280 Hollow Tree Ridge Road
Darien, Connecticut 06820
- Beds
- 5
- Baths
- 4 | 2
- SqFt
- 5,579
- Acres
- 1.25
- Year Built
- 1943
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
20
22 under contract
Median List Price
$3.92M
20 active listings
Median Closed Price
$2.87M
210 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 3, 2026per 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.