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82 Arrowhead Way

Darien, Connecticut 06820

PENDING$8,650,000
Beds
5
Baths
5 | 1
SqFt
5,823
Acres
2.11
Year Built
1925
Matt Caiola

Matt Caiola

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WaterfrontDock / MooringPool3-Car Garage4 FireplacesVirtual Tour

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

City/Town
Darien
Neighborhood
Tokeneke
Property / Style
Single Family · Colonial
Year Built
1925
Days on Market
54 days
Beds
5
Baths
5 full · 1 half
Living Area
5,823 sq ft
Lot Size
2.11 acres
Garage / Parking
3 garage · 12 total
Property Taxes
$65,686 / Annually
HOA Fee
$4,000 / Annually

Market Snapshot

The Darien Market

Single Family · trailing 12 months

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$52,794

per 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

City/Town
Darien
Neighborhood
Tokeneke
County
Fairfield

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

Similar Properties

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

Listed By

Becky Munro

(203) 858-6182

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 6:35 AM UTC.