366 Hollow Tree Ridge Road
Darien, Connecticut 06820
- Beds
- 6
- Baths
- 5 | 1
- SqFt
- 7,356
- Acres
- 1.75
- Year Built
- 1776
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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.
Key Facts
- City/Town
- Darien
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1776
- Days on Market
- 109 days
- Beds
- 6
- Baths
- 5 full · 1 half
- Living Area
- 7,356 sq ft
- Lot Size
- 1.75 acres
- Garage / Parking
- 4 garage
- Property Taxes
- $45,738 / Annually
Market Snapshot
The Darien Market
Single Family · trailing 12 months
Active Listings
25
54 under contract
Median List Price
$3.80M
25 active listings
Median Closed Price
$2.71M
211 sales
Median Days on Market
51
25 active listings
Median $ / Sq Ft
$733
25 active listings
Sale-to-List Ratio
106.3%
211 sales
How this home compares
List Price
$6.20M
vs $3.80M median
63.0% above median
Price / Sq Ft
$842
vs $733 median
14.9% above median
Days on Market
109 days
vs 51 days median
58 days longer than median
Based on 25 active and 211 closed sales (trailing 12 mo) of single family in Darien. Source: SmartMLS · As of July 27, 2026.
Location
366 Hollow Tree Ridge Road, Darien, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$31,586
- Property Taxes$3,812
- Insurance$2,065
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Darien
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1776
- New Construction
- No/Resale
- Living Area
- 7,356 sq ft
- Below Grade
- 685 sq ft
Schools
- Elementary
- Ox Ridge
- High
- Darien
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central AirDuctless
- Fireplaces
- 6
- Laundry
- Main LevelUpper Level
- Appliances
- Oven/RangeWall OvenRefrigeratorDishwasherWasherDryer
- Basement
- PartialFullHeatedCooledPartial With Walk-Out
- Interior Features
- Audio SystemAuto Garage Door OpenerCentral VacuumSecurity System
- Additional Rooms
- BreezewayLaundry RoomMud Room
Exterior & Lot
- Lot Size
- 1.75 acres
- Zoning
- R2
- Garage / Parking
- 4 garage spacesAttached GarageDetached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Pool
- GuniteHeatedIn Ground Pool
- Construction
- Clapboard
- Roof
- Wood Shingle
- Foundation
- Concrete
- Exterior Features
- Underground SprinklerPatio
- Lot Description
- Level LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $45,738 / Annually
- Days on Market
- 109
- MLS #
- 24165040
- MLS Status
- Under Contract
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/27/2026 at 10:05 AM UTC.