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253 Tokeneke Road

Darien, Connecticut 06820

PENDING$1,450,000
Beds
3
Baths
2 | 1
SqFt
2,208
Year Built
1910
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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1 Fireplace

About This Home

Steeped in history yet thoughtfully reimagined for modern living, The Barnacle is a beautifully renovated 1910 barn in the heart of Darien. Renovated in 2019, this one-of-a-kind residence blends timeless character with contemporary design. The dramatic great room showcases soaring 30-foot cathedral ceilings, exposed wood beams, an oversized picture window, and a classic fireplace anchoring the open living and dining spaces. The chic kitchen flows seamlessly for effortless entertaining and everyday living. A desirable first-floor primary suite opens directly to the bluestone patio, while two additional bedrooms upstairs include one with a private balcony. Professionally landscaped grounds offer a level lawn, privacy, and inviting outdoor spaces. Enjoy easy access to Darien's vibrant town center, train, and shopping, while nearby Rowayton offers waterfront charm, a weekly farmers market, and the celebrated Shakespeare on the Sound performances.

Key Facts

City/Town
Darien
Neighborhood
N/A
Property / Style
Condo · Other
Year Built
1910
Days on Market
48 days
Beds
3
Baths
2 full · 1 half
Living Area
2,208 sq ft
Garage / Parking
4 total
Property Taxes
$11,202 / Annually

Market Snapshot

The Darien Market

Condo · trailing 12 months

Median Days on Market

48

2 active listings

Median $ / Sq Ft

$1,043

2 active listings

Sale-to-List Ratio

105.7%

17 sales

How this home compares

List Price

$1.45M

vs $1.22M median

18.7% above median

Price / Sq Ft

$657

vs $1,043 median

37.0% below median

Days on Market

48 days

vs 48 days median

In line with median

Based on 2 active and 17 closed sales (trailing 12 mo) of condo in Darien. Source: SmartMLS · As of July 28, 2026.

Location

253 Tokeneke Road, Darien, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,810

per month

  • Principal & Interest$7,393
  • Property Taxes$934
  • Insurance$483
  • 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
Condo
Subtype
Condominium
Style
Other
Year Built
1910
New Construction
No/Resale
Living Area
2,208 sq ft

Schools

Elementary
Tokeneke
High
Darien

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Appliances
Electric RangeRefrigeratorDishwasherWasherDryer
Basement
None
Interior Features
Open Floor Plan
Additional Rooms
Laundry Room

Exterior & Lot

Zoning
R-1
Garage / Parking
4 total parking spacesPavedDriveway
Waterfront Details
Beach Rights
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Color
Red
Lot Description
Level Lot

Listing & Financials

Property Taxes
$11,202 / Annually
Days on Market
48
MLS #
24182568
MLS Status
Under Contract

Similar Properties

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

Listed By

Genevieve Schettino

(203) 604-5270

Compass Connecticut, LLC

(203) 423-3100

Co-Listed By

Amanda Davenport

Compass Connecticut, LLC

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 7:10 AM UTC.