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

11423 Ashbridge St, Lewes

11423 Ashbridge St, Lewes

4 Beds ⋅ 4 Baths

This is a TBB home features an open floorplan paired with modern design, offering flexibility and comfort across two levels. With 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this home is thoughtfully designed for modern living—including two owner’s suites for added convenience. Standout features include an optional stone fireplace and an electric car charging outlet. The kitchen is designed to impress with double ovens, a modern sink, and decorative pendant lighting over the island, all complemented by quartz countertops. Hard surface flooring runs throughout both the first and second floors for a clean, cohesive look. The spa-inspired bath showcases a rain shower head and tiled bench seat, creating a relaxing retreat at the end of the day. 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.

11423 Ashbridge St, Lewes

Listing courtesy of Delaware Homes Inc. Contact:

33725 Skiff Aly Unit 5108, Lewes

33725 Skiff Aly Unit 5108, Lewes

3 Beds ⋅ 2 Baths

Invest in this beautiful, sunlit, 3-bdrm/2 bath unit conveniently on the first floor with either ramp or stair access! Enjoy kayaking to the Rehoboth Bay from this sought-after waterfront community! Join the Freedom Boat Club right in the community! Great for avid kayakers, paddle boarders, and fisherpersons and crabbers! Feel the bay breeze and smell the saltwater from the private covered porch! Bus stop just outside the community...easily travel to the outlets and beaches! Grocery & restaurants within a mile. Enjoy the gorgeous community pool and pool house! The community is gated and six buildings are keypad access only. Water, trash, and master flood and property insurance policy included in the condo fees! Monthly utilities are very affordable. Some extra features: soft-close cabinetry, wainscoting, tiled back splash, ceiling fans, window treatments, and wall mounted tv! Units can be rented for weekly to annual terms. Come see this beautiful, sunlit unit.

33725 Skiff Aly Unit 5108, Lewes

Listing courtesy of JC Realty Inc. Contact:

33696 Halford Cir, Lewes

33696 Halford Cir, Lewes

5 Beds ⋅ 5 Baths

Modern Coastal living at its finest. Welcome to a lifestyle of effortless relaxation offering the perfect balance of luxury, coastal and family-friendly living. This bright airy, open - concept floor plan connects directly to numerous decks, and spectacular views of Love Creek and preservation area. Community offers private pier, boat docking, boat - ramp, kayaking, fishing, community pool and exercise room Located in sought after Marsh Island Community representing the pinnacle of seaside living. This high-performance quality craftsmanship home has an abundance of options that include ultra-high energy efficiency, innovative floor plan, distressed white coastal engineered wood floors, wainscoting throughout, gourmet kitchen with stainless steel professional grade appliances, full wet bar in lower level for effortless entertaining. Owner has delivered personal touches that make it a truly special home in Model New Condition!!!

33696 Halford Cir, Lewes

Listing courtesy of Taylor Properties. Contact:

24597 Merlot Dr Unit 27-006, Lewes

24597 Merlot Dr Unit 27-006, Lewes

3 Beds ⋅ 2 Baths

Step inside the Provence and experience a thoughtfully designed home that blends comfort and convenience. Whether you enter from the charming side porch or the one-car garage, you’re welcomed by a spacious foyer with the option to take either the stairs or a private elevator to the main living level. ** $17,000 incentive credit on closing costs &/or rate buydown when paying cash or using our preferred lender** Upstairs, the heart of the home opens beautifully. To the left, a bright and expansive living area flows seamlessly into the kitchen—perfect for entertaining—while a nearby deck extends your living space outdoors. This side of the home also features two well-appointed secondary bedrooms and a shared bath. To the right, you’ll find everyday functionality paired with luxury: a convenient laundry room and a serene owner’s suite complete with a private bath, offering a peaceful retreat at the end of the day. Enjoy fresh air and relaxation on the covered deck—an ideal space for morning coffee or evening unwinding. The Provence is designed to make everyday living feel effortless and elevated. Builder paying $21,500 towards buyers closing costs and/or rate buydown with Builders Preferred Lender.

24597 Merlot Dr Unit 27-006, Lewes

Listing courtesy of Northrop Realty. Contact:

77 Filly Ln, Lewes

77 Filly Ln, Lewes

Welcome to Olde Town, a highly sought-after custom home community offering prime location, coastal charm, and true design freedom. 77 Filly Lane presents a rare opportunity to build your custom home in the heart of historic Lewes with no builder tie-in, allowing you to choose the builder and design that fit your vision. Ideally located just one mile from Lewes Beach, Cape Henlopen State Park, and downtown Lewes shopping and dining, this community places you close to everything coastal living has to offer. Enjoy a resort-style pool, green spaces, sidewalks, walking trails, and direct access to the 16-mile Junction & Breakwater Trail. 77 Filly Lane offers the perfect blend of location, amenities, and lifestyle; secure your lot today and start planning your dream home.

