About the 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.
Rooms & Interior
Room Details
-
Living Room (Main Level)
Beams, Fireplace
-
Bedroom (Upper Level)
Jack & Jill Bath
-
Bedroom (Other Level)
-
Study (Main Level)
Built-Ins, Fireplace
-
Formal Dining Room (Main Level)
-
Primary Bedroom (Upper Level)
Bedroom Suite, Fireplace, Full Bath, Walk-In Closet
-
Bedroom (Upper Level)
Beams, Fireplace, Full Bath, Walk-In Closet
-
Bedroom (Other Level)
Book Shelves, Full Bath
-
Kitchen (Main Level)
Skylight, 9 ft+ Ceilings, Breakfast Bar
-
Family Room (Main Level)
Fireplace
-
Bedroom (Main Level)
Jack & Jill Bath
-
Den (Main Level)
Built-Ins, Fireplace
-
Great Room (Upper Level)
9 ft+ Ceilings
-
Living Room (Main Level)
Beams, Fireplace
-
Bedroom (Upper Level)
Jack & Jill Bath
-
Bedroom (Other Level)
-
Study (Main Level)
Built-Ins, Fireplace
-
Formal Dining Room (Main Level)
-
Primary Bedroom (Upper Level)
Bedroom Suite, Fireplace, Full Bath, Walk-In Closet
-
Bedroom (Upper Level)
Beams, Fireplace, Full Bath, Walk-In Closet
-
Bedroom (Other Level)
Book Shelves, Full Bath
-
Kitchen (Main Level)
Skylight, 9 ft+ Ceilings, Breakfast Bar
-
Family Room (Main Level)
Fireplace
-
Bedroom (Main Level)
Jack & Jill Bath
-
Den (Main Level)
Built-Ins, Fireplace
-
Great Room (Upper Level)
9 ft+ Ceilings
-
Other Rooms
Breezeway, Laundry room, Mud room
Home Features
Heating
- Fireplaces: 6
- Heating: hot water
- Heat fuel type: oil
- Fuel tank: in basement
Interior Features
- Audio system
- Auto garage door opener
- Central vacuum
- Security system
Appliances
- Oven/range
- Wall oven
- Refrigerator
- Dishwasher
- Washer
- Dryer
Basement
- Partial
- Full
- Heated
- Cooled
- Partial with walk-out
Exterior Features
- Underground sprinkler
- Patio
Property Details
Parking
- Garage spaces: 4
- Attached garage
- Detached garage
Swimming Pool
- Gunite
- Heated
- In ground pool
Lot Details
- Lot surface: 1.75 acres
- Level lot
- Professionally landscaped
Utilities
- Water: public water connected
- Sewage: pub. sewer connected
- Sewage fee: $ 1,752 per year
Construction Details
- Style
- colonial
- Construction year
- 1776
- Exterior Siding
- clapboard
- Foundation
- concrete
- Roof
- wood shingle
Area & Town
This home is located in Northern Darien neighborhood, in the town of Darien.
- $2.69M med. price
- 19 homes for sale
- $2.35M med. price
- 44 homes for sale
Finance & Listing Info
| Status |
Under contract |
| Listing date |
April 08, 2026 |
| List price |
$ 6,195,000 |
| Current price |
$ 6,195,000 |
| Tax amount |
$ 45,738 |
| Tax year |
july 2025-june 2026 |
| MLS ID |
#24165040 |
| List Agent |
Ashley Dineen |
| List Office |
Compass Connecticut, LLC |
(c) 2026 Based on information provided to and compiled by the Smart MLS, Inc.
