Explore Lewes, DE Homes for Sale

Homes for Sale with a Guest House in Lewes, DE

Welcome to your dedicated resource for homes for sale with a guest house in Lewes, DE. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Lewes, DE agent, Coastal Homestead Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a guest house properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Guest House in Lewes, DE

17049 Oak Ct, Lewes
$535,000
3 Beds ⋅ 2 Baths
Character, Nature, and a Boat Launch Across the Street in Edgewater Estates Some homes just feel settled, and this 3-bedroom, 2-bath Lewes charmer is one of them. Set in well-established Edgewater Estates, it offers the warmth and character that newer builds simply can’t copy, along with a lovely yard and a location that puts the best of coastal Delaware at your doorstep. A yard made for slowing down Mature trees shade the property and give the yard a sense of privacy and calm that only years of growth can create. It’s the perfect setting for gardening, backyard gatherings, or simply enjoying the changing seasons. Songbirds, rustling leaves, and dappled afternoon light make this a true retreat from the summer crowds. The porch you’ll live on The inviting porch will quickly become your favorite room. Start the day with coffee as the neighborhood wakes up, then return in the evening to unwind with a glass of wine and nothing but the sound of the breeze through the trees. Quiet evenings like these are exactly why people fall in love with Lewes. Life on the water The boat launch sits right across the street, so spontaneous days on the water are part of everyday life. Fish for flounder, paddle the creeks, or cruise out toward Cape Henlopen without trailering across town. Boaters, kayakers, and anglers will appreciate just how rare this convenience is. Comfortable living with character Inside, three bedrooms and two full baths provide room for family, visiting friends, or a home office. The home’s character shines throughout, offering a cozy, welcoming feel whether you’re looking for a full-time residence, a weekend getaway, or a place to retire by the coast. The best of Lewes and Rehoboth Enjoy the charm of historic downtown Lewes, with its shops, galleries, and acclaimed restaurants along Second Street, plus the sand and calm bay waters of Lewes Beach. Rehoboth’s tax-free outlet shopping, boardwalk, and lively dining scene are an easy drive away. Local favorites like Big Oyster Brewery, Crooked Hammock, and Dogfish Head are close by, along with farm-to-table cafés and fresh seafood spots. Cape Henlopen State Park and the Junction & Breakwater Trail offer miles of hiking, biking, and beaches to explore. Low HOA, high quality of life With low HOA fees, you get the comfort of an established community without the heavy costs often found in newer developments. A character-filled home, a peaceful tree-shaded setting, and the water right across the street. Opportunities like this in Edgewater Estates don’t come along often. Schedule your private showing today.

17049 Oak Ct, Lewes

Listing courtesy of Iron Valley Real Estate Premier. Contact:

