Off market may 2024 for $480K

$506,030

Est. refi paymentEst. refi $2,891/mo

•

1,963

sq ft

16 Middlesex Ave, Chester, CT 06412

About this home

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!

Single-familyProperty Type

1945Year Built

1.06 acresLot Size

$258Est. Price/Sq.Ft.

Listed by Chloe White • KW Legacy Partners

Bought with Lewis Jump III • RE/MAX One

Source:Smart MLS #170609851

Redfin Estimate

$506,030

$26K since sold in May 2024$18K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 2.5% lower than the average sale price ($519K) of 6 comparable homes.

SOLD NOV 9, 2026
$460,000
A
3 beds1.5 baths2,031 sq ft
6 Castle View Dr, Chester, CT 06412
SOLD OCT 2, 2026
$502,500
B
3 beds2 baths2,103 sq ft
11 Castle View Dr, Chester, CT 06412
SOLD NOV 9, 2026
$500,000
C
3 beds2 baths1,774 sq ft
55 Wig Hill Rd, Chester, CT 06412
SOLD OCT 26, 2026
$559,000
D
3 beds2 baths1,740 sq ft
28 Deep Hollow Rd, Chester, CT 06412
SOLD MAR 3, 2026
$495,000
E
3 beds2.5 baths2,018 sq ft
21 River Ln, Deep River, CT 06417
SOLD NOV 6, 2026
$599,000
F
3 beds2 baths1,846 sq ft
32 Sunset Ter, Essex, CT 06426

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Earn from this home

Sell

$108,899

Est. take-home

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Refinance

Est. cash available

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Rent

$2,735/mo

Redfin rental estimate

List your home for rent

Market trends in 06412, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

104.6%

+4.1% MoM

Median sale price

$513K

$13K MoM

Avg. days on market

38d

6 days MoM

Recently sold homes

1 MoM

Provided by Redfin

Sale history for 16 Middlesex Ave

Date

Event

Price

Smart MLS #170609851

May 3, 2024

Sold

$480,000

$245/sq ft

Jan 29, 2024

Pending

—

Dec 18, 2023

Contingent

—

Dec 6, 2023

Price Changed

$499,900

$255/sq ft

Nov 30, 2023

Listed

$515,000

$262/sq ft

Nov 22, 2023

Coming Soon

$515,000

$262/sq ft

Public Records

Aug 9, 2021

Sold

$400,000

$204/sq ft

Smart MLS #170410304

Aug 6, 2021

Listing Removed

—

Aug 6, 2021

Sold

$400,000

$204/sq ft

Jun 23, 2021

Contingent

—

Jun 18, 2021

Listed

$375,000

$191/sq ft

Greetings from 16 Middlesex Avenue in Chester, Connecticut! This cozy home is situated on manicured green, rolling hills accentuated with lovely red maples. If you consider yourself to have a green thumb, this charming property is your new paradise! This 1940’s newly updated 3-bedrrom, 2 full bathroom cape embodies the spirit of Connecticut life. The seasonal views from this Chester home are beautiful from the inside and out! The two-tiered deck features a propane gas grill where you can relax and enjoy the nature around you, including your very own lily pond. Entertaining on this property has an abundance of selections for any occasion. Whether it is a sunny Connecticut afternoon enjoying the outdoors or a chilly evening cozying-up in the partially finished basement. This property is a short walk to the Connecticut River, as well as Chester Village. Move in with ease as the chimney, roof, plumbing, electrical, and furnace have all been updated. This property features custom mosaic window boxes that beautifully enhance the architecture. Other new updates include Andersen Windows throughout with motion sensor light, side entry door/keypad for key-less entry, ADT security system, water filtration system, NEST thermostat, gleaming hardwood floors, crown moulding, and much more! This charmer will not last, schedule your showing today to start cultivating your private oasis! Centrally located between New York City and Boston. Easy access to I-95, Route 80 and Route 9.

SHED IS BEING SOLD "AS IS"...

Smart MLS #M9138961

Jun 24, 2013

Sold

$275,000

$140/sq ft

Feb 21, 2013

Listed

$283,400

$144/sq ft

Public Records

Apr 26, 2010

Sold

$277,500

$141/sq ft

Smart MLS #M9120646

Feb 11, 2010

Listed

$290,000

$148/sq ft

Public Records

Jul 1, 2005

Sold

$300,500

$153/sq ft

Smart MLS #M9083333

Jul 27, 2004

Listed

$318,900

$162/sq ft

Public Records

Dec 10, 1997

Sold

$175,000

$89/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$5,031 (+0.7%)

$57,040 + $112,350

$169,390

2022

$4,997 (+0.9%)

$57,040 + $112,350

$169,390

2021

$4,950 (+3.1%)

$57,040 + $110,760

$167,800

2020

$4,802 (−0.6%)

$57,040 + $110,760

$167,800

2019

$4,831 (+3.3%)

$57,040 + $110,760

$167,800

2018

$4,676 (+2.8%)

$60,210 + $112,290

$172,500

2017

$4,547 (+3.1%)

$60,210 + $112,290

$172,500

2016

$4,411 (+3.0%)

$60,210 + $112,290

$172,500

2014

$4,281 (−15.1%)

$60,210 + $112,290

$172,500

2011

$5,043

$106,670 + $123,100

$229,770

Tax history for 16 Middlesex Ave

Year

Property tax

Land + Additions

Assessment*

2023

$5,031 (+0.7%)

$57,040 + $112,350

$169,390

2022

$4,997 (+0.9%)

$57,040 + $112,350

$169,390

2021

$4,950 (+3.1%)

$57,040 + $110,760

$167,800

2020

$4,802 (−0.6%)

$57,040 + $110,760

$167,800

2019

$4,831 (+3.3%)

$57,040 + $110,760

$167,800

2018

$4,676 (+2.8%)

$60,210 + $112,290

$172,500

2017

$4,547 (+3.1%)

$60,210 + $112,290

$172,500

2016

$4,411 (+3.0%)

$60,210 + $112,290

$172,500

2014

$4,281 (−15.1%)

$60,210 + $112,290

$172,500

2011

$5,043

$106,670 + $123,100

$229,770

*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

1.06 Acres

Year renovated

1994

Sq. Ft.

