558 Pilottown Rd

Lewes, DE 19958

$4,850,000
Price
4
Beds
4,554 Sq. Ft.
$1,065 / Sq. Ft.
4,554
Sq. Ft.
$1,065
per Sq. Ft.
Coming SoonVirtual Tour
Coming SoonVirtual Tour
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a living room with furniture and a book shelf
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a living room with furniture and a large window
a bathroom with a granite countertop toilet sink and mirror
a dining room with furniture and window
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a living room with furniture and a fireplace
a kitchen with stainless steel appliances granite countertop sink stove and refrigerator
a kitchen with stainless steel appliances granite countertop a stove and a sink
a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
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a bedroom with furniture and a window
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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...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!
  1. Listed by Lee Ann Wilkinson • Berkshire Hathaway HomeServices PenFed Realty
    P: (302)-645-6664 leeann@leeanngroup.com

Property Details for 558 Pilottown Road

Tax ID Number
335-04.18-51.00
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Coastal
Levels/Stories
2
Furnished
No
LISTING UPDATED: 02/06/2026 04:59 PM

Property Details for 558 Pilottown Road

StatusComing Soon
MLS #DESU2103202
Days on Market-
Taxes$3,527 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1850
Lot Size0.41 AC / 17,891 SF
CountySussex County

Location

Listing Courtesy of Berkshire Hathaway HomeServices PenFed Realty
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Building Information for 558 Pilottown Road

