Features & Amenities

Interior

  • Other Interior Features

    Ceiling Fan(s)

  • Total Bedrooms

    6

  • Bathrooms

    5

  • 1/2 Bathrooms

    1

  • Above Grade Finished Area

    2666.0

  • Basement YN

    NO

  • Cooling YN

    YES

  • Cooling

    Central Air, Ceiling Fan(s), Zoned, Electric

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Exhaust Fan, Electric, Heat Pump

  • Main Level Bedrooms

    2

  • Pet friendly

    Yes

Exterior

  • Garage

    No

  • Construction Materials

    Frame

  • Other Exterior Features

    Balcony, Rain Gutters

  • Parking

    Asphalt, Off Street, Gravel

  • Patio and Porch Features

    Deck, Porch

  • Pool

    No

  • Waterfront YN

    YES

  • View

    Water, Ocean, Panoramic

Area & Lot

  • Lot Features

    Corner Lot, Waterfront

  • Lot Size(acres)

    0.11

  • Lot Size(square feet)

    5,000

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Coastal, Contemporary

Price

  • Sales Price

    $4,795,000

  • Tax Amount

    $6,705.2

  • Financing Options

    Conventional, Cash

  • Sq. Footage

    2,666

  • Price/SqFt

    $1,798

HOA

  • Association

    No

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • New Construction

    NO

  • Foundation Details

    Slab

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Water Source

    Public

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Listing Courtesy of SHAUN TULL , Jack Lingo - Rehoboth

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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.

2 CHICAGO STREET

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Related Properties

New on site 1 day ago
105 Chicago Street, Dewey Beach, DE 
Experience exceptional coastal living in this stunning 7-bedroom, 7-bathroom luxury home, ideally located just steps from the beach in the heart of Dewey Beach. Designed for comfort, entertaining, and multi-generational living, this remarkable property offers expansive indoor and outdoor spaces with high-end finishes throughout.
The highlight of the home is the spacious rooftop deck, where you can entertain guests, soak up the sun, or simply unwind while enjoying beautiful panoramic beach views. Just minutes from both Dewey Beach and Rehoboth Beach, you'll have easy access to award-winning restaurants, boutique shopping, nightlife, and everything the Delaware beaches have to offer.
Inside, you'll find a thoughtfully designed floor plan featuring a gourmet kitchen with premium stainless steel appliances, a second kitchen for added convenience, a butler's pantry, breakfast area, wine storage, wet bar, and generous dining and living spaces. The home also offers an elevator, entry-level bedroom, family room off the kitchen, walk-in closets, upgraded countertops, wood flooring, recessed lighting, intercom, whole-home sound system, and luxurious primary suites with spa-inspired baths, including jetted tubs and oversized stall showers.
Three gas fireplaces with elegant glass doors create warm and inviting gathering spaces, while dual laundry areas on both the upper and lower levels provide everyday convenience.
Additional premium features include:
Energy-efficient appliances and tankless water heater
Air filtration system
Security system and smoke detectors
36-inch-plus wide hallways and an oversized 84-inch garage door for enhanced accessibility
Insulated six-panel doors and energy-efficient double-pane, vinyl-clad windows with screens
Ceiling fans, window treatments, and abundant storage throughout

The exterior is equally impressive, showcasing extensive hardscaping, professional landscaping with underground irrigation, exterior lighting, floodlights, gutter system, chimney caps, and an outdoor shower—perfect after a day at the beach. Multiple balconies, screened porches, and the expansive rooftop deck provide exceptional outdoor living spaces to enjoy coastal breezes and scenic views.
Property Highlights
7 Bedrooms
7 Bathrooms
Spacious rooftop deck with beautiful beach views
Gourmet kitchen plus second kitchen
Elevator
3 Gas fireplaces
Wine storage and wet bar
Multiple balconies and screened porch
Outdoor shower
Extensive hardscaping and irrigation system
No HOA pool to maintain
Prime location near Dewey Beach, Rehoboth Beach, restaurants, shopping, and local attractions
This extraordinary beach home combines luxury, functionality, and an unbeatable location, making it an exceptional primary residence, vacation retreat, or investment opportunity.
#DESU2116162

DEWEY BEACH

105 CHICAGO STREET

7 Beds

7 Baths

7,136 Sq.Ft.

$4,800,000

MLS#: DESU2116162

 - property

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