108 Middlesex Avenue, Chester, CT 06412
OFF MARKET

$746,200

Trulia Estimate
  • 4 Beds
  • 4.5 Baths
  • 4,056 sqft (on 0.74 acres)

108 Middlesex Avenue, Chester, CT 06412

Chester Center
Est. Refi. Payment $5,180/mo*
Refinance Your Home
Currently Off Market - Sold May 1, 2025 for $675,000

Home Value

Trulia Estimate
$746K
Since last month
Increased$7K (+1%)
Since last year
Increased$58K (+8.4%)
Since last sale
Increased$68K (+10%)
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 +32% in the last 10 years
MonthEstimated value
2026
September 2026$743K
August 2026$735K
July 2026$741K
June 2026$723K
May 2026$716K
April 2026$725K
March 2026$730K
February 2026$718K
January 2026$707K
2025
2024

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
131 Middlesex Avenue, Chester, CT
0.18
Single-Family Home
$530,000
02/26/26
3
2.5
1,664
1 Ferry Road, Chester, CT
0.33
Single-Family Home
$635,000
04/30/26
3
3
2,752
7 Old Depot Road, Chester, CT
0.28
Single-Family Home
$975,000
11/17/25
4
2.5
3,149
14 Maple Street, Chester, CT
0.63
Single-Family Home
$810,000
11/14/25
3
3.5
2,322
9 Hickory Hill Drive, Chester, CT
0.62
Single-Family Home
$750,000
02/20/26
3
2.5
2,888
14 Ferry Road, Chester, CT
0.48
Single-Family Home
$420,000
09/24/25
4
1.5
2,025
6 Jagger Lane, Chester, CT
0.67
Single-Family Home
$805,000
09/01/26
2
2.5
2,428
7 Hickory Hill Drive, Chester, CT
0.63
Single-Family Home
$549,000
03/24/26
3
2.5
2,202

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
109A Middlesex Avenue, Chester, CT 06412
0.05
-
-
-
-
Off Market
96 Middlesex Avenue, Chester, CT 06412
0.11
$1,423,800
4
3.5
3,153
Off Market
41 Railroad Avenue, Chester, CT 06412
0.21
$460,400
2
1
1,771
Off Market
132 Middlesex Avenue, Chester, CT 06412
0.18
$331,700
2
1
1,001
Off Market
131 Middlesex Avenue, Chester, CT 06412
0.18
$530,000
3
2.5
1,664
Recently Sold
79 Middlesex Avenue, Chester, CT 06412
0.23
$410,000
2
1
1,470
Recently Sold
135 Middlesex Avenue, Chester, CT 06412
0.20
$475,000
3
2
1,188
For Sale
42 Railroad Avenue, Chester, CT 06412
0.27
$545,400
4
2
2,092
Off Market
7 Old Depot Road, Chester, CT 06412
0.28
$1,049,200
4
2.5
3,149
Off Market
34 Story Hill Road, Chester, CT 06412
0.27
$354,900
2
1
1,081
Off Market
90 Water Street, Chester, CT 06412
0.27
$269,900
1
1
1,034
For Sale

Local Information

  • Map ViewExplore the area around 108 Middlesex Avenue.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2002
0.74 acre lot
4,056 sqft
$184/sqft
2 Car Garage

