Home / Listings / Darien
Under Contract · For Sale
$2,995,000

5 Middlesex Road, Darien, Connecticut 06820

5 beds 5 baths 6,195 sq ft Single Family For Sale Built 1880

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.

Status
Under Contract
Type
Single Family For Sale
Price
$2,995,000
Beds
5
Baths
5
Interior
6,195 sq ft
Lot
0.69 ac
Year Built
1880
MLS #
24184412
ZIP
06820
Days on Market
27
Heat
Natural Gas · Hot Water
Cooling
Central Air, Zoned
Water
Public Water Connected
Sewer
Septic
Parking
Attached Garage, Paved, Driveway (2-car)
Laundry
Upper Level

Flood risk: check the FEMA flood map for this address.

Schools

Elementary
Holmes
Middle / Jr High
Middlesex
High School
Darien

Taxes

Property tax
$23,029 (July 2025-June 2026)
Assessed value
$1,487,640

Interior

Appliances
Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Gas Dryer, Wine Chiller
Basement
Partial, Unfinished
Attic
Unfinished, Access Via Hatch
Fireplaces
1
Total rooms
10

Building & Exterior

Style
Colonial
Roof
Asphalt Shingle
Siding
Clapboard
Exterior features
Terrace, Deck, Gutters, Garden Area, Lighting, Stone Wall, Underground Sprinkler, Patio
Foundation
Stone
New construction
No/Resale

Lot & Land

Zoning
R13
Lot
Fence - Partial, Treed, Level Lot, Professionally Landscaped

What it would cost per month

An estimate you can adjust — not a quote, and not an offer of credit. Principal and interest only, plus the taxes and HOA already on this listing. Insurance, PMI and closing costs are not included. Rate seeded at 6.5% (August 2026); change it to whatever your lender quotes.

/mo
principal & interest

What's nearby

Grocery
ShopRite0.38 mi away · 8 min walk
Also nearby
Grade A Markets0.97 mi away
Pharmacy
CVS Pharmacy1.3 mi away
Train
Glenbrook Station0.45 mi away · 9 min walkMetro-North Railroad
Bus stop
Heights Rd @ 310 Heights Rd1.03 mi away
Elementary
Holmes
Middle
Middlesex
High school
Darien
~1.1 miShopRite — 0.38 miGrade A Markets — 0.97 miCVS Pharmacy — 1.3 miGlenbrook — 0.45 miHeights Rd @ 310 Heights Rd — 1.03 mi
This homeGroceryPharmacyTrainBus

Real streets from OpenStreetMap; distances are straight-line from the property, not driving routes.

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Recent comparable sales

The 5 closest recent sales to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded sale prices from the MLS, not estimates. No automated valuation is shown, because what a home is worth depends on condition, layout and timing that a formula cannot see — call John at 203·883·3399 to read them properly against this home.

5 comparable sales — median $3,150,000, ranging $2,355,000 to $3,500,000.

Public record

From the Darien assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.

Year built1880
Living area6,195 sq ft
Total rooms10
Lot size0.57 acres
Stories2
HeatCOLONIAL
ExteriorFRAME
Assessed value$1,487,640
Town appraisal$2,125,200
Last recorded sale2022 — $2,615,000

Recorded sales

Deed transfers on file with the Darien land records, newest first. These are recordings rather than MLS sales, so they include transfers that were never listed. Nominal and $0 transfers (estate, trust and family conveyances) are excluded.

Listing courtesy of William Raveis Real Estate — Allison Santopietro · (203) 255-6841

More homes in Darien

Closest in price to this one.

← Back to all Stamford listings