Cape Henlopen Homes under $500,000

Cape Henlopen Homes under $500,000

Welcome to the picturesque Cape Henlopen School District, nestled in the heart of Sussex County, Delaware. This vibrant community is not only known for its stunning coastal views and rich history but also for its commitment to providing an exceptional education for its students. The Cape Henlopen School District serves families in the charming towns of Lewes, Rehoboth Beach, and nearby areas, ensuring that children receive a well-rounded education in a supportive environment.

Families residing in this district benefit from a range of educational opportunities, including innovative programs, dedicated teachers, and state-of-the-art facilities. The district prides itself on fostering creativity and critical thinking, equipping students with the skills they need to succeed in an ever-changing world. With a focus on academic achievement, arts, and athletics, Cape Henlopen Schools are designed to nurture the whole child.

For those looking to call this beautiful region home, you’ll be pleased to know that there are a variety of homes available for under $500,000. Whether you’re seeking a cozy beach cottage, a charming single-family home, or a modern townhouse, the Cape Henlopen area offers an array of options that cater to different lifestyles and budgets. Imagine waking up to the sound of the ocean and enjoying a vibrant community filled with parks, shops, and dining options just a stone's throw away.

Cape Henlopen is not just a place to live; it’s a lifestyle filled with opportunities for growth and connection. Discover your dream home in this delightful district today!

Newest Cape Henlopen Homes under $500,000

22836 Angola Rd W, Lewes
$369,000
2 Beds ⋅ 2 Baths
REFRESHED & READY FOR ITS NEXT CHAPTER — OFFERED AT $369,000! Discover an incredible opportunity to own a spacious, well-built ranch home in the highly desirable gated waterfront community of Angola by the Bay! At this attractive price point, this home offers an excellent opportunity to finally enjoy all that this sought-after community has to offer without taking on an extensive list of renovation projects. Freshly refreshed and showing better than ever, this charming two-bedroom, two-bath home offers approximately 1,200 square feet of comfortable, single-level living with an open, inviting floor plan, generously sized bedrooms, a spacious living room, and a wonderful foundation for adding your own personal touches. Solidly constructed and well insulated, this home offers a comfortable and peaceful interior, central air conditioning, and a practical layout with room to make it your own. A spacious attic with pull-down stairs provides an abundance of additional storage space. The three-season porch overlooking the fenced backyard offers a wonderful place to relax, entertain, or simply enjoy the coastal surroundings. Situated on a 75 x 100 lot the property offers convenient access to the pool and the pickleball courts, common areas, wooded trails, that to the appeal. The bonus is the lifestyle that comes with living in Angola by the Bay! This established gated waterfront community offers access to Rehoboth Bay through its private marina and boat ramp, along with fishing and crabbing piers, kayak launches, approximately eight miles of scenic walking trails, and beautiful community green spaces. Enjoy the saltwater swimming pool, clubhouse, tennis and pickleball courts, basketball courts, playgrounds, and an impressive variety of clubs, social groups, and year-round activities. The community also benefits from an on-site office and maintenance staff. Conveniently located just a few miles from the beautiful beaches of Lewes and Rehoboth, shopping, dining, schools, and Delaware's scenic state parks, Angola by the Bay offers the perfect combination of a relaxed coastal setting and easy access to everything the area has to offer. At just $369,000, this is a fantastic opportunity to enjoy the Angola by the Bay lifestyle! Whether you're looking for a year-round residence or a coastal getaway, this property deserves a look!

