Sold
Last Sold Price
6 beds6,949 sqft$404/sqft
1386 Hillside Rd, Fairfield, CT 06824
Single FamilyProperty Type
5.78 acresLot Size
1900Year Built
$404/sq ftPrice per sq ft
2 carsParking Spaces

Description

Perfect as a primary home or a private retreat. Located in the heart of Greenfield Hill with clear views of Long Island Sound this 6 acre estate is the perfect safe haven. It boasts plenty of space for living, working, schooling and relaxing. Easy interior and exterior entertaining flow. Enjoy the pool, terraces, gardens, lawns, and incredible party barn. Six bedroom main house has: High ceilings, wide plank floors, open spacious rooms, private office, yoga nook, sauna, multi entertaining spaces....Perfect as a primary home or a private retreat. Located in the heart of Greenfield Hill with clear views of Long Island Sound this 6 acre estate is the perfect safe haven. It boasts plenty of space for living, working, schooling and relaxing. Easy interior and exterior entertaining flow. Enjoy the pool, terraces, gardens, lawns, and incredible party barn. Six bedroom main house has: High ceilings, wide plank floors, open spacious rooms, private office, yoga nook, sauna, multi entertaining spaces. Abundant windows and french doors give natural light and panoramic views. The separate two bedroom guest house was completely renovated with gas fireplace, laundry and 2 bay garage and private stone terrace. Perfect for multi-generational living (private space for parents or grown kids),property manager, guests or income potential (rental opportunity) Third building is 2000 sq ft fully renovated stable with chef’s kitchen, full bath and open floor plan and terraces. Peaceful and private. This estate is made up of two adjoining properties landscaped and offered as one compound. This home has always been the place that friends and family gather for any reason they can! It's been completely updated and renovated to enhance the authentic legacy details while infusing every inch with bright fresh energy. The result is enchanting. Plenty of space to live your dreams and create your own private sanctuary. 8 Minutes to town and beaches. Easy commute -70 min to NYC or 30 minutes to Stamford.
  • Listed by: Linda Blackwell 203.362.8316 lindablackwell@optonline.net • Houlihan Lawrence
Listing closed: 09/11/2020 12:00 AM • Source: SMARTMLS, MLS#: 170292185

Recent comparable sales

Median sold price

$3,000,000

Avg days on market

62

Sale-to-list ratio

95.2%

Fairfield, CT

9 comparable properties found

$3,292,000 | 99 Old Academy Road, Fairfield, CT 06824
1

$3,292,000

Sold 12/15/25

6
Bedrooms
7,062
Square Feet
2.17
Acres
$2,850,000 | 750 Burr Street, Fairfield, CT 06824
2

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Sold 08/03/26

6
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6,214
Square Feet
2.63
Acres
an aerial view of a house
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Sold 12/09/25

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2
Acres
$3,875,000 | 971 Hulls Farm Road, Fairfield, CT 06890
4

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Sold 08/29/25

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7,300
Square Feet
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Acres
$3,000,000 | 111 Golden Pond Lane, Fairfield, CT 06824
5

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Sold 08/27/26

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$3,800,000 | 1084 Sturges Highway, Fairfield, CT 06880
6

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6,897
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2.32
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Sold 03/14/25

6
Bedrooms
7
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10,787
Square Feet
3.18
Acres
$2,350,000 | 2775 North Street, Fairfield, CT 06824
1/47
8

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Sold 01/15/26

5
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5,978
Square Feet
2.21
Acres
$2,750,000 | 342 Midlock Road, Fairfield, CT 06824
9

