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

29524 Dagger Board Dr, Lewes
$510,000
3 Beds ⋅ 2 Baths
Coastal living made easy in sought-after Lewes, Delaware. This 3-bedroom, 2-bath Anchors Run home pairs a bright, open layout with outstanding outdoor space and a private backyard. There are no homes directly behind it. Instead, it looks out over a community berm full of wildflowers and mature greenery, so it feels tucked away while staying close to Lewes and Rehoboth Beach. The open main living area joins the kitchen, dining room, and living room into one welcoming, light-filled space. Luxury vinyl plank flooring runs through the main living areas, and the builder's upgraded lighting package adds ceiling lights throughout. The kitchen is the heart of the home. It has quartz counters, 42-inch soft-close cabinets, under-cabinet lighting, and an oversized island with breakfast-bar seating. Upgraded KitchenAid appliances include a dishwasher and a refrigerator with icemaker and water dispenser, and pendant lights over the island add both function and style. The dining and living areas next to the kitchen have plenty of room for daily life and hosting. Custom drapes with sheers dress the windows, and sliding glass doors lead out to a covered rear porch overlooking the private backyard. From the porch, the living space flows out to a large paver patio that runs the full width of the back of the home and wraps around one corner. There's room for separate dining, lounging, and entertaining areas, plus a stone sitting wall for extra seating, a bubbler fountain as a focal point, and a built-in grilling area. What really sets the patio apart is the view. With no neighbors directly behind, it faces the community berm, where wildflowers and greenery make a colorful, ever-changing backdrop for morning coffee, summer dinners, or quiet nights outside. Lawn care and irrigation are covered by the HOA, so the yard stays looking great and you get more time to enjoy it. Inside, the primary suite sits at the back of the home and shares those same private views. It features a tray ceiling and a spacious en suite bath with a double vanity, linen closet, and large walk-in closet. The upgraded, extra-deep Roman-style tile shower has a full-length bench and two separately controlled shower heads. A dedicated laundry room sits just off the primary suite, close at hand but separate from the main living space. The other two bedrooms are at the front of the home. The third is currently set up as a home office, which is ideal for anyone working from home while keeping a true 3-bedroom layout. All three bedrooms are pre-wired for ceiling fans. The second full bath has also been upgraded with a custom frameless glass shower panel for a clean, modern look. A handy mudroom links the main living area to the garage and leads to the full unfinished basement. The builder roughed in plumbing for a future bathroom, and the basement also has extra outlets and overhead lighting, so it's ready to become a rec room, gym, office, guest space, or a mix of all of them. The garage also has an EV charger already installed. Anchors Run residents enjoy a community pool and a clubhouse with a fitness center and meeting room. With historic downtown Lewes less than 5 miles away and Rehoboth Beach less than 7, this home brings together privacy, flexible space, smart upgrades, and easy access to the best of coastal Delaware. Seller is a licensed real estate agent.

29524 Dagger Board Dr, Lewes

Listing courtesy of Keller Williams Realty. Contact:

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

22794 Dogwood Dr, Lewes

Listing courtesy of Keller Williams Realty. Contact:

28105 Winona Ln, Lewes
$799,000
5 Beds ⋅ 3 Baths
Welcome to 28105 Winona Lane, where modern elegance, thoughtful design, and exceptional indoor and outdoor living come together in a beautifully appointed home less than two years old. Offering five bedrooms, three full bathrooms, a finished basement, and a three-car garage, this residence provides an impressive combination of space, style, and functionality, all set against a picturesque wooded backdrop. Step inside to discover a light-filled, open-concept floor plan designed for both effortless everyday living and entertaining. The spacious living room, anchored by a beautiful fireplace, flows seamlessly into the dining area and stunning gourmet kitchen. Thoughtfully appointed with quartz countertops, a five-burner gas cooktop, built-in wall oven and microwave, and an additional beverage refrigerator in the dining area, this inviting space is as functional as it is beautiful. An expansive island provides the perfect gathering place, while the open layout creates an easy connection between each living space. The first-floor primary suite offers a peaceful retreat, complete with a beautifully designed ensuite bath featuring dual vanities, an oversized tiled shower with glass enclosure and built-in bench, and a generous walk-in closet. A dedicated home office provides an ideal space for working remotely or enjoying a quiet escape. Upstairs, additional bedrooms and a versatile loft offer flexibility for guests, family, or a second living area. Convenient attic storage adds another layer of practicality to this thoughtfully designed home. The finished basement provides an incredible extension of the living space, ideal for entertaining, recreation, fitness, or a media room. Multiple dedicated storage areas ensure everything has its place, while the potential to add an additional bedroom and an existing bathroom rough-in offer exciting possibilities for future customization. Yet perhaps the most captivating feature of this property awaits outdoors. Step onto the covered rear porch and discover your own private retreat. An expansive fenced backyard, extensive landscaping, and a dedicated fire pit area create an idyllic setting for gatherings, quiet mornings, and evenings under the stars. Beyond the beautifully maintained lawn, a peaceful wooded tree line provides a stunning natural backdrop and an exceptional sense of privacy—a truly special feature that sets this home apart. With the added convenience of a three-car garage and access to community amenities including a swimming pool, clubhouse, and pickleball courts, this nearly new residence offers the perfect balance of refined interiors, flexible living spaces, and an inviting outdoor lifestyle. Why wait for new construction when you can enjoy the beauty, upgrades, and established outdoor spaces of 28105 Winona Lane? A home that truly offers room to live, entertain, and unwind.