22836 Angola Rd W, Lewes

Listing courtesy of Tesla Realty Group, LLC. Contact:

24363 Hollyville Rd, Millsboro
$179,990
3 Beds ⋅ 1 Baths
13mi to DOWNTOWN LEWES + REHOBOTH BEACH -- INVESTOR ALERT -- Needs work, but huge potential for this 3BR cottage on a nice-sized lot in the Cape Henlopen School District. Newer well and 2-tier septic system should help knock out two of the bigger-ticket items. Getting to the beach, or anywhere you want to go, will be a breeze -- easy access to all the major routes and the bypass. 13-14 mi to the beloved Delaware Beaches of Rehoboth, Dewey, Lewes - each boasting its own unique charm and amenities - from world-class dining to watersports. A paradise for nature lovers, sports enthusiasts, and anyone looking for adventure - boating, fishing, crabbing, exploring state parks, lush local history, arts and culture, unique boutique shopping, and don't forget golf - the list goes on! Miles of ocean beaches, tidal bays, rivers, and woodlands to be enjoyed. Sizes, taxes, distances approximate.

24363 Hollyville Rd, Millsboro

Listing courtesy of EXP Realty, LLC. Contact:

35669 Buttermilk Dr, Rehoboth Beach
$250,000
2 Beds ⋅ 2 Baths
COMING SOON!!! East of Route 1 Buying Opportunity! Welcome to this beautiful coastal home offering bright, airy living just 4 miles from the famous downtown Rehoboth Beach & Boardwalk. The open-concept design flows seamlessly from the sunlit living room into a fully equipped kitchen featuring granite countertops and a deluxe LG stainless steel appliance package. Skylights, vaulted ceilings, crown molding, and vibrant accent colors enhance the home's coastal charm, while durable laminate and plank-style ceramic tile run throughout. A stunning sunroom with a wood-plank ceiling leads to a fully fenced backyard complete with an outdoor patio and storage shed. Sunroom could act as a bonus room for guests & family! The primary bedroom boasts a custom walk-in closet system and private bath, accompanied by a well-appointed second bedroom and full hall bath. Additional conveniences include an in-unit stacked washer/dryer with shelving. Situated near the Junction & Breakwater trail, lot rent covers seasonal lawn care, trash service, and access to the community pool, clubhouse, and fitness center. Park application approval required; specialized financing options available.

35669 Buttermilk Dr, Rehoboth Beach

Listing courtesy of Coldwell Banker Realty. Contact:

30256 Green Valley Run, Milton
$432,000
3 Beds ⋅ 2 Baths
EFFORTLESS OVERBROOK SHORES LIVING! Nestled on a spacious almost half-acre lot in the established waterfront community of Overbrook Shores in Milton, this inviting home is a beautifully kept 3-bedroom, 2-bath rancher offering 1,804 square feet of single-level living space. This move-in-ready home seamlessly combines privacy, charm, and top-tier capital upgrades. Step inside to find gleaming hardwood flooring flowing throughout. The smart split-bedroom layout positions the private Primary Suite, complete with a walk-in closet and an updated en-suite primary bath, on one side of the home, while two comfortable guest bedrooms and a secondary full bath rest on the opposite wing. A functional kitchen with abundant cabinetry and an adjacent laundry room with pantry storage round out the well-designed floor plan. Outdoor entertaining is effortless with your choice of a rear deck or custom paver patio overlooking the lush backyard. Storage is never an issue thanks to the attached 2-car garage and a 12X18 detached shed equipped with electric power. Complete with a sealed driveway, HVAC system (replaced in 2023), sliding glass door (2022), water heater (2020), and an updated roof and skylight replacement (2018), every major component has been meticulously maintained. Located just minutes from historic downtown Milton, route 1 shopping & dining and the beach, this property is a true standout! Call and schedule a showing today!