Stories2Year Built1850Building Size-Lot Size0.41 AC / 17,891 SF

Payment Calculator

$23,932 per month

30 year fixed, 6.15% Interest

Principal and Interest

$23,638

Property Taxes

$294

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 558 Pilottown Road

Location
Location
  • In City Limits: Yes
  • School District Name: CAPE HENLOPEN
  • School District County ID: 300200396895
  • SchoolDistrictSource: Listing Agent
  • County: SUSSEX
  • MLS Area: Lewes Rehoboth Hundred (31009)
Waterfront / Water Access
Waterfront / Water Access
  • Water View: Yes
  • Water Access: Yes
  • Water Access Features: Personal Watercraft (PWC), Private Access, Boat - Powered
  • Water Oriented: Yes
  • Navigable Water: Yes
  • Tidal Water: Yes
  • Water Body Name: Lewes Rehoboth Canal
  • Water Body Type: Canal
  • Water Frontage In Feet: 62.0
  • Docks Count: 3
  • Dock Type and Features: Multiple Slip, Other
  • Dock/Slip Conveys Y/N: true
  • Dock/Slip Conveyance: Physical Dock/Slip Conveys
  • Slips Count: 5+
Association / Community Info
Association / Community Info
  • Senior Community: No
  • Association Recreation Fee Y/N: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Year Assessed: 2025
  • County Tax: $178
  • City Town Tax: $1,767
  • Clean Green Assessed: No
  • Land Use Code: 1 1
  • Historic: No
  • Zoning: TN
  • Tax Lot: 82
  • School Tax: $1,582
  • School Tax Payment Frequency: Annually
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 1
  • # Bathrooms Count Main Level: 3
  • # Bathrooms Full Main Level: 1
  • # Bathrooms Half Main Level: 2
All Upper Levels
  • # Bedrooms Count All Upper Levels: 3
  • # Bathrooms Count All Upper Levels: 2
  • # Bathrooms Full All Upper Levels: 2
Upper Level 1
  • # Bedrooms Count Upper Level: 3
  • # Bathrooms Count Upper Level: 2
  • # Bathrooms Full Upper Level: 2
Rooms
  • Room List: 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
  • Stories: Main, Upper 1
Rooms Information
Room 1
  • Room Type: Bonus Room
  • Room Level: Upper 2
  • Room Exists: Yes
  • Room Features: Flooring - Carpet
Room 2
  • Room Type: Foyer
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 3
  • Room Type: Sun/Florida Room
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Ceiling Fan(s), Flooring - Tile/Brick
Room 4
  • Room Type: Half Bath
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 5
  • Room Type: Dining Room
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Built-Ins, Flooring - Tile/Brick, Fireplace - Gas
Room 6
  • Room Type: Kitchen
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Breakfast Bar, Countertop(s) - Granite, Flooring - Tile/Brick, Kitchen - Propane Cooking, Skylight(s)
Room 7
  • Room Type: Other
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Countertop(s) - Granite, Flooring - HardWood, Wet Bar
Room 8
  • Room Type: Laundry
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Tile/Brick
Room 9
  • Room Type: Great Room
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Built-Ins, Cathedral/Vaulted Ceiling, Ceiling Fan(s), Fireplace - Wood Burning, Flooring - HardWood, Skylight(s)
Room 10
  • Room Type: Primary Bedroom
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Attached Bathroom, Ceiling Fan(s), Flooring - HardWood, Walk-In Closet(s)
Room 11
  • Room Type: Primary Bathroom
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Bathroom - Walk-In Shower, Flooring - Tile/Brick, Double Sink
Room 12
  • Room Type: Half Bath
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 13
  • Room Type: Office
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Built-Ins, Ceiling Fan(s), Flooring - HardWood
Room 14
  • Room Type: Media Room
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Ceiling Fan(s), Flooring - HardWood
Room 15
  • Room Type: Screened Porch
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Ceiling Fan(s)
Room 16
  • Room Type: Additional Bedroom
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Attached Bathroom, Balcony Access, Ceiling Fan(s), Flooring - HardWood
Room 17
  • Room Type: Full Bath
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Bathroom - Tub Shower, Flooring - Tile/Brick
Room 18
  • Room Type: Additional Bedroom
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 19
  • Room Type: Full Bath
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 20
  • Room Type: Additional Bedroom
  • Room Level: Upper 1
  • Room Exists: Yes
  • Room Features: Balcony Access, Flooring - HardWood
Room 21
  • Room Type: Library
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Built-Ins, Flooring - HardWood, Fireplace - Gas
Building Info
Building Info
  • Year Major Reno Remodel: 2005
  • Total Finished SQFT: 4,554.00
  • Total Finished SQFT Source: Estimated
  • Tax Total Finished SQFT: 442.00
  • Total SQFT: 4,554.00
  • Total SQFT Source: Estimated
  • Construction Materials: Stick Built, Cedar, Shake Siding
  • Roof: Architectural Shingle, Metal
  • Ext Main Mid-res: http://bright-media02.prd.brightmls.com/bright/images/0000/8045/1009/1618/804510091618_512_384_WM_QQVEU4mm40aV9QQA.jpg
  • Wall and Ceiling Types: Vaulted Ceilings
  • Flooring Type: Tile/Brick, Carpet, Hardwood
  • Foundation Details: Block, Crawl Space
  • Room and Floor: Bedrooms-Main Level-1, Bathrooms Full-Main Level-1, Bathrooms Half-Main Level-1, Bathrooms Half-Main Level-2, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2
  • # Bathrooms Full: 3
  • # Bathrooms Half: 2
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Estimated
  • Lot Size Dimensions: 62.22 x 219.05 x 60.94 x 215.96
  • Lot Dimensions Source: Estimated
  • Lot Features: Bulkheaded, Landscaping, Rear Yard
  • Road Surface Type: Paved
  • Road Responsibility: Public
  • Road Frontage Length: 62.00
  • Location Type: Canal
  • Parcel ID: 5213001
  • Additional Parcels: Yes
  • Addl Parcels Descrp: Canal Front Lot with Dock (TMP: 335-04.19-90.00); measuring 62.75 x 57.86 x 62.22 x 71.30. The lots together total 17,891 sqft
Parking
Parking
  • Type Of Parking: Off Street, Driveway, Attached Garage
  • Num of Attached Garage Spaces: 2
  • Driveway - # of Spaces: 3
  • Total Garage Spaces: 2
  • Off Street - # of Spaces: 5
  • Parking Features: Stone Driveway, Brick Driveway
  • Garage Features: Garage Door Opener
Interior Features
Interior Features
  • 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
  • Fireplace: Yes
  • Fireplaces Count: 3
  • Fireplace Features: Gas/Propane, Brick, Wood
  • 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
  • Accessibility Features: None
  • Security Features: Security System
  • Window Features: Skylights
  • Laundry Type: Main Floor
  • Virtual Tour URL Unbranded: https://vimeo.com/1162596612?share=copy&fl=sv&fe=ci
Exterior Features
Exterior Features
  • Exterior Features: Outbuilding(s), Extensive Hardscape, Chimney Cap(s), Secure Storage, Stone Retaining Walls, Underground Lawn Sprinkler
  • Outdoor Living Structures: Balcony, Deck(s), Patio(s), Porch(es), Screened
  • Pool: No Pool
  • Other Structures: Above Grade, Below Grade
Utilities
Utilities
  • Utilities: Cable TV Available
  • Heating: Yes
  • Cooling Type: Central A/C, Zoned
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s), Zoned
  • Heating Fuel: Propane - Leased
  • Hot Water: Electric
  • Water Source: Public
  • Sewer Septic: Public Sewer
  • Electric Service: Circuit Breakers
Confidential Data
Listing Office
  • List Agent AOR: Sussex County Association of REALTORS (DE)