77 Filly Ln, Lewes

Listing courtesy of Century 21 Gold Key Realty. Contact:

19 Mayfair Ln, Lewes

19 Mayfair Ln, Lewes

3 Beds ⋅ 2 Baths

Location! Location! Location! Welcome home to this beautifully maintained, move-in-ready gem where you won’t need to change a thing! Enjoy bright, spacious living throughout! The home features a primary bathroom with a convenient connection to the laundry room, making everyday living effortless. Located just minutes from the beaches, this home offers the perfect blend of comfort and coastal lifestyle. Within a community rich with amenities, you’ll have access to a vibrant clubhouse with weekly activities, an indoor saltwater swimming pool, dog park, bocce ball court, and easy access to the popular Lewes–Georgetown Walking Trail. Residents also receive a yearly pass to enjoy the outdoor pool at Colonial East! Recent upgrades include a brand new washer and dryer installed 1/17/26, new carpet throughout, as well as new front door and door frame installed in 2023. This is easy living at its finest — just unpack and start enjoying everything this community has to offer! 5 miles to Lewes Beach. 7 miles to downtown Milton. 9 miles to Rehoboth Beach. 4 miles to Beebe Hospital.

19 Mayfair Ln, Lewes

Listing courtesy of Active Adults Realty. Contact:

8 Georgia Ave Unit 6, Lewes

8 Georgia Ave Unit 6, Lewes

2 Beds ⋅ 1 Baths

Welcome to Bay View Condo’s situated in a prime location overlooking Lewes Beach! This 2 Bedroom condo has an open floor plan that includes a modern updated kitchen with a dining area just to the left which is open to a Family room. The Family room has sliders out to a patio where you can enjoy the tranquility the Sea Air has to offer from the luxury of your own home. The perfect spot for gatherings or a quiet evening enjoying the sunset. Master Family Room, Master Bedroom and Patio overlook the Bay, This is sold fully furnished and move in ready. You can use as an investment property, enjoy as a vacation home or both. Imagine the wonderful memories to be made overlooking the Bay, or simply a calming walk on the beach. Located to nearby Cape May Lewes Ferry, as well as amenities and restaurants including Cape Henlopen State Park, Outlets, Movie Theatres and so much more! Don’t miss your opportunity to own a piece of paradise at the Beach..Bayfront! Home Inspection on File City of Lewes 99 Year Renewable Land Lease. Cost of $1 paid once upon renewal. Right of First Refusal by the Bayview Condominium Association. *Will rent monthly during off season call for details!*

8 Georgia Ave Unit 6, Lewes

Listing courtesy of Keller Williams Realty. Contact:

Tbb Pitch Pine Ct Unit PALMETTO, Lewes

Tbb Pitch Pine Ct Unit PALMETTO, Lewes

4 Beds ⋅ 4 Baths

NOW INCLUDING FINISHED BASEMENTS! NEW CONSTRUCTION AVAILABLE IN THE CHASE OAKS COMMUNITY! THE PALMETTO! Paradise awaits in this beautiful, quiet, tree lined community! This charming home boasts a thoughtfully designed first floor, featuring a sunroom that invites abundant natural light, creating a warm and inviting space for relaxation. Adjacent to it, the cozy café is perfect for casual meals and morning coffee. The spacious gathering room serves as the heart of the home, ideal for entertaining. The first-floor primary suite is a luxurious retreat, complete with a comfortable sitting room, an expansive walk-in closet, and a private bathroom. Additionally, the first floor offers a welcoming guest bedroom with a full bathroom, a versatile flex room that can adapt to your needs, a laundry room, and a 2-car garage. Optional features include a screened porch for enjoying the outdoors, a gourmet kitchen for culinary enthusiasts, and an optional 3rd car garage for added convenience. Upstairs, the second floor provides a guest retreat with a bedroom, a full bathroom, and a bonus room. One of the Palmetto's standout features at Chase Oaks is the included finished basement, providing exceptional additional living space from the start. This lower level includes a spacious recreation room, offering endless possibilities for entertaining, relaxing, creating a home office, fitness area, or media room. It also features an additional bedroom and full bathroom.*Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

Tbb Pitch Pine Ct Unit PALMETTO, Lewes

Listing courtesy of DRB Group Realty, LLC. Contact:

Tbb Pitch Pine Ct Unit LATITUDE, Lewes

Tbb Pitch Pine Ct Unit LATITUDE, Lewes

4 Beds ⋅ 3 Baths

NOW INCLUDING FINISHED BASEMENTS! NEW CONSTRUCTION AVAILABLE IN THE CHASE OAKS COMMUNITY! THE LATITUDE! Paradise awaits in this beautiful, quiet, tree lined community! The Latitude features an open concept kitchen, breakfast area and family room. Primary suite is tucked away off the family room. Two secondary bedrooms with shared hall bath at the front of the home away from the primary suite. Add a screen porch. Add an upper level with unfinished storage, a bonus room. One of the Latitude's standout features at Chase Oaks is the included finished basement, providing exceptional additional living space from the start. This lower level includes a spacious recreation room, offering endless possibilities for entertaining, relaxing, creating a home office, fitness area, or media room. It also features an additional bedroom and full bathroom, making it ideal for guests, extended family, or multi-generational living. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

