366 Hollow Tree Ridge Rd

Darien, CT 06820

$6,195,000
Price
6
Beds
7,356 Sq. Ft.
$842 / Sq. Ft.
7,356
Sq. Ft.
$842
per Sq. Ft.
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Listed By Compass
Listed By Compass

Description

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...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.

Listing Agent

  1. Ashley Mayhew Dineen

    Ashley Mayhew Dineen

    Listing Agent

    Compass

    ashley.dineen@compass.com

    P: (203)-253-9616

    CallTextEmail

Property Details for 366 Hollow Tree Ridge Road

Basement Description
Partial, Full, Heated, Cooled, Partial With Walk-Out
Direct Waterfront
No
Garages Number
4
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Attached Garage, Detached Garage
Swimming Pool
Yes
LISTING UPDATED: 04/08/2026 09:13 PM

Property Details for 366 Hollow Tree Ridge Road

StatusActive
MLS #24165040
Days on Market1
Taxes$45,738 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1776
Lot Size1.75 AC / 76,230 SF
CountyFairfield County
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Location

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Building Information for 366 Hollow Tree Ridge Road

Stories-Year Built1776Building Size-Lot Size1.75 AC / 76,230 SF

Payment Calculator

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$35,007 per month

30 year fixed, 6.46% Interest

Principal and Interest

$31,195

Property Taxes

$3,812

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 366 Hollow Tree Ridge Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Hollow Tree Ridge Rd
  • Elementary School: Ox Ridge
  • High School: Darien
  • Latitude: 41.085666
  • Longitude: -73.49604
  • Middle Jr High School: Middlesex
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Sewer Usage Fee Annual: $1,752
  • Tax Year: July 2025-June 2026
  • Property Tax: $45,738
Interior and Exterior Features
Exterior Features
  • Exterior Features: Underground Sprinkler, Patio
  • Pool Description: Gunite, Heated, In Ground Pool
  • Waterfront Description: Beach Rights
Interior Features
  • Appliances Included: Oven/Range, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Finished, Walk-up
  • Cooling System: Central Air, Ductless
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 6
  • Interior Features: Audio System, Auto Garage Door Opener, Central Vacuum, Security System
  • Laundry Room Info: Main Level, Upper Level
  • Rooms Additional: Breezeway, Laundry Room, Mud Room
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: Built-Ins,Fireplace
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Study
  • Room Width: 15.0
Room 2
  • Room Entry Order: 10
  • Room Features: Book Shelves,Full Bath
  • Room Length: 13.0
  • Room Level: Other
  • Room Type: Bedroom
  • Room Width: 14.0
Room 3
  • Room Entry Order: 11
  • Room Features: 9 ft+ Ceilings
  • Room Length: 27.0
  • Room Level: Upper
  • Room Type: Great Room
  • Room Width: 15.0
Room 4
  • Room Entry Order: 12
  • Room Features: Built-Ins,Fireplace
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Den
  • Room Width: 23.0
Room 5
  • Listing Key: 4ED07E46019A9C61E0631A01100A1338
  • Room Entry Order: 13
  • Room Length: 24.0
  • Room Level: Other
  • Room Type: Bedroom
  • Room Width: 18.0
Room 6
  • Room Entry Order: 2
  • Room Features: Beams,Fireplace
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 33.0
Room 7
  • Room Entry Order: 3
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Formal Dining Room
  • Room Width: 14.0
Room 8
  • Room Entry Order: 4
  • Room Features: Skylight,9 ft+ Ceilings,Breakfast Bar
  • Room Length: 10.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 16.0
Room 9
  • Listing Key: 4ED07E46019A9C61E0631A01100A1338
  • Room Entry Order: 5
  • Room Features: Fireplace
  • Room Length: 19.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 16.0
Room 10
  • Room Entry Order: 6
  • Room Features: Bedroom Suite,Fireplace,Full Bath,Walk-In Closet
  • Room Length: 20.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 16.0
Room 11
  • Room Entry Order: 7
  • Room Features: Beams,Fireplace,Full Bath,Walk-In Closet
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 17.0
Room 12
  • Room Entry Order: 8
  • Room Features: Jack & Jill Bath
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 17.0
Room 13
  • Room Entry Order: 9
  • Room Features: Jack & Jill Bath
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Property
Property and Assessments
  • Construction Description: Frame
  • Exclusions: Chandeliers in: Front hallway, living room, dining room & kitchen (over table)
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Wood Shingle
  • Year Built: 1776
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Description: per tax card
  • Sq Ft Est Heated Below Grade: 685
  • Living Area SQFT Per Public Records: 6101
Lot Information
  • Lot Description: Level Lot, Professionally Landscaped
  • Parcel Number: 103743
  • Sq Ft Est Heated Above Grade: 6671.0
  • Sq Ft Total: 7356.0
  • Zoning: R2
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Tank Size Unknown
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 366 Hollow Tree Ridge Road

DateEvent & SourcePriceAppreciation
Oct 20, 2010

Closed (Public Record)

Public Record #327035526

$1

-100.0% / yr

Apr 26, 2010

Closed (Public Record)

Public Record #289718097

$4,450,000

+81.0% / yr

Nov 26, 2008

Closed (Public Record)

Public Record #259913729

$1,925,000—
DateEvent & SourcePrice
10/20/2010

Closed (Public Record)

Public Record #327035526

$1

-100.0% / yr

04/26/2010

Closed (Public Record)

Public Record #289718097

$4,450,000

+81.0% / yr

11/26/2008

Closed (Public Record)

Public Record #259913729

$1,925,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 366 Hollow Tree Ridge Road

Taxable ValueLand$1,065,750Additions$1,888,880Total$2,954,630
Tax Record2024$45,738 ($3,812 / month)
Home Facts
Beds6Baths5.5Total Finished SqFt6,101 SqFtAbove Grade Finished SqFt6,101 SqFtStories2Lot Size76,230 SqFtStyleSingle Family ResidenceYear Built2010ZoningR2CountyFAIRFIELDAPNDARI M:09 B:119Fireplace TypeHas Fireplace

Schools near 366 Hollow Tree Ridge Road

This home is within Darien School District.
Rating
School
Type
Grades
Distance
Royle Elementary School
Public - PK to 5
Middlesex Middle School
Public - 6 to 8
Darien High School
Public - 9 to 12
Rating
School
Distance
Royle Elementary School
PublicPK to 5

Middlesex Middle School
Public6 to 8

Darien High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 366 Hollow Tree Ridge Road, Darien, CT 06820

366 Hollow Tree Ridge Road is a single family home for sale in Darien, CT 06820. This listing's school district is Darien School District. Nearby schools include Royle Elementary School, Middlesex Middle School and Darien High School. 366 Hollow Tree Ridge Road is a 6-bed, 6-bath, 7,356 sqft single family home built in 1776.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.