209 Bailey Rd, Middletown, CT 06457
Property image
Property image
OFF MARKET

209 Bailey Rd
Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 1,354 sqft (on 0.27 acres)

$375,600

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $2,591/mo*
Refinance Your Home

$375,600

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $2,591/mo*
Refinance Your Home
4 Beds
2 Baths
1,354 sqft
(on 0.27 acres)

Home Value

Trulia Estimate
$376K
Since last month
Decreased$1K (-0.3%)
Since last year
Increased$13K (+3.5%)
Since last sale
Increased$178K (+90.1%)
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 +93% in the last 10 years
MonthEstimated value
2026
August 2026$375K
July 2026$376K
June 2026$384K
May 2026$383K
April 2026$371K
March 2026$369K
February 2026$351K
January 2026$353K
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
136 Westfield Street, Middletown, CT
0.11
Single-Family Home
$330,000
01/13/26
4
2
1,225
85 Westmont Drive, Middletown, CT
0.12
Single-Family Home
$345,000
11/12/25
3
2
1,416
325 Barbara Road, Middletown, CT
0.18
Single-Family Home
$355,000
07/24/26
3
1.5
1,836
45 Fisher Rd, Middletown, CT
0.29
Single-Family Home
$350,000
10/07/25
3
2
1,267
26 Fisher Rd, Middletown, CT
0.29
Single-Family Home
$300,000
05/20/26
3
2
1,075
33 Bartlett Holw, Middletown, CT
0.35
Single-Family Home
$460,000
10/31/25
3
2
1,409
87 Meech Road, Middletown, CT
0.42
Single-Family Home
$232,500
05/29/26
4
3
2,369
Lot 8 Nathan Hale Road, Middletown, CT
0.42
Single-Family Home
$499,900
05/29/26
3
2
1,540
18 Phedon Parkway, Middletown, CT
0.42
Single-Family Home
$303,500
01/21/26
3
2
1,898
31 Broadview Parkway, Middletown, CT
0.48
Single-Family Home
$315,000
01/08/26
3
2
1,382

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
0.04
$350,600
3
1.5
986
Off Market
43 Bailey Road, Middletown, CT 06457
0.04
$404,000
3
2
1,501
Off Market
136 Westfield Street, Middletown, CT 06457
0.11
$330,000
4
2
1,225
Recently Sold
75 Westmont Drive, Middletown, CT 06457
0.11
$378,200
4
2.5
1,550
Off Market
88 Bailey Road, Middletown, CT 06457
0.10
$390,000
3
2
2,242
Recently Sold
85 Westmont Drive, Middletown, CT 06457
0.12
$345,000
3
2
1,416
Recently Sold
50 Military Road, Middletown, CT 06457
0.15
$310,100
3
1
1,175
Off Market
104 Bailey Road, Middletown, CT 06457
0.12
$447,800
4
2
2,129
Off Market
334 Barbara Road, Middletown, CT 06457
0.17
$366,600
3
2
2,448
Off Market
84 Westfield Street, Middletown, CT 06457
0.15
$525,300
4
2
1,857
Off Market
325 Barbara Road, Middletown, CT 06457
0.18
$355,000
3
1.5
1,836
Recently Sold
124 Westmont Drive, Middletown, CT 06457
0.15
$408,000
3
2
1,234
Off Market

Local Information

  • Map ViewExplore the area around 209 Bailey Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1957
Lot Size
0.27 acres
Living Area
1,354 sqft
Price/Sqft
$277

About this House

Don't miss this charming cozy cape featuring a beautifully remodeled Kitchen w/Stainless Steel appliances, new roof, siding and windows. New furnace in 2007. Fireplace, finished lower level with optional Pellet Stove. Includes 2 additional rooms in lower level for possible in-law. Sliders to deck, great level yard, convenient to highway,school,and shopping. Contact Annemarie McPherson, 1-800-525-7793 or visit WWW.C21ALLPOINTSREALTY.COM.
209 Bailey Rd, Middletown, CT 06457 is a 4 bedroom, 2 bathroom, 1,354 sqft single-family home built in 1957. It last sold for $197,000 on Mar 31, 2015. It is currently off market. The Trulia Estimate is $375,600, with a rent estimate of $2,572/month.

Home Details for 209 Bailey Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7Types of Rooms: Dining Room, Family Room
Heating & Cooling
Heating: Forced Air, GasHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood, Laminate
Appliances & Utilities
Cable ReadyDisposalMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Vinyl

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
Mar 31, 2015
Source: Smart MLS #N352133
Sold
$197,000
Jan 17, 2015
Source: Agent Provided
Pending
$199,900
Dec 27, 2014
Source: Agent Provided
PriceChange
$199,900
Price decreased by 2%
Nov 18, 2014
Source: Agent Provided
PriceChange
$204,900
Price decreased by 1%
Sep 13, 2014
Source: Agent Provided
PriceChange
$206,900
Price decreased by 1%

Market trends in Middletown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$329K
$35.67KMoM
Sale-to-List Price
103.7%
0.4%MoM
Price per sq ft
$241
$5MoM
Available listings
78
14MoM

Around this home

What Locals Say about Middletown

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 209 Bailey Rd

  • What is 209 Bailey Rd estimated to be worth?
    Trulia's estimated value for 209 Bailey Rd in Middletown, CT is $375,600.
  • What is the price history for 209 Bailey Rd?
    209 Bailey Rd in Middletown, CT last sold for $197,000 in March 2015.
  • 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 $329K. That is up $35.67K from the prior month.
  • How big is the lot at 209 Bailey Rd?
    The lot at 209 Bailey Rd in Middletown, CT is about 0.27 acres (11,761 sq ft).

Explore by feature - Pet Friendly

53 pet-friendly rentals in Middletown, CT

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

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Apartments for Rent

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Off Market Homes Near 209 Bailey Rd

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Homes for sale near 209 Bailey Rd

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