5 Bedroom Homes for Sale in Lewes, DE

Nearly $200,000 in thoughtful, high-end custom upgrades invested since purchase. Better than new! This exquisite "Charleston" model, originally crafted by Foxlane Homes in 2023, has been elevated to an absolute masterpiece. Situated on a premium 0.45-acre lot in the custom Villages at Herring Creek neighborhood, this stunning 5-bedroom, 3-bathroom, with approximately 2,950 finished sq. ft. home offers a rare blend of contemporary coastal luxury and move-in-ready perfection! Exquisite Interior Enhancements: Step inside to find an inviting, open floor plan boasting soaring ceilings, luxury vinyl plank flooring throughout (no carpet), and a gourmet kitchen built for entertaining. The sellers spared no expense in perfecting the interior, notice nearly $19,000 in beautiful custom window shutters throughout the home, the replacement of all light fixtures, electrical covers, hardware throughout, gorgeous closet built-ins, custom redesigned laundry room, and coated 3 car garage flooring. The primary suite serves as a true retreat, featuring and as mentioned the heavily upgraded custom closets, complete with stylish barn doors, alongside tasteful primary bath updates and designer light fixtures. Every detail has been meticulously considered, from the upgraded Kwikset Milan door hardware to the completely remodeled laundry room ($9,495 investment) and a custom-built storage room to maximize organization. Even the oversized 3-car attached garage has been upgraded with a professionally finished floor by Pinnacle Concrete. An Outdoor Living Showstopper: Step out back into your private, fully fenced sanctuary. Enclosed by a premium black aluminum fence by Backyard Works, the outdoor living space is an entertainer’s dream. Over $104,000 was invested into bespoke hardscaping and landscaping by Bryan & Sons. Enjoy summer evenings on the expansive Belgard Mega Arbel paver patio and outdoor Kitchenette with XO appliances, surrounded by custom curved retaining walls, hardwired lighting in-ground, beautiful river rock beds, flowering perennials, and lighted mature Dura Heat River Birch trees. Maintaining this lush, vibrant yard is completely cost-effective thanks to the installation of a dedicated agricultural irrigation water well by AquaTech. Plus, enjoy ultimate peace of mind no matter the weather with a newly installed (2026) $11,000 whole-home generator. Resort-Style Community Located in Lewes, the Villages at Herring Creek offers an unparalleled lifestyle with lovely amenities. For a low quarterly HOA fee of just $456, residents enjoy access to a clubhouse, fitness center, community pool, and tennis/pickleball courts. Why wait for new construction when all the hard work and premium customization has already been done for you? Schedule your private tour today and experience the exceptional details of this pristine home! (room measurements are estimated)

34444 Skyler Dr, Lewes

Listing courtesy of EXP Realty, LLC. Contact: 8885434829

$1,585,000

6 Beds ⋅ 5 Baths

Discover exceptional new construction by Evergreene Homes in the prestigious Olde Town community. This beautifully designed 5-bedroom, 4.5-bath home offers 3,940 square feet of thoughtfully planned living space, blending luxury, comfort, and flexibility. The main-level owner’s suite provides a private retreat and the convenience of first-floor living, while the second level features additional bedrooms and a large bonus room ideal for a media room, home office, playroom, or additional lounge. An expansive unfinished basement offers incredible potential for future living space, recreation, a home gym, or abundant storage. A large two-car garage provides plenty of room for vehicles, bikes, and beach gear, while the beautiful rear screened porch creates the perfect setting for relaxing, dining, and enjoying the coastal breeze. Located within walking distance of the community pool and Lewes Public Library, the home also offers easy access to the Junction & Breakwater Trail for miles of hiking and biking. With spacious interiors, exceptional indoor-outdoor living, and a sought-after location close to the best of Lewes, this remarkable Olde Town home is an opportunity not to be missed. The staged photos are virtually staged and do not represent furniture or inclusions in the home as they are purely for illustrative purposes only.

