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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

33887 Magnolia Plantations Dr, Lewes
$499,900
3 Beds ⋅ 2 Baths
Modern Single-Level Living Just 3 Miles to the Beach Move right into effortless coastal living with this beautifully bright, single-story home. Designed for both daily comfort and easy entertaining, the layout features a light-drenched sunroom, formal dining room, and an expansive living area. The eat-in kitchen comes equipped with sleek stainless steel appliances and durable tile flooring. Unwind in the spacious primary suite, complete with a generous walk-in closet and private en-suite bath. Two versatile guest bedrooms offer plenty of space for visitors, a home office, or hobbies. Step outside to your private rear deck to relax, take in the serene natural surroundings, and enjoy coastal breezes—all just minutes from the shoreline. Schedule your private tour today!

33887 Magnolia Plantations Dr, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

23687 Herring Reach Ct, Lewes
$570,000
3 Beds ⋅ 3 Baths
Welcome to 23687 Herring Reach Court – a beautifully maintained 3-bedroom, 3-bathroom home with numerous upgrades, tucked away in the sought-after waterfront community of Bay Pointe. This property offers both comfort and potential, with over 2,100+ square feet of living space and a full unfinished basement ready for your vision—whether it’s a rec room, workshop, or extra guest suite, the possibilities are endless. The home’s open layout is warm and inviting, with ample space for entertaining or relaxing. The gourmet kitchen opens into a large family room with gas fireplace. A sunroom is off the family room allowing entertaining or reading area. The elegant owner's suite features tray ceilings, a spacious walk-in closet, and an en-suite bath for your ultimate comfort. Upstairs offers a nice loft along with an additional bedroom and full bathroom. Just imagine enjoying peaceful mornings or evening gatherings on your expansive back deck, where your backyard opens up to pretty landscaping and a serene tree line, offering both privacy and a picturesque natural view! Pre-listing home inspection has been completed, available upon request. Residents of Bay Pointe enjoy wonderful amenities such as lawn mowing/edging/fertilization, a large outdoor pool and a newly renovated clubhouse. The clubhouse has a library, work out room, meeting room and shower rooms. The community has water access and kayak storage with a community dock for fishing/crabbing. To top it off, there is a boat/RV storage area within the community. All of this within just a short drive to downtown Lewes, Cape Henlopen State Park, and the beaches. This is the place to live!

23687 Herring Reach Ct, Lewes

Listing courtesy of Iron Valley Real Estate Premier. Contact:

23584 Holly Cir, Lewes
$448,000
3 Beds ⋅ 2 Baths
Don't miss this opportunity to purchase a well-cared for home with single level living in Lewes. New roof installed in 2022, new HVAC in 2022, new flooring and paint throughout in 2019. Home features 3 bedrooms and 2 full Baths, Deck off the rear, decorative stone walkway leads to a fire pit for relaxing after a long day. With vinyl siding and windows this home is low maintenance. Bring your furniture and move right in! With low HOA fees, Central Water and Sewer and located in Lewes just off Camp Arrowhead Road this home is a bargain and will not last long, at this price!

23584 Holly Cir, Lewes

Listing courtesy of RE/MAX Realty Group Rehoboth. Contact:

