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366 Hollow Tree Ridge Road

Darien, Connecticut 06820

PENDING$6,195,000
Beds
6
Baths
5 | 1
SqFt
7,356
Acres
1.75
Year Built
1776
Matt Caiola

Matt Caiola

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Pool4-Car Garage6 Fireplaces

About This Home

Set along one of Hollow Tree Ridge Road's most desirable stretches, 366 Hollow Tree Ridge Road is a masterfully restored and expanded residence that artfully blends historic character with refined modern living. Reimagined by renowned builder Bo Malpass, the home offers 6 bds, 5.1 baths across 7,356 sq feet. Original character is preserved through antique beams and wide plank wood floors, while modern updates introduce a seamless flow and elevated functionality. Interiors curated by Kristen Fine enhance the home's cohesive aesthetic with understated luxury and timeless finishes. Sun-drenched living spaces unfold effortlessly, creating an ideal setting for both everyday living and elegant entertaining. The custom-designed Poggenpohl kitchen serves as the heart of the home, complemented by multiple inviting gathering spaces. A spacious primary suite and well-appointed secondary bedrooms provide comfort, scale, and flexibility. Set on 1.75 acres of beautifully landscaped grounds, the property features a Gunite pool and a charming guest cottage connected by a breezeway ideal as an in-law suite, private retreat, or dedicated work-from-home space. Ideally located with convenient access to town, train, and Darien's top-rated schools, this exceptional offering presents a rare opportunity to own a turnkey home where historic integrity and modern sophistication converge.

Key Facts

City/Town
Darien
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1776
Days on Market
109 days
Beds
6
Baths
5 full · 1 half
Living Area
7,356 sq ft
Lot Size
1.75 acres
Garage / Parking
4 garage
Property Taxes
$45,738 / Annually

Market Snapshot

The Darien Market

Single Family · trailing 12 months

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

$6.20M

vs $3.80M median

63.0% above median

Price / Sq Ft

$842

vs $733 median

14.9% above median

Days on Market

109 days

vs 51 days median

58 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

366 Hollow Tree Ridge Road, Darien, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$37,463

per month

  • Principal & Interest$31,586
  • Property Taxes$3,812
  • Insurance$2,065
  • 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
Colonial
Year Built
1776
New Construction
No/Resale
Living Area
7,356 sq ft
Below Grade
685 sq ft

Schools

Elementary
Ox Ridge
High
Darien

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central AirDuctless
Fireplaces
6
Laundry
Main LevelUpper Level
Appliances
Oven/RangeWall OvenRefrigeratorDishwasherWasherDryer
Basement
PartialFullHeatedCooledPartial With Walk-Out
Interior Features
Audio SystemAuto Garage Door OpenerCentral VacuumSecurity System
Additional Rooms
BreezewayLaundry RoomMud Room

Exterior & Lot

Lot Size
1.75 acres
Zoning
R2
Garage / Parking
4 garage spacesAttached GarageDetached Garage
Waterfront Details
Beach Rights
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Pool
GuniteHeatedIn Ground Pool
Construction
Clapboard
Roof
Wood Shingle
Foundation
Concrete
Exterior Features
Underground SprinklerPatio
Lot Description
Level LotProfessionally Landscaped

Listing & Financials

Property Taxes
$45,738 / Annually
Days on Market
109
MLS #
24165040
MLS Status
Under Contract

Similar Properties

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

Listed By

Ashley Dineen

(203) 253-9616

Compass Connecticut, LLC

(203) 423-3100

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 10:05 AM UTC.