Cape Henlopen Homes with Colonial Style

Cape Henlopen Homes with Colonial Style

Welcome to Cape Henlopen, a vibrant and welcoming school district located in the picturesque Sussex County, Delaware. Known for its commitment to academic excellence and a holistic approach to education, Cape Henlopen School District serves a diverse community of students and families. With a strong emphasis on fostering critical thinking and creativity, the district boasts a variety of educational programs, dedicated faculty, and modern facilities that cater to the needs of every learner. From innovative STEM initiatives to arts and athletics, Cape Henlopen ensures that students are well-prepared for their future endeavors.

Families looking to settle in this charming area will find an array of beautiful homes, particularly those showcasing the timeless elegance of Colonial-style architecture. These homes, characterized by their symmetrical facades, classic gabled roofs, and inviting front porches, exude a sense of history and charm that perfectly complements the coastal lifestyle of Delaware. With spacious interiors and ample outdoor spaces, Colonial homes provide the ideal backdrop for family gatherings and creating lasting memories.

Living in Cape Henlopen not only offers access to top-notch educational opportunities but also places you within a stone's throw of stunning beaches, nature trails, and vibrant local culture. Whether you’re strolling along the scenic boardwalk or enjoying outdoor activities at nearby parks, this community truly embodies the best of coastal living. Explore the unique blend of history, education, and lifestyle that Cape Henlopen has to offer, and discover your dream Colonial home in this enchanting part of Delaware!

Newest Cape Henlopen Homes with Colonial Style

6 Beds ⋅ 5 Baths

6-7 bedrooms and 5 full baths! Amazing location; East of Route 1. A refined coastal retreat wrapped in lush, European‑sculpted greenery, this residence at 41218 Gloucester Drive delivers privacy, elegance, and a curated sense of arrival that sets it apart in Rehoboth Beach’s most desirable enclave. The moment you approach the property; the landscaping becomes the signature. Hand‑sculpted European trees—shaped with the precision of formal gardens in Provence or Lake Como—create a natural architectural frame around the home. Their tiered canopies and sculpted silhouettes offer Estate‑level privacy without sacrificing sunlight. Old‑World Garden character that elevates curb appeal. The rear yard has sound‑buffering greenery ideal for serene outdoor living. This is landscaping as luxury design, not decoration. The backyard unfolds like a private European courtyard—intimate, green, and beautifully composed. The sculpted trees create natural “rooms” outdoors, perfect for: Al fresco dining under manicured canopies, enjoy morning coffee with the hummingbirds. This is outdoor living designed for both tranquility and entertaining. The first floor features a stunning two-story family room with stone fireplace, coffered ceilings, and hand scraped hardwood floors, The chef’s kitchen is accented by a 5-burner cooktop, large island, quartz counter & backsplash, lots of cabinets, and walk-in pantry. Rounding out the first floor is a dedicated office/den with full bath, and the primary bedroom complete with tray ceiling, expansive walk-in closet with built ins and primary bathroom with soaking tub, shower, and dual vanities. Head upstairs and you will find a large loft living area, a second bedroom that has a private full bath as well as a third bedroom connected to a full bath and fourth bedroom. The finished basement features a large open area with a full kitchen, dining room, living room, 2 bedrooms, a full bath, and storage room. The home has a large private composite deck with dual arbors, custom lighting. fenced back yard, lush landscaping. and irrigated lawn with an AG well. There is an oversized garage with a large storage alcove. Just 1 mile to restaurants, shopping, Downtown Rehoboth Beach and 2 miles to the Boardwalk and beach. Walk or bike the adjacent Junction and Breakwater Trail with miles of trails that connect Rehoboth, Lewes, Cape Henlopen State Park. The community offer two pools, tennis, fitness centers, and waterfront park. The HOA cuts and fertilizes your lawn which gives you more time to relax. Come enjoy this amazing lifestyle. Owners are licensed DE Realtors.

41218 Gloucester Dr, Rehoboth Beach

Listing courtesy of RE/MAX Realty Group Rehoboth. Contact: 3022274800

3 Beds ⋅ 3 Baths

RARE OPPORTUNITY TO BE SO CLOSE TO DOWNTOWN LEWES AND BEACHES AT THIS PRICE POINT! The tucked away Bay Breeze neighborhood is right next to the entrance to downtown Lewes and also Freeman Highway leading to Lewes Beach, the Cape-May Lewes Ferry and Cape Henlopen State Park. This two story, 3 bedroom, 2.5 bath house has an open floor plan with hardwood floors and a spacious living room featuring a white brick gas fireplace. The kitchen has stainless steel appliances surrounded by plenty of cabinetry and a walk-through pantry. The dining area leads to the screened porch and patio with outdoor shower. The large backyard has a private entrance through a canopy of trees to the Junction & Breakwater walking trail. Upstairs, the large primary bedroom has a walk-in closet and updated en-suite bath. Home also conveniently has an office, laundry room and 1-car garage all on almost a .25 acre lot.

