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342 Midlock Road

Fairfield, Connecticut 06824

PENDING$2,799,999
Beds
5
Baths
6 | 1
SqFt
7,269
Acres
2.03
Year Built
1998
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

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Pool3-Car Garage5 Fireplaces

About This Home

Welcome to an unrivaled sanctuary of sophistication at 342 Midlock Road, gracefully situated in the prestigious enclave of Greenfield Hill. This stately residence, perched on a coveted cul-de-sac off Burr Street, unfurls over two lush acres of meticulously manicured, fully fenced grounds. Upon entry, be enveloped in luxury as you traverse through spaces adorned with custom millwork, nine ft ceilings, abundant natural light and more. The heart of this home is an eat-in chef's kitchen, replete with top-tier stainless steel appliances, which connects you to multiple other spaces for enjoyment or repose. Entertain with panache in the formal dining room, garden room, library, living room or great room. Five fireplaces spread across this generous layout hosting five bedrooms- all ensuite- plus additional oversized office/media room with kitchenette, as well as third floor rec room with attached full bath and access to boutique-style cedar closet. Outdoors, a resplendent oasis awaits, featuring a pristine gunite with pebble sheen pool, granite heat resistant patio and an exquisite pool house with kitchenette and full bath, and expansive stone outdoor kitchen- a sublime setting for al fresco gatherings. A lifestyle of unparalleled elegance and comfort is a given. Every detail of this meticulously maintained home harmonizes to create an estate that epitomizes refined living. This majestic manor reflects pride in ownership and a timelessness that commands to be experienced.

Key Facts

City/Town
Fairfield
Neighborhood
Greenfield Hill
Property / Style
Single Family · Colonial
Year Built
1998
Days on Market
276 days
Beds
5
Baths
6 full · 1 half
Living Area
7,269 sq ft
Lot Size
2.03 acres
Garage / Parking
3 garage
Property Taxes
$37,387 / Annually

Market Snapshot

The Fairfield Market

Single Family · trailing 12 months

View area

Median Days on Market

33

88 active listings

Median $ / Sq Ft

$496

88 active listings

Sale-to-List Ratio

101.9%

567 sales

How this home compares

List Price

$2.80M

vs $1.59M median

76.4% above median

Price / Sq Ft

$385

vs $496 median

22.4% below median

Days on Market

276 days

vs 33 days median

243 days longer than median

Based on 88 active and 567 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of July 27, 2026.

Location

342 Midlock Road, Fairfield, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$18,325

per month

  • Principal & Interest$14,276
  • Property Taxes$3,116
  • Insurance$933
  • HOA$0

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

Location

City/Town
Fairfield
Neighborhood
Greenfield Hill
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1998
New Construction
No/Resale
Living Area
7,269 sq ft

Schools

Elementary
Burr
High
Fairfield Warde

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Central AirZoned
Fireplaces
5
Laundry Location
upper level
Appliances
Gas CooktopGas RangeWall OvenMicrowaveRange HoodSubzeroDishwasherWasherDryerWine Chiller
Basement
FullUnfinished
Interior Features
Audio SystemAuto Garage Door OpenerCable - Pre-wiredCentral VacuumSecurity System

Exterior & Lot

Lot Size
2.03 acres
Zoning
AAA
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Beach Rights
Water Source
Public Water Connected
Sewer
Septic
Pool
GuniteHeatedPool HouseSafety FenceSolar CoverIn Ground Pool
Construction
Clapboard
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Fence - FullTreedLevel LotOn Cul-De-SacProfessionally Landscaped

Listing & Financials

Property Taxes
$37,387 / Annually
Days on Market
276
MLS #
24134949
MLS Status
Under Contract

Similar Properties

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

Listed By

AJ Letterman

(203) 218-0604

Compass Connecticut, LLC

(203) 343-0141

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. 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 7/27/2026 at 6:10 PM UTC.