65 Filly Ln, Lewes

Listing courtesy of Compass. Contact: 3022734998

$2,499,000

6 Beds ⋅ 5 Baths

THE ULTIMATE COASTAL SANCTUARY! Welcome to a true masterpiece of modern seaside architecture in Anglers Nest! This meticulously designed 6-bedroom home offers an unparalleled lifestyle where panoramic vistas of the canal, salt marshes, and bay serve as your daily backdrop. The heart of the residence is the breathtaking top-floor great room, featuring soaring vaulted ceilings, luxury vinyl plank flooring, and a floor-to-ceiling shiplap fireplace. The gourmet chef’s kitchen is a showstopper, anchored by a massive quartz island and equipped with premium stainless steel appliances, and custom backsplash. Seamless indoor-outdoor living is achieved through expansive sliding glass doors that open to a large, covered balcony, perfect for watching the boats return to the harbor. The thoughtful layout provides ample space for family and guests, highlighted by multiple primary-style suites with spa-inspired bathrooms. Additional amenities include a mid-level office, wet bar with beverage fridge, multiple balconies, screen porch, patio, outdoor shower, hot tub, first floor flex room, and a soft, airy coastal palette throughout. Perfectly positioned just steps from the tranquil Bay Beach and seconds from the docks of the Lewes Rehoboth Canal, and historic downtown Lewes, this home represents a rare opportunity to own a front-row seat to the best of the Delaware coast.

216 Grey Plover Ct, Lewes

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

$799,900

5 Beds ⋅ 3 Baths

LEWES LIVING is yours from this in-town, beautifully appointed home in Pilottown Village! Enjoy the perfect blend of charm & modern elegance with beautiful hardwood flooring throughout the first level. The spacious living room with gas fireplace provides a warm ambiance for entertaining or relaxing. The bright screened porch floods the space with natural light, offering a peaceful retreat to enjoy your morning coffee. The primary suite offers excellent privacy with en-suite bath and set apart from the 3 additional first level bedrooms. The second level offers a versatile 5th bedroom with private bath. Nestled in vibrant Pilottown Village, enjoy easy access to downtown shops, dining, and entertainment, as well as the beautiful beaches that make Lewes a sought-after destination. Don’t miss the opportunity to make this exceptional property your new home. Schedule a tour and experience the unparalleled charm of this in-town Lewes gem!

1 Flamingo Ct, Lewes

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

$1,199,900

5 Beds ⋅ 4 Baths

Rare Investment Opportunity in the Heart of Historic Lewes! Opportunities like this do not come around often. Nestled on a quiet street in the highly coveted Historic District of Lewes, this 3-unit property offers the perfect blend of historic charm and investment potential. Whether you are looking for a lucrative addition to your portfolio, a multi-generational family compound, or a "live in one unit, rent the other two" house-hacking strategy, this home delivers. Unit1 features 3 bedrooms, 2 baths, kitchen, formal dining room, living room and large roof top deck. Unit 2 features a first floor entrance, an open living and dining room, a kitchen, a large bedroom, and a full bath. The 3rd unit offers an eat-in kitchen, bright living room, bedroom, full bath, and garage access. The full basement offers plenty of storage space. Don't miss this unbeatable location, just steps away from Second Street’s award-winning dining, boutique shopping, and the Lewes Farmers Market and a short bike ride to Lewes Beach and Cape Henlopen State Park. Call today!

338 Market St, Lewes

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

$500,000

6 Beds ⋅ 3 Baths

Imagine the ultimate coastal restoration project in Lewes, Delaware: a sprawling, six-bedroom colonial canvas on a prime 0.44-acre lot, waiting for a talented visionary or investor to breathe new life into its impressive bones. Nestled in the highly coveted neighborhood of Edgewater Estates near the scenic waters of Red Mill Pond, 30849 Buttonwood Drive stands as a monumental opportunity in the award-winning Cape Henlopen School District. With an expansive 2,838 finished square feet of living space, this home is rough around the edges and sold strictly in as-is condition, but it is primed for a stunning transformation that will yield exceptional long-term upside. Step past the classic façade and design a masterpiece: the main floor features a highly functional traditional layout with a formal dining room, country kitchen, light-filled breakfast nook, first-floor laundry room, and a highly desirable main-level primary bedroom suite. Upstairs, discover additional generously sized bedrooms, a dedicated craft room/photo lab space, and a massive walk-in attic offering superb storage or further customization potential. While the property requires a complete interior cosmetic overhaul, a new rear deck, and exterior repainting, the most expensive mechanical heavy-lifting is already done, anchored by two high-efficiency Lennox HVAC heat pump zones installed in 2020 and 2021. Outside, the premium lot accommodates an attached side-entry two-car garage, mature trees, and a spacious backyard ready for custom landscaping. Located just minutes from historic downtown Lewes, pristine Cape Henlopen State Park beaches, tax-free retail shopping, and popular local boating access, this fixer-upper is the perfect entry point to the Delaware coastal market for DIY homeowners and experienced flippers alike. Bring your contractor, unlock the immense equity hidden within this grand structure, and draft the next chapter of this coastal Lewes estate! Please note that active, working security cameras are present on-site.

