Pending
Price CutPrice Drop: $300K (10/07)
Sale Pending at 558 Pilottown Rd, Lewes, DE 19958 | MLS# DESU2103202 | Listing updated on 2026-10-07
Photo 1 of Sale Pending at 558 Pilottown Rd, Lewes, DE 19958 | MLS# DESU2103202 | Listing updated on 2026-10-07
Photo 2 of Sale Pending at 558 Pilottown Rd, Lewes, DE 19958 | MLS# DESU2103202 | Listing updated on 2026-10-07
Photo 3 of Sale Pending at 558 Pilottown Rd, Lewes, DE 19958 | MLS# DESU2103202 | Listing updated on 2026-10-07
Photo 4 of Sale Pending at 558 Pilottown Rd, Lewes, DE 19958 | MLS# DESU2103202 | Listing updated on 2026-10-07
138+
Beds Icon

Virtual Tour

Beds Icon

Street View

$3,995,000

Monthly Est:$19,885

  • Beds Icon4 Beds
  • Beds Icon
    5 Baths
  • Beds Icon4,596sqft

558 Pilottown Rd, Lewes, DE 19958

$19,885/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 1850

  • $-- HOA

  • 17,891 sqft lot

  • $869/sq.ft

Description

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!

  • Houzeo last checked: 4 minutes ago
  • Listing updated: October 7, 2026 at 6:19 pm
  • Listing Provided by: Lee Ann Wilkinson (302) 645-6664 | Berkshire Hathaway HomeServices PenFed Realty (302) 645-6661
  • Source: Bright MLS-NJ | MLS#: DESU2103202 Bright MLS-NJ

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Sussex De County

  • City

    Lewes

  • Neighborhood

    --

  • Year Built

    1850

  • HOA Fees

    -

  • Finished Area

    4,596 sqft

  • Lot Size

    17,891 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    DESU2103202

  • MLS Status

    PENDING-BRIGHT

  • Days on Market

    212

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 5

Interior

  • Cooling

    Central A/c, Zoned

  • Window Features

    Skylights

  • Appliances

    Dishwasher, Disposal, Icemaker, Oven Wall, Six Burner Stove, Washer, Water Heater, Built In Microwave, Central Vacuum, Dryer, Oven Double, Oven/range Gas, Range Hood, Refrigerator, Extra Refrigerator/freezer, Stainless Steel Appliances

  • Interior Features

    Attic, Breakfast Area, Entry Level Bedroom, Ceiling Fan(s), Double/dual Staircase, Floor Plan Traditional, Primary Bath(s), Wood Floors, Bathroom Walk In Shower, Bathroom Tub Shower, Built Ins, Butlers Pantry, Carpet, Crown Moldings, Dining Area, Exposed Beams, Kitchen Gourmet, Recessed Lighting, Skylight(s), Upgraded Countertops, Walk In Closet(s), Wet/dry Bar, Other

  • Flooring

    Tile/brick, Carpet, Hardwood

  • Exterior Features

    Outbuilding(s), Extensive Hardscape, Chimney Cap(s), Secure Storage, Stone Retaining Walls, Underground Lawn Sprinkler

  • Sewer

    Public Sewer

  • Heating

    Heat Pump(s), Zoned

Construction

  • Year Built

    Year Built: 1850

  • Home type

    Single Family Residence

  • Property Condition

    Excellent

  • Foundation Details

    Block, Crawl Space

  • Construction Materials

    Stick Built, Cedar, Shake Siding

  • Roof

    Architectural Shingle, Metal

  • Architectural Style

    Coastal

Utilities & Energy

  • Electric

    Circuit Breakers

  • Utilities

    Cable Tv Available

  • Fireplace Features

    Gas/propane, Brick, Wood

  • Security Features

    Security System

  • Parking Features

    Stone Driveway, Brick Driveway

  • Water Source

    Public

Other Features

  • Lot Features

    Bulkheaded, Landscaping, Rear Yard

  • Patio And Porch Features

    Balcony, Deck, Patio, Porch, Screened

  • Subdivision Name

    None Available

Price History

DateEventPrice

10/07/2026

Source: mls_logoBright MLS-NJ #DESU2103202

Pending

$3,995,000

$869/sqft

06/26/2026

Source: mls_logoBright MLS-NJ #DESU2103202

Listed for Sale

$3,995,000 -6.98%

$869/sqft

04/21/2026

Source: mls_logoBright MLS-NJ #DESU2103202

Price Decreased

$4,295,000 -6.53%

$935/sqft

03/22/2026

Source: mls_logoBright MLS-NJ #DESU2103202

Price Increased

$4,595,000 +6.98%

$1,000/sqft

02/12/2026

Source: mls_logoBright MLS-NJ #DESU2103202

Listed for Sale

$4,295,000 -11.44%

$935/sqft

Show more

Nearby Homes

Based on information from Bright MLS through Oct 10, 2026, 03:15PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

Advertising Broker: Joe Hawkins | Hawkins Real Estate Services