105 CHICAGO STREET, DEWEY BEACH, DE 19971

$4,800,000

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.… Read More 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. Read Less

Courtesy of Mann & Sons, Inc.

Listing Snapshot

Days Online

Last Updated

Jul 17, 2026

Property Type

Single Family Residential

Beds

Full Baths

Square Ft.

7,136

Lot Size

0.15 Acres

Year Built

1974

MLS Number

DESU2116162

Additional Details

Property Access

Road Responsibility: Public, Road Surface: Black Top

Appliances & Equipment

Built-In Microwave, Built-In Range, Cooktop, Dishwasher, Disposal, Dryer - Electric, Dryer - Front Loading, Energy Efficient Appliances, Icemaker, Intercom, Microwave, Oven - Double, Oven - Self Cleaning, Oven - Single, Oven/Range - Electric, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Stove, Washer - Front Loading, Washer, Washer/Dryer Stacked, Water Heater, Water Heater - Tankless

Basement

Partial

Building

Built in 1974, Living area: 7136, Building faces South, Levels: 4, Construction Materials: Masonry, Asphalt, Batts Insulation, Blown-In Insulation, Concrete, CPVC/PVC, Frame, Shake Siding, Stick Built, Tile, Vinyl Siding

Cooling

Central A/C

Doors

Six Panel, Insulated

Accessibility Features

36"+ wide Halls, >84" Garage Door

Exterior Features

Patio/Porch Features: Balconies- Multiple, Porch(es), Roof, Screened, Chimney Cap(s), Extensive Hardscape, Exterior Lighting, Flood Lights, Gutter System, Lawn Sprinkler, Outside Shower, Roof Deck, Street Lights, Underground Lawn Sprinkler

Fence

Panel, Rear

Fireplaces

3 fireplaces, Fireplace - Glass Doors, Gas/Propane

Floors

Carpet, Ceramic Tile, Hardwood, Laminate Plank

Foundation

Block

Garage

2 spaces

Heating

Heat Pump - Gas BackUp, Heat Pump(s)

Interior Features

Attic, 2nd Kitchen, Air Filter System, Bathroom - Jetted Tub, 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

Lot

0.15 acres, Dimensions: 66.00 x 100.00

Pets Policy

Allowed: No Pet Restrictions

Property

Excellent, Other structures: Above Grade, Below Grade, Ocean

Roof

Architectural Shingle, Flat, Pitched

Security Features

Security System, Smoke Detector

Sewer

Public Sewer

Taxes

Additional parcels description:, Annual Amount: $5,522, Year: 2025, Zoning: TN

Utilities

Cable TV, Phone, Propane, Sewer Available, Water Available, Water Source: Public, 200+ Amp Service

Windows

Double Hung, Double Pane, Energy Efficient, Insulated, Screens, Sliding, Vinyl Clad

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