23925 Sunny Cove Ct, Lewes
$2,599,000
4 Beds ⋅ 5 Baths
An extraordinary waterfront setting, captivating architectural design, and an exceptional collection of resort-inspired amenities define this distinctive coastal residence in the Villages at Herring Creek. Perfectly positioned along a scenic stretch of shoreline, this remarkable European-inspired property captures sweeping panoramic water views and offers an unparalleled opportunity to enjoy the very best of Delaware's coastal lifestyle! Featuring a private dock, boat lift, expansive saltwater pool and spa, and beautifully designed outdoor entertaining spaces. From its picturesque waterfront setting to its thoughtfully landscaped grounds using travertine stone and pavers, the property offers a rare combination of privacy, natural beauty, and exceptional recreational opportunities. Inside, an impressive foyer introduces a thoughtfully designed residence distinguished by soaring ceilings, graceful architectural details, and an inviting floor plan that seamlessly connects its interior living spaces with the spectacular waterfront surroundings. Expansive windows and glass doors frame captivating water views, while Brazilian cherry hardwood flooring, elegant wainscoting, and distinctive ceiling treatments contribute warmth, character, and timeless sophistication throughout the home. At the heart of the residence, the beautifully appointed gourmet kitchen combines refined craftsmanship with exceptional functionality. Custom cabinetry, granite countertops, a generous center island, and premium appliances, including a Sub-Zero refrigerator and Wolf cooking appliances, create an inviting setting for both everyday living and entertaining. A dramatic vaulted ceiling and expansive waterfront windows enhance the kitchen's open, airy atmosphere, while adjoining gathering spaces provide effortless access to the outdoor terraces, pool, and waterfront beyond. The home's thoughtfully designed living areas offer an exceptional balance of grand entertaining spaces and intimate retreats. A dramatic living room with soaring ceilings, elegant architectural windows, and French doors welcomes abundant natural light, while additional sitting and gathering areas offer comfortable spaces to relax and enjoy the surrounding scenery. The sun-filled waterfront sitting room, surrounded by expansive windows, provides an especially inviting vantage point from which to appreciate the property's peaceful setting and ever-changing water views. The first-floor primary suite offers a private and luxurious retreat, featuring an inviting sitting area, a distinctive pass-through fireplace, and a beautifully appointed bath with a soaking tub and steam shower. Equally impressive are the property's exceptional outdoor living and entertaining spaces. An expansive saltwater swimming pool and adjoining spa serve as the centerpiece of a spectacular waterfront retreat, complemented by generous stone terraces, beautifully maintained gardens, and a charming poolside cabana. Designed for both relaxation and entertaining, these outdoor spaces provide an extraordinary setting for afternoon gatherings, al fresco dining, and peaceful evenings overlooking the water. For boating enthusiasts, the property offers an exceptional opportunity to enjoy the waterways of coastal Delaware directly from home. A private, extended waterfront dock with multiple boat slips, a boat lift, and dockside water and electrical service provides convenient access to the Rehoboth Bay. From leisurely sunset cruises and waterfront dining to fishing, watersports, and gatherings at nearby sandbars, the surrounding waterways offer an abundance of recreational possibilities. Beyond the property's exceptional private features, residents of the Villages at Herring Creek enjoy access to community amenities including a clubhouse, fitness center, and swimming pool. Close to desirable locations including downtown Lewes, Rehoboth Beach, coastal dining, shopping, beaches, and recreational destinations.

23925 Sunny Cove Ct, Lewes

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

33227 Cherry Ct, Lewes
$369,900
3 Beds ⋅ 2 Baths
Charming Coastal Retreat on Cherry Court – Big on Space, Style & Outdoor Living! This home packs a lot of punch! Excellent value, fantastic location, and an incredible use of indoor and outdoor living space! Tucked away on a quiet cul-de-sac in the highly desirable, amenity-rich community of Angola by the Bay, this charming 3-bedroom, 2-full-bath coastal retreat is just two blocks from the water and two blocks from the community pool. This home is ready for you to start enjoying the coastal lifestyle! Step inside and you'll immediately appreciate the soaring vaulted ceilings, dramatic floor-to-ceiling windows, and open-concept design that fills the home with natural light. The spacious living, dining, and kitchen areas flow effortlessly together, making the most of every square foot. Two main-level bedrooms, including an updated primary bedroom and bathroom, provide comfortable accommodations, while the expansive loft serves as a versatile third bedroom with plenty of sleeping space for family and guests. Whether hosting a weekend getaway or gathering the whole crew, there's room for everyone! Abundant closet space adds even more functionality to this thoughtfully designed home. The outdoor living spaces are where this property really shines! Extensive, beautifully designed paver patios create multiple areas for dining, lounging, grilling, and entertaining, all with the added benefit of low-maintenance upkeep. Every inch of the outdoor space has been thoughtfully utilized, offering plenty of seating and room to relax without the burden of extensive yard maintenance. Enjoy morning coffee in the sunshine, afternoon cookouts, or evenings gathered around the fire pit. The screened outdoor entertaining room, complete with a television and overlooking the fire pit area, adds yet another fantastic gathering space! It's the perfect spot for watching the game, relaxing with friends, or enjoying a coastal evening. Additional detached storage shed, two driveways offering ample parking, and attractive landscaping. Located in the sought-after waterfront community of Angola by the Bay, residents enjoy access to a community pool, marina, boat ramp, fishing and crabbing piers, walking trails, and numerous recreational amenities, all just minutes from the beaches, shopping, dining, and attractions of Lewes and Rehoboth Beach. Big on charm, big on entertaining space, and big on value! Whether you're searching for a full-time residence, weekend escape, or coastal getaway, this furnished Cherry Court retreat offers an exceptional opportunity to enjoy the best of beach-area living. Come see just how much this home has to offer! Many items will convey please ask for list of exclusions.