30849 Buttonwood Dr, Lewes

Listing courtesy of Keller Williams Realty Central-Delaware. Contact: 3026770020

$1,999,900

5 Beds ⋅ 5 Baths

New Price!!! COASTAL SOPHISTICATION MEETS POND-SIDE SERENITY IN SHOWFIELD. Situated in the highly sought-after community of Showfield, this exceptional Chesapeake model by Schell Brothers offers luxury coastal living just moments from downtown Lewes, scenic trails, beaches, shopping, and dining. Perfectly positioned with a tranquil pond setting in the rear, the home enjoys added privacy and open space between neighboring properties. Designed with both comfort and entertaining in mind, this spacious home features 5 bedrooms across the first and second floors, including a first-floor primary suite and an additional first-floor guest suite, plus a private first-floor office/flex room and a beautifully finished basement providing abundant living and recreational space. Extensive custom upgrades elevate this home throughout, including engineered hardwood flooring with wider planks across the entire first level, expanded bump-outs, an upgraded kitchen backsplash, and an expanded driveway. The inviting front porch was thoughtfully redesigned from a traditional Trex-style porch with PVC railings into an elegant open concrete and stone porch that enhances the home’s curb appeal. Outdoor living is truly extraordinary with professionally designed extravagant landscaping, bluestone walkways in both the front and rear, and a stunning bluestone patio anchored by a custom stacked-stone fireplace featuring symmetrical wood storage alcoves, a large tapered chimney, and a built-in natural gas grill — creating the ultimate outdoor entertaining space. Residents of Showfield enjoy access to a beautifully appointed clubhouse offering numerous opportunities for social gatherings, activities, and community events, all within one of Lewes’ most desirable and walkable neighborhoods.

35142 Battlemixer Dr, Lewes

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

$1,999,999

5 Beds ⋅ 4 Baths

Properties like 29 Bridle Ridge Circle don’t come along often! This extraordinary 5,642-square-foot home features 5 bedrooms, 4 full bathrooms, a thoughtfully designed floor plan, and curb appeal straight from a magazine. Custom millwork graces every room in this home, including on the ceilings! The fully redesigned kitchen is the heart of the home, updated just a few years ago with the finishes and function you’ll fall in love with. Featuring updated millwork, white cabinets, custom tile backsplash, a large center island with storage and seating, and stainless steel appliances, this kitchen was designed for cooking and entertaining. A separate bar with storage and a wine fridge gives you even more space. Just off the kitchen, you’ll find a well-equipped laundry room with beautiful glass doors, tile backsplash, and loads of counter and cabinet space. Next to the laundry room is a spacious pantry with double doors. The kitchen opens into a large living space with an eye-catching fireplace surrounded by wooden accents and built-in storage. A wall of windows makes the space feel open, bright, and sunny. Just off the kitchen is a large sunroom with beautiful windows overlooking the backyard. A spacious sun porch with brick flooring and custom removable windows provides the perfect place to relax or entertain. The sun porch opens to your very own backyard oasis with an in-ground Anthony Sylvan concrete pool and a cabana pool house with a full bathroom. You’ll feel like you’re on vacation every day! Back inside the home, you’ll find a luxurious primary suite that feels like a relaxing escape, complete with a geothermal unit for comfort and a spa-worthy bathroom with heated marble floors, a stand-alone tub, and a walk-in tiled shower with multiple shower heads and a tile bench. Redesigned just three years ago, every morning here feels like a retreat! Three-zone geothermal units allow everyone to relax at their own comfort level. On the second floor, you’ll find 3 more beautifully-appointed bedrooms, complete with custom millwork and large windows, and 2 updated bathrooms. A bonus room, attic, and loft overlooking the living space complete this luxurious second floor. The fully finished lower level is a basement truly built for living! Here you’ll find a dedicated home gym, a half-bath, a conditioned mechanical room, and multiple storage spaces to keep everything organized and accessible. The home also features a 1,700-square-foot, finished and heated barn, ideal for a workshop, studio, entertainment space, home office, or hobby haven – whatever your heart desires! Nestled in the popular Lewes community of the Estates at Bridge Ridge, this unbelievable home offers the perfect blend of peaceful living with coastal access. Just minutes from Route 1 shopping and dining, Lewes Beach, Cape Henlopen State Park, and downtown Rehoboth Beach, it’s luxurious living at its finest. Whether you’re looking for a full-time residence or the ultimate Sussex County beach retreat, 29 Bridle Ridge Circle delivers on every level. If you’ve been waiting for something extraordinary, this very well could be the one. Schedule your private showing of this remarkable property today!

