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PRICE $4,400,000 dsIDX morgage calculator
BEDS 7
BATHS 7
HOME SIZE 7,136 sqft
LOT SIZE 6,534 sqft

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.

DAYS ON MARKET 11 LAST UPDATED 7/27/2026
TRACT REHOBOTH BY THE SEA YEAR BUILT 1974
COMMUNITY Lewes Rehoboth Hundred (31009) GARAGE SPACES 2.0
COUNTY SUSSEX STATUS Active
PROPERTY TYPE(S) Single Family

SCHOOLS
School District CAPE HENLOPEN
High School CAPE HENLOPEN

PRICE HISTORY
Prior to Jul 27, '26 $4,800,000
Jul 27, '26 - Today $4,400,000


ADDITIONAL DETAILS
AIR Ceiling Fan(s), Central Air, Electric
AIR CONDITIONING Yes
APPLIANCES Built-In Range, Cooktop, Dishwasher, Disposal, Double Oven, Electric Oven, Electric Range, Electric Water Heater, ENERGY STAR Qualified Appliances, Gas Oven, Gas Range, Gas Water Heater, Ice Maker, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Tankless Water Heater, Washer, Washer/Dryer Stacked, Water Heater
AREA Lewes Rehoboth Hundred (31009)
BASEMENT Partial, Yes
CONSTRUCTION Asphalt, Batts Insulation, Blown-In Insulation, Concrete, Frame, Shake Siding, Vinyl Siding
EXTERIOR Balcony, Lighting, Rain Gutters
FIREPLACE Yes
GARAGE Yes
HEAT Electric, Geothermal, Heat Pump, Other, Propane
INTERIOR Bar, Ceiling Fan(s), Elevator, Pantry, Recessed Lighting, Sound System, Walk-in Closet(s)
LOT 6534 sq ft
LOT DIMENSIONS 66.00 x 100.00
PARKING Oversized, Garage Door Opener, Off Street, Garage, Driveway, Other, Inside Entrance, Attached
POOL DESCRIPTION None
SEWER Public Sewer
STORIES 3+
STYLE Coastal
SUBDIVISION REHOBOTH BY THE SEA
TAXES 5522
UTILITIES Cable Available, Propane, Sewer Available, Water Available
VIEW Yes
VIEW DESCRIPTION Water, Ocean
WATER Public
MORTGAGE CALCULATOR
   

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Listing provided by Mann & Sons, Inc.

Based on information from Sussex County Association of REALTORS®, Inc., which neither guarantees nor is in any way responsible for its accuracy. All data is provided 'AS IS' and with all faults. Data maintained by Sussex County Association of REALTORS®, Inc. may not reflect all real estate activity in the market.
Copyright 2026 Sussex County Association of REALTORS®, Inc.

This IDX solution is (c) Diverse Solutions 2026.