1. Delaware
  2. Dewey Beach
  3. 2 CHICAGO ST
$5,400,000

2 CHICAGO ST, Dewey Beach, DE 19971

  • 6 beds |
  • 6 baths |
  • 2,666 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1988
  • Property Lot Size Icon4,792sqft lot
  • Property Parking Icon —— car garage
  • Property Price Per Square Feet Icon $2,026/sqft
  • Property List Date Icon Listed 9 days ago

Property Description

Rare oceanfront opportunity in Rehoboth by the Sea. Discover unparalleled coastal living at 2 Chicago Street, an oceanfront retreat in the highly coveted community of Rehoboth by the Sea on the north end of Dewey Beach. This exceptional 6-bedroom, 5.5-bath home offers sweeping panoramic views from nearly every room, with a private dune crossover that leads directly to the wide, sandy beach. The first level welcomes you with a bright entry foyer, two bedrooms (including a flexible oceanfront space ideal for a den, exercise room, or guest suite), two full baths, and a convenient laundry room. Upstairs, the recently updated kitchen shines with quartz counters, stainless steel appliances, and custom cabinetry, seamlessly flowing into the dining and living areas—all framed by walls of windows showcasing endless ocean vistas. Step outside to the expansive oceanfront deck, perfect for sunrises, gatherings, and salty breezes. A private office with sweeping north-facing views completes this level. On the third floor, you’ll find four additional bedrooms and three full baths, including the oceanfront primary suite with its own balcony for uninterrupted sunrise views. The rooftop deck crowns the home, offering a bird’s-eye view of the coastline—an unforgettable setting for stargazing or enjoying fireworks on July 4th. Rehoboth by the Sea is one of the Delaware coast’s most sought-after neighborhoods, known for its wide beaches, relaxed atmosphere, and close proximity to both Rehoboth and Dewey Beach attractions. Currently, 2 Chicago Street stands as the only oceanfront property available in either community—making this a truly rare opportunity to own a piece of coastal paradise.

Listing Status:
Active
Date Added:
September 26, 2025 at 05:00AM
Listing Office:
Jack Lingo - Rehoboth : 3022273883
Listing Agent:
SHAUN TULL : 3022266417
MLS ID:
DESU2077352
  • General: Ceiling Fan(s)Window TreatmentsCombination Kitchen/DiningPrimary Bedroom - Ocean FrontUpgraded CountertopsWood Floors
  • Appliances: Exhaust FanRange HoodOven/Range - ElectricDishwasherDisposalDryerMicrowaveWasherRefrigeratorIcemaker
  • Laundry: Lower Floor
  • Flooring: Ceramic tileWood
  • A/C: Central A/CZoned
  • Heating: Heat Pump(s)Electric
  • Fireplace: FireplaceFireplaces: 1
  • Disability Feature: None
  • Eco/Green Feature: PV Solar Array(s) Owned
  • General: Gutter SystemOutside ShowerRoof DeckAbove GradeBelow Grade
  • Style: CoastalContemporary
  • Other Structures: RoofPorchBalconyDeck
  • Parking: Asphalt DrivewayCrushed Stone
  • Roofing: Metal
  • Windows: Bay bowDouble hung
  • General: Frame3Slab
  • Originating MLS: BRIGHT_MAIN
  • School District: CAPE HENLOPEN
  • County: SUSSEX-DE
  • Zoning: TN334-20.14-156.00
  • View: OceanPanoramic
  • Waterfront: 50
  • Utilities: Cable tvSewer availableWater available200 amp service
  • Water: Public
  • Sewer: Public Sewer
  • Source: BRIGHT_MAIN
  • Exclusions: Artworksome furnitureand staging items

This listing courtesy of SHAUN TULL, Jack Lingo - Rehoboth

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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Location

Schools Nearby

R

Rehoboth Elementary School

500 Stockley St, Rehoboth Beach, DE, 19971

Grades KG-5

1.00 miles away

B

Beacon Middle School

19483 John J Williams Hwy, Lewes, DE, 19958

Grades 6-8

4.15 miles away

C

Cape Henlopen High School

1250 Kings Hwy, Lewes, DE, 19958

Grades 9-12

5.70 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.

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#DESU2087390 - Jack Lingo - Rehoboth