Tammy Hess

105 Chicago Street

Dewey Beach, DE
$ 4,200,000 Beds 7 Baths 7 Sq 7,136
Monthly Estimate* How much can I afford?

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.

ACTIVE

  • Price
  • $ 4,200,000
  • City
  • Dewey Beach
  • Bedrooms
  • 7
  • Full Bathrooms
  • 7
  • County
  • SUSSEX
  • Half Bathrooms
  • 0
  • Area
  • Lewes Rehoboth Hundred
  • Lot Size
  • 0.15 Acres
  • Zip
  • 19971
  • Sqr Footage
  • 7,136
  • Year Built
  • 1974
  • Taxes
  • $ 3768
  • Style
  • Coastal
  • MLS#
  • DESU2116162
Listed By: BRUCE WRIGHT with Mann & Sons, Inc. - 3022279477;
Data Source: Bright MLS

Features

General

Living Area 7136
Sewer Public Sewer
Heating Heat Pump - Gas BackUp,Heat Pump(s),Other
Cooling Central A/C
Utilities Cable TV,Phone,Propane,Sewer Available,Water Available
Possession Settlement
Roof Architectural Shingle,Flat,Pitched
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 -
Zoning TN
Garage Spaces 2.00
Patio/Porch Features Balconies- Multiple,Porch(es),Roof,Screened
Architectural Style Coastal
Security Features Security System,Smoke Detector
Construction Materials Masonry,Asphalt,Batts Insulation,Blown-In Insulation,Concrete,CPVC/PVC,Frame,Shake Siding,Stick Built,Tile,Vinyl Siding
School District CAPE HENLOPEN
Year Built 1974
Electric 200+ Amp Service
View Ocean
Levels 4
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Building Name NONE AVAILABLE
Accessibility 36 + wide Halls,>84 Garage Door
County SUSSEX
New Construction No
Property Type Residential
HOA No
Subdivision Name REHOBOTH BY THE SEA
Facing Direction South
Garage Y/N Yes
Water Access Y/N No
Other Structures Above Grade,Below Grade
Full Baths 7
Status ACTIVE
Directions From RT1 turn at Fifer Store follow to Chicago Street follow toward OCEAN home is on left see sign in yard.
City DEWEY BEACH
Disclosures Flood Zone,Lead Based Paint - Federal,Prop Disclosure,Radon
Senior Community Y/N No
MLS Area Lewes Rehoboth Hundred (31009)
Lot Size Units Square Feet
Lot Size Square Feet 6534.00
Tax Annual Amount 3768.8
Home Warranty Y/N No
Property Condition Excellent
Structure Type Detached
Condo/Coop Association fee Y/N No
Bathrooms Full Main Level 7
Bathrooms Count Main Level 7.00
Price Per Sq Ft Total AG 669.43
Acceptable Financing Cash,Conventional,FHA,VA,USDA
Additional Parcels Y/N No
Historic Y/N No
Lease Considered Y/N No
Vacation Rental Y/N No
Total SQFT 7136
Sussex DE Quadrants East of Rt 1
Standard Status Active
Year Built Source Assessor
Legal Subdivision Rehoboth By The Sea

Interior Features

Interior Amenities 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 Bedro
Heating Fuel Electric,Geo-thermal,Propane - Leased
Basement Partial
Flooring Carpet,Ceramic Tile,Hardwood
Total Fireplaces 3
Fireplace Features Fireplace - Glass Doors,Gas/Propane
Hot Water Propane,Electric,Multi-tank
Basement (Y/N) Yes
Heating Y/N Yes
Window Features Double Hung,Double Pane,Energy Efficient,Insulated,Screens,Sliding,Vinyl Clad
Fireplace Y/N Yes
Above Grade Finished Area 6274
Central Air Y/N Yes
Total Bedrooms 7
Below Grade Finished Area 862
Main Level Bedrooms 7
Below Grade Finished Area Unit Type Square Feet
LivingAreaSource Estimated
Laundry Type Lower Floor,Upper Floor
Below Grade Unfin Area Units Square Feet
Below Grade Unfin SQFT Source Assessor
Below Grade Finished Area Source Estimated
Above Grade Finished Area Source Estimated
Above Grade Finished Area Unit Type Square Feet
Total Baths 7
Number of Elevators 1

Exterior Features

Exterior Amenities Chimney Cap(s),Extensive Hardscape,Exterior Lighting,Flood Lights,Gutter System,Lawn Sprinkler,Outside Shower,Roof Deck,Street Lights,Underground Lawn Sprinkler
Pool No Pool
Fencing Panel,Rear
Water Source Public
Total Parking Spaces 8
Garage Features Garage - Side Entry,Garage Door Opener,Inside Access,Oversized
Type of Parking Attached Garage,Driveway,Off Street,Other
Land Use Code 1 1
Foundation Details Block
Spa No
Water View Y/N Yes
Lot Dimensions 66.00 x 100.00
Lot Size Acres 0.15
Road Surface Type Black Top
Lot Size Source Assessor
Waterfront Y/N No
Door Features Six Panel,Insulated
Soil Types Unknown
Road Responsibility Public
Horse Y/N No
Navigable Water Y/N No
Water Oriented Y/N No
# of Attached Garage Spaces 2
LotDimensionsSource Assessor

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Martinsburg, WV office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
Agent Photo

Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Unknown Elementary School
Middle School Unknown Middle School
High School Cape Henlopen High School

Price History

7/15/2026 Listed $4,800,000
7/27/2026 9% - $4,400,000
8/13/2026 5% - $4,200,000

Property vs Zip Code Average in 19971

Price
AVG $1.97M
$4.2M
Taxes
AVG $2,628
$3,768
Year Built
AVG 1999
1974
Visits
AVG 385
161
Data Provided by Inside Real Estate®

In The Neighborhood

Areas That We Cover

105 Chicago Street Dewey Beach, DE is a Single Family Home for sale at $4200000 with 7136 sqft and a lot size of 0.15 Acres Acre(s). 105 Chicago Street Dewey Beach has 7 bedrooms, 7 baths and was built in 1974. The property's zip code is 19971 which is in Dewey Beach, DE

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided 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.

Tammy Hess

Tammy Hess

304-995-4706

By pressing Contact Me, you agree that Weichert® may contact you via phone about your inquiry, which may involve the use of automated means. You are not required to consent as a condition of purchasing any property, goods or services. For any other information please read our Privacy Policy