82 Arrowhead Way
Darien, Connecticut 06820
- Beds
- 5
- Baths
- 5 | 1
- SqFt
- 5,823
- Acres
- 2.11
- Year Built
- 1925
- Neighborhood
- Tokeneke
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
(Don't miss the spectacular waterfront video). On the water in the Tokeneke Association, Short Rocks Manor is poised at the very tip of Arrowhead Way, high above Scotts Cove and Long Island Sound. This breathtaking, updated 1925 English-style stone manor sits on 2.11 acres which includes .362 acres of designated OPEN SPACE. The 5,823 square feet of exquisite craftmanship houses five bedrooms - including a private-entrance apartment perfect for guests or family. Up the circular drive, you enter through a private stone rose-filled courtyard into the fabulous foyer with fireplace and step in the soaring two-story great room with floor to ceiling windows of glass that open directly onto your waterfront terrace, with the cove and Sound shimmering beyond. Every principal room has been oriented to capture the water. The primary bedroom suite window wall overlooks the ever-changing beauty of the sea. The kitchen leads to a private patio. Acres of landscaped gardens unfold across multiple levels, a private swimming pool is nestled within its own secluded garden sanctuary, and a whimsical Fairy Path winds upward to a hidden garden perched high above the cove creating a bird and wildlife sanctuary. The separate viewing terrace overlooks the water and your own private dock and is perfect for evening cocktails or simply watching the sun set over Long Island Sound. This home and property are rare. Make it your own.
Key Facts
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
$8.65M
vs $3.80M median
2.3× the median
Price / Sq Ft
$1,485
vs $733 median
2.0× the median
Days on Market
54 days
vs 51 days median
3 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
82 Arrowhead Way, Darien, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$44,104
- Property Taxes$5,474
- Insurance$2,883
- HOA$333
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
- 1925
- New Construction
- No/Resale
- Living Area
- 5,823 sq ft
Schools
- Elementary
- Tokeneke
- High
- Darien
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 4
- Laundry
- Main Level
- Appliances
- Oven/RangeWall OvenRefrigeratorDishwasherWasherDryer
- Basement
- Crawl Space
- In-Law Apartment
- YesUpper LevelSeparate Entry
- Interior Features
- Security System
- Additional Rooms
- Foyer
Exterior & Lot
- Lot Size
- 2.11 acres
- Zoning
- R-1
- Garage / Parking
- 3 garage spaces12 total parking spacesAttached GarageDrivewayPrivatePavedAsphalt
- Waterfront
- Direct waterfront
- Waterfront Details
- L. I. Sound FrontageWalk to WaterDock or MooringAssociation RequiredView
- Water Source
- Public Water Connected
- Sewer
- Septic
- Pool
- GuniteHeatedTileIn Ground Pool
- Construction
- StoneWood
- Color
- Gray Stone
- Roof
- Slate
- Foundation
- Stone
- Exterior Features
- TerraceGuttersLightingFrench DoorsUnderground Sprinkler
- Lot Description
- Water View
HOA / Association
- Fee
- $4,000 / Annually
Listing & Financials
- Property Taxes
- $65,686 / Annually
- Days on Market
- 54
- MLS #
- 24180009
- 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 6:35 AM UTC.