239 Bailey Rd, Middletown, CT 06457
OFF MARKET

$340,700

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 1,231 sqft (on 0.27 acres)

239 Bailey Rd, Middletown, CT 06457

Est. Refi. Payment $2,457/mo*
Refinance Your Home
Currently Off Market - Sold Dec 3, 2008 for $220,000

Home Value

Trulia Estimate
$341K
Since last month
Decreased$7K (-2.1%)
Since last year
Increased$14K (+4.2%)
Since last sale
Increased$121K (+54.9%)
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 +94% in the last 10 years
MonthEstimated value
2026
October 2026$341K
September 2026$348K
August 2026$346K
July 2026$347K
June 2026$354K
May 2026$355K
April 2026$343K
March 2026$339K
February 2026$323K
January 2026$323K
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
85 Meech Road, Middletown, CT
0.37
Single-Family Home
$315,000
11/25/25
3
1
1,267
175 Newfield Street, Middletown, CT
0.32
Single-Family Home
$330,000
10/02/26
3
1
1,075
325 Barbara Road, Middletown, CT
0.12
Single-Family Home
$355,000
07/24/26
3
1.5
1,836
136 Westfield Street, Middletown, CT
0.07
Single-Family Home
$330,000
01/13/26
4
2
1,225
26 Fisher Rd, Middletown, CT
0.27
Single-Family Home
$300,000
05/20/26
3
2
1,075
85 Westmont Drive, Middletown, CT
0.16
Single-Family Home
$345,000
11/12/25
3
2
1,416
20 Navadon Pkwy, Middletown, CT
0.39
Single-Family Home
$225,000
07/06/26
3
2
864
337 Newfield St, Middletown, CT
0.33
Single-Family Home
$150,000
07/20/26
4
1
2,174
123 Fisher Road, Middletown, CT
0.38
Single-Family Home
$364,000
10/22/26
3
2
1,537
18 Phedon Parkway, Middletown, CT
0.37
Single-Family Home
$303,500
01/21/26
3
2
1,898

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
231 Bailey Road, Middletown, CT 06457
0.01
$344,200
3
1.5
986
Off Market
249 Bailey Rd, Middletown, CT 06457
0.02
$365,300
3
3
1,231
Off Market
168 Westfield St, Middletown, CT 06457
0.02
$347,100
3
1.5
1,324
Off Market
223 Bailey Rd, Middletown, CT 06457
0.03
$338,300
3
2
1,231
Off Market
19 Bailey Rd, Middletown, CT 06457
0.03
$300,600
3
2
1,026
Off Market
158 Westfield St, Middletown, CT 06457
0.03
$360,800
3
2
3,824
Off Market
27 Bailey Rd, Middletown, CT 06457
0.03
$306,500
3
2
1,026
Off Market
250 Bailey Rd, Middletown, CT 06457
0.04
$311,500
3
2
1,250
Off Market
240 Bailey Rd, Middletown, CT 06457
0.04
$338,400
3
1.5
1,026
Off Market
35 Bailey Rd, Middletown, CT 06457
0.04
$373,000
3
1.5
1,226
Off Market
232 Bailey Rd, Middletown, CT 06457
0.04
$337,100
3
2
1,026
Off Market
9 Bailey Rd, Middletown, CT 06457
0.04
$315,700
3
2
1,242
Off Market
217 Bailey Rd, Middletown, CT 06457
0.04
$333,300
3
2
986
Off Market
224 Bailey Rd, Middletown, CT 06457
0.05
$327,200
3
2
1,386
Off Market
196 Westfield St, Middletown, CT 06457
0.05
$327,200
4
2
1,225
Off Market
357 Barbara Rd, Middletown, CT 06457
0.06
$368,900
3
2
1,224
Off Market
209 Bailey Rd, Middletown, CT 06457
0.06
$366,400
4
2
1,354
Off Market
43 Bailey Road, Middletown, CT 06457
0.06
$396,800
3
2
1,501
Off Market
218 Bailey Rd, Middletown, CT 06457
0.06
$306,000
3
2
1,026
Off Market
49 Bailey Rd, Middletown, CT 06457
0.06
$347,900
4
2
1,210
Off Market

Local Information

  • Map ViewExplore the area around 239 Bailey Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1957
0.27 acre lot
1,231 sqft
$277/sqft

About this House

This move in ready charming cape on quiet street offers: Remodled Kitchen & baths,Refinished hdwd floors,fresh paint,custom builtins & recently painted exterior. Great deck, georgous yard, ideal to entertain and grill. Close to Shopping and major roads.
239 Bailey Rd, Middletown, CT 06457 is a 3 bedroom, 1 bathroom, 1,231 sqft single-family home built in 1957. It last sold for $220,000 on Dec 3, 2008. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $340,700, with a rent estimate of $2,327/month.

