5 Middlesex Road
Darien, Connecticut 06820
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 6,195
- Acres
- 0.69
- Year Built
- 1880
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
25
54 under contract
Median List Price
$3.80M
25 active listings
Median Closed Price
$2.71M
211 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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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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.