20 Bay Breeze Dr, Lewes

Listing courtesy of Jack Lingo - Lewes. Contact: (302) 645-2207

5 Beds ⋅ 5 Baths

Welcome to 18320 Highwood Drive, located in the heart of Wellesley, an exceptional opportunity to own a true luxury corner-lot residence, ideally positioned near the Delaware coast and just moments from beautiful beaches. Situated on a premium corner lot, this impressive home offers 4,351 square feet of thoughtfully designed living space, providing the perfect balance of sophistication, comfort, and functionality for both everyday living and effortless entertaining. Adding to its appeal is an unfinished basement, offering endless possibilities to create a home gym, theater, recreation room, additional bedrooms, or whatever best suits your lifestyle. Step inside to discover bright, inviting spaces with a floor plan designed for modern living. Another standout features is the screened porch overlooking the tranquil pond—the perfect place to enjoy your morning coffee, unwind with a good book, or entertain guests while taking in peaceful views. From its exceptional curb appeal and sought-after corner-lot setting to its serene pond views and unbeatable location near Delaware's award-winning beaches, this home offers a rare combination of luxury, privacy, and lasting value. Don't miss your opportunity to make 18320 Highwood Drive your next home. Schedule your private showing today!

18320 Highwood Dr, Rehoboth Beach

Listing courtesy of Iron Valley Real Estate Premier. Contact: 3027414545

5 Beds ⋅ 4 Baths

FORMER MODEL HOME ON AN OVERSIZED LOT IN THE VILLAGES AT RED MILL POND! This beautifully maintained 4-bedroom home, complete with a spacious second-floor bonus room that can easily serve as a fifth bedroom, showcases exceptional craftsmanship, timeless architectural details, and premium finishes throughout. A grand double-door entry welcomes you into a dramatic foyer with soaring ceilings and stately columns, creating an impressive first impression. Flanking the foyer are elegant formal living and dining rooms, highlighted by a bay window and tray ceiling, offering the perfect spaces for entertaining and special occasions. Designed with both function and style in mind, the spacious wraparound kitchen is a chef's dream, featuring abundant cabinetry, stainless steel appliances, a center island, a peninsula with seating, and seamless flow into the sun-filled morning room with a vaulted ceiling. The adjacent two-story great room is filled with natural light from a dramatic wall of windows and features custom built-ins surrounding a cozy gas fireplace. The main level also offers the convenience of a first-floor laundry room, a powder room for guests, and interior access to the attached two-car garage. The first-floor primary suite offers a private retreat with a sitting area framed by a bay window, elegant columns, a tray ceiling, a walk-in closet, and a spacious en-suite bath with dual vanities, a tiled shower, and a separate soaking tub. Upstairs, an open balcony overlooks the great room below and leads to three generously sized guest bedrooms, each with convenient access to a connecting bathroom, as well as the expansive bonus room that offers endless flexibility as a fifth bedroom, media room, home office, or playroom. Outside, enjoy your own private backyard oasis. The oversized deck provides the ideal setting for outdoor dining, entertaining, or simply relaxing while surrounded by mature landscaping. Lawn irrigation supplied by a private well helps maintain the beautifully landscaped grounds and enhances the home's exceptional curb appeal. Recent updates include a brand-new roof and a newer secondary HVAC system, providing added value and peace of mind. Residents of The Villages at Red Mill Pond enjoy resort-style amenities, including a clubhouse, community pool, kayak and paddleboard access to Red Mill Pond, and direct access to the Lewes-Georgetown Trail. Ideally located just minutes from downtown Lewes, Lewes Beach, Cape Henlopen State Park, shopping, dining, and Delaware's award-winning beaches, this exceptional home offers the perfect blend of luxury, comfort, and coastal living. Whether you're looking for a primary residence, a vacation home near the beach, or an investment opportunity in Lewes, this exceptional property is ready to welcome you home. Call Today!

