Off Market Mar 2025 for $1.6M

$2,293,163

Est. refi paymentEst. refi $4,891/mo

•

3,918

sq ft

255 Hillside Rd, Fairfield, CT 06824

About this home

HIGHEST AND BEST DUE MONDAY 2/24 AT NOON...Lower Greenfield Hill at its best. This is a beautifully restyled colonial on a private and fully fenced 2+ acre lot. Spacious open floor-plan perfect for today's modern lifestyle. The focal point of the home is the chef's eat-in kitchen with Quartz center island and all new stainless steel appliances which flows seamlessly to the dining room and huge family room with stone fireplace and vaulted ceiling. Doors lead directly to the newly finished terrace and heated pool with safety fence, perfect for entertaining. Gracious front to back formal living room with french doors leading to the wrap around porch. Mudroom and remodeled powder room complete this level. Upstairs, enjoy privacy in the huge primary bedroom suite with 2 walk in closets, gorgeous renovated bath and sitting room. Ensuite guest room and two additional bedrooms that share the hall bath complete this level. Fabulous walk-out finished lower level makes the perfect playroom. Attached 2-car Garage and tremendous storage. Updates include a new roof, new tankless hot water heater, electric blinds, full house generator, pool updated including new pool heater and light feature. Amazing location - walk to Greenfield Hill's favorites - The Corner Market & Sandwich Shop, BE Chocolat or Bonda Restaurant. Exceptional privacy and convenient to town, this property is absolutely spectacular!

Single-familyProperty Type

1995Year Built

2.41 acresLot Size

$585Est. Price/Sq.Ft.

2 car garageParking

Listed by Cindy Raney • Coldwell Banker Realty

Contact: Agent Attribution Contact: (203) 257-8320

Bought with Pam Toner • Berkshire Hathaway NE Prop.

Source:Smart MLS #24074345

Redfin Estimate

$2,293,163

$668K since sold in March 2025$179K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 7.7% higher than the average sale price ($2.13M) of 6 comparable homes.

SOLD JUL 31, 2026
$2,495,000
A
4 beds4 baths4,300 sq ft
3050 Bronson Rd, Fairfield, CT 06824
SOLD AUG 18, 2026
$2,125,000
B
4 beds3.5 baths4,099 sq ft
2444 Bronson Rd, Fairfield, CT 06824
SOLD JUL 20, 2026
$2,150,000
C
4 beds4.5 baths4,641 sq ft
161 Sherwood Dr, Southport, CT 06890
SOLD DEC 15, 2025
$1,850,000
D
4 beds4.5 baths4,515 sq ft
254 Sherwood Farm Rd, Fairfield, CT 06824
SOLD JUL 1, 2026
$1,750,000
E
4 beds2.5 baths2,642 sq ft
264 Half Mile Rd, Southport, CT 06890
SOLD MAY 15, 2026
$2,400,000
F
4 beds3 baths3,703 sq ft
260 Range Rd, Southport, CT 06890

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Earn from this home

Sell

$892,451

Est. take-home

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Refinance

Est. cash available

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Rent

$10,240/mo

Redfin rental estimate

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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

105.4%

0.1% MoM

Median sale price

$1.3M

$13K MoM

Avg. days on market

30d

2 days MoM

Recently sold homes

16 MoM

New listings for sale

COMING SOON
$1,225,000
3 beds2.5 baths2,447 sq ft
130 Elm St, Fairfield, CT 06824
$1,299,000
3 beds2 baths1,297 sq ft
877 S Pine Creek Rd, Fairfield, CT 06824
OPEN THU, 11AM TO 2PM
$1,799,000
5 beds3.5 baths2,732 sq ft
239 Beach Rd, Fairfield, CT 06824
$899,000
2 beds1 bath1,104 sq ft
73 Alden St, Fairfield, CT 06824
$1,800,000
5 beds3.5 baths4,845 sq ft
220 Stonewall Ln, Fairfield, CT 06824
$359,000
2 beds1 bath900 sq ft
245 Sunnyridge Ave #50, Fairfield, CT 06824
VIDEO TOUR
$4,500,000
5 beds4 baths4,142 sq ft
1149 Fairfield Beach Rd, Fairfield, CT 06824
$1,900,000
5 beds5.5 baths4,180 sq ft
1964 N Benson Rd, Fairfield, CT 06824
See all