33227 Cherry Ct, Lewes

Listing courtesy of Tesla Realty Group, LLC. Contact:

33884 Mc Nicol Rd, Lewes
$150,000
4 Beds ⋅ 3 Baths
Welcome to 33884 McNicol Road, affectionately known as "The Shack," a charming coastal retreat with plenty of personality, ideally located east of Route 1 in the desirable McNicol Place community. Beautifully updated and being sold furnished with minor exclusions, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of coastal charm, modern improvements, and relaxed beach living. Situated just under three miles from Lewes Beach and the shops and restaurants of historic downtown Lewes, this exceptional location makes it easy to hop on your bike and enjoy everything this beloved coastal town has to offer. The Cape May-Lewes Ferry and Cape Henlopen State Park are also nearby, providing endless opportunities for outdoor recreation and exploration. Thoughtfully expanded in 2022, the home features a spacious addition that includes a light-filled living room with a soaring vaulted ceiling and a generously sized primary bedroom with a private ensuite bath. This well-designed addition creates a comfortable retreat while providing expanded living and entertaining spaces, ideal for gathering with family and friends. Luxury vinyl plank flooring flows throughout the main living areas, offering both style and easy maintenance. At the heart of the home, the beautifully updated kitchen combines functionality with coastal appeal. Featuring newer stainless-steel appliances (conveying as-is), a gas range, and a double pantry offering abundant storage, this inviting space is designed for everyday convenience. A dedicated coffee bar with beverage refrigerator adds a thoughtful touch, perfect for preparing your morning coffee before heading to the beach or keeping refreshments close at hand when entertaining. Adding to the home's turnkey appeal, the kitchen comes fully stocked with place settings for eight, along with pots, pans, and other kitchen essentials, making it easy to settle in and start enjoying beach life from day one. The family room offers another welcoming gathering space, highlighted by a charming shiplap accent wall that complements the home's relaxed coastal character. Three additional bedrooms are located on the opposite side of the home, providing a comfortable separation from the primary suite. One of these bedrooms enjoys the added convenience of its own powder room, while an updated, full hall bath with a dual sink vanity serves this area. A separate laundry room with a full-size washer and dryer adds everyday practicality. Outdoor living is equally inviting, with multiple spaces designed for relaxing and entertaining. A welcoming front entry deck sets the tone, while a side deck with privacy panels provides a comfortable setting for outdoor dining or simply unwinding after a day at the beach. A dedicated stone-covered outdoor gathering area offers the perfect spot for grilling, gathering around a fire pit, or enjoying evenings under the stars. The yard provides additional space for a friendly game of cornhole or horseshoes, making it easy to embrace the laid-back coastal lifestyle. Additional improvements and conveniences include a tin roof (2022) covering the entire structure, an outdoor shower for rinsing off after sandy beach days, and a storage shed offering plenty of room for beach chairs, bicycles, and gardening essentials. Whether you're looking for a weekend getaway, seasonal retreat, or a place to enjoy coastal living throughout the year, "The Shack" offers a wonderful opportunity to settle into the Lewes lifestyle. Enjoy the quieter off-season months, then welcome the excitement of summer when Memorial Day arrives. With its desirable east-of-Route-1 location, thoughtful updates, flexible living spaces, and furnishings included with minor exclusions, this charming home is ready for its next chapter.

