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88 Main Street

Essex, Connecticut 06426

ACTIVE - NEW$2,200,000
Beds
5
Baths
5 | 1
SqFt
5,234
Acres
1.86
Year Built
1849
Matt Caiola

Matt Caiola

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About This Home

Two hours from New York City. Two hours from Boston. A world away from both. Privacy is the ultimate luxury. This masterfully re-imagined 5,234 sq. ft. compound located in historic Ivoryton, a village within the town of Essex, sits behind newly established hedges on nearly two flat, manicured acres - completely turn-key, completely private. The grounds are designed for outdoor living. A 20 X 40 gunite pool flows into a hydrangea-framed landscape. Three bluestone patios for entertaining, dining, and quiet retreat. A newly built two-car garage, wired with new electrical and EV charger-ready. Inside, the transformation is total. A chef's kitchen built around a custom black cherry island with Sub-Zero refrigerator, new double wall oven, and cooktop. A butler's pantry adds a second refrigerator and dedicated wine fridge. Four bedrooms with private en suite bathrooms, including a reimagined primary suite with spa-level finishes. Two home offices. An inviting Family Room. A spectacular Living Room. And a Sunroom - a fully restored 1920s porch with original terra cotta floors and sweeping estate views. Every room is professionally curated with bespoke wallcoverings and custom light fixtures. Steps from the Ivoryton Playhouse, The Copper Beech, and Prive Swiss. Minutes to Connecticut River marinas. Long Island Sound 15 minutes beyond. A truly unique property located in what Yankee Magazine ranks as the #1 small town in New England.

Key Facts

City/Town
Essex
Neighborhood
Ivoryton
Property / Style
Single Family · Colonial
Year Built
1849
Days on Market
0 days
Beds
5
Baths
5 full · 1 half
Living Area
5,234 sq ft
Lot Size
1.86 acres
Garage / Parking
2 garage · 8 total
Property Taxes
$15,106 / Annually

Market Snapshot

The Essex Market

Single Family · trailing 12 months

Median Days on Market

57

23 active listings

Median $ / Sq Ft

$436

23 active listings

Sale-to-List Ratio

100.0%

75 sales

How this home compares

List Price

$2.20M

vs $999,000 median

2.2× the median

Price / Sq Ft

$420

vs $436 median

In line with median

Days on Market

0 days

vs 57 days median

57 days fresher than median

Based on 23 active and 75 closed sales (trailing 12 mo) of single family in Essex. Source: SmartMLS · As of August 20, 2026.

Location

88 Main Street, Essex, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$13,314

per month

  • Principal & Interest$11,322
  • Property Taxes$1,259
  • Insurance$733
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Essex
Neighborhood
Ivoryton
County
Middlesex

Residence

Property Type
Single Family
Style
Colonial
Year Built
1849
New Construction
No/Resale
Living Area
5,234 sq ft

Schools

Elementary
Essex
Middle
Per Board of Ed
High
Valley

Interior

Heating
Steam
Heat Fuel
Oil
Cooling
Central Air
Laundry Location
2nd floor
Appliances
Gas CooktopOven/RangeMicrowaveSubzeroDishwasherWasherDryerWine Chiller
Basement
FullUnfinished
Interior Features
Auto Garage Door OpenerCable - Available
Additional Rooms
FoyerLaundry RoomSitting Room

Exterior & Lot

Lot Size
1.86 acres
Zoning
VR
Garage / Parking
2 garage spaces8 total parking spacesDetached GarageDrivewayPrivatePaved
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Flood Zone
No
Pool
GuniteHeatedSalt WaterIn Ground Pool
Construction
Clapboard
Color
White
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
Porch-EnclosedPorchGuttersGarden AreaPatio
Lot Description
Fence - FullLevel LotProfessionally Landscaped

Listing & Financials

Property Taxes
$15,106 / Annually
Days on Market
0
MLS #
24200306
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Kirsten Adams

(203) 500-4000

William Pitt Sotheby's Int'l

(203) 245-6700

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/20/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 8/20/2026 at 3:25 PM UTC.