255 Hillside Road, Fairfield, CT 06430
OFF MARKET

$1,210,700

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,540 sqft (on 2.02 acres)

255 Hillside Road, Fairfield, CT 06430

Est. Refi. Payment $7,870/mo*
Refinance Your Home
Currently Off Market - Sold May 1, 1996 for $488,000

Home Value

Trulia Estimate
$1.21M
Since last month
Increased$66K (+5.7%)
Since last year
Increased$84K (+7.4%)
Since last sale
Increased$729K (+149.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value decreased by -3% in the last 10 years
MonthEstimated value
2026
August 2026$1.22M
August 2026$1.21M
July 2026$1.15M
June 2026$1.22M
May 2026$1.12M
April 2026$1.16M
March 2026$1.13M
February 2026$1.21M
January 2026$1.25M
2025

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
82 Hillside Road, Fairfield, CT
0.17
Single-Family Home
$2,150,000
12/09/25
4
2.5
3,008
320 Warner Hill Road, Southport, CT
0.50
Single-Family Home
$2,210,000
06/02/26
5
2.5
3,435
600 Cedar Road, Southport, CT
0.57
Single-Family Home
$990,000
08/25/26
3
1.5
1,812
2444 Bronson Road, Fairfield, CT
0.32
Single-Family Home
$2,125,000
08/18/26
4
3.5
4,099
820 Hillside Road, Fairfield, CT
0.59
Single-Family Home
$2,215,000
06/10/26
3
2.5
3,594
161 Sherwood Drive, Southport, CT
0.47
Single-Family Home
$2,150,000
07/20/26
4
4.5
4,641
254 Sherwood Farm Road, Fairfield, CT
0.41
Single-Family Home
$1,850,000
12/15/25
4
4.5
4,515
127 Field Rock Road, Southport, CT
0.35
Single-Family Home
$2,875,000
06/11/26
5
5
5,924
179 Verna Hill Road, Fairfield, CT
0.66
Single-Family Home
$1,100,000
01/12/26
5
2.5
2,400
1482 Bronson Road, Fairfield, CT
0.54
Single-Family Home
$1,275,000
06/01/26
4
2.5
2,126

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
351 Hillside Road, Fairfield, CT 06824
0.11
$1,592,900
4
3.5
2,844
Off Market
99 Governors Lane, Fairfield, CT 04937
0.12
$1,708,200
4
3.5
3,489
Off Market
326 Hillside Road, Fairfield, CT 06430
0.13
$3,119,300
5
6
7,000
Off Market
376 Hillside Road, Fairfield, CT 06430
0.16
$2,980,900
5
6
6,600
Off Market
625 Hill Farm Road, Fairfield, CT 06824
0.14
$1,125,300
3
2
1,417
Off Market
82 Hillside Road, Fairfield, CT 06824
0.17
$2,150,000
4
2.5
3,008
Recently Sold
82 Hillside Road, Fairfield, CT 06430
0.18
$1,025,300
4
2.5
1,862
Off Market
494 Hill Farm Road, Fairfield, CT 06824
0.21
$2,965,600
5
5
4,150
Off Market
80 Governors Lane, Fairfield, CT 06824
0.26
$4,499,000
6
7
7,801
For Sale
58 North Cedar Road, Fairfield, CT 06430
0.22
$1,440,800
4
3
3,374
Off Market

Local Information

  • Map ViewExplore the area around 255 Hillside Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1995
2.02 acre lot
2,540 sqft
$477/sqft
Attached Garage

About this House

This single-family home is located at 255 Hillside Road, Fairfield, CT. 255 Hillside Road is in Fairfield, CT and in ZIP code 06430. This property has 4 bedrooms, 3 bathrooms and approximately 2,540 sqft of floor space. This property has a lot size of 2.02 acres and was built in 1995.
255 Hillside Road, Fairfield, CT 06430 is a 4 bedroom, 3 bathroom, 2,540 sqft single-family home built in 1995. It last sold for $488,000 on May 1, 1996 (2% below the $499,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,210,700, with a rent estimate of $7,078/month.
Last check for updates: about 5 hours ago
Listed by Debra Kandrak, (203) 581-3926
William Raveis Real Estate, (203) 255-6841
Bought with: Annette Fiorenza, (203) 221-4520, William Raveis Real Estate, (203) 227-4343
Source: Smart MLS, MLS#95035925