1,511

Year built

1945

Style

Single Family Residential

County

Middlesex County

APN

941247

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Driveway, Paved

Interior

Interior Information
Total Rooms: 6
Laundry Room Info: Lower Level
Interior Features: Cable - Available, Security System
Security System
Fireplaces Total: 1
Cooling System: Window Unit
Appliances Included: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 2

Bedroom Information
Beds Total: 3

Room Information
Rooms Additional: Laundry Room
Room Count: 10
Basement Description: Full With Walk-Out, Storage
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Aluminum
Exterior Features: Porch

Lot Information
Lot Description: Rolling

Building Information
Foundation Type: Concrete
Construction Description: Frame

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 1511
Driveway Type: Paved

Financial

Assessments Information
Assessed Value: $169,390

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: 50 Gallon Tank
Heat Type: Baseboard
Heat Fuel Type: Oil, Propane
Fuel Tank Location: In Basement

Location

School Information
Middle Jr High School: Winthrop
High School: Valley
Elementary School: Chester

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Lake, Library, Medical Facilities, Park
Directions: W Main St, Right onto Main St, Right onto Middlesex Ave.
County: Middlesex

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 1,511
Stories: 2.0
Lot Size: 1.06 acres
Style: Single Family Residential
Year Built: 1945
Year Renovated: 1994
County: Middlesex County
APN: 941247

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 6

Around this home

Schools

K - 12
Preschool & daycare

Chester Elementary School

Public PreK-6 • Assigned • 1.0mi

7/10

John Winthrop Middle School

Public 7-8 • Assigned • 2.5mi

6/10

Valley Regional High School

Public 9-12 • Assigned • 1.9mi

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 93° 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)

34°

21°

36°

22°

51°

33°

60°

42°

68°

51°

80°

60°

83°

66°

80°

59°

76°

57°

64°

47°

54°

38°

39°

25°

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

$481,000 – $582,000

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Nearby similar homes

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Home values near 16 Middlesex Ave

Data from public records.

Address	Redfin Estimate
17 Middlesex Ave, Chester, CT 2 Beds \| 1 Baths \| 2317 Sq. Ft.	$562,081
30 Middlesex Ave, Chester, CT 2 Beds \| 1.5 Baths \| 1362 Sq. Ft.	$389,910
35 Middlesex Ave, Chester, CT 3 Beds \| 2 Baths \| 1425 Sq. Ft.	$491,787
27 Middlesex Ave, Chester, CT 4 Beds \| 2.5 Baths \| 2416 Sq. Ft.	$583,788
19 Middlesex Ave, Chester, CT 3 Beds \| 2 Baths \| 1968 Sq. Ft.	$456,720
7 Main St, Deep River, CT 2 Beds \| 2 Baths \| 1112 Sq. Ft.	—
41 Winter Ave, Deep River, CT 2 Beds \| 1.5 Baths \| 1206 Sq. Ft.	$453,473

Address	Redfin Estimate
24 Middlesex Ave, Chester, CT 4 Beds \| 1 Baths \| 1338 Sq. Ft.	$434,769
25 Middlesex Ave, Chester, CT 3 Beds \| 2.5 Baths \| 1666 Sq. Ft.	$386,402
18 Middlesex Ave, Chester, CT 5 Beds \| 2.5 Baths \| 2088 Sq. Ft.	$554,848
15 Middlesex Ave, Chester, CT 2 Beds \| 2 Baths \| 1770 Sq. Ft.	$445,928
1 Gilbert Hill Rd, Chester, CT 1 Beds \| 1 Baths \| 1112 Sq. Ft.	$470,454
1 Main St, Deep River, CT 3 Beds \| 2 Baths \| 1306 Sq. Ft.	$406,569
45 Winter Ave, Deep River, CT 3 Beds \| 2 Baths \| 996 Sq. Ft.	$439,430

Address	Redfin Estimate
20 Middlesex Ave, Chester, CT 3 Beds \| 2.5 Baths \| 1914 Sq. Ft.	$536,789
28 Middlesex Ave, Chester, CT 3 Beds \| 2.5 Baths \| 1582 Sq. Ft.	$461,350
9 Middlesex Ave, Chester, CT 3 Beds \| 1.5 Baths \| 1391 Sq. Ft.	$452,555
29 Middlesex Ave, Chester, CT 3 Beds \| 2 Baths \| 1416 Sq. Ft.	$417,941
51 Winter Ave, Deep River, CT 2 Beds \| 1 Baths \| 1116 Sq. Ft.	$414,303
50 Winter Ave, Deep River, CT 2 Beds \| 1 Baths \| 687 Sq. Ft.	$341,768

Property information provided by Smart MLS when last listed in 2023. 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 16 Middlesex Ave

Tax history for 16 Middlesex Ave

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

Home values near 16 Middlesex Ave

More real estate resources