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.
Under contract
$6,195,000
366 Hollow Tree Ridge Road, Darien, CT 06820
6beds
7,356sqft
:
Get pre-qualified$40,167/mo
Single Family Residence
Built in 1776
1.75 Acres Lot
$-- Zestimate®
$842/sqft
$-- HOA
What's special
Timeless finishesElevated functionalityAntique beamsSun-drenched living spacesGunite poolUnderstated luxuryWide plank wood floors
- 111 days |
- 201 |
- 2 |
Zillow last checked:
Listing updated:
Listed by:
The Legacy Team at Compass,
Ashley Dineen (203)253-9616,
Compass Connecticut, LLC 203-423-3100
Source: Smart MLS,MLS#: 24165040
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Rooms
- Room types: Breezeway, Laundry
Primary bedroom
- Features: Bedroom Suite, Fireplace, Full Bath, Walk-In Closet(s)
- Level: Upper
- Area: 320 Square Feet
- Dimensions: 16 x 20
Bedroom
- Features: Beamed Ceilings, Fireplace, Full Bath, Walk-In Closet(s)
- Level: Upper
- Area: 204 Square Feet
- Dimensions: 17 x 12
Bedroom
- Features: Jack & Jill Bath
- Level: Main
- Area: 187 Square Feet
- Dimensions: 17 x 11
Bedroom
- Features: Jack & Jill Bath
- Level: Upper
- Area: 180 Square Feet
- Dimensions: 12 x 15
Bedroom
- Features: Bookcases, Full Bath
- Level: Other
- Area: 182 Square Feet
- Dimensions: 14 x 13
Bedroom
- Level: Other
- Area: 432 Square Feet
- Dimensions: 18 x 24
Den
- Features: Built-in Features, Fireplace
- Level: Main
- Area: 322 Square Feet
- Dimensions: 23 x 14
Dining room
- Level: Main
- Area: 280 Square Feet
- Dimensions: 14 x 20
Family room
- Features: Fireplace
- Level: Main
- Area: 304 Square Feet
- Dimensions: 16 x 19
Great room
- Features: High Ceilings
- Level: Upper
- Area: 405 Square Feet
- Dimensions: 15 x 27
Kitchen
- Features: Skylight, High Ceilings, Breakfast Bar
- Level: Main
- Area: 160 Square Feet
- Dimensions: 16 x 10
Living room
- Features: Beamed Ceilings, Fireplace
- Level: Main
- Area: 462 Square Feet
- Dimensions: 33 x 14
Study
- Features: Built-in Features, Fireplace
- Level: Main
- Area: 210 Square Feet
- Dimensions: 15 x 14
Heating
- Hot Water, Oil
Cooling
- Central Air, Ductless
Appliances
- Included: Oven/Range, Oven, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Main Level, Upper Level, Mud Room
Features
- Sound System, Central Vacuum
- Basement: Partial,Full,Heated,Cooled
- Attic: Finished,Walk-up
- Number of fireplaces: 6
Interior area
- Total structure area: 7,356
- Total interior livable area: 7,356 sqft
- Finished area above ground: 6,671
- Finished area below ground: 685
Property
Parking
- Total spaces: 4
- Parking features: Attached, Detached, Garage Door Opener
- Attached garage spaces: 4
Features
- Patio & porch: Patio
- Exterior features: Underground Sprinkler
- Has private pool: Yes
- Pool features: Gunite, Heated, In Ground
- Waterfront features: Beach Access
Lot
- Size: 1.75 Acres
- Features: Level, Landscaped
Details
- Parcel number: 103743
- Zoning: R2
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter
- Roof: Wood
Condition
- New construction: No
- Year built: 1776
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Darien
Financial & listing details
- Price per square foot: $842/sqft
- Tax assessed value: $2,954,630
- Annual tax amount: $45,738
- Date on market: 4/8/2026
- Exclusions: Chandeliers in: Front hallway, living room, dining room & kitchen (over table)
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 4/16/2026 | Pending sale | $6,195,000$842/sqft |
Source:  Smart MLS #24165040 Report a problem | ||
| 4/8/2026 | Listed for sale | $6,195,000+39.2%$842/sqft |
Source: Smart MLS #24165040 Report a problem | ||
| 4/26/2010 | Sold | $4,450,000-2.2%$605/sqft |
Source: Public Record Report a problem | ||
| 3/30/2010 | Listed for sale | $4,550,000+136.4%$619/sqft |
Source: William Pitt Sotheby's International Realty #14801 Report a problem | ||
| 11/26/2008 | Sold | $1,925,000$262/sqft |
Source: Smart MLS #98383430 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $45,738 +5.4% | $2,954,630 |
| 2024 | $43,404 +19.5% | $2,954,630 +43.3% |
| 2023 | $36,318 +2.2% | $2,062,340 |
| 2022 | $35,534 +2.3% | $2,062,340 |
| 2021 | $34,730 +2.9% | $2,062,340 |
| 2020 | $33,740 -0.7% | $2,062,340 |
| 2019 | $33,967 -24.2% | $2,062,340 -26% |
| 2018 | $44,812 -0.5% | $2,786,840 |
| 2017 | $45,035 +4.5% | $2,786,840 +2% |
| 2016 | $43,104 +2.7% | $2,733,290 |
| 2015 | $41,956 +2.3% | $2,733,290 |
| 2014 | $41,027 +65.8% | $2,733,290 +45.5% |
| 2013 | $24,742 +11.6% | $1,878,660 +7.4% |
| 2012 | $22,178 +3.9% | $1,749,020 |
| 2011 | $21,338 +34.7% | $1,749,020 +29.6% |
| 2010 | $15,838 +3.3% | $1,349,040 |
| 2009 | $15,339 -2.2% | $1,349,040 +25.2% |
| 2008 | $15,684 +4.9% | $1,077,930 |
| 2007 | $14,951 +3.5% | $1,077,930 |
| 2006 | $14,444 -28% | $1,077,930 -30% |
| 2005 | $20,049 +55.6% | $1,539,900 +42.9% |
| 2004 | $12,881 +25.3% | $1,077,930 +37% |
| 2003 | $10,279 -6.9% | $787,080 |
| 2001 | $11,035 +7.4% | $787,080 -30% |
| 2000 | $10,279 +4.1% | $1,124,400 +101.9% |
| 1999 | $9,870 | $556,990 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 06820
Nearby schools
GreatSchools rating
- 10/10Ox Ridge Elementary SchoolGrades: PK-5Distance: 1.3 mi
- 10/10Middlesex Middle SchoolGrades: 6-8Distance: 0.8 mi
- 10/10Darien High SchoolGrades: 9-12Distance: 0.3 mi
Schools provided by the listing agent
- Elementary: Ox Ridge
- Middle: Middlesex
- High: Darien
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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