18680 Golden Sunrise Pl, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3026456661

4 Beds ⋅ 3 Baths

One-of-a-kind custom-built home situated on a beautifully landscaped ¾-acre cul-de-sac lot in a well-established community, The Cove at Herring Creek, offering a clubhouse and pool. This spacious 4-bedroom, 3-bath home features approximately 2,800 square feet of living space, including a bonus room and abundant walk-in storage and closets. Located just minutes from Delaware’s beaches, this home offers the perfect balance of coastal convenience and peaceful living away from the seasonal hustle and bustle. A welcoming front porch sets the tone for the warmth and character found throughout the home. Inside, the thoughtfully designed floor plan showcases rich wood details, a stunning two-story living room featuring an open staircase with a second-floor overlook, beautiful hardwood flooring and a cozy fireplace. It also offers a first-floor primary suite with large primary bath including a jetted tub. A versatile main-level bonus room with access to a full bath provides flexibility for a home office, study, guest room, or hobby space. The custom design blends comfort and functionality throughout creating an inviting living space filled with timeless charm. Outdoor living is just as inviting with a spacious deck, gazebo-style screened porch, and a private backyard that’s perfect for relaxing, gathering with family and friends, or simply enjoying the peaceful setting. Additional features include a large two-car garage and exceptionally large driveway. Professional photography and additional details will be available when this home becomes Active. Stay tuned for this unique opportunity in one of Lewes’ most desirable communities. Additional updates and features include a roof less than five years old, geothermal HVAC system, irrigation system, and energy-efficient living. Located just minutes from Delaware’s beaches, this home offers the perfect balance of coastal convenience and peaceful living away from the seasonal hustle and bustle. Don’t miss this rare opportunity to own a truly unique custom home in one of the area’s most desirable communities.

23452 Osprey Ct, Lewes

Listing courtesy of Keller Williams Realty. Contact: 3023600300

3 Beds ⋅ 3 Baths

Located in the charming Maplewood community, this inviting Colonial-style home offers the perfect blend of comfort, functionality, and modern updates. Thoughtfully upgraded and designed in 2025 with everyday living in mind, this home features three bedrooms and well-appointed living spaces that create a warm and welcoming atmosphere. Inside, you'll find a combination of plush carpeting and luxury vinyl plank flooring that provides both style and durability. The spacious kitchen is equipped with upgraded countertops and stainless steel appliances, including a built-in microwave and electric range, making meal preparation both convenient and enjoyable. Natural light fills the home through energy-efficient double-hung windows, while recessed lighting and ceiling fans add comfort throughout. The home's bathrooms have been designed with convenience in mind and include a variety of features to accommodate everyday living. A cozy breakfast area provides the perfect place to enjoy your morning coffee or gather with family and friends. Step outside and discover one of this property's standout features—a spacious rear deck overlooking the backyard, creating an ideal setting for entertaining, summer barbecues, or simply relaxing and enjoying the peaceful surroundings. The generously sized yard is enhanced by mature trees and offers plenty of room for outdoor activities, gardening, or creating your own private retreat. Additional exterior highlights include attractive landscaping, outdoor lighting, a well-maintained gutter system, and an attached two-car garage with a concrete driveway for added convenience. The Maplewood community offers residents access to wonderful amenities, including a community pool and recreational facilities, providing opportunities to relax, socialize, and enjoy an active lifestyle. With major renovations and a desirable location close to everyday conveniences, this home offers the perfect combination of comfort, outdoor living, and community amenities. Don't miss your opportunity to make this beautiful Maplewood property your next home.

