88 Main Street
Essex, Connecticut 06426
- Beds
- 5
- Baths
- 5 | 1
- SqFt
- 5,234
- Acres
- 1.86
- Year Built
- 1849
- Neighborhood
- Ivoryton
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
23
14 under contract
Median List Price
$999,000
23 active listings
Median Closed Price
$735,000
75 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per 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
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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.