$2,750,000

Sold 07/31/26

5
Bedrooms
7,269
Square Feet
2.03
Acres

Location

Listing Courtesy of Houlihan Lawrence, Linda Blackwell

Sold By William Raveis Real Estate, Sue E Wittekind

Add your commute

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Payment Calculator

$15,479 per month

30 year fixed, 6.55% Interest

Principal and Interest

$14,252

Property Taxes

$1,227

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 1386 Hillside Road

Property Details
  • Taxes: $14,723 / year
  • MLS Type: Residential
  • Basement Description: Full, Partially Finished, Walk-out, Storage
  • Direct Waterfront: No
  • Garages Number: 2
  • Neighborhood: Greenfield Hill
  • Style: Colonial
  • Garage Parking Info: Attached Garage
  • Swimming Pool: Yes
Building Information
  • Year Built: 1900
  • Lot Size: 5.78 AC / 251,776 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Association Amenities: Golf Course, Health Club, Medical Facilities, Park, Tennis Courts
  • Directions: Corner of Hillside Road and Old Academy
  • Elementary School: Dwight
  • Flood Zone: No
  • High School: Ffld Ludlowe
  • Latitude: 41.17795
  • Longitude: -73.29037
  • Middle Jr High School: Roger Ludlowe
  • Neighborhood Amenities: Golf Course, Health Club, Library, Medical Facilities, Park, Public Transportation, Shopping/Mall, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Special Association Assessment: No
  • Tax Year: July 2020-June 2021
  • Property Tax: $14,723
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Barn, French Doors, Guest House, Lighting, Patio, Porch, Terrace, Underground Sprinkler
  • Pool Description: In Ground Pool, Gunite
  • Waterfront Description: L. I. Sound Frontage, Water Community, Beach Rights, View
Interior Features
  • Appliances Included: Cook Top, Oven/Range, Wall Oven, Microwave, Refrigerator, Freezer, Icemaker, Dishwasher
  • Attic Description: Walk-up, Finished, Heated
  • Cooling System: None
  • Heat Type: Radiator, Steam, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Home Automation: Thermostat(s)
  • Interior Features: Auto Garage Door Opener, Open Floor Plan, Sauna, Security System
  • Laundry Room Location: LL & 2nd
  • Rooms Additional: Breezeway, Foyer, Wine Cellar
  • Room Count: 12
  • Rooms Total: 15
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Fireplace,French Doors,Hardwood Floor
  • Room Level: Main
  • Room Type: Formal Dining Room
Room 2
  • Room Entry Order: 10
  • Room Features: Full Bath,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 11
  • Room Features: Beams,Full Bath,Hardwood Floor,Palladian Window(s)
  • Room Level: Upper
  • Room Type: Bedroom
Room 4
  • Room Entry Order: 12
  • Room Features: Built-Ins,On 3rd Floor,Vaulted Ceiling
  • Room Level: Upper
  • Room Type: Rec/Play Room
Room 5
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Built-Ins,Fireplace,French Doors,Wide Board Floor
  • Room Level: Main
  • Room Type: Living Room
Room 6
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Breakfast Nook,Fireplace,Wide Board Floor
  • Room Type: Eat-In Kitchen
Room 7
  • Room Entry Order: 4
  • Room Features: 9 ft+ Ceilings,Built-Ins,French Doors,Wide Board Floor
  • Room Level: Main
  • Room Type: Family Room
Room 8
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,French Doors
  • Room Level: Main
  • Room Type: Office
Room 9
  • Room Entry Order: 6
  • Room Features: Dressing Room,Full Bath,Hardwood Floor,Marble Floor,Stall Shower
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 10
  • Room Entry Order: 7
  • Room Features: Balcony/Deck,Full Bath,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 11
  • Room Entry Order: 8
  • Room Features: Full Bath,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 12
  • Room Entry Order: 9
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: whitw
  • Construction Description: Stone, Concrete
  • Driveway Type: Private, Circular, Paved
  • Exterior Siding: Wood
  • Foundation Type: Concrete, Stone
  • Fuel Tank Location: Non Applicable
  • Gross SQFT Per Public Records: 3550
  • New Construction Type: No/Resale
  • Roof: Wood Shingle
  • Year Built: 1900
  • Year Built Source: Owner
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 1242
Lot Information
  • Lot Description: May be Subdividable, Water View, Corner Lot, Fence - Partial, Fence - Stone, Professionally Landscaped
  • Parcel Number: 130264
  • Sq Ft Est Heated Above Grade: 6949.0
  • Sq Ft Total: 6949.0
  • Zoning: AAA
Utilities
  • Energy Features: Extra Insulation, Generator
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Domestic, Natural Gas
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 1386 Hillside Road

DateEvent & SourcePriceAppreciation
Sep 9, 2020

Closed (Public Record)

Public Record #1409841004

$2,100,000
Sep 9, 2020

Closed (Public Record)

Public Record #678497924

$2,100,000

+188.0% / yr

Dec 6, 2006

Closed (Public Record)

Public Record #327036604

$1
DateEvent & SourcePrice
09/09/2020

Closed (Public Record)

Public Record #1409841004

$2,100,000
09/09/2020

Closed (Public Record)

Public Record #678497924

$2,100,000

+188.0% / yr

12/06/2006

Closed (Public Record)

Public Record #327036604

$1

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

Public Records for 1386 Hillside Road

Taxable ValueLand$433,440Additions$1,125,460Total$1,558,900
Tax Record2025$44,257 ($3,688 / month)
Home Facts
Beds0Lot Size158,123 SqFtStyleSingle Family ResidenceZoningAAACountyGREATER BRIDGEPORTAPNFFLD M:173 B:73

Schools near 1386 Hillside Road

This home is within Fairfield School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Private - K to 9
Rating
School
Distance
Dwight Elementary School
PublicK to 5

Roger Ludlowe Middle School
Public6 to 8

Fairfield Ludlowe High School
Public9 to 12

Fairfield Country Day School
PrivateK to 9

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.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 1386 Hillside Road, Fairfield, CT 06824
$2,804,000
6
6,949
251,776
$2,350,000
6
5,726
78,408
$3,275,000
5
9,246
108,464
$3,625,000
6
7,952
129,808
$600,000
2
1,242
93,654
$2,950,000
7
7,734
66,646

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, Linda Blackwell

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.