modern comfort. A stunning formal living room with a soaring 12-foot 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 and an inviting family room. 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. Updates include central air, a newer boiler, natural gas conversion, and integrated sound throughout the main living areas, primary suite, and veranda. Multiple outdoor spaces, along with FRONT AND REAR DRIVEWAYS, complete this exceptional offering.
  1. Listed by Allison Santopietro • William Raveis Real Estate
    P: (203)-216-2462 C: (203)-216-2462 allison.santopietro@raveis.com

Property Details for 5 Middlesex Road

Basement Description
Partial, Unfinished
Direct Waterfront
No
Expected Active Date
04-02-2026
Garages Number
2
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Attached Garage, Paved, Driveway
Swimming Pool
No
LISTING UPDATED: 04/05/2026 12:40 AM

Property Details for 5 Middlesex Road

StatusActive
MLS #24157558
Days on Market4
Taxes$23,029 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1880
Lot Size0.69 AC / 30,056 SF
CountyFairfield County
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Location

Listing Courtesy of William Raveis Real Estate, Allison Santopietro
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Building Information for 5 Middlesex Road

Stories-Year Built1880Building Size-Lot Size0.69 AC / 30,056 SF

Payment Calculator

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$19,518 per month

30 year fixed, 6.46% Interest

Principal and Interest

$17,599

Property Taxes

$1,919

HOA Dues

$0

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Property Information for 5 Middlesex Road

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: 41.076193
  • Longitude: -73.514642
  • 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 Air, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 3
  • 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: 4C38F3970FA276E9E063E201100A3253
  • 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: 4C38F3970FA276E9E063E201100A3253
  • 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

+17032.5% / yr

Feb 9, 2007

Closed (Public Record)

Public Record #327034812

$1—
Feb 9, 2007

Closed (Public Record)

Public Record #327034811

$1

-99.5% / yr

May 27, 2004

Closed (Public Record)

Public Record #137657832

$1,501,000—
May 27, 2004

Closed (Public Record)

Public Record #137657832

$1,501,000

+12.9% / yr

Dec 16, 1998

Closed (Public Record)

Public Record #90943079

$775,000

+19.9% / yr

Feb 21, 1996

Closed (Public Record)

Public Record #90943644

$465,000—
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

+17032.5% / yr

02/09/2007

Closed (Public Record)

Public Record #327034812

$1
02/09/2007

Closed (Public Record)

Public Record #327034811

$1

-99.5% / yr

05/27/2004

Closed (Public Record)

Public Record #137657832

$1,501,000
05/27/2004

Closed (Public Record)

Public Record #137657832

$1,501,000

+12.9% / yr

12/16/1998

Closed (Public Record)

Public Record #90943079

$775,000

+19.9% / yr

02/21/1996

Closed (Public Record)

Public Record #90943644

$465,000

For completeness, Compass 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 Record2024$23,029 ($1,919 / month)
Home Facts
Beds5Baths4.5Total Finished SqFt6,195 SqFtAbove Grade Finished SqFt6,195 SqFtStories2Lot Size25,003 SqFtStyleSingle Family ResidenceYear Built1880Year Renovated2006ZoningR13CountyFAIRFIELDAPNDARI M:25 B:93Fireplace TypeHas Fireplace

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.

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More information about 5 Middlesex Road, Darien, CT 06820

5 Middlesex Road is a single family home for sale in Darien, CT 06820. This property was listed for sale on March 30, 2026 by William Raveis Real Estate, it's currently listed at $3,495,000. It has been on the market for a total of 4 days and was last sold on May 2, 2022. This listing's school district is Darien School District. Nearby schools include Holmes Elementary School, Middlesex Middle School and Darien High School. 5 Middlesex Road is a 5-bed, 5-bath, 6,195 sqft single family home built in 1880.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. 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.