About This Home

This 7-bedroom, 7-bathroom single family at 105 CHICAGO Street in Dewey Beach, DE is listed for $4,200,000 ($589 per sqft). Built in 1974, the home offers 7,136 sqft of living space on a 0.15 acres lot.

Key Features

  • Built in 1974
  • 0.15 acre lot
  • 4 stories
  • 8 parking spaces
  • Fireplace

Property Details

4 stories
7 full
8 spaces
1974

Amenities

FireplaceA/C
Listing 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 hall

ways 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, r

estaurants, 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.

Monthly Cost Estimate

$22,462/mo

20% down · 6.5% · 30 years

Principal$3,037
Interest$18,200
Insurance$1,225

Estimates only. Actual payments may vary.

Location

105 CHICAGO Street

Dewey Beach, DE 19971

REHOBOTH BY THE SEA

Features & Amenities

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

Property Details

Construction

Masonry Asphalt BattsInsulation BlownInInsulation Concrete CPVC/PVC Frame Shake Siding Stick Built Tile Vinyl Siding

Parking

Garage - AttachedOff StreetDriveway

Heating

Heat Pump (Heating)Natural Gas

Cooling

Central Air

Appliances

Built-In MicrowaveBuilt-In RangeCooktopDishwasherDisposalDryer - ElectricDryer - Front LoadingEnergy Efficient AppliancesIcemakerIntercomMicrowaveOven - DoubleOven - Self CleaningOven - SingleOven/Range - ElectricOven/Range - GasRefrigeratorStainless Steel AppliancesStoveWasher - Front LoadingWasherWasher/Dryer StackedWaterHeaterWater Heater - Tankless

Questions & Answers

This 7-bedroom, 7-bathroom single family at 105 CHICAGO Street is listed at $4,200,000 ($589/sqft). The estimated monthly payment is $22,462 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1974, 0.15 acre lot, 4 stories, 8 parking spaces, Fireplace. Interior Features: Attic, 2nd Kitchen, Air Filter System.

This property is listed by BRUCE WRIGHT and can be reached at 3025427651.

BW

BRUCE WRIGHT

License RS-0016583

Agent at Mann & Sons, Inc. REALTORS®

(302) 542-7651
Agent website

Listed by Mann & Sons, Inc. REALTORS® · Broker phone: (302) 470-7600 · View on Broker Site · Broker website

MLS# DESU2116162· Source: Bright MLS· 69 days on PropertySimple

Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

105 CHICAGO Street, Dewey Beach, DE 19971

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