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.
Sold for $4,700,000
$4,700,000
2 Chicago St, Dewey Beach, DE 19971
6beds
2,666sqft
Single Family Residence
Built in 1988
5,000 Square Feet Lot
$4,698,800 Zestimate®
$1,763/sqft
$3,506 Estimated rent
Home value
$4,698,800
$4.46M - $4.93M
$3,506/mo
Zestimate® history
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List your homeWhat's special
Wide sandy beachWide beachesPrivate dune crossoverOceanfront opportunityExpansive oceanfront deckRecently updated kitchenSweeping panoramic views
Zillow last checked:
Listing updated:
Listed by:
SHAUN TULL 302-226-6417,
Jack Lingo - Rehoboth,
Listing Team: Bryce Lingo & Shaun Tull Team, Co-Listing Team: Bryce Lingo & Shaun Tull Team,Co-Listing Agent: Bryce Lingo 302-226-6417,
Jack Lingo - Rehoboth
Bought with:
Brian Barrows, RA-0020621
Monument Sotheby's International Realty
JENN BARROWS, RS-0015007
Monument Sotheby's International Realty
Source: Bright MLS,MLS#: DESU2077352
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 2
Basement
- Area: 0
Heating
- Heat Pump, Electric
Cooling
- Central Air, Zoned, Electric
Appliances
- Included: Exhaust Fan, Range Hood, Oven/Range - Electric, Dishwasher, Disposal, Dryer, Microwave, Washer, Refrigerator, Ice Maker, Electric Water Heater
- Laundry: Lower Level
Features
- Ceiling Fan(s), Combination Kitchen/Dining, Primary Bedroom - Ocean Front, Upgraded Countertops, Dry Wall
- Flooring: Ceramic Tile, Wood
- Windows: Bay/Bow, Double Hung, Window Treatments
- Has basement: No
- Number of fireplaces: 1
Interior area
- Total structure area: 2,666
- Total interior livable area: 2,666 sqft
- Finished area above ground: 2,666
- Finished area below ground: 0
Property
Parking
- Total spaces: 3
- Parking features: Asphalt, Crushed Stone, Off Street
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Patio & porch: Deck, Porch, Roof, Roof Deck
- Exterior features: Rain Gutters, Outdoor Shower, Balcony
- Pool features: None
- Has view: Yes
- View description: Ocean, Panoramic
- Has water view: Yes
- Water view: Ocean
- Waterfront features: Sandy Beach, Oceanfront, Beach Access, Ocean
- Body of water: Atlantic Ocean
- Frontage length: Water Frontage Ft: 50
Lot
- Size: 5,000 sqft
- Dimensions: 50 x 100
- Features: Corner Lot, Premium
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 33420.14156.00
- Zoning: TN
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Coastal,Contemporary
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Slab
- Roof: Metal
Condition
- Very Good
- New construction: No
- Year built: 1988
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Connected, Sewer Available, Water Available, Cable
Green energy
- Energy generation: PV Solar Array(s) Owned
Community & neighborhood
Security
- Security features: Smoke Detector(s)
Location
- Region: Dewey Beach
- Subdivision: Rehoboth By The Sea
Other
Other facts
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 5/1/2026 | Sold | $4,700,000-2%$1,763/sqft |
Source:  Bright MLS #DESU2077352 Report a problem | ||
| 3/11/2026 | Contingent | $4,795,000$1,799/sqft |
Source: Bright MLS #DESU2077352 Report a problem | ||
| 2/27/2026 | Price change | $4,795,000-4%$1,799/sqft |
Source: Bright MLS #DESU2077352 Report a problem | ||
| 2/14/2026 | Price change | $4,995,000-3.9%$1,874/sqft |
Source: Bright MLS #DESU2077352 Report a problem | ||
| 11/10/2025 | Price change | $5,200,000-3.7%$1,950/sqft |
Source: Bright MLS #DESU2077352 Report a problem | ||
| 9/26/2025 | Listed for sale | $5,400,000+92.9%$2,026/sqft |
Source: Bright MLS #DESU2077352 Report a problem | ||
| 2/15/2013 | Sold | $2,800,000$1,050/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,448 +84.9% | $1,451,150 +2156.8% |
| 2024 | $3,488 +0.1% | $64,300 |
| 2023 | $3,485 +3.3% | $64,300 |
| 2022 | $3,375 +0.8% | $64,300 |
| 2021 | $3,347 +0.3% | $64,300 |
| 2020 | $3,336 | $64,300 |
| 2019 | $3,336 +0.5% | $64,300 |
| 2018 | $3,319 +17.5% | $64,300 |
| 2017 | $2,824 +9.9% | $64,300 |
| 2016 | $2,568 +3.8% | $64,300 |
| 2015 | $2,475 +0.7% | $64,300 |
| 2014 | $2,457 +2.9% | $64,300 |
| 2013 | $2,388 -6.1% | $64,300 |
| 2012 | $2,543 +10.9% | $64,300 |
| 2011 | $2,293 | $64,300 |
| 2010 | $2,293 -2.7% | $64,300 |
| 2009 | $2,357 | $64,300 |
| 2008 | -- | -- |
| 2007 | -- | -- |
| 2006 | -- | -- |
| 2005 | -- | -- |
| 2004 | -- | -- |
| 2003 | -- | -- |
| 2002 | -- | -- |
| 2001 | -- | -- |
Find assessor info on the county website
Neighborhood: 19971
Nearby schools
GreatSchools rating
- 8/10Rehoboth Elementary SchoolGrades: K-5Distance: 1.1 mi
- 7/10Beacon Middle SchoolGrades: 6-8Distance: 4.2 mi
- 8/10Cape Henlopen High SchoolGrades: 9-12Distance: 5.7 mi
Schools provided by the listing agent
- District: Cape Henlopen
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Delaware
- Sussex County
- Dewey Beach
- 19971
- 2 Chicago St
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