29 Bailey Dr, Westfield, MA 01085
OFF MARKET

$587,700

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,872 sqft (on 0.72 acres)

29 Bailey Dr, Westfield, MA 01085

Est. Refi. Payment $3,732/mo*
Refinance Your Home
Currently Off Market - Sold Dec 1, 2011 for $325,000

Home Value

Trulia Estimate
$588K
Since last month
Decreased$9K (-1.5%)
Since last year
Increased$15K (+2.6%)
Since last sale
Increased$263K (+81%)
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 +76% in the last 10 years
MonthEstimated value
2026
August 2026$588K
August 2026$588K
July 2026$597K
June 2026$593K
May 2026$601K
April 2026$586K
March 2026$587K
February 2026$564K
January 2026$570K
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
16 Glen Ridge Dr, Westfield, MA
0.39
Single-Family Home
$460,000
10/10/25
3
1.5
1,547
125 Barbara St, Westfield, MA
0.89
Single-Family Home
$350,000
12/16/25
4
2
1,632
40 Barbara St, Westfield, MA
0.66
Single-Family Home
$260,000
12/24/25
3
1
1,044
22 Root Rd, Westfield, MA
0.95
Single-Family Home
$570,000
12/02/25
4
2.5
2,425
118 Woodside Ter, Westfield, MA
0.88
Single-Family Home
$340,000
02/11/26
3
1
1,242
163 Barbara St, Westfield, MA
0.95
Single-Family Home
$402,125
01/16/26
3
2
1,968
357 Southampton Rd, Westfield, MA
0.85
Single-Family Home
$374,000
04/30/26
4
1.5
1,573
164 Barbara St, Westfield, MA
0.93
Single-Family Home
$449,000
09/04/26
4
3
2,228
883 Southampton Rd, Westfield, MA
0.59
Single-Family Home
$230,000
01/30/26
2
1
1,243
194 Lockhouse Rd, Westfield, MA
0.98
Single-Family Home
$310,000
12/23/25
3
1
1,152

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
25 E Glen Dr, Westfield, MA 01085
0.27
$451,300
3
2
1,420
Off Market
35 E Glen Dr, Westfield, MA 01085
0.30
$629,900
5
3
2,676
For Sale
21 W Glen Dr, Westfield, MA 01085
0.31
$548,600
3
2.5
2,024
Off Market
27 W Glen Dr, Westfield, MA 01085
0.33
$567,200
4
3
2,076
Off Market
868 Southampton Rd #12, Westfield, MA 01085
0.44
-
2
1
720
Off Market
868 Southampton Rd #18, Westfield, MA 01085
0.44
$67,500
3
1
720
Recently Sold
868 Southampton Rd #76, Westfield, MA 01085
0.44
-
2
1
684
Off Market
868 Southampton Rd #54, Westfield, MA 01085
0.44
$94,900
1
1
644
Recently Sold
868 Southampton Rd #6, Westfield, MA 01085
0.44
$84,100
2
1
600
Off Market
868 Southampton Rd #70, Westfield, MA 01085
0.44
$138,000
2
1
912
Recently Sold
868 Southampton Rd #43, Westfield, MA 01085
0.44
$91,900
2
1
672
For Sale
868 Southampton Rd #72, Westfield, MA 01085
0.44
$55,000
2
1
720
Recently Sold

Local Information

  • Map ViewExplore the area around 29 Bailey Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2011
0.72 acre lot
1,872 sqft
$314/sqft

About this House

WESTFIELD New construction 4 bd 2.5 bath col. Open floor plan.Rod iron staircase, granite kitchen with island and huge pantry. Hdwd floors first floor and upstairs hallway. Central air, roughed for central vac. 2 x 6 construction. Energy efficient home in area of new 18 lot subdivision. 24 x22 garage. November 30th occupancy. $339,900
29 Bailey Dr, Westfield, MA 01085 is a 3 bedroom, 3 bathroom, 1,872 sqft single-family home built in 2011. It last sold for $325,000 on Dec 1, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $587,700, with a rent estimate of $2,818/month.