33884 Mc Nicol Rd, Lewes

Listing courtesy of Northrop Realty. Contact:

31100 Tigress Rd, Lewes
$499,000
3 Beds ⋅ 2 Baths
Welcome to coastal living at its finest in the sought-after community of Headwater Cove in Lewes, Delaware. This beautifully designed 3-bedroom, 2-bathroom, 2-car garage home spans 2,070 square feet of living space. Perfectly blending style, comfort, and convenience, the interior features durable, low-maintenance luxury vinyl plank (LVP) flooring throughout, framed by decorative wood trim and crown molding that add a layer of sophisticated elegance to every room. At the heart of the home, the chef-inspired kitchen features sleek quartz countertops and premium stainless steel appliances, making daily meal preparation and entertaining an absolute breeze. Step outside to your private outdoor living space with screen in patio—complete with a fully fenced backyard and a deck designed for relaxation. Enjoy serene, uninterrupted views of the community pond and fountain, offering the ultimate backdrop for unwind on warm summer nights. ​Take full advantage of the vibrant neighborhood clubhouse, featuring a sparkling outdoor pool, fully equipped fitness center, and inviting gathering spaces for social events and gatherings. ​Prime Coastal Location: A short drive away from downtown Lewes, pristine Delaware beaches, tax-free outlet shopping, and top-tier dining. ​Whether you are looking for a full-time residence or a refined beach retreat, this Headwater Cove gem offers the complete coastal Delaware lifestyle. THIRD PARTY PROCESSOR REQUIRED. SEE ATTACHED DISCLOSURES THAT MUST BE SIGNED AND PRESENTED WITH ALL OFFERS. All offers are subject to 3rd party mortgage company approval and subject to the Seller(s) acceptance of those approval terms. Property is being sold as-is with no warranties expressed or implied. Home inspections are for informational purposes only. Buyer may be responsible for any of their own lender required repairs.

31100 Tigress Rd, Lewes

Listing courtesy of Patterson-Schwartz-Rehoboth. Contact:

1006 Heron Ct, Lewes
$989,900
4 Beds ⋅ 4 Baths
Are you looking for a new home? Why wait to Build when this gorgeous custom new home awaits you in Lewes just minutes to everything! Welcome to 1006 Heron Ct a custom built home and experience luxurious coastal living at its best. Custom Builder SunRen Homes has thoughtfully curated every space to deliver timeless style, comfort, and functionality. This custom-crafted residence is no cookie-cutter track builder home, it is designed with exceptional attention to detail and elevated finishes throughout. Featuring 4 bedrooms, 3.5 bathrooms, and situated on a spacious 1 acre lot, this property offers the perfect blend of luxury and lifestyle. Imagine mornings in your designer kitchen featuring premium Café appliances, afternoons entertaining from the stunning butler’s pantry on your spacious composite back deck, and evenings relaxing in beautifully designed living spaces accented by high-end modern lighting, custom details, and upscale finishes throughout. The first floor owner’s suite is a true retreat, showcasing elegant crown molding, spa-inspired finishes, and not one—but two custom walk-in closets complete with built-in closet systems. Every room reflects the craftsmanship and elevated design that has come to be synonymous with SunRen Homes while the Oak wood staircases with striking black open railings create a dramatic architectural focal point. The Gourmet kitchen is a chef's dream with custom two tone soft close cabinets, gorgeous quartz counters, an enormous island to entertain your family and friends, new Cafe' appliances, elegant modern light fixtures, and exquisite tile backsplash. Upstairs features a spacious loft, a second main bedroom as well as 2 additional bedrooms and guest bathroom. The New Dual-zoned HVAC ensures your year-round comfort. Step outside into your dream backyard oasis and explore endless possibilities, from custom inground pools and pool houses to fully equipped outdoor kitchens and beyond. At 1006 Heron Ct you experience not only low Delaware property taxes, but also minimal HOA fees with a total peace of mind in your newly completed luxury home set in premier Lewes location. Here you are located just minutes to all that the Lewes-Rehoboth Corridor has to offer from beaches, boardwalk, the Cape Henlopen State Park, fishing piers, marinas, your favorite local restaurants, outlet shopping, and so much more. Schedule your private tour today and don't miss your opportunity to own a truly one-of-a-kind coastal luxury home built by SunRen Homes.

