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$5,450,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 4 Full Baths
  • 2 Partial Baths
  • 7,670 Sq. Ft.
  • 3 Car Garage
  • Updated 16 hours ago
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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 for 27 Hillsley Rd

General

  • Price: $5,450,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24175837
  • Updated: 5/15/2026
  • Added to Site: 1 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

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Listing agent

— 27 Hillsley Rd —

  • Deb Hidy

    Houlihan Lawrence

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

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 27 Hillsley Rd

School District:Darien School District
NameGradesDistance
Ox Ridge Elementary School
395 Mansfield Avenue, Darien, CT 06820
K-50.8 mi
Middlesex Middle School
204 Hollow Tree Ridge Road, Darien, CT 06820
6-82.9 mi
Darien High School
80 High School Lane, Darien, CT 06820
9-122.1 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/15/2026
Listed
$5,450,000
91.56%
MLS
10/08/2020
Sold
$2,845,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 27 Hillsley Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$41,620
5%
$2,688,630
—
2023
$39,496
10%
$2,688,630
32%
2023
$35,991
2%
$2,043,790
—
2022
$35,215
2%
$2,043,790
—
2021
$34,417
3%
$2,043,790
—
2020
$33,375
-1%
$2,043,790
—
2019
$33,661
-16%
$2,043,790
-18%
2018
$40,266
—
$2,504,110
—
2017
$40,466
2%
$2,504,110
—
2016
$39,490
3%
$2,504,110
—
2015
$38,438
2%
$2,504,110
—
2014
$37,587
9%
$2,504,110
-4%
2012
$34,497
—
$2,619,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Houlihan Lawrence, Deb Hidy

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27 Hillsley Road, Darien, CT 06820 (MLS# 24175837) is a Single Family property with 6 bedrooms, 4 full bathrooms and 2 partial bathrooms. 27 Hillsley Road is currently listed for $5,450,000 and was received on May 15, 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.

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