Provided by Redfin

Sale history for 255 Hillside Rd

Date

Event

Price

Smart MLS #24074345

Mar 25, 2025

Sold

$1,625,000

$415/sq ft

Mar 17, 2025

Pending

—

Feb 27, 2025

Contingent

—

Feb 20, 2025

Listed

$1,599,000

$408/sq ft

Feb 18, 2025

Coming Soon

$1,599,000

$408/sq ft

Smart MLS #170196027

Sep 11, 2019

Sold

$930,000

$237/sq ft

Jul 30, 2019

Listing Removed

—

Jun 15, 2019

Contingent

—

May 16, 2019

Listed

$975,000

$249/sq ft

Perfect combination of location and setting - close to town with a country feel! This beautifully remodeled lower Greenfield Hill 4 - 5 Bedroom/3.5 Bath Colonial offers the best of all worlds. The wrap around front porch is the perfect place to sip coffee or read a book. The private backyard is a quiet oasis with fenced in pool and deck for entertaining. Gorgeous new Kitchen features large island with seating and Quartzite countertops and opens to Dining Room and Family Room with stone fireplace and vaulted ceiling. Gracious front to back Living Room with French Doors leading to the Porch. 2 en-suite Master Bedroom/Bath options plus 3 additional Bedrooms and Hall Bath with double vanity and tub/shower. Walk-out, finished Lower Level adds an additional 550 Square Feet plus a large unfinished area. Attached 2-car Garage and tremendous storage. Walk to Testo's Market for lunch or Bonda for dinner. Incredible low maintenance home and location - move in just in time to start enjoying the pool!

Smart MLS #170189881

May 16, 2019

Listing Removed

—

May 1, 2019

Listed

$989,000

$252/sq ft

Smart MLS #99180937

Jun 20, 2017

Sold

$850,000

$217/sq ft

May 31, 2017

Listing Removed

—

Apr 9, 2017

Listed

$849,900

$217/sq ft

Smart MLS #99151083

Oct 21, 2016

Listing Removed

—

Jun 22, 2016

Listed

$925,000

$236/sq ft

Smart MLS #99135359

Jun 22, 2016

Listing Removed

—

Mar 2, 2016

Listed

$925,000

$236/sq ft

Smart MLS #99108727

Dec 6, 2015

Listing Removed

—

Jul 15, 2015

Listed

$960,000

$245/sq ft

Public Records

May 1, 1996

Sold

$488,000

$125/sq ft

Smart MLS #95035925

Dec 18, 1995

Listed

$499,000

$127/sq ft

Smart MLS #95013112

Dec 22, 1995

Listing Removed

—

May 5, 1995

Listed

$549,000

$140/sq ft

Smart MLS #94029316

May 15, 1995

Listing Removed

—

Oct 14, 1994

Listed

$499,000

$127/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$18,132 (+1.0%)

$302,330 + $356,790

$659,120

2022

$17,954 (+1.0%)

$302,330 + $356,790

$659,120

2021

$17,783 (+1.5%)

$302,330 + $356,790

$659,120

2020

$17,512

$323,050 + $330,610

$653,660

2019

$17,512 (+1.6%)

$323,050 + $330,610

$653,660

2018

$17,230 (+2.1%)

$323,050 + $330,610

$653,660

2017

$16,878 (+1.5%)

$323,050 + $330,610

$653,660

2016

$16,636 (−18.4%)

$323,050 + $330,610

$653,660

2014

$20,390

$489,930 + $345,730

$835,660

Tax history for 255 Hillside Rd

Year

Property tax

Land + Additions

Assessment*

2023

$18,132 (+1.0%)

$302,330 + $356,790

$659,120

2022

$17,954 (+1.0%)

$302,330 + $356,790

$659,120

2021

$17,783 (+1.5%)

$302,330 + $356,790

$659,120

2020

$17,512

$323,050 + $330,610

$653,660

2019

$17,512 (+1.6%)

$323,050 + $330,610

$653,660

2018

$17,230 (+2.1%)

$323,050 + $330,610

$653,660

2017

$16,878 (+1.5%)

$323,050 + $330,610

$653,660

2016

$16,636 (−18.4%)

$323,050 + $330,610

$653,660

2014

$20,390

$489,930 + $345,730

$835,660

*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

3.5

Stories

Lot width

—

Lot depth

—

Lot size

2.41 Acres

Year renovated

—

Sq. Ft.

