2 Chicago Street Dewey Beach, DE $ 5,200,000
2 Chicago Street
$ 5,200,000
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2 Chicago Street

Dewey Beach, DE, 19971
$ 5,200,000
Bedrooms6 Baths5.1 Sq 2,666

Monthly Estimate*

$ 32,441

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Single Family Home for sale in Dewey Beach, DE

for $5,200,000 with 6 bedrooms and 5 full baths, 1 half bath. This 2,666 square foot home was built in 1988 on a lot size of 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 areasall 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, youll 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 birds-eye view of the coastlinean unforgettable setting for stargazing or enjoying fireworks on July 4th. Rehoboth by the Sea is one of the Delaware coasts 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 communitymaking this a truly rare opportunity to own a piece of coastal paradise.

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Single Family Active

Price

$ 5,200,000

Bedrooms

6

Full Bath

5

Half Bath

1

Property Type

Single Family

Taxes

$ 6,705

Style

Coastal,Contemporary

Lot Size

0.11

Year Built

1988

Town/City

Dewey Beach

County/Region

Sussex

MLS | Web ID

DESU2077352

Features
General
Living Area 2666
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Central A/C Zoned
Utilities Cable TV Sewer Available Water Available
Possession Settlement
Roof Metal
Appliances Exhaust Fan Range Hood Oven/Range - Electric Dishwasher Disposal Dryer Microwave Washer Refrigerator Icemaker
Zoning TN
Patio/Porch Features Deck(s) Porch(es) Balcony Roof
Architectural Style Coastal Contemporary
Security Features Smoke Detector
Construction Materials Frame
School District CAPE HENLOPEN
Exclusions Artwork some furniture and staging items
Year Built 1988
Electric 200+ Amp Service
View Ocean Panoramic
Levels 3
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Waterfront Features Sandy Beach
Building Name NONE AVAILABLE
Accessibility None
County SUSSEX
New Construction N
Property Type Residential
HOA N
Subdivision Name REHOBOTH BY THE SEA
Facing Direction North
Garage Y/N N
Water Access Y/N Y
Green Energy Generation PV Solar Array(s) Owned
Other Structures Above Grade Below Grade
Full Baths 5
Status ACTIVE
Directions King Charles Avenue to east on Chicago Street. Oceanfront - corner south side of street.
City DEWEY BEACH
Body of Water Atlantic Ocean
Disclosures Prop Disclosure
Senior Community Y/N N
MLS Area Lewes Rehoboth Hundred (31009)
Lot Size Units Square Feet
Lot Size Square Feet 5000.00
Tax Annual Amount 6705.2
Property Condition Very Good
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 2
Bathrooms Count Main Level 2.00
Price Per Sq Ft Total AG 1950.49
Acceptable Financing Cash Conventional
Additional Parcels Y/N N
Lease Considered Y/N N
Vacation Rental Y/N N
Virtual Tour https://www.dropbox.com/scl/fi/ccb02ii1w23mbpgn8mzfe/2_chicago_st_dewey_beach-1080p.mp4?rlkey=58nk46dooidffapkinoi5yp2l&dl=0
Location Type Oceanfront
Sussex DE Quadrants East of Rt 1
Standard Status Active
Year Built Source Assessor
Legal Subdivision Rehoboth By The Sea
Federal Flood Zone VE
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Interior
Interior Amenities Ceiling Fan(s) Window Treatments Combination Kitchen/Dining Primary Bedroom - Ocean Front Upgraded Countertops Wood Floors
Heating Fuel Electric
Flooring Ceramic Tile Wood
Total Fireplaces 1
Hot Water Electric
Basement (Y/N) N
Heating Y/N Y
Window Features Bay/Bow Double Hung
Fireplace Y/N Y
Above Grade Finished Area 2666
Half Baths 1
Central Air Y/N Y
Total Bedrooms 6
Below Grade Finished Area 0
Entry Level 1
Main Level Bedrooms 2
Below Grade Finished Area Unit Type Square Feet
Laundry Type Lower Floor
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Estimated
Above Grade Finished Area Unit Type Square Feet
Total Baths 6
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Exterior
Exterior Amenities Gutter System Outside Shower Roof Deck
Pool No Pool
Parking Features Asphalt Driveway Crushed Stone
Lot Features Corner Premium
Water Source Public
Inclusions Some furnishings
Type of Parking Off Street
Foundation Details Slab
Water View Y/N Y
Lot Dimensions 50 x 100
Lot Size Acres 0.11
Water Body Type Ocean
Lot Size Source Estimated
Waterfront Y/N Y
Water Access Features Public Beach
Road Responsibility City/County
Number of Docks 0
Navigable Water Y/N Y
Water Oriented Y/N Y
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Internal Only
Street Number 1 2
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* Excluded Features
List By
Jack Lingo - Rehoboth

Broker

shaun@rbre.com

Email

Affordability Calculator

$33,000
Per Month
98%
2%
0%
Monthly Principal & Interest
$32,441
Monthly Property Taxes
$559
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
2314408 Elementary School
2314409 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
11/10/2025$5,200,000 -3.70% Price Down
9/25/2025$5,400,000 Listed Price

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2 Chicago Street, Dewey Beach, DE, 19971 is a Single Family Home for sale at $5,200,000 with 2,666 sqft and a lot size of 0.11. 2 Chicago Street has 6 bedrooms, 5.1 baths, and was built in 1988. The property's zip code is 19971 which is in Dewey Beach, DE