8 days on market
Under Contract

366 Hollow Tree Ridge Road, Darien CT 06820

Current Price: $6,195,000

6 beds 6 baths 7356 sq. ft

Last Update: 7/19/2026

Property Type: Single Family For Sale

Public Remarks

Set along one of Hollow Tree Ridge Roads 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 homes 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 Dariens top-rated schools, this exceptional offering presents a rare opportunity to own a turnkey home where historic integrity and modern sophistication converge.

Map to Property at 366 Hollow Tree Ridge Road, Darien CT 06820


Hollow Tree Ridge Rd

Residential Property Information for 366 Hollow Tree Ridge Road, Darien CT 06820

MLS #: 24165040

Style: Colonial

Color:

Total Rooms:

Bedrooms: 6

Bathrooms: 6

Acres: 1.75

Year Built: 1776 (Public Records)

New Construction: No/Resale

Home Warranty Offered:

Property Tax: $45,738

Zoning: R2

Mil Rate:

Assessed Value: $2,954,630 

Potential Short Sale:

Square Footage: Estimated HEATED Sq.Ft. above grade is 6671; below grade sq feet total is 685; total sq ft is 7356

Features
Appliances Incl.: Oven/Range,Wall Oven,Refrigerator,Dishwasher,Washer,Dryer
Laundry Location & Info: Main Level,Upper Level 
Fireplaces: 6
Interior Features: Audio System,Auto Garage Door Opener,Central Vacuum,Security System
Basement Desc.: Partial,Full,Heated,Cooled,Partial With Walk-Out
Exterior Siding: Clapboard
Exterior Features: Underground Sprinkler,Patio
Foundation: Concrete
Roof: Wood Shingle
Parking Spaces: 4
Garage/Parking Type: Attached Garage,Detached Garage
Swimming Pool: 1
Waterfront Feat.: Beach Rights
Lot Description: Level Lot,Professionally Landscaped
Occupied: Owner
Utility Information

Hot Water System

Heat Type:

Fueled By: Hot Water.

Cooling: Central Air,Ductless

Fuel Tank Location: In Basement

Water Service: Public Water Connected

Sewage System: Public Sewer Connected

School Information

Elementary: Ox Ridge

Intermediate:

Middle: Middlesex

High School: Darien

Marketing History

Current List Price: $6,195,000

Original List Price: $6,195,000

DOM: 8

Listing Date: 4/8/2026

Last Updated: 4/16/2026 9:56:04 PM

Listing Agent and Broker

List Agent Name: Ashley Dineen

List Office Name: Compass Connecticut, LLC