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

17240 Water View Dr, Lewes
$80,000
2 Beds ⋅ 2 Baths
Welcome to effortless coastal living at its finest in this Charming Coastal Bungalow! Nestled in a desirable waterfront community just minutes from historic downtown Lewes and local beaches, this delightful 2-bedroom, 2-bathroom bungalow offers the ultimate relaxed beach lifestyle. Key Features & Major Updates include a Spacious Open-Concept Layout which seamlessly connects the living, dining, and kitchen areas—ideal for easy everyday living and entertaining. The Oversized Kitchen offers generous counter and cabinet space to prep your favorite meals after a day on the water. The home features a Fantastic Outdoor Living space where you can unwind on the huge screened-in porch or soak up the sun on the open deck. The home offers peace of mind with a 5-year-old roof and a 1-year-old HVAC system. The home is Turnkey Ready as it is being sold fully furnished for immediate occupancy so you can start enjoying your new home from day one! The Hassle-Free Community Amenities (Included in the Ground Rent) are a Sparkling community pool, Community dock for waterfront enjoyment, and convenient trash removal and lawn care! The home is located in a Prime Lewes Location conveniently situated just minutes from downtown Lewes’s favorite local restaurants, beach, shopping, State Parks, and more.

17240 Water View Dr, Lewes

Listing courtesy of RE/MAX Associates. Contact:

32190 Sandpiper Dr, Lewes
$395,000
2 Beds ⋅ 2 Baths
Close to Everything but Away From it All. Impressive Traditional/Ranch home in a prime location in the well-established Nassau Acres quiet and private community conveniently located with easy access to Rt 1 just North of the Nassau Bridge outside of Lewes. RV'S, Boats and Campers are welcome. A two bedroom, 2 full bath with a parlor/office room in mint condition and a bright open floor plan with a Cathedral ceiling, a Gourmet Kitchen with a generous dining area and a more formal dining area just off the kitchen and living room. A very convenient utility/laundry room with a sink between the kitchen and the garage and a relaxing and secluded back yard. Recent upgrades include a brand new crawl space with sump pump and gutter diversions with pop-ups away from the foundation, upgraded electrical outlets, a new roof in 2019, new gutter guards and the home was just recently and completely powerwashed along with low HOA fees and being within minutes to downtown Lewes, the State Park, the Cape-May Lewes Ferry and all Beaches, Restaurants and Shopping so don't miss this Great Opportunity to own this tasteful home with teriific value.

32190 Sandpiper Dr, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

18335 Pine Ln, Lewes
$389,000
3 Beds ⋅ 2 Baths
Seller says Bring All Offers! Welcome to 18335 Pine Lane in Sandy Brae, offering a great opportunity to make a home your own in a convenient Lewes location. Situated on a spacious corner lot, this 3-bedroom, 2-bath ranch offers single-level living along with a full unfinished basement providing excellent storage, workshop space, and future possibilities. The home features a new HVAC system, a cozy woodstove, and a side sunroom addition that provides additional living space and plenty of natural light. Outside, the property offers added flexibility that's increasingly hard to find near the coast. Sandy Brae features a low HOA. Enjoy easy access to historic downtown Lewes, Lewes Beach, Cape Henlopen State Park, area bike and walking trails, shopping, restaurants, and everyday conveniences, while still enjoying the feel of an established residential community. Being sold AS-IS as part of an estate, this property offers an excellent opportunity for a buyer to update and personalize the home while benefiting from a new HVAC system and some of the features that make Sandy Brae so appealing.

18335 Pine Ln, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

41 Whitehaven Way, Lewes
$179,000
3 Beds ⋅ 2 Baths
Perfect for a getaway or full time residence, this freshly carpeted spacious 3 bedroom, 2 bath home has so much to offer. A large kitchen with island & built-in storage, a dining area, laundry room, ensuite bedroom with oversized showers and built-in grab bars, a large living room with corner fireplace for cozy season and a wrap around porch to appreciate the outdoors. Explore Sussex West, an active adult community with mature trees and amenities that include a clubhouse, heated indoor swimming pool with chairlift & showering facilities, dog park, pickle ball, bocce ball, shuffleboard and horseshoe pit. Snow removal and recycling are included with your land lease and you can enjoy community-sponsored events and an onsite management team. RV storage is allowed for a fee. Live a short drive to tax-free outlets, shops and restaurants. Quick access to Lewes/Georgetown Trail.