30256 Green Valley Run, Milton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

35091 North Dr, Lewes
$175,000
2 Beds ⋅ 1 Baths
Nestled in a serene waterfront community, this exquisite manufactured home offers a harmonious blend of modern luxury and comfort, perfect for those seeking an exclusive lifestyle. Built in 2025, this modular masterpiece showcases innovative design and high-end finishes that elevate everyday living. Step inside to discover a thoughtfully designed interior that radiates warmth and sophistication. The open-concept layout seamlessly integrates the kitchen and dining areas, creating an inviting space for both casual meals and elegant entertaining. appliances, including a built-in microwave, single oven, and stove, ensuring culinary adventures are met with ease and style. The refrigerator provides ample storage for all your gourmet ingredients, while the water heater guarantees comfort and convenience. The home has 2 bedrooms, including an entry-level bedroom that offers flexibility for guests or a private office. The bathroom is a true retreat, boasting a luxurious walk-in shower that invites relaxation after a long day. Ceiling fans throughout the home enhance airflow and comfort, making every corner feel just right. Double deck will have the lower deck screened in and enjoy the fresh air on the upper deck with full 360 views. Outside, the allure continues with access to the community pool, perfect for sun-soaked afternoons and social gatherings. The property boasts an impressive 37 feet of waterfrontage along the bay, providing breathtaking views and a tranquil atmosphere. Enjoy the soothing sounds of water and the beauty of nature right at your doorstep, with navigable waters inviting you to explore the bay's hidden gems. This home is not just a residence; it's a lifestyle. With low VOC insulation and sustainable construction materials, you can enjoy peace of mind knowing that your living space is both eco-friendly and luxurious. The community offers a unique blend of privacy and camaraderie, making it an ideal setting for those who appreciate the finer things in life. Experience the perfect balance of comfort, elegance, and waterfront living in this stunning property. Whether you're hosting friends or enjoying a quiet evening by the water, this home is designed to cater to your every need, making it a true sanctuary for the discerning homeowner. This home aslo has a rooftop deck.

35091 North Dr, Lewes

Listing courtesy of Investors Realty, Inc.. Contact:

no property photo
$439,999
3 Beds ⋅ 2 Baths
Tucked away in the desirable community of Starlight Meadows, this 3-bedroom, 2-bath ranch offers the convenience of single-level living, a spacious layout, and NO HOA! With limited turnover in the community, opportunities to call Starlight Meadows home don't come along often. Offering just under 2,000 square feet, this home is situated on a .29-acre lot backing to trees and positioned on a cul-de-sac. Inside, you'll appreciate the open floor plan featuring a generously sized living room that flows into the kitchen and dining area. All three bedrooms are comfortably sized, including the primary suite with its own private bath. The thoughtful layout keeps all bedrooms and bathrooms on one side of the home, separate from the main living areas. An oversized two-car garage provides plenty of room for parking and storage. Conveniently located near Route 1, this property is just a short drive to historic downtown Milton, the Delaware Bay beaches, and all the shopping, dining, and entertainment that Lewes and Rehoboth Beach have to offer. Enjoy the convenience of coastal Delaware while being tucked away from the hustle and bustle! Property is currently winterized.

7 Comet Ct, Milton

Listing courtesy of Keller Williams Realty. Contact:

1 Read Ave Unit 116D, Dewey Beach
$65,000
1 Beds ⋅ 1 Baths
UNMATCHED OPPORTUNITY! OCEANFRONT OWNERSHIP + RENTAL INCOME OPPORTUNITY! Imagine waking up to the sound of waves, stepping outside, and walking directly onto the sand. Enjoy morning strolls along the shoreline, afternoons soaking up the sun, and evening walks under glowing sunsets — all without having to drive anywhere or fight for parking. Welcome to The Surf Club, where OCEANFRONT LIVING MEETS FLEXIBILITY, INCOME POTENTIAL, AND HASSLE-FREE OWNERSHIP — and all without spending millions of dollars. This beautifully maintained 1-BEDROOM, 1-BATH CONDO comfortably SLEEPS FIVE thanks to a KING-SIZED BED, a QUEEN-SIZED SLEEPER SOFA, and a VERSATILE SLEEPING BENCH — making it perfect for families, guests, or maximizing rental potential. You'll enjoy 13 WEEKS OF DEEDED OWNERSHIP each year — this is NOT A TIMESHARE! FLEXIBLE RENTAL PROGRAM: At the beginning of each year, owners choose which weeks to USE and which to RENT. Any weeks placed into the SOV RENTAL POOL earn income based on the total rentals for your room category that week. If you’re the only owner renting, you keep 100% OF YOUR UNIT’S PROFITS. If multiple SOV units are rented, profits are divided equally among those owners. Nightly rental rates are market-driven, and on-site professional management — the same team that operates the HYATT at the Rusty Rudder — handles bookings, cleanings, maintenance, utilities, taxes, and insurance. You can also switch plans last minute: if you originally planned to use your week but can’t, you can make it available for rental. Likewise, if you planned to rent but decide you want to come, you can — as long as your unit or another available SOV is open. With SUMMER WEEKS TYPICALLY BOOKED, this property offers a RARE OPPORTUNITY to enjoy GUARANTEED VACATION TIME and PASSIVE INCOME — without the stress of managing a rental. Spend your mornings sipping coffee with a view, your afternoons on the sand, and your evenings strolling to Dewey’s best restaurants, live music, and nightlife — all just steps away. And when you want to explore, hop on the Jolly Trolley for a quick ride into Rehoboth. This isn’t just oceanfront ownership — it’s the ultimate Delaware beach lifestyle combined with a smart investment opportunity. With its prime SOV location, sleeping capacity for five, flexible rental income, and professional management, this condo delivers the best of both worlds. All of this can be yours for the price of a car!

