Off market jan 2025 for $1.3M

$1,271,665

•

3,153

sq ft

96 Middlesex Ave, Chester, CT 06412

About this home

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.

Single-familyProperty Type

1830Year Built

6.26 acresLot Size

$403Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Susan Malan • William Pitt Sotheby's Int'l

Bought with Matt DeLucia • William Pitt Sotheby's Int'l

Source:Smart MLS #24038493

Redfin Estimate

$1,271,665

$28K since sold in January 2025$170K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 53.5% higher than the average sale price ($828K) of 6 comparable homes.

SOLD NOV 17, 2025
$975,000
A
4 beds2.5 baths3,149 sq ft
7 Old Depot Rd, Chester, CT 06412
SOLD OCT 1, 2026
$825,000
B
4 beds3 baths3,343 sq ft
136 Goose Hill Rd, Chester, CT 06412
SOLD APR 30, 2026
$635,000
C
3 beds3 baths2,752 sq ft
1 Ferry Rd, Chester, CT 06412
SOLD JUL 27, 2026
$515,000
D
3 beds3 baths2,971 sq ft
12 Meadow Ln, Chester, CT 06412
SOLD DEC 12, 2025
$1,275,000
E
3 beds3 baths2,664 sq ft
47 Ferry Rd, Chester, CT 06412
SOLD OCT 9, 2026
$745,000
F
4 beds2.5 baths2,126 sq ft
29 Union St, Deep River, CT 06417

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Earn from this home

Sell

$189,587

Est. take-home

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Rent

$3,416/mo

Redfin rental estimate

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Market trends in 06412, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

100.5%

+0.7% MoM

Median sale price

$500K

$5K MoM

Avg. days on market

44d

13 days MoM

Recently sold homes

0 MoM

New listings for sale

OPEN TODAY, 11AM TO 1PM
$525,000
3 beds2 baths1,822 sq ft
6 Gilbert Hill Rd, Chester, CT 06412
$749,900
4 beds2.5 baths2,662 sq ft
13 High Field Ln, Chester, CT 06412
See all

Provided by Redfin

Sale history for 96 Middlesex Ave

Date

Event

Price

Smart MLS #24038493

Jan 31, 2025

Sold

$1,300,000

$412/sq ft

Jan 23, 2025

Pending

—

Dec 28, 2024

Contingent

—

Dec 11, 2024

Price Changed

$1,375,000

$436/sq ft

Aug 14, 2024

Listed

$1,395,000

$442/sq ft

Smart MLS #170342243

Apr 12, 2022

Sold

$460,000

$146/sq ft

Nov 8, 2020

Contingent

—

Oct 7, 2020

Listed

$498,000

$158/sq ft

This unique property, once a cider mill and orchard, includes a barn style home, circa 1830, on 6 open and landscaped acres. Perfect getaway with multiple outdoor living areas including a wrap around deck with outdoor kitchen, patios, and 2 gazebos. The picturesque acreage boasts flowering shrubs, mature trees and perennial flowers. New England charm and character abound in the interior of the home with 5 bedrooms, 2 fireplaces, a pot-belly stove and milled planking. The great room includes an open kitchen, dining room and large seating area with fireplace, book shelves and vaulted ceiling. A cozy den is complete with another fireplace. The pub/game room, measuring 24 X 22, has soaring ceilings, a built-in bar with sink, and loads of room for entertaining and games. " 5 Car garage too !" This property has already had preliminary work done to subdivide it with 3 additional lots. There is a survey available for the proposed subdivision. The town of Chester has become a well-known destination for an amazing variety of restaurants, one of a kind shops and galleries. Route 9 runs through town and connects to I95 and I84 for an easy commute to New York or Boston.

