5 Cross Road
Darien, Connecticut 06820
- Beds
- 4
- Baths
- 3 | 2
- SqFt
- 4,361
- Acres
- 0.70
- Year Built
- 1932
- Neighborhood
- Tokeneke
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Set within Darien's coveted private Tokeneke Association, 5 Cross Road is a quintessential stone Colonial gracefully positioned on a private .70 acre property. Timeless architectural character, exceptional privacy, and inviting living spaces define this distinctive residence in one of the town's most sought-after coastal neighborhoods.The thoughtfully updated kitchen serves as the heart of the home, while an extraordinary family room with soaring ceilings and abundant natural light offers a dramatic yet welcoming setting for everyday living and entertaining. A desirable first-floor primary suite provides comfort and convenience, creating an ideal layout for modern living. Classic details and generous rooms throughout complement the home's enduring stone facade and beautifully secluded grounds. Enjoy the rare combination of a tranquil residential setting, private association lifestyle, and convenient access to Darien's village, schools, train, beaches, and waterfront. A special Tokeneke offering where classic New England charm meets effortless, refined living.
Key Facts
Market Snapshot
The Darien Market
Single Family · trailing 12 months
Active Listings
26
24 under contract
Median List Price
$3.91M
26 active listings
Median Closed Price
$2.88M
215 sales
Median Days on Market
43
26 active listings
Median $ / Sq Ft
$758
26 active listings
Sale-to-List Ratio
106.3%
215 sales
How this home compares
List Price
$3.79M
vs $3.91M median
In line with median
Price / Sq Ft
$870
vs $758 median
14.8% above median
Days on Market
0 days
vs 43 days median
43 days fresher than median
Based on 26 active and 215 closed sales (trailing 12 mo) of single family in Darien. Source: SmartMLS · As of September 28, 2026.
Location
5 Cross Road, Darien, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$20,260
- Property Taxes$2,620
- Insurance$1,265
- HOA$112
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1932
- New Construction
- No/Resale
- Living Area
- 4,361 sq ft
Schools
- Elementary
- Tokeneke
- High
- Darien
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Gas RangeRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- Crawl SpaceUnfinished
- Additional Rooms
- FoyerLaundry Room
Exterior & Lot
- Lot Size
- 0.70 acres
- Zoning
- R-1
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Walk to WaterWater Community
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- Yes
- Construction
- Stone
- Color
- stone
- Roof
- Slate
- Foundation
- ConcreteStone
- Exterior Features
- AwningsGarden AreaPatio
- Lot Description
- SecludedCorner LotLevel LotProfessionally Landscaped
HOA / Association
- Fee
- $1,349 / Annually
Listing & Financials
- Property Taxes
- $31,441 / Annually
- Days on Market
- 0
- MLS #
- 24210059
- MLS Status
- Coming Soon
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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 9/28/2026. 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 9/28/2026 at 10:35 PM UTC.