Home Details for 255 Hillside Road

Interior Features

Interior Details
Basement: FullNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Other
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2540 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Oven/RangeDishwasher
Heating & Cooling
Heating: OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Oil
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Flooring: Tile, Wood
Levels, Entrance, & Accessibility
Floors: Tile, Wood

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, PorchNo Private Pool
Parking & Garage
No CarportHas a GarageHas an Attached GarageParking: Attached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 2540 Square Feet

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Clapboard
Property Information
Condition: Completed/Never OccupiedParcel Number: 133254

Price & Status

Price
List Price: $499,000
Status Change & Dates
Off Market Date: Tue Mar 19 1996Possession Timing: 30

Active Status

MLS Status: Closed

Location

Direction & Address
City: Fairfield
School Information
Elementary School: DWIGHTJr High / Middle School: TOMHigh School: FHS

Building

Building Area
Building Area: 2540 Square Feet

HOA

No HOA

Lot Information

Lot Area: 2.02 Acres

Miscellaneous

BasementMls Number: 95035925Above Grade Unfinished Area: 2540

Price and Tax history

DateEventPrice
May 1, 1996
Source: Smart MLS #95035925
Sold
$488,000

Market trends in Fairfield

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$957K
$29.79KMoM
Sale-to-List Price
103.7%
0.4%MoM
Price per sq ft
$477
$5MoM
Available listings
162
16MoM

Around this home

What Locals Say about Fairfield

At least 343 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 87 % Say car is needed