1006 Heron Ct, Lewes

Listing courtesy of RE/MAX Associates. Contact:

18349 Josephs Rd, Lewes
$749,900
5 Beds ⋅ 4 Baths
COMPLETELY REBUILT FROM THE FOUNDATION UP IN 2024 + DIRECT ACCESS TO THE LEWES-GEORGETOWN BIKE TRAIL + PRIVATE IN-LAW SUITE! Discover an exceptional opportunity in Lewes, Delaware, where the appeal of a brand-new home meets flexible living spaces and an incredible location. This is not simply a renovation—this home was completely rebuilt in 2024, with the original foundation being the ONLY remaining component of the previous structure. Everything above the foundation is brand new, including the entire electrical and plumbing systems, along with a brand-new well. Thoughtfully reconstructed from the ground up, this home offers the comfort, quality, and appeal of new construction in a peaceful setting surrounded by mature trees. Step inside to discover entirely new interiors featuring bright, inviting living spaces, a fresh modern aesthetic, neutral finishes, beautiful new flooring, recessed lighting, and abundant natural light. Every detail reflects the home's complete transformation, from the newly constructed living areas to the brand-new kitchens and bathrooms. Stylish cabinetry, attractive countertops, contemporary fixtures, and thoughtfully selected finishes create a cohesive, move-in-ready environment designed for modern living. With virtually everything newly built and installed in 2024, this home offers far more than cosmetic improvements or traditional updates. One of the property's most distinctive features is its private in-law suite, offering exceptional flexibility for a variety of living arrangements. Complete with its own entrance, dedicated parking, separate electric meter, kitchen, and living spaces, this self-contained retreat provides an ideal setup for extended guests, multigenerational living, or other potential uses. The separation between living areas offers added privacy and independence without sacrificing the convenience of being under one roof. Situated on a generous 0.4-acre lot, the property offers an inviting outdoor setting surrounded by mature trees and natural beauty. Enjoy plenty of space to relax, entertain, and take in the fresh air, with a spacious deck and covered porch providing additional opportunities to unwind. With direct access to the Lewes-Georgetown Bike Trail, walking, biking, and exploring the scenic surroundings can become part of your everyday routine. Enjoy convenient access to downtown Lewes, local restaurants, shopping, and the beautiful Delaware Beaches, all while returning home to a peaceful setting that feels tucked away. Whether you're looking for a primary residence, a vacation retreat, or a property offering versatile living possibilities, this exceptional Lewes home delivers a combination of 2024 new construction above the existing foundation, entirely new essential systems, independent living accommodations, and direct trail access. With virtually every component of the home newly constructed, including its electrical and plumbing systems and private well, this property offers the opportunity to enjoy the benefits of a newly built home in an established Coastal Delaware setting. Completely reimagined, entirely rebuilt, and ready for its next chapter—this is Lewes living with a fresh start!

