For sale

$2,200,000

Est. $14,258/mo —

•

5,234

sq ft

88 Main St, Ivoryton, CT 06442

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.

See attachments for an extensive list of house history and improvements. Field Card states 4 bedrooms, but this home operates with 5 bedrooms.

Single-familyProperty Type

1849Year Built

1.86 acresLot Size

$420Price/Sq.Ft.

2 garage spacesParking

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

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

Source:Smart MLS #24200306

Payment calculator

$14,258 per month

Principal and interest$12,156

Property taxes

$1,259

HOA dues

Home insurance

$843

Utilities

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Affordability tools

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Open houses

No upcoming open houses.

Nearby open houses (10)

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21-1 Haywagon Dr, Old Lyme, CT 06371
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4 beds3.5 baths2,165 sq ft
57 Walnut St, Ivoryton, CT 06442
OPEN SUN, 9:30AM TO 11:30AM
$469,000
3 beds1.5 baths1,748 sq ft
270 Scotland Rd, Madison, CT 06443
OPEN SUN, 12PM TO 2PM
$619,900
4 beds2.5 baths3,524 sq ft
252 N Bride Brook Rd, East Lyme, CT 06333
OPEN SUN, 12PM TO 3PM
$928,000
3 beds3.5 baths2,950 sq ft
60 Bushy Hill Rd, Ivoryton, CT 06442
OPEN SUN, 1PM TO 3PM
$500,000
3 beds2.5 baths1,440 sq ft
173 Chestnut Hill Rd, Killingworth, CT 06419
OPEN SUN, 1PM TO 3PM
$475,000
3 beds2.5 baths3,032 sq ft
33 N High St, Clinton, CT 06413
OPEN SUN, 1PM TO 3PM
$619,900
3 beds2 baths2,480 sq ft
433 Route 148, Killingworth, CT 06419
OPEN SUN, 1:30PM TO 3PM
$599,900
4 beds1.5 baths1,884 sq ft
14 Bower Rd, Madison, CT 06443

Around this home

Schools

K - 12
Preschool & daycare

Essex Elementary School

Public PreK-6 • Assigned • 1.0mi

7/10

John Winthrop Middle School

Public 7-8 • Assigned • 1.5mi

4/10

Valley Regional High School

Public 9-12 • Assigned • 1.7mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

88 Main St · $2,200,000

Strong offer

$2.21M and above

75% chance or better to win

Why $2.21M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 43 days.

SALE-TO-LIST

Most homes are selling 3% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Automatic garage door opener
Cable available
Programmable thermostat
Thermostat-controlled home automation

Bedrooms
5 bedrooms

Bathrooms
5 full baths
1 half bath

Kitchen
Gas cooktop
Oven/Range
Microwave
Sub-Zero refrigerator
Dishwasher
Wine chiller

Laundry & utility
Washer and dryer included
Laundry room on the 2nd floor

Heating & cooling
Steam heat (oil-fired)
Central air conditioning
40-gallon hot water tank