Tbb Pitch Pine Ct Unit LATITUDE, Lewes

Listing courtesy of DRB Group Realty, LLC. Contact:

31667 Siham Rd Unit 11688, Lewes

31667 Siham Rd Unit 11688, Lewes

3 Beds ⋅ 2 Baths

Welcome to this fully renovated 3-bedroom, 2-bathroom manufactured home in the peaceful Whispering Pines community of Lewes, Delaware. Thoughtfully transformed in 2023, this compact home offers updated finishes, flexible bedroom space, and a low-maintenance coastal lifestyle just minutes from Route 1. Inside, the home has been refreshed with a modern coastal feel throughout. The kitchen is a standout feature with vaulted ceilings, full-height subway tile backsplash, warm butcher block countertops, grey cabinetry, and stainless steel appliances. The updated finishes give the home a clean, move-in ready feel while keeping the layout practical and easy to maintain. The three-bedroom layout provides flexibility for a variety of needs. Use the bedrooms for guests, a home office, hobby space, or additional storage depending on your lifestyle. Walk-in closets offer added functionality, and the two full bathrooms make the home comfortable for everyday living or hosting visitors. Outdoor storage is another major benefit of this property. The separate shed provides valuable space for beach gear, bikes, tools, seasonal items, or anything you do not want taking up room inside the home. Double entry doors at both the front and back of the home add convenience and easy access. Whispering Pines offers a quiet setting with well-maintained surroundings and community amenities, including a pool, lawn care, and trash service. Located just off Route 1, this home offers easy access to shopping, dining, bike paths, parks, a winery, breweries, and Delaware’s beaches. This home is located on leased land with a monthly lot rent of $992. The seller is willing to cover the first three months of lot rent with a valid offer. This renovated home is a great option for buyers seeking an updated, manageable home in a convenient coastal location.

31667 Siham Rd Unit 11688, Lewes

Listing courtesy of The Parker Group. Contact:

Tbb Chase Oaks Dr Unit DUNE, Lewes

Tbb Chase Oaks Dr Unit DUNE, Lewes

4 Beds ⋅ 4 Baths

NOW INCLUDING FINISHED BASEMENTS! NEW CONSTRUCTION AVAILABLE IN THE CHASE OAKS COMMUNITY! THE DUNE! Paradise awaits in this beautiful, quiet, tree lined community! The Dune features an open concept kitchen, breakfast area and family room. Primary suite tucked away off the family room. Two secondary bedrooms with shared hall bath and Loft on 2nd level. Add a screen porch. Two-car garage included. Add a recreation garage or full third bay for more space. One of the Dune's standout features at Chase Oaks is the included finished basement, providing exceptional additional living space from the start. This lower level includes a spacious recreation room, offering endless possibilities for entertaining, relaxing, creating a home office, fitness area, or media room. It also features an additional bedroom and full bathroom. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

Tbb Chase Oaks Dr Unit DUNE, Lewes

Listing courtesy of DRB Group Realty, LLC. Contact:

27 Bridle Ridge Cir, Lewes

27 Bridle Ridge Cir, Lewes

3 Beds ⋅ 4 Baths

New Roof. New upstairs HVAC system. New Price!! Here's an opportunity to purchase into a million dollar neighborhood without spending a million dollars upfront . All this property needs is someone with a vision and the willingness to do some updating. This 3 bedroom 3.5 bath house with a pool sits on over 1.4 acres in the desirable neighborhood of the Estates at Bridle Ridge. Designed around an open floor plan, the house features primary bedrooms on both the first and second floors. Both primaries have ensuite bathrooms with double vanities, whirlpool tubs and separate walk-in showers. The second floor primary also has an extra large walk-in closet. There is an additional bedroom, as well as two rooms that can be used as office space or an upstairs den. All three share a hall bath on this floor and an upstairs laundry room. Lastly, there is a staircase access to a fully floored attic that could easily be converted into more living space and still maintain adequate room for storage. The layout on the first floor with a kitchen teeming with cabinets and counterspace, provides a number of possibilities for entertaining and dining, Moving to the rear of the house you will find a newly renovated screened porch that overlooks the expansive backyard. A maintenance free deck with a built-in hot tub was also added recently and provides a relaxing spot to enjoy morning coffee or grilling in the evening. All of this is only minutes away from downtown Lewes and the beaches. The property is being sold "as is" and is priced accordingly. 5439-BL

27 Bridle Ridge Cir, Lewes

Listing courtesy of Jack Lingo - Lewes. Contact:

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