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16 CHICAGO ST, DEWEY BEACH, DE 19971

5 Beds

6 Baths

4,500SqFt

Active

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 Details
Price $5,250,000
Bedrooms 5
Full Baths 4
Half Baths 2
Total Baths 6
Property Style Coastal
Lot Size 50 x 100
Lot Size Area Units Square Feet
Acres 0.11
Property Type Residential
Sub type SingleFamilyResidence
MLS Sub type Detached
Stories 3
Features Pantry,Ceiling Fan(s),Elevator,Window Treatments
Exterior Features Lawn Sprinkler,Outside Shower
Year Built 2000
Fireplaces 2
Subdivision REHOBOTH BY THE SEA
View Ocean
Roof Architectural Shingle
Heating Forced Air,Heat Pump(s)
Foundation Pilings
Accessibility Elevator
Lot Description Landscaping
Parking Description Crushed Stone
Garage spaces 2
Geographic Data
Directions Ocean Block of Chicago Street in Rehoboth by the Sea in Dewey Beach
County SUSSEX
Latitude 38.69987
Longitude -75.07505
Market Area Lewes Rehoboth Hundred (31009)
Address Information
Address 16 CHICAGO ST, DEWEY BEACH, DE 19971
Postal Code 19971
City DEWEY BEACH
State DE
Country United States
Listing Information
Listing Office Monument Sotheby's International Realty
Listing Office Email justin.healy@msir.net
Listing Agent Kimberly Hamer
Special listing conditions Standard
Ownership Fee Simple
Terms Cash,Conventional
Virtual Tour URL https://players.brightcove.net/5782667248001/default_default/index.html?videoId=6380112464112
School Information
District CAPE HENLOPEN
MLS Information
Days on market 3
MLS Status Active
Listing Date Jul 24, 2026
Listing Last Modified Jul 26, 2026
Tax ID 334-20.14-161.00
Tax Annual Amount 5068
MLS Area Lewes Rehoboth Hundred (31009)
MLS # DESU2116884

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Last updated: 2026-07-26T19:00:25.8637Z. Listing information is provided by Bright MLS. Listings are generated from various brokers who participate in IDX. Information is deemed reliable but not guaranteed.