28051 Starfish Ct, Lewes
$414,999
4 Beds ⋅ 3 Baths
Welcome to this beautifully maintained 4-bedroom, 2.5-bathroom home in the sought-after Windswept at Lewes community, built in 2023 and designed for modern living. Light-filled and inviting, this home features custom Bali blinds, luxury vinyl plank flooring throughout the main living areas recessed lighting, and an open-concept floor plan perfect for both everyday living and entertaining. The gleaming white kitchen offers abundant cabinetry, stainless steel appliances, a center island with counter seating, and recessed lighting, with convenient access to the backyard. The spacious living room flows seamlessly into the dining area, creating an ideal gathering space. A powder room completes the main level. Upstairs, plush carpeting adds comfort throughout. The spacious primary suite features a walk-in closet and a private ensuite bathroom with dual vanities and a tub/shower combination. Three additional guest bedrooms share a full hall bathroom, and a conveniently located laundry room completes the second floor. Step outside to enjoy the fenced backyard, featuring durable aluminum fencing with two locking gates, a shed on a concrete slab, and recently planted peach and cherry trees. The home's location is a standout feature, with a bike trail directly adjacent to the property and water access for fishing and crabbing just one mile away on Angola Beach. Residents of Windswept at Lewes enjoy exceptional community amenities including a swimming pool, bathhouse with shower and restrooms, pickleball courts, walking trails, and a tot lot playground, offering endless opportunities for recreation and relaxation. This nearly new home combines modern style, comfort, and an unbeatable coastal lifestyle in one of Lewes' most desirable communities.

28051 Starfish Ct, Lewes

Listing courtesy of Compass. Contact:

32920 Conch Ct, Lewes
$600,000
3 Beds ⋅ 2 Baths
Welcome to 32920 Conch Court, a well-maintained three-bedroom home offering convenient first-floor living in the established Sea Wood neighborhood of Lewes. The home features a comfortable layout, sunroom, and attached garage, along with mature landscaping, a patio, spacious yard, and tree-lined backdrop for added privacy. Enjoy the classic neighborhood setting with more breathing room and established surroundings, all just minutes from downtown Lewes, Cape Henlopen State Park, restaurants, medical facilities, shopping, and more. A great opportunity to enjoy the best of Lewes and coastal Delaware.

32920 Conch Ct, Lewes

Listing courtesy of 360 PROPERTY SOLUTIONS. Contact:

16996 4th St, Lewes
$450,000
4 Beds ⋅ 2 Baths
Just 2.5 miles from Lewes Beach, this spacious 4-bedroom home offers something increasingly hard to find near the coast: room to spread out, exceptional storage, and the opportunity to make it your own. Situated on a generous, open lot, this 4-bedroom, 2-bathroom ranch-style home offers approximately 1,280 square feet of single-level living space, a full basement, and an oversized detached garage. Whether you're looking for a primary residence, coastal getaway, or investment opportunity, this property delivers the space, flexibility, and location to bring your vision to life. Inside, you'll find a welcoming living room filled with natural light, hardwood flooring throughout much of the home, and a comfortable layout that connects the living, dining, and kitchen areas. All four bedrooms are conveniently located on the main level, providing flexibility for guests, a home office, or additional living needs. Just off the main living area, an enclosed sunroom offers a versatile space to enjoy throughout the seasons. One of the property's most impressive features is the expansive full basement, offering approximately 1,272 square feet of unfinished space with multiple storage areas and plenty of room for a workshop, hobbies, or future improvements. Outside, the oversized detached garage, measuring approximately 28 by 23 feet, provides exceptional space for vehicles, tools, recreational equipment, and all your beach essentials. The outdoor space is equally appealing, featuring a large, open yard, mature trees, a rear deck perfect for relaxing or entertaining, and plenty of room to enjoy the outdoors. And then there's the location. Just an 8-minute drive to Lewes Beach, you'll enjoy convenient access to the beautiful Delaware Bay shoreline, historic downtown Lewes, Cape Henlopen State Park, and an incredible selection of local restaurants, boutiques, and outdoor recreation. Spend your mornings at the beach, afternoons exploring the nearby trails, and evenings enjoying everything this sought-after coastal community has to offer. With its desirable location, four-bedroom layout, substantial basement, oversized garage, and spacious outdoor setting, 16996 4th Street presents an exciting opportunity to enjoy the Lewes lifestyle while creating a home that's uniquely yours. Your next chapter at the Delaware coast starts here. Schedule your private showing today!

