581 High Street, Middletown, CT 06457
SOLD
FEB 18, 2026

581 High Street
Middletown, CT 06457

  • 3 Beds
  • 1 Bath
  • 1,057 sqft

$285,000

Last Sold: Feb 18, 2026
2% over list $280K
$270/sqft

$285,000

Last Sold: Feb 18, 2026
2% over list $280K
$270/sqft
3 Beds
1 Bath
1,057 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Welcome to this updated, energy-efficient home, located just minutes from Wesleyan University, downtown Middletown, restaurants, shopping, and the riverfront. With solar panels, a newer kitchen, and a surprisingly deep backyard, this property blends convenience, modern comfort, and value. The first floor offers a bright living room with hardwood floors, a large eat-in kitchen with white cabinetry, stainless appliances, ample counter space, and first-floor laundry, plus a generously sized primary bedroom suite for desirable one-level living. Upstairs are two additional bedrooms with great natural light, and the clean, divided basement provides excellent storage and workshop potential. Outside, the deep lot offers rare usable yard space-ideal for pets, gardening, entertaining, or future expansion-along with a storage shed and off-street parking. Move-in ready with low utility costs thanks to solar, this home is a fantastic opportunity for first-time buyers, downsizers, or anyone seeking a centrally located home with updates and charm.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from February 18, 2026

Home Highlights

Parking
Open Parking
Outdoor
Porch
A/C
Heating & Cooling
HOA
None
Price/Sqft
$270/sqft
Listed
175 days ago

Home Details for 581 High Street

Interior Features

Interior Details
Basement: PartialNumber of Rooms: 5Types of Rooms: Master Bedroom, Bedroom, Master Bathroom, Bathroom, Kitchen, Living Room, Sun Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 1057 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, DryerDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,OilHas CoolingAir Conditioning: Ceiling Fan(s),Window Unit(s)Has HeatingHeating Fuel: Hot Water
Fireplace & Spa
No Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Screened, PorchOther Structures: Shed(s)Foundation: StoneNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 1Parking: On Street,Off Street,Driveway
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1057 Square Feet

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Other
Building
Construction Materials: Aluminum SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1015711

Price & Status

Price
List Price: $280,000Price Per Sqft: $270/sqft
Status Change & Dates
Off Market Date: Sun Feb 01 2026Possession Timing: Immediate

Active Status

MLS Status: Closed

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

Building

Building Area
Building Area: 1057 Square Feet

Community

Community Features: Library, Medical Facilities, Park, Near Public Transport

HOA

No HOA

Lot Information

Lot Area: 6534 sqft

Miscellaneous

BasementMls Number: 24144541Attic: NoneAttribution Contact: (203) 631-3499Above Grade Unfinished Area: 1057

Additional Information

LibraryMedical FacilitiesParkNear Public Transport
Last check for updates: about 4 hours ago
Listed by Abby Breau, (203) 631-3499
New England Prestige Realty, (860) 652-8495
Bought with: Anower Hossain, (860) 992-4979, Executive Real Estate Inc., (860) 633-8800
Source: Smart MLS, MLS#24144541

Price History for 581 High Street

DatePriceEventSource
02/18/2026$285,000Sold
Smart MLS #24144541
02/18/2026$280,000PendingSmart MLS #24144541
01/02/2026$280,000PriceChange
Smart MLS #24144541
12/11/2025$285,000Listed For SaleSmart MLS #24144541
09/30/2022$260,000Sold
N/A
04/29/2022$125,000Sold
Smart MLS #170480571
04/08/2022$114,900Listed For SaleSmart MLS #170480571
04/29/1998$65,000Sold
N/A

Market trends in Middletown

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$281K
$23.67KMoM
Sale-to-List Price
—
Price per sq ft
$216
$0MoM
Available listings
65
4MoM
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Property Tax and Assessment

Year2025
Tax$6,853
Assessment$176,170
Home facts updated by county records

Comparable Sales for 581 High Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
21 Rome Avenue, Middletown, CT
0.19
Single-Family Home
$246,000
01/06/26
3
1
1,344
46 Johnson Street, Middletown, CT
0.06
Single-Family Home
$319,900
09/24/25
3
2
1,480
18 Bacon Avenue, Middletown, CT
0.25
Single-Family Home
$189,909
10/16/25
2
1
1,140
20 Prospect Street, Middletown, CT
0.47
Single-Family Home
$301,000
01/16/26
3
1
1,210
177 Pearl Street, Middletown, CT
0.33
Single-Family Home
$272,500
04/14/26
3
1
1,186
11 Columbus Avenue, Middletown, CT
0.26
Single-Family Home
$305,000
01/12/26
4
2
1,773
21 Portland Street, Middletown, CT
0.35
Single-Family Home
$185,000
08/29/25
2
1
791
3 Prospect Place, Middletown, CT
0.19
Single-Family Home
$150,000
10/21/25
2
1
735
129 Newfield Street, Middletown, CT
0.61
Single-Family Home
$275,000
07/03/25
3
1.5
1,075

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Assigned Schools

These are the assigned schools for 581 High 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 386 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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Off Market Homes Near 581 High Street

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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.

Homes for rent near 581 High Street

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581 High Street, Middletown, CT 06457 is a 3 bedroom, 1 bathroom, 1,057 sqft single-family home built in 1900. This property is not currently available for sale. 581 High Street was last sold on Feb 18, 2026 for $285,000 (2% higher than the asking price of $280,000). The current Trulia Estimate for 581 High Street is $288,500.