16 Chicago St, DEWEY BEACH, DE

$5,250,000

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5

Beds

5

Baths

4,500

Square feet

0.11

Acres

About 16 Chicago St

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.

Features of 16 Chicago St

MLS® # DESU2116884
Price $5,250,000
Bedrooms 5
Bathrooms 5.00
Full Baths 4
Half Baths 2
Square Footage 4,500
Acres 0.11
Year Built 2000
Type Single Family
Sub-Type Detached
Style Coastal
Status Active Under Contract

Community Information

Address 16 Chicago St
Area Lewes Rehoboth Hundred
Subdivision REHOBOTH BY THE SEA
City DEWEY BEACH
County SUSSEX-DE
State DE
Zip Code 19971

Amenities

Amenities Pantry, Ceiling Fan(s), Elevator, Window Treatments
Parking Crushed Stone
# of Garages 2
Garages Garage Door Opener
View Ocean
Is Waterfront No
New Construction No

Interior

Appliances Dishwasher, Disposal, Dryer - Electric, Microwave, Oven/Range - Gas, Range Hood, Refrigerator, Washer
Heating Forced Air, Heat Pump(s)
Cooling Central A/C, Zoned
Has Basement No
Fireplace Yes
# of Fireplaces 2
Fireplaces Gas/Propane
Stories 3

Exterior

Exterior Features Lawn Sprinkler,Outside Shower,Balcony,Deck(s)
Lot Description Landscaping
Roof Architectural Shingle
Construction Stick Built
Foundation Pilings

School Information

District CAPE HENLOPEN

Additional Information

Date Listed July 24th, 2026
Days on Market 15
Zoning RESIDENTIAL
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Map

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