20 Colgate Dr, Rehoboth Beach

Listing courtesy of Coldwell Banker Premier - Lewes. Contact: 3026452881

4 Beds ⋅ 3 Baths

Welcome to this beautifully maintained, nearly new home in the desirable Windswept at Lewes community, where modern comfort, thoughtful design, and coastal convenience come together. Built just two years ago, this spacious four-bedroom, two-and-a-half-bath home offers an open, light-filled floor plan that's perfect for everyday living, entertaining, or simply relaxing after a day at the beach. The welcoming foyer leads into an expansive living area featuring luxury vinyl plank flooring, recessed lighting, and abundant natural light. At the heart of the home, the kitchen showcases crisp white cabinetry, generous counter space, a gas range, a center island with seating, and easy access to the backyard, creating an ideal gathering place for family and friends. Upstairs, the spacious primary suite offers a walk-in closet and private bath with dual vanities, while three additional bedrooms provide flexibility for guests, family, or a home office. Step outside to enjoy the fully fenced backyard, perfect for pets, outdoor entertaining, or quiet evenings in your own private retreat. The professionally landscaped front yard adds welcoming curb appeal, while the unfinished basement, already roughed in for a future bathroom, provides endless possibilities to expand your living space with a recreation room, guest suite, fitness area, or home office. Windswept at Lewes offers the perfect balance of peaceful neighborhood living with convenient access to everything coastal Delaware has to offer. You're just minutes from historic downtown Lewes, Rehoboth Beach, Cape Henlopen State Park, shopping, restaurants, golf, boating, and miles of beautiful beaches. A minimum 30-day rental policy also makes this property an excellent option for those seeking flexibility as a primary residence, second home, or investment opportunity. Move-in ready, nearly new, and offering exceptional value in today's Lewes market, this is an opportunity you won't want to miss.

30045 Moorings Reach, Lewes

Listing courtesy of Compass. Contact: 3022734998

4 Beds ⋅ 4 Baths

Experience the best of coastal Delaware living at this extraordinary waterfront estate, set on more than 4 private acres along the stunning Rehoboth Bay. This one-of-a-kind property offers unmatched privacy, breathtaking views, and endless possibilities for year-round living, a vacation retreat, or an investment opportunity. The main residence features 4 spacious bedrooms and 3.5 bathrooms, with light-filled living spaces designed to capture panoramic bay views from nearly every angle. Expansive windows invite the beauty of the outdoors in, creating a warm and inviting atmosphere perfect for both everyday living and entertaining. Step outside and discover your own private waterfront sanctuary. Enjoy direct bay access from your private dock, soak in spectacular sunsets, and embrace the natural beauty that surrounds you. Watch bald eagles soar overhead while deer and other wildlife roam the grounds, all from the comfort of your patio or porch as refreshing bay breezes drift by. Adding even more value and versatility, the property includes a charming carriage house above the oversized 3-car garage—ideal for hosting guests, creating a private home office, multigenerational living, or generating rental income. Rarely does a property offer this combination of acreage, waterfront access, privacy, wildlife, and proximity to Rehoboth Beach. Whether you're seeking a luxury primary residence, a coastal getaway, or an income-producing retreat, this exceptional bay front property delivers a lifestyle few can match. Listing agent to provide 1 year Home Warranty to buyers. Listing agent will also have home professionally power washed and interior cleaning after closing.

21440 Bald Eagle Rd, Rehoboth Beach

Listing courtesy of Samson Properties of DE, LLC. Contact: 3024023046

3 Beds ⋅ 1 Baths

"Beach" Get-A-Way - 3BR Milton home w/spacious front porch & fenced yard. Space for 1st floor BR, garage & pool. New roof, updated plumbing, electric HVAC & insulation. In the center of the Historic District, walk to restaurants, farmers market, live theatre, art galleries, museum, library & ice cream. Friends meet at Dogfish Head Brewery famous 4 beer, food & festivals. Enjoy live Music in the Park & St. Patties Day & Christmas Parades. Minutes to Lewes, Cape Henlopen State Park, Rehoboth Beach Route 1 outlets. NO HOA, LOW TAXES.

203 Walnut St, Milton

Listing courtesy of Jack Lingo - Rehoboth. Contact: (302) 227-3883

7 Beds ⋅ 6 Baths

Welcome to coastal luxury in the highly sought-after Rehoboth Beach Yacht & Country Club, one of Delaware's premier waterfront and golf course communities, just minutes from downtown Rehoboth Beach, the boardwalk, shopping, dining, and the Atlantic Ocean. This exceptional 7-bedroom, 5.5-bath residence offers the perfect blend of elegance, comfort, and space for both year-round living and unforgettable beach getaways. Designed with entertaining and everyday living in mind, the home features expansive indoor and outdoor living areas, including a welcoming front porch, spacious deck, and private balcony ideal for enjoying coastal breezes and peaceful surroundings. The thoughtfully designed floor plan provides generous bedroom accommodations, multiple gathering spaces, and abundant natural light throughout. An attached garage offers convenience and additional storage for beach gear, golf clubs, and recreational equipment. Whether you're hosting family and friends, relaxing after a day at the beach, or enjoying the nearby golf, boating, and country club lifestyle, this remarkable property delivers the ultimate Rehoboth Beach experience. Rarely does a home of this size and caliber become available in one of the area's most desirable communities. Experience luxury coastal living at its finest in Rehoboth Beach Yacht & Country Club.

