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$4,935,000
5 Beds ⋅ 6 Baths
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.

16 Chicago St, Dewey Beach

Listing courtesy of Monument Sotheby's International Realty. Contact:

Selling Office: Patterson-Schwartz-Rehoboth.

$4,700,000
6 Beds ⋅ 6 Baths
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.

2 Chicago St, Dewey Beach

Listing courtesy of Jack Lingo - Rehoboth. Contact:

Selling Office: Monument Sotheby's International Realty.

$2,500,000
3 Beds ⋅ 2 Baths
Imagine stepping back into the golden era of beach living at 124 Jersey Street—an exceptionally rare Fee Simple opportunity in Rehoboth by the Sea just two blocks from the ocean. Originally built as a quintessential North Dewey beach retreat, this classic 3-bedroom, 2-bath Windjammer cottage has been thoughtfully improved while preserving its authentic coastal character. In 2021, the property underwent significant structural enhancements, including lifting of the home by East Coast Structural to allow for the addition of a full foundation and insulated crawlspace. Major infrastructure improvements were completed at that time, including new plumbing, updated electrical systems, ductless mini-split HVAC, new siding and upgraded insulation—capital improvements that provide both peace of mind and long-term durability. The home is further complemented by its distinctive and durable red metal roof, adding both architectural charm and practical longevity to this timeless coastal property. Inside, the home features an inviting, airy layout designed for relaxed coastal living, with numerous gathering spaces ideal for entertaining after a day on the beach. The kitchen has been updated with new appliances and countertops, while outdoor spaces include spacious decking, dramatic lighting, lush landscaping, and multiple entertaining areas perfect for summer evenings, morning coffee, or casual gatherings with friends and family. In a community largely comprised of land lease properties, fee-simple opportunities within Rehoboth by the Sea are limited and rarely available, providing long-term security, flexibility, and freedom from annual ground rent. Ideally located just steps from the beach and Dewey Beach’s vibrant dining, nightlife, and coastal attractions. Take a walk to local favorites like the Starboard, Bottle & Cork, or Woody’s for their famous crabcakes. Downtown Rehoboth’s boutique shopping and award-winning restaurants—including Back Porch Café, Fable, and Henlopen Oyster House—are just a mile away. Park the car, hop on a bike, or catch the Jolly Trolley and enjoy the best of coastal living. Whether enjoyed as a nostalgic personal retreat, income-producing rental, or strategic long-term investment, the property offers compelling future potential in one of coastal Delaware’s most sought-after beach communities.

124 Jersey St, Dewey Beach

Listing courtesy of Monument Sotheby's International Realty. Contact:

Selling Office: Jack Lingo - Rehoboth.

