Sold on jun 2026

$618,000

•

1,128

sq ft

81 Main St, Chester, CT 06412

Track this home’s value and nearby sales activity

About this home

Discover the perfect blend of mid-century character and modern efficiency in the heart of Chester Village. This impeccably maintained home offers a vibrant "walk-to-everything" lifestyle, just steps from award-winning dining, boutiques, and the theater. Officially a 2-bedroom home per town records, the layout offers incredible flexibility. The main level features a stunning den currently utilized as a primary suite. This light-filled space features a private, fully renovated ensuite full bath and a handsome armoire for storage, offering a sophisticated retreat for those seeking first-floor living. Note: This serves as the primary bath for the main level, enhancing the "suite" feel of the space. Upstairs, you will find two additional well-appointed rooms and a second fully renovated full bath, providing ample space for guests or a home office. The home's infrastructure has been flawlessly upgraded, featuring a new 50-year roof, on-demand propane heat/hot water, and an electric heat pump for heating and cooling (A/C on the first floor). The updated eat-in kitchen is a chef's delight, while the professional landscaping and beautiful stone patio create a private oasis for outdoor entertaining. Rarely does a home combine such high-end mechanical peace of mind with the undeniable charm of a downtown location. Turn-key and ready for its next chapter-experience the best of Chester right outside your front door.

Single-familyProperty Type

1950Year Built

6,534 sq ftLot Size

$548Price/Sq.Ft.

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

Contact: Agent Attribution Contact: (203) 215-8676 | Office Attribution Contact: (203) 245-6700

Bought with Tina Rupp • William Pitt Sotheby's Int'l

Source:Smart MLS #24172804

Redfin Estimate

$548,916

$69K since sold in June 2026$5,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 14.5% higher than the average sale price ($479K) of 6 comparable homes.

SOLD OCT 19, 2026
$429,900
A
2 beds1 bath1,114 sq ft
58 Union St, Deep River, CT 06417
SOLD AUG 25, 2026
$452,000
B
3 beds1.5 baths1,198 sq ft
1 Kirtland Ave, Chester, CT 06412
SOLD JUN 29, 2026
$430,000
C
2 beds1 bath1,200 sq ft
12 Jones Ln, Deep River, CT 06417
SOLD JUN 12, 2026
$470,000
D
3 beds1.5 baths1,092 sq ft
19 Castle View Dr, Chester, CT 06412
SOLD JUL 24, 2026
$345,000
E
2 beds1 bath912 sq ft
8 Prospect Hl, Deep River, CT 06417
SOLD SEP 25, 2026
$750,000
F
2 beds2 baths1,654 sq ft
40 Sunset Ter, Essex, CT 06426

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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

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

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Rental estimate

Est. $2,419 per month, based on comparable rentals

Sale and tax history for 81 Main St

Sale History
Tax History

Date

Event

Price

Smart MLS #24172804

Jun 11, 2026

Sold

$618,000

$548/sq ft

May 16, 2026

Pending

—

May 11, 2026

Listed

$550,000

$488/sq ft

May 8, 2026

Coming Soon

$550,000

$488/sq ft

Smart MLS #G647421

Jul 18, 2013

Sold

$260,000

$230/sq ft

Apr 9, 2013

Listed

$275,000

$244/sq ft

Public Records

Apr 2, 2002

Sold

$155,000

$137/sq ft

Smart MLS #M9062507

Feb 22, 2001

Listed

$175,000

$155/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$4,450 (+0.7%)

$86,190 + $63,650

$149,840

2022

$4,420

$86,190 + $63,650

$149,840

2021

$4,420 (+3.1%)

$86,190 + $63,650

$149,840

2020

$4,288 (−0.6%)

$86,190 + $63,650

$149,840

2019

$4,314 (−1.2%)

$86,190 + $63,650

$149,840

2018

$4,365 (+2.9%)

$90,720 + $70,300

$161,020

2017

$4,244 (+3.1%)

$90,720 + $70,300

$161,020

2016

$4,117 (+3.0%)

$90,720 + $70,300

$161,020

2014

$3,997 (−2.1%)

$90,720 + $70,300

$161,020

2011

$4,082

$115,380 + $70,590

$185,970

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

6,534 Sq. Ft.

Year renovated

1995

Sq. Ft.

1,128

Year built

1950

Style

Single Family Residential

County

Middlesex County

APN

940179

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Interior

Interior Information
Total Rooms: 5
Laundry Room Location: Off the kitchen and down a few stairs.
Laundry Room Info: Main Level
Interior Features: Open Floor Plan
Cooling System: Heat Pump, Window Unit
Appliances Included: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 2

Bedroom Information
Beds Total: 2

Room Information
Basement Description: Crawl Space
Has Attic
Attic Description: Storage Space, Access Via Hatch

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Wood
Exterior Features: Gutters, Garden Area, Patio

Lot Information
Lot Description: Treed, Level Lot, Professionally Landscaped

Land Information
Encumbrances Restrictions: Easements, Right of Way

Building Information
Foundation Type: Block
Construction Description: Frame
Color: Sage

