For sale

$3,995,000

Est. $22,754/mo —

•

4,596

sq ft

558 Pilottown Rd, Lewes, DE 19958

About this home

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!

Single-familyProperty Type

1850Year Built

0.41 acresLot Size

$869Price/Sq.Ft.

2 garage spacesParking

Listed by Lee Ann Wilkinson • Berkshire Hathaway HomeServices PenFed Realty

•302-645-6661 (broker)

Listing updated: Aug 24, 2026 at 04:59pm

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #DESU2103202

Payment calculator

$22,754 per month

Principal and interest$20,995

Property taxes

$294

HOA dues

Home insurance

$1,465

Utilities

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Next available date: Tuesday, September 1

Open houses

No upcoming open houses.

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Around this home

Schools

K - 12
Preschool & daycare

Shields (Richard A.) Elementary School

Public K-5 • Assigned • 0.8mi

9/10

Frederick D Thomas Middle School

Public 6-8 • Assigned • 1.9mi

Cape Henlopen High School

Public 9-12 • Assigned • 1.7mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

558 Pilottown Rd · $3,995,000

Strong offer

$3.88M and above

75% chance or better to win

Why $3.88M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 76 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Attic
Breakfast area
Ceiling fans
Double/dual staircase
Traditional floor plan
Master bathroom(s)
Wood floors
Walk-in shower
Tub/shower combination
Built-ins
Butler’s pantry
Crown moldings
Dining area
Exposed beams
Gourmet kitchen
Recessed lighting
Skylights
Upgraded countertops
Walk-in closets
Wet/dry bar
Central vacuum
Other

Bedrooms
Three bedrooms on the first upper level
One bedroom on the main level
Entry-level bedroom

Bathrooms
Three full bathrooms total
Two half bathrooms total
Two full bathrooms on the first upper level
One full bathroom on the main level
Two half bathrooms on the main level

Kitchen
Gourmet kitchen
Dishwasher
Disposal
Icemaker
Wall oven
Six-burner stove
Built-in microwave
Oven - double
Gas oven/range
Range hood
Refrigerator
Extra refrigerator/freezer
Stainless steel appliances

Laundry & utility
Washer and dryer included
Main floor laundry
Water heater
Central vacuum

Flooring
Hardwood
Tile/brick
Carpet

Heating & cooling
Heat pumps (zoned)
Propane heating (leased)
Central air (zoned)
Electric hot water
Circuit breakers

Sale and tax history for 558 Pilottown Rd

Sale History
Tax History

Date

Event

Price

BRIGHT MLS #DESU2103202

Jun 26, 2026

Price Changed

$3,995,000

$869/sq ft

Apr 21, 2026

Price Changed

$4,295,000

$935/sq ft

Mar 22, 2026

Price Changed

$4,595,000

$1,000/sq ft

Feb 12, 2026

Listed

$4,850,000

$1,055/sq ft

Feb 6, 2026

Coming Soon

$4,850,000

$1,055/sq ft

BRIGHT MLS #DESU140932

Aug 28, 2019

Sold

$1,900,000

$413/sq ft

Jun 12, 2019

Pending

—

Jun 3, 2019

Contingent

—

May 28, 2019

Listed

$1,989,500

$433/sq ft

+55

CLASSIC MODERN ON THE WATERFRONT! Luxury and history meet in this fantastic Pilottown Road treasure! Brilliant evolution shines in this impeccably restored property, which includes a picturesque waterfront parcel across the street, complete with 5 boat slips and wide-open views. Originally built in 1850 and known as "The Light Keeper's House, " this model property was renovated in 1890, again in the 1950s, and perfected in 2004. The home progressively revealed exposed beams, added crown mouldings and wide base boards, and two additions to the main home while retaining and preserving random width heart pine floors. Gourmet kitchen with Wolf 6-burner range, professional grade stainless appliances and brilliant counter tops bridges historic charm and modern expectations. Amazingly lush, large backyard too! Make this the summer you relax on one of several idyllic porches on the canal, or within beautiful curated gardens. Truly one of the absolute best of Lewes!

BRIGHT MLS #1001571794

Aug 17, 2018

Listing Removed

—

Mar 28, 2018

Listed

$2,095,000

$456/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$1,753 (−0.4%)

$253,400 + $163,300

$416,700

2025

$1,760 (−26.4%)

$253,400 + $163,300

$416,700

2024

$2,391

$253,400 + $163,300

$416,700

2023

$2,388 (+3.6%)

$6,000 + $42,500

$48,500

2022

$2,305 (+0.9%)

$6,000 + $42,500

$48,500

2021

$2,284 (+0.3%)

$6,000 + $42,500

$48,500

2020

$2,277 (+9.5%)

$6,000 + $42,500

$48,500

2019

$2,080 (+20.3%)

$6,000 + $42,500

$48,500

2018

$1,730 (−6.0%)

$6,000 + $42,500

$48,500

2017

$1,840 (+9.0%)

$6,000 + $42,500

$48,500

2016

$1,687 (+15.2%)

$6,000 + $42,500

$48,500

2014

$1,465

$6,000 + $42,500

$48,500

Public record

Public record
Zoning

Beds

—

Baths

—

Stories

—

Lot width

62 ft.

Lot depth

219 ft.

Lot size

0.31 Acres

Year renovated

—

Finished Sq. Ft.

—

Unfinished Sq. Ft.

—

Total Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Sussex County

APN

335-4.18-51.00

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 24, 2026.

R-2

Residential Low-Density Zone

Provide for residential development outside of the City's town center and beachfront area.; Maintain lots that will permit the efficient use of public water and sewer services.; Diversify the City's residential development pattern by providing an opportunity for lots larger than those found in or near the center of the City.

Permitted uses

Include but are not limited to:

Religious facility
Housing-Single unit
Infrastructure
Public service
Fire house
Police station
Recreation
Housing-Mobile home park
Park & open space

Climate risks

5/10 Flood Factor

Estimated 36-48% chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 101° expected this year, 18 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Lewes, DE • 19958

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

95/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.3 hrs

6.3 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 558 Pilottown Rd

$3,724,971

$270K under list price of $4.00M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $910K to $3.1M.

SOLD JUL 15, 2026
$3,062,500 Last sold price
4 beds5 baths3,255 sq ft
422 Burton Ave, Lewes, DE 19958
$72/sq ft
smaller lot
169 years newer
SOLD AUG 14, 2026
$1,525,000 Last sold price
5 beds4.5 baths4,207 sq ft
35 Filly Ln, Lewes, DE 19958
$507/sq ft
smaller lot
175 years newer
SOLD MAR 26, 2026
$910,000 Last sold price
6 beds5 baths4,001 sq ft
131 New Rd, Lewes, DE 19958
$642/sq ft
smaller lot
156 years newer
SOLD APR 13, 2026
$2,500,000 Last sold price
4 beds5 baths4,057 sq ft
225 2nd St, Lewes, DE 19958
$253/sq ft
smaller lot
146 years newer
SOLD JUL 28, 2026
$1,662,500 Last sold price
4 beds3.5 baths3,167 sq ft
420 Kings Hwy, Lewes, DE 19958
$344/sq ft
50 years older
SOLD JUL 24, 2026
$1,595,000 Last sold price
4 beds3.5 baths2,585 sq ft
312 Burton Ave, Lewes, DE 19958
$252/sq ft
smaller lot
153 years newer

Rental earnings

Est. $3,293 per month, based on comparable rentals

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