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105 Chicago Street, Dewey Beach, DE 19971

$4,800,000
  • 105 Chicago Street, Dewey Beach, DE 19971 Main Photo

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New to the Market ACTIVE
BEDS7 BATHS7 full SQUARE FEET7,136 MLS#DESU2116162
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONREHOBOTH BY THE SEA SCHOOLCAPE HENLOPEN

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 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.

105 Chicago Street | MLS# DESU2116162

This single family home located at 105 Chicago Street, Dewey Beach, DE 19971 is currently listed for sale with an asking price of $4,800,000. This property was built in 1974 and has 7 bedrooms and 7 full baths with 7136 sq. ft. Chicago Street is located in the REHOBOTH BY THE SEA subdivision within the CAPE HENLOPEN school district. Search REHOBOTH BY THE SEA real estate on cmorton.maverickrealtyusa.com today.

Property Features

Property Type: Residential - Single Family
Basement: Partial
Basement: Yes
Cooling: Central A/C
Fireplaces: 3
Fuel Type: Electric, Geo-thermal, Propane - Leased
Garage: 2
Heating: Heat Pump - Gas BackUp, Heat Pump(s), Other
Home Style: Coastal
Lot Size: 0.15 Acres
Roof Type: Architectural Shingle, Flat, Pitched
Stories: 4.0
Taxes: $5,522
Year Built: 1974

Feature Descriptions

Accessibility: 36"+ wide Halls, >84" Garage Door
Additional Structures: Above Grade, Below Grade
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
Building Name: NONE AVAILABLE
Days on Site: 1
Electric: 200+ Amp Service
Exterior: Chimney Cap(s), Extensive Hardscape, Exterior Lighting, Flood Lights, Gutter System, Lawn Sprinkler, Outside Shower, Roof Deck, Street Lights, Underground Lawn Sprinkler
Exterior: Masonry, Asphalt, Batts Insulation, Blown-In Insulati
Fencing: Panel, Rear
Fireplace: Fireplace - Glass Doors, Gas/Propane
Flooring: Carpet, Ceramic Tile, Hardwood, Laminate Plank
Interior: 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 Dimensions: 0.15 Acre(S)
Parking Notes: 8 Total Parking Spaces
Pet Restrictions: No Pet Restrictions
Sewer: Public Sewer
Special View Info: Ocean
SQFT Above Finished: 6274
SQFT Below Finished: 862
SQFT Total Finished: 7136
Structure Type: Detached
Total Garage/Parking Spaces: 8
Utilities: Cable TV, Phone, Propane, Sewer Available, Water Available
Water: Public
Windows: Double Hung, Double Pane, Energy Efficient, Insulated, Screens, Sliding, Vinyl Clad

Local Schools

High School: CAPE HENLOPEN
School District: CAPE HENLOPEN

Listed By / Shown By

Listed By

Agency Name: Mann & Sons, Inc.
Agency Phone: 3022279477

Shown By

Agent Name: Chad Morton
Agent Phone: (302) 373-5929
Agency Title: Maverick Realty, LLC

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Estimated Payment

$ 12,542.89 per month $10,682.72 Principal & Interest $460.17 Property Tax $1,400.00 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 07/17/2026. The listing information on this page last changed on 07/17/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 07/17/2026 12:00:24 AM EST) or Bright MLS (last updated Thu 07/16/2026 11:50:36 PM EST). Real estate listings held by brokerage firms other than Maverick Realty, LLC may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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