16 Chicago Street Dewey Beach, DE $ 5,250,000
16 Chicago Street
$ 5,250,000
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16 Chicago Street

Dewey Beach, DE, 19971
$ 5,250,000
Bedrooms5 Baths4.2 Sq 4,500

Monthly Estimate*

$ 33,149

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Single Family Home for sale in Dewey Beach, DE

for $5,250,000 with 5 bedrooms and 4 full baths, 2 half baths. This 4,500 square foot home was built in 2000 on a lot size of 0.11.

Coastal Luxury with Ocean Views & Breezes! Experience the perfect blend of luxury, comfort, and coastal charm in this stunning, professionally renovated beach retreat. Designed for effortless indoor-outdoor living, this exceptional home captures sweeping Atlantic Ocean views, refreshing sea breezes, and sophisticated designer finishes throughout. Ideally situated on a fee simple ocean block lot in the sought-after Rehoboth by the Sea community in Dewey Beach, this remarkable residence was completely reimagined in 2020 by renowned architect Tony Beto and custom home builder Dewson. The extensive renovation included a new roof, siding, HVAC systems, decks, and beautifully redesigned interior and exterior living spaces. The welcoming foyer opens to a spacious first level featuring four generously sized bedrooms, including three private ensuite bedrooms. This level also offers a large laundry room complete with a built-in dog washing station, a convenient powder room, elevator access, and two outdoor living areas designed for gathering, relaxing, and enjoying the coastal lifestyle. Upstairs, the open-concept living space is both elegant and inviting. The gourmet kitchen, complete with high-end appliances and an oversized walk-in pantry, flows seamlessly into the dining area and spacious great room. A cozy fireplace anchors the space, while sliding glass doors lead to a covered deck with a pergola and panoramic ocean viewscreating the perfect setting for entertaining or simply unwinding by the sea. The luxurious owner's suite is a private sanctuary featuring its own deck, a double-sided fireplace, and a spa-inspired bath with a soaking tub, oversized tiled shower, dual vanities, and a private water closet. The ground level offers a spacious garage with coated floors, abundant storage, an outdoor shower, and a private fenced backyardideal for pets, outdoor enjoyment, or quiet relaxation after a day at the beach. Every detail of this home reflects exceptional craftsmanship and thoughtful design. Highlights include cathedral ceilings, hardwood flooring, custom millwork, shiplap accents, wainscoting, designer wallpaper, exquisite tilework, on-demand hot water, central vacuum, an elevator, and premium finishes throughout. Professionally furnished and offered move-in ready, this extraordinary coastal home is equally suited as a full-time residence, luxurious vacation retreat, or exceptional investment property with strong rental potential. Schedule your private showing or take the video tour to experience this extraordinary ocean-block retreat for yourself.

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Single Family Active

Price

$ 5,250,000

Bedrooms

5

Full Bath

4

Half Bath

2

Property Type

Single Family

Taxes

$ 5,068

Style

Coastal

Lot Size

0.11

Year Built

2000

Town/City

Dewey Beach

County/Region

Sussex

MLS | Web ID

DESU2116884

Features
General
Living Area 4500
Sewer Public Sewer
Heating Forced Air Heat Pump(s)
Cooling Central A/C Zoned
Possession Negotiable
Roof Architectural Shingle
Appliances Dishwasher Disposal Dryer - Electric Microwave Oven/Range - Gas Range Hood Refrigerator Washer
Zoning RESIDENTIAL
Garage Spaces 2.00
Patio/Porch Features Balcony Deck(s)
Architectural Style Coastal
Security Features Monitored Security System
Construction Materials Stick Built
School District CAPE HENLOPEN
Exclusions Artwork Decor Dishes Glassware Utensils Personal Items Bikes Beach Chairs.
Year Built 2000
View Ocean
Levels 3
Ownership Fee Simple
Cool Fuel Electric
Building Name NONE AVAILABLE
Accessibility Elevator
County SUSSEX
New Construction N
Property Type Residential
HOA N
Subdivision Name REHOBOTH BY THE SEA
Garage Y/N Y
Water Access Y/N N
Other Structures Above Grade
Full Baths 4
Status ACTIVE
Directions Ocean Block of Chicago Street in Rehoboth by the Sea in Dewey Beach
City DEWEY BEACH
Senior Community Y/N N
MLS Area Lewes Rehoboth Hundred (31009)
Lot Size Units Square Feet
Lot Size Square Feet 5000.00
Tax Annual Amount 5068.0
Property Condition Excellent
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 3
Bathrooms Count Main Level 4.00
Price Per Sq Ft Total AG 1166.67
Acceptable Financing Cash Conventional
Historic Y/N N
Vacation Rental Y/N N
Virtual Tour https://players.brightcove.net/5782667248001/default_default/index.html?videoId=6380112464112
Location Type Oceanblock
Sussex DE Quadrants East of Rt 1
Builder Name Dewson
Standard Status Active
Year Built Source Estimated
Association Recreation Fee N
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Interior
Interior Amenities Pantry Ceiling Fan(s) Elevator Window Treatments
Heating Fuel Propane - Leased
Flooring Carpet Hardwood Tile/Brick
Total Fireplaces 2
Fireplace Features Gas/Propane
Hot Water Propane
Basement (Y/N) N
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 4500
Half Baths 2
Central Air Y/N Y
Total Bedrooms 5
Room Type Dining Room Primary Bedroom Bedroom 2 Bedroom 3 Bedroom 4 Bedroom 5 Kitchen Foyer Great Room Laundry Storage Room Bathroom 2 Bathroom 3 Primary Bathroom Full Bath Half Bath
Main Level Bedrooms 4
Laundry Type Main Floor
Above Grade Finished Area Source Estimated
Above Grade Finished Area Unit Type Square Feet
Total Baths 6
Number of Elevators 1
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Exterior
Exterior Amenities Lawn Sprinkler Outside Shower
Pool No Pool
Parking Features Crushed Stone
Lot Features Landscaping
Water Source Public
Inclusions Furniture Televisions Bedding
Garage Features Garage Door Opener
Type of Parking Off Street Driveway Attached Garage
Foundation Details Pilings
Water View Y/N Y
Lot Dimensions 50 x 100
Lot Size Acres 0.11
Lot Size Source Estimated
Waterfront Y/N N
Navigable Water Y/N N
Water Oriented Y/N N
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Internal Only
Street Number 1 16
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* Excluded Features
List By
Monument Sotheby's International Realty

Broker

kim@kimhamer.com

Email

Affordability Calculator

$33,571
Per Month
99%
1%
0%
Monthly Principal & Interest
$33,149
Monthly Property Taxes
$422
Monthly Home Insurance
--
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.
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Nearby
2314408 Elementary School
2314409 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
7/24/2026$5,250,000 Listed Price

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16 Chicago Street, Dewey Beach, DE, 19971 is a Single Family Home for sale at $5,250,000 with 4,500 sqft and a lot size of 0.11. 16 Chicago Street has 5 bedrooms, 4.2 baths, and was built in 2000. The property's zip code is 19971 which is in Dewey Beach, DE