$2,075,000
5 Beds ⋅ 4 Baths
Dewey Beach, single family (fee simple) dream home! Enjoy shimmering bay views and golden sunsets from your 48 X 50 rooftop deck overlooking the Dewey Beach skyline! Perfect investment opportunity! The rooftop deck and ample parking for eight creates an excellent Dewey rental investment. This charming 5 bedrooms and three and a half baths, 2,600 sq' home will surely wow you the moment you step in the door. Let's take a walk through this gem of a home! As you enter the first floor through the double French doors, you'll be instantly overwhelmed by the huge 21' X 32' bonus room with an additional set of doors leading you to the rear of the yard. There's no need to worry about sandy toes as the entire first floor features durable 12" ceramic tile. Bedroom #1 is a large 12' X 20' with recessed lighting, built-in shelving & custom paint color. French doors provide private entry/exit to the 10' X 50' concrete patio made private by the banana palm grove, pampas grasses & fencing surrounding half of it. A large bathroom with shower & another entrance leading to an outside shower stall & separate shed round out this floor along with two large closets & a mechanical room. With a grand first impression of the second floor, the 10' ceilings and open floor plan create a stately appearance. Step through the double sliding french doors in the main living space to a huge 10' X 50' covered front porch with wainscot ceiling, 2 ceiling fans & recessed lighting spanning the entire width of the home. This is a premier location for post-beach happy hours, rainy day activities, & people-watching. The living room has hardwood floors, custom colors, ceiling fans, recessed lighting, crown molding, & a propane gas fireplace for those chilly off-season nights! Also located on this floor is the kitchen which features 12" ceramic tile flooring, granite counters, peninsula bar with seating for 4, & 3 copper hanging+ light pendants. There is a gas stove/oven, custom cherry cabinetry, ceiling fan, crown molding & wine fridge under the bar. A guest powder room is on this level as well. The spacious owners' suite is 20' X 27' with hardwood floors, walk-in closet, lighted ceiling fan, custom colors, 9' paneled doors, & crown molding. French doors also provide private access to the front porch. The owners' suite full bath includes ceramic tile floors & a large walk-in shower with two heads & glass doors. There's a pedestal sink, a custom built-in cabinet, & a clawfoot soaking tub to melt your worries away! The third floor consists of bedrooms 3 (15 X 21), 4 (19' X 18'), & 5 (19' X 18'). All are spacious & carpeted with custom painting & ceiling fans with light kits. A full bath with linen closet & a separate laundry closet are also on this floor. The versatile 12' X 29' open space can be utilized for recreation, as an office or an additional sleeping area. This bonus area has built-in cabinetry, hardwood flooring, and a ceiling fan. A full-paned door grants access to the 6' X 22' deck & spiral staircase leading to the roof top deck and that's where the fun begins!. Sit back, relax with a cocktail, & enjoy the sunset behind the iconic Dewey Beach water tower. It's like being on top of the world! This home has never been a rental and is being offered tastefully furnished, turn key ready. Please call to schedule a private showing of this unique bay block home!

107 Swedes St, Dewey Beach

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: BAY COAST REALTY.

$2,075,000
4 Beds ⋅ 4 Baths
Experience the charm of a quintessential beach cottage ideally located just one block from the ocean in the heart of Dewey Beach. Perfectly positioned between downtown Rehoboth Beach and Dewey Beach, you’ll enjoy effortless access to award-winning restaurants, vibrant nightlife, boutique shopping, and local amenities. For added convenience, the Jolly Trolley stop is just steps away, making it easy to explore the area without ever moving your car. Inside, vaulted, beamed ceilings create a warm and inviting coastal atmosphere filled with natural light, character and charm. Rich hardwood floors flow throughout the home, enhancing its timeless appeal. The spacious kitchen serves as the heart of the cottage, anchored by a large central island that’s perfect for entertaining, gathering with friends, or simply relaxing after a day at the beach. The home features four spacious bedrooms, including two with ensuite baths, offering comfort and privacy for family and guests alike. A large sun deck is a true beach house must — perfect for sunning and enjoying the outdoors while listening to the sound of crashing waves in the distance. The fenced yard adds an extra sense of privacy and comfort, while the turf and surrounding pavers provide attractive, easy maintenance living. With 51 years remaining on this unique land lease property, this exceptional cottage is a must-see for Dewey Beach lovers seeking the perfect blend of coastal charm, convenience, and lifestyle.

103 Carolina St, Dewey Beach

Listing courtesy of Jack Lingo - Rehoboth. Contact:

Selling Office: Monument Sotheby's International Realty.

