Date
Details
Price
Change
Source
7/16/2026
Listed
$4,800,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$4,800,000 Just Listed
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Property 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.
Full Property Details
Full Property Details for 105 Chicago St
General
- Price: $4,800,000
- Taxes: $5,522 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: DESU2116162
- Updated: 7/16/2026
- Added to Site: 5 day(s) ago
Interior
- Interior Features: Attic, 2nd Kitchen, Air Filter System, Bathroom - Jetted Tub, 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
- Fireplace: Yes
- Number of Fireplaces: 3
- Fireplace(s): Fireplace - Glass Doors, Gas/Propane
- 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
- Flooring: Carpet, Ceramic Tile, Hardwood, Laminate Plank
Rooms
Bathrooms
- Total Bathrooms: 7
- Full Bathrooms: 7
- Main Floor Baths: 7
- Main - Full Baths: 7
Bedrooms
- Total Bedrooms: 7
- Bedrooms Main & Up: 7
Other Rooms
- Laundry: Lower Floor, Upper Floor
Additional Information
- Security/Safety: Security System, Smoke Detector
Exterior
- Exterior Features: Chimney Cap(s), Extensive Hardscape, Exterior Lighting, Flood Lights, Gutter System, Lawn Sprinkler, Outside Shower, Roof Deck, Street Lights, Underground Lawn Sprinkler
- Porch/Patio/Deck: Balconies- Multiple, Porch(es), Roof, Screened
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 8
- Parking Type: Attached Garage, Driveway, Off Street, Other
- Garage Description: Garage - Side Entry, Garage Door Opener, Inside Access, Oversized
Location
- Area: Lewes Rehoboth Hundred (31009)
- County: SUSSEX
- Subdivision: REHOBOTH BY THE SEA
- Driving Directions: From RT1 turn at Fifer Store follow to Chicago Street follow toward OCEAN home is on left see sign in yard.
- Direction Faces: South
- City Limits: Yes
School Information
- School District: Cape Henlopen
- High School: Cape Henlopen
Community
- Pets Allowed: Yes
- Pets: No Pet Restrictions
Heating & Cooling
- Central air: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Heat Pump - Gas BackUp, Heat Pump(s), Other
- Heating Fuel: Electric, Geo-thermal, Propane - Leased
- Water Heater: Propane
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV, Phone, Propane, Sewer Available, Water Available
Structural Information
- Architectural Style: Coastal
- Structure Type: Detached
- Construction: Masonry, Asphalt, Batts Insulation, Blown-In Insulation, Concrete, CPVC/PVC, Frame, Shake Siding, Stick Built, Tile, Vinyl Siding
- Basement: Yes
- Basement Desc.: Partial
- Foundation: Block
- Roof: Architectural Shingle, Flat, Pitched
- Walls/Ceilings: Dry Wall
- Windows: Double Hung, Double Pane, Energy Efficient, Insulated, Screens, Sliding, Vinyl Clad
- Doors: Six Panel, Insulated
- Elevator(s ): 1
- Stories Description: Main
- Square Feet: 7,136
- Sq. Ft. Source: Estimated
- Living Area: 7,136 Sq. Ft.
- Finished Above Grnd: 6,274 Sq. Ft.
- Finished Below Grnd: 862 Sq. Ft.
- Year Built: 1974
- Year Built Source: Assessor
- Property Condition: Excellent
Lot Features
- Property View: Ocean
- Lot Size (Acres): 0.15
- Lot Size (Sq. Ft.): 6,534
- Lot Size Source: Assessor
- Lot Dimensions: 66.00 x 100.00
- Street/Road Desc.: Black Top
- Zoning: TN
- Fencing (Description): Panel, Rear
Water Features
- Water View: Yes
Financial Considerations
- Price Per Sq. Ft.: $765.06
- Assessment Year: 2025
- School Tax: $3,201
- City/TownTax: $1,960
- City/TownTax Freq: Annually
- County Tax: $361
- County Tax Freq: Annually
- Tax Amount: $5,522
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
Listed by Mann & Sons, Inc., BRUCE WRIGHT and Mann & Sons, Inc., Joanie Hannigan
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 105 Chicago St —
BRUCE WRIGHT
Mann & Sons, Inc.
Joanie Hannigan
Mann & Sons, Inc.
Listing Office Email: info@mannandsons.com
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 105 Chicago St
School District:Cape Henlopen School District
| Name | Grades | Distance |
|---|---|---|
Rehoboth Elementary School 500 Stockley Street, Rehoboth Beach, DE 19971 | PK-6 | 0.9 mi |
Beacon Middle School 19483 John J Williams Highway, Lewes, DE 19958 | 4-8 | 4 mi |
Cape Henlopen High School 1250 Kings Highway, Lewes, DE 19958 | 8-12 | 5.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 105 Chicago St
Tax History
Tax History for 105 Chicago St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,380
-29%
$100,700
—
2023
$4,778
4%
$100,700
—
2022
$4,605
-1%
$100,700
—
2021
$4,661
—
$100,700
—
2020
$4,645
—
$100,700
—
2019
$4,631
15%
$100,700
—
2018
$4,022
5%
$100,700
—
2017
$3,835
7%
$100,700
—
2016
$3,570
5%
$100,700
—
2015
$3,391
1%
$100,700
—
2014
$3,363
3%
$100,700
—
2013
$3,255
—
$100,700
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 105 Chicago St
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Listed by Jack Lingo - Rehoboth, Jason Abela
Sold by The Real McCoy Group
Sold by The Real McCoy Group
105 Chicago Street, Dewey Beach, DE 19971 (MLS# DESU2116162) is a Single Family property with 7 bedrooms and 7 full bathrooms. 105 Chicago Street is currently listed for $4,800,000 and was received on July 16, 2026. Want to learn more about 105 Chicago Street? Do you have questions about finding other Single Family real estate for sale in Dewey Beach? You can browse all Dewey Beach real estate or contact a Coldwell Banker agent to request more information.