- Overview
- Description
- Property Details
- Location
- Facts & Features
- Getting Around
- Nearby Homes
$4,795,000
Monthly Est:$23,866
6 Beds
- 6 Baths
5 full baths + 1 half bath
2,666sqft
2 Chicago St, Dewey Beach, DE 19971
$4,795,000
$23,866/moEst:
Get Pre-Approved
Single Family Residence
Built in 1988
$-- HOA
5,000 sqft lot
$1,799/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.
- Houzeo last checked: 1 hour ago
- Listing updated: March 9, 2026 at 5:54 pm
- Listing Provided by: SHAUN TULL (302) 226-6417 , BRYCE LINGO (302) 226-6417 | Jack Lingo - Rehoboth (302) 227-3883
- Source: Bright MLS-NJ | MLS#: DESU2077352

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1988
HOA Fees
-
Finished Area
2,666 sqft
Lot Size
5,000 sqft lot
Basement Area
- sqft
MLS Name
Bright MLS
MLS Number
DESU2077352
MLS Status
ACTIVE-BRIGHT
Days on Market
165

Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 6
Bathrooms: 6
Interior
Flooring
Ceramic Tile, Wood
Exterior Features
Gutter System, Outside Shower, Roof Deck
Window Features
Bay/bow, Double Hung
Interior Features
Ceiling Fan(s), Window Treatments, Combination Kitchen/dining, Primary Bedroom Ocean Front, Upgraded Countertops, Wood Floors
Heating
Heat Pump(s)
Cooling
Central A/c, Zoned
Appliances
Exhaust Fan, Range Hood, Oven/range Electric, Dishwasher, Disposal, Dryer, Microwave, Washer, Refrigerator, Icemaker
Sewer
Public Sewer
Construction
Year Built
Year Built: 1988
Home type
Single Family Residence
Construction Materials
Frame
Architectural Style
Coastal, Contemporary
Foundation Details
Slab
Property Condition
Very Good
Roof
Metal
Utilities & Energy
Electric
200+ Amp Service
Parking Features
Asphalt Driveway, Crushed Stone
Water Source
Public
Utilities
Cable Tv, Sewer Available, Water Available
Security Features
Smoke Detector
Other Features
Lot Features
Corner, Premium
Patio And Porch Features
Deck, Porch, Balcony, Roof
Subdivision Name
Rehoboth By The Sea
Price History
| Date | Event | Price |
|---|---|---|
02/27/2026 Source: | Price Decreased | $4,795,000 -4.00% $0/sqft |
09/26/2025 Source: | Listed for Sale | $4,995,000 -3.94% $0/sqft |
09/26/2025 Source: | Price Decreased | $5,200,000 -3.70% $0/sqft |
09/26/2025 Source: | Price Increased | $5,400,000 +92.86% $0/sqft |
02/15/2013 Source: | Sold | $2,800,000 $0/sqft |
Nearby Homes
Find Homes by Property Features in Dewey Beach, DE
Nearby New Homes For Sale
Based on information from Bright MLS through Nov 05, 2026, 12:45PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information
Advertising Broker: Joe Hawkins | Hawkins Real Estate Services














