108 Middlesex Ave

Chester, CT 06412

$675,000
Last Sold Price
4
Beds
4,056 Sq. Ft.
$166 / Sq. Ft.
4,056
Sq. Ft.
$166
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Closed 5/1/25
Closed 5/1/25
front view of a house with a yard

Description

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...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
  1. Listed by Trever R Smith • Chiarito Real Estate LLC
    P: (860)-876-7144 C: (860)-876-7144 treversmithre@gmail.com
  2. Listed by Al Chiarito • Chiarito Real Estate LLC
    P: (860)-227-2074 C: (860)-227-2074 al.chiarito@gmail.com

Property Details for 108 Middlesex Avenue

Basement Description
Full, Heated, Fully Finished, Garage Access, Cooled, Liveable Space, Full With Hatchway
Direct Waterfront
No
Garages Number
2
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Under House Garage
Swimming Pool
Yes
LISTING UPDATED: 05/01/2025 07:47 PM

Property Details for 108 Middlesex Avenue

StatusClosed
MLS #24076425
Days on Market35
Taxes$10,726 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built2002
Lot Size0.74 AC / 32,234 SF
CountyMiddlesex County
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Location

Listing Courtesy of Chiarito Real Estate LLC, Trever R Smith; Chiarito Real Estate LLC, Al Chiarito

Sold By Coldwell Banker Realty, Cortney Emshwiller-Swokla

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Building Information for 108 Middlesex Avenue

Stories-Year Built2002Building Size-Lot Size0.74 AC / 32,234 SF

Payment Calculator

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$4,184 per month

30 year fixed, 6.15% Interest

Principal and Interest

$3,290

Property Taxes

$894

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 108 Middlesex Avenue

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: 108 Middlesex Ave, Chester (Rte 154) GPS friendly. Close to the intersection of Water St and Middlesex Ave.
  • Elementary School: Chester
  • High School: Valley
  • Latitude: 41.407438
  • Longitude: -72.440282
  • Middle Jr High School: Region 4
  • Neighborhood Amenities: Library, Park, Playground/Tot Lot, Shopping/Mall
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2024-June 2025
  • Property Tax: $10,726
Interior and Exterior Features
Exterior Features
  • Exterior Features: Underground Utilities, Sidewalk, Shed, Deck, Gutters, Lighting, Underground Sprinkler
  • Pool Description: Above Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Storage Space, Finished, Walk-up
  • Cooling System: Split System
  • Heat Type: Baseboard, Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Cable - Pre-wired, Security System
  • Laundry Room Info: Lower Level, Main Level
  • Laundry Room Location: Basement and In Law
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 25.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 13.0
Room 2
  • Room Entry Order: 10
  • Room Features: Hardwood Floor
  • Room Length: 24.0
  • Room Level: Upper
  • Room Type: Great Room
  • Room Width: 16.0
Room 3
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 10.0
Room 4
  • Room Entry Order: 3
  • Room Features: Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 13.0
Room 5
  • Listing Key: 2EEBB87CFC75A79AE0631401100A4B06
  • Room Entry Order: 4
  • Room Features: Hardwood Floor
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.0
Room 6
  • Room Entry Order: 5
  • Room Features: Hardwood Floor
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Room 7
  • Room Entry Order: 6
  • Room Features: Granite Counters,Eating Space,Pantry,Tile Floor
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 12.0
Room 8
  • Room Entry Order: 7
  • Room Features: Wall/Wall Carpet,On 3rd Floor
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Great Room
  • Room Width: 16.0
Room 9
  • Listing Key: 2EEBB87CFC75A79AE0631401100A4B06
  • Room Entry Order: 8
  • Room Features: Laminate Floor
  • Room Length: 23.0
  • Room Level: Lower
  • Room Type: Family Room
  • Room Width: 12.0
Room 10
  • Room Entry Order: 9
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 12.0
Property
Property and Assessments
  • Color: Gray
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2002
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: First Floor, Separate Entry
  • In Law Apartment: Yes
  • Sq Ft Est Heated Below Grade: 936
  • Living Area SQFT Per Public Records: 3120
Lot Information
  • Lot Description: Sloping Lot
  • Parcel Number: 2313457
  • Sq Ft Est Heated Above Grade: 3120.0
  • Sq Ft Total: 4056.0
  • Zoning: R-5
Utilities
  • Energy Features: Active Solar, Generator, Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic, Upright Tank
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 108 Middlesex Avenue

DateEvent & SourcePriceAppreciation
May 1, 2025

Closed (Public Record)

Public Record #1557196669

$675,000—
DateEvent & SourcePrice
05/01/2025

Closed (Public Record)

Public Record #1557196669

$675,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 108 Middlesex Avenue

Taxable ValueLand$56,630Additions$382,060Total$438,690
Tax Record2024$11,880 ($990 / month)
Home Facts
Beds3Baths4.5Total Finished SqFt3,120 SqFtAbove Grade Finished SqFt3,120 SqFtUnfinished Basement SqFt864 SqFtStories2Lot Size32,234 SqFtStyleSingle Family ResidenceYear Built2002Year Renovated2009ZoningR-5CountyMIDDLESEXAPNCSTR M:10 B:244Fireplace TypeHas Fireplace

Schools near 108 Middlesex Avenue

This home is within Regional School District 04.
Rating
School
Type
Grades
Distance
Chester Elementary School
Public - K to 6
John Winthrop Middle School
Public - 6 to 8
Valley Regional High School
Public - 9 to 12
Mt Saint John
Private - 9 to 12
Rating
School
Distance
Chester Elementary School
PublicK to 6

John Winthrop Middle School
Public6 to 8

Valley Regional High School
Public9 to 12

Mt Saint John
Private9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Chiarito Real Estate LLC, Trever R Smith; Chiarito Real Estate LLC, Al Chiarito

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.