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$5,250,000
$7,200Reward *
16 CHICAGO STREET, DEWEY BEACH, DE 19971Listing ID DESU2116884

16 CHICAGO STREET, DEWEY BEACH, DE 19971

Contingent
REHOBOTH BY THE SEA
Last updated: Aug 7, 2026
Property Type
Property Type
Residential
Property Sub Type
Property Sub Type
-
Bedrooms
Bedrooms
5
Bathrooms
Bathrooms
6
Square Feet
Square Feet
4,500
Acres
Acres
0.11
Days on Site
Days on Site
24
Cooling
Cooling
Central A/C, Zoned
Heating
Heating
Forced Air, Heat Pump(s)
Year Built
Year Built
2000
Garages
Garages
2
Parking
Parking
Crushed Stone

Coastal Luxury with Ocean Views & Breezes! Experience the perfect blend of luxury, comfort, and coastal charm in this stunning, professionally renovated beach retreat. Designed for effortless indoor-outdoor living, this exceptional home captures sweeping Atlantic Ocean views, refreshing sea breezes, and sophisticated designer finishes throughout. Ideally situated on a fee simple ocean block lot in the sought-after Rehoboth by the Sea community in Dewey Beach, this remarkable residence was completely reimagined in 2020 by renowned architect Tony Beto and custom home builder Dewson. The extensive renovation included a new roof, siding, HVAC systems, decks, and beautifully redesigned interior and exterior living spaces. The welcoming foyer opens to a spacious first level featuring four generously sized bedrooms, including three private ensuite bedrooms. This level also offers a large laundry room complete with a built-in dog washing station, a convenient powder room, elevator access, and two outdoor living areas designed for gathering, relaxing, and enjoying the coastal lifestyle. Upstairs, the open-concept living space is both elegant and inviting. The gourmet kitchen, complete with high-end appliances and an oversized walk-in pantry, flows seamlessly into the dining area and spacious great room. A cozy fireplace anchors the space, while sliding glass doors lead to a covered deck with a pergola and panoramic ocean views—creating the perfect setting for entertaining or simply unwinding by the sea. The luxurious owner's suite is a private sanctuary featuring its own deck, a double-sided fireplace, and a spa-inspired bath with a soaking tub, oversized tiled shower, dual vanities, and a private water closet. The ground level offers a spacious garage with coated floors, abundant storage, an outdoor shower, and a private fenced backyard—ideal for pets, outdoor enjoyment, or quiet relaxation after a day at the beach. Every detail of this home reflects exceptional craftsmanship and thoughtful design. Highlights include cathedral ceilings, hardwood flooring, custom millwork, shiplap accents, wainscoting, designer wallpaper, exquisite tilework, on-demand hot water, central vacuum, an elevator, and premium finishes throughout. Professionally furnished and offered move-in ready, this extraordinary coastal home is equally suited as a full-time residence, luxurious vacation retreat, or exceptional investment property with strong rental potential. Schedule your private showing or take the video tour to experience this extraordinary ocean-block retreat for yourself.

Property Information

Property Details

Location

Address
16 CHICAGO STREET
City
DEWEY BEACH
Zip Code
19971
Subdivision
REHOBOTH BY THE SEA
MLS Area
Lewes Rehoboth Hundred (31009)

Interior Features

Beds and Baths

Bedrooms
5
Main Level Bedrooms
4
Full Bathrooms
4
Half Bathrooms
2

Building

Building Information

Square Feet
4,500
Year Built
2000
Construction
Stick Built
Foundation
Pilings
Roof
Architectural Shingle
Builder Name
Dewson
Condition
Excellent

Property Taxes

Tax Annual Amount
$5,068
Monument Sotheby's International Realty, (302) 227-6767

Market Report for 19971

* The market data shown is based on available information from Multiple Listing Service (MLS) and/or public records. Data provided is for informational and educational purposes only and may not represent the full housing market. For more accurate information, consumers should consult a certified appraiser or licensed real estate agent.

*Average of $2,150 in rewards is calculated based on the purchase or sale of a home between $400,000 to $449,000. The median home price for all housing types is in the United States is $405,400 as of 2025 as reported by the National Association of Realtors® (NAR). The actual reward amount may vary depending on the purchase or sales price of the home. Please see the Lakeview Home Rewards program terms and conditions for more details. The National Association of Realtors® is a registered trademark of the National Association of Realtors®.

Source: Bright MLS
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