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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.
| DAYS ON MARKET | 4 | LAST UPDATED | 4/8/2026 |
|---|---|---|---|
| YEAR BUILT | 1776 | GARAGE SPACES | 4.0 |
| COUNTY | Fairfield | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| Elementary School | Ox Ridge |
|---|---|
| Jr. High School | Middlesex |
| High School | Darien |
| ADDITIONAL DETAILS | |
| AIR | Central Air, Ductless |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Dryer, Oven, Range, Refrigerator, Washer |
| BASEMENT | Full, Partial, Walk-Out Access, Yes |
| CONSTRUCTION | Clapboard, Frame |
| FIREPLACE | Yes |
| GARAGE | Attached Garage, Yes |
| HEAT | Hot Water, Oil |
| INTERIOR | Central Vacuum, Sound System |
| LOT | 1.75 acre(s) |
| LOT DESCRIPTION | Level |
| PARKING | Garage Door Opener, Attached |
| POOL DESCRIPTION | Gunite, Heated, Outdoor Pool, In Ground |
| SEWER | Public Sewer |
| STYLE | Colonial |
| TAXES | 45738 |
| WATER | Public |
| WATERFRONT DESCRIPTION | Beach Access |
| ZONING | R2 |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing courtesy of Compass Connecticut, LLC
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This IDX solution is (c) Diverse Solutions 2026.