227 East Main Street, Middletown, CT 06457
Property image
Property image
FOR SALE

227 East Main Street
Middletown, CT 06457

  • 9 Beds
  • 4.5 Baths
  • 3,180 sqft

$749,900

Original price: $799,900
Est. Mortgage $5,086/mo*
Get Pre-Qualified

$749,900

Original price: $799,900
Est. Mortgage $5,086/mo*
Get Pre-Qualified
9 Beds
4.5 Baths
3,180 sqft

Home Highlights

Parking
3 Car Garage
Climate Control
Heating & Cooling
Price/Sqft
$236
Listed
96 days ago

Local Information

  • Map ViewExplore the area around 227 East Main Street.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Outstanding Mixed-Use Investment Opportunity at 227 East Main Street, Middletown, CT Now offered at a newly reduced price, 227 East Main Street presents an exceptional opportunity for investors or owner-occupants seeking strong income potential and long-term value. This well-maintained mixed-use property features three spacious townhouse-style residential units, each offering 3 bedrooms, 1 full bath, 1 half bath, bright living spaces, and eat-in kitchens-highly desirable layouts that help attract and retain tenants. A standout feature is that each unit includes its own private under-house garage with direct access, creating the convenience and feel of a single-family home. The property also offers ample off-street parking and a driveway behind the building, providing easy access and added convenience for residents and guests. Separate utilities, hardwood floors, abundant natural light, and additional basement storage further enhance the property's appeal and ease of management. Ideally located near downtown Middletown, shopping, dining, parks, major commuter routes, Wesleyan University, and Middlesex Health, this property benefits from strong rental demand and excellent accessibility. With its price improvement, desirable townhouse-style units, private garages, ample parking, and proven income-producing potential, 227 East Main Street is a compelling investment opportunity in the heart of Middletown. Agent owner related.

Home Details for 227 East Main Street

Interior Features

Interior Details
Basement: Partial,Garage Access,ConcreteNumber of Rooms: 15
Beds & Baths
Number of Bedrooms: 9Number of Bathrooms: 6Number of Bathrooms (full): 3Number of Bathrooms (half): 3
Dimensions and Layout
Living Area: 3180 Square Feet
Appliances & Utilities
Appliances: Electric Water Heater, Water HeaterLaundry: In Unit,In Basement
Heating & Cooling
Heating: Baseboard,ElectricHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
No Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt GableExterior: SidewalkFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Paved,Off Street,Driveway
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3180 Square Feet

Days on Market

Days on Market: 96

Property Information

Year Built
Year Built: 1991
Property Type / Style
Property Type: Residential IncomeProperty Subtype: Multi FamilyArchitecture: 3sides - Units Are Side-by-Side
Building
Construction Materials: Vinyl SidingNot a New ConstructionAttached To Another StructureDoes Not Include Home Warranty
Property Information
Parcel Number: 1009154

Price & Status

Price
List Price: $749,900Price Per Sqft: $236
Status Change & Dates
Possession Timing: Immediately

Active Status

MLS Status: Active

Location

Direction & Address
City: Middletown
School Information
Elementary School: Per Board of EdJr High / Middle School: Per Board of EdHigh School: Per Board of Ed

Agent Information

Listing Agent
Listing ID: 24171799

Building

Building Area
Building Area: 3180 Square Feet

Community

Community Features: Medical Facilities, Park, Near Public Transport, Shopping/Mall

HOA

No HOA

Lot Information

Lot Area: 7405.2 sqft

Miscellaneous

BasementMls Number: 24171799Attic: NoneAttribution Contact: (860) 538-4448Above Grade Unfinished Area: 3180

Additional Information

Medical FacilitiesParkNear Public TransportShopping/Mall
Last check for updates: about 2 hours ago
Listing courtesy of Tanya Reyes, (860) 538-4448
William Raveis Real Estate, (860) 538-4448
Source: Smart MLS, MLS#24171799
Also Listed on Smart MLS.

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

Price History for 227 East Main Street

DatePriceEventSource
06/25/2026$749,900PriceChange
Smart MLS #24171799
05/31/2026$799,900PriceChange
Smart MLS #24171799
05/01/2026$850,000Listed For SaleSmart MLS #24171799
06/19/1992$170,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$10,384
Assessment$280,570
Home facts updated by county records

Comparable Sales for 227 East Main Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
203 East Main Street, Middletown, CT
0.05
Multi-Family Home
$470,000
11/07/25
9
4
1,885
71 East Main Street, Middletown, CT
0.30
Multi-Family Home
$210,000
11/26/25
9
5
3,110
40 Maple Place, Middletown, CT
0.22
Multi-Family Home
$300,000
01/14/26
7
2
2,346
37-39 Loveland Street, Middletown, CT
0.57
Multi-Family Home
$392,000
06/23/26
8
3
2,916
93 South Main Street, Middletown, CT
0.53
Multi-Family Home
$450,000
10/10/25
6
3
3,222
6 Omo Street, Middletown, CT
0.42
Multi-Family Home
$380,000
05/01/26
6
3
2,304
100 Saybrook Road, Middletown, CT
0.29
Multi-Family Home
$440,000
08/19/25
5
4
2,136
20 Maple Street, Middletown, CT
0.31
Multi-Family Home
$185,000
07/16/26
4
2
1,730
84 High Street, Middletown, CT
0.64
Multi-Family Home
$399,000
09/04/25
10
4
5,039
5 Maple Place, Middletown, CT
0.28
Multi-Family Home
$245,000
10/03/25
5
2
2,116

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 227 East Main Street.
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.
  • 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
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  • 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
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  • 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
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  • Richard D.
    "The is a walking/biking trail and a dog park. Nice clean areas safe for walking and locations for waste disposal."
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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!"
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  • Alnoor R.
    "Decent schools,safe, plenty of kid friendly space. Property taxes are high in CT. Job marked is tepid at best"
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  • Brian
    "great central location in CT, close to downtown and highways. quiet neighborhood, but properties very close together"
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  • 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."
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  • 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
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  • Leonardo V.
    "It is a very safe place to live..also shopping is close. The neighbors are friendly and very courteous.."
    0
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LGBTQ Local Legal Protections

Tanya Reyes, William Raveis Real Estate, (860) 538-4448
Agent Phone: (860) 538-4448
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
227 East Main Street, Middletown, CT 06457 is a 9 bedroom, 6 bathroom, 3,180 sqft multi-family built in 1991. This property is currently available for sale and was listed by Smart MLS on May 1, 2026. The MLS # for this home is MLS# 24171799.