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558 Pilottown Rd, 
Lewes, DE 19958

$4,295,000


4

Beds


5

Baths


4,596

Sq Ft


Single Family

Active

Listed by

Lee Ann Wilkinson

Berkshire Hathaway HomeServices Penfed Realty, 3026456661

Last updated:

May 20, 2026, 01:44 PM

MLS#

DESU2103202

Source:

BRIGHTMLS

About This Home

558 Pilottown Rd

WATERFRONT HOME - ROOTED IN HISTORY Experience 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!

Home Facts

Single Family

5 Baths

4 Bedrooms

Built in 1850

Price Summary

4,295,000

$934 per Sq. Ft.

MLS #:

DESU2103202

Last Updated:

May 20, 2026, 01:44 PM

Added:

3 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

3

Interior

Living Area:

4,596 Sq. Ft.


Structure

Structure

Architectural Style:

Coastal

Building Area:

4,596 Sq. Ft.

Year Built:

1850


Lot

Lot Size (Sq. Ft):

17,859


Finances & Disclosures

Finances

Price:

$4,295,000

Price per Sq. Ft:

$934 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.
See this home in person
558 Pilottown Rd
Attend an upcoming open house
Sat, May 23
02:00 PM04:00 PM

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.