27 Hillsley Road, Darien, CT 06820 - Photo 1

1/1

$5,200,000

Sold
Closed
Single Family
6 Beds
4 Full Baths
2 Partial Baths
7,670 Sq. Ft.
3 Car Garage

1/1

Property Description

Exquisitely renovated center hall colonial set on two perfectly manicured acres at end of quiet, private cul-de-sac, offering exceptional space & timeless appeal for both everyday living & entertaining. Renovated in 2023 by ERI Building & Design, this stunning six-bedroom home with private office, four full & two half baths showcases impeccable craftsmanship & sophisticated design throughout. Dramatic open-concept kitchen features two oversized islands, walk-in pantry, Sub-Zero refrigerator & freezer, & an inviting breakfast area flowing seamlessly into soaring great room overlooking expansive rear lawn & tennis court with room for pool - perfect setting for gathering with family & friends. Light-filled sunroom provides ideal spot for relaxing with morning coffee while enjoying peaceful views of property. Designed for elegant entertaining, the home features gracious formal living room with fireplace, stunning bar & lounge area, wine pantry, & formal dining room with butler's pantry. Luxurious first-floor suite provides exceptional comfort & privacy for visitors. Upstairs luxurious primary suite with fireplace & spa-like ambiance, creates peaceful retreat. Four additional generously sized bedrooms feature beautifully appointed jack-jill baths. Private office just across hall creates ultimate work-from-home setting. Thoughtfully designed lower level provides flexible, ample space for gym or playroom. This truly exceptional home offering elegance & an unparalleled lifestyle.

Full Property Details

Full Property Details for 27 Hillsley Rd

General

Sold For: $5,200,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24175837
Added to Site: 57 day(s) ago

Interior

Number of Rooms: 9
Rooms/Areas: Foyer, Laundry Room, Mud Room
Interior Features: Security System
Fireplace: Yes
Number of Fireplaces: 2
Appliances: Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

Total Bathrooms: 6
Full Bathrooms: 4
Half Bathrooms: 2

Bedrooms

Total Bedrooms: 6
Primary Bedroom: Primary Bedroom - Fireplace, 21 x 28, Upper
Bedroom 1: Bedroom, 20 x 13, Main
Bedroom 2: Bedroom, 14 x 15, Upper
Bedroom 3: Bedroom, 14 x 17, Upper
Bedroom 4: Bedroom, 16 x 14, Upper
Bedroom 5: Bedroom, 18 x 15, Upper

Other Rooms

Living Room: Living Room - Fireplace, 20 x 28, Main
Family Room: Family Room - Fireplace, 22 x 20, Main
Kitchen: Kitchen, 36 x 18, Main
Dining Room: Dining Room, 20 x 15, Main
Office: Office, 14 x 13, Upper
Game room: Yes
Game Room: Rec/Play Room, 21 x 50, Lower
Rec Room: 21 x 50, Lower
Laundry: Upper Level

Parking

Garage: Yes
Attached garage: Yes
Garage Spaces: 3
Parking: Attached Garage

Location

County: Fairfield
Driving Directions: Brookside to Hillsley Road

School Information

Elementary School: Ox Ridge
Middle School: Middlesex
High School: Darien

Heating & Cooling

Cooling Type: Central Air
Heating Type: Hot Water, Oil
Heating Fuel: Oil
Water Heater: Oil, 100 Gallon Tank

Utilities

Sewer: Septic
Water: Private Well

Structural Information

Architectural Style: Colonial
Construction Status: No/Resale
Exterior Const.: Wood
Basement Desc.: Full, Fully Finished
Roof: Asphalt Shingle
Attic: Yes
Square Feet: 7,670
Above Ground: 6,620 Sq. Ft.
Below Ground: 1,050 Sq. Ft.
Year Built: 2000

Lot Features

Lot Size (Acres): 2
Zoning: R2
Lot Description: Level Lot, On Cul-De-Sac, Professionally Landscaped

Water Features

Water Front Desc.: Beach Rights

Financial Considerations

Assessment Amount: $2,688,630
Tax Year: July 2025-June 2026

Disclosures and Reports

Property ID: 102629

Listed by Houlihan Lawrence, Deb Hidy
Sold by Compass Connecticut, LLC, The Jennifer Leahy Team, Katharine Gray Bunoski

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Listing agent

— 27 Hillsley Rd —

Deb Hidy

Houlihan Lawrence

Agent Contact: (203) 505-8200 Office Contact: (203) 655-8238

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Schools

Schools serving 27 Hillsley Rd

School District:Darien School District

Name	Grades	Distance
Ox Ridge Elementary School 395 Mansfield Avenue, Darien, CT 06820	K-5	0.8 mi
Middlesex Middle School 204 Hollow Tree Ridge Road, Darien, CT 06820	6-8	2.9 mi
Darien High School 80 High School Lane, Darien, CT 06820	9-12	2.1 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 27 Hillsley Rd

Date

Details

Price

Change

Source

6/25/2026

Sold

$5,200,000

-4.59%

MLS

5/15/2026

Listed

$5,450,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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2
Beds
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Sq. Ft.

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Beds
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Beds
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Total Baths
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Sq. Ft.

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Beds
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Total Baths
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Single Family
Closed
Updated 11 days ago

5
Beds
7
Total Baths
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Sq. Ft.

Listed by Houlihan Lawrence
Sold by Compass Connecticut, LLC

27 Hillsley Road, Darien, CT 06820 (MLS# 24175837) is a Single Family property that was sold at $5,200,000 on June 25, 2026. Want to learn more about 27 Hillsley Road? Do you have questions about finding other Single Family real estate for sale in Darien? You can browse all Darien real estate or contact a Coldwell Banker agent to request more information.

27 Hillsley Rd Darien, CT 06820