Home Details for 239 Bailey Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7
Heating & Cooling
Heating: Forced Air, GasHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other

Property Information

Year Built
Year Built: 1957
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.27 acres

Price and Tax history

DateEventPrice
Dec 3, 2008
Source: Smart MLS #G507023
Sold
$220,000
Aug 30, 2008
Source: Agent Provided
Listed For Sale
$244,000
Jun 21, 2004
Source: N/A
Sold
$199,900
Oct 26, 1994
Source: N/A
Sold
$116,500

Market trends in Middletown

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$350K
Sale-to-List Price
103.5%
0.1%MoM
Price per sq ft
$240
$4MoM
Available listings
89
4MoM
Sourced by Trulia Market Trends

Around this home

What Locals Say about Middletown

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 73% say there's holiday spirit
  • 71% say there are sidewalks
  • 48% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
At least 387 Trulia users voted on each feature.

  • 84 % Say it's dog friendly

  • 82 % Say car is needed

  • 74 % Say parking is easy

  • 73 % Say there's holiday spirit

  • 71 % Say there are sidewalks

  • 62 % Say yards are well-kept

  • 62 % Say people would walk alone at night

  • 61 % Say streets are well-lit

  • 61 % Say kids play outside

  • 55 % Say it's quiet

  • 52 % Say it's walkable to restaurants

  • 49 % Say there's wildlife

  • 48 % Say neighbors are friendly

  • 42 % Say they plan to stay for at least 5 years

  • 38 % Say it's walkable to grocery stores

  • 23 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Clutterbuck1835
    "The Leasing Office is very friendly and extremely helpful. From the application process through movein and beyond, they have answered my many, many questions patiently and with a smile. And my neighbors? After living here for one day, I made four friends and two four-legged ones. Lastly, the location couldn't be better. Everything is on Washington Street or in close proximity. Yes, I think I'm going to be very happy here!"
    0
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  • Amy Gallina
    "I commute three days per week to Hartford and it's about a 25 minute drive both ways"
    0
    Flag
  • Travis Thomas
    "The people are very very nice. I am very comfortable here . Not afraid to leave the front door open or the slider to the deck"
    1
    Flag
  • James.sargeant30
    "My friend lives there she loves it very much good place to live with family everyone works and goes to school"
    0
    Flag
  • Julia Taylor
    "very easy to get to and from work when living in middletown! I work in Cheshire. Just hop onto 691 and in 15 min you’re there. "
    0
    Flag
  • Calm Teacher
    "Good schools for the most part and safe neighborhoods. Students don’t have to wear uniforms. The town has a lot of nice parks. "
    0
    Flag
  • Life Withsymph
    "You get to see the dogs being walked and you can pet them and talk to the owners build bonds , you will be able to see all different types of dogs and mixes "
    0
    Flag
  • Phyloren
    "Watch your children it is not safe. The schools have fights every day. The learning atmosphere is is awful. "
    0
    Flag
  • Kelly Capone
    "I haven’t lived here long and I’m not exactly sure what community events make my neighborhood special. "
    2
    Flag
  • Dlc.marie0816
    "I moved out here in June and I definitely love it.. feels like a nice place for my family, specially my kids"
    0
    Flag
  • Trulia User
    "There are dog parks everywhere, and plenty of places to walk uour dog. Even if you are in an apartment "
    3
    Flag
  • Michael W. W.
    "Wadsworth mansion has many trails. They have several public events in the summer time. There are two other state parks very close that are easily accessible by foot or car. Main Street has many restaurants that offer dine-in, carry out and delivery."
    12
    Flag
  • Joseph V.
    "Middletown is a town that has enjoyable events such as the weekly farmers market the the fall festival and during Christmas time they put up the huge Christmas trees "
    3
    Flag
  • Marquis W. G.
    "My neighborhood is surrounded by semi luxury condos and townhouses full of hard working families. Very family oriented and very peaceful. I love it here!"
    3
    Flag
  • Ishmaila L.
    "Dog owners will like the space made to them to run around and exercise. There are also doggy bags available to help pick up dog waste."
    2
    Flag
  • Marquis W. G.
    "I just moved here recently and I love the community and neighbors. The property is very clean and the neighborhood feels very family oriented "
    0
    Flag
  • Francheska M.
    "Neighbors are very friendly with a really good community sense. Conveniently close to stores and park. "
    0
    Flag
  • Shelby W.
    "The commute downtown on public transportation has changed and not as Easy. Driving downtown is 5-7 minutes. Walking is a half hour. "
    0
    Flag
  • ISA M.
    "School system is awesome in Middletown Ct. You can walk around at night time and still feel safe! I like it that much!"
    0
    Flag
  • Sekernan
    "I drive about 7 or 8 miles to work. Traffic depends on day and time of day. Never too bad. Takes 11-15 minutes to get there. I am able to walk to some stores and laundromats in the area, sidewalks make this safe"
