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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.
| DAYS ON MARKET | 32 | LAST UPDATED | 11/10/2025 |
|---|---|---|---|
| TRACT | REHOBOTH BY THE SEA | YEAR BUILT | 1988 |
| COMMUNITY | Lewes Rehoboth Hundred (31009) | COUNTY | SUSSEX |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| School District | CAPE HENLOPEN |
|---|
| PRICE HISTORY | |
| Prior to Nov 10, '25 | $5,400,000 |
|---|---|
| Nov 10, '25 - Today | $5,200,000 |
| ADDITIONAL DETAILS | |
| AIR | Ceiling Fan(s), Central Air, Electric, Zoned |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Disposal, Dryer, Electric Oven, Electric Range, Electric Water Heater, Exhaust Fan, Ice Maker, Microwave, Range Hood, Refrigerator, Washer |
| AREA | Lewes Rehoboth Hundred (31009) |
| CONSTRUCTION | Frame |
| EXTERIOR | Balcony, Rain Gutters |
| FIREPLACE | Yes |
| HEAT | Electric, Exhaust Fan, Heat Pump |
| INTERIOR | Ceiling Fan(s) |
| LOT | 4792 sq ft |
| LOT DESCRIPTION | Corner Lot, Waterfront |
| LOT DIMENSIONS | 50 x 100 |
| PARKING | Asphalt, Off Street, Gravel |
| POOL DESCRIPTION | None |
| SEWER | Public Sewer |
| STORIES | 3+ |
| STYLE | Coastal, Contemporary |
| SUBDIVISION | REHOBOTH BY THE SEA |
| TAXES | 6705.2 |
| UTILITIES | Cable Available, Sewer Available, Water Available |
| VIEW | Yes |
| VIEW DESCRIPTION | Water, Ocean, Panoramic |
| WATER | Public |
| WATER ACCESS | Atlantic Ocean |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | Ocean Front, Beach Access |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Jack Lingo - Rehoboth
Based on information from Sussex County Association of REALTORS®, Inc., which neither guarantees nor is in any way responsible for its accuracy. All data is provided 'AS IS' and with all faults. Data maintained by Sussex County Association of REALTORS®, Inc. may not reflect all real estate activity in the market.
Copyright 2025 Sussex County Association of REALTORS®, Inc.
This IDX solution is (c) Diverse Solutions 2025.