$1,773,000
3 Beds ⋅ 2 Baths
Imagine stepping back into the golden era of beach living at 115 Jersey Street—a classic coastal retreat in much sought-after Rehoboth by the Sea, just over one block from the ocean. A quintessential North Dewey beach cottage, this charming 3-bedroom, 2-bath home blends nostalgic beach character with thoughtful updates designed for today’s coastal lifestyle. The property has undergone numerous renovations over the years, highlighted by a spacious updated kitchen that serves as the heart of the home—perfect for gathering after a day at the beach. Inside, the home offers an inviting and airy layout with comfortable gathering spaces ideal for relaxed entertaining. Outdoor living takes center stage with an expansive rear deck overlooking a generously sized backyard with ample room for a pool, creating exceptional potential for enhancing both lifestyle, rental revenue and long-term value. Lush landscaping and multiple outdoor entertainment areas provide the perfect backdrop for summer evenings, morning coffee, or casual gatherings with friends and family. Located within the desirable Rehoboth by the Sea, the property is situated on leased land with approximately 48 years remaining on the current land lease—offering an opportunity to enjoy beach living in one of coastal Delaware’s most coveted communities at a more approachable price point than nearby fee simple properties. The property has also proven itself as a strong income-producing investment, with over $68,000 in booked rental reservations for the 2026 season already on the calendar, highlighting both its desirability and exceptional rental potential. Ideally positioned just steps from the beach and Dewey Beach’s vibrant dining, nightlife, and coastal attractions, enjoy easy access to local favorites like The Starboard, Bottle & Cork, and Woody's Dewey Beach for their famous crab cakes. Downtown Rehoboth Beach, with its boutique shopping and acclaimed dining destinations including Back Porch Café, Fable, and Henlopen City Oyster House, is just a mile away. Park the car, hop on a bike, or catch the Jolly Trolley and enjoy the very best of coastal living. Whether enjoyed as a nostalgic personal getaway, rock solid rental investment, or long-term beach retreat, 115 Jersey Street offers a rare opportunity to own a piece of classic Dewey Beach charm in an exceptional location.

115 Jersey St, Dewey Beach

Listing courtesy of Monument Sotheby's International Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$1,500,000
3 Beds ⋅ 2 Baths
Oceanfront living in the heart of Dewey Beach. Welcome to 4 Sea Strand, Unit 19, a rare opportunity to own a true coastal retreat just steps from the sand and surf. Perfectly positioned oceanfront, this residence delivers front-row access to sunrise views, salty breezes, and the unmistakable rhythm of beach life. Thoughtfully updated with a bright, beach-inspired interior, the home blends classic coastal charm with modern comfort. Wide plank wood floors, crisp shiplap walls, an open-concept kitchen and living area, and abundant natural light create an easy, inviting atmosphere ideal for relaxing after long beach days. Step outside and you’re moments from the shoreline—no streets to cross, just pure oceanfront living. Beyond the beach, enjoy walking distance to the Rehoboth Beach Boardwalk, along with Dewey’s renowned restaurants, nightlife, and boutique shopping. From morning coffee by the ocean to sunset strolls, live music, and bay sunsets, this location puts the very best of Dewey and Rehoboth Beach at your fingertips. Whether you’re seeking a personal beach getaway, a strong rental investment, or a legacy coastal property, 4 Sea Strand, Unit 19 offers an unbeatable combination of location, lifestyle, and classic Delaware beach appeal. Opportunities like this—true oceanfront in Dewey Beach—are few and far between.

4 Seastrand Court, Unit 19, Dewey Beach

Listing courtesy of REHOBOTH BAY REALTY, CO.. Contact:

Selling Office: Unrepresented.

$1,335,000
4 Beds ⋅ 2 Baths
Just Two Blocks from the Beach on a Fee Simple Lot – Stylishly Updated 4-Bedroom Ranch Welcome to this beautifully maintained 4-bedroom, 2-bath ranch-style home, ideally situated just two blocks from the beach. Whether you're seeking a serene getaway or a full-time residence, this thoughtfully updated home delivers comfort, style, and coastal charm. Remodeled about 10 years ago, the home showcases quality finishes throughout, including rich hickory and walnut hardwood flooring, Carrara marble in the bathrooms, and solid interior doors. The custom-designed kitchen is a true standout, featuring striking concrete countertops and ample storage—perfect for entertaining or everyday living. Additional highlights include a versatile bonus room, ideal for a home office or guest space. The HVAC systems were updated approximately two years ago, and the architectural shingle roof offers lasting durability, installed about 15 years ago, all situated on a conditioned crawl space Don’t miss this opportunity to own a move-in-ready beachside retreat with timeless upgrades and a location that can’t be beat!

1602 Bayard Ave, Dewey Beach

Listing courtesy of Investors Realty, Inc.. Contact:

Selling Office: Jack Lingo - Rehoboth.