Homes for sale - 2 CHICAGO ST, Dewey Beach, DE 19971

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Jon Tripp

info@jontripp.com +1(703) 864-9652

Listed by SHAUN TULL • Jack Lingo - Rehoboth

$ 5,400,000

Est. payment | -/mo

6 Beds

6 Baths

2,666 SqFt

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$ 5,400,000

Est. payment | -/mo

Save Virtual Tour

6 Beds

6 Baths

2,666 SqFt

Key Details

Property Type Single Family Home

Sub Type Detached

Listing Status Coming Soon

Purchase Type For Sale

Square Footage 2,666 sqft

Price per Sqft $2,025

Subdivision Rehoboth By The Sea

MLS Listing ID DESU2077352

Style Coastal,Contemporary

Bedrooms 6

Full Baths 5

Half Baths 1

HOA Y/N N

Abv Grd Liv Area 2,666

Year Built 1988

Available Date 2025-09-26

Annual Tax Amount $6,705

Tax Year 2025

Lot Size 5,000 Sqft

Acres 0.11

Lot Dimensions 50 x 100

Property Sub-Type Detached

Source BRIGHT

Property Description

Rare oceanfront opportunity in Rehoboth by the Sea. Discover unparalleled coastal living at 2 Chicago Street, an oceanfront retreat in the highly coveted community of Rehoboth by the Sea on the north end of Dewey Beach. This exceptional 6-bedroom, 5.5-bath home offers sweeping panoramic views from nearly every room, with a private dune crossover that leads directly to the wide, sandy beach. The first level welcomes you with a bright entry foyer, two bedrooms (including a flexible oceanfront space ideal for a den, exercise room, or guest suite), two full baths, and a convenient laundry room. Upstairs, the recently updated kitchen shines with quartz counters, stainless steel appliances, and custom cabinetry, seamlessly flowing into the dining and living areas—all framed by walls of windows showcasing endless ocean vistas. Step outside to the expansive oceanfront deck, perfect for sunrises, gatherings, and salty breezes. A private office with sweeping north-facing views completes this level. On the third floor, you'll find four additional bedrooms and three full baths, including the oceanfront primary suite with its own balcony for uninterrupted sunrise views. The rooftop deck crowns the home, offering a bird's-eye view of the coastline—an unforgettable setting for stargazing or enjoying fireworks on July 4th. Rehoboth by the Sea is one of the Delaware coast's most sought-after neighborhoods, known for its wide beaches, relaxed atmosphere, and close proximity to both Rehoboth and Dewey Beach attractions. Currently, 2 Chicago Street stands as the only oceanfront property available in either community—making this a truly rare opportunity to own a piece of coastal paradise.

Location

State DE

County Sussex

Area Lewes Rehoboth Hundred (31009)

Zoning TN

Direction North

Rooms

Main Level Bedrooms 2

Interior

Interior Features Ceiling Fan(s), Window Treatments, Combination Kitchen/Dining, Primary Bedroom - Ocean Front, Upgraded Countertops, Wood Floors

Hot Water Electric

Heating Heat Pump(s)

Cooling Central A/C, Zoned

Flooring Ceramic Tile, Wood

Fireplaces Number 1

Inclusions Some furnishings

Equipment Exhaust Fan, Range Hood, Oven/Range - Electric, Dishwasher, Disposal, Dryer, Microwave, Washer, Refrigerator, Icemaker

Fireplace Y

Window Features Bay/Bow,Double Hung

Appliance Exhaust Fan, Range Hood, Oven/Range - Electric, Dishwasher, Disposal, Dryer, Microwave, Washer, Refrigerator, Icemaker

Heat Source Electric

Laundry Lower Floor

Exterior

Exterior Feature Deck(s), Porch(es), Balcony, Roof

Garage Spaces 3.0

Utilities Available Cable TV, Sewer Available, Water Available

Waterfront Description Sandy Beach

Water Access Y

Water Access Desc Public Beach

View Ocean, Panoramic

Roof Type Metal

Accessibility None

Porch Deck(s), Porch(es), Balcony, Roof

Road Frontage City/County

Total Parking Spaces 3

Garage N

Building

Lot Description Corner, Premium

Story 3

Foundation Slab

Sewer Public Sewer

Water Public

Architectural Style Coastal, Contemporary

Level or Stories 3

Additional Building Above Grade, Below Grade

Structure Type Dry Wall

New Construction N

Schools

School District Cape Henlopen

Others

Pets Allowed Y

Senior Community No

Tax ID 334-20.14-156.00

Ownership Fee Simple

SqFt Source 2666

Security Features Smoke Detector

Acceptable Financing Cash, Conventional

Listing Terms Cash, Conventional

Financing Cash,Conventional

Special Listing Condition Standard

Pets Allowed No Pet Restrictions

Virtual Tour https://www.dropbox.com/scl/fi/ccb02ii1w23mbpgn8mzfe/2_chicago_st_dewey_beach-1080p.mp4?rlkey=58nk46dooidffapkinoi5yp2l&dl=0

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Jon Tripp

REALTOR® | Lic# 225229424

info@jontripp.com

+1(703) 864-9652

1320 Central Park Blvd Suite 200, Fredericksburg, VA, 22401, USA

2 CHICAGO ST Dewey Beach, DE 19971

Jon Tripp

Key Details

Location

Rooms

Interior

Exterior

Building

Schools

Others

2 CHICAGO ST