255 Hillside Road
Fairfield, CT 06824
- 4 Beds
- 3.5 Baths
- 3,918 sqft (on 2.41 acres)
4 Beds
3.5 Baths
3,918 sqft
(on 2.41 acres)
Local Information
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Description
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!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from March 26, 2025
Home Highlights
Parking
2 Car Garage
Outdoor
Porch, Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 255 Hillside Road
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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 |
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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 |
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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 |
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Price List Price: $1,599,000 |
Status Change & Dates Off Market Date: Thu Mar 13 2025Possession Timing: Immediate |
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MLS Status: Closed |
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Direction & Address City: FairfieldCommunity: Greenfield Hill |
School Information Elementary School: DwightJr High / Middle School: Roger LudloweHigh School: Fairfield Ludlowe |
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Building Area Building Area: 3918 Square Feet |
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Community Features: Golf, Library, Medical Facilities, Park, Shopping/Mall |
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No HOA |
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Lot Area: 2.41 Acres |
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BasementMls Number: 24074345Attic: Storage, Pull Down StairsAbove Grade Unfinished Area: 2998 |
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GolfLibraryMedical FacilitiesParkShopping/Mall |
Last check for updates: about 20 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

Price History for 255 Hillside Road
| Date | Price | Event | Source |
|---|---|---|---|
| 03/25/2025 | $1,625,000 | Sold | Smart MLS #24074345 |
| 03/17/2025 | $1,599,000 | Pending | Smart MLS #24074345 |
| 02/20/2025 | $1,599,000 | Listed For Sale | Smart MLS #24074345 |
| 09/11/2019 | $930,000 | Sold | Smart MLS #170196027 |
| 05/16/2019 | $975,000 | PriceChange | Agent Provided |
| 05/02/2019 | $989,000 | Listed For Sale | Agent Provided |
| 06/20/2017 | $850,000 | Sold | Smart MLS #99180937 |
| 04/26/2017 | $849,900 | Pending | Agent Provided |
| 04/10/2017 | $849,900 | Listed For Sale | Agent Provided |
| 10/21/2016 | $925,000 | ListingRemoved | Agent Provided |
| 03/02/2016 | $925,000 | Listed For Sale | Agent Provided |
| 12/06/2015 | $960,000 | ListingRemoved | Agent Provided |
| 10/09/2015 | $960,000 | PriceChange | Agent Provided |
| 07/15/2015 | $980,000 | Listed For Sale | Agent Provided |
| 05/01/1996 | $488,000 | Sold | N/A |
Market trends in Fairfield
Last updated May 2026
Avg. sale price
$921K
$34.17KMoM
Sale-to-List Price
102.7%
0.5%MoM
Price per sq ft
$498
$23MoM
Available listings
168
38MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $18,712 |
| Assessment | $659,120 |
Home facts updated by county records
Homeowner tools
Estimated monthly rent$7,945/mo
Homes for rent near 255 Hillside Road
See what comparable homes in the neighborhood are renting for.Comparable Sales for 255 Hillside Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.20 | Single-Family Home | $2,150,000 | 12/09/25 | 4 | 2.5 | 3,008 | |
0.54 | Single-Family Home | $1,600,000 | 08/27/25 | 5 | 3.5 | 4,033 | |
0.53 | Single-Family Home | $1,335,000 | 08/04/25 | 4 | 2.5 | 3,640 | |
0.52 | Single-Family Home | $2,210,000 | 06/02/26 | 5 | 2.5 | 3,435 | |
0.57 | Single-Family Home | $2,215,000 | 06/10/26 | 3 | 2.5 | 3,594 | |
0.38 | Single-Family Home | $2,875,000 | 06/11/26 | 5 | 5 | 5,924 | |
0.49 | Single-Family Home | $3,100,000 | 05/28/26 | 5 | 6 | 5,515 | |
0.72 | Single-Family Home | $1,018,000 | 07/25/25 | 4 | 2.5 | 2,638 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 255 Hillside Road.
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
78 % Say there's holiday spirit
76 % Say people would walk alone at night
71 % Say kids play outside
67 % 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
49 % Say there are community events
47 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 255 Hillside Road
Off Market Homes Near 255 Hillside Road

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.
255 Hillside Road, Fairfield, CT 06824 is a 4 bedroom, 4 bathroom, 3,918 sqft single-family home built in 1995. This property is not currently available for sale. 255 Hillside Road was last sold on Mar 25, 2025 for $1,625,000 (2% higher than the asking price of $1,599,000). The current Trulia Estimate for 255 Hillside Road is $1,710,300.