Home Details for 29 Bailey Dr

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.72 acres

Price and Tax history

DateEventPrice
Dec 1, 2011
Source: N/A
Sold
$325,000
Feb 25, 2011
Source: N/A
Sold
$314,900

Market trends in Westfield

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$390K
$12.5KMoM
Sale-to-List Price
—
Price per sq ft
$236
$12MoM
Available listings
76
10MoM

Around this home

What Locals Say about Westfield

At least 257 Trulia users voted on each feature.

  • 84 % Say car is needed

  • 84 % Say it's dog friendly

  • 80 % Say parking is easy

  • 74 % Say yards are well-kept

  • 72 % Say kids play outside

  • 72 % Say there's holiday spirit

  • 70 % Say people would walk alone at night

  • 67 % Say there's wildlife

  • 65 % Say there are sidewalks

  • 64 % Say streets are well-lit

  • 55 % Say neighbors are friendly

  • 54 % Say they plan to stay for at least 5 years

  • 53 % Say it's quiet

  • 49 % Say it's walkable to grocery stores

  • 47 % Say it's walkable to restaurants

  • 32 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Amrreni
    "4th Fireworks, art fair, holiday outdoor events at Xmas and Halloween, concerts, Stanley park events, animal sanctuary events"
    0
    Flag
  • Amrreni
    "There are a few events throughout the year that are held downtown the bring people together in the center and support local businesses which is nice."
    0
    Flag
  • Elizabeth Desmarais
    "Quiet neighborhood with respectful neighbors; many of which we know on a first name basis. Quick access to downtown. Convenient location. Lots of options for retail, groceries, activity/leisure. We love the location of our home. "
    4
    Flag
  • Asi924
    "Great safe neighborhoods surround this area. The majority are older and friendly. New great younger families have been moving in which is a breath of fresh air. Over all very welcoming. "
    0
    Flag
  • Ortizgermany
    "There’s so many kid-friendly places around and very friendly neighbors. I definitely feel safe everywhere I go in Westfield."
    9
    Flag
  • Lynziewk
    "It is a nice neighborhood for walking or riding your bikes. It is safe for older kids to walk or ride reasonable distances in pairs or groups during the day. "
    3
    Flag
  • Carolanncrosier
    "People are always walking their dogs and most residents own a dog. Recommend a fence as there are foxes, fisher cats and other wildlife. "
    2
    Flag
  • K.lafountaine82
    "It's congested getting from the Southern outskirts of town to the Pike but on the North end it's a snap. Traffic gets congested here as many folks use Westfield as a thru-way to access the hill towns and the town's in general that border Westfield."
    2
    Flag
  • Larissa C.
    "Normally, the farmers market would be open in Westfield center and also many tag sales and flea markets tend to pop up in the neighborhood. "
    3
    Flag
  • Tracydegray
    "I see people walking dogs all the time. Safe place to walk them. Nice park here Stanley Park. People keep their dogs on leashes."
    1
    Flag
  • Nadnekon
    "We have been living here for 3 years now. It’s a safe place to live and raise kids. Easy access to Mass Pike. "
    1
    Flag
  • Mallory K.
    "I drive my own vehicle on the Mass Pike to get to work daily. There is no public transportation option that is viable to get me from Westfield to where I work in Springfield. there is a bus system but it would take over an hour and several transfers. Westfield is a community where you need your own vehicle. "
    1
    Flag
  • Ashleeroe82
    "There a frequently free concerts on the “greens” in the summer. Which is the center of town. They also do seasonal celebrations as well. There’s a farmers market on Thursday. We host a very large 5K run/walk every year. And of course there Stanley Park! "
    0
    Flag
  • Lisa P., MD
    "We have dogs in our neighborhood. Everyone is very friendly. Our neighborhood gets busy during the day as our street is used as a shortcut. There are times when vehicles and motorcycles drive too fast down our street that has lots of children."
    6
    Flag
  • Harley505
    "Safe area fro children to grow up in... water sports, play grounds and public beaches! Local schools are outstanding!"
    0
    Flag
  • Harley505
