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.
Sold for $4,700,000
Zillow last checked:
Listing updated:
Bought with:
Brian Barrows, RA-0020621
Monument Sotheby's International Realty
JENN BARROWS, RS-0015007
Monument Sotheby's International Realty
Source: Bright MLS,MLS#: DESU2077352
Price history
| Date | Event | Price |
|---|---|---|
| 5/1/2026 | Sold | $4,700,000-2%$1,763/sqft |
Source:  Bright MLS #DESU2077352 Report a problem | ||
| 3/11/2026 | Contingent | $4,795,000$1,799/sqft |
Source: Bright MLS #DESU2077352 Report a problem | ||
| 2/27/2026 | Price change | $4,795,000-4%$1,799/sqft |
Source: Bright MLS #DESU2077352 Report a problem | ||
| 2/14/2026 | Price change | $4,995,000-3.9%$1,874/sqft |
Source: Bright MLS #DESU2077352 Report a problem | ||
| 11/10/2025 | Price change | $5,200,000-3.7%$1,950/sqft |
Source: Bright MLS #DESU2077352 Report a problem | ||
| 9/26/2025 | Listed for sale | $5,400,000+92.9%$2,026/sqft |
Source: Bright MLS #DESU2077352 Report a problem | ||
| 2/15/2013 | Sold | $2,800,000$1,050/sqft |
Source: Public Record Report a problem | ||
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