770 Old Academy+1386 Hillside Rd, Fairfield, CT 06824

Off Market Sep 2020 for $2.8M

$3,903,269

Est. refi paymentEst. refi $3,898/mo

•

6,949

sq ft

770 Old Academy+1386 Hillside Rd, Fairfield, CT 06824

About this home

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.

The assessment (2,462,600) and tax amount ( $65,973. ) is the combined amount of both properties of 1386 Hillside Road (assessment 1913030 tax 51,250) and 770 Old Academy Rd (assessment 549,570 tax 14,723) being bought listed together.

Single-familyProperty Type

1900Year Built

5.78 acresLot Size

$562Est. Price/Sq.Ft.

2 car garageParking

Listed by Linda Blackwell • Houlihan Lawrence

Bought with Sue Wittekind • William Raveis Real Estate

Source:Smart MLS #170292185

Redfin Estimate

$3,903,269

$1.1M since sold in September 2020$162K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.6% lower than the average sale price ($4.09M) of 6 comparable homes.

SOLD AUG 5, 2026
$2,995,000
A
5 beds5.5 baths5,789 sq ft
221 Greens Farms Rd, Westport, CT 06880
SOLD NOV 20, 2025
$2,865,000
B
6 beds4.5 baths6,856 sq ft
5 Northside Ln, Westport, CT 06880
SOLD AUG 7, 2026
$5,700,000
C
6 beds6 baths8,717 sq ft
6 Twin Circle Dr, Westport, CT 06880
SOLD JUL 15, 2026
$3,895,000
D
5 beds5.5 baths7,964 sq ft
17 Vineyard Ln, Westport, CT 06880
SOLD AUG 6, 2026
$2,550,000
E
5 beds4.5 baths4,179 sq ft
114 Cross Hwy, Westport, CT 06880
SOLD AUG 20, 2026
$6,550,000
F
5 beds4.5 baths4,875 sq ft
6 Gray Ln, Westport, CT 06880

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Earn from this home

Sell

$1,697,137

Est. take-home

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Refinance

Est. cash available

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Market trends in 06824, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

105.9%

0.7% MoM

Median sale price

$1.3M

$16K MoM

Avg. days on market

28d

0 days MoM

Recently sold homes

140

24 MoM

New listings for sale

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COMING SOON
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5 beds3.5 baths2,866 sq ft
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OPEN SAT, 12PM TO 3PM
$1,499,000
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OPEN SAT, 12PM TO 1PM
$2,299,000
4 beds3.5 baths2,706 sq ft
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OPEN SAT, 1PM TO 4PM
$2,395,000
4 beds5 baths4,630 sq ft
128 Cobblers Hill Rd, Fairfield, CT 06824
OPEN SAT, 11AM TO 2PM
$750,000
3 beds2 baths1,682 sq ft
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NEW 34 HRS AGO
$1,065,750
3 beds3.5 baths2,529 sq ft
79 Thorpe St #79, Fairfield, CT 06824
OPEN SAT, 12PM TO 3PM
$1,399,000
4 beds3 baths3,588 sq ft
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See all

Provided by Redfin

Sale history for 770 Old Academy+1386 Hillside Rd

Date

Event

Price

Public Records

Sep 14, 2020

Sold

$600,000

$86/sq ft

Smart MLS #170292185

Sep 11, 2020

Sold

$2,804,000

$404/sq ft

May 3, 2020

Listed

$2,999,000

$432/sq ft

Smart MLS #170166937

Feb 21, 2020

Listing Removed

—

Feb 25, 2019

Listed

$948,000

$136/sq ft

Smart MLS #170167064

Feb 21, 2020

Listing Removed

—

Feb 25, 2019

Listed

$948,000

$136/sq ft

Smart MLS #170063940

Sep 5, 2018

Listing Removed

—

Mar 21, 2018

Listed

$4,250,000

$612/sq ft

Smart MLS #99172275

Jan 13, 2018

Listing Removed

—

Jan 11, 2017

Listed

$4,250,000

$612/sq ft

Smart MLS #99041312

Oct 1, 2013

Listing Removed

—

Sep 13, 2013

Listed

$1,100,000

$158/sq ft

Public Records

Sep 20, 2005

Sold

$625,000

$90/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$12,479 (+1.0%)

$373,660 + $79,940

$453,600

2022

$12,356 (+1.0%)

$373,660 + $79,940

$453,600

2021

$12,238 (−16.9%)

$373,660 + $79,940

$453,600

2020

$14,723

$453,810 + $95,760

$549,570

2019

$14,723 (+1.6%)

$453,810 + $95,760

$549,570

2018

$14,487 (+2.1%)

$453,810 + $95,760

$549,570

2017

$14,190 (+1.5%)

$453,810 + $95,760

$549,570

2016

$13,987 (−5.3%)

$453,810 + $95,760

$549,570

2014

$14,766

$511,770 + $93,380

$605,150

Tax history for 770 Old Academy+1386 Hillside Rd

Year

Property tax

Land + Additions

Assessment*

2023

$12,479 (+1.0%)