28105 Winona Ln, Lewes

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

69 Filly Ln, Lewes
$1,225,000
3 Beds ⋅ 3 Baths
69 Filly Lane in Olde Town offers a unique opportunity to build an award-winning Kingfisher model by Schell Brothers, one of Coastal Delaware's most sought-after floor plans. This to-be-built opportunity combines one of the most desirable Lewes locations with the flexibility to personalize your new home through a variety of available options and upgrades. The Kingfisher combines distinctive architecture, spacious living areas, and the convenience of a first-floor primary suite. The impressive two-story great room creates an open, inviting atmosphere, while the generously sized kitchen flows naturally into the main living spaces, ideal for both everyday living and entertaining. A versatile first-floor flex room offers additional space for a home office, formal dining room, or other uses, while the second level provides comfortable accommodations for family and guests. One of the most appealing aspects of this opportunity is the ability to personalize the home. Buyers may select from available structural options, design finishes, and upgrades, allowing them to create a home that reflects their individual preferences and lifestyle. The location is equally compelling. This particular lot location in Olde Town at Lewes is ideally situated adjacent to the Junction & Breakwater Trail and across from the Lewes Public Library, with historic downtown Lewes, Cape Henlopen State Park, local beaches, restaurants, and shopping all just a short distance away. The community also offers a swimming pool, pool house and other amenities for residents to enjoy. With a desirable homesite and the opportunity to customize a popular floor plan, this offering brings together the advantages of new construction and an exceptional Lewes location. The lot can also be purchased separately with no builder tie-in or timeframe to build for $625,000.

69 Filly Ln, Lewes

Listing courtesy of Jack Lingo - Lewes. Contact:

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

24160 Port Ln Unit 101, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

33989 Cornflower Ln, Lewes
$57,000
2 Beds ⋅ 1 Baths
Nestled in the Love Creek Park community, this delightful, manufactured home offers a perfect blend of comfort and convenience. This single-wide home features two cozy bedrooms and a full bathroom, making it an ideal retreat for those seeking a peaceful weekend getaway. A third room and sunroom off the kitchen provide extra space and privacy. Designed for year-round comfort and efficiency, this inviting home features energy-efficient double-pane windows, durable vinyl siding, and a heat pump system instead of the propane or kerosene heating commonly found in the area. Inside, a welcoming living space with an electric fireplace creates the perfect setting for cozy evenings. Recent updates, including an upgraded HVAC system, a new water heater, and additional insulation, further enhance comfort and energy efficiency throughout the home.The property is located on a corner lot, providing ample outdoor space for parking. With access to Love Creek Marina, residents can purchase a boat slip to enjoy the soothing sounds of the water and the beauty of nature steps from their home. Whether you're looking to unwind on the river or explore the surrounding area, there is easy access from the marina to the Delaware Bay and Lewes inlet. With a bus stop less than a mile away, commuting and exploring the wider area is a breeze. Education is a priority in this community, with well-regarded schools nearby that cater to a variety of learning needs. Embrace the tranquility of comfort and convenience and make this charming, manufactured home your own. Experience the joy of living in a place that feels like home and a boater’s paradise.

33989 Cornflower Ln, Lewes

Listing courtesy of Coldwell Banker Premier - Lewes. Contact:

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