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Street View
$4,200,000
Monthly Est:$20,905
8 Beds
- 7 Baths
7 full baths
7,136sqft
105 Chicago St, Dewey Beach, DE 19971
$4,200,000
$20,905/moEst:
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Single Family Residence
Built in 1974
$-- HOA
6,534 sqft lot
$589/sq.ft
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.
- Houzeo last checked: 3 hours ago
- Listing updated: October 30, 2026 at 6:22 pm
- Listing Provided by: BRUCE WRIGHT (302) 542-7651 , Joanie Hannigan (302) 519-1455 | Mann & Sons, Inc. (302) 227-9477
- Source: Bright MLS-NJ | MLS#: DESU2116162

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1974
HOA Fees
-
Finished Area
7,136 sqft
Lot Size
6,534 sqft lot
Basement Area
- sqft
MLS Name
Bright MLS
MLS Number
DESU2116162
MLS Status
ACTIVE-BRIGHT
Days on Market
107

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 8
Bathrooms: 7
Interior
Heating
Heat Pump Gas Back Up, Heat Pump(s), Other
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
Window Features
Double Hung, Double Pane Windows, Energy Efficient, Insulated, Screens, Sliding, Vinyl Clad
Exterior Features
Chimney Cap(s), Extensive Hardscape, Exterior Lighting, Flood Lights, Gutter System, Lawn Sprinkler, Outside Shower, Roof Deck, Street Lights, Underground Lawn Sprinkler
Cooling
Central A/c
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
Sewer
Public Sewer
Flooring
Carpet, Ceramic Tile, Hardwood
Construction
Year Built
Year Built: 1974
Home type
Single Family Residence
Property Condition
Excellent
Construction Materials
Masonry, Asphalt, Batts Insulation, Blown In Insulation, Concrete, Cpvc/pvc, Frame, Shake Siding, Stick Built, Tile, Vinyl Siding
Architectural Style
Coastal
Roof
Architectural Shingle, Flat, Pitched
Foundation Details
Block
Utilities & Energy
Electric
200+ Amp Service
Basement
Partial
Fireplace Features
Fireplace Glass Doors, Gas/propane
Water Source
Public
Utilities
Cable Tv, Phone, Propane, Sewer Available, Water Available
Security Features
Security System, Smoke Detector
Other Features
Patio And Porch Features
Balconies Multiple, Porch, Roof, Screened
Subdivision Name
Rehoboth By The Sea
Price History
| Date | Event | Price |
|---|---|---|
08/13/2026 Source: | Price Decreased | $4,200,000 -4.55% $589/sqft |
07/27/2026 Source: | Price Decreased | $4,400,000 -8.33% $617/sqft |
07/16/2026 Source: | Price Increased | $4,800,000 +14.29% $673/sqft |
07/16/2026 Source: | Listed for Sale | $4,200,000 $589/sqft |
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Based on information from Bright MLS through Nov 05, 2026, 12:45PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information
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