    "Great quite area... no traffic on our street and the lake is awesome! Low to no crime, street lights keep things well lit! Close to everything that you would like, shopping, recreational area, and health providers!"
    0
    Flag
  • Nicole
    "great school! library, kids museum, sports facilities,stanley park. there are things to do in town as a family for little or no cost. mix of being closer to nature and convenience of city living. "
    1
    Flag
  • Master0113@comcast.net
    "I've lived here for many years & great neighbors who "look out for" each other. Nice state park with beach nearby & shopping plaza... LOTS of pond (Hampton Ponds) nearby. There's a bit of "country" feel, but city convenience!"
    2
    Flag
  • Marcelle
    "Yes I love living here, feel safe, never had issues with packages being delivered, will walk my dog at 12am if I feel like it... quiet and my neighbors are amazing "
    1
    Flag
  • Hwyman0170
    "My commute differs on a daily basis but never more than a 30 minute commute. There is generally moderate traffic but nothing unbearable "
    0
    Flag
  • Chad T.
    "30 minutes to work. 20 minutes to Costco, movies, Olive Garden. easy access to mass pike and 91. "
    0
    Flag
  • LA
    "People walk their dogs all the time in this neighborhood. I own two dogs and my neighbors love them. "
    1
    Flag
  • Asi924
    "The neighborhood is pleasant and safe. Friendly neighbors who love animals. Great school and activities. "
    0
    Flag
  • Randi L. M.
    "Many dog owners in this neighborhood - it’s very dog-friendly. People are always walking their dogs. "
    0
    Flag
  • Stephanie L.
    "Great neighborhood to have a dog. Very quiet. Cars drive slowly for the most part. Some people walk their dogs at night."
    0
    Flag
  • rjm7085
    "Kid friendly neighborhood, quiet, close to major highways, close to malls, easy access to nearby towns"
    0
    Flag
  • Randi L. M.
    "My commute has easy access to both downtown and to the highway. There is never much traffic. I enjoy my commute. "
    0
    Flag
  • Jennifer D.
    "great family neighborhood great schools. lots of kids playgrounds and parks great families lots of stores abd restaurants lots of things to do and see"
    0
    Flag
  • Benjamin S.
    "great people very friendly and beautiful location Great Schools and a glass of hiking biking and water activities to do all around us all year round"
    1
    Flag
  • Celia A.
    "I have lived in my neighborhood for 8 years. I met many of my neighbors and felt proud of my apartment and the grounds."
    0
    Flag
  • Pirate11liz
    "Whip city fiber is great, we no longer have to use Comcast!!!!!!!!!!!! We have our own electricity. It is a great location to get to different areas. "
    1
    Flag
  • Patricia M. J.
    "Quiet street with great neighbors."
    0
    Flag
  • Marge S.
    "We live and have offices in our home. While access to downtown is good, access to major highways east, west, north and south are excellent. Thirty minutes from top cultural areas in the Berkshires; 90 minutes to Boston. Thirty minutes to Northampton restaurants, entertainment and colleges."
    0
    Flag
  • Elizabeth L.
    "walking distance to beautiful Stanley Park & schools. Quiet friendly neighborhood"
    0
    Flag
  • Janice B. C.
    "Multigenerational community, excellent elementary school (Munger Hill), dog walk friendly, close to shopping center (Big Y, Staples, Job Lot, Bon-Ton, CVS) Home Depot, Walmart, car stores, much more. Public Transportation on Rt. 20 & 187 Little River Turnpike. Close to downtown Westfield, Stanley Park, Westfield State University and to multiple venues en route to Downtown Springfield. 10 min to Route 90 easy ride to Rt. 91. 15 min to Holyoke Mall (access to Rt. 91)"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 29 Bailey Dr

  • What is 29 Bailey Dr estimated to be worth?
    Trulia's estimated value for 29 Bailey Dr in Westfield, MA is $587,700.
  • What is the price history for 29 Bailey Dr?
    29 Bailey Dr in Westfield, MA last sold for $325,000 in December 2011.
  • Is Westfield a buyer's or seller's market?
    Westfield is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Westfield?
    The median sale price in Westfield is $390K. That is up $12.5K from the prior month.
  • How big is the lot at 29 Bailey Dr?
    The lot at 29 Bailey Dr in Westfield, MA is about 0.72 acres (31,363 sq ft).

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