41 Whitehaven Way, Lewes

Listing courtesy of Jack Lingo - Rehoboth. Contact:

436 River Birch Dr, Lewes
$739,000
4 Beds ⋅ 4 Baths
Looking for a short bike ride to downtown Lewes and Second Street in Lewes ? This gem in Lewes Waterfront Preserve is waiting for you. This unit features 4 BR/ 3.5 BA with a first and second floor primary and 2 other generous bedrooms. The gourmet kitchen is complete with a large quartz island, stainless steel appliances, backsplash and upgraded cabinetry. LVP flooring throughout the downstairs gives an easy beach clean up and the back composite deck facing open space and private woods will sure be a crowd pleaser. Did I mention the second living space on the second level? And the unfinished basement awaiting your personal touches or keep it the way it is for your beach gear and winter attire. This home will surely be an entire family favorite for years to come. Check this one out today before it's too late!

436 River Birch Dr, Lewes

Listing courtesy of Patterson-Schwartz-Rehoboth. Contact:

34521 Bookhammer Landing Rd, Lewes
$499,900
4 Beds ⋅ 4 Baths
Four-bedroom, four-full-bathroom home on 1.41 wooded acres in Lewes, Delaware, with no HOA, a new roof installed in March 2026, and a two-car attached garage. Located on Bookhammer Landing Road in the Cape Henlopen School District, minutes from Cape Henlopen State Park, Lewes Beach, and downtown Lewes. The main level features a first-floor bedroom with a full bathroom, a living room with a gas fireplace, a dining area, and a kitchen with solid hardwood floors. The second level includes a primary bedroom with two full bathrooms, one with a soaking tub, plus two additional bedrooms and a fourth full bathroom. The rear deck overlooks a private, wooded lot, a quiet setting for morning coffee, evening dinners outdoors, and time away from neighbors and traffic. With no shared walls and trees on all sides, the property offers a peaceful, secluded feel that is hard to find this close to the coast. The two-car attached garage provides storage and covered parking year-round. Cape Henlopen State Park is minutes away, Lewes Beach and the shops and restaurants of downtown Lewes are a short drive, and Rehoboth Beach is about 15 minutes south. No HOA fees. A quiet, wooded retreat on Bookhammer Landing Road in Lewes, DE, close to the beaches, parks, and dining of coastal Sussex County.

34521 Bookhammer Landing Rd, Lewes

Listing courtesy of Coldwell Banker Realty. Contact:

22754 Holly Way W, Lewes
$414,900
3 Beds ⋅ 2 Baths
** Please note: One day gate code for Open House 22754 (then hit the green button) Welcome to Angola Bay. This exceptional 3-bedroom, 2-bath home seamlessly combines comfort, flexibility and is being sold semi-furnished. Experience a vacation-like atmosphere every day in this amenity-rich, gated community of Angola by the Bay, located on the Delmarva Peninsula. The community boasts a private marina and boat docks, providing direct access to Burton Prong and Rehoboth Bay. With a low homeowners' association fee, residents can enjoy a wealth of amenities, including a clubhouse, saltwater swimming pool, tennis and pickleball courts, a pavilion, playground, sports courts, horseshoe pits, basketball facilities, and over five miles of scenic walking trails. Moreover, there are common areas equipped with picnic tables and a crabbing pier. Whether you are seeking a move-in-ready beach retreat, a year-round residence, or an investment opportunity with potential for growth, 22754 Holly Way W. offers an ideal blend of coastal charm, with future possibilities—just minutes away from Delaware's beautiful beaches, shopping, dining, and all that the Lewes lifestyle has to offer. Schedule your private tour today!

22754 Holly Way W, Lewes

Listing courtesy of Keller Williams Realty. Contact:

33935 Middleton Cir Unit 4, Lewes
$344,000
2 Beds ⋅ 2 Baths
Welcome to this beautifully updated 2-bedroom, 2 Bath Condo in the desirable Plantations! This inviting home offers a comfortable open layout with tasteful updates throughout such as new flooring & carpet, updated kitchen with new countertops, cabinets and backsplash, creating a move-in-ready retreat near all that the Delaware Beaches have to offer. Nicely sized bedrooms, as well as windowed Sunroom overlooking the common area. Enjoy the convenience of low-maintenance condo living along with the amenities and community atmosphere Plantations is known for. Whether you're looking for a full-time residence, beach getaway, or investment opportunity, this condo offers an excellent combination of comfort, location, and value. Conveniently located just minutes from downtown Lewes, area beaches, shopping, dining, and recreation, this is an opportunity you won't want to miss!

