16 Chicago Street, Dewey Beach, DE 19971 - Photo 1

1/1

$4,935,000

Sold
Closed
Single Family
5 Beds
4 Full Baths
2 Partial Baths
5,500 Sq. Ft.
2 Car Garage
Updated 7 days ago

1/1

Property Description

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 views-creating 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 backyard-ideal 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.

Full Property Details

Full Property Details for 16 Chicago St

General

Sold For: $4,935,000
Taxes: $5,068
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: DESU2116884
Added to Site: 92 day(s) ago

Interior

Rooms/Areas: 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
Interior Features: Pantry, Ceiling Fan(s), Elevator, Window Treatments
Fireplace: Yes
Number of Fireplaces: 2
Fireplace(s): Gas/Propane
Appliances: Dishwasher, Disposal, Dryer - Electric, Microwave, Oven/Range - Gas, Range Hood, Refrigerator, Washer
Furnished: Yes
Flooring: Carpet, Hardwood, Tile/Brick

Rooms

Bathrooms

Total Bathrooms: 6
Full Bathrooms: 4
Half Bathrooms: 2
Upper Floor Baths: 2
Upper - Full Baths: 1
Upper - 1/2 Baths: 1
Main Floor Baths: 4
Main - Full Baths: 3
Main - 1/2 Baths: 1

Bedrooms

Total Bedrooms: 5
Bedrooms Upper: 1
Bedrooms Main & Up: 4

Other Rooms

Laundry: Main Floor

Additional Information

Security/Safety: Monitored, Security System

Exterior

Exterior Features: Lawn Sprinkler, Outside Shower
Porch/Patio/Deck: Balcony, Deck(s)

Parking

Garage: Yes
Garage Spaces: 2
Total Spaces: 6
Parking Features: Crushed Stone
Parking Type: Off Street, Driveway, Attached Garage
Garage Description: Garage Door Opener

Location

Area: Lewes Rehoboth Hundred (31009)
County: SUSSEX
Subdivision: REHOBOTH BY THE SEA
Driving Directions: Ocean Block of Chicago Street in Rehoboth by the Sea in Dewey Beach
Location Details: Oceanblock
City Limits: Yes

School Information

School District: Cape Henlopen

Community

Pets Allowed: Yes
Pets: No Pet Restrictions

Heating & Cooling

Central air: Yes
Cooling Type: Central A/C, Zoned
Cooling Fuel: Electric
Heating Type: Forced Air, Heat Pump(s)
Heating Fuel: Propane - Leased
Water Heater: Propane

Utilities

Sewer: Public Sewer
Water: Public

Structural Information

Architectural Style: Coastal
Structure Type: Detached
Architect: Tony Beto
Builder: Dewson
Construction: Stick Built
Foundation: Pilings
Roof: Architectural Shingle
Walls/Ceilings: Vaulted Ceilings
Elevator(s ): 1
Stories Description: Main, Upper 1
Square Feet: 5,500
Sq. Ft. Source: Estimated
Living Area: 4,500 Sq. Ft.
Finished Above Grnd: 4,500 Sq. Ft.
Unfin. Above Grnd: 1,000 Sq. Ft.
Year Built: 2000
Year Built Source: Estimated
Property Condition: Excellent

Lot Features

Property View: Ocean
Lot Size (Acres): 0.11
Lot Size (Sq. Ft.): 5,000
Lot Size Source: Estimated
Lot Dimensions: 50 x 100
Zoning: RESIDENTIAL
Lot Description: Landscaping

Water Features

Water View: Yes

Financial Considerations

Price Per Sq. Ft.: $1,166.67
School Tax: $4,342
City/TownTax: $236
City/TownTax Freq: Annually
County Tax: $490
County Tax Freq: Annually
Tax Amount: $5,068
Terms: Standard Sale

Disclosures and Reports

Ownership: Fee Simple
Exclusions: Artwork, Decor, Dishes, Glassware, Utensils, Personal Items, Bikes, Beach Chairs.
Inclusions: Furniture, Televisions, Bedding

Listed by Monument Sotheby's International Realty, Kimberly Lear Hamer
Sold by Patterson-Schwartz-Rehoboth, JOSEPH LINGO

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Listing agent

— 16 Chicago St —

Kimberly Lear Hamer

Monument Sotheby's International Realty

Listing Office Email: justin.healy@msir.net

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NMLS#: 1598647

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Schools

Schools serving 16 Chicago St

School District:Cape Henlopen School District

Name	Grades	Distance
Rehoboth Elementary School 500 Stockley Street, Rehoboth Beach, DE 19971	PK-6	1 mi
Beacon Middle School 19483 John J Williams Highway, Lewes, DE 19958	4-8	4.1 mi
Cape Henlopen High School 1250 Kings Highway, Lewes, DE 19958	8-12	5.7 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 16 Chicago St

Date

Details

Price

Change

Source

9/10/2026

Sold

$4,935,000

-6%

MLS

7/24/2026

Listed

$5,250,000

—

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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Updated 4 days ago

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Total Baths
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Total Bath
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Sq. Ft.

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Updated 3 days ago

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Beds
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Sq. Ft.

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Active
Updated 2 days ago

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Total Bath
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Sq. Ft.

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Updated 2 days ago

3
Beds
4
Total Baths
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Sold

$4,510,000

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Single Family
Closed
Updated 10 days ago

9
Beds
10
Total Baths
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Sq. Ft.

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Sold

$4,700,000

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Closed

6
Beds
6
Total Baths
2,666
Sq. Ft.

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$4,511,500

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Closed
Updated 7 days ago

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Beds
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Total Baths
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Sq. Ft.

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Closed

4
Beds
5
Total Baths
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Sq. Ft.

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16 Chicago Street, Dewey Beach, DE 19971 (MLS# DESU2116884) is a Single Family property that was sold at $4,935,000 on September 10, 2026. Want to learn more about 16 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.

16 Chicago St Dewey Beach, DE 19971

Full Property Details for 16 Chicago St

General

Interior

Rooms

Bathrooms

Bedrooms

Other Rooms

Additional Information

Exterior

Parking

Location

School Information

Community

Heating & Cooling

Utilities

Structural Information

Lot Features

Water Features

Financial Considerations

Disclosures and Reports

Listing agent

Get Pre-Approved Today

Be ready to buy your new home!

Be ready to buy your new home!

Schools serving 16 Chicago St

Price & Sales History for 16 Chicago St

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