85 Chestnut Street, Middletown, CT 06457
OFF MARKET

85 Chestnut Street
Middletown, CT 06457

  • 6 Beds
  • 2 Baths
  • 2,636 sqft (on 0.28 acres)

$398,700

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $2,766/mo*
Refinance Your Home

$398,700

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $2,766/mo*
Refinance Your Home
6 Beds
2 Baths
2,636 sqft
(on 0.28 acres)

Local Information

  • Map ViewExplore the area around 85 Chestnut Street.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1900
Lot Size
0.28 acres
Living Area
2,636 sqft
Price/Sqft
$151
Parking
Garage

About this House

Welcome to this charming and well-maintained 2-family home, nestled in a desirable neighborhood! Light and bright with ample living space and plenty of potential to make it your own! The first floor features 3 bedrooms, 1 full bath & the second floor boasts 3 bedrooms, 1 full bath, and a bonus room that could be an office, den, or exercise room. A detached 2-car garage and a lush yard for you to enjoy in every season! The home's prime location is mere steps to Main Street and offers easy access to public transportation, schools, shopping, and dining, ensuring everything you need is within reach. Perfect for investors seeking consistent rental income as both units could easily rent for at least $1750 each, OR those looking for a comfortable multi-generational living arrangement.
85 Chestnut Street, Middletown, CT 06457 is a 6 bedroom, 2 bathroom, 2,636 sqft multi-family built in 1900. It last sold for $375,000 on May 16, 2025 (14% above the $329,900 asking price). It is currently off market. The Trulia Estimate is $398,700, with a rent estimate of $1,944/month.

Home Details for 85 Chestnut Street

Interior Features

Interior Details
Basement: Full,Shared Basement,Storage SpaceNumber of Rooms: 10
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2636 Square Feet
Appliances & Utilities
Appliances: Water Heater
Heating & Cooling
Heating: Steam,OilHas CoolingAir Conditioning: Ceiling Fan(s),Window Unit(s)Has HeatingHeating Fuel: Steam
Fireplace & Spa
No Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckFoundation: Concrete Perimeter, MasonryNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Detached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2636 Square Feet

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Residential IncomeProperty Subtype: Multi FamilyArchitecture: Units on different Floors
Building
Construction Materials: Aluminum SidingNot a New Construction
Property Information
Parcel Number: 1005455

Price & Status

Price
List Price: $329,900
Status Change & Dates
Off Market Date: Fri Apr 04 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Middletown
School Information
Elementary School: Per Board of EdHigh School: Middletown

Agent Information

Buyer Agent
Buyer Company Name: J. Boswell Team at LPT Realty

Building

Building Area
Building Area: 2636 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.28 acres

Miscellaneous

BasementMls Number: 24083669Attic: Access Via HatchAbove Grade Unfinished Area: 2636
Last check for updates: about 9 hours ago
Listed by Maxwell Castrogiovanni, (860) 302-8394
eXp Realty, (866) 828-3951
Bought with: Jessica Boswell, (860) 357-0704, LPT Realty, (877) 366-2213
Co-Buyer's Agent: Co-Buyer Agent: Maria Fiasconaro, (959) 283-0012, LPT Realty, (877) 366-2213
Source: Smart MLS, MLS#24083669

Price History for 85 Chestnut Street

DatePriceEventSource
05/16/2025$375,000Sold
Smart MLS #24083669
04/06/2025$329,900PendingSmart MLS #24083669
04/22/2019$225,000Sold
N/A
06/24/2008$275,000Sold
N/A
10/15/2007$153,000Sold
N/A
09/28/1998$65,000Sold
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$6,679
Assessment$180,470
Home facts updated by county records

Comparable Sales for 85 Chestnut Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5 Maple Place, Middletown, CT
0.12
Multi-Family Home
$245,000
10/03/25
5
2
2,116
40 Maple Place, Middletown, CT
0.08
Multi-Family Home
$300,000
01/14/26
7
2
2,346
6 Omo Street, Middletown, CT
0.23
Multi-Family Home
$380,000
05/01/26
6
3
2,304
121 Saybrook Road, Middletown, CT
0.46
Multi-Family Home
$385,000
07/07/26
5
2
2,243
20 Maple Street, Middletown, CT
0.13
Multi-Family Home
$185,000
07/16/26
4
2
1,730
102 Main St Extension, Middletown, CT
0.25
Multi-Family Home
$405,000
12/18/25
4
2
1,518
117-119 South Main Street, Middletown, CT
0.54
Multi-Family Home
$350,000
04/29/26
6
2
2,555
71 East Main Street, Middletown, CT
0.22
Multi-Family Home
$210,000
11/26/25
9
5
3,110
203 East Main Street, Middletown, CT
0.17
Multi-Family Home
$470,000
11/07/25
9
4
1,885

Nearby homes

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Assigned Schools

These are the assigned schools for 85 Chestnut 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.
  • 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
  • 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
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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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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 85 Chestnut Street

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Off Market Homes Near 85 Chestnut 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.