  • 85 % Say parking is easy

  • 82 % Say yards are well-kept

  • 79 % Say there's holiday spirit

  • 76 % Say people would walk alone at night

  • 71 % Say kids play outside

  • 66 % Say they plan to stay for at least 5 years

  • 66 % Say it's quiet

  • 64 % Say there's wildlife

  • 61 % Say neighbors are friendly

  • 61 % Say there are sidewalks

  • 59 % Say streets are well-lit

  • 57 % Say it's walkable to restaurants

  • 50 % Say there are community events

  • 48 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • teddyabby
    "It’s safe and pretty and everyone looks out for one another. There is a bunch of cute parks and a nice walkable downtown."
    0
    Flag
  • Bnsdkbr225
    "Friendly and beautiful. Close to Lake Mohegan and parks. Lake rights to Lake Hill’s association . "
    0
    Flag
  • Kevin.cohen318
    "Great place to raise a family, incredibly safe and has all the amenities you could want on a year round basis."
    0
    Flag
  • Alexande.pappas
    "Yes walking miking kids walking to school we have public beaches lake’s plenty of restaurants churches"
    0
    Flag
  • Samuel Rivera
    "Great town for families with kids. Fairfield offers great schools, good supermarkets, tons of restaurants and entertainment "
    0
    Flag
  • Timothy Moss
    "Very family friendly. Great place to live for people of any age. I’ve lived here for 10 years now….."
    0
    Flag
  • Kevin.cohen318
    "5 minutes to either I-95, the Merritt Parkway or metro north, train to NYC is just over an hour each way. Great town that’s close to everything but not too close to anything."
    1
    Flag
  • Trulia User
    "My neighbor is safe and friendly and very clean as well. I've lived in this neighborhood over 18 years and absolutely love it. Thank you "
    3
    Flag
  • Trulia User
    "A very well maintained area . Homes streets ,business ,beaches schools ,library’s ( 3 ) . So much to offer !"
    0
    Flag
  • Sauerh
    "My neighborhood is family-oriented with distinct yet harmonious homes with well- kept yards. We are a short trip from Bridgeport, Norwalk, and Stamford with excellent connections via Metro North and I-95."
    5
    Flag
  • Isabellecj
    "Great neighborhood , good schools, close to town and railway station and beach . Very safe and quiet , properties well maintained and kids friendly . Love my neighborhood!"
    3
    Flag
  • Collin M.
    "Tons of events. Parties. Free concerts etc. there is so much fun things to do and see here. Beaches are amazing!"
    0
    Flag
  • Ab h
    "Walk to absolutely everything from hop on the train to yankee stadium or going to your dentist. Beautiful beaches and parks at your fingertips and children’s activities galore."
    0
    Flag
  • Juan G.
    "Quiet, clean and a good place to raise your kids. The school system it’s awesome and you know your kids are in good hands. "
    1
    Flag
  • Imeiers
    "We have neighbourhood block parties, the best trick or treating in town and a wonderful community spirit. Easily one of the best neighbourhoods in Fairfield. "
    5
    Flag
  • Troy P.
    "I work in Fairfield and it’s a wonderful town. The drive from New Haven is pretty easy with 2 route options either 95 or the merit parkway. "
    0
    Flag
  • Juan G.
    "Best in Connecticut, I have lived here for 6 years and my kids love it. If you want a place to raise your kids this it is the place "
    0
    Flag
  • Sar K.
    "Block parties, neighborhood watch, strong neighbor community, varying ages, active community, holiday celebrations: memorial parade, pancake breakfast, Christmas tree lighting, movies at the beach, music on the green, amazing local restaurants, 4th of July fireworks and much more"
    3
    Flag
  • DE
    "Very safe and relatively diverse. Great schools and decent restaurants. The beach is close by and some good golf courses."
    1
    Flag
  • Raquel.noi
    "Would love it, plenty of space for the dogs to run. Walking trails, beautiful neighborhoods to got for a walk. You will love it here!!"
    0
    Flag
  • Raquel
    "Great place, great community environment! It is such nice to go for walks and feel safe. We love that we found our home here!"
    0
    Flag
  • Raquel
    "Great family environment, lots of parks. Neighbors are friendly and welcoming. A lot of activities for kids. "
    0
    Flag
  • Lisalberts
    "It’s friendly and easy to walk or ride bikes around. The schools are wonderful. A real community feel."
    0
    Flag
  • Alek M.
    "Great town to raise a family, good schools and safe neighborhoods for your kids. Friendly people and clean area all around."
    1
    Flag
  • Fortress.management
    "Excellent schools, great town amenities makes it a great area to raise a family. Commuting to NYC is a little over an hour. Vibrant restaurant scene."
    0
    Flag
  • John S. W. J.
    "A great family oriented town. We love the parks the beaches and the community atmosphere. We couldn’t imagine living anywhere else"
    0
    Flag
  • Blythe A. B.
    "Driving to the train station is easy but parking passes are hard to come by unless you find street parking. waiting list is 18 months. "
    0
    Flag
  • Blythe A. B.
    "Everyone walks their dogs. sidewalks are well maintained. there are plenty of parks as well, both dog parks and free space parks. it is well kept by all dog owners, and it’s expected that you pick up after them!"
    0
    Flag
  • Bellaamore99
    "Close to parks, Wholefoods , Homedepo, shopping and metronorth train. Great neighbores . And feel very safe. "
    5
    Flag
  • Mjcejbart
    "Dog walking Mecca at lake Mohegan. All dogs welcome. Very dog friendly. Nice lake and trails to enjoy with or without a dog. "
    0
    Flag
  • Cheetah4455
    "Christmas walk around in Toilsome Hill. Meet the neighbors and everyone brings a different plate of food"
    1
    Flag
  • al .P
    "Lots of dogs on leaches . Not having your dog on a leach is not a good idea . You know your dog but the other does not know your dog "
    1
    Flag
  • Nour Y.
    "One dog can annoy a lot of families since homes are close to each other so multiple dogs barking is even worse"
    5
    Flag
  • Bassickrachel
    "I do see dogs frequently. People seem friendly, neighbors are quiet. I love airfield for the commute and small Town atmosphere."
    1
    Flag
  • Bassickrachel
    "Excellent I am 5 minutes from I-95 and Fairfield Metro Train Station. It is close to grocery stores and it is quite with friendly people."
    0
    Flag
  • Dennis
    "Many dogs that are very pleasant. Owners stop and chat while dogs play. Great way to meet your neighbors."
    0
    Flag
  • Larry
    "Moved here from Dallas and absolutely love it. I commute to downtown New Haven by car and it’s about 30-35 minutes."
    0
    Flag
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 255 Hillside Road

  • What is 255 Hillside Road estimated to be worth?
    Trulia's estimated value for 255 Hillside Road in Fairfield, CT is $1,210,700.
  • What is the price history for 255 Hillside Road?
    255 Hillside Road in Fairfield, CT last sold for $488,000 in May 1996.
  • Is Fairfield a buyer's or seller's market?
    Fairfield is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Fairfield?
    The median sale price in Fairfield is $957K. That is down $29.79K from the prior month.
  • Does 255 Hillside Road have air conditioning?
    Yes, 255 Hillside Road in Fairfield, CT has air conditioning.
  • How big is the lot at 255 Hillside Road?
    The lot at 255 Hillside Road in Fairfield, CT is about 2 acres.

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