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Lewes 19958
558 PILOTTOWN ROAD
$3,995,000
● House - In Contract

558 PILOTTOWN ROAD

LEWES, DE 19958
bedrooms
4 Beds
bathrooms
3 Baths, 2 Half Baths
square feet
4,596 Ft²
$19,911
Est. Monthly

About This Property

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!
Unit Size
4,596 Ft²
Days on Market
-
Land Size
0.41 acres
Price per sqft
$869
Property Type
House
Property Taxes
$294
HOA Dues
-
Year Built
-

Listed By

Lee Ann Wilkinson
Berkshire Hathaway HomeServices PenFed Realty

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Last updated: 2 months ago (Bright MLS #DESU2103202)

Price History

Date / Event Date Event Price
Sep 12, 2026 In contract -
In contract
Jun 26, 2026 Price Decreased $3,995,000
↓ $300K (7%)
Price Decreased
Apr 21, 2026 Price Decreased $4,295,000
↓ $300K (6.5%)
Price Decreased
Mar 22, 2026 Price Decreased $4,595,000
↓ $255K (5.3%)
Price Decreased
Feb 12, 2026 Listed by Berkshire Hathaway HomeServices PenFed Realty $4,850,000
Listed by Berkshire Hathaway HomeServices PenFed Realty
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Property Highlights

Parking Available
Garage
Air Conditioning
Fireplace
With View
Parking Details
Has Garage
Has Open Parking
Parking Features: Driveway, Off Street, Attached, Garage, Brick Driveway
Garage Spaces: 2
Interior Details
Half Bathrooms: 2
Full Bathrooms: 3
Interior Features: Breakfast Bar, Ceiling Fan(s), Built-in Features, Crown Molding, Recessed Lighting, Walk-In Closet(s), Dry Bar, Other, Attic, Entry Level Bedroom, Double/Dual Staircase, Floor Plan - Traditional, Primary Bath(s), Wood Floors, Bathroom - Walk-In Shower, Bathroom - Tub Shower, Butlers Pantry, Carpet, Dining Area, Exposed Beams, Kitchen - Gourmet, Skylight(s), Upgraded Countertops
Appliances: Dishwasher, Disposal, Ice Maker, Washer, Water Heater, Microwave, Dryer, Double Oven, Gas Oven, Range Hood, Refrigerator, Stainless Steel Appliance(s), Oven - Wall, Six Burner Stove, Central Vacuum
Flooring Type: Brick, Carpet, Hardwood
Rooms: 8
Has Fireplace
Fireplace Features: Propane, Brick, Wood
Fireplaces: 3
Exterior Details
Square Footage: 4596
Square Footage Source: $0
Security Features: Security System
Property Condition: Excellent
Architectural Style: Coastal
Year Built Source: Assessor
Year Built: 1850
Waterfront Features: Private Dock Site
Waterbody Name: Lewes Rehoboth Canal
Building Name: NONE AVAILABLE
Levels: 2
Other Structures: Above Grade, Below Grade
Window Features: Skylight(s)
Construction Materials: Cedar, Shake Siding, Stick Built
Patio and Porch Features: Deck, Patio, Porch, Screened, Balcony
Lot Features: Bulkheaded, Landscaping, Rear Yard
Lot Size Area: 17891
Lot Size Units: Square Feet
Lot Size Acres: 0.41
Lot Size Square Feet: 17891
Lot Size Dimensions: 62.22 x 219.05 x 60.94 x 215.96
Tax Lot: 82
Water Source: Public
Financial Details
Tax Annual Amount: $3,527
Utilities Details
Cooling Type: Central Air, Zoned
Heating Type: Zoned, Heat Pump(s)
Sewer : Public Sewer

Building Info

Overview

    General

  • Bedroom Count: 0
  • Building Condition: 0
  • Building Quality: 0
  • Construction Type: 0
  • Building Style: 0
  • Exterior Walls Type: 0
  • Interior Walls Type: 0
  • Roof Shape Type: 0
  • Roof Cover Type: 0
  • Floor Cover: 0
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 0
  • Parking Space Count: 0
  • Patio Type: 0
  • Porch Type: 0
  • Pool Type: 0

    Dimensions

  • Lot Size Square Feet: 13,578
  • Lot Size Depth Feet: 2,190
  • Lot Size Frontage Feet: 620
  • Total Building Area: 0
  • Building Area: 0

    Heating and Cooling

  • Air Conditioning: 0
  • Heating: 0
  • Heating Fuel Type: 0

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: LEWES
  • Land Acres: 0000000312
  • Standard Land Use Code: 1001
  • County Land Use Code: RS
  • Legal Description 1: PILOT TOWN RD LOT

Neighborhood

  • School District Name: Cape Henlopen School District
  • School Tax School District: CAPE HENLOPEN
  • Census Tract: 050903

Zoning

  • Zoning: TN

Geography

  • District: CAPE HENLOPE
  • Parcel: 335-4.18-51.00
  • Municipality: 19958
  • Latitude: 38.7818
  • Longitude: -75.1548

    Address

  • Full Address: 558 Pilottown Rd
  • Address - House Number: 558
  • Address - Street Name: Pilottown
  • Address - Suffix Type: Rd
  • State: DE
  • City Name: Lewes
  • Carrier Code: C002
  • 4-Digit Zip Code: 1248
  • Zip Code: 19958

Valuation

    Tax

  • Tax Year: 2023
  • Tax Amount: $238,844

    Appraisal Valuation

  • Standard Deviation: 0.2431
  • Valuation Date: Nov 08, 2023
  • Confidence Score: 65
  • Final Value: 1,870,020
  • High Value: 2,324,764
  • Low Value: 1,415,277

    Market Valuation

  • Market Total Value: $97,000
  • Market Land Value: $12,000
  • Market Improvement Value: $85,000

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $48,500
  • Assessed Land Value: $6,000
  • Assessed Improvements Value: $42,500

    Sales

  • Current Sale Contract Date: Aug 28, 2019
  • Current Sale Recording Date: Aug 28, 2019
  • Current Sale Price:
  • Current Sale Document Type: 27
  • Current Sale Input Document Number: 20190000031495

    Financing

  • First Mortgage Financing Type: ADJ
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Lewes


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Frequently Asked Questions

When was property at 558 Pilottown Road built and last sold?
The property at 558 Pilottown Road was built in and last sold on Aug 28, 2019 for $1,900,000.
How much is this home worth?
The estimated value of the home located at 558 Pilottown Road is $3,954,044.
What are some comparable homes to 558 Pilottown Road?
There are currently no comparable homes to 558 Pilottown Road.