Skip To Content

105 Chicago Street

DEWEY BEACH, DE 19971
  • $4,200,000
  • STATUS: Active
  • ON SITE: 57 Days
  • ID#: DESU2116162
UPDATED: 87 min ago
$4,200,000
  • 7
    BEDS
  • 0.15
    ACRES
  • 7
    BATHS
  • 0
    1/2 BATHS
  • 7,136
    SQFT
  • $589
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1974
County:

School Information

High School:
School District:

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 heaterAir filtration systemSecurity system and smoke detectors36-inch-plus wide hallways and an oversized 84-inch garage door for enhanced accessibilityInsulated six-panel doors and energy-efficient double-pane, vinyl-clad windows with screensCeiling fans, window treatments, and abundant storage throughoutThe 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 Highlights7 Bedrooms7 BathroomsSpacious rooftop deck with beautiful beach viewsGourmet kitchen plus second kitchenElevator3 Gas fireplacesWine storage and wet barMultiple balconies and screened porchOutdoor showerExtensive hardscaping and irrigation systemNo HOA pool to maintainPrime location near Dewey Beach, Rehoboth Beach, restaurants, shopping, and local attractionsThis extraordinary beach home combines luxury, functionality, and an unbeatable location, making it an exceptional primary residence, vacation retreat, or investment opportunity.

Monthly Payment Calculator



©2026 Bright MLS, All Rights Reserved. IDX information is provided exclusively 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. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or The Matt Lenza Real Estate Team | Crown Homes Real Estate. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2026-09-10T23:53:50.22.
www.lenzateam.com/homes/178853531
Print Image

105 Chicago Street DEWEY BEACH, DE 19971

  • Price: $4,200,000
  • Status: Active
  • On Site: 57 Days
  • Updated: 87 min ago
  • ID#: DESU2116162
7
Beds
7
Baths
0
½ Baths
0.15
Acres
7,136
SQFT
$589
$/SQFT
1974
Built
Neighborhood:
Rehoboth By The Sea
County:
Sussex
Area:
Lewes Rehoboth Hundred (31009)
High School:
Cape Henlopen
School District:
Cape 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 heaterAir filtration systemSecurity system and smoke detectors36-inch-plus wide hallways and an oversized 84-inch garage door for enhanced accessibilityInsulated six-panel doors and energy-efficient double-pane, vinyl-clad windows with screensCeiling fans, window treatments, and abundant storage throughoutThe 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 Highlights7 Bedrooms7 BathroomsSpacious rooftop deck with beautiful beach viewsGourmet kitchen plus second kitchenElevator3 Gas fireplacesWine storage and wet barMultiple balconies and screened porchOutdoor showerExtensive hardscaping and irrigation systemNo HOA pool to maintainPrime location near Dewey Beach, Rehoboth Beach, restaurants, shopping, and local attractionsThis extraordinary beach home combines luxury, functionality, and an unbeatable location, making it an exceptional primary residence, vacation retreat, or investment opportunity.
Exterior Features

Architectural Style Coastal Construction Materials MasonryAsphaltBatts InsulationBlown-In InsulationConcreteCPVC/PVCFrameShake SidingStick BuiltTileVinyl Siding Door Features Six PanelInsulated Exterior Features Chimney Cap(s)Extensive HardscapeExterior LightingFlood LightsGutter SystemLawn SprinklerOutside ShowerRoof DeckStreet LightsUnderground Lawn Sprinkler Fencing PanelRear Garage Spaces 2.00 Garage Type Garage - Side EntryGarage Door OpenerInside AccessOversized Garage YN Yes Parking Types Attached GarageDrivewayOff StreetOther Patio And Porch Features Balconies- MultiplePorch(es)RoofScreened Pool No Pool Property Condition Excellent Road Responsibility Public Road Surface Type Black Top Roof Architectural ShingleFlatPitched Soil Types Unknown View Ocean Water Access YN No Water View YN Yes Waterfront YN No

Interior Features

Above Grade Fin SQFT 6274 Appliances Built-In MicrowaveBuilt-In RangeCooktopDishwasherDisposalDryer - ElectricDryer - Front LoadingEnergy Efficient AppliancesIcemakerIntercomMicrowaveOven - DoubleOven - Self CleaningOven - SingleOven/Range - ElectricOven/Range - GasRefrigeratorStainless Steel AppliancesStoveWasher - Front LoadingWasherWasher/Dryer StackedWater HeaterWater Heater - Tankless Basement Partial Basement YN Yes Below Grade Finished Area 862 Below Grade Unfinished Area 0 Cooling Central A/C Fireplace Features Fireplace - Glass DoorsGas/Propane Fireplace YN Yes Fireplaces Total 3 Flooring CarpetCeramic TileHardwood Furnished No Heating Heat Pump - Gas BackUpHeat Pump(s)Other Heating YN Yes Interior Features Attic2nd KitchenAir Filter SystemBathroom - Stall ShowerBathroom - Tub ShowerBreakfast AreaButlers PantryCarpetCeiling Fan(s)Combination Kitchen/DiningDining AreaElevatorEntry Level BedroomFamily Room Off KitchenFloor Plan - TraditionalIntercomKitchen - CountryKitchen - GalleyKitchen - GourmetPantryPrimary Bath(s)Recessed LightingSound SystemUpgraded CountertopsWalk-in Closet(s)Wet/Dry BarWindow TreatmentsWine StorageWood Floors Laundry Type Lower FloorUpper Floor Levels 4 Main Level Bedrooms 7 Pets Allowed No Pet Restrictions Security Features Security SystemSmoke Detector Spa YN No Walls Ceilings Dry Wall

Property Features

Acceptable Financing CashConventionalFHAVAUSDA Accessibility Features 36"+ wide Halls>84" Garage Door Association YN No Central Air YN Yes Condo YN No Cooling Fuel Electric Electric 200+ Amp Service Elevators 1 Federal Flood Zone YN No Foundation Details Block Heating Fuel ElectricGeo-thermalPropane - Leased Historic YN No Horse YN No Hot Water PropaneElectricMulti-tank Lease Considered YN No Navigable Water YN N New Construction YN No Original MLSNumber 805158355906 Ownership Interest Fee Simple Pets Allowed YN Yes Sale Type Standard Senior Community YN No Sewer Public Sewer Structure Design Type Detached Tax Annual Amount 3768.80 Utilities Cable TVPhonePropaneSewer AvailableWater Available Vacation Rental YN No Water Source Public Window Features Double HungDouble PaneEnergy EfficientInsulatedScreensSlidingVinyl Clad Zoning TN

Listing courtesy of Mann & Sons, Inc.: .


©2026 Bright MLS, All Rights Reserved. IDX information is provided exclusively 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. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or The Matt Lenza Real Estate Team | Crown Homes Real Estate. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2026-09-10T23:53:50.22.
 
https://bt-photos.global.ssl.fastly.net/brightmls/1280_boomver_1_805158355906-2.jpg https://bt-photos.global.ssl.fastly.net/brightmls/1280_boomver_1_805158355906-2.jpg https://bt-photos.global.ssl.fastly.net/brightmls/1280_boomver_1_805158355906-2.jpg
Logo
The Matt Lenza Real Estate Team | Crown Homes Real Estate
514 Ivydale Rd, Wilmington
Media DE, 19803