29 Bridle Ridge Cir, Lewes

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

$899,000

5 Beds ⋅ 4 Baths

Tucked away in one of Lewes’ most desirable luxury communities, this exceptional bayside abode offers a rare blend of thoughtful design, modern efficiency, and elevated coastal living. Built by Insight Homes—renowned as the #1 Green Energy Builder—this impressive 4,000-square-foot residence goes far beyond new construction, as its current owners have meticulously enhanced every inch with warmth, sophistication, and high-end finishes including Subzero and Wolfe appliances. From the moment you step inside, the expansive, open-concept floor plan welcomes you with light-filled living spaces designed for both comfort and entertaining. The first-floor owner’s suite is a private retreat, offering convenience and serenity, while the stunning four-season room invites year-round enjoyment with tranquil views of lush gardens and professionally designed natural landscaping. Step outside and discover a true backyard oasis—complete with an outdoor kitchen and beautifully curated spaces that seamlessly blend indoor and outdoor living. Whether hosting gatherings or enjoying a quiet morning coffee, this setting is simply unmatched. Upstairs, the home continues to impress with a versatile second living area perfect for relaxing or entertaining guests, along with a spacious craft room or optional fifth bedroom. An additional suite provides comfort and privacy for visitors, while the expansive finished storage room offers incredible flexibility for hobbies, organization, or future customization. Set within a sought-after community known for its luxury lifestyle and abundant amenities, this home offers not just a residence—but a refined coastal experience. Enjoy access to resort-style features, beautifully maintained surroundings, and the charm that makes Lewes one of Delaware’s most coveted destinations. Don’t forget the Outdoor Kitchen and Hardscaping on this premium wooded lot. This is more than a home—it’s a statement of living well by the bay.

34579 Addyson Ct, Lewes

Listing courtesy of Dave McCarthy & Associates, Inc.. Contact: 3024262080

$3,750,000

5 Beds ⋅ 6 Baths

ARCHITECTURAL ARTISTRY MEETS COASTAL TRANQUILITY in THE NEST - a private, gated enclave within the highly sought-after Hawkseye Community. Experience the pinnacle of coastal living from this stunning residence that's an architectural masterpiece, where contemporary farmhouse aesthetics converge with high-design luxury. From the sweeping circular drive, to the soaring silhouette, the home makes a monumental first impression. Step through grand double doors into a breathtaking two-story great room where floor-to-ceiling windows invites the outdoors in, anchored by a magnificent two-sided stone fireplace that leads to a sophisticated formal dining room. This is a masterclass in scale and craftsmanship, offering a seamless flow designed for both grand-scale entertaining and intimate relaxation. The culinary center is a true showstopper, featuring professional-grade Thermador appliances, including a six-burner gas cooktop, four wall ovens, dual warming drawers, and dual dishwashers, complemented by oversized refrigerator, a wine fridge, and expansive quartz countertops. The main-level primary sanctuary offers ultimate seclusion, complete with a custom-designed dressing suite, spa-inspired ensuite bath, and private laundry. An industrial custom staircase leads to the upper level, where a magnificent suspended walkway bridges two distinct wings. This floor hosts three generous guest suites, a private executive office, and an expansive family lounge with a gas fireplace that easily serves as a fifth bedroom. The resort-style exterior delivers an unparalleled outdoor oasis, featuring a screened porch with a stone fireplace, an expansive designer patio, and a heated in-ground pool equipped with Smart Pool Automation. The two-acre grounds are professionally landscaped for total privacy and supported by a private well for cost-effective irrigation. Additional highlights include a three-car garage, a four-zone HVAC system, and a massive unfinished basement with plumbing rough-ins ready for future expansion. Located steps from the Junction-Breakwater Trail and minutes from Cape Henlopen State Park and downtown Lewes, this property offers the best of the Delaware coast. Make 2026 the year you make this coastal oasis yours!

