Cape Henlopen Homes with Pool

Cape Henlopen Homes with Pool

Welcome to the picturesque Cape Henlopen School District, located in the heart of Sussex County, Delaware. This vibrant community is not only known for its stunning coastal scenery and rich history but also for its commitment to providing an exceptional education for its students. The Cape Henlopen School District serves a diverse population and encompasses several towns, including Lewes, Rehoboth Beach, and Milton. With a focus on fostering a nurturing and engaging learning environment, the district boasts a range of academic programs, extracurricular activities, and dedicated teachers who inspire students to reach their full potential.

Living in this charming region offers more than just access to quality education; it also provides an idyllic lifestyle enriched by outdoor activities and community events. For families seeking homes with pools, Cape Henlopen is a treasure trove of options. Imagine spending warm summer days lounging by your private pool, perfect for entertaining friends or enjoying quiet moments with family. These homes often feature spacious backyards, allowing for both relaxation and recreation, with the added bonus of being just a stone's throw away from Delaware's beautiful beaches.

Whether you're looking to settle down in a family-friendly neighborhood or find a vacation retreat, the Cape Henlopen area has something for everyone. With its excellent schools, welcoming community, and homes that offer pools for those sun-soaked days, this is a place where memories are made and cherished. Explore the possibilities of calling Cape Henlopen home, and experience the perfect blend of education, leisure, and coastal charm!

Newest Cape Henlopen Homes with Pool

2 Beds ⋅ 1 Baths

Discover affordable coastal living just minutes from Delaware's beautiful beaches. This charming home features a completely updated kitchen and bathroom, along with fresh paint throughout, creating a bright, clean, and inviting space that's move-in ready. Located in the peaceful Sea Air Village community just off Route 1, you'll enjoy the perfect combination of convenience and tranquility. Whether you're looking for a full-time residence or a relaxing beach getaway, this home offers an exceptional opportunity to own an affordable retreat near the coast. You'll be just minutes from Delaware's award-winning beaches, the scenic bay, the lively boardwalk, outlet shopping, and an excellent selection of local restaurants. Plus, the Cape May–Lewes Ferry is nearby, making day trips and coastal adventures easy. Community Requirements: Buyers must receive park approval prior to settlement. Park application fee: $50 per person. Don't miss this opportunity to own an affordable home in one of Delaware's most desirable coastal locations!Picnic Area, Pool - Outdoor, Tot Lots/Playground

20011 Delaware Ave Ave, Rehoboth Beach

Listing courtesy of The Lisa Mathena Group, Inc.. Contact: (855) 334-6637

4 Beds ⋅ 4 Baths

Welcome to 19322 Loblolly Cir, a charming coastal retreat located in the beautiful Rehoboth Beach, DE. This delightful property offers the perfect blend of comfort and convenience, making it an ideal choice for those seeking a serene beach lifestyle. As you enter the home, you are greeted by an inviting open floor plan that combines the living, dining, and kitchen areas, providing a great space for entertaining family and friends. The living area features ample natural light and offers a cozy atmosphere for relaxation. A standout feature of this home is the first-floor primary suite, which provides privacy and convenience with easy access to all the main living areas. This suite offers a comfortable space with an ensuite bathroom, making it a perfect retreat at the end of the day. The kitchen is equipped with modern appliances, providing everything you need to prepare meals, and includes plenty of cabinet and counter space to satisfy your culinary needs. On the second floor, you'll find a second primary suite, which offers additional luxury and privacy. This spacious suite includes its own ensuite bathroom, making it ideal for guests or as a personal sanctuary. Additionally, the second floor features two more bedrooms that share a full bathroom, offering ample space for family or visitors. An exciting feature on the second floor is a huge unfinished room that presents endless possibilities. This space could be easily transformed into an additional finished bedroom, providing even more flexibility and accommodation options. The property also features a conditioned basement, which can be easily finished according to your needs. With plumbing already in place for adding a bathroom, this space offers tremendous potential for expansion, whether you envision a home theater, gym, or additional living area. Outside, the back of the house features a beautiful stone courtyard, perfect for outdoor gatherings and barbecues on warm afternoons. This charming area offers a lovely setting to enjoy the tranquility of your surroundings. Residents of Arbor Lyn enjoy access to community amenities, including a clubhouse and swimming pool. The clubhouse serves as a welcoming gathering space for social events and activities, while the swimming pool offers a refreshing escape on hot summer days. One of the added benefits of living in this community is the low-maintenance lifestyle. The HOA takes care of lawn maintenance and snow removal, giving you more time to relax and enjoy your home. Situated in the well-loved Rehoboth Beach, you are just minutes away from stunning beaches, local dining, shopping, and entertainment. This location provides easy access to all that the Delaware coastline has to offer. Don't miss the opportunity to make 19322 Loblolly Cir your new home or vacation getaway. With its prime location, dual primary suites, potential for further customization, versatile basement space, and community amenities, this property is ready for your personal touch. Schedule your showing today!