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 1128

Financial

Assessments Information
Assessed Value: $203,210

Utilities

Utility Information
Water Source: Public Water Connected
Sewer Usage Fee Annual: $750
Sewage System: Public Sewer Connected
Hot Water Description: Domestic, Tankless Hotwater
Heat Type: Heat Pump, Radiator
Heat Fuel Type: Electric, Propane
Fuel Tank Location: Above Ground
Energy Features: Storm Doors, Thermopane Windows

Location

School Information
High School: Per Board of Ed
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Directions: GPS friendly.
County: Middlesex

Public facts

Beds: 2
Baths: 2.0
Sq. Ft.: 1,128
Stories: 1.0
Lot Size: 6,534 square feet
Style: Single Family Residential
Year Built: 1950
Year Renovated: 1995
County: Middlesex County
APN: 940179

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 4

Around this home

Schools

Chester Elementary School

Public PreK-6 • Assigned • 0.5mi

7/10

John Winthrop Middle School

Public 7-8 • Assigned • 2.6mi

6/10

Valley Regional High School

Public 9-12 • Assigned • 2.2mi

7/10

Provided by GreatSchools

Climate risks

4/10 Flood Factor

Estimated 18-28% chance 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

82/ 100

Very good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.7 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$522,000 – $632,000

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Nearby similar homes

$2,995,000

4 beds5 baths4,926 sq ft

288 Middlesex Ave, Chester, CT 06412

Deep water access • Manicured grounds • Broad terrace

$2,400,000

3 beds4 baths4,711 sq ft

150-1 Mitchell Hill Rd, Lyme, CT 79532

22.92 acres • Gourmet kitchen • Glass solarium

$575,000

5 beds2 baths2,090 sq ft

100 N Tower Hill Rd, Killingworth, CT 06419

New windows • New boiler • New septic system

3D WALKTHROUGH

$835,000

3 beds3 baths2,606 sq ft

170 Bushy Hill Rd, Deep River, CT 06417

Four-season sunroom • Private tiered deck • Spa bath

3D WALKTHROUGH

$1,900,000

4 beds3.5 baths3,957 sq ft

47 E Kings Hwy, Chester, CT 06412

3.2 acre lot • 4 garage spots • Built 1798

$3,850,000

5 beds6 baths7,155 sq ft

484 Joshuatown Rd, Lyme, CT 06371

Dock access • Ipe decks • Bluestone patios

Home values near 81 Main St

Data from public records.

Address	Redfin Estimate
112 Main Street #B, Chester, CT 3 Beds \| 2 Baths \| 2093 Sq. Ft.	$487,550
52 Main Street, Chester, CT 2 Beds \| 2 Baths \| 918 Sq. Ft.	$445,957
105 Main Street, Chester, CT 3 Beds \| 2.5 Baths \| 2353 Sq. Ft.	$590,694
108 Main Street, Chester, CT 3 Beds \| 1 Baths \| 1708 Sq. Ft.	$407,743
59 Main Street, Chester, CT - Beds \| - Baths \| - Sq. Ft.	$302,432
112 Main Street, Chester, CT - Beds \| - Baths \| - Sq. Ft.	$308,714
12 Maple Street, Chester, CT - Beds \| - Baths \| - Sq. Ft.	$677,444

Address	Redfin Estimate
109 Main Street, Chester, CT 3 Beds \| 2.5 Baths \| 1532 Sq. Ft.	$719,449
112 Main Street #C, Chester, CT 3 Beds \| 2 Baths \| 1278 Sq. Ft.	$383,699
44 Main Street, Chester, CT 3 Beds \| 1 Baths \| 1100 Sq. Ft.	$394,716
101 Main Street, Chester, CT 4 Beds \| 3 Baths \| 2876 Sq. Ft.	$721,582
97 Main Street, Chester, CT - Beds \| - Baths \| - Sq. Ft.	$388,500
25 E Liberty Street, Chester, CT 3 Beds \| 2 Baths \| 2196 Sq. Ft.	$587,822
11 Maple Street #A, Chester, CT 1 Beds \| 1 Baths \| 827 Sq. Ft.	$195,434

Address	Redfin Estimate
73 Main Street, Chester, CT 2 Beds \| 2 Baths \| 1823 Sq. Ft.	$551,016
83 Main Street, Chester, CT 4 Beds \| 3 Baths \| 2363 Sq. Ft.	$780,498
112 Main Street #A, Chester, CT 2 Beds \| 2 Baths \| 1021 Sq. Ft.	$371,430
45 Main Street, Chester, CT 5 Beds \| 4 Baths \| 3531 Sq. Ft.	$870,366
61 Main Street, Chester, CT - Beds \| - Baths \| - Sq. Ft.	$399,309
25 Maple Street, Chester, CT - Beds \| - Baths \| - Sq. Ft.	—
11 Maple Street #B, Chester, CT 1 Beds \| 1 Baths \| 828 Sq. Ft.	$195,449

Property information provided by Smart MLS when last listed in 2026. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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81 Main St, Chester, CT 06412

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About this home

Redfin Estimate

Market trends in 06412, CT

Homeowner tools

Sale and tax history for 81 Main St

Public record

Property details

Interior

Exterior

Financial

Utilities

Location

Public facts

Other

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

Home values near 81 Main St

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