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2 Chicago Street

DEWEY BEACH, DE 19971
  • $5,200,000
  • STATUS: Active
  • ON SITE: 116 Days
  • ID#: DESU2077352
$5,200,000
  • 6
    BEDS
  • 0.11
    ACRES
  • 5
    BATHS
  • 1
    1/2 BATHS
  • 2,666
    SQFT
  • $1,950
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1988
County:

School Ratings & Info

School District:

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.

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©2026 Bright MLS, All Rights Reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or The Rhonda Frick Team | Long & Foster Real Estate. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2026-01-18T23:50:45.583.
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2 Chicago Street DEWEY BEACH, DE 19971

  • Price: $5,200,000
  • Status: Active
  • On Site: 116 Days
  • ID#: DESU2077352
6
Beds
5
Baths
1
½ Baths
0.11
Acres
2,666
SQFT
$1,950
$/SQFT
1988
Built
Neighborhood:
Rehoboth By The Sea
County:
Sussex
Area:
Lewes Rehoboth Hundred (31009)
School District:
Cape Henlopen
Property 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.
Exterior Features

Architectural Style CoastalContemporary Construction Materials Frame Distance To Body Of Water 0 Docks 0 Exterior Features Gutter SystemOutside ShowerRoof Deck Garage YN No Location Type Oceanfront Lot Features CornerPremium Other Structures None Parking Features Asphalt DrivewayCrushed Stone Parking Types Off Street Patio And Porch Features Deck(s)Porch(es)BalconyRoof Pool No Pool Property Condition Very Good Road Responsibility City/County Roof Metal View OceanPanoramic Water Access Features Public Beach Water Access YN Yes Water Body Name Atlantic Ocean Water Body Type Ocean Water View YN Yes Waterfront Features Sandy Beach Waterfront YN Yes

Interior Features

Above Grade Fin SQFT 2666 Appliances Exhaust FanRange HoodOven/Range - ElectricDishwasherDisposalDryerMicrowaveWasherRefrigeratorIcemaker Basement YN No Below Grade Finished Area 0 Below Grade Unfinished Area 0 Cooling Central A/CZoned Exclusions Artworksome furnitureand staging items Fireplace YN Yes Fireplaces Total 1 Flooring Ceramic TileWood Heating Heat Pump(s) Heating YN Yes Inclusions Some furnishings Interior Features Ceiling Fan(s)Window TreatmentsCombination Kitchen/DiningPrimary Bedroom - Ocean FrontUpgraded CountertopsWood Floors Laundry Type Lower Floor Levels 3 Main Level Bedrooms 2 Pets Allowed No Pet Restrictions Security Features Smoke Detector Upper Level1 Bedrooms 0 Walls Ceilings Dry Wall

Property Features

Acceptable Financing CashConventional Accessibility Features None Association YN No Central Air YN Yes Condo YN No Cooling Fuel Electric Electric 200+ Amp Service Entry Level 1 Federal Flood Zone VE Federal Flood Zone YN Yes Foundation Details Slab Green Energy Generation PV Solar Array(s) Owned Heating Fuel Electric Hot Water Electric Lease Considered YN No Navigable Water YN Y New Construction YN No Original MLSNumber 803584417392 Ownership Interest Fee Simple Pets Allowed YN Yes Sale Type Standard Senior Community YN No Sewer Public Sewer Structure Design Type Detached Tax Annual Amount 6705.20 Utilities Cable TVSewer AvailableWater Available Vacation Rental YN No Water Source Public Window Features Bay/BowDouble Hung Zoning TN

Listing courtesy of Jack Lingo - Rehoboth: .


©2026 Bright MLS, All Rights Reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or The Rhonda Frick Team | Long & Foster Real Estate. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2026-01-18T23:50:45.583.
 
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33298 Coastal Hwy
Bethany Beach DE, 19930