19322 Loblolly Cir, Rehoboth Beach

Listing courtesy of Patterson-Schwartz-OceanView. Contact: (302) 537-1300

2 Beds ⋅ 2 Baths

Live next to Dogfish Head Brewery for under $300K! Offering 1,256 square feet of comfortable living space, this well maintained 2-bedroom, 2-bath condominium in desirable Cannery Village features an open, thoughtfully designed floor plan with generously sized rooms, a large, sun-filled living area and large open air balcony perfect for relaxing or entertaining. With a private entrance on the first level and all living space on the second floor, you’ll enjoy added privacy and a bright, airy feel throughout. Freshly painted from top to bottom, this home is move-in ready and includes a brand-new refrigerator and stove, a dishwasher replaced in 2022, a new HVAC condenser unit installed in 2022, and professionally cleaned carpeting. One of the home’s greatest features is its unbeatable location. Enjoy an easy walk to historic downtown Milton, where you’ll find charming restaurants, coffee shops, boutiques, parks, The Milton Theatre and year-round community events . You’re also just steps from the renowned Dogfish Head Brewery and can take advantage of Cannery Village’s outstanding community amenities including an indoor and outdoor pool! Lewes, Rehoboth Beach, and the rest of Delaware’s award-winning beaches are all just a short drive away. With spacious interiors, low-maintenance living, a highly walkable location, and an attractive price point under $300,000, this is an exceptional opportunity to own in one of Milton’s most sought-after communities.

903 Canning House, Milton

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

2 Beds ⋅ 2 Baths

Beachaven has the beach location you want! It is just a 3-mile drive to the Rehoboth boardwalk and a wee bit over 5 miles to the Lewes public beach. Beachaven is also near the Wolfe Neck trailhead to the State Park hiking/biking trail. Third-floor condo has a screened balcony overlooking the common grounds and the community pool, which is shared with Seabright townhouse owners. The single-level floor plan has the breakfast bar kitchen at the entryway hall. The kitchen has a dishwasher, electric range, range hood & a fridge. The dining area and living room are adjoining. There is a retro wet bar in the living room, and a sliding glass door to the screened balcony. The main bedroom is en Suite, with that bath having a single-sink vanity and a walk-in shower. The second bedroom has easy access to the second full bath, which has a tub/shower combo. Big laundry room with a side-by-side washer and dryer. Electric water heater. Electric HVAC for heat and air conditioning. Tenant occupied with a Lease term through the end of December 2026; Tenants are willing to stay if you’re buying the condo as an investment. Plenty of parking. Total condo dues include the regular COA fee, a reserve fund contribution, and a limited $100/quarter assessment.

