About 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!
Features of 558 Pilottown Rd
| MLS® # | DESU2103202 |
|---|---|
| Price | $4,850,000 |
| Bedrooms | 4 |
| Bathrooms | 4.00 |
| Full Baths | 3 |
| Half Baths | 2 |
| Square Footage | 4,596 |
| Acres | 0.41 |
| Year Built | 1850 |
| Type | Residential |
| Sub-Type | Detached |
| Style | Coastal |
| Status | Active |
Community Information
| Address | 558 Pilottown Rd |
|---|---|
| Area | Lewes Rehoboth Hundred |
| Subdivision | NONE AVAILABLE |
| City | LEWES |
| County | SUSSEX-DE |
| State | DE |
| Zip Code | 19958 |
Amenities
| Amenities | Attic, Entry Level Bedroom, Ceiling Fan(s), Double/Dual Staircase, Primary Bath(s), Wood Floors, Bathroom - Walk-In Shower, Bathroom - Tub Shower, Built-Ins, Butlers Pantry, Carpet, Crown Moldings, Exposed Beams, Recessed Lighting, Skylight(s), Upgraded Countertops, Walk-in Closet(s), Wet/Dry Bar |
|---|---|
| Utilities | Cable TV Available |
| Parking | Stone Driveway, Brick Driveway |
| # of Garages | 2 |
| Garages | Garage Door Opener |
| View | Canal, Water, Panoramic, Garden/Lawn |
| Is Waterfront | Yes |
| Waterfront | Canal |
Interior
| Interior Features | Floor Plan - Traditional |
|---|---|
| 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 |
| Heating | Heat Pump(s), Zoned |
| Cooling | Central A/C, Zoned |
| Fireplace | Yes |
| # of Fireplaces | 3 |
| Fireplaces | Gas/Propane, Brick, Wood |
| Stories | 2 |
| Has Basement | No |
Exterior
| Exterior | Cedar, Shake Siding |
|---|---|
| Exterior Features | Outbuilding(s),Extensive Hardscape,Chimney Cap(s),Secure Storage,Stone Retaining Walls,Underground Lawn Sprinkler,Balcony,Deck(s),Patio(s),Porch(es),Screened |
| Lot Description | Bulkheaded, Landscaping, Rear Yard |
| Windows | Skylights |
| Roof | Architectural Shingle, Metal |
| Construction | Stick Built, Cedar, Shake Siding |
| Foundation | Block, Crawl Space |
School Information
| District | CAPE HENLOPEN |
|---|
Additional Information
| Date Listed | February 12th, 2026 |
|---|---|
| Days on Market | 34 |
| Zoning | TN |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | Berkshire Hathaway HomeServices PenFed Realty |
|---|---|
| Contact Info | 3026456661 |