166 Bailey Rd, Fairfield, CT 06825
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Property image
OFF MARKET

166 Bailey Rd
Fairfield, CT 06825

  • 5 Beds
  • 3 Baths
  • 3,576 sqft (on 0.52 acres)

$1,093,000

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $7,198/mo*
Refinance Your Home

$1,093,000

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $7,198/mo*
Refinance Your Home
5 Beds
3 Baths
3,576 sqft
(on 0.52 acres)

Home Value

Trulia Estimate
$1.09M
Since last month
Decreased$15K (-1.3%)
Since last year
Increased$63K (+6.2%)
Since last sale
Increased$330K (+43.3%)
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 +86% in the last 10 years
MonthEstimated value
2026
August 2026$1.09M
July 2026$1.11M
June 2026$1.11M
May 2026$1.11M
April 2026$1.09M
March 2026$1.09M
February 2026$1.04M
January 2026$1.02M
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
65 Bailey Road, Fairfield, CT
0.09
Single-Family Home
$893,000
04/01/26
3
2
2,888
250 Lockwood Road, Fairfield, CT
0.13
Single-Family Home
$989,375
03/19/26
4
2
2,028
564 Fairfield Woods Road, Fairfield, CT
0.43
Single-Family Home
$875,000
09/08/25
5
3.5
3,258
120 Saddle View Road, Fairfield, CT
0.28
Single-Family Home
$1,350,000
07/24/26
5
4
3,310
51 Grandview Road, Fairfield, CT
0.25
Single-Family Home
$855,000
07/20/26
3
2.5
2,978
1822 Stratfield Road, Fairfield, CT
0.31
Single-Family Home
$750,000
06/16/26
4
2.5
2,420
151 Bulkley Drive, Fairfield, CT
0.35
Single-Family Home
$930,000
09/02/25
3
1.5
3,448
168 Bennett Street, Fairfield, CT
0.29
Single-Family Home
$976,000
03/27/26
4
3
2,175
1470 Stratfield Road, Fairfield, CT
0.24
Single-Family Home
$826,000
06/15/26
3
2.5
2,594
66 Wynn Wood Drive, Fairfield, CT
0.45
Single-Family Home
$975,000
07/06/26
4
4
3,134

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
210 Bailey Road, Fairfield, CT 06825
0.03
$906,100
4
2.5
2,094
Off Market
121 Argonne Street, Fairfield, CT 06432
0.06
$681,000
3
1.5
1,748
Off Market
120 Argonne Street, Fairfield, CT 06432
0.08
$680,800
3
2
1,449
Off Market
65 Bailey Road, Fairfield, CT 06825
0.09
$893,000
3
2
2,888
Recently Sold
518 Lockwood Road, Fairfield, CT 06825
0.11
$1,142,300
5
3.5
4,217
Off Market
120 Louvain Street, Fairfield, CT 06825
0.13
$830,500
3
2
2,540
Off Market
271 Ridgeview Avenue, Fairfield, CT 06825
0.12
$1,066,800
4
2.5
2,147
Off Market
43 Argonne Street, Fairfield, CT 06825
0.14
$947,600
3
1.5
1,664
Off Market
31 Godfrey Road, Fairfield, CT 06825
0.13
$832,700
3
2
1,950
Off Market
250 Lockwood Road, Fairfield, CT 06825
0.13
$989,375
4
2
2,028
Recently Sold
50 Lisbon Drive, Fairfield, CT 06825
0.17
$1,670,000
4
4.5
4,007
Recently Sold
268 Ridgeview Avenue, Fairfield, CT 06825
0.16
$1,311,300
5
3.5
3,136
Off Market

Local Information

  • Map ViewExplore the area around 166 Bailey Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1959
Lot Size
0.52 acres
Living Area
3,576 sqft
Price/Sqft
$306
Parking
Garage

About this House

Come see this four level split set on private half acre lot in Stratfield neighborhood. A versatile floor plan of close to 3600 square feet of modern living space centered around an updated kitchen with stainless appliances and a granite countered breakfast bar overseeing an adjoining solarium. A large family room with vaulted ceilings and custom built-ins perfect for gatherings while a separate media room in the lower level featuring a retractable screen is the great place to binge watch your favorite shows. A separate suite in the lower level works nicely for guests or an au-pair suite. A private level back yard overlooks an expansive patio. Ideally located close to all schools as well as a public golf course, this 5 bedroom 3 bath home is a must see!
166 Bailey Rd, Fairfield, CT 06825 is a 5 bedroom, 3 bathroom, 3,576 sqft single-family home built in 1959. It last sold for $762,500 on Jul 8, 2021. It is currently off market. The Trulia Estimate is $1,093,000, with a rent estimate of $6,291/month.

Home Details for 166 Bailey Rd

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: Single Family HomeArchitecture: Split-level

Community

Units in Building: 1

Lot Information

Lot Area: 0.52 acres

Price and Tax history

DateEventPrice
Jul 8, 2021
Source: Smart MLS #170400735
Sold
$762,500
Mar 22, 2019
Source: Smart MLS #170161327
Sold
$650,000
Mar 22, 2019
Source: Agent Provided
PendingToActive
$659,000
Feb 20, 2019
Source: Agent Provided
Pending
$659,000
Feb 7, 2019
Source: Agent Provided
PriceChange
$659,000
Price decreased by 5%

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

LGBTQ Local Legal Protections

Frequently asked questions about 166 Bailey Rd

  • What is 166 Bailey Rd estimated to be worth?
    Trulia's estimated value for 166 Bailey Rd in Fairfield, CT is $1,093,000.
  • What is the price history for 166 Bailey Rd?
    166 Bailey Rd in Fairfield, CT last sold for $762,500 in July 2021.
  • 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 166 Bailey Rd have air conditioning?
    Yes, 166 Bailey Rd in Fairfield, CT has air conditioning.
  • How big is the lot at 166 Bailey Rd?
    The lot at 166 Bailey Rd in Fairfield, CT is about 0.52 acres (22,651 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 166 Bailey Rd

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