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2 Chicago St
For Sale $4,995,000 ($1,873.59 per Sq Ft)
$4,995,000 ($1,873.59 per Sq Ft)
- 6 Bedrooms
- 6 Bathrooms
- 2,666 Sq Ft
- 5,000 Sq Ft
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.
Amenities
Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt
Property Details
| List Price | $4,995,000 |
| Property Type | Single Family Homes |
| Usable Sqft | 2,666 |
| Number of Stories | 0 stories |
| Parking Spots | 0 spots |
| Year Built | 1988 |
| Last Sold | Unknown |
| Sold Price | Unknown |
| APN # | 33420.14156.00 |
| MLS # | DESU2077352 |
| Property ID | 294320101 |
| Lot Sqft | 5,000 |
| Zoning | TN |
| Days on Market | 146 |
| Original List Price | Unknown |
| Applicances | Exhaust Fan,Range Hood,Oven/Range - Electric,Dishwasher,Disposal,Dryer,Microwave,Washer,Refrigerator,Icemaker% |
| Date Updated | February 14, 2026 |
| Date Created | September 25, 2025 |
| Unit # | Beds | Baths | Current Rent | Proforma Rent |
| Unit #1 | $0 | $0 |
Listing Provided By
SHAUN TULL an agent of Jack Lingo - Rehoboth. Lic #RS-0016284
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Data last updated: February 18, 2026.
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Robert Crawford
REAL ESTATE AGENT