1 Read Ave Unit 116D, Dewey Beach

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

26736 Northstar Dr, Ellendale
$474,990
4 Beds ⋅ 3 Baths
Welcome to the Caspian, a beautifully designed home that blends an open-concept layout with charming Loft-inspired elements. Offering 4 bedrooms, 2.5 baths, and a 2-car garage, this home provides the perfect balance of comfort, style, and functionality. The heart of the home features an open-concept kitchen, great room, and dining area—ideal for entertaining and everyday living. A walk-in pantry adds extra storage and convenience to the thoughtfully designed kitchen space. The tranquil primary suite serves as a private retreat, complete with a gorgeous bath and walk-in closet. Additional bedrooms are thoughtfully secluded for privacy, along with a dedicated home office perfect for working from home or creating a flexible living space. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. This community has a pool, clubhouse, pickleball courts, and more already built and ready for use!

26736 Northstar Dr, Ellendale

Listing courtesy of Delaware Homes Inc. Contact:

18480 Carters Grove Cir Unit 1, Lewes
$325,000
2 Beds ⋅ 2 Baths
Welcome to this inviting ground-level 2-bedroom, 2-bathroom condo, offering the perfect blend of indoor comfort and outdoor living! The spacious wraparound screened porch creates a wonderful natural setting, with sliding glass doors that open the living space to the outdoors. The primary suite features a private bath, walk-in closet, and direct access to the screened porch, while the secondary bedroom offers its own private covered patio. Inside, enjoy an upgraded kitchen with stylish countertops and a separate formal dining area. An exterior storage closet provides convenient space for beach chairs, bikes, and all your coastal essentials. With short-term rentals allowed, this property is an excellent opportunity for a beach getaway, investment property, or year-round home. Ideally located near both Rehoboth and Lewes beaches, shopping, dining, and other local amenities, the community also features the Dave Marshall Tennis & Pickleball Club, with memberships available. Enjoy the best of coastal Delaware living in a location that makes it easy to relax, explore, and enjoy everything the area has to offer!

18480 Carters Grove Cir Unit 1, Lewes

Listing courtesy of Jack Lingo - Lewes. Contact:

22794 Dogwood Dr, Lewes
$475,000
3 Beds ⋅ 3 Baths
Welcome to Angola by the Bay, one of Lewes' established gated waterfront communities offering an abundance of recreational amenities! This charming 3-bedroom, 2.5-bath home dubbed "The Beach Bird" features a spacious and versatile floor plan, ideal for a primary residence or coastal retreat. Upon entering, you're greeted by a bright and inviting sunroom offering additional dining and sitting space. French doors lead into the main living area, featuring a comfortable family room, dining area, and kitchen with convenient access to laundry. The main level also includes two bedrooms and two full bathrooms, one of which is an ensuite, while the additional bathroom features a jetted soaking tub. Upstairs, you'll find an expansive loft providing a second living area with endless possibilities for entertaining, recreation, or relaxing. An adjoining elevated deck extends the living space outdoors, while a third bedroom and half bath complete the second floor. Enjoy all that Angola by the Bay has to offer, including a community swimming pool, clubhouse, tennis and basketball courts, playground, marina, and water access for boating, kayaking, and fishing. Conveniently situated within walking distance of the pool and clubhouse and a short bike ride to the marina. Just a short drive to the beaches, shopping, and dining of Lewes and Rehoboth Beach. The seller has previously utilized the property as a short-term rental through Airbnb, with rental financials available upon request.

