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

$649,900

Original price: $749,900
  • 9 Beds
  • 4.5 Baths
  • 3,180 sqft

227 East Main Street, Middletown, CT 06457

Est. Mortgage $4,581/mo*
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Home Highlights

Multi-Family
Built in 1991
$204/sqft
3 Car Garage

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

Exceptional 3-Unit Mixed-Use Investment Opportunity A rare opportunity to own a well-maintained three-unit property offering townhouse-style living, private garages, excellent parking, and strong income-producing potential in the heart of Middletown. 227 East Main Street is an attractive investment opportunity for both seasoned investors and owner-occupants looking to build equity while generating rental income. The property features three spacious townhouse-style residential units, each offering 3 bedrooms, 1 full bathroom, and 1 half bathroom. The desirable layouts include bright, comfortable living spaces and eat-in kitchens, creating a residential feel that appeals to a broad range of tenants. One of the property's most compelling features is the private under-building garage for each unit, complete with direct access. This added convenience provides residents with the feel and functionality of a single-family home-an especially desirable feature in a multi-family property. Additional highlights include separate utilities, hardwood flooring, abundant natural light, basement storage, Washer dryer hook-ups in each unit, ample off-street parking, and a rear driveway providing convenient access behind the building. Separate utilities offer practical advantages for ownership and day-to-day management. Situated near downtown Middletown, Wesleyan University, Middlesex Health, shopping, dining, parks, and major commuter routes. Property being sold As Is. Agent owner related.
Last check for updates: about 11 hours ago
Listing courtesy of Tanya Reyes, (860) 538-4448
William Raveis Real Estate, (860) 538-4448
Source: Smart MLS, MLS#24199960
Also Listed on Smart MLS.

Home Details for 227 East Main Street

Interior Features

Interior Details
Basement: PartialNumber 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: 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: ShingleFoundation: 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: 32

Property Information

Year Built
Year Built: 1991
Property Type / Style
Property Type: Residential IncomeProperty Subtype: Multi FamilyArchitecture: 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: $649,900Price Per Sqft: $204
Status Change & Dates
Possession Timing: Tenants

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: 24199960

Building

Building Area
Building Area: 3180 Square Feet

Community

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

HOA

No HOA

Lot Information

Lot Area: 7405.2 sqft

Miscellaneous

BasementMls Number: 24199960Attic: NoneAttribution Contact: (860) 538-4448Above Grade Unfinished Area: 3180

Additional Information

LibraryMedical FacilitiesParkPublic Rec FacilitiesNear Public TransportShopping/Mall

Around this home

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
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  • 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
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  • 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
    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
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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!"
    0
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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"
    0
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  • Brian
    "great central location in CT, close to downtown and highways. quiet neighborhood, but properties very close together"
    0
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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."
    0
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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
    Flag
  • Leonardo V.
    "It is a very safe place to live..also shopping is close. The neighbors are friendly and very courteous.."
    0
    Flag

Market trends in Middletown

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$351K
$21.67KMoM
Sale-to-List Price
103.6%
0.1%MoM
Price per sq ft
$236
$5MoM
Available listings
85
7MoM

Home Value

Trulia Estimate
$631K
Since last month
Decreased$12K (-1.8%)
Since last year
Increased$101K (+19.1%)
Since last sale
Increased$461K (+271.3%)
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 +187% in the last 10 years
MonthEstimated value
2026
September 2026$631K
August 2026$643K
July 2026$714K
June 2026$718K
May 2026$821K
April 2026$530K
March 2026$535K
February 2026$491K
January 2026$504K
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
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
8
4
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
20 Maple Street, Middletown, CT
0.31
Multi-Family Home
$185,000
07/16/26
4
2
1,730
5 Maple Place, Middletown, CT
0.28
Multi-Family Home
$245,000
10/03/25
5
2
2,116
117-119 South Main Street, Middletown, CT
0.52
Multi-Family Home
$350,000
04/29/26
6
2
2,555
102 Main St Extension, Middletown, CT
0.29
Multi-Family Home
$405,000
12/18/25
4
2
1,518

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
204-206 East Main Street, Middletown, CT 06457
0.05
$258,900
3
2
1,578
Off Market
203 East Main Street, Middletown, CT 06457
0.05
$372,400
9
4
1,885
Off Market
15 Wall Street, Middletown, CT 06457
0.12
$359,700
4
2
2,054
Off Market
35 Wall Street, Middletown, CT 06457
0.11
$396,600
3
2.5
1,329
Off Market
10 Silver Street, Middletown, CT 06457
0.09
$270,000
4
1.5
1,415
Recently Sold
5 Wall Street, Middletown, CT 06457
0.14
$268,000
2
1.5
1,010
Recently Sold
21 Saybrook Road, Middletown, CT 06457
0.17
$326,400
Studio
-
2,795
Off Market
4 Ridge Road, Portland, CT 06480
0.14
$552,000
3
2.5
2,250
Off Market
23 Silver Street, Middletown, CT 06457
0.16
$493,800
5
2
2,262
Off Market
205 Main Street Extension, Middletown, CT 06457
0.15
$283,000
2
2
1,264
Off Market
4 Crown Street, Middletown, CT 06457
0.17
$300,000
2
1
936
Recently Sold

Price and Tax history

DateEventPrice
Aug 17, 2026
Source: Smart MLS #24199960
PriceChange
$649,900
Price decreased by 13%
Jun 25, 2026
Source: Smart MLS #24171799
PriceChange
$749,900
Price decreased by 6%
May 31, 2026
Source: Smart MLS #24171799
PriceChange
$799,900
Price decreased by 6%
May 1, 2026
Source: Smart MLS #24171799
Listed For Sale
$850,000
Jun 19, 1992
Source: N/A
Sold
$170,000

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.

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Frequently asked questions about 227 East Main Street

  • What is the estimated monthly payment for 227 East Main Street?
    Based on a $649,900 list price with 20% down at today's rates, the estimated monthly payment for 227 East Main Street in Middletown, CT is approximately $4,651 (about $3,547 principal & interest, $1,029 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 227 East Main Street compare to homes in Middletown?
    227 East Main Street in Middletown, CT is listed at $649,900, about 85% above the $351K median sale price in Middletown.
  • What do residents say about Middletown?
    Residents describe Middletown, CT as dog-friendly, easy to park in, and pedestrian-friendly. See homes for sale in Middletown, CT.
  • What are the closest schools to 227 East Main Street?
    The closest schools to 227 East Main Street in Middletown, CT are Beman Middle School (rated 4/10), Farm Hill School (Pre-K/Elementary, rated 5/10), Middletown High School (rated 4/10).
  • Does 227 East Main Street have air conditioning?
    Yes, 227 East Main Street in Middletown, CT has air conditioning.
  • Does 227 East Main Street have laundry facilities?
    Yes, 227 East Main Street in Middletown, CT has laundry facilities.
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 Aug 17, 2026. The MLS # for this home is MLS# 24199960.