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$5,200,000

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 5 Full Baths
  • 1 Partial Bath
  • 2,666 Sq. Ft.

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Open House: 12:00 PM - 2:00 PM

Saturday 1/17 12:00 PM - 2:00 PM

2 Chicago Street,Dewey Beach, DE 19971

2 Chicago StreetDewey BeachDE19971

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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.

Full Property Details for 2 Chicago St

General

  • Price: $5,200,000
  • Taxes: $6,705 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: DESU2077352
  • Updated: 12/17/2025
  • Added to Site: 112 day(s) ago

Interior

  • Interior Features: Ceiling Fan(s), Window Treatments, Combination Kitchen/Dining, Primary Bedroom - Ocean Front, Upgraded Countertops, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Exhaust Fan, Range Hood, Oven/Range - Electric, Dishwasher, Disposal, Dryer, Microwave, Washer, Refrigerator, Icemaker
  • Flooring: Ceramic Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 5
  • Half Bathrooms: 1
  • Upper 2 - Full Baths: 3
  • Upper Floor Baths: 4
  • Upper - Full Baths: 3
  • Upper - 1/2 Baths: 1
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 6
  • Bedrooms Upper: 4
  • Bedrooms-Up2: 4
  • Bedrooms Main & Up: 2

Other Rooms

  • Laundry: Lower Floor

Additional Information

  • Security/Safety: Smoke Detector

Exterior

  • Exterior Features: Gutter System, Outside Shower, Roof Deck
  • Porch/Patio/Deck: Deck(s), Porch(es), Balcony, Roof

Parking

  • Total Spaces: 3
  • Parking Features: Asphalt Driveway, Crushed Stone
  • Parking Type: Off Street

Location

  • Area: Lewes Rehoboth Hundred (31009)
  • County: SUSSEX
  • Subdivision: REHOBOTH BY THE SEA
  • Driving Directions: King Charles Avenue to east on Chicago Street. Oceanfront - corner, south side of street.
  • Direction Faces: North
  • Location Details: Oceanfront
  • City Limits: Yes

School Information

  • School District: Cape Henlopen

Community

  • Pets Allowed: Yes
  • Pets: No Pet Restrictions

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Zoned
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Dist. to Water: 0 Blocks
  • Utility Description: Cable TV, Sewer Available, Water Available

Structural Information

  • Architectural Style: Coastal, Contemporary
  • Structure Type: Detached
  • Construction: Frame
  • Foundation: Slab
  • Roof: Metal
  • Walls/Ceilings: Dry Wall
  • Windows: Bay/Bow, Double Hung
  • Entry Floor Number: 1
  • Stories Description: Main, Upper 1, Upper 2
  • Square Feet: 2,666
  • Sq. Ft. Source: Estimated
  • Living Area: 2,666 Sq. Ft.
  • Finished Above Grnd: 2,666 Sq. Ft.
  • Year Built: 1988
  • Year Built Source: Assessor
  • Property Condition: Very Good

Additional Structures

  • Other Structures: None

Lot Features

  • Property View: Ocean, Panoramic
  • Lot Size (Acres): 0.11
  • Lot Size (Sq. Ft.): 5,000
  • Lot Size Source: Estimated
  • Lot Dimensions: 50 x 100
  • Zoning: TN
  • Lot Description: Corner, Premium

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Public Beach
  • Water Front Type: Ocean
  • Water Front Name: Atlantic Ocean

Green Features

  • Energy Generation: PV Solar Array(s) Owned

Financial Considerations

  • Price Per Sq. Ft.: $1,950.49
  • Assessment Year: 2024
  • City/TownTax: $257
  • City/TownTax Freq: Annually
  • County Tax: $6,448
  • County Tax Freq: Annually
  • Tax Amount: $6,705
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 746

Disclosures and Reports

  • Ownership: Fee Simple
  • Exclusions: Artwork, some furniture, and staging items
  • Inclusions: Some furnishings

Listed by Jack Lingo - Rehoboth, SHAUN TULL and Jack Lingo - Rehoboth, BRYCE LINGO

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Listing agents

— 2 Chicago St —

  • SHAUN TULL

    Jack Lingo - Rehoboth

  • BRYCE LINGO

    Jack Lingo - Rehoboth

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2 Chicago St

School District:Cape Henlopen School District
NameGradesDistance
Rehoboth Elementary School
500 Stockley Street, Rehoboth Beach, DE 19971
PK-61 mi
Mariner Middle School
16391 Harbeson Road, Milton, DE 19968
5-813.6 mi
Cape Henlopen High School
1250 Kings Highway, Lewes, DE 19958
8-125.7 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2 Chicago St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/10/2025
Price Reduced
$5,200,000
-3.7%
MLS
9/26/2025
Listed
$5,400,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2 Chicago St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,448
85%
$64,300
—
2023
$3,488
—
$64,300
—
2023
$3,485
3%
$64,300
—
2022
$3,375
1%
$64,300
—
2021
$3,346
—
$64,300
—
2020
$3,336
1%
$64,300
—
2019
$3,319
18%
$64,300
—
2018
$2,824
4%
$64,300
—
2017
$2,704
5%
$64,300
—
2016
$2,568
4%
$64,300
—
2015
$2,475
1%
$64,300
—
2014
$2,457
3%
$64,300
—
2013
$2,388
—
$64,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Jack Lingo - Rehoboth, SHAUN TULL and Jack Lingo - Rehoboth, BRYCE LINGO

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2 Chicago Street, Dewey Beach, DE 19971 (MLS# DESU2077352) is a Single Family property with 6 bedrooms, 5 full bathrooms and 1 partial bathroom. 2 Chicago Street is currently listed for $5,200,000 and was received on September 26, 2025. Want to learn more about 2 Chicago Street? Do you have questions about finding other Single Family real estate for sale in Dewey Beach? You can browse all Dewey Beach real estate or contact a Coldwell Banker agent to request more information.

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