102 London Cir S, Rehoboth Beach

Listing courtesy of Samson Properties of DE, LLC. Contact: 3024023046

5 Beds ⋅ 7 Baths

A beautifully appointed home just a few blocks from the beach and downtown Rehoboth Beach, 53 Fields End is centrally located in the sought-after town of Henlopen Acres which features a private beach, private marina* and access to a private beach club* *and tennis club. This home is tastefully designed on three levels and sits on over 1/2 an acre corner lot. As you walk into the home you are welcomed by a well appointed foyer with vaulted ceilings and a cozy sitting room. The well thought design flows gently into an open concept living area where you find a gourmet kitchen, dining area and living space which is filled with natural light throughout the day. The dining area and living room are customized with built-in storage spaces, gas fireplace, recessed lighting, upgraded hanging lighting, and multiple ceiling fans create an updated yet cozy feel. The living space opens to the screen-porch to relax, read a book, or entertain family and friends. The screen porch can also be accessed through doors in the dining room and the first-floor primary suite. The first-floor primary suite is a true owner’s retreat, complete with a walk-in closet and a spa-like bathroom with heated floors. The home's ground floor features multiple storage spaces, a media room, a full bathroom and a large recreation room with direct access to the backyard which features a hardscape patio and built-in firepit. Next to the patio is a large outdoor storage area, just right for beach gear, bikes, lawn equipment, and more. The top floor features an additional primary suite with a large walk-in closet and bathroom. There are also three additional bedrooms, each with its own en-suite bathroom, as well as a large sitting room/ office and a bonus feature an additional laundry room, and attic for storage. To top off the features there is a 2-car attached garage and an outdoor shower. Every upgrade and update has been thoughtfully designed to provide a comfortable, laid-back, coastal lifestyle. Location is everything - located less than a mile to all of downtown Rehoboth Beach’s most popular amenities and attractions, yet tucked away in a quiet, serene setting of Henlopen Acres. *Marina - wait-list. ** Private Beach Club requires a separate membership.

53 Fields End, Rehoboth Beach

Listing courtesy of Jack Lingo - Lewes. Contact: (302) 645-2207

4 Beds ⋅ 5 Baths

Historic 1.64-Acre Luxury Estate Compound Near Delaware Beaches Steeped in 216 years of rich history, the iconic Mansion Farm Inn offers an unrepeatable private estate compound balancing old-world heritage with modern luxury. Nestled on 1.64 tranquil acres framed by mature evergreens and serene country scenery, this sprawling property is perfect for multi-generational living or a grand coastal retreat. The stately main house features 3 exquisitely curated bedroom suites, each serving as a private sanctuary with its own premium en-suite bathroom (complete with soaking tubs and walk-in showers), cozy sitting areas, smart TVs, and all-season ambiance fireplaces. The property also features a versatile upstairs flex room complete with a closet and a pull-down Murphy bed, offering excellent additional space. Behind the main house, a flawlessly renovated detached barn hosts 2 fully self-contained accessory apartments. Perfect for independent guest quarters, long-term family stays, or an au pair suite, both units boast full kitchens, open living spaces, and private in-unit laundry. The spectacular exterior functions as a world-class private resort. Further enhancing the estate's exceptional flexibility is a detached 2-car garage crowned by an impressive third private suite. Thoughtfully designed across 2 levels, this residence features a full kitchen and inviting living area on the main floor, while the upper level offers a spacious bedroom and full bathroom. Whether utilized as sophisticated guest accommodations, private quarters, or a secluded retreat, this additional living space provides endless possibilities. A massive, sparkling saltwater pool serves as the centerpiece, surrounded by an extensive paved sun deck, curated courtyard paths, soothing fountains, and a cozy backyard fire pit. A covered garden porch with a built-in hospitality bar flows seamlessly out onto massive composite decking built for grand-scale entertaining. The property also includes multiple detached outbuildings, a historic barn/workshop, and a premium ground-mounted solar panel array for maximum energy efficiency. Perfectly positioned along Broadkill Road, you are just 5 miles to the peaceful shores of Broadkill Beach, 8 miles to historic Lewes, and 13 miles to the iconic Rehoboth Beach boardwalk. Enjoy absolute rural privacy with immediate access to tax-free outlet shopping, local amusements, and award-winning coastal dining.

26285 Broadkill Rd, Milton

Listing courtesy of The Parker Group. Contact: 3022176692

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