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561 Middlesex Road

Darien, Connecticut 06820

PENDING$2,999,000
Beds
4
Baths
3 | 1
SqFt
3,411
Acres
2.64
Year Built
1856
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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4 Fireplaces

About This Home

Come see this freshly transformed home on a gorgeous, flat 2.64 acre lot in the heart of Darien. Rooted in history and alive w/possibility, this freshly renewed and effortlessly inviting, 3,411 sf residence welcomes w/antique wide plank floors whispering the past, while a bright, open flow draws you into the present. The formal dining room sets the stage for memorable evenings, while an expansive great room rises w/vaulted ceilings, anchored by a wood burning hearth as sunlight spills through French doors onto a stone patio, uniting the quiet beauty of the outdoors. Nearby, a charming parlor/home office with its own fireplace drifts into a cozy den w/bath, offering space to work or unwind. At the heart of the home, the kitchen shines. New quartz counters and crisp white cabinetry frame a generous butcher block island where meals begin and conversations linger. Here, life unfolds naturally w/gatherings beside a dual-sided fireplace, sharing laughter, stories and simple moments. The adjacent playroom w/half bath completes this ideal setting. Upstairs, 4 bedrooms, 2 full baths, and a thoughtfully placed laundry area create ease for everyday living. Yet it's beyond the walls where this property truly captures the imagination. Step outside to a sweeping, level lawn where possibilities stretch as far as the eye can see. Host a soccer match, cultivate a garden, or wander along your own wooded path. This is more than a home. It's a place to grow, gather and dream bigger with time.

Key Facts

City/Town
Darien
Neighborhood
N/A
Property / Style
Single Family · Antique,Farm House
Year Built
1856
Days on Market
263 days
Beds
4
Baths
3 full · 1 half
Living Area
3,411 sq ft
Lot Size
2.64 acres
Garage / Parking
6 total
Property Taxes
$16,958 / 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

21.1% below median

Price / Sq Ft

$879

vs $733 median

19.9% above median

Days on Market

263 days

vs 51 days median

212 days longer 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

561 Middlesex Road, Darien, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$17,704

per month

  • Principal & Interest$15,291
  • Property Taxes$1,413
  • Insurance$1,000
  • 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
Antique,Farm House
Year Built
1856
New Construction
No/Resale
Living Area
3,411 sq ft

Schools

Elementary
Ox Ridge
High
Darien

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
None
Fireplaces
4
Laundry
Upper Level
Laundry Location
2nd floor
Appliances
Oven/RangeRefrigeratorWasherDryer
Basement
PartialPartial With Hatchway
In-Law Apartment
No

Exterior & Lot

Lot Size
2.64 acres
Zoning
R2
Garage / Parking
6 total parking spacesPaved
Waterfront Details
Beach Rights
Water Source
Public Water Connected
Sewer
Septic
Flood Zone
No
Construction
Clapboard
Color
White
Roof
Asphalt Shingle
Foundation
Masonry
Exterior Features
ShedPorchBarnGarden Area
Lot Description
Level Lot

Listing & Financials

Property Taxes
$16,958 / Annually
Days on Market
263
MLS #
24130400
MLS Status
Under Contract

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Serena Richards

(203) 273-2073

Brown Harris Stevens

(203) 655-1418

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 8:01 PM UTC.