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280 Hollow Tree Ridge Road

Darien, Connecticut 06820

PENDING$3,395,000
Beds
5
Baths
4 | 2
SqFt
5,579
Acres
1.25
Year Built
1943
Matt Caiola

Matt Caiola

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Pool2-Car Garage3 FireplacesVirtual Tour

About This Home

This elegant and chic stone-and-clapboard colonial is perfectly sited on 1.25 private acres and features spectacular in-ground heated gunite pool, expansive rear bluestone terrace and pool deck, and 5,179 square feet of living space. Perfect for entertaining, the first floor includes a library with gas fireplace, living room with wood-burning fireplace, formal dining room, butlers pantry with wet bar, renovated breakfast room w/custom banquette, kitchen with marble-topped center island, family room with stone fireplace and custom built-ins, 2 half baths, as well as mudroom with two closets. On the second floor you will find 5 generously-sized bedrooms, including fabulous primary suite with vaulted ceiling, renovated master bath with steam shower & radiant heat floors, and his/her closets with custom California closet systems, as well as 3 additional full baths and large laundry room with sink, cabinetry, folding area and hanging rods for drying. Finished lower level adds 400 SF of play/office/gym space and dry storage, plus unfinished portion includes plentiful storage areas. Attached 2-car garage features coin vinyl flooring and electric car charging outlet. This house is a must-see!

Key Facts

City/Town
Darien
Property / Style
Single Family · Colonial
Year Built
1943
Days on Market
1093 days
Beds
5
Baths
4 full · 2 half
Living Area
5,579 sq ft
Lot Size
1.25 acres
Garage / Parking
2 garage
Property Taxes
$28,331 / Annually

Market Snapshot

The Darien Market

Single Family · trailing 12 months

Median Days on Market

67

20 active listings

Median $ / Sq Ft

$726

20 active listings

Sale-to-List Ratio

106.2%

210 sales

How this home compares

List Price

$3.40M

vs $3.92M median

13.5% below median

Price / Sq Ft

$609

vs $726 median

16.1% below median

Days on Market

1093 days

vs 67 days median

1026 days longer than median

Based on 20 active and 210 closed sales (trailing 12 mo) of single family in Darien. Source: SmartMLS · As of September 6, 2026.

Location

280 Hollow Tree Ridge Road, Darien, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$21,037

per month

  • Principal & Interest$17,544
  • Property Taxes$2,361
  • Insurance$1,132
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Darien
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1943
Living Area
5,579 sq ft

Schools

Elementary
Ox Ridge
High
Darien

Interior

Heating
Hot Air
Cooling
Ceiling FansCentral AirZoned
Fireplaces
3
Laundry
Upper Level
Basement
FullPartially FinishedStorageSump Pump
Interior Features
Audio SystemAuto Garage Door OpenerSecurity System
Additional Rooms
FoyerLaundry RoomMud Room

Exterior & Lot

Lot Size
1.25 acres
Garage / Parking
2 garage spacesAttached GarageDrivewayPaved
Waterfront Details
Beach Rights
Pool
In Ground PoolHeatedGunite
Construction
ClapboardStoneWood
Roof
Asphalt Shingle
Foundation
BlockConcrete
Exterior Features
AwningsGarden AreaGrillShedStone WallTerraceUnderground SprinklerUnderground Utilities
Lot Description
Open LotLevel LotLightly WoodedFence - FullFence - Electric Pet

Listing & Financials

Property Taxes
$28,331 / Annually
Days on Market
1093
MLS #
170593534
MLS Status
Under Contract

Similar Properties

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Listed By

Cathleen Morgan

Houlihan Lawrence

Buyer's Agent

Cora Lynch-O'meara

Brown Harris Stevens

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/6/2026. 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 9/6/2026 at 5:00 PM UTC.