$373,660 + $79,940

$453,600

2022

$12,356 (+1.0%)

$373,660 + $79,940

$453,600

2021

$12,238 (−16.9%)

$373,660 + $79,940

$453,600

2020

$14,723

$453,810 + $95,760

$549,570

2019

$14,723 (+1.6%)

$453,810 + $95,760

$549,570

2018

$14,487 (+2.1%)

$453,810 + $95,760

$549,570

2017

$14,190 (+1.5%)

$453,810 + $95,760

$549,570

2016

$13,987 (−5.3%)

$453,810 + $95,760

$549,570

2014

$14,766

$511,770 + $93,380

$605,150

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

—

Baths

—

Stories

Lot width

—

Lot depth

—

Lot size

2.15 Acres

Year renovated

—

Sq. Ft.

1,242

Year built

1900

Style

Multi-Family (2-4 Unit)

County

Fairfield County

APN

130264

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: 2

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 15
Laundry Room Location: LL & 2nd
Interior Features: Auto Garage Door Opener, Open Floor Plan, Sauna, Security System
Thermostat(s)
Fireplaces Total: 3
Appliances Included: Cook Top, Oven/Range, Wall Oven, Microwave, Refrigerator, Freezer, Icemaker, Dishwasher

Bathroom Information
# of Baths (Full): 7
# of Baths (Half): 1

Bedroom Information
Beds Total: 6

Room Information
Rooms Additional: Breezeway, Foyer, Wine Cellar
Room Count: 12
Basement Description: Full, Partially Finished, Walk-out, Storage
Has Attic
Attic Description: Walk-up, Finished, Heated

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Wood
Exterior Features: Balcony, Barn, French Doors, Guest House, Lighting, Patio, Porch, Terrace, Underground Sprinkler

Lot Information
Lot Description: May be Subdividable, Water View, Corner Lot, Fence - Partial, Fence - Stone, Professionally Landscaped

Pool Information
Swimming Pool
Pool Description: In Ground Pool, Gunite

Building Information
Foundation Type: Concrete, Stone
Construction Description: Stone, Concrete
Color: whitw

Property Information
Waterfront Description: L. I. Sound Frontage, Water Community, Beach Rights, View
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 1242
Driveway Type: Private, Circular, Paved

Financial

Assessments Information
Assessed Value: $549,570

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: Domestic, Natural Gas
Heat Type: Radiator, Steam, Zoned
Heat Fuel Type: Natural Gas
Energy Features: Extra Insulation, Generator

Location

HOA Information
Association Amenities: Golf Course, Health Club, Medical Facilities, Park, Tennis Courts

School Information
Middle Jr High School: Roger Ludlowe
High School: Ffld Ludlowe
Elementary School: Dwight

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Library, Medical Facilities, Park, Public Transportation, Shopping/Mall, Tennis Courts
Directions: Corner of Hillside Road and Old Academy
County: Fairfield

Public facts

Beds: —
Baths: —
Sq. Ft.: 1,242
Stories: 1.0
Lot Size: 2.15 acres
Style: Multi-Family (2-4 Unit)
Year Built: 1900
Year Renovated: —
County: Fairfield County
APN: 130264

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 2

Around this home

Schools

Dwight Elementary School

Public K-5 • Assigned • 0.7mi

10/10

Roger Ludlowe Middle School

Public 6-8 • Assigned • 2.6mi

8/10

Fairfield Ludlowe High School

Public 9-12 • Assigned • 2.5mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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 98° expected this year, 15 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

4/10 Air Factor

5 unhealthy days expected this year, 7 days in 30 years

Provided by First Street

Historical weather

Fairfield, CT • 06824

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.71M – $4.49M

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Home values near 770 Old Academy+1386 Hillside Rd

Data from public records.

Address	Redfin Estimate
819 Old Academy Rd, Fairfield, CT 5 Beds \| 5 Baths \| 5028 Sq. Ft.	$2,561,576
546 Old Academy Rd, Fairfield, CT 6 Beds \| 6 Baths \| 7316 Sq. Ft.	$4,097,672

Address	Redfin Estimate
745 Old Academy Rd, Fairfield, CT 4 Beds \| 5.5 Baths \| 6686 Sq. Ft.	$3,376,508
680 Old Academy Rd, Fairfield, CT 5 Beds \| 7.5 Baths \| 8890 Sq. Ft.	$4,763,554

Address	Redfin Estimate
701 Old Academy Rd, Fairfield, CT 4 Beds \| 3.5 Baths \| 3188 Sq. Ft.	$1,830,374
863 Old Academy Rd, Fairfield, CT 4 Beds \| 4.5 Baths \| 3656 Sq. Ft.	$2,286,948

Property information provided by Smart MLS when last listed in 2020. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06824, CT

Sale history for 770 Old Academy+1386 Hillside Rd

Tax history for 770 Old Academy+1386 Hillside Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06824

Home values near 770 Old Academy+1386 Hillside Rd

More real estate resources