See LAND LISTING 170345050

Smart MLS #170345040

Dec 29, 2020

Listing Removed

—

Oct 29, 2020

Contingent

—

Oct 7, 2020

Listed

$498,000

$158/sq ft

Smart MLS #170259107

Sep 21, 2020

Listing Removed

—

Dec 21, 2019

Listed

$498,000

$158/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$10,146 (+4.2%)

$80,150 + $261,480

$341,630

2022

$9,737

$80,140 + $249,940

$330,080

2021

$9,737 (+3.1%)

$80,140 + $249,940

$330,080

2020

$9,447 (−0.6%)

$80,140 + $249,940

$330,080

2019

$9,503 (+8.2%)

$80,140 + $249,940

$330,080

2018

$8,785 (+2.8%)

$84,200 + $239,860

$324,060

2017

$8,542 (+3.1%)

$84,200 + $239,860

$324,060

2016

$8,286 (+3.0%)

$84,200 + $239,860

$324,060

2014

$8,043 (−12.4%)

$84,200 + $239,860

$324,060

2011

$9,178

$117,970 + $300,180

$418,150

Tax history for 96 Middlesex Ave

Year

Property tax

Land + Additions

Assessment*

2023

$10,146 (+4.2%)

$80,150 + $261,480

$341,630

2022

$9,737

$80,140 + $249,940

$330,080

2021

$9,737 (+3.1%)

$80,140 + $249,940

$330,080

2020

$9,447 (−0.6%)

$80,140 + $249,940

$330,080

2019

$9,503 (+8.2%)

$80,140 + $249,940

$330,080

2018

$8,785 (+2.8%)

$84,200 + $239,860

$324,060

2017

$8,542 (+3.1%)

$84,200 + $239,860

$324,060

2016

$8,286 (+3.0%)

$84,200 + $239,860

$324,060

2014

$8,043 (−12.4%)

$84,200 + $239,860

$324,060

2011

$9,178

$117,970 + $300,180

$418,150

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

6.26 Acres

Year renovated

1990

Sq. Ft.

3,273

Year built

1830

Style

Single Family Residential

County

Middlesex County

APN

941342

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Under House Garage, Off Street Parking, Driveway
Garages Number: 2

Parking Information
Parking Total Spaces: 6

Interior

Interior Information
Total Rooms: 7
Laundry Room Location: Main floor hall leading to second floor
Laundry Room Info: Main Level
Interior Features: Cable - Pre-wired, Open Floor Plan
In-Law Apartment: No
Appliances
Fireplaces Total: 2
Cooling System: Central Air
Appliances Included: Gas Cooktop, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 3
# of Baths (Half): 1

Bedroom Information
Beds Total: 4

Room Information
Basement Description: Full, Partially Finished, Full With Walk-Out

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Clapboard
Exterior Features: Gazebo, Porch, Wrap Around Deck, Deck, Garden Area, French Doors, Paddock, Patio

Lot Information
Lot Description: Lightly Wooded, Level Lot, Professionally Landscaped, Open Lot

Building Information
Foundation Type: Stone
Construction Description: Frame
Color: White

Property Information
Property Type: Single Family For Sale
Property Info: Horse Property
Living Area SQFT Per Public Record: 3153
Driveway Type: Private, Crushed Stone

Financial

Assessments Information
Assessed Value: $404,460

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: 80 Gallon Tank
Heat Type: Hot Air
Heat Fuel Type: Electric, Propane
Fuel Tank Location: Above Ground
Energy Features: Active Solar

Location

School Information
High School: Valley
Elementary School: Chester

Location Information
State: Connecticut
Nearby Amenities: Basketball Court, Lake, Library, Medical Facilities, Park, Playground/Tot Lot, Public Rec Facilities
Directions: GPS friendly - American flag on pole at the driveway
County: Middlesex

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 3,273
Stories: 1.0
Lot Size: 6.26 acres
Style: Single Family Residential
Year Built: 1830
Year Renovated: 1990
County: Middlesex County
APN: 941342

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 1

Around this home

Schools

K - 12
Preschool & daycare

Chester Elementary School

Public PreK-6 • Assigned • 0.9mi

7/10

John Winthrop Middle School

Public 7-8 • Assigned • 3.0mi

6/10

Valley Regional High School

Public 9-12 • Assigned • 2.5mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 96° expected this year, 16 days in 30 years

6/10 Wind Factor

77% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Chester, CT • 06412

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.5 hours in December, which is comparable to the U.S. average for solar exposure.

