105 Chicago St Dewey Beach, DE 19971
Dewey Beach AreaEstimated payment $23,545/month
Highlights
- Ocean View
- Rooftop Deck
- Coastal Architecture
- Second Kitchen
- Gourmet Galley Kitchen
- Traditional Floor Plan
About This Home
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.
Listing Agent
(302) 227-9477 info@mannandsons.com Mann & Sons, Inc. Brokerage Phone: 3022279477 License #RS-0016583 Listed on: 07/16/2026
Co-Listing Agent
(302) 227-9477 info@mannandsons.com Mann & Sons, Inc. Brokerage Phone: 3022279477
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $5,522
Year Built
- Built in 1974
Lot Details
- 6,534 Sq Ft Lot
- Lot Dimensions are 66.00 x 100.00
- South Facing Home
- Back Yard Fenced
- Panel Fence
- Extensive Hardscape
- Sprinkler System
- Property is in excellent condition
- Property is zoned TN
Parking
- 2 Car Direct Access Garage
- 6 Driveway Spaces
- Oversized Parking
- Side Facing Garage
- Garage Door Opener
- Off-Street Parking
Home Design
- Coastal Architecture
- Flat Roof Shape
- Block Foundation
- Frame Construction
- Blown-In Insulation
- Batts Insulation
- Pitched Roof
- Architectural Shingle Roof
- Shake Siding
- Vinyl Siding
- Stick Built Home
- CPVC or PVC Pipes
- Chimney Cap
- Asphalt
- Masonry
- Tile
Interior Spaces
- Property has 4 Levels
- 1 Elevator
- Traditional Floor Plan
- Wet Bar
- Sound System
- Ceiling Fan
- Recessed Lighting
- 3 Fireplaces
- Fireplace With Glass Doors
- Gas Fireplace
- Double Pane Windows
- Vinyl Clad Windows
- Insulated Windows
- Double Hung Windows
- Sliding Windows
- Window Screens
- Insulated Doors
- Six Panel Doors
- Family Room Off Kitchen
- Combination Kitchen and Dining Room
- Ocean Views
- Partial Basement
- Attic
Kitchen
- Gourmet Galley Kitchen
- Second Kitchen
- Breakfast Area or Nook
- Butlers Pantry
- Double Self-Cleaning Oven
- Gas Oven or Range
- Built-In Range
- Stove
- Built-In Microwave
- Ice Maker
- Dishwasher
- Stainless Steel Appliances
- Upgraded Countertops
- Wine Rack
- Disposal
Flooring
- Wood
- Carpet
- Ceramic Tile
Bedrooms and Bathrooms
- 7 Main Level Bedrooms
- En-Suite Bathroom
- Walk-In Closet
- 7 Full Bathrooms
- Bathtub with Shower
- Walk-in Shower
Laundry
- Laundry on lower level
- Stacked Electric Washer and Dryer
Home Security
- Home Security System
- Intercom
- Fire and Smoke Detector
- Flood Lights
Accessible Home Design
- Halls are 36 inches wide or more
- Garage doors are at least 85 inches wide
Eco-Friendly Details
- Energy-Efficient Appliances
- Energy-Efficient Windows
Outdoor Features
- Outdoor Shower
- Multiple Balconies
- Rooftop Deck
- Screened Patio
- Exterior Lighting
- Rain Gutters
- Porch
Schools
- Cape Henlopen High School
Utilities
- Air Filtration System
- Central Air
- Heat Pump System
- Back Up Gas Heat Pump System
- Heating System Powered By Leased Propane
- Geothermal Heating and Cooling
- 200+ Amp Service
- Multi-Tank Propane Water Heater
- Tankless Water Heater
- Phone Available
- Cable TV Available
Community Details
- No Home Owners Association
- Rehoboth By The Sea Subdivision
Listing and Financial Details
- Assessor Parcel Number 334-20.14-133.00
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $3,380 | $100,700 | $13,200 | $87,500 |
| 2024 | $4,782 | $100,700 | $13,200 | $87,500 |
| 2023 | $4,778 | $100,700 | $13,200 | $87,500 |
| 2022 | $4,605 | $100,700 | $13,200 | $87,500 |
| 2021 | $4,661 | $100,700 | $13,200 | $87,500 |
| 2020 | $4,645 | $100,700 | $13,200 | $87,500 |
| 2019 | $4,631 | $100,700 | $13,200 | $87,500 |
| 2018 | $4,022 | $100,700 | $0 | $0 |
| 2017 | $3,835 | $100,700 | $0 | $0 |
| 2016 | $3,570 | $100,700 | $0 | $0 |
| 2015 | $3,391 | $100,700 | $0 | $0 |
| 2014 | $3,363 | $100,700 | $0 | $0 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 08/13/2026 08/13/26 | Price Changed | $4,200,000 | -4.5% | $589 / Sq Ft |
| 07/27/2026 07/27/26 | Price Changed | $4,400,000 | -8.3% | $617 / Sq Ft |
| 07/16/2026 07/16/26 | For Sale | $4,800,000 | -- | $673 / Sq Ft |
Source: Bright MLS
MLS Number: DESU2116162
APN: 334-20.14-133.00
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