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Single family home for sale at 105 Chicago St, Dewey Beach, DE 19971 | MLS# DESU2116162 | Listing updated on 2026-10-30
Photo 1 of Single family home for sale at 105 Chicago St, Dewey Beach, DE 19971 | MLS# DESU2116162 | Listing updated on 2026-10-30
Photo 2 of Single family home for sale at 105 Chicago St, Dewey Beach, DE 19971 | MLS# DESU2116162 | Listing updated on 2026-10-30
Photo 3 of Single family home for sale at 105 Chicago St, Dewey Beach, DE 19971 | MLS# DESU2116162 | Listing updated on 2026-10-30
Photo 4 of Single family home for sale at 105 Chicago St, Dewey Beach, DE 19971 | MLS# DESU2116162 | Listing updated on 2026-10-30
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Street View

$4,200,000

Monthly Est:$20,905

  • Beds Icon8 Beds
  • Beds Icon
    7 Baths
  • Beds Icon7,136sqft

105 Chicago St, Dewey Beach, DE 19971

$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 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Sussex De County

  • City

    Dewey Beach

  • 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

DateEventPrice

08/13/2026

Source: mls_logoBright MLS-NJ #DESU2116162

Price Decreased

$4,200,000 -4.55%

$589/sqft

07/27/2026

Source: mls_logoBright MLS-NJ #DESU2116162

Price Decreased

$4,400,000 -8.33%

$617/sqft

07/16/2026

Source: mls_logoBright MLS-NJ #DESU2116162

Price Increased

$4,800,000 +14.29%

$673/sqft

07/16/2026

Source: mls_logoBright MLS-NJ #DESU2116162

Listed for Sale

$4,200,000

$589/sqft

Nearby Homes

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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