2,998

Year built

1995

Style

Single Family Residential

County

Fairfield County

APN

133254

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

Interior Information
Total Rooms: 8
Laundry Room Info: Upper Level
Interior Features: Auto Garage Door Opener, Open Floor Plan, Security System
In-Law Apartment: No
Fireplaces Total: 1
Cooling System: Central Air
Appliances Included: Gas Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 3
# of Baths (Half): 1

Bedroom Information
Beds Total: 4

Room Information
Rooms Additional: Foyer, Mud Room
Basement Description: Full, Heated, Fully Finished, Cooled, Walk-out, Liveable Space, Full With Walk-Out
Has Attic
Attic Description: Storage Space, Pull-Down Stairs

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Wood
Exterior Features: Porch-Wrap Around, Porch, Lighting, French Doors, Patio

Lot Information
Lot Description: Fence - Full, Treed, Level Lot, Sloping Lot

Land Information
Encumbrances Restrictions: Easements, Inland-Wetland Restrictions

Pool Information
Swimming Pool
Pool Description: Heated, Safety Fence, Vinyl, In Ground Pool

Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: White

Property Information
Waterfront Description: Beach Rights, Water Community
Radon Mitigation Air
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2998

Financial

Assessments Information
Assessed Value: $659,120

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: Tankless Hotwater
Heat Type: Hot Air
Heat Fuel Type: Natural Gas
Energy Features: Generator

Location

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

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Library, Medical Facilities, Park, Shopping/Mall
Directions: Congress Street to Hillside
County: Fairfield

Public facts

Beds: 4
Baths: 3.5
Sq. Ft.: 2,998
Stories: 2.0
Lot Size: 2.41 acres
Style: Single Family Residential
Year Built: 1995
Year Renovated: —
County: Fairfield County
APN: 133254

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 6

Around this home

Schools

Dwight Elementary School

Public K-5 • Assigned • 1.6mi

10/10

Roger Ludlowe Middle School

Public 6-8 • Assigned • 1.7mi

8/10

Fairfield Ludlowe High School

Public 9-12 • Assigned • 1.5mi

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

6/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

67% 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

$2.18M – $2.64M

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Nearby similar homes

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7 beds8.5 baths9,129 sq ft

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NEW CONSTRUCTION

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VIDEO TOUR

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NEW CONSTRUCTION

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New listings for sale in 06824

COMING SOON

$1,225,000

3 beds2.5 baths2,447 sq ft

130 Elm St, Fairfield, CT 06824

$1,299,000

3 beds2 baths1,297 sq ft

877 S Pine Creek Rd, Fairfield, CT 06824

OPEN THU, 11AM TO 2PM

$1,799,000

5 beds3.5 baths2,732 sq ft

239 Beach Rd, Fairfield, CT 06824

$899,000

2 beds1 bath1,104 sq ft

73 Alden St, Fairfield, CT 06824

$1,800,000

5 beds3.5 baths4,845 sq ft

220 Stonewall Ln, Fairfield, CT 06824

$359,000

2 beds1 bath900 sq ft

245 Sunnyridge Ave #50, Fairfield, CT 06824

VIDEO TOUR

$4,500,000

5 beds4 baths4,142 sq ft

1149 Fairfield Beach Rd, Fairfield, CT 06824

$1,900,000

5 beds5.5 baths4,180 sq ft

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Home values near 255 Hillside Rd

Data from public records.

Address	Redfin Estimate
279 Hillside Road, Fairfield, CT 3 Beds \| 1.5 Baths \| 1833 Sq. Ft.	$1,215,063
150 Hillside Road, Fairfield, CT 3 Beds \| 2.5 Baths \| 2078 Sq. Ft.	$1,278,504

Address	Redfin Estimate
326 Hillside Road, Fairfield, CT 5 Beds \| 7.5 Baths \| 6695 Sq. Ft.	$4,511,850
280 Hillside Road, Fairfield, CT 4 Beds \| 3.5 Baths \| 2740 Sq. Ft.	$1,584,848

Address	Redfin Estimate
351 Hillside Road, Fairfield, CT 4 Beds \| 3.5 Baths \| 2844 Sq. Ft.	$1,902,400
2040 Bronson Road, Fairfield, CT 4 Beds \| 3.5 Baths \| 2973 Sq. Ft.	$1,380,347

Property information provided by Smart MLS when last listed in 2025. 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 255 Hillside Rd

Tax history for 255 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 255 Hillside Rd

More real estate resources