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$4,400,000
7 Beds ⋅ 7 Baths
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.

105 Chicago St, Dewey Beach

Listing courtesy of Mann & Sons, Inc.. Contact: (302) 227-9477
$4,700,000
5 Beds ⋅ 6 Baths
Rare North End Ocean-View Retreat | 5BR Luxury Home with Pool, Elevator, Garage & Off Street Parking Welcome to one of the most exceptional offerings on the north end of Dewey Beach, where modern coastal luxury meets a truly rare combination of ocean views, iconic and one-of-a-kind sightlines down the Dewey strip, and the convenience of paved off-street parking spaces. This newly constructed, fully furnished 5-bedroom, 4 full bathroom (and 2 half bath), 4,155 square-foot residence is thoughtfully designed across three expansive levels, all easily accessed by a private elevator. From the moment you arrive, the home sets itself apart with its scale, craftsmanship, and turnkey convenience. The heart of the home is an open-concept living space designed to maximize natural light and capture sweeping views. Expansive windows and multiple outdoor decks create a seamless indoor-outdoor experience, while high-end finishes and curated furnishings elevate every detail. Step outside to your private pool and custom-built pool bar, complete with dedicated seating and service area, creating the ultimate setting for entertaining. Whether hosting summer gatherings or unwinding after a day at the beach, this outdoor space delivers a true resort-style experience rarely found in Dewey Beach. What truly distinguishes this property is its unique vantage point. Enjoy not only ocean views, but a rare, unobstructed perspective down the Dewey Beach strip, an irreplaceable feature that delivers both energy and exclusivity. Combined with the quiet appeal of the north end location, this home also offers easy access to the town. Additional highlights include: • Five spacious bedrooms ideal for hosting large groups • Private elevator servicing all three floors • Multiple decks capturing ocean breezes and panoramic views • Off-street parking spaces, an exceptional amenity in Dewey Beach • Private garage offering additional storage and convenience • Fully furnished and professionally designed for a true turnkey experience Whether you’re seeking a premier personal retreat or property to lease, this home offers outstanding leasing potential while delivering a luxury lifestyle that is simply unmatched in Dewey Beach. This is a rare opportunity to own a standout property in one of the East Coast’s great beach communities, where location, views, and livability converge.

24 Houston St, Rehoboth Beach

Listing courtesy of Houwzer. Contact: 2677652080