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558 Pilottown Road, Lewes, DE 19958

$3,995,000
  • 558 Pilottown Road, Lewes, DE 19958 Main Photo

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PENDING Price Reduced by $300,000 on October 11th, 2026
BEDS4 BATHS3 full 2 partial SQUARE FEET4,596 MLS#DESU2103202
STATUSPENDING PROPERTY TYPEResidential - Single Family SCHOOLCAPE HENLOPEN

Property 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!

558 Pilottown Road | MLS# DESU2103202

This single family home located at 558 Pilottown Road, Lewes, DE 19958 is currently listed for sale with an asking price of $3,995,000. This property was built in 1850 and has 4 bedrooms and 3 full and 2 partial baths with 4596 sq. ft. Pilottown Road is located within the CAPE HENLOPEN school district. Search Lewes real estate on www.homesaleluxury.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central A/C, Zoned
Fireplaces: 3
Fuel Type: Propane - Leased
Garage: 2
Heating: Heat Pump(s), Zoned
Home Style: Coastal
Lot Size: 0.41 Acres
Roof Type: Architectural Shingle, Metal
Stories: 2.0
Taxes: $3,527
Year Built: 1850

Feature Descriptions

Additional Structures: Above Grade, Below Grade
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
Building Name: NONE AVAILABLE
Electric: Circuit Breakers
Exterior: Stick Built, Cedar, Shake Siding
Exterior: Outbuilding(s), Extensive Hardscape, Chimney Cap(s), Secure Storage, Stone Retaining Walls, Underground Lawn Sprinkler
Fireplace: Gas/Propane, Brick, Wood
Flooring: Tile/Brick, Carpet, Hardwood
Interior: 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
Lake Name: Lewes Rehoboth Canal
Location: Canal
Lot: Bulkheaded, Landscaping, Rear Yard
Lot Dimensions: 0.41 Acre(S)
Number of Rooms: 8
Parking Features: Stone Driveway, Brick Driveway
Parking Notes: 10 Total Parking Spaces
Rooms: Dining Room, Primary Bedroom, Kitchen, Library, Foyer, Sun/Florida Room, Great Room, Laundry, Other, Office, Media Room, Bonus Room, Primary Bathroom, Full Bath, Half Bath, Screened Porch, Additional Bedroom
Sewer: Public Sewer
Special View Info: Canal, Water, Panoramic, Garden/Lawn
SQFT Above Finished: 4596
SQFT Total Finished: 4596
Structure Type: Detached
Total Garage/Parking Spaces: 10
Utilities: Cable TV Available
Water: Public
Water Access: Personal Watercraft (PWC), Private Access, Boat - Powered
Waterfront: Private Dock Site
Windows: Skylights

Local Schools

School District: CAPE HENLOPEN

Listed By / Shown By

Listed By

Agency Name: Berkshire Hathaway HomeServices PenFed Realty
Agency Phone: 3026456661

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Estimated Payment

$ 22,722.19 per month $21,263.07 Principal & Interest $293.92 Property Tax $1,165.21 Homeowner's Insurance

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