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For salePrice cut: $300K (6/26)
$3,995,000
4beds
4,596sqft

558 Pilottown Rd, Lewes, DE 19958

4beds
4,596sqft
Single family residence
Built in 1850
0.41 Acres
2 Attached garage spaces
$869 price/sqft

What's special

Waterfront homeCanal front parcelPanoramic viewsTwo soaring additionsFive private boat slipsPrivate sanctuaryClassic terracotta hex-tile flooring

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!

198 days
|
2,435
|
59
|
Source: Bright MLS,MLS#: DESU2103202MLS Logo
Travel times

Family Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Lee Ann Wilkinson 302-645-6664,

Berkshire Hathaway HomeServices PenFed Realty 3026456661,

Listing Team: The Lee Ann Wilkinson Group

Source: Bright MLS,MLS#: DESU2103202MLS Logo

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 4
  • Bathrooms: 5
  • Full bathrooms: 3
  • 1/2 bathrooms: 2
  • Main level bathrooms: 3
  • Main level bedrooms: 1
Rooms
  • Room types: 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, Additional Bedroom
Primary bedroom
  • Features: Attached Bathroom, Ceiling Fan(s), Flooring - HardWood, Walk-In Closet(s)
  • Level: Main
Other
  • Features: Attached Bathroom, Balcony Access, Ceiling Fan(s), Flooring - HardWood
  • Level: Upper
Other
  • Features: Flooring - HardWood
  • Level: Upper
Other
  • Features: Balcony Access, Flooring - HardWood
  • Level: Upper
Primary bathroom
  • Features: Bathroom - Walk-In Shower, Flooring - Tile/Brick, Double Sink
  • Level: Main
Bonus room
  • Features: Flooring - Carpet
  • Level: Upper
Dining room
  • Features: Built-in Features, Flooring - Tile/Brick, Fireplace - Gas
  • Level: Main
Foyer
  • Features: Flooring - HardWood
  • Level: Main
Other
  • Features: Bathroom - Tub Shower, Flooring - Tile/Brick
  • Level: Upper
Other
  • Features: Flooring - HardWood
  • Level: Upper
Great room
  • Features: Built-in Features, Cathedral/Vaulted Ceiling, Ceiling Fan(s), Fireplace - Wood Burning, Flooring - HardWood, Skylight(s)
  • Level: Main
Half bath
  • Features: Flooring - HardWood
  • Level: Main
Half bath
  • Features: Flooring - HardWood
  • Level: Main
Kitchen
  • Features: Breakfast Bar, Granite Counters, Flooring - Tile/Brick, Kitchen - Propane Cooking, Skylight(s)
  • Level: Main
Laundry
  • Features: Flooring - Tile/Brick
  • Level: Main
Library
  • Features: Built-in Features, Flooring - HardWood, Fireplace - Gas
  • Level: Main
Media room
  • Features: Ceiling Fan(s), Flooring - HardWood
  • Level: Upper
Office
  • Features: Built-in Features, Ceiling Fan(s), Flooring - HardWood
  • Level: Upper
Other
  • Features: Granite Counters, Flooring - HardWood, Wet Bar
  • Level: Main
Screened porch
  • Features: Ceiling Fan(s)
  • Level: Upper
Other
  • Features: Ceiling Fan(s), Flooring - Tile/Brick
  • Level: Main
Heating
  • Heat Pump, Zoned, Propane
Cooling
  • Central Air, Zoned, Electric
Appliances
  • Included: Dishwasher, Disposal, Ice Maker, Oven, Six Burner Stove, Washer, Water Heater, Microwave, Central Vacuum, Dryer, Double Oven, Oven/Range - Gas, Range Hood, Refrigerator, Extra Refrigerator/Freezer, Stainless Steel Appliance(s), Electric Water Heater
  • Laundry: Main Level, Laundry Room
Features
  • Attic, Breakfast Area, Entry Level Bedroom, Ceiling Fan(s), Double/Dual Staircase, Floor Plan - Traditional, Primary Bath(s), Bathroom - Walk-In Shower, Bathroom - Tub Shower, Built-in Features, Butlers Pantry, Crown Molding, Dining Area, Exposed Beams, Kitchen - Gourmet, Recessed Lighting, Upgraded Countertops, Walk-In Closet(s), Bar, Other, Vaulted Ceiling(s)
  • Flooring: Tile/Brick, Carpet, Hardwood, Wood
  • Windows: Skylight(s)
  • Has basement: No
  • Number of fireplaces: 3
  • Fireplace features: Gas/Propane, Brick, Wood Burning
Interior area
  • Total structure area: 5,130
  • Total interior livable area: 4,596 sqft
  • Finished area above ground: 4,596
  • Finished area below ground: 0
Video & virtual tour

