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$2,600,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 1 Partial Bath
  • 5,234 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 88 Main St

General

  • Price: $2,600,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24162042
  • Updated: 6/9/2026
  • Added to Site: 94 day(s) ago

Interior

  • Number of Rooms: 10
  • Rooms/Areas: Foyer, Laundry Room, Sitting Room
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Gas Cooktop, Oven/Range, Microwave, Subzero, Dishwasher, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 5
  • Primary Suite: Remodeled, Bedroom Suite, Dressing Room, Full Bath, Wa, 12.11 x 17.4, Upper
  • Bedroom 1: Bedroom - Remodeled, Bedroom Suite, Full Bath, Hardwood Floor, 16.9 x 9.7, Main
  • Bedroom 2: Bedroom - Remodeled, Bedroom Suite, Full Bath, Hardwood Floor, 15.6 x 14.7, Upper
  • Bedroom 3: Bedroom - Remodeled, Hardwood Floor, 18.9 x 10.1, Upper
  • Bedroom 4: Bedroom - Remodeled, Bedroom Suite, Full Bath, Hardwood Floor, 22.8 x 14.1, Upper

Other Rooms

  • Living Room: Living Room - Remodeled, Book Shelves, Built-Ins, Combination Liv/Din Rm, Fireplace, Hardwood Floor, 33.4 x 25.9, Main
  • Family Room: Family Room - Remodeled, Fireplace, Sliders, Hardwood Floor, 25 x 17.4, Main
  • Eat In Kitchen: Eat-In Kitchen - Remodeled, Breakfast Bar, Quartz Counters, Eating Space, Islan, 14.1 x 16.3, Main
  • Office: Office - Remodeled, Hardwood Floor, 11.7 x 11.2, Main
  • Other Room 1: Other - Remodeled, Fireplace, Half Bath, Hardwood Floor, 14.1 x 24.6, Main

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, Salt Water, In Ground Pool

Exterior

  • Exterior Features: Porch-Enclosed, Porch, Gutters, Garden Area, Patio
  • Color: White

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 8
  • Parking: Detached Garage, Driveway

Location

  • County: Middlesex
  • Neighborhood: Ivoryton
  • Driving Directions: #88 Main is located in the heart of Ivoryton, next to the Town Post Office.

School Information

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

Community

  • Community Name: Ivoryton

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Heat Pump, Hot Air, Radiator, Zoned, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, 40 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Unfinished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 5,234
  • Above Ground: 5,234 Sq. Ft.
  • Year Built: 1849

Lot Features

  • Lot Size (Acres): 1.86
  • Driveway/Sidewalk: Private, Paved
  • Zoning: VR
  • Lot Description: Fence - Full, Level Lot, Professionally Landscaped

Green Features

  • Energy Features: Programmable Thermostat

Financial Considerations

  • Assessment Amount: $771,600
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Chandelier in Parlor Sitting Room
  • Property ID: 985792

Listed by William Pitt Sotheby's Int'l, Kirsten Adams

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Listing agent

— 88 Main St —

  • Kirsten Adams

    William Pitt Sotheby's Int'l

Agent Contact: (203) 500-4000 Office Contact: (203) 245-6700

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 88 Main St

School Districts:Essex School District, Regional High School District 04
NameGradesDistance
Essex Elementary School
108 Main St., Essex, CT 06409
PK-61.1 mi
John Winthrop Middle School
1 Winthrop Road, Deep River, CT 06417
7-81.5 mi
Valley Regional High School
256 Kelsey Hill Road, Deep River, CT 06417
9-121.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 88 Main St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/08/2026
Price Reduced
$2,600,000
-7.14%
MLS
4/09/2026
Listed
$2,800,000
283.56%
MLS
2/03/2021
Sold
$730,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 88 Main St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,375
3%
$771,600
—
2023
$13,927
15%
$771,600
44%
2023
$12,063
-1%
$534,000
—
2022
$12,125
5%
$535,300
4%
2021
$11,581
3%
$516,300
—
2020
$11,261
1%
$516,300
—
2019
$11,178
-7%
$516,300
-6%
2018
$12,059
-1%
$551,900
—
2017
$12,120
2%
$551,900
—
2016
$11,910
2%
$551,900
—
2015
$11,634
—
$551,900
—
2014
$11,584
2%
$551,900
-8%
2011
$11,360
—
$598,200
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by William Pitt Sotheby's Int'l, Kirsten Adams

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88 Main Street, Essex, CT 06442 (MLS# 24162042) is a Single Family property with 5 bedrooms, 5 full bathrooms and 1 partial bathroom. 88 Main Street is currently listed for $2,600,000 and was received on April 06, 2026. Want to learn more about 88 Main Street? Do you have questions about finding other Single Family real estate for sale in Essex? You can browse all Essex real estate or contact a Coldwell Banker agent to request more information.

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