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105 Chicago St, Dewey Beach, DE

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$4,400,000

7

Beds :

7

Baths :

7,136

Square feet :

0.15

Acres :

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.

Features of 105 Chicago St

MLS® # DESU2116162
Price $4,400,000
Bedrooms 7
Bathrooms 7.00
Full Baths 7
Square Footage 7,136
Acres 0.15
Year Built 1974
Type Residential
Sub-Type Detached
Style Coastal
Status Active

Community Information

Address 105 Chicago St
Area Lewes Rehoboth Hundred
Subdivision REHOBOTH BY THE SEA
City DEWEY BEACH
County SUSSEX-DE
State DE
Zip Code 19971
Within City Limits Yes
Sussex Delaware Quadrant East of Rt 1

Amenities

Amenities Attic, Air Filter System, Bathroom - Stall Shower, Bathroom - Tub Shower, Butlers Pantry, Carpet, Ceiling Fan(s), Elevator, Entry Level Bedroom, Intercom, Pantry, Primary Bath(s), Recessed Lighting, Sound System, Upgraded Countertops, Walk-in Closet(s), Wet/Dry Bar, Window Treatments, Wine Storage, Wood Floors
Utilities Cable TV, Phone, Propane, Sewer Available, Water Available
# of Garages 2
Garages Garage - Side Entry, Garage Door Opener, Inside Access, Oversized
View Ocean
Is Waterfront No

Interior

Interior Features Floor Plan - Traditional
Appliances 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
Heating Heat Pump - Gas BackUp, Heat Pump(s), Other
Cooling Central A/C
Fireplace Yes
# of Fireplaces 3
Fireplaces Fireplace - Glass Doors, Gas/Propane
Stories 4
Has Basement Yes
Basement Partial

Exterior

Exterior Concrete, Frame, Shake Siding, Vinyl Siding
Exterior Features Chimney Cap(s),Extensive Hardscape,Exterior Lighting,Flood Lights,Gutter System,Lawn Sprinkler,Outside Shower,Roof Deck,Street Lights,Underground Lawn Sprinkler,Balconies- Multiple,Porch(es),Roof,Screened,Panel,Rear
Windows Double Hung, Double Pane, Energy Efficient, Insulated, Screens, Sliding, Vinyl Clad
Roof Architectural Shingle, Flat, Pitched
Construction Masonry, Asphalt, Batts Insulation, Blown-In Insulation, Concrete, CPVC/PVC, Frame, Shake Siding, Stick Built, Tile, Vinyl Siding
Foundation Block

School Information

District CAPE HENLOPEN
High CAPE HENLOPEN

Additional Information

Date Listed July 16th, 2026
Days on Market 29
Zoning TN
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeMann & Sons, Inc.

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33298 Coastal Hwy, Unit 4 Bethany Beach, DE 19930

(302) 539-9040
(302) 541-5207 Leslie@LeslieKopp.com

Based on information from Sussex County Association of REALTORS®, Inc which neither guarantees nor is in any way responsible for it's accuracy. All data is provided "AS IS" and with all it's faults. Data maintained by Sussex County Association of REALTORS®, Inc. may not reflect all real estate activity in the market Bay Coast Realty is a Real Estate licensee in the State of Delaware. SCAOR DE License Number: SCAOR 08098.

Copyright 2026 Sussex County Association of REALTORS®, Inc.