Property

Dewey Beach, DE 19971 105 Chicago Street

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Presented By: BRUCE WRIGHT with Mann & Sons, Inc. - 3022279477; info@mannandsons.com
  • MLS# DESU2116162
  • 07/15/2026
  • Request Tour
  • Request Info
  • Beds • 7
  • Baths • 7
  • SQFT • 7,136
  • Garage • 2

Home Details

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 showerperfect 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.
Presented By: BRUCE WRIGHT with Mann & Sons, Inc. - 3022279477; info@mannandsons.com

Interior Features for 105 Chicago Street

Bedrooms

Main Level Bedrooms7
Total Bedrooms7

Bathrooms

Total Baths7

Other Interior Features

LivingAreaSourceEstimated
Below Grade Unfin Area UnitsSquare Feet
Below Grade Unfin SQFT0
Below Grade Unfin SQFT SourceAssessor
Above Grade Finished Area6274
Above Grade Finished Area SourceEstimated
Above Grade Finished Area Unit TypeSquare Feet
BasementPartial
Basement (Y/N)Yes
Below Grade Finished Area862
Below Grade Finished Area SourceEstimated
Below Grade Finished Area Unit TypeSquare Feet
Central Air Y/NYes
Fireplace FeaturesFireplace - Glass Doors, Gas/Propane
Fireplace Y/NYes
FlooringCarpet, Ceramic Tile, Hardwood
Heating FuelElectric, Geo-thermal, Propane - Leased
Heating Y/NYes
Hot WaterPropane, Electric, Multi-tank
Interior AmenitiesAttic, 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 Bedro
Laundry TypeLower Floor, Upper Floor
Number of Elevators1
Total Fireplaces3
Window FeaturesDouble Hung, Double Pane, Energy Efficient, Insulated, Screens, Sliding, Vinyl Clad

General for 105 Chicago Street

Acceptable FinancingCash, Conventional, FHA, VA, USDA
Accessibility36 + wide Halls, >84 Garage Door
Additional Parcels Y/NNo
AppliancesBuilt-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 -
Architectural StyleCoastal
Bathrooms Count Main Level7.00
Bathrooms Full Main Level7
Building NameNONE AVAILABLE
CityDEWEY BEACH
Condo/Coop Association fee Y/NNo
Construction MaterialsMasonry, Asphalt, Batts Insulation, Blown-In Insulation, Concrete, CPVC/PVC, Frame, Shake Siding, Stick Built, Tile, Vinyl Siding
Cool FuelElectric
CoolingCentral A/C
CountySUSSEX
DirectionsFrom RT1 turn at Fifer Store follow to Chicago Street follow toward OCEAN home is on left see sign in yard.
DisclosuresFlood Zone, Lead Based Paint - Federal, Prop Disclosure, Radon
Electric200+ Amp Service
Facing DirectionSouth
Full Baths7
Garage Spaces2.00
Garage Y/NYes
HOANo
HeatingHeat Pump - Gas BackUp, Heat Pump(s), Other
Historic Y/NNo
Home Warranty Y/NNo
Lease Considered Y/NNo
Legal SubdivisionRehoboth By The Sea
Levels4
Living Area7136
Lot Size Square Feet6534.00
Lot Size UnitsSquare Feet
MLS AreaLewes Rehoboth Hundred (31009)
New ConstructionNo
Other StructuresAbove Grade, Below Grade
OwnershipFee Simple
Patio/Porch FeaturesBalconies- Multiple, Porch(es), Roof, Screened
PossessionSettlement
Price Per Sq Ft Total AG669.43
Property ConditionExcellent
Property TypeResidential
RoofArchitectural Shingle, Flat, Pitched
School DistrictCAPE HENLOPEN
Security FeaturesSecurity System, Smoke Detector
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusACTIVE
Structure TypeDetached
Subdivision NameREHOBOTH BY THE SEA
Sussex DE QuadrantsEast of Rt 1
Tax Annual Amount3768.8
Tax Year2025
Total SQFT7136
UtilitiesCable TV, Phone, Propane, Sewer Available, Water Available
Vacation Rental Y/NNo
ViewOcean
Water Access Y/NNo
Year Built1974
Year Built SourceAssessor
ZoningTN

Exterior for 105 Chicago Street

# of Attached Garage Spaces2
Door FeaturesSix Panel, Insulated
Exterior AmenitiesChimney Cap(s), Extensive Hardscape, Exterior Lighting, Flood Lights, Gutter System, Lawn Sprinkler, Outside Shower, Roof Deck, Street Lights, Underground Lawn Sprinkler
FencingPanel, Rear
Foundation DetailsBlock
Garage FeaturesGarage - Side Entry, Garage Door Opener, Inside Access, Oversized
Horse Y/NNo
Land Use Code1 1
Lot Dimensions66.00 x 100.00
Lot Size Acres0.15
Lot Size SourceAssessor
LotDimensionsSourceAssessor
Navigable Water Y/NNo
PoolNo Pool
Road ResponsibilityPublic
Road Surface TypeBlack Top
Soil TypesUnknown
SpaNo
Total Parking Spaces8
Type of ParkingAttached Garage, Driveway, Off Street, Other
Water Oriented Y/NNo
Water SourcePublic
Water View Y/NYes
Waterfront Y/NNo

Additional Details

Price History

Schools

Elementary School N/A
Middle School N/A
High School Cape Henlopen High School

Tina Torres

Broker/Owner
Price $4,200,000
MLS#DESU2116162
List Date 07/15/2026
Property Type Single Family
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