35979 Condo Dr Unit #B-303, Rehoboth Beach

Listing courtesy of SEA BOVA ASSOCIATES INC.. Contact: (302) 227-1222

4 Beds ⋅ 3 Baths

COASTAL CHARM MEETS LUXURY LIVING! Discover the perfect fusion of style, space, and serenity in this stunning 4-bedroom, 2.5-bath home in sought-after Paynters Mill. This home blends timeless style with everyday comfort. The interior features a gourmet kitchen with granite countertops, stainless steel appliances, breakfast bar, & breakfast nook — perfect for culinary enthusiasts. Enjoy two spacious living rooms (one up and one down), two guest rooms on the second floor, and a first-floor guest room. The primary suite provides a serene retreat with an en suite bath and 2 generous walk-in closets. Relax on your rear screened porch, the perfect place to enjoy your morning coffee. Other highlights include a full, unfinished basement that offers tons of storage, outside shower, formal dining room, and more! Community amenities include a clubhouse with fitness center and billiards table, outdoor pool, tennis and pickleball courts, beach volleyball, and walking/biking paths. This home truly offers the perfect combination of elegance, comfort, and community living — all just minutes from downtown Lewes and the beaches.

16269 John Rowland Trl, Milton

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

3 Beds ⋅ 3 Baths

Prime East of Route 1 coastal location - minutes to beaches, trails, and the best of Lewes. New Construction • Delivery November 2026 Welcome to The Eastwood Loft —a charming, cottage style ranch home offering true first floor living in one of Delaware’s most exclusive, award winning coastal communities. Thoughtfully designed with 2,441 square feet of refined comfort, this 3 bedroom, 3 bath residence blends modern luxury with warm, inviting character. Step inside to upgraded LVP flooring throughout, upgraded lighting packages, and an open concept layout anchored by a stunning gourmet kitchen. Enjoy upgraded quartz countertops, a large center island, stainless steel appliances, built in double wall ovens, built in cooktop, French door refrigerator, stainless steel appliances and a farmhouse sink. The adjacent great room features a cozy fireplace and opens seamlessly to the rear screened porch and a 12’ x 14’ exterior deck—perfect for relaxing or entertaining. The upgraded primary suite is a true retreat, showcasing a spa inspired bathroom with a frameless glass shower enclosure, tile to the ceiling, a tiled pan floor, and three shower heads for a luxurious experience. Additional highlights include a dedicated laundry room with cabinet package and utility sink, natural gas heat, gas cooking, a tankless Rinnai hot water heater, and a 4’ conditioned crawlspace for enhanced efficiency and storage. Outside, enjoy a covered front porch and a homesite positioned within a serene, natural setting—surrounded by open space, wildflower plantings, and thoughtfully preserved landscapes. Unmatched Coastal Location: Just a 15 minute bike ride to the beach, ½ mile to the Lewes–Georgetown Bike Trail, and 1 mile to the Lewes/Rehoboth Canal. Minutes from Cape Henlopen State Park, the Cape May–Lewes Ferry, and all the charm of historic Lewes. Ideally situated east of Route 1 for effortless coastal living. Resort Style Community Amenities: Live in the 2025 Regal Award–Winning Community of the Year, offering an unparalleled lifestyle: • Zero entry resort style pool & hot tub • Pickleball courts & a tennis court • Community garden • Outdoor pavilion, grill areas & fire pits • Horseshoes, shuffleboard & bocce ball • Tot lot & outdoor workout space • Nature trails, wildflower meadows & honey bee hives • Expansive great lawn for events • Lifestyle Director coordinating yoga, Pilates, Zumba, strength training, cooking demos, lunch and learns, wine & beer tastings, brewery tours, live music, and more A Rare Opportunity Homes here are selling fast with limited availability. This highly sought after, one of a kind coastal community offers an unmatched blend of luxury, nature, and lifestyle. Don’t miss your chance to own The Eastwood—a brand new home in an award winning setting, ready just in time for Summer 2026. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

