2 Chicago St Dewey Beach, DE 19971
Estimated payment $27,723/month
Total Views
52,119
6
Beds
5.5
Baths
2,666
Sq Ft
$1,950
Price per Sq Ft
Highlights
- 50 Feet of Waterfront
- Ocean View
- Access to Tidal Water
- Rehoboth Elementary School Rated A
- Primary bedroom faces the ocean
- Sandy Beach
About This Home
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.
Listing Agent
(302) 226-6417 shaun@rbre.com Jack Lingo - Rehoboth License #RS-0016284 Listed on: 09/26/2025
Co-Listing Agent
(302) 226-6417 bryce@rbre.com Jack Lingo - Rehoboth License #RA-0001746
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $6,705
Year Built
- Built in 1988
Lot Details
- 5,000 Sq Ft Lot
- Lot Dimensions are 50 x 100
- 50 Feet of Waterfront
- Ocean Front
- Home fronts navigable water
- Sandy Beach
- Public Beach
- North Facing Home
- Premium Lot
- Corner Lot
- Property is in very good condition
- Property is zoned TN
Property Views
- Ocean
- Panoramic
Home Design
- Coastal Architecture
- Contemporary Architecture
- Entry on the 1st floor
- Slab Foundation
- Frame Construction
- Metal Roof
Interior Spaces
- 2,666 Sq Ft Home
- Property has 3 Levels
- Ceiling Fan
- 1 Fireplace
- Double Hung Windows
- Bay Window
- Combination Kitchen and Dining Room
- Fire and Smoke Detector
Kitchen
- Electric Oven or Range
- Range Hood
- Microwave
- Ice Maker
- Dishwasher
- Upgraded Countertops
- Disposal
Flooring
- Wood
- Ceramic Tile
Bedrooms and Bathrooms
- Primary bedroom faces the ocean
Laundry
- Laundry Room
- Laundry on lower level
- Dryer
- Washer
Parking
- 3 Parking Spaces
- Gravel Driveway
Outdoor Features
- Outdoor Shower
- Access to Tidal Water
- Water Access
- Property is near an ocean
- Balcony
- Rooftop Deck
- Rain Gutters
- Porch
Utilities
- Zoned Heating and Cooling
- Heat Pump System
- Vented Exhaust Fan
- 200+ Amp Service
- Electric Water Heater
- Municipal Trash
- Cable TV Available
Additional Features
- Solar owned by seller
- Flood Risk
Community Details
- No Home Owners Association
- Rehoboth By The Sea Subdivision
Listing and Financial Details
- Assessor Parcel Number 334-20.14-156.00
Map
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $6,448 | $64,300 | $25,000 | $39,300 |
| 2024 | $3,488 | $64,300 | $25,000 | $39,300 |
| 2023 | $3,485 | $64,300 | $25,000 | $39,300 |
| 2022 | $3,375 | $64,300 | $25,000 | $39,300 |
| 2021 | $3,347 | $64,300 | $25,000 | $39,300 |
| 2020 | $3,336 | $64,300 | $25,000 | $39,300 |
| 2019 | $3,319 | $64,300 | $25,000 | $39,300 |
| 2018 | $2,824 | $64,300 | $0 | $0 |
| 2017 | $2,704 | $64,300 | $0 | $0 |
| 2016 | $2,568 | $64,300 | $0 | $0 |
| 2015 | $2,475 | $64,300 | $0 | $0 |
| 2014 | $2,457 | $64,300 | $0 | $0 |
Source: Public Records
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 11/10/2025 11/10/25 | Price Changed | $5,200,000 | -3.7% | $1,950 / Sq Ft | |
| 09/26/2025 09/26/25 | For Sale | $5,400,000 | +92.9% | $2,026 / Sq Ft | |
| 02/15/2013 02/15/13 | Sold | $2,800,000 | 0.0% | -- | View Prior Sale |
| 02/15/2013 02/15/13 | Pending | -- | -- | -- | |
| 03/08/2012 03/08/12 | For Sale | $2,800,000 | -- | -- |
Source: Bright MLS
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | -- | None Listed On Document | |
| Deed | -- | None Listed On Document | |
| Deed | -- | None Listed On Document | |
| Deed | $2,800,000 | -- |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $250,000 | Purchase Money Mortgage | |
| Previous Owner | $417,000 | No Value Available |
Source: Public Records
About the Listing Agent
Shaun has worked for Jack Lingo Inc – Realtor since 2003 and has closed more than $2 billion in real estate sales in his career. Leveraging his extensive experience and real time insights into market dynamics and buyer sentiment, he advises on product design and the marketing programs for JLAM assets.
Shaun is an Associate Broker at Jack Lingo Inc – Realtor and manages a talented team of agents with a strong focus on the coastal Delaware resort markets. He is a native of Delaware and
Shaun's Other Listings
Source: Bright MLS
MLS Number: DESU2077352
APN: 334-20.14-156.00
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement.
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.
Copyright 2025 Bright MLS, Inc.
Nearby Homes
- 24 West St
- 21 Houston St Unit 7
- 23 Jersey St
- 1602 Bayard Ave
- 114 Chesapeake St
- 122 Houston St
- 38520 Pine Ln Unit 2
- 1904 Coastal Hwy Unit E
- 21095 Elizabeth Ave
- 307 Swedes St
- 38312 James A St
- 9 Read Ave Unit 12
- 1 Read Ave Unit 114
- 101 Dover Rd
- 0 Route 1 & Old Bay Rd Unit DESU183522
- 116D Read St Unit 116
- 37924 Even Tide Ln
- 37926 Even Tide Ln
- 46 Bay Reach
- 1406 Coastal Hwy Unit 3-D
- 360 Bay Reach
- 38172 Robinsons Dr Unit 9
- 20527 Washington St Unit Garrage Carriage House
- 20356 Blue Point Dr Unit 1204
- 29 Maryland Ave
- 31 6th St Unit B
- 37487 Burton Ct
- 1 Virginia Ave Unit 202
- 310 Blue Heron Dr Unit 2
- 29805 Striper Harbor Unit C3
- 37285 Martin St Unit 27
- 21440 Bald Eagle Rd Unit Carriage House
- 20327 Mallory Ct
- 37684 Ulster Dr Unit 16
- 20013 Newry Dr Unit 7
- 36519 Palm Dr Unit 4103
- 36507 Palm Dr Unit 2306
- 21235 Catalina Cir Unit A-38
- 30 Wanoma Cir
- 6 Gordons Pond Dr