33935 Middleton Cir Unit 4, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

15450 Solomon Way, Lewes
$799,990
3 Beds ⋅ 3 Baths
Prime East of Route 1 coastal location - minutes to beaches, trails, and the best of Lewes. The Eastwood Loft offers a beautifully balanced open-concept layout with timeless classic design, creating a home that feels both inviting and elevated. With a projected settlement in February 2027, this thoughtfully designed residence features 3 bedrooms, 3 bathrooms, and a 2-car garage. Standout spaces include a deck, a spacious loft space, and a luxurious Ultra Spa bath that brings a retreat-like feel to everyday living. The fireplace adds warmth and character to the main living area, while LVP flooring throughout the first floor enhances durability and flow. The kitchen is a true focal point, showcasing an Ultra Staggered Gourmet layout, quartz countertops, and design-forward functionality ideal for both entertaining and daily use. 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. Located just a 15-minute bike ride from the beach and downtown Lewes, this home is situated in an amenity-rich community focused on low maintenance and a coastal luxury lifestyle, complete with a lifestyle director to enhance your living experience. Don’t miss the opportunity to live in this brand-new, exquisite home! Schedule your tour today and experience the perfect blend of luxury and convenience.

15450 Solomon Way, Lewes

Listing courtesy of Delaware Homes Inc. Contact:

23134 Waggoner Ave, Lewes
$575,000
3 Beds ⋅ 3 Baths
Welcome to this beautifully maintained three-bedroom, 2.5 bath townhome in the desirable community of Covered Bridge Trails in Lewes, Delaware. Designed for comfortable everyday living and easy entertaining, the home features a bright, open-concept layout with spacious living and dining areas that flow seamlessly into the kitchen. The kitchen offers generous cabinetry, stainless steel appliances, a large center island with additional seating, and ample workspace, creating a natural gathering place at the heart of the home. With three bedrooms and two and a half bathrooms, the flexible floor plan provides plenty of room for guests, a home office, or additional living space. Neutral finishes and abundant natural light create a welcoming feel throughout, while the outdoor patio offers a peaceful place to relax and enjoy the surrounding pond views. Residents of Covered Bridge Trails, an active 55+ community, enjoy exceptional amenities including a resort-style pool, clubhouse, fitness center, pickleball courts, community garden spaces, and a dog park. Outdoor enthusiasts will love the community's direct access to the Lewes-Georgetown Trail, providing miles of scenic biking and walking right from the neighborhood. Just minutes from Lewes Beach, downtown Lewes, Cape Henlopen State Park, and the area's premier dining and shopping destinations, this exceptional home offers the best of Delaware coastal living.

23134 Waggoner Ave, Lewes

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

19432 Safflower Way, Lewes
$699,000
3 Beds ⋅ 3 Baths
Almost new home, fully furnished with family/rec room in finished basement for a hard-to-find second living space. Just built in November 2025 this upgraded home features one floor living that includes a great room, chef's kitchen, screened porch, luxury primary bedroom & bath, guest bedroom & bath plus laundry and a two-car garage. Bonus features continue with the finished basement that includes a huge family room plus 3rd bedroom and 3rd full bath. The main floor has luxury plank flooring, the upgraded kitchen with Monogram appliances, quartz island, high ceilings and great light. All 3 full baths were upgraded with tile showers and flooring plus quartz vanity tops. Enjoy the open green space in the back and on the side from your screened porch and the ease of living with community pool and lawn care included in your low monthly fee.

19432 Safflower Way, Lewes

Listing courtesy of Jack Lingo - Rehoboth. Contact:

22845 Camp Arrowhead Rd, Lewes
$299,000
2 Beds ⋅ 1 Baths
Discover a unique opportunity in Angola Neck Park, offering two separate parcels, each just over one-third of an acre, with a charming two-story bungalow situated where the properties meet. Whether you are searching for a coastal retreat, investment opportunity, or a property with future development potential, this versatile offering provides plenty of possibilities. The home features two bedrooms and one bathroom, with all plumbing throughout the residence having been replaced and updated. The beautiful wood ceiling with skylight and ceiling fan flows from the living room to the kitchen. The open concept kitchen has stainless steel appliances, dual sinks and a center island with counter seating. Outside, the property includes two sheds and a gazebo, providing additional storage and space to relax and enjoy the surroundings. Separate access points from both Camp Arrowhead Road and Magnolia Road add to the property's convenience and potential. With no HOA restrictions and two parcels included in the sale, this property presents a rare opportunity to enjoy, improve, or explore future development possibilities. Located in a desirable peninsula location across Rehoboth Bay from Delaware's renowned coastal beaches, you will be close to fishing, boating, attractions, outlet shopping, dining, and all the fun and relaxation that coastal living has to offer. Bring your vision and discover the possibilities this unique Angola Neck Park property has to offer!

22845 Camp Arrowhead Rd, Lewes

Listing courtesy of Compass. Contact:

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