9 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.21M – $1.46M

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New listings for sale in 06412

OPEN TODAY, 11AM TO 1PM

$525,000

3 beds2 baths1,822 sq ft

6 Gilbert Hill Rd, Chester, CT 06412

Tranquil cul-de-sac • Updated kitchen • Granite countertops

$749,900

4 beds2.5 baths2,662 sq ft

13 High Field Ln, Chester, CT 06412

Custom colonial • Private acres • Quiet cul-de-sac

Home values near 96 Middlesex Ave

Data from public records.

Address	Redfin Estimate
103 Middlesex Avenue, Chester, CT 2 Beds \| 2 Baths \| 1206 Sq. Ft.	$503,038
114 Middlesex Avenue, Chester, CT 4 Beds \| 2.5 Baths \| 2800 Sq. Ft.	$660,364
105 Middlesex Avenue, Chester, CT 3 Beds \| 2 Baths \| 1344 Sq. Ft.	$476,138
75 Middlesex Avenue, Chester, CT 3 Beds \| 1.5 Baths \| 1632 Sq. Ft.	$519,282
82 Middlesex Avenue, Chester, CT 2 Beds \| 2 Baths \| 1984 Sq. Ft.	$512,596
108 Middlesex Avenue, Chester, CT 4 Beds \| 4.5 Baths \| 4056 Sq. Ft.	$755,201
22 Old Depot Road, Chester, CT 2 Beds \| 1 Baths \| 1640 Sq. Ft.	$420,524

Address	Redfin Estimate
76 Middlesex Avenue, Chester, CT 5 Beds \| 2 Baths \| 2000 Sq. Ft.	$597,523
116 Middlesex Avenue, Chester, CT 3 Beds \| 2 Baths \| 1872 Sq. Ft.	$568,553
79 Middlesex Avenue, Chester, CT 2 Beds \| 1 Baths \| 1470 Sq. Ft.	$467,299
93 Middlesex Avenue, Chester, CT 3 Beds \| 1 Baths \| 1405 Sq. Ft.	$346,549
77 Middlesex Avenue, Chester, CT 3 Beds \| 1 Baths \| 1488 Sq. Ft.	$362,908
28 Old Depot Road, Chester, CT 3 Beds \| 2 Baths \| 1104 Sq. Ft.	$427,958
24 Old Depot Road, Chester, CT 3 Beds \| 2 Baths \| 1344 Sq. Ft.	$439,219

Address	Redfin Estimate
112 Middlesex Avenue, Chester, CT 3 Beds \| 3.5 Baths \| 3168 Sq. Ft.	$823,289
83 Middlesex Avenue, Chester, CT 3 Beds \| 1 Baths \| 1128 Sq. Ft.	$368,197
81 Middlesex Avenue, Chester, CT 2 Beds \| 1 Baths \| 1148 Sq. Ft.	$348,478
115 Middlesex Avenue, Chester, CT 2 Beds \| 1 Baths \| 806 Sq. Ft.	$339,143
101 Middlesex Avenue, Chester, CT 4 Beds \| 2 Baths \| 1459 Sq. Ft.	$485,763
7 Old Depot Road, Chester, CT 4 Beds \| 2.5 Baths \| 3149 Sq. Ft.	$1,118,418
25 Old Depot Road, Chester, CT 2 Beds \| 1.5 Baths \| 1216 Sq. Ft.	$463,229

Property information provided by Smart MLS when last listed in 2024. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06412, CT

Sale history for 96 Middlesex Ave

Tax history for 96 Middlesex Ave

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06412

Home values near 96 Middlesex Ave

More real estate resources