255 Hillside Road, Fairfield, CT 06824
OFF MARKET

$1,767,200

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,918 sqft (on 2.41 acres)

255 Hillside Road, Fairfield, CT 06824

Refinance Your Home
Currently Off Market - Sold Mar 25, 2025 for $1,625,000

Home Value

Trulia Estimate
$1.77M
Since last month
Increased$24K (+1.4%)
Since last year
Increased$114K (+6.9%)
Since last sale
Increased$141K (+8.7%)
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 increased by +100% in the last 10 years
MonthEstimated value
2026
August 2026$1.77M
August 2026$1.77M
July 2026$1.74M
June 2026$1.73M
May 2026$1.72M
April 2026$1.69M
March 2026$1.69M
February 2026$1.69M
January 2026$1.66M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
0.20
Single-Family Home
$2,150,000
12/09/25
4
2.5
3,008
2444 Bronson Road, Fairfield, CT
0.30
Single-Family Home
$2,125,000
08/18/26
4
3.5
4,099
254 Sherwood Farm Road, Fairfield, CT
0.42
Single-Family Home
$1,850,000
12/15/25
4
4.5
4,515
161 Sherwood Drive, Southport, CT
0.48
Single-Family Home
$2,150,000
07/20/26
4
4.5
4,641
320 Warner Hill Road, Southport, CT
0.52
Single-Family Home
$2,210,000
06/02/26
5
2.5
3,435
820 Hillside Road, Fairfield, CT
0.57
Single-Family Home
$2,215,000
06/10/26
3
2.5
3,594
127 Field Rock Road, Southport, CT
0.38
Single-Family Home
$2,875,000
06/11/26
5
5
5,924
3050 Bronson Road, Fairfield, CT
0.77
Single-Family Home
$2,495,000
07/31/26
4
4
4,300
2683 Bronson Road, Fairfield, CT
0.49
Single-Family Home
$3,100,000
05/28/26
5
6
5,515

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
0.10
$1,592,900
4
3.5
2,844
Off Market
99 Governors Lane, Fairfield, CT 04937
0.10
$1,708,200
4
3.5
3,489
Off Market
326 Hillside Road, Fairfield, CT 06430
0.12
$3,119,300
5
6
7,000
Off Market
376 Hillside Road, Fairfield, CT 06430
0.14
$2,980,900
5
6
6,600
Off Market
625 Hill Farm Road, Fairfield, CT 06824
0.15
$1,125,300
3
2
1,417
Off Market
82 Hillside Road, Fairfield, CT 06824
0.20
$2,150,000
4
2.5
3,008
Recently Sold
82 Hillside Road, Fairfield, CT 06430
0.20
$1,025,300
4
2.5
1,862
Off Market
494 Hill Farm Road, Fairfield, CT 06824
0.22
$2,965,600
5
5
4,150
Off Market
80 Governors Lane, Fairfield, CT 06824
0.24
$4,499,000
6
7
7,801
For Sale
58 North Cedar Road, Fairfield, CT 06430
0.24
$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
2.41 acre lot
3,918 sqft
$451/sqft
2 Car Garage

About this House

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!
255 Hillside Road, Fairfield, CT 06824 is a 4 bedroom, 4 bathroom, 3,918 sqft single-family home built in 1995. It last sold for $1,625,000 on Mar 25, 2025 (2% above the $1,599,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,767,200.
Last check for updates: about 15 hours ago
Listed by Cindy Raney, (203) 257-8320
Coldwell Banker Realty, (203) 227-8424
Bought with: Pam Toner, (917) 319-1580, Berkshire Hathaway NE Prop., (203) 227-5117
Source: Smart MLS, MLS#24074345

Home Details for 255 Hillside Road

Interior Features

Interior Details
Basement: Full,Heated,Finished,Cooled,Walk-Out Access,Liveable SpaceNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3918 Square Feet
Appliances & Utilities
Appliances: Gas Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Tankless Water HeaterDishwasherDryerLaundry: Upper Level,Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Wrap Around, Porch, PatioFencing: FullExterior: LightingFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached,Garage Door Opener
Pool
Pool: Heated, Fenced, Vinyl, In GroundPool
Frontage
Waterfront: Beach Access, Water CommunityNot on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 2998 Square FeetFinished Area (below surface): 920 Square Feet

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Not Included in Sale: Please see list of Inclusions/ExclusionsParcel Number: 133254

Price & Status

Price
List Price: $1,599,000
Status Change & Dates
Off Market Date: Thu Mar 13 2025Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: FairfieldCommunity: Greenfield Hill
School Information
Elementary School: DwightJr High / Middle School: Roger LudloweHigh School: Fairfield Ludlowe

Building

Building Area
Building Area: 3918 Square Feet

Community

Community Features: Golf, Library, Medical Facilities, Park, Shopping/Mall

HOA

No HOA

Lot Information

Lot Area: 2.41 Acres

Miscellaneous

BasementMls Number: 24074345Attic: Storage, Pull Down StairsAbove Grade Unfinished Area: 2998

Additional Information

GolfLibraryMedical FacilitiesParkShopping/Mall

Price and Tax history

DateEventPrice
Mar 25, 2025
Source: Smart MLS #24074345
Sold
$1,625,000
Mar 17, 2025
Source: Smart MLS #24074345
Pending
$1,599,000
Feb 20, 2025
Source: Smart MLS #24074345
Listed For Sale
$1,599,000
Sep 11, 2019
Source: Smart MLS #170196027
Sold
$930,000
May 16, 2019
Source: Agent Provided
PriceChange
$975,000
Price decreased by 1%

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

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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 $1,767,200.
  • What is the price history for 255 Hillside Road?
    255 Hillside Road in Fairfield, CT last sold for $1,625,000 in March 2025.
  • 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.
  • Does 255 Hillside Road have a pool?
    Yes, 255 Hillside Road in Fairfield, CT has a pool.

Explore by feature - Pet Friendly

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