15468 Solomon Way, Lewes

Listing courtesy of Delaware Homes Inc. Contact: 3023789510

3 Beds ⋅ 3 Baths

Prime East of Route 1 coastal location - minutes to beaches, trails, and the best of Lewes. Welcome to the Lewes, a beautifully designed home that blends an open-concept layout with timeless elements. Scheduled for settlement in November, this home offers 3 bedrooms, 2.5 baths, and a 2-car side-entry garage, delivering both elegance and functionality. The main living area features a cozy fireplace in the great room, creating a warm and inviting space for gathering. A dedicated study/office provides the perfect setting for working from home, while a butler’s pantry adds both convenience and sophistication for entertaining. The screened deck extends your living space outdoors, ideal for relaxing or hosting guests. The ultra-gourmet kitchen is designed to impress, featuring double wall ovens, a gas cooktop, and quartz countertops for both beauty and performance. LVP flooring flows throughout the home, offering a cohesive and durable finish. The primary bath includes an ultra spa bath, creating a luxurious retreat to unwind and recharge. 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.

33808 Joel Ln, Lewes

Listing courtesy of Delaware Homes Inc. Contact: 3023789510

2 Beds ⋅ 2 Baths

17312 Pine Water Dr, Lewes

Listing courtesy of Northrop Realty. Contact: (302) 539-2900

2 Beds ⋅ 2 Baths

Location, location, location! This home sits in Angola Beach and Estates, a true marina community tucked along the banks of Burton Prong on the western side of Lewes, where the river winds its way out to Rehoboth Bay. This is the kind of place where life slows down and the outdoors becomes part of your everyday routine. Enjoy community boat slips, a fenced storage yard for your boat, trailer, RV, or jet skis, a fishing pier, and kayak and canoe racks, all just steps from your door. Take in gorgeous water views, cast a line, paddle out at sunset, or simply enjoy the peaceful rhythm of river life. Beyond the water, the community offers two swimming pools, two playgrounds, a full sized tennis court, and a basketball court, plus pet waste stations throughout for easy dog walking. This particular home is ideally located right next to the community's second pool, the courts, and the playground, putting you steps from it all. The home itself is a 1972 Skyline doublewide, full of character and ready for someone with a creative eye and a love of DIY projects to make it their own. Inside, you'll find two bedrooms and one and a half bathrooms. The hall bathroom has been nicely remodeled with new fixtures, flooring, and even a new window. The owners bedroom is generously sized with an ensuite half bath and abundant closet space. Fresh, bright white paint runs throughout, giving the home a clean, welcoming feel. The kitchen is large and inviting, with oak cabinetry that was replaced at some point over the years, offering plenty of storage and generous counter space for anyone who loves to cook or bake. You'll find a gas range and a refrigerator, along with a space ready for a dishwasher. There's also a formal dining room plus a second dining space right in the kitchen, complete with a charming bay window and built in storage underneath. The living room is full of character too, featuring a brick accent wall with a mantel, a pellet stove for cozy, efficient heat, and attractive built in cabinetry and shelving. A propane furnace and window unit air conditioning round out the comfort options, and a screened porch offers the perfect spot to enjoy the outdoors bug free. This home is being sold as is, and being a pre-HUD Code mobile home, buyers should note it may be more difficult to finance through traditional means. The age of the roof and furnace are unknown. This is not a home for someone seeking fresh, new, and modern. But for the right buyer, someone who sees the potential, loves a project, and wants an unbeatable location, this could be an incredible opportunity. Rehoboth Beach and Lewes' resort area beaches are just about 20 minutes away, with shopping, dining, and everyday conveniences a quick 15 minute drive in either direction. Park application required for residency: credit check, background check, and verification of income and/or assets required. Reasonable rent (comparatively speaking!) includes water, sewer and trash service.