About this House

What's unique:Cozy fireplacePrimary suiteTwo car garageCustom wine rackUnderground sprinklersShed with power
Welcome to 108 Middlesex Ave. A multi family Colonial income producing property in the heart of Chester! The home was built in 2002, and in 2006 an attached accessory dwelling unit / inlaw apartment was added and is now occupied at $2,000 a month. The main house features a bright and inviting layout with hardwood floors, a cozy fireplace in the living room and sliders from the dining room out to the deck. A well-appointed kitchen has a pantry, granite countertops, stainless steel appliances, a custom wine rack and tile floor. There is also a nice half bath on this main level. Upstairs, the primary suite boasts a walk-in closet and a full bath, accompanied by two additional bedrooms and a full bathroom in the hallway. There is also a walk up storage attic and finished area. The lower level is mint and fully finished and walks out to the two car garage. The private rentable ADU has one bedroom, a full bathroom, living room dining combo, full kitchen, full laundry, nice walk up additional space and separate electric meter. Outside, enjoy the expansive backyard with a deck, an above-ground (heated??) pool, a shed with power for extra storage, and underground sprinklers. Additional highlights include EV charger, Generac generator (leased), and solar panels (owned). Located just minutes from Chester's vibrant town center, shopping, and dining, this home offers the perfect blend of comfort and convenience. Don't miss this incredible opportunity. Also listed under mls#24082679
108 Middlesex Avenue, Chester, CT 06412 is a 4 bedroom, 5 bathroom, 4,056 sqft single-family home in Chester Center, built in 2002. It last sold for $675,000 on May 1, 2025 (3% below the $699,000 asking price). More recently, it was listed as a rental in October 2024 with an asking price of $4,500 per month. That rental listing was removed on December 19, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $746,200, with a rent estimate of $5,800/month.
Last check for updates: about 3 hours ago
Listed by Trever R. Smith, (860) 876-7144
Chiarito Real Estate LLC, (860) 227-2074
Al Chiarito, (860) 227-2074
Chiarito Real Estate LLC, (860) 227-2074
Bought with: Cortney Emshwiller-Swokla, (860) 501-0232, Coldwell Banker Realty
Source: Smart MLS, MLS#24076425

Home Details for 108 Middlesex Avenue

Interior Features

Interior Details
Basement: Full,Heated,Finished,Garage Access,Cooled,Liveable SpaceNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Great Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4056 Square Feet
Appliances & Utilities
Utilities: Underground UtilitiesAppliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Lower Level,Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,OilHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckOther Structures: Shed(s)Exterior: Sidewalk, Rain Gutters, Lighting, Underground SprinklerFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Pool
Pool: Above GroundPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 3120 Square FeetFinished Area (below surface): 936 Square Feet

Property Information

Year Built
Year Built: 2002
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 2313457

Price & Status

Price
List Price: $699,000
Status Change & Dates
Off Market Date: Sun Mar 30 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Chester
School Information
Elementary School: ChesterJr High / Middle School: Region 4High School: Valley

Building

Building Area
Building Area: 4056 Square Feet

Community

Community Features: Library, Park, Playground, Shopping/Mall
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.74 acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24076425Attic: Storage, Finished, Walk-upAbove Grade Unfinished Area: 3120

Additional Information

LibraryParkPlaygroundShopping/Mall

Price and Tax history

DateEventPrice
May 1, 2025
Source: Smart MLS #24076425
Sold
$675,000
Apr 29, 2025
Source: Smart MLS #24082679
Pending
$699,000
Feb 25, 2025
Source: Smart MLS #24076425
Listed For Sale
$699,000
Dec 19, 2024
Source: Smart MLS #24055216
ListingRemoved
$3,900
Dec 11, 2024
Source: Smart MLS #24040512
ListingRemoved
$699,000

Market trends in Chester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
9
3MoM

Around this home

Neighborhood Overview

Chester Center
See Local Highlights
Neighborhood stats provided by third party data sources.

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Frequently asked questions about 108 Middlesex Avenue

  • What is 108 Middlesex Avenue estimated to be worth?
    Trulia's estimated value for 108 Middlesex Avenue in Chester, CT is $746,200.
  • What is the price history for 108 Middlesex Avenue?
    108 Middlesex Avenue in Chester, CT last sold for $675,000 in May 2025.
  • Is Chester a buyer's or seller's market?
    Chester is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 108 Middlesex Avenue?
    The closest schools to 108 Middlesex Avenue in Chester, CT are Chester Elementary School (Pre-K, rated 7/10), John Winthrop Middle School (rated 4/10), Valley Regional High School (rated 7/10).
  • Does 108 Middlesex Avenue have air conditioning?
    Yes, 108 Middlesex Avenue in Chester, CT has air conditioning.
  • Does 108 Middlesex Avenue have a pool?
    Yes, 108 Middlesex Avenue in Chester, CT has a pool.

Apartments for Rent

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