Property History for 558 Pilottown Road

DateEvent & SourcePriceAppreciation
Aug 28, 2019

Closed

BRIGHT #DESU140932

$1,900,000—
Jun 2, 2019

Pending

BRIGHT #DESU140932

—
May 28, 2019

Listed (Active)

BRIGHT #DESU140932

$1,989,500—
May 23, 2019

Withdrawn

BRIGHT #1001571794

$2,095,000—
Mar 28, 2018

Listed (Active)

BRIGHT #1001571794

$2,095,000—
Jun 2, 2004

Closed (Public Record)

Public Record #277967354

$230,000—
DateEvent & SourcePrice
08/28/2019

Closed

BRIGHT #DESU140932

$1,900,000
06/02/2019

Pending

BRIGHT #DESU140932

—
05/28/2019

Listed (Active)

BRIGHT #DESU140932

$1,989,500
05/23/2019

Withdrawn

BRIGHT #1001571794

$2,095,000
03/28/2018

Listed (Active)

BRIGHT #1001571794

$2,095,000
06/02/2004

Closed (Public Record)

Public Record #277967354

$230,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 558 Pilottown Road

Taxable ValueLand$6,000Additions$42,500Total$48,500
Tax Record2025$1,760 ($147 / month)
Home Facts
Beds4Total Finished SqFt884 SqFtAbove Grade Finished SqFt884 SqFtStories2Lot Size13,578 SqFtStyleSingle Family ResidenceYear Built1850ZoningTNCountySUSSEXAPN335-4.18-51.00

Schools near 558 Pilottown Road

This home is within Cape Henlopen School District.
Rating
School
Type
Grades
Distance
Shields (Richard A.) Elementary School
Public - K to 5
Mariner Middle School
Public - 6 to 8
Cape Henlopen High School
Public - 9 to 12
Sussex Consortium
Public - PK to 12
Rating
School
Distance
Shields (Richard A.) Elementary School
PublicK to 5

Mariner Middle School
Public6 to 8

Cape Henlopen High School
Public9 to 12

Sussex Consortium
PublicPK to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 558 Pilottown Road, Lewes, DE 19958

558 Pilottown Road is a single family home Coming Soon in Lewes, DE 19958. This property is currently priced at $4,850,000. This listing's school district is Cape Henlopen School District. Nearby schools include Shields (Richard A.) Elementary School, Mariner Middle School and Cape Henlopen High School. 558 Pilottown Road is a 4-bed, 5-bath, 4,554 sqft single family home built in 1850.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Berkshire Hathaway HomeServices PenFed Realty

Based on information from one of the following Multiple Listing Services: BRIGHT, Greater LeHigh Valley Regional MLS, Greator Scranton Board of REALTORS® and Pocono Mountains Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by BRIGHT, Greater LeHigh Valley Regional MLS, Greator Scranton Board of REALTORS® and Pocono Mountains Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.