105 CHICAGO STREET, DEWEY BEACH, DE 19971

  • Active

 $4,200,000

  • 7 BedroomBedrooms
  • 7 BathroomBathrooms
  • 4,284 Sq.Ft.
  • Single Family
  • Active
  • MLS# DESU2116162
  • Sold On
  • Rental
0 More Schedule
Source MLS Verified

PROPERTY DESCRIPTION

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 showerperfect 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.

Property Details

General

  • Subdivision: REHOBOTH BY THE SEA
  • Area: Lewes Rehoboth Hundred (31009)
  • County: SUSSEX-DE
  • Style: Coastal
  • Acreage: 0.15
  • Beds: 7
  • Full Bathrooms: 7
  • Ownership: Fee Simple
  • Year Built: 1974
  • Sq. Ft.: 4,284
  • Lot Size: 0.150000
  • Garage/Parking Spaces: 2.00
  • Garage Description: Garage - Side Entry, Garage Door Opener, Inside Access, Oversized
  • Lot Dimensions: 66.00 x 100.00

Interior Features

  • Interior Features: Attic, 2nd Kitchen, Air Filter System, Bathroom - Stall Shower, Bathroom - Tub Shower, Breakfast Area, Butlers Pantry, Carpet, Ceiling Fan(s), Combination Kitchen/Dining, Dining Area, Elevator, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Traditional, Intercom, Kitchen - Country, Kitchen - Galley, Kitchen - Gourmet, Pantry, Primary Bath(s), Recessed Lighting, Sound System, Upgraded Countertops, Walk-in Closet(s), Wet/Dry Bar, Window Treatments, Wine Storage, Wood Floors

Schools

  • High: CAPE HENLOPEN

Financial Considerations

  • Tax Amount: $3,769
  • Tax Year: 2025

Activity

  • Days On Market: 107
  • List Date: 07/15/2026
 

This calculator is provided by Burrow Services, Inc. for informational purposes. You should not make any decisions based simply on the information provided. Values indicated are estimates and may not be accurate and are only to be used as a guide. This calculator should not be relied upon in any way as the sole source of information. Please consult your financial, tax, or legal advisers for an accurate assessment of your mortgage payments and any advice relating to your personal circumstances.

Request Info / Schedule Showing

Realty ONE Group, Inc is powered by Burrow Services, Inc.