35975 Goshawk Ct, Lewes

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

$1,550,000

5 Beds ⋅ 4 Baths

MODERN MASTERPIECE IN HISTORIC LEWES! Experience the perfect harmony of 19th-century charm, and sleek, contemporary luxury. Located in the very heart of Lewes, this stunningly renovated historic home offers a rare "best of both worlds" lifestyle just steps from iconic downtown shops and a short breeze away from the beach. Home delivers a sophisticated coastal lifestyle across 5 bedrooms and 4 luxury baths. The layout is thoughtfully designed for effortless living, featuring both first and second-floor owner’s suites and expansive, sun-drenched gathering spaces. At the center of it all is a gourmet kitchen that serves as the home's crowning jewel, fully remodeled with sparkling new appliances, elegant stone countertops, a double wall oven, and designer cabinetry. The seamless flow continues into the formal dining area, highlighted by industrial-chic lighting, and a cozy family room centered around a crisp white fireplace and custom built-ins. Throughout the home, spa-like bathrooms feature massive glass-enclosed showers and contemporary vanities that provide a high-end retreat for guests and owners alike. This private sanctuary extends to the outdoors, where you can enjoy a massive screened porch and a fully fenced yard complete with a relaxing hot tub and a historic outbuilding. Rare off-street parking in the center of town completes this exceptional package, allowing you to enjoy the very best of Historic Lewes and the beach! Call Today!

211 W 4th St, Lewes

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

$2,670,000

5 Beds ⋅ 7 Baths

32059 Conleys Chapel Road is simply in a class of its own! This unbelievably beautiful coastal estate sits on nine private acres with a wooded backdrop, meticulously manicured gardens, hardscaping, and lighted natural ponds with fountains. Close to Lewes and Rehoboth Beach, this estate is an unmatched blend of refined country living and a laid-back coastal lifestyle. Inside, you’ll find 4-5 bedrooms, each with an ensuite bathroom, spread across three thoughtfully designed levels and accessible by elevator. A chef’s kitchen is the anchor of the home with English cabinetry by renowned designer Mark Wilkinson, Italian marble tile, a glass vaulted ceiling, gas and induction cooktops, a steam oven, and an expansive butler’s pantry – all perfect for effortless entertaining! The home also features four fireplaces, formal living and dining rooms, rich hardwood floors, and architectural trim, weaving craftsmanship and style throughout every room. The second floor features a primary suite with a sitting room, a large bathroom, and a spacious walk-in closet, as well as three additional bedrooms with wood flooring and architectural trim. The third floor features a large guest suite with an open-air bathtub and plenty of flexible spaces, perfect for private offices, additional bedrooms, a yoga/exercise room, a playroom, or more! The indoor heated lap pool, with cathedral ceilings, skylights, a full bath, a wine refrigerator, and multiple lounge areas, brings a touch of resort-like style to an already impressive estate. A second laundry area is located near the pool, making clean-up easy! Outside, a hot tub, firepit, and horse-ready acreage round out the estate. An attached two-car garage, detached three-car garage, two-zone geothermal HVAC, a full irrigation system, and a carriage house with conversion potential complete the property. For those looking for an exquisite estate nestled in beautiful Sussex County, 32059 Conleys Chapel Road is a dream!

32059 Conleys Chapel Rd, Lewes

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

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