About this home

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.

Facts and features

Schools

• Rehoboth Elementary School

  elementary · K-5 · 0.9 mi

  8

• Cape Henlopen High School

  high · 9-12 · 5.6 mi

  8

• Mariner Middle School

  middle · 6-8 · 13.5 mi

  6

• Beacon Middle School

  middle · 6-8 · 4.0 mi

  7

• Love Creek Elementary School

  elementary · K-5 · 4.2 mi

  10

• Shields (Richard A.) Elementary School

  elementary · K-5 · 6.0 mi

  9

Price history

• Aug 13, 2026 · Price Changed$4,200,000
• Jul 27, 2026 · Price Changed$4,400,000
• Jul 15, 2026 · Listed$4,800,000

Tax history

• 2026$3,366 tax · $843,150 assessed
• 2024$4,781 tax · $843,150 assessed
• 2023$4,777 tax · $100,700 assessed
• 2022$4,604 tax · $100,700 assessed
• 2021$4,660 tax · $100,700 assessed
• 2020$4,645 tax · $100,700 assessed
• 2019$4,630 tax · $100,700 assessed
• 2018$4,022 tax · $100,700 assessed

Home value

$4,158,000

• Collateral Analytics$4,158,000
• Cotality$4,107,200
• Quantarium$4,632,445

Where it is