558 Pilottown Road Lewes, DE 19958

Property Photo: 558 Pilottown Road DE 19958

Listing Courtesy of: BRIGHT IDX / Listed By: Berkshire Hathaway Homeservices Penfed Realty

558 Pilottown Road Lewes, DE 19958

Active (208 Days)

$3,995,000 ^(USD)

BED

BATH

4,596

SQFT

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Description

WATERFRONT HOME - ROOTED IN HISTORYExperience the brilliant evolution of The Light Keeper’s House, an impeccably restored 1850s treasure on historic Pilottown Road. This architectural masterpiece seamlessly blends luxury and history, and includes the canal front parcel directly across the street complete with five private boat slips and wide-open scenic views. Thoughtfully renovated through the centuries and perfected in 2004, the residence retains its soul with preserved random-width heart pine floors and authentic exposed beams, while introducing two soaring additions that flood the home with natural light through vaulted ceilings and skylights.The interior is a masterclass in coastal sophistication, centered around a gourmet chef’s kitchen equipped with a Wolf 6-burner professional range, premium stainless appliances, and a striking emerald-tiled backsplash. Elegant entertaining flows from the formal dining room, anchored by a massive white-washed masonry fireplace, to the sun-drenched sun room featuring classic terracotta hex-tile flooring and panoramic views. A fully equipped butler’s pantry with a wine cooler and additional prep space ensures seamless hosting for gatherings of any size.The grand living spaces are defined by impeccable craftsmanship, including added crown moldings, wide baseboards, and a stately brick fireplace in the Great Room. Upstairs, the expansive double-decker porches offer a front-row seat to the salt air and the gentle rhythm of the canal. The lifestyle continues outdoors in the amazingly lush, oversized backyard & curated gardens, creating a private sanctuary that is a rare find in the heart of Lewes.This is a peerless offering where historic charm meets modern luxury in one of the absolute best locations in Delaware. From the professional-grade culinary heart of the home to the five private slips waiting for your fleet, every detail of this property has been polished to perfection. Don’t miss this chance to own a piece of maritime history in the first town of the first state!

MLS #:
DESU2103202

Taxes
$3,527(2025)

Lot Size
0.41 acres

Type
Single-Family Home

Building Name
None Available

Year Built
1850

Style
Coastal

School District
Cape Henlopen

County
Sussex County

Listed By

Lee Ann Wilkinson, Lewes East

Source
BRIGHT IDX
Last checked Sep 7 2026 at 8:25 AM EDT

Bathroom Details

Full Bathrooms: 3
Half Bathrooms: 2

Interior Features

Dining Area
Built-Ins
Crown Moldings
Wood Floors
Floor Plan - Traditional
Central Vacuum
Dishwasher
Disposal
Dryer
Extra Refrigerator/Freezer
Washer
Refrigerator
Oven - Wall
Water Heater
Icemaker
Oven - Double
Entry Level Bedroom
Oven/Range - Gas
Breakfast Area
Kitchen - Gourmet
Upgraded Countertops
Recessed Lighting
Range Hood
Six Burner Stove
Butlers Pantry
Double/Dual Staircase
Wet/Dry Bar
Walls/Ceilings: Vaulted Ceilings
Other
Skylight(s)
Exposed Beams
Built-In Microwave
Stainless Steel Appliances
Attic
Carpet
Walk-In Closet(s)
Ceiling Fan(s)
Primary Bath(s)
Bathroom - Tub Shower
Bathroom - Walk-In Shower

Lot Information

Landscaping
Bulkheaded
Rear Yard

Property Features

Above Grade
Below Grade
Fireplace: Gas/Propane
Fireplace: Wood
Fireplace: Brick
Foundation: Crawl Space
Foundation: Block

Heating and Cooling

Heat Pump(s)
Zoned
Central A/C

Flooring

Tile/Brick
Hardwood
Carpet

Exterior Features

Cedar
Shake Siding
Stick Built
Roof: Metal
Roof: Architectural Shingle

Utility Information

Utilities: Cable Tv Available
Sewer: Public Sewer
Fuel: Propane - Leased

Parking

Brick Driveway
Stone Driveway

Stories

Living Area

4,596 sqft

Listing Price History

Date

Event

Price

% Change

$ (+/-)

Jun 26, 2026

Price Changed

$3,995,000

-7%

-$300,000

Apr 21, 2026

Price Changed

$4,295,000

-7%

-$300,000

Mar 22, 2026

Price Changed

$4,595,000

-5%

-$255,000

Location

Map View | Street View

Listing to Address

Address to Listing

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Disclaimer: Copyright 2026 Bright MLS IDX. All rights reserved. This information is deemed reliable, but not guaranteed. The information being provided is 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. Data last updated 9/7/26 01:25

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