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For sale
    • Price cut: $200K (8/13)
    $4,200,000

    105 Chicago St, Dewey Beach, DE 19971

    7beds
    7,136sqft
    : 
    $25,633/mo
    Get pre-qualified
    Single Family Residence
    Built in 1974
    6,534 Square Feet Lot
    $-- Zestimate®
    $589/sqft
    $-- HOA

    What's special

    Outdoor showerMultiple balconiesWine storageRecessed lightingExtensive hardscapingWindow treatmentsWalk-in closets
    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.
    69 days
    698
    9

    Zillow last checked:

    Listing updated:

    Listed by:

    BRUCE WRIGHT 302-542-7651,

    Mann & Sons, Inc. (302) 227-9477,

    Co-Listing Agent: Joanie Hannigan 302-519-1455,

    Mann & Sons, Inc.

    Source: Bright MLS,MLS#: DESU2116162MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 7
      • Bathrooms: 7
      • Full bathrooms: 7
      • Main level bathrooms: 7
      • Main level bedrooms: 7
      Basement
      • Area: 862
      Heating
      • Heat Pump, Other, Electric, Geothermal, Propane
      Cooling
      • Central Air, Electric
      Appliances
      • Included: Microwave, Built-In Range, Cooktop, Dishwasher, Disposal, Dryer, Energy Efficient Appliances, Ice Maker, Intercom, Double Oven, Self Cleaning Oven, Oven, Oven/Range - Electric, Oven/Range - Gas, Refrigerator, Stainless Steel Appliance(s), Washer, Washer/Dryer Stacked, Water Heater, Tankless Water Heater, Electric Water Heater
      • Laundry: Lower Level, Upper Level
      Features
      • Attic, 2nd Kitchen, Air Filter System, Bathroom - Stall Shower, Bathroom - Tub Shower, Breakfast Area, Butlers Pantry, Ceiling Fan(s), Combination Kitchen/Dining, Dining Area, Elevator, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Traditional, Kitchen - Country, Kitchen - Galley, Kitchen - Gourmet, Pantry, Primary Bath(s), Recessed Lighting, Sound System, Upgraded Countertops, Walk-In Closet(s), Bar, Wine Storage, Dry Wall
      • Flooring: Carpet, Ceramic Tile, Hardwood, Wood
      • Doors: Six Panel, Insulated
      • Windows: Double Hung, Double Pane Windows, Energy Efficient, Insulated Windows, Screens, Sliding, Vinyl Clad, Window Treatments
      • Basement: Partial
      • Number of fireplaces: 3
      • Fireplace features: Glass Doors, Gas/Propane
      Interior area
      • Total structure area: 7,136
      • Total interior livable area: 7,136 sqft
      • Finished area above ground: 6,274
      • Finished area below ground: 862

      Property

      Parking
      • Total spaces: 8
      • Parking features: Garage Faces Side, Garage Door Opener, Inside Entrance, Oversized, Attached, Driveway, Off Street, Other
      • Attached garage spaces: 2
      • Uncovered spaces: 6
      Accessibility
      • Accessibility features: Accessible Hallway(s), >84" Garage Door
      Features
      • Levels: Four
      • Stories: 4
      • Patio & porch: Porch, Roof, Screened, Roof Deck
      • Exterior features: Chimney Cap(s), Extensive Hardscape, Lighting, Flood Lights, Rain Gutters, Lawn Sprinkler, Outdoor Shower, Street Lights, Underground Lawn Sprinkler, Balcony
      • Pool features: None
      • Fencing: Panel,Back Yard
      • Has view: Yes
      • View description: Ocean
      • Has water view: Yes
      • Water view: Ocean
      Lot
      • Size: 6,534 Square Feet
      • Dimensions: 66.00 x 100.00
      • Features: Unknown Soil Type
      Details
      • Additional structures: Above Grade, Below Grade
      • Parcel number: 33420.14133.00
      • Zoning: TN
      • Special conditions: Standard
      • Other equipment: Intercom

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Coastal
      • Property subtype: Single Family Residence
      Materials
      • Masonry, Asphalt, Batts Insulation, Blown-In Insulation, Concrete, CPVC/PVC, Frame, Shake Siding, Stick Built, Tile, Vinyl Siding
      • Foundation: Block
      • Roof: Architectural Shingle,Flat,Pitched
      Condition
      • Excellent
      • New construction: No
      • Year built: 1974

      Utilities & green energy

      • Electric: 200+ Amp Service
      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Connected, Phone, Propane, Sewer Available, Water Available, Cable

      Community & HOA

      Community
      • Security: Security System, Smoke Detector(s)
      • Subdivision: Rehoboth By The Sea
      HOA
      • Has HOA: No
      Location
      • Region: Dewey Beach

      Financial & listing details

      • Price per square foot: $589/sqft
      • Tax assessed value: $1,686,300
      • Annual tax amount: $3,768
      • Date on market: 7/16/2026
      • Listing agreement: Exclusive Right To Sell
      • Listing terms: Cash,Conventional,FHA,VA Loan,USDA Loan
      • Ownership: Fee Simple
      • Road surface type: Black Top

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/13/2026Price change$4,200,000-4.5%$589/sqft
        Source: Bright MLS #DESU2116162 Report a problem
        7/27/2026Price change$4,400,000-8.3%$617/sqft
        Source: Bright MLS #DESU2116162 Report a problem
        7/16/2026Listed for sale$4,800,000$673/sqft
        Source: Bright MLS #DESU2116162 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$3,380 -29.3%$843,150 +737.3%
        2024$4,782 +0.1%$100,700
        2023$4,778 +3.8%$100,700
        2022$4,605 -1.2%$100,700
        2021$4,661 +0.3%$100,700
        2020$4,645 $100,700
        2019$4,645 +0.3%$100,700
        2018$4,631 +15.1%$100,700
        2017$4,022 +12.7%$100,700
        2016$3,570 +5.3%$100,700
        2015$3,391 +0.8%$100,700
        2014$3,363 +3.3%$100,700
        2013$3,255 -15.5%$100,700
        2012$3,850 +11.2%$100,700
        2011$3,462 $100,700
        2010$3,462 -2.8%$100,700
        2009$3,562 $100,700
        2008-- --
        2007-- --
        2006-- --
        2005-- --
        2004-- --
        2003-- --
        2002-- --
        2001-- --
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 19971

        Getting around

        45 / 100
        Car-Dependent
        66 / 100
        Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • High: Cape Henlopen
        • District: Cape Henlopen

        Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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