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.
Est. $7,324 per month, based on comparable rentals
Sale and tax history for 27 Hillsley Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24175837
Jun 25, 2026
Sold
$5,200,000
$678/sq ft
May 27, 2026
Pending
—
May 15, 2026
Listed
$5,450,000
$711/sq ft
Smart MLS #170308569
Oct 16, 2020
Sold
$2,845,000
$371/sq ft
Aug 13, 2020
Contingent
—
Jun 22, 2020
Listed
$2,995,000
$390/sq ft
Gracious center hall colonial on a quiet, private cul-de-sac. Gather with loved ones in the high ceiling, open design kitchen/breakfast/great room overlooking the back lawn and tennis court. Host guests in the deluxe first floor bedroom suite, while you retire to your spacious master suite with gas fireplace, walk in steam shower, spa tub and under counter refrigerator. Short commute to your private office across the hall. The lower level offers space to keep fit in your own gym or unwind with your favorite hobbies. Entertain a crowd in the spacious formal living room and dining room spanning the stunning entrance foyer. Truly a house for building great memories.
Year
Property tax
Land + Additions
Assessment*
2023
$35,991 (+2.2%)
$672,000 + $1,371,790
$2,043,790
2022
$35,215 (+2.3%)
$672,000 + $1,371,790
$2,043,790
2021
$34,417 (+3.1%)
$672,000 + $1,371,790
$2,043,790
2020
$33,375 (−0.8%)
$672,000 + $1,371,790
$2,043,790
2019
$33,661 (−16.4%)
$672,000 + $1,371,790
$2,043,790
2018
$40,266 (−0.5%)
$840,000 + $1,664,110
$2,504,110
2017
$40,466 (+2.5%)
$840,000 + $1,664,110
$2,504,110
2016
$39,490 (+5.1%)
$840,000 + $1,664,110
$2,504,110
2014
$37,587
$840,000 + $1,664,110
$2,504,110
Public record
Beds
4
Baths
4
Stories
2
Lot width
—
Lot depth
—
Lot size
2 Acres
Year renovated
—
Sq. Ft.
6,620
Year built
1999
Style
Single Family Residential
County
Fairfield County
APN
102629
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 13, 2023.
Property details
Parking
Garage Information
Garage & Parking: Attached Garage
Garages Number: 3
Interior
Virtual Tour Information
Interior Information
Total Rooms: 9
Laundry Room Info: Upper Level
Interior Features: Security System
Fireplaces Total: 2
Cooling System: Central Air
Appliances Included: Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
Bathroom Information
# of Baths (Full): 4
# of Baths (Half): 2
Bedroom Information
Beds Total: 6
Room Information
Rooms Additional: Foyer, Laundry Room, Mud Room
Basement Description: Full, Fully Finished
Has Attic
Attic Description: Walk-up
Exterior
Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Wood
Lot Information
Lot Description: Level Lot, On Cul-De-Sac, Professionally Landscaped
Building Information
Foundation Type: Concrete
Construction Description: Frame
Property Information
Waterfront Description: Beach Rights
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 6620
Financial
Assessments Information
Assessed Value: $2,688,630
Utilities
Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Oil, 100 Gallon Tank
Heat Type: Hot Water
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Location
School Information
Middle Jr High School: Middlesex
High School: Darien
Elementary School: Ox Ridge
Location Information
State: Connecticut
Directions: Brookside to Hillsley Road
County: Fairfield
Public facts
Beds: 4
Baths: 4.0
Sq. Ft.: 6,620
Stories: 2.0
Lot Size: 2 acres
Style: Single Family Residential
Year Built: 1999
Year Renovated: —
County: Fairfield County
APN: 102629
Home facts updated by county records on Jul 13, 2023
Other
Documents & Disclosures
Supplement Count Public: 3
Around this home
Schools
Ox Ridge Elementary School
Public PreK-5 • Assigned • 0.8mi
10/10
Middlesex Middle School
Public 6-8 • Assigned • 2.9mi
10/10
Darien High School
Public 9-12 • Assigned • 2.1mi
10/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 99° expected this year, 16 days in 30 years
6/10 Wind Factor
67% chance of strong winds in next 30 years
4/10 Air Factor
4 unhealthy days expected this year, 6 days in 30 years
Provided by First Street
Historical weather
Darien, CT • 06820
Average low and high temperatures (°F)
36
23
38
24
52
35
61
44
69
53
81
63
86
70
81
63
75
60
67
49
55
40
41
28
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
87/ 100
Very good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9 hrs
5.4 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$5.25M – $6.35M
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