Sale and tax history for 88 Main St

Sale History
Tax History

Date

Event

Price

Smart MLS #24200306

Aug 20, 2026

Listed

$2,200,000

$420/sq ft

Smart MLS #24162042

Jul 20, 2026

Listing Removed

—

Jun 8, 2026

Price Changed

$2,600,000

$497/sq ft

Apr 9, 2026

Listed

$2,800,000

$535/sq ft

Smart MLS #170208110

Feb 16, 2021

Sold

$730,000

$139/sq ft

Sep 21, 2020

Contingent

—

May 21, 2020

Relisted

—

Nov 7, 2019

Listing Removed

—

Jul 10, 2019

Listed

$795,000

$152/sq ft

This magnificent estate is one of the most admired homes in Essex. Enter from the elegant Porte Cochere into a “glass” porch. The ballroom-like living room is full of light and features a large box-bay-window seat, fireplace, bookcases, and gleaming floor. The handsome gourmet kitchen-family room boasts a large black cherry island, granite counters, subzero, Wolf stove top, 2 drawer dishwasher, double ovens, and fireplace. Two pair of sliders open from the family onto the spacious Pau Lope wood deck. The unusual formal dining-room space has two additional fireplaces close-by. The den/office has a full bath and is adjacent to a utility room affording the flexibility of first floor living. The back door enters into a light filled sitting room with a tile floor. The sumptuous master bedroom with a gorgeous maple floor opens to the large master bath with thermostat-masseur tub and 7 head shower. Three additional bedrooms and three full baths, a porch/sunroom with builtins, and an entry to the attic stairs completes the second floor. The 1.86 acre property is graced by large shade trees, flowering trees, rhododendrons and evergreens. A short walk from the deck brings you to the 20x40 in-ground pool with a bluestone patio. The charming village offers a Post Office, 3 restaurants, a library, the famous Ivoryton Playhouse, and close-by proximity to the Connecticut River, Marinas, yacht clubs, and so much more.

Year

Property tax

Land + Additions

Assessment*

2023

$12,063 (−0.5%)

$57,100 + $476,900

$534,000

2022

$12,125 (+4.7%)

$57,100 + $478,200

$535,300

2021

$11,581 (+2.8%)

$57,100 + $459,200

$516,300

2020

$11,261 (+0.7%)

$57,100 + $459,200

$516,300

2019

$11,178 (−7.3%)

$57,100 + $459,200

$516,300

2018

$12,059 (−0.5%)

$60,000 + $491,900

$551,900

2017

$12,120 (+1.8%)

$60,000 + $491,900

$551,900

2016

$11,910 (+2.4%)

$60,000 + $491,900

$551,900

2015

$11,634 (+0.4%)

$60,000 + $491,900

$551,900

2014

$11,584 (+2.0%)

$60,000 + $491,900

$551,900

2011

$11,360

$66,700 + $531,500

$598,200

Public record

Beds

Baths

5.5

Stories

Lot width

—

Lot depth

—

Lot size

1.86 Acres

Year renovated

—

Finished Sq. Ft.

5,234

Unfinished Sq. Ft.

—

Total Sq. Ft.

5,234

Year built

1849

Style

Single Family Residential

County

Middlesex County

APN

985792

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 24, 2026.

Historical weather

Ivoryton, CT • 06442

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

94/ 100

Exceptional sunlight

Sunscore

This home ranks in the top 25% for direct sun exposure in Ivoryton. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.3 hrs

6.3 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 88 Main St

$2,110,178

$90K under list price of $2.20M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $715K to $3.8M.

SOLD AUG 29, 2026
$925,000 Last sold price
6 beds4.5 baths2,772 sq ft
7 Orchard Heights Rd, Essex, CT 06426
$86/sq ft
153 years newer
SOLD AUG 7, 2026
$1,400,000 Last sold price
3 beds3.5 baths2,467 sq ft
45 Falls River Dr, Ivoryton, CT 06442
$147/sq ft
smaller lot
132 years newer
SOLD AUG 31, 2026
$715,000 Last sold price
3 beds2.5 baths1,979 sq ft
199 Westbrook Rd, Essex, CT 06426
$59/sq ft
smaller lot
136 years newer
SOLD SEP 11, 2026
$3,795,000 Last sold price
3 beds3.5 baths4,383 sq ft
7 Hanna Ln, Essex, CT 06426
$446/sq ft
smaller lot
106 years newer
SOLD AUG 21, 2026
$775,000 Last sold price
3 beds3 baths2,887 sq ft
9 Brooks Ln, Ivoryton, CT 06442
$152/sq ft
smaller lot
140 years newer
SOLD JUN 25, 2026
$847,000 Last sold price
3 beds3.5 baths3,476 sq ft
74 Bushy Hill Rd, Ivoryton, CT 06442
$176/sq ft
larger lot
112 years newer

Rental earnings

Est. $4,181 per month, based on comparable rentals

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(203) 896-7209

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New listings for sale in 06442

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Details provided by Smart MLS and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Lifestyle

Offer insights

Property details

Sale and tax history for 88 Main St

Public record

Historical weather

Sun exposure

Redfin Estimate for 88 Main St

Nearby similar homes

New listings for sale in 06442

More real estate resources