16 Middlesex Avenue, Chester, CT 06412
OFF MARKET

$561,600

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,963 sqft (on 1.06 acres)

16 Middlesex Avenue, Chester, CT 06412

Chester Center
Est. Refi. Payment $3,878/mo*
Refinance Your Home
Currently Off Market - Sold May 3, 2024 for $480,000

Home Value

Trulia Estimate
$562K
Since last month
Decreased$6K (-1%)
Since last year
Increased$42K (+8%)
Since last sale
Increased$82K (+17.1%)
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 +122% in the last 10 years
MonthEstimated value
2026
August 2026$562K
August 2026$562K
July 2026$568K
June 2026$583K
May 2026$582K
April 2026$567K
March 2026$565K
February 2026$541K
January 2026$544K
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
72 Winter Avenue, Deep River, CT
0.19
Single-Family Home
$320,000
08/26/26
3
3
1,836
16 Hickory Hill Drive, Chester, CT
0.35
Single-Family Home
$755,000
11/19/25
3
2.5
1,896
7 Hickory Hill Drive, Chester, CT
0.44
Single-Family Home
$549,000
03/24/26
3
2.5
2,202
9 Hickory Hill Drive, Chester, CT
0.41
Single-Family Home
$750,000
02/20/26
3
2.5
2,888
177 Union Street, Deep River, CT
0.69
Single-Family Home
$540,000
06/22/26
3
1.5
1,392
35 Maple Street, Chester, CT
0.54
Single-Family Home
$780,000
01/15/26
3
2
1,772
5 Mitchell Lane, Deep River, CT
0.19
Single-Family Home
$366,000
12/29/25
2
1.5
1,081
23 Spring Street, Chester, CT
0.68
Single-Family Home
$550,000
10/15/25
2
1.5
1,104
14 Maple Street, Chester, CT
0.56
Single-Family Home
$810,000
11/14/25
3
3.5
2,322

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
26 Middlesex Avenue, Chester, CT 06412
0.09
$481,400
4
1.5
1,496
Off Market
30 Middlesex Avenue, Chester, CT 06412
0.14
$420,900
2
1.5
1,362
Off Market
15 Gilbert Hill Road, Chester, CT 06412
0.17
$1,083,500
4
3
3,054
Off Market
9 Gilbert Hill Road, Chester, CT 06412
0.19
$465,100
2
1.5
2,008
Off Market
25 Gilbert Hill Road, Chester, CT 06412
0.19
$1,229,100
4
4.5
3,351
Off Market
32 Winter Avenue, Deep River, CT 06417
0.18
$390,800
4
2
1,598
Off Market
17+21 Winter Avenue, Deep River, CT 06417
0.19
$289,900
3
2.5
1,061
For Sale
72 Winter Avenue, Deep River, CT 06417
0.19
$320,000
3
3
1,836
Recently Sold
5 Mitchell Lane, Deep River, CT 06417
0.19
$366,000
2
1.5
1,081
Recently Sold
5 Mitchell Terrace, Deep River, CT 06417
0.19
$417,200
3
1.5
1,184
Off Market
38 Main Street, Deep River, CT 06417
0.25
$625,000
4
3
2,560
For Sale

Local Information

  • Map ViewExplore the area around 16 Middlesex Avenue.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1945
1.06 acre lot
1,963 sqft
$286/sqft
Open Parking

About this House

Welcome to the timeless elegance of this Cape style residence with seasonal water views minutes from charming Chester village. Built in 1945, this meticulously maintained home offers 3 bedrooms and 2 full bathrooms across 1,500+ square feet of living space. The heart of the home is the main level, featuring a well-appointed kitchen with granite counters and an island, a dining room bathed in natural light, and a spacious living room with a fireplace, perfect for cozy gatherings. The upper level hosts the primary bedroom with built-ins and a walk-in closet, an additional bedroom, and a full bath with a whirlpool tub. Another generously sized bedroom and a full bath with a stall shower grace the main level. The lower level offers a versatile family/play room, guest bedroom or home office and a convenient laundry room. Embrace the serenity of the 1.06-acre property, perfect for outdoor activities and gardening or simply entertaining on the 2 tiered deck. Enjoy the convenience of nearby amenities such as great restaurants, shopping, a golf course, lake, library, medical facilities, and parks. Schedule your visit to experience this beautiful home in one of CTs most charming towns and envision a lifestyle that seamlessly blends comfort, style, and tranquility. Welcome to your new home!
16 Middlesex Avenue, Chester, CT 06412 is a 3 bedroom, 2 bathroom, 1,963 sqft single-family home in Chester Center, built in 1945. It last sold for $480,000 on May 3, 2024 (4% below the $499,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $561,600, with a rent estimate of $3,405/month.
Last check for updates: about 3 hours ago
Listed by Chloe N. White, (860) 302-7717
KW Legacy Partners, (860) 313-0700
Bought with: Lewis E. Jump III, (860) 910-8136, RE/MAX One, (860) 444-7362
Source: Smart MLS, MLS#170609851

Home Details for 16 Middlesex Avenue

Interior Features

Interior Details
Basement: Full,Storage SpaceNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Kitchen, Living Room, Office, Rec Play Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1963 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Lower LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Oil,PropaneHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PorchFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Driveway,Paved
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 1511 Square FeetFinished Area (below surface): 452 Square Feet

Property Information

Year Built
Year Built: 1945
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: Aluminum SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 941247

Price & Status

Price
List Price: $499,900
Status Change & Dates
Off Market Date: Fri Dec 15 2023Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

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

Agent Information

Buyer Agent
Buyer Company Name: Next Level Team of RE/MAX One

Building

Building Area
Building Area: 1963 Square Feet

Community

Community Features: Golf, Lake, Library, Medical Facilities, Park

HOA

No HOA

Lot Information

Lot Area: 1.06 Acres

Miscellaneous

BasementMls Number: 170609851Attic: Walk-upAbove Grade Unfinished Area: 1511

Additional Information

GolfLakeLibraryMedical FacilitiesPark

Price and Tax history

DateEventPrice
May 3, 2024
Source: Smart MLS #170609851
Sold
$480,000
Jan 29, 2024
Source: Smart MLS #170609851
Pending
$499,900
Dec 18, 2023
Source: Smart MLS #170609851
Contingent
$499,900
Dec 6, 2023
Source: Smart MLS #170609851
PriceChange
$499,900
Price decreased by 3%
Nov 30, 2023
Source: Smart MLS #170609851
Listed For Sale
$515,000

Market trends in Chester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
12
4MoM

Around this home

Neighborhood Overview

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

LGBTQ Local Legal Protections

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.

Frequently asked questions about 16 Middlesex Avenue

  • What is 16 Middlesex Avenue estimated to be worth?
    Trulia's estimated value for 16 Middlesex Avenue in Chester, CT is $561,600.
  • What is the price history for 16 Middlesex Avenue?
    16 Middlesex Avenue in Chester, CT last sold for $480,000 in May 2024.
  • 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 16 Middlesex Avenue?
    The closest schools to 16 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 16 Middlesex Avenue have air conditioning?
    Yes, 16 Middlesex Avenue in Chester, CT has air conditioning.
  • Does 16 Middlesex Avenue have laundry facilities?
    Yes, 16 Middlesex Avenue in Chester, CT has in-unit laundry.

Apartments for Rent

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Off Market Homes Near 16 Middlesex Avenue

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