22794 Dogwood Dr, Lewes

Listing courtesy of Keller Williams Realty. Contact:

18877 Bent Anchor Ct Unit 3104, Rehoboth Beach
$399,900
3 Beds ⋅ 2 Baths
Welcome to Woods Cove! Enjoy low maintenance living while being minutes from the Beaches, 🏖️the Bay, 🌊 dining & shopping! Must see this beautiful well maintained 3 bdrm, 2 bath condo with an inviting open floor plan and a desirable split bedroom layout that offers added privacy for owners and guests. The 2 story foyer has ceramic tiled flooring and a large closet, an interior entry to the garage w/storage & electric. The beautiful atrium window welcomes the natural sunlight to shine through the living space. ☀️ The spacious Great room (living rm & dining rm) features hardwood flooring, vaulted ceilings w/ceiling fan, the space flows to the well appointed kitchen w/Maple cabinetry, granite countertops, pantry, updated appliances include a 5 burner stove, microwave, dishwasher (2026) and refrigerator. The primary bedroom has an organized walk in closet, bathroom with double sink and walk in shower. 🚿 The sunroom was renovated in 2025 enhancing the area to allow for year round use, pond views 💻☕️☀️ The additional bedrooms have large closets, ceiling fans, new carpet and fresh paint. Hall bath w/tub and linen closet. Convenient laundry area w/new washer & dryer. 🧺 Woods Cove not only offers convenience to everything, also allows for carefree living having all exterior maintenance taken care of, community amenities include a picnic pavilion overlooking a community pond, playground, shuffleboard, bocce ball courts & horse shoes are available for enjoyment.

18877 Bent Anchor Ct Unit 3104, Rehoboth Beach

Listing courtesy of NextHome Tomorrow Realty. Contact:

24160 Port Ln Unit 101, Lewes
$329,900
2 Beds ⋅ 2 Baths
THE VIEW, THE VALUE, THE VINEYARDS! Why look out at another building or a parking lot when you can look at a beautiful pond? Welcome to easy coastal living in this first floor end unit condo with amazing pond views in The Vineyards at Nassau Valley. Enjoy peaceful pond views from every room! Enjoy your morning coffee or al fesco meal on the covered porch overlooking the tranquil pond. The living area is filled with natural light from multiple windows that frame calming pond vistas. This inviting condo offers a blend of style, comfort, and everyday convenience in a serene setting. Easy care LVP flooring compliments most of the condo while granite countertops and stainless steel appliances anchor the open kitchen. The open floor plan allows effortless interaction between the kitchen and living spaces, making gatherings with family and friends both comfortable and enjoyable. Both bedrooms have brand new carpet. Residents of The Vineyards of Nassau Valley enjoy an exceptional amenity rich lifestyle including a beautiful clubhouse with a fitness center and billiards room, outdoor pool, fire pit and grilling areas, a fishing pier, dog park, walking trails, picnic areas, volleyball, pickleball courts, horseshoes and easy access to the bike trail network. Bike to historic downtown Lewes, Lewes Beach, and Cape Henlopen State Park. With shopping and services right in the community, and convenient access to Route 9 and Coastal Highway, everything you need and want is nearby. Enjoy affordable water views, convenience, low maintenance living and a relaxed coastal lifestyle at The Vineyards at Nassau Valley!

24160 Port Ln Unit 101, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

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