561 Middlesex Road
Darien, Connecticut 06820
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,411
- Acres
- 2.64
- Year Built
- 1856
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
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
21.1% 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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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 8:01 PM UTC.