105 Chicago Street, Dewey Beach, DE
Experience exceptional coastal living in this stunning 7-bedroom, 7-bathroom luxury home, ideally located just steps from the beach in the heart of Dewey Beach. Designed for comfort, entertaining, and multi-generational living, this remarkable property offers expansive indoor and outdoor spaces with high-end finishes throughout.
The highlight of the home is the spacious rooftop deck, where you can entertain guests, soak up the sun, or simply unwind while enjoying beautiful panoramic beach views. Just minutes from both Dewey Beach and Rehoboth Beach, you'll have easy access to award-winning restaurants, boutique shopping, nightlife, and everything the Delaware beaches have to offer.
Inside, you'll find a thoughtfully designed floor plan featuring a gourmet kitchen with premium stainless steel appliances, a second kitchen for added convenience, a butler's pantry, breakfast area, wine storage, wet bar, and generous dining and living spaces. The home also offers an elevator, entry-level bedroom, family room off the kitchen, walk-in closets, upgraded countertops, wood flooring, recessed lighting, intercom, whole-home sound system, and luxurious primary suites with spa-inspired baths, including jetted tubs and oversized stall showers.
Three gas fireplaces with elegant glass doors create warm and inviting gathering spaces, while dual laundry areas on both the upper and lower levels provide everyday convenience.
Additional premium features include:
Energy-efficient appliances and tankless water heater
Air filtration system
Security system and smoke detectors
36-inch-plus wide hallways and an oversized 84-inch garage door for enhanced accessibility
Insulated six-panel doors and energy-efficient double-pane, vinyl-clad windows with screens
Ceiling fans, window treatments, and abundant storage throughout

The exterior is equally impressive, showcasing extensive hardscaping, professional landscaping with underground irrigation, exterior lighting, floodlights, gutter system, chimney caps, and an outdoor shower—perfect after a day at the beach. Multiple balconies, screened porches, and the expansive rooftop deck provide exceptional outdoor living spaces to enjoy coastal breezes and scenic views.
Property Highlights
7 Bedrooms
7 Bathrooms
Spacious rooftop deck with beautiful beach views
Gourmet kitchen plus second kitchen
Elevator
3 Gas fireplaces
Wine storage and wet bar
Multiple balconies and screened porch
Outdoor shower
Extensive hardscaping and irrigation system
No HOA pool to maintain
Prime location near Dewey Beach, Rehoboth Beach, restaurants, shopping, and local attractions
This extraordinary beach home combines luxury, functionality, and an unbeatable location, making it an exceptional primary residence, vacation retreat, or investment opportunity.