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366 Hollow Tree Ridge Road, Darien, CT 06820

Single Family For Sale

$6,195,000
$842/sqft
366 Hollow Tree Ridge Road, Darien, CT Active
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6
Bedrooms
6
Bathrooms
7,356
Sq Ft
1.75
Acres
1776
Year Built

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.

Listed by Ashley Dineen (203) 253-9616 with Compass Connecticut, LLC (203) 423-3100

Listing Snapshot

Price $6,195,000 Days on Market 0 days
Property Tax $45,738/yr Style Colonial
Year Built 1776 Total Sq Ft 7,356
Lot Size 1.75 acres HOA Fees N/A
Bedrooms 6 Full Bathrooms 5
Total Rooms 10 Half Baths 1

Key Features

Interior
  • Audio System
  • Auto Garage Door Opener
  • Central Vacuum
  • Security System
Appliances
  • Oven/Range
  • Wall Oven
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer
Outdoor
  • Underground Sprinkler
  • Patio
  • Gunite
  • Heated
  • In Ground Pool

Structure & Parking

Construction Frame
Roof Wood Shingle
Garage Spaces 4
Garage Type Attached Garage, Detached Garage
Below Grade 685 sq ft

Systems & Utilities

Heat Hot Water
Fuel Oil
Cooling Central Air, Ductless
Hot Water Oil, Tank Size Unknown
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Ox Ridge
Middle Middlesex
High Darien

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $3,812/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Apr 8, 2026 Listed $6,195,000

Frequently Asked Questions

How much does 366 Hollow Tree Ridge Road in Darien, CT cost?
This property is listed at $6,195,000, which works out to $842 per square foot.
How many bedrooms does 366 Hollow Tree Ridge Road have?
This home has 6 bedrooms and 6 bathrooms.
What is the square footage of 366 Hollow Tree Ridge Road?
The home is 7,356 square feet, situated on 1.75 acres.
When was 366 Hollow Tree Ridge Road in Darien built?
This property was built in 1776.
Is 366 Hollow Tree Ridge Road, Darien, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 366 Hollow Tree Ridge Road, Darien in?
This home is served by the Darien public school system, with Ox Ridge as the elementary school and Darien as the high school.
How do I schedule a tour of 366 Hollow Tree Ridge Road, Darien, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Ashley Dineen · (203) 253-9616

Compass Connecticut, LLC · (203) 423-3100

MLS# 24165040 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Apr 8, 2026 9:13 PM UTC