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$5,250,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 2 Partial Baths
  • 5,500 Sq. Ft.
  • 2 Car Garage
  • Updated 1 hour ago
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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 of 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 for 16 Chicago St

General

  • Price: $5,250,000
  • Taxes: $5,068
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: DESU2116884
  • Updated: 7/25/2026
  • Added to Site: 1 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

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

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Listing agent

— 16 Chicago St —

  • Kimberly Lear Hamer

    Monument Sotheby's International Realty

Listing Office Email: justin.healy@msir.net

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 16 Chicago St

School District:Cape Henlopen School District
NameGradesDistance
Rehoboth Elementary School
500 Stockley Street, Rehoboth Beach, DE 19971
PK-61 mi
Beacon Middle School
19483 John J Williams Highway, Lewes, DE 19958
4-84.1 mi
Cape Henlopen High School
1250 Kings Highway, Lewes, DE 19958
8-125.7 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/24/2026
Listed
$5,250,000
1120.93%
MLS
2/16/2007
Sold
$430,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 16 Chicago St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,151
60%
$58,900
—
2023
$3,219
3%
$58,900
—
2022
$3,118
1%
$58,900
—
2021
$3,092
—
$58,900
—
2020
$3,083
1%
$58,900
—
2019
$3,065
18%
$58,900
—
2018
$2,587
4%
$58,900
—
2017
$2,477
4%
$58,900
—
2016
$2,388
5%
$58,900
—
2015
$2,284
1%
$58,900
—
2014
$2,267
3%
$58,900
—
2013
$2,204
—
$58,900
—
View All
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 for 16 Chicago St

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Listed by Monument Sotheby's International Realty, Kimberly Lear Hamer

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16 Chicago Street, Dewey Beach, DE 19971 (MLS# DESU2116884) is a Single Family property with 5 bedrooms, 4 full bathrooms and 2 partial bathrooms. 16 Chicago Street is currently listed for $5,250,000 and was received on July 24, 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.

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