33360 South Beach Drive, Lewes

Listing courtesy of Keller Williams Realty. Contact: (302) 360-0300

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 ⋅ 2 Baths

Rehoboth Bay Community has boat slips for rent, a community boat ramp, a storage area for boats/PWCs, a bayfront pool, a crabbing/fishing pier, a small sandy beach near the pool, tennis/pickleball courts & more! And it is just 6.5 miles to the famous Rehoboth boardwalk. This 1988 Westgate singlewide home is located right across from the pond for delightful views from the screened porch and from the hardscaped patio in front of the house. And because the home backs to open common grounds, you catch glimpses of the family of deer that live back there! The home’s living room features a wood-burning fireplace. Eat-in kitchen has newer countertops, a breakfast bar, and a dinette area. Split bedroom plan. The main bedroom is en Suite with a walk-in closet. That bath has a newer tub/shower. The other two bedrooms share the second full bath, which has a newer walk-in shower. Hall laundry area with a newer washer & dryer set. Newer luxury vinyl plank flooring. New furnace in 2026. 2022 roof. Other improvements include gutter guards and newer skirting. Shed for your beach & boating gear. Golf carts are permitted. The community allows 2 pets (no fences, though). Leasehold Interest: Lot Rent of approx. $735.57/mt. includes water service & trash/recycle. (Delaware law caps rent increases as per 25 Del. C. Sec 7050-7054 with Lease renewals on Jan. 1). Homeowner pays electric, sewer, LP gas, cable/Internet, and lawn maintenance. Hometown America, the community owner, requires an Application from the Buyer (and all adult occupants 18-year-of-age or older), with acceptance based on the following criteria: 1.)income verification, 2.)credit bureau score, plus evaluation of debt-to-income ratio, and 3.)criminal background check. (Note: Family & friends may always visit, but no short-term rentals (rentals for 6mts or longer may be approved by the Community Manager.) Financing may be available to qualified borrowers from only a very few Lenders who specialize in installment/chattel loans for manufactured homes on leased land. Closing costs will include a real estate transfer tax (3.75% DMV Doc Fee) & a Settlement Agent fee.

21260 G St Unit #G-17, Rehoboth Beach

Listing courtesy of SEA BOVA ASSOCIATES INC.. Contact: (302) 227-1222

2 Beds ⋅ 2 Baths

Turnkey Coastal Haven in Paynters Mill! This Home is all its Fully Furnished with an Updated Kitchen in a Prime Lewes/Milton Coastal Location. Welcome to easy, resort-style living in the highly sought-after community of Paynters Mill! This beautifully updated, fully furnished turnkey condo offers the ideal balance of modern comfort, convenience, and endless coastal charm—just pack your bags and start enjoying the beach lifestyle from day one. The Interior Highlights are : Gourmet Updated Kitchen: Cook and entertain in style with newly updated cabinetry, stylish modern hardware, and gorgeous quartz countertops. Spacious Open Floor Plan: The seamless flow between the kitchen, dining, and main living areas creates an inviting atmosphere filled with natural light—perfect for relaxing or hosting guests. Primary Retreat: Enjoy a generous main bedroom suite complete with a private ensuite bathroom and a roomy walk-in closet. Peace of Mind: Features an HVAC system replaced just one year ago and an oversized 1-car garage providing plenty of room for parking, extra storage, or your beach gear. Paynters Mill offers a unique, vibrant neighborhood feel where everything you need is just steps away. Take advantage of the Resort stle Amenities of community clubhouse, fitness center, outdoor pool, hot tub, library, playground, basketball court, and tennis courts. Community offers walkable lifestyle where you can stroll right from your front door to local neighborhood favorites including a hair salon, cozy breakfast nook, delicious pizza shop, and local dining. The location is a Cyclist’s Paradise with direct access to the local bike trail system (Georgetown-Lewes Trail) making it effortless to hop on your bike and ride straight into Downtown Lewes with seamless connections onward to Rehoboth Beach. Location, Location, Location! Situated just minutes from Historic Downtown Lewes & Savannah Beach, the Tanger Outlets, premier shopping, and dining along Route 1, as well as the Cape Henlopen State Park and coastal Delaware's finest beaches. Whether you're looking for a low-maintenance primary residence, a coastal getaway, or a turnkey investment, this Paynters Mill gem is ready for you!

16359 Abraham Potter Run Unit #205, Milton

Listing courtesy of RE/MAX Associates. Contact: 3026450800

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