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.
2,666 Sq Ft
5,000 Sq Ft Lot Size
Other
$6,705 Annual Tax
Built in 1988
MLS/Listing ID DESU2077352
NONE AVAILABLE
Dishwasher
Disposal
Dryer
Exhaust Fan
Ice Maker
Microwave
Range Hood
Refrigerator
Washer
Style - Coastal
Ceiling Fans
Upgraded Countertops
Metal
Style - Contemporary
Construction - Frame
Cooling - Zoned
Cooling - Central Air
Natural Wood
Ceramic Tile
Slab
Heating - Electric
Window Treatments
Balcony
Double Hung
Pets Allowed
TOTAL MONTHLY COST
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The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the BrightMLS. Real estate listings held by brokerage firms other than Douglas Elliman of VA are marked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website.
All information deemed reliable but not guaranteed. Last date updated: 11/19/2025.
Source: Bright Multiple Listing Service, Inc.
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