Property

Parking
  • Total spaces: 10
  • Parking features: Garage Door Opener, Driveway, Off Street, Attached
  • Attached garage spaces: 2
  • Uncovered spaces: 3
Accessibility
  • Accessibility features: None
Features
  • Levels: Two
  • Stories: 2
  • Patio & porch: Deck, Patio, Porch, Screened, Screened Porch
  • Exterior features: Extensive Hardscape, Chimney Cap(s), Storage, Stone Retaining Walls, Underground Lawn Sprinkler, Balcony
  • Pool features: None
  • Has view: Yes
  • View description: Canal, Water, Panoramic, Garden
  • Has water view: Yes
  • Water view: Canal,Water
  • Waterfront features: Private Dock Site, Canal, Personal Watercraft (PWC), Private Access, Boat - Powered
  • Body of water: Lewes Rehoboth Canal
  • Frontage length: Road Frontage: 62,Water Frontage Ft: 62
Lot
  • Size: 0.41 Acres
  • Dimensions: 62.22 x 219.05 x 60.94 x 215.96
  • Features: Bulkheaded, Landscaped, Rear Yard
Details
  • Additional structures: Above Grade, Below Grade, Outbuilding
  • Additional parcels included: Canal Front Lot with Dock (TMP: 33504.1990.00); measuring 62.75 x 57.86 x 62.22 x 71.30. The lots together total 17,891 sqft
  • Parcel number: 33504.1851.00
  • Zoning: TN
  • Special conditions: Standard

Construction

Type & style
  • Home type: SingleFamily
  • Architectural style: Coastal
  • Property subtype: Single Family Residence
Materials
  • Stick Built, Cedar, Shake Siding
  • Foundation: Block, Crawl Space
  • Roof: Architectural Shingle,Metal
Condition
  • Excellent
  • New construction: No
  • Year built: 1850
  • Major remodel year: 2005

Utilities & green energy

  • Electric: Circuit Breakers
  • Sewer: Public Sewer
  • Water: Public
  • Utilities for property: Cable Available

Community & HOA

Community
  • Security: Security System
  • Subdivision: None Available
HOA
  • Has HOA: No
Location
  • Region: Lewes

Financial & listing details

  • Price per square foot: $869/sqft
  • Tax assessed value: $833,400
  • Annual tax amount: $3,527
  • Date on market: 2/12/2026
  • Listing agreement: Exclusive Right To Sell
  • Listing terms: Cash,Conventional
  • Exclusions: Dining Room Chandelier, Black Chandelier In Back Stairway Leading To 2nd Floor, Primary Bedroom Curtains, Tesla Charger In Garage
  • Ownership: Fee Simple
  • Road surface type: Paved

Price history

DateEventPrice
6/26/2026Price change$3,995,000-7%$869/sqft
Source: Bright MLS #DESU2103202 Report a problem
4/21/2026Price change$4,295,000-6.5%$935/sqft
Source: Bright MLS #DESU2103202 Report a problem
3/22/2026Price change$4,595,000-5.3%$1,000/sqft
Source: Bright MLS #DESU2103202 Report a problem
2/12/2026Listed for sale$4,850,000+155.3%$1,055/sqft
Source: Bright MLS #DESU2103202 Report a problem
8/28/2019Sold$1,900,000-4.5%$413/sqft
Source: Public Record Report a problem
6/3/2019Pending sale$1,989,500$433/sqft
Source: BERKSHIRE HATHAWAY HOMESERVICES GALLO-L #DESU140932 Report a problem
5/29/2019Listed for sale$1,989,500-5%$433/sqft
Source: BERKSHIRE HATHAWAY HOMESERVICES GALLO-L #DESU140932 Report a problem
8/17/2018Listing removed$2,095,000$456/sqft
Source: BERKSHIRE HATHAWAY HOMESERVICES GALLO-L #1001571794 Report a problem
3/28/2018Listed for sale$2,095,000$456/sqft
Source: BERKSHIRE HATHAWAY HOMESERVICES GALLO-L #729036 Report a problem

Public tax history

YearProperty taxesTax assessment
2025$1,760 -26.4%$416,700 +759.2%
2024$2,391 +0.1%$48,500
2023$2,388 +3.6%$48,500
2022$2,305 +0.9%$48,500
2021$2,284 +0.3%$48,500
2020$2,277 $48,500
2019$2,277 +9.5%$48,500
2018$2,080 +7.8%$48,500
2017$1,930 +14.4%$48,500
2016$1,687 +5.4%$48,500
2015$1,601 +9.3%$48,500
2014$1,465 +2.8%$48,500
2013$1,425 +0.5%$48,500
2012$1,418 +10.6%$48,500
2011$1,282 $48,500
2010$1,282 -2.8%$48,500
2009$1,318 $48,500
2008-- --
2007-- --
2006-- --
2005-- --
2004-- --
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2002-- --
2001-- --

Find assessor info on the county website

Monthly payment

Est. payment
$21,701/mo
Principal & interest
$20602
Property taxes
$1099
More affordability toolsChevron Right

Estimated market value

$3,687,600

$3.50M - $3.87M

$3,729/mo

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: 19958

Nearby schools

Shields (Richard A.) Elementary School
Grades K-5 • 0.9 miles
9/10
GreatSchools® Rating
Test Score Rating
8/10
Student Progress Rating
9/10
Frederick D Thomas Middle School
Grades 6-8 • 1.9 miles
N/A
GreatSchools® Rating
Test Score Rating
9/10
Cape Henlopen High School
Grades 9-12 • 1.7 miles
8/10
GreatSchools® Rating
College Readiness Rating
8/10

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