Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Listing photo for 2 Chicago St, Dewey Beach, DE
Previous View the Previous slide Next View the next slide

2 Chicago St,

Dewey Beach, DE $5,200,000

$5,200,000

Bed: 6
Bath: 5½
Sqft: 2,666
Acre: 0.11

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.

Facts & Features
MLS® # DESU2077352
Price $5,200,000
Bedrooms 6
Bathrooms 5.50
Full Baths 5
Half Baths 1
Square Footage 2,666
Acres 0.11
Year Built 1988
Type Single Family
Sub-Type Detached
Style Coastal, Contemporary
Status Active
Tax Year 2025
Annual Tax Amount $6,705
Community Information
Address 2 Chicago St
Area Lewes Rehoboth Hundred
Subdivision REHOBOTH BY THE SEA
City Dewey Beach
County SUSSEX-DE
State DE
Zip Code 19971
Within City Limits Yes
Sussex Delaware Quadrant East of Rt 1
Amenities
Amenities Ceiling Fan(s), Window Treatments, Primary Bedroom - Ocean Front, Upgraded Countertops, Wood Floors
Utilities Cable TV, Sewer Available, Water Available
Parking Asphalt Driveway, Crushed Stone
View Ocean, Panoramic
Is Waterfront Yes
Waterfront 10000001432
Interior
Appliances Exhaust Fan, Range Hood, Oven/Range - Electric, Dishwasher, Disposal, Dryer, Microwave, Washer, Refrigerator, Icemaker
Heating Heat Pump(s)
Cooling Central A/C, Zoned
Fireplace Yes
# of Fireplaces 1
Stories 3
Has Basement No
Exterior
Exterior Frame
Exterior Features Gutter System,Outside Shower,Roof Deck,Deck(s),Porch(es),Balcony,Roof
Lot Description Corner, Premium
Windows Bay/Bow, Double Hung
Roof Metal
Construction Frame
Foundation Slab
School Information
District CAPE HENLOPEN
Additional Information
Date Listed September 26th, 2025
Days on Market 110
Zoning TN
Foreclosure No
Short Sale No
RE / Bank Owned No
Listing Details
Office Jack Lingo - Rehoboth
Contact Info (302) 227-3883
Photo of Lauren Griffith

Lauren Griffith

Office: (302) 541-5262