258 Bennett Street, Fairfield, CT 06825
OFF MARKET

258 Bennett Street
Fairfield, CT 06825

  • 3 Beds
  • 2 Baths
  • 1,063 sqft

$680,000

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $4,514/mo*
Refinance Your Home

$680,000

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $4,514/mo*
Refinance Your Home
3 Beds
2 Baths
1,063 sqft

Local Information

  • Map ViewExplore the area around 258 Bennett Street.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1953
Living Area
1,063 sqft
Price/Sqft
$640
Parking
1 Car Garage

Description

Great opportunity! 3 Beds plus Office/Study that is large and can be used as 4th bedroom. 2 bath home. House needs updates. Hardwood floors, large rear room not included in square footage is heated and part of living space to give total finished space to 1427 Sq. 2 Full floors plus basement and garage under house. Great location. Great Cul de sac in Fairfield. Bring best offers.
258 Bennett Street, Fairfield, CT 06825 is a 3 bedroom, 2 bathroom, 1,063 sqft single-family home built in 1953. It last sold for $415,000 on Aug 19, 2024 (13% below the $475,000 asking price). More recently, it was listed as a rental in March 2025 with an asking price of $5,000 per month. That rental listing was removed on April 20, 2025. It is currently off market. The Trulia Estimate is $680,000, with a rent estimate of $4,184/month.

Home Details for 258 Bennett Street

Interior Features

Interior Details
Basement: Full,Sump PumpNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Bathroom, Family Room, Kitchen, Office
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1063 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Electric Range, Refrigerator, Electric Water Heater, Water HeaterLaundry: Lower LevelRefrigerator
Heating & Cooling
Heating: Baseboard,Hot Water,OilHas CoolingAir Conditioning: Wall Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Rain GuttersFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageParking Spaces: 1Parking: Attached,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1063 Square Feet

Property Information

Year Built
Year Built: 1953
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 117135

Price & Status

Price
List Price: $475,000
Status Change & Dates
Off Market Date: Wed Jul 17 2024Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: Fairfield
School Information
Elementary School: North StratfieldJr High / Middle School: Fairfield Woods, Fairfield Wood Middle SchoolHigh School: Fairfield Warde

Agent Information

Buyer Agent
Buyer Company Name: Fowler Sakey & Team at William Raveis Real Estate

Building

Building Area
Building Area: 1063 Square Feet

HOA

No HOA

Lot Information

Lot Area: 5662.8 sqft

Miscellaneous

BasementMls Number: 24026223Attic: Access Via HatchAbove Grade Unfinished Area: 1063
Last check for updates: about 21 hours ago
Listed by Arin D. Hayden, (203) 258-0659
Levey Miller Maretz LLC, (203) 389-5377
Bought with: Jaime Memoli, (203) 904-0998, William Raveis Real Estate, (203) 255-6841
Source: Smart MLS, MLS#24026223

Price History for 258 Bennett Street

DatePriceEventSource
04/20/2025$5,000ListingRemovedZillow Rentals
03/29/2025$5,000Listed For RentZillow Rentals
08/19/2024$415,000Sold
Smart MLS #24026223
07/17/2024$475,000PendingSmart MLS #24026223
07/09/2024$475,000PriceChange
Smart MLS #24026223
07/03/2024$510,000PriceChange
Smart MLS #24026223
07/02/2024$530,000Listed For SaleSmart MLS #24026223
03/24/2021ListingRemovedN/A
07/16/2018$2,600ListingRemovedN/A
03/25/2018$2,600PriceChange
N/A
03/16/2018$2,625Listed For RentN/A
05/27/2017$2,500ListingRemovedN/A
04/02/2017$2,500Listed For RentN/A

Market trends in Fairfield

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$987K
$49KMoM
Sale-to-List Price
103.3%
0.6%MoM
Price per sq ft
$483
$16MoM
Available listings
178
10MoM
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Property Tax and Assessment

Year2025
Tax$6,967
Assessment$245,420
Home facts updated by county records

Comparable Sales for 258 Bennett Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
65 Bennett Street, Fairfield, CT
0.18
Single-Family Home
$625,000
08/20/25
4
2
1,724
1748 Stratfield Road, Fairfield, CT
0.08
Single-Family Home
$725,000
12/22/25
4
2
1,945
1924 Stratfield Road, Fairfield, CT
0.11
Single-Family Home
$432,500
07/06/26
3
1
1,248
1346 Stratfield Road, Fairfield, CT
0.45
Single-Family Home
$590,000
11/05/25
3
1.5
1,217
1780 Stratfield Road, Fairfield, CT
0.07
Single-Family Home
$750,000
06/05/26
3
2.5
2,568
575 Church Hill Road, Fairfield, CT
0.19
Single-Family Home
$750,000
05/18/26
3
2
1,689
33 Bennett Street, Fairfield, CT
0.21
Single-Family Home
$955,000
11/13/25
3
2.5
2,082
893 Church Hill Road, Fairfield, CT
0.12
Single-Family Home
$675,000
02/03/26
4
2.5
2,642
1822 Stratfield Road, Fairfield, CT
0.05
Single-Family Home
$750,000
06/16/26
4
2.5
2,420

Nearby homes

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Assigned Schools

These are the assigned schools for 258 Bennett Street.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

  • 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

  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 258 Bennett Street

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Off Market Homes Near 258 Bennett Street

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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.