27 Hillsley Road

Closed 6/25/26
Closed 6/25/26
Gallery Image 1
Sold
Last Sold Price
$5,200,000
6 beds7,670 sqft$678/sqft
27 Hillsley Rd, Darien, CT 06820
Single FamilyProperty Type
2 acresLot Size
2000Year Built
$678/sq ftPrice per sq ft
3 carsParking Spaces

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,...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.
  • Listed by: Deb Hidy 203.655.8238 dhidy@houlihanlawrence.com • Houlihan Lawrence
Listing closed: 06/25/2026 12:00 AM • Source: SMARTMLS, MLS#: 24175837
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Location

Listing Courtesy of Houlihan Lawrence, Deb Hidy

Sold By Compass Connecticut, LLC, Katharine Bunoski

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$29,899 per month

30 year fixed, 6.55% Interest

Principal and Interest

$26,431

Property Taxes

$3,468

HOA Dues

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Property Information for 27 Hillsley Road

Property Details
  • Taxes: $41,620 / year
  • MLS Type: Residential
  • County: Fairfield County
  • Basement Description: Full, Fully Finished
  • Direct Waterfront: No
  • Garages Number: 3
  • Style: Colonial
  • Garage Parking Info: Attached Garage
  • Swimming Pool: No
Building Information
  • Year Built: 2000
  • Lot Size: 2.00 AC / 87,120 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Brookside to Hillsley Road
  • Elementary School: Ox Ridge
  • High School: Darien
  • Latitude: 41.113889
  • Longitude: -73.479329
  • Middle Jr High School: Middlesex
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $41,620
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Beach Rights
Interior Features
  • Appliances Included: Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Walk-up
  • Cooling System: Central Air
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Security System
  • Laundry Room Info: Upper Level
  • Rooms Additional: Foyer, Laundry Room, Mud Room
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 28.0
Room 2
  • Room Entry Order: 10
  • Room Length: 18.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Room 3
  • Room Entry Order: 11
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 13.0
Room 4
  • Room Entry Order: 12
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Office
  • Room Width: 13.0
Room 5
  • Listing Key: 51D10799462D5BEAE0631A01100A76FB
  • Room Entry Order: 13
  • Room Length: 21.0
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 50.0
Room 6
  • Room Entry Order: 2
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 15.0
Room 7
  • Room Entry Order: 3
  • Room Length: 36.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 18.0
Room 8
  • Room Entry Order: 4
  • Room Features: Fireplace
  • Room Length: 22.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 20.0
Room 9
  • Listing Key: 51D10799462D5BEAE0631A01100A76FB
  • Room Entry Order: 5
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Sun Room
  • Room Width: 13.0
Room 10
  • Room Entry Order: 6
  • Room Features: Fireplace
  • Room Length: 21.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 28.0
Room 11
  • Room Entry Order: 7
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 17.0
Room 12
  • Room Entry Order: 8
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 13
  • Room Entry Order: 9
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Wood
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2000
  • Year Built Source: Owner
  • Bank Owned Property: No
  • Sq Ft Est Heated Below Grade: 1050
  • Living Area SQFT Per Public Records: 6620
Lot Information
  • Lot Description: Level Lot, On Cul-De-Sac, Professionally Landscaped
  • Parcel Number: 102629
  • Sq Ft Est Heated Above Grade: 6620.0
  • Sq Ft Total: 7670.0
  • Zoning: R2
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, 100 Gallon Tank
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 27 Hillsley Road

DateEvent & SourcePriceAppreciation
Jun 17, 2026

Closed (Public Record)

Public Record #1944521623

$5,200,000

+11.2% / yr

Oct 8, 2020

Closed (Public Record)

Public Record #682387834

$2,845,000—
Oct 8, 2020

Closed (Public Record)

Public Record #1419560847

$2,845,000—
DateEvent & SourcePrice
06/17/2026

Closed (Public Record)

Public Record #1944521623

$5,200,000

+11.2% / yr

10/08/2020

Closed (Public Record)

Public Record #682387834

$2,845,000
10/08/2020

Closed (Public Record)

Public Record #1419560847

$2,845,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 27 Hillsley Road

Taxable ValueLand$806,400Additions$1,882,230Total$2,688,630
Tax Record2025$41,620 ($3,468 / month)
Home Facts
Beds4Baths4Total Finished SqFt6,620 SqFtAbove Grade Finished SqFt6,620 SqFtUnfinished Basement SqFt164 SqFtStories2Lot Size87,120 SqFtStyleSingle Family ResidenceYear Built1999Year Renovated1999ZoningR2CountyWESTERN CONNECTICUTAPNDARI M:01 B:52

Schools near 27 Hillsley Road

This home is within Darien School District.
Rating
School
Type
Grades
Distance
Ox Ridge Elementary School
Public - PK to 5
Middlesex Middle School
Public - 6 to 8
Darien High School
Public - 9 to 12
Rating
School
Distance
Ox Ridge Elementary School
PublicPK to 5

Middlesex Middle School
Public6 to 8

Darien High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Darien
Darien
A coastal Connecticut town with a strong sense of community. Incorporated in 1820, Darien is a popular coastal town situated between Stamford and Norwalk. Just a 1 hour train ride from Manhattan via Metro North, Darien is an ideal commuter town that boasts spectacular shoreline activities...
Darien Guide

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 27 Hillsley Road, Darien, CT 06820
$5,200,000
6
7,670
87,120
49 Charter Oak Lane, New Canaan, CT 06840
$2,665,000
6
7,834
72,309
32 Hillsley Road, Darien, CT 06820
$1,200,000
4
3,712
74,487
35 Hillsley Road, Darien, CT 06820
$2,665,000
6
7,834
71,874
34 Hillsley Road, Darien, CT 06820
$1,825,000
4
4.5
5,288
73,616
10 Hillsley Road, Darien, CT 06820
$4,200,000
5
6,373
87,555

Explore Nearby Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Houlihan Lawrence, Deb Hidy

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.