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

50 Bailey Rd
Middletown, CT 06457

  • 3 Beds
  • 3 Baths
  • 1,646 sqft (on 0.46 acres)

$444,000

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $3,051/mo*
Refinance Your Home

$444,000

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $3,051/mo*
Refinance Your Home
3 Beds
3 Baths
1,646 sqft
(on 0.46 acres)

Local Information

  • Map ViewExplore the area around 50 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
1956
Lot Size
0.46 acres
Living Area
1,646 sqft
Price/Sqft
$270

About this House

ROOM FOR THE WHOLE FAMILY. THIS IS NOT A DRIVEBY - VERY NICELY MAINTAINED 3 BEDROOM / 3 FULL BATH CAPE. INTERIOR HAS BEEN TOTALLY RE-PAINTED, WOOD FLOORS RE-FINISHED, REFRESHED KITCHEN WITH NEWER APPLIANCES AND COUNTERTOPS. EFFICIENT GAS HEAT AND HOT WATER, UPDATED BATHS, LARGE MAIN LEVEL MASTER BEDROOM, FULL BATH ON 1ST AND SECOND FLOORS AND FULL BATH IN BASEMENT LEVEL. CITY RECORDS INDICATE THIS IS A 3 BEDROOM HOME, HOWEVER, THERE IS A ROOM ON THE FIRST FLOOR WITH A CLOSET THAT CAN BE USED FOR AN OFFICE, NURSERY OR 4TH BEDROOM. SOME AREAS OF THE BASEMENT ARE HEATED AND COULD BE FINISHED TO PROVIDE ADDITIONAL LIVING SPACE. SPACIOUS REAR YARD WITH A TREE BOUNDARY PROVIDES 3 SEASON PRIVACY. TWO SHEDS ARE LOCATED ON THE PROPERTY TO PROVIDE MORE THAN AMPLE EXTERIOR STORAGE SPACE. CONVENIENT LOCATION - WALK TO SPENCER SCHOOL, MINUTES FROM CITY CENTER, SHOPPING AREAS AND MAJOR HIGHWAYS. READY FOR IMMEDIATE OCCUPANCY, WILL EASILY QUALIFY FOR ALL TYPES OF FINANCING.
50 Bailey Rd, Middletown, CT 06457 is a 3 bedroom, 3 bathroom, 1,646 sqft single-family home built in 1956. It last sold for $260,000 on Apr 30, 2008. It is currently off market. The Trulia Estimate is $444,000, with a rent estimate of $3,047/month.

Home Details for 50 Bailey Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7
Heating & Cooling
Heating: Other, GasAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
Parking Space: 1Parking: Carport

Property Information

Year Built
Year Built: 1956Year Updated: 1956
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price History for 50 Bailey Rd

DatePriceEventSource
11/13/2018$228,000ListingRemovedAgent Provided
09/26/2018$228,000Listed For SaleAgent Provided
04/30/2008$260,000Sold
Smart MLS #N269557
03/05/2008$274,900Listed For SaleAgent Provided
01/27/1994$124,000Sold
N/A

Market trends in Middletown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$293K
$11.67KMoM
Sale-to-List Price
103.3%
0.9%MoM
Price per sq ft
$236
$1MoM
Available listings
92
8MoM
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Property Tax and Assessment

Year2025
Tax$7,062
Assessment$181,550
Home facts updated by county records

Comparable Sales for 50 Bailey Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
88 Bailey Road, Middletown, CT
0.07
Single-Family Home
$390,000
07/16/26
3
2
2,242
85 Westmont Drive, Middletown, CT
0.19
Single-Family Home
$345,000
11/12/25
3
2
1,416
136 Westfield Street, Middletown, CT
0.08
Single-Family Home
$330,000
01/13/26
4
2
1,225
281 Old Mill Road, Middletown, CT
0.23
Single-Family Home
$410,000
09/29/25
3
2.5
1,902
45 Fisher Rd, Middletown, CT
0.22
Single-Family Home
$350,000
10/07/25
3
2
1,267
18 Phedon Parkway, Middletown, CT
0.44
Single-Family Home
$303,500
01/21/26
3
2
1,898
26 Fisher Rd, Middletown, CT
0.22
Single-Family Home
$300,000
05/20/26
3
2
1,075
27 Valley Drive, Middletown, CT
0.37
Single-Family Home
$530,000
01/09/26
3
2.5
2,204
87 Meech Rd, Middletown, CT
0.37
Single-Family Home
$232,500
05/29/26
4
3
2,369
152 Old Mill Road, Middletown, CT
0.47
Single-Family Home
$355,000
08/29/25
3
2
1,748

Nearby homes

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Assigned Schools

These are the assigned schools for 50 Bailey Rd.
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 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.
  • 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
  • Marisa
    "commute is pretty good, surrounded by plenty of stores and easy access to many restaurants and everything one could need"
    0
    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
  • Jagalpure.prafull
    "Nice city and nebourhood. Good parks nearby. very well connected to major highways. Boston and New York are nearest best cities to explore. "
    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

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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 50 Bailey Rd

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Off Market Homes Near 50 Bailey Rd

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