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88 Main StreetEssex, CT 06442

Single Family · 5 Beds · 5 Full Baths · 1 Half Bath · 5,234 Sq. ft. | 1.86 Acres
$2,600,000 Active

88 Main Street Overview

Time on Site:
84 days

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. And the 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.

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88 Main Street Facts & Features

  • Type Single Family
  • Sq. ft. 5,234
  • Price/Sq.ft. $497
  • Lot 1.86 Acres

Details

General

Association/HOA

  • Association: No

School Information

  • Elementary School: Essex
  • Middle Or Junior School: Winthrop
  • High School: Valley
  • Intermediate School: Per Board of Ed

Listing Information

  • Bank Owned Property: No
  • Potential Short Sale: No

Building Information

  • Year Built: 1849

Location/Region

  • County Or Parish: Middlesex
  • Neighborhood: Ivoryton

Building Exterior/Construction

  • New Construction Type: No/Resale

Tax Information

  • Tax Annual Amount: $14,375.00
  • Tax Year: July 2025-June 2026

General Information

  • Exclusions: Chandelier in Parlor Sitting Room
  • Flood Zone: No
  • Parcel Number: 985792
  • Property Type: Single Family For Sale
  • Zoning: VR

Interior

Parking Information

  • Garage Spaces: 2

Beds/Baths

  • Bathrooms Full: 5
  • Bathrooms Half: 1
  • Bathrooms Total: 6
  • Bedrooms Total: 5

Building Interior

  • Attic Description: Unfinished, Storage Space, Floored, Walk-up
  • Attic: Yes
  • Energy Features: Programmable Thermostat
  • Fuel Tank Location: Above Ground
  • Heat Fuel Type: Oil
  • Home Automation: Thermostat(s)
  • Hot Water Description: Oil, 40 Gallon Tank
  • Laundry Room Location: 2nd floor
  • Rooms Additional: Foyer, Laundry Room, Sitting Room

General Information

  • Appliances: Gas Cooktop, Oven/Range, Microwave, Subzero, Dishwasher, Washer, Dryer, Wine Chiller
  • Basement: Full, Unfinished
  • Cooling: Central Air
  • Fireplaces Total: 3
  • Foundation Details: Stone
  • Heating: Heat Pump, Hot Air, Radiator, Zoned
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Living Area: 5234

Exterior

Building Information

  • Driveway Type: Private, Paved

Parking Information

  • Parking Features: Detached Garage, Driveway
  • Parking Total: 8

Lot Information

  • Lot Features: Fence - Full, Level Lot, Professionally Landscaped
  • Lot Size Acres: 1.86
  • Lot Size Source: Public Records
  • Water Source: Public Water Connected

Waterfront/View

  • Waterfront Features: Not Applicable
  • Waterfront: No

Building Exterior/Construction

  • Architectural Style: Colonial
  • Color: White
  • Construction Materials: Clapboard
  • Roof: Asphalt Shingle

General Information

  • Exterior Features: Porch-Enclosed, Porch, Gutters, Garden Area, Patio
  • Pool Features: Gunite, Heated, Salt Water, In Ground Pool
  • Pool Private: Yes
  • Sewer: Septic

Room Information

Room: Bedroom

  • Level: Main
  • Length: 16.9
  • Width: 9.7
  • Description: Remodeled,Bedroom Suite,Full Bath,Hardwood Floor

Room: Eat-In Kitchen

  • Level: Main
  • Length: 14.1
  • Width: 16.3
  • Description: Remodeled,Breakfast Bar,Quartz Counters,Eating Space,Island,Hardwood Floor

Room: Family Room

  • Level: Main
  • Length: 25
  • Width: 17.4
  • Description: Remodeled,Fireplace,Sliders,Hardwood Floor

Room: Living Room

  • Level: Main
  • Length: 33.4
  • Width: 25.9
  • Description: Remodeled,Book Shelves,Built-Ins,Combination Liv/Din Rm,Fireplace,Hardwood Floor

Room: Office

  • Level: Main
  • Length: 11.7
  • Width: 11.2
  • Description: Remodeled,Hardwood Floor

Room: Other

  • Level: Main
  • Length: 14.1
  • Width: 24.6
  • Description: Remodeled,Fireplace,Half Bath,Hardwood Floor

Room: Sun Room

  • Level: Main
  • Length: 17.4
  • Width: 12.3
  • Description: Remodeled,Tile Floor

Room: Sun Room

  • Level: Main
  • Length: 12.9
  • Width: 13.5
  • Description: Remodeled,Tile Floor

Room: Bedroom

  • Level: Upper
  • Length: 22.8
  • Width: 14.1
  • Description: Remodeled,Bedroom Suite,Full Bath,Hardwood Floor

Room: Bedroom

  • Level: Upper
  • Length: 15.6
  • Width: 14.7
  • Description: Remodeled,Bedroom Suite,Full Bath,Hardwood Floor

Room: Bedroom

  • Level: Upper
  • Length: 18.9
  • Width: 10.1
  • Description: Remodeled,Hardwood Floor

Room: Office

  • Level: Upper
  • Length: 13.5
  • Width: 12.9
  • Description: Remodeled,Book Shelves,Built-Ins,Hardwood Floor

Room: Primary BR Suite

  • Level: Upper
  • Length: 12.11
  • Width: 17.4
  • Description: Remodeled,Bedroom Suite,Dressing Room,Full Bath,Walk-In Closet,Hardwood Floor

88 Main Street Monthly Cost

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

88 Main Street Market Data

Based on the last 30 days in this zip code

$779,907
Average List Price
$372
Average Price per Square Foot
4
Properties Sold
53
Average Days on Market
14
Properties for Sale
Calculations provided by Reliance Network

88 Main Street History

Date Event Value Agent
6/8/2026Source: Smart MLS Price Reduction
$2,600,000 -7.1%
4/8/2026Source: Smart MLS Status Change
Active
4/6/2026Source: Smart MLS Added to Database
April 06, 2026
6/20/2022Source: Smart MLS Added to Database
September 13, 2021
Listing provided courtesy of William Pitt Sotheby's Int'l- MLS# 24162042MLS ProviderContact Information: (203) 500-4000