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5 Middlesex Road

Darien, Connecticut 06820

PENDING$2,995,000
Beds
5
Baths
4 | 1
SqFt
6,195
Acres
0.69
Year Built
1880
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

About This Home

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.

Key Facts

City/Town
Darien
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1880
Days on Market
40 days
Beds
5
Baths
4 full · 1 half
Living Area
6,195 sq ft
Lot Size
0.69 acres
Garage / Parking
2 garage · 6 total
Property Taxes
$23,029 / Annually

Market Snapshot

The Darien Market

Single Family · trailing 12 months

Median Days on Market

51

25 active listings

Median $ / Sq Ft

$733

25 active listings

Sale-to-List Ratio

106.3%

211 sales

How this home compares

List Price

$3.00M

vs $3.80M median

21.2% below median

Price / Sq Ft

$483

vs $733 median

34.1% below median

Days on Market

40 days

vs 51 days median

11 days fresher than median

Based on 25 active and 211 closed sales (trailing 12 mo) of single family in Darien. Source: SmartMLS · As of July 27, 2026.

Location

5 Middlesex Road, Darien, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$18,188

per month

  • Principal & Interest$15,271
  • Property Taxes$1,919
  • Insurance$998
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Darien
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1880
New Construction
No/Resale
Living Area
6,195 sq ft

Schools

Elementary
Holmes
High
Darien

Interior

Heating
Hot Water
Heat Fuel
Natural Gas
Cooling
Central AirZoned
Fireplaces
1
Laundry
Upper Level
Appliances
Gas RangeMicrowaveRange HoodSubzeroDishwasherWasherGas DryerWine Chiller
Basement
PartialUnfinished
Interior Features
Audio SystemAuto Garage Door OpenerSecurity System

Exterior & Lot

Lot Size
0.69 acres
Zoning
R13
Garage / Parking
2 garage spaces6 total parking spacesAttached GaragePavedDrivewayPrivatePavedCrushed Stone
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
Clapboard
Color
White
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
TerraceDeckGuttersGarden AreaLightingStone WallUnderground SprinklerPatio
Lot Description
Fence - PartialTreedLevel LotProfessionally Landscaped

Listing & Financials

Property Taxes
$23,029 / Annually
Days on Market
40
MLS #
24184412
MLS Status
Under Contract

Similar Properties

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Listed By

Allison Santopietro

(203) 216-2462

William Raveis Real Estate

(203) 255-6841

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/27/2026 at 7:05 PM UTC.