    0
    Flag
  • Richard D.
    "The is a walking/biking trail and a dog park. Nice clean areas safe for walking and locations for waste disposal."
    0
    Flag
  • Christina Y.
    "The schools are awesome for elementary and high school and college.The food here in the restaurants are good too."
    2
    Flag
  • Chelsea C.
    "it’s good but I drive there’s never much traffic which is good and easy to get to work and drive kids to school"
    1
    Flag
  • Michelle E. B.
    "my neighborhood has access to transportation, stores, schools, hospital and is close to downtown. "
    1
    Flag
  • Trevor N.
    "We live near wadsworth mansion so they often have public concerts, vendors, ect. Snow school is right down the road as well. "
    1
    Flag
  • Marisa
    "i think it’s a great place to own a dog .. i have a chocolate lab myself and their are tons of sidewalks and a bike trail as well. everyone’s pretty friendly & clean up after their dogs as well"
    0
    Flag
  • Frankie T.
    "Lots of pups here in Middletown and even some dog-friendly restaurant patios! Our dog loves the walkable North End."
    1
    Flag
  • Molinaronijhana
    "We have bike shows, Christmas carriage rides and a huge tree for Christmas, trick or treating on main st and a wonderful YMCA "
    1
    Flag
  • Shellycato19
    "A lot of dogs living in the area. Not a lot of places to really run, but nice places to take a long and peaceful walk. Unfortunately a lot of owners don’t clean up after their dogs, but it’s starting g to get a little better. Overall a decent place to have pups. "
    1
    Flag
  • Shewarrens
    "It’s a beautiful place to live , It’s a very nice place to grow your kids there’s of restaurant and park and transportation if you don’t drive"
    2
    Flag
  • Asweetrdrm
    "It's a good place to live, low crime rate. Neighbors are friendly. Plenty of kids and close to schools"
    1
    Flag
  • Kurt.r.wentzell
    "There’s not a lot of traffic on my street. A lot of the neighbors have dogs and you always see people walking their dogs on leashes. There’s also a park just down the street."
    1
    Flag
  • Qcockrell
    "more activities for the kids to keep them busy and there need to be more job opportunities for the ones that are looking for a job"
    1
    Flag
  • Lisa C.
    "the neighborhood is a private road with only 1 way in/out. everyone knows everyone. no crime all neighbors have lived here since 1950s and passed houses down through generations. the elementary school is in walking distance safe neighborhood where children could play in the road and not have to worry about traffic"
    2
    Flag
  • Wolver1068.jb
    "We have a great town to raise children in and is rated one of top towns in the United States for raising children. Lots of his Tory in town and the surrounding areas. Great place to have a family vacation!"
    0
    Flag
  • Alnoor R.
    "Decent schools,safe, plenty of kid friendly space. Property taxes are high in CT. Job marked is tepid at best"
    0
    Flag
  • Brian
    "great central location in CT, close to downtown and highways. quiet neighborhood, but properties very close together"
    0
    Flag
  • Kathy
    "Best restaurant and nightlife scene in the area. outstanding, unique restaurants and small businesses. Plenty of daytime family events on Main street like car shows, bike shows, Christmas tree lighting. Vibrant, diverse community in a college town with a lot of great history that is still celebrated."
    0
    Flag
  • Mhasbro13
    "I’ve lived in this community for 4 years. I love the amenities offered to us. My neighbors are very friendly. Most everyone will say hello when they see you, even if they don’t know you. Great place to liven."
    0
    Flag
  • Leonardo V.
    "It is a very safe place to live..also shopping is close. The neighbors are friendly and very courteous.."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 239 Bailey Rd

  • What is 239 Bailey Rd estimated to be worth?
    Trulia's estimated value for 239 Bailey Rd in Middletown, CT is $340,700.
  • What is the price history for 239 Bailey Rd?
    239 Bailey Rd in Middletown, CT last sold for $220,000 in December 2008.
  • Is Middletown a buyer's or seller's market?
    Middletown is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Middletown?
    The median sale price in Middletown is $350K. That is roughly unchanged from the prior month.
  • How big is the lot at 239 Bailey Rd?
    The lot at 239 Bailey Rd in Middletown, CT is about 0.27 acres (11,761 sq ft).

Explore by feature - Pet Friendly

49 pet-friendly rentals in Middletown, CT

Explore by feature - Garage

7 rentals with a garage in Middletown, CT

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Explore by feature - Pool

12 homes with a pool in Middletown, CT

Explore by feature - Washer/dryer

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Apartments for Rent

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Off Market Homes Near 239 Bailey Rd

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Homes for sale near 239 Bailey Rd

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