96 Middlesex Avenue, Chester, CT 06412
OFF MARKET

$1,406,800

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,153 sqft (on 6.26 acres)

96 Middlesex Avenue, Chester, CT 06412

Chester Center
Est. Refi. Payment $9,564/mo*
Refinance Your Home
Currently Off Market - Sold Jan 31, 2025 for $1,300,000

Home Value

Trulia Estimate
$1.41M
Since last month
Decreased$24K (-1.7%)
Since last year
Increased$83K (+6.2%)
Since last sale
Increased$111K (+8.5%)
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 +221% in the last 10 years
MonthEstimated value
2026
August 2026$1.41M
August 2026$1.41M
July 2026$1.44M
June 2026$1.4M
May 2026$1.39M
April 2026$1.41M
March 2026$1.42M
February 2026$1.4M
January 2026$1.38M
2025
2024
2023
2022
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
7 Old Depot Road, Chester, CT
0.17
Single-Family Home
$975,000
11/17/25
4
2.5
3,149
47 Ferry Road, Chester, CT
0.94
Single-Family Home
$1,275,000
12/12/25
3
3
2,664
1 Ferry Road, Chester, CT
0.44
Single-Family Home
$635,000
04/30/26
3
3
2,752
9 Hickory Hill Drive, Chester, CT
0.52
Single-Family Home
$750,000
02/20/26
3
2.5
2,888
14 Maple Street, Chester, CT
0.55
Single-Family Home
$810,000
11/14/25
3
3.5
2,322
131 Middlesex Avenue, Chester, CT
0.28
Single-Family Home
$530,000
02/26/26
3
2.5
1,664
16 Hickory Hill Drive, Chester, CT
0.56
Single-Family Home
$755,000
11/19/25
3
2.5
1,896
7 Hickory Hill Drive, Chester, CT
0.54
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
0.09
-
-
-
-
Off Market
108 Middlesex Avenue, Chester, CT 06412
0.11
$735,200
4
4.5
4,056
Off Market
79 Middlesex Avenue, Chester, CT 06412
0.14
$410,000
2
1
1,470
Recently Sold
7 Old Depot Road, Chester, CT 06412
0.17
$975,000
4
2.5
3,149
Recently Sold
41 Railroad Avenue, Chester, CT 06412
0.20
$458,000
2
1
1,771
Off Market
8 School Lane, Chester, CT 06412
0.27
$538,400
3
2
1,512
Off Market
42 Railroad Avenue, Chester, CT 06412
0.25
$540,600
4
2
2,092
Off Market
132 Middlesex Avenue, Chester, CT 06412
0.28
$328,700
2
1
1,001
Off Market
131 Middlesex Avenue, Chester, CT 06412
0.28
$530,000
3
2.5
1,664
Recently Sold
9 School Lane, Chester, CT 06412
0.30
$519,800
3
1.5
1,388
Off Market
34 Story Hill Road, Chester, CT 06412
0.31
$346,500
2
1
1,081
Off Market

Local Information

  • Map ViewExplore the area around 96 Middlesex Avenue.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1830
6.26 acre lot
3,153 sqft
$446/sqft
2 Car Garage

About this House

Steeped in history, awash in modern amenities and conveniences, this 4 bed (2 en suite), 3 1/2 bath converted barn sits on over six acres just a spit from the Connecticut River and the quintessential town of Chester. The current homeowner's goal was to gently nudge the 1830s cider mill into this century with thought, care, and charm salvaging and repurposing as many original features as feasible. The transformation included removal of randomly erected partition walls throughout, and reworking the floor plan. Original wall planks were unearthed, hand sawn chestnut flooring was restored, and extra planks were used to create mantles for the 2 fireplaces. The live-edge sheathing in the ceiling was preserved giving the space simultaneously a sense of grandiosity and warmth. The resulting home is an inviting and comfortable retreat for a few or a fabulous entertaining space for many. From the oversized deck complete with outdoor kitchen, look out over the vast field and watch the wildlife including foxes, deer, bobcats, coyotes, American Kestrels, goldfinch and eastern bluebirds, possums, raccoons and more. A few apple trees remain, the fields slope and undulate untouched by time. Enjoy a cup of coffee or a glass of wine in the gazebo or al fresco next to 'frog pond' or as you meander along the path around the pasture. The fully updated estate with new HVAC, roof, solar, kitchen, bathrooms, outdoor shower, electrical, plumbing and septic system is ready for your vision; do you desire a pool, family compound, gentleman's farm, tennis court, animal sanctuary....? Your dreams are calling and this property can make them a reality. Land is sub-dividable, preliminary plans available.
96 Middlesex Avenue, Chester, CT 06412 is a 4 bedroom, 4 bathroom, 3,153 sqft single-family home in Chester Center, built in 1830. It last sold for $1,300,000 on Jan 31, 2025 (5% below the $1,375,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,406,800, with a rent estimate of $5,030/month.
Last check for updates: about 2 hours ago
Listed by Susan A. Malan, (617) 645-4392
William Pitt Sotheby's Int'l, (860) 767-7488
Bought with: Matt DeLucia, (860) 966-1617, William Pitt Sotheby's Int'l, (860) 777-1800
Source: Smart MLS, MLS#24038493

Home Details for 96 Middlesex Avenue

Interior Features

Interior Details
Basement: Full,Partially FinishedNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room, Sun Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3153 Square Feet
Appliances & Utilities
Appliances: Gas Cooktop, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Electric,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Porch, Wrap Around, Deck, PatioOther Structures: GazeboExterior: GardenFoundation: StoneGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Off Street,Driveway,Private
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Farm & Range
Horse Amenities: PaddocksAllowed to Raise Horses
Finished Area
Finished Area (above surface): 3153 Square Feet

Property Information

Year Built
Year Built: 1830
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Antique,Barn
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 941342

Price & Status

Price
List Price: $1,375,000
Status Change & Dates
Off Market Date: Mon Jan 20 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Chester
School Information
Elementary School: ChesterHigh School: Valley

Building

Building Area
Building Area: 3153 Square Feet

Community

Community Features: Basketball Court, Lake, Library, Medical Facilities, Park, Playground, Public Rec Facilities
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 6.26 Acres

Miscellaneous

BasementMls Number: 24038493Attic: NoneAbove Grade Unfinished Area: 3153

Additional Information

Basketball CourtLakeLibraryMedical FacilitiesParkPlaygroundPublic Rec Facilities

Price and Tax history

DateEventPrice
Jan 31, 2025
Source: Smart MLS #24038493
Sold
$1,300,000
Jan 24, 2025
Source: Smart MLS #24038493
Pending
$1,375,000
Dec 11, 2024
Source: Smart MLS #24038493
PriceChange
$1,375,000
Price decreased by 1%
Aug 14, 2024
Source: Smart MLS #24038493
Listed For Sale
$1,395,000
Apr 12, 2022
Source: Smart MLS #170342243
Sold
$460,000

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.

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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.

Frequently asked questions about 96 Middlesex Avenue

  • What is 96 Middlesex Avenue estimated to be worth?
    Trulia's estimated value for 96 Middlesex Avenue in Chester, CT is $1,406,800.
  • What is the price history for 96 Middlesex Avenue?
    96 Middlesex Avenue in Chester, CT last sold for $1,300,000 in January 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 96 Middlesex Avenue?
    The closest schools to 96 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 96 Middlesex Avenue have air conditioning?
    Yes, 96 Middlesex Avenue in Chester, CT has air conditioning.
  • Does 96 Middlesex Avenue have laundry facilities?
    Yes, 96 Middlesex Avenue in Chester, CT has in-unit laundry.

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