18349 Josephs Rd, Lewes

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

18 Applewood Ln, Lewes
$595,000
4 Beds ⋅ 3 Baths
Welcome to this beautifully updated Colonial in the desirable, established community of Chapel Green, where timeless charm meets modern comfort. Offering four spacious bedrooms, 2.5 bathrooms, and an inviting open floor plan, this home is thoughtfully designed for both everyday living and entertaining. At the heart of the home is the gourmet kitchen, remodeled in 2021 with upgraded cabinetry and countertops and enhanced with updated appliances. The kitchen flows seamlessly into the breakfast area and adjoining living spaces, creating a warm and welcoming atmosphere for family gatherings and entertaining. The great room features a cozy gas fireplace, while the screened porch offers a peaceful retreat overlooking the beautifully landscaped grounds. First floor spacious primary suite is a true retreat, featuring an elegant tray ceiling, ceiling fan, walk-in closet, and a completely remodeled en-suite bathroom completed in 2020. The second-floor bathroom was also remodeled in 2024. Additional interior updates include new flooring throughout the first floor, staircase, and upstairs landing, completed in 2021. The home’s extensive improvements continue outdoors, where you’ll find a fully fenced backyard designed for relaxation and enjoyment. The outdoor space features a screened porch, a concrete patio with a decorative stamped border completed in 2024, a pergola, a storage shed, and beautifully maintained landscaping. Whether you’re hosting a summer barbecue, enjoying your morning coffee, or simply unwinding at the end of the day, this backyard offers plenty of room to enjoy the outdoors. Front and rear lawn irrigation was installed in 2025, and new fencing was added in 2023. Numerous additional upgrades provide comfort, convenience, and peace of mind, including a new roof, skylights, and gutters in 2024; a new hot water heater in 2024; and a new front door, complemented by new front steps and a stamped concrete walkway, also completed in 2024. Completing the property is a two-car garage and an ample driveway offering plenty of parking for residents and guests alike. Beyond the home, Chapel Green offers an inviting community atmosphere with an outdoor swimming pool and community center, providing wonderful opportunities to relax and connect with neighbors. Conveniently located near Delaware’s beautiful beaches, golf courses, shopping, dining, and everyday amenities, this home combines an established neighborhood setting with easy access to everything the area has to offer. With its classic Colonial appeal, extensive updates, inviting indoor and outdoor living spaces, and desirable community amenities, this Chapel Green home is ready to welcome its next owners.

18 Applewood Ln, Lewes

Listing courtesy of BURTON REALTY INC. Contact:

31143 Tigress Rd, Lewes
$558,900
3 Beds ⋅ 4 Baths
WHY WAIT FOR NEW CONSTRUCTION WHEN YOU CAN MOVE RIGHT IN? This beautifully maintained, like-new Wheaton model offers over 2,500 square feet of spacious single-level living, featuring 3 bedrooms, 3.5 baths, a 3-car garage, and a desirable corner lot located in the Cape Henlopen School District. The welcoming foyer opens to a spacious guest bedroom with a large closet and adjacent full bath. A light-filled flex room provides the perfect space for a home office or additional living area. Down the hall, you'll find a convenient half bath, laundry room, and a second guest bedroom complete with an en-suite bath and walk-in closet. The open-concept great room features a tray ceiling and flows seamlessly into the beautifully appointed kitchen, showcasing an oversized island, quartz countertops, modern gray cabinetry, stainless steel appliances, and an oversized pantry. The adjoining dining area offers plenty of room for entertainment. Privately situated at the rear of the home, the owner's suite serves as a relaxing retreat with a tray ceiling, spacious bath featuring a double vanity and private water closet, and two walk-in closets. Enjoy outdoor living on the covered rear porch. Smart home features include a Wi-Fi-enabled thermostat, doorbell, and garage door opener. The HOA adds exceptional value with lawn care, trash service included. Located in the sought-after Headwater Cove community, residents enjoy outstanding amenities, including a clubhouse, fitness center, pickleball courts, and an outdoor in-ground pool. Sidewalk-lined streets and scenic ponds with lighted fountains create an inviting setting for evening strolls. Enjoy the best of coastal Delaware living, conveniently located just a short drive from Lewes and Rehoboth beaches, shopping, and dining. Experience the space, style, convenience, and community you've been looking for, without the wait of new construction!

31143 Tigress Rd, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

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