16996 4th St, Lewes

Listing courtesy of Iron Valley Real Estate Premier. Contact:

118 Beebe Ave, Lewes
$988,000
2 Beds ⋅ 2 Baths
Modern Living Meets Historic Lewes Charm Step into a designer’s vision of effortless, open-concept living, where modern aesthetics seamlessly blend with classic Historic Lewes architecture. Custom-built using premium materials, this residence delivers simple yet refined luxury engineered for ultra-low, maintenance-free upkeep. Inside, architectural details like exposed beams and a cozy gas fireplace create a warm, inviting atmosphere across the main living spaces. The flexible floor plan includes two spacious bedrooms plus a versatile loft ideal for a third sleeping area, home office, or studio. Outside, a relaxing screened porch offers the perfect sanctuary for coastal mornings and evenings. Enjoy seamless contemporary style and unmatched convenience, all located just steps from in-town dining, boutique shopping, and historic coastal amenities.

118 Beebe Ave, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

33471 Daisy St Unit H-48, Lewes
$75,000
2 Beds ⋅ 2 Baths
Angola Beach & Estates is a marina community on Hazard Cove, which leads out to the Rehoboth Bay, so it ideal for boaters and anglers. The community has two large pools and two playgrounds. Some of the other amenities include tennis/pickleball courts, basketball courts & kayak/canoe launch area. The marina has a boat ramp with plenty of parking spaces for your trailer while you’re out on the water (some slips for rent, but there may be a waiting list). The Rehoboth Beach boardwalk is approx. 10 miles away. This 1984 Marshfield singlewide is 14’x70’ for approximately 980 sq. ft. of living space. The main living area is an open concept with the living room adjoining the eat in kitchen. The kitchen has a breakfast bar and space for a dinette set near the pantry. Appliances include a range, range hood & a refrigerator. The home has a popular split bedroom plan. The main bedroom is a step-up into the suite. Its bath has an upgraded sink vanity and a walk-in shower. This bedroom has two closets. The second bedroom, on the opposite side of the house, is next to the second full bath. The second bedroom has a double closet. That second bath has also been updated with a solid-surface sink vanity and a walk-in shower. The laundry area is in the hall with a full-size washer and dryer. Storage shed. Front patio & rear deck. Off-street, driveway parking for 2 vehicles. Leasehold interest with a Market Rate Lot Rent amount of approx. $885/mt. (renews annually with any increases capped as per 25 Del. C. Sec 7050-70534. Lot rent includes water, sewer & trash/recycle. Homeowner pays electric, fuel (oil), cable/Internet/FiOS, and lawn service. The community owner requires an Application from the Buyer and all occupants 18-years-of-age or older, with acceptance based on: 1)Income Verification; 2)Credit Bureau Score (including debt-to-income ratio); 3)Clean Criminal Background Check. Leased-land properties do not qualify for conventional 30-year mortgages, but financing may be available to qualified borrowers from a few Lenders that specialize in installment/chattel loans for manufactured homes on leased land. Closing costs include a transfer tax (3.75% DMV Doc Fee), a settlement agent fee, and standard pro rata amounts.

33471 Daisy St Unit H-48, Lewes

Listing courtesy of SEA BOVA ASSOCIATES INC.. Contact:

32900 Ocean Bluff Dr, Lewes
$559,000
4 Beds ⋅ 3 Baths
Welcome to this inviting 4-bedroom, 2.5-bath home located in the desirable Henlopen Landing community of Lewes. Step into the Two-Story Foyer & you are greeted with gleaming Hardwood Floors. A Formal Dining Room is off of the Foyer, which also has access to the Kitchen. The Great Room boasts Vaulted Ceilings, Recessed Lighting & a Gas Fireplace. The Open concept features a Kitchen that overlooks the Main level and boasts a Pantry, 42 Inch Cabinets, Stainless Steel Appliance Package and a Breakfast Area. Step into the Sunroom which has abundant natural light & a Gas Fireplace.Sliders lead to a Composite Deck, Hot Tub, Fenced area, an Outdoor Shower and gorgeous Pond Views. Lawn is irrigated. The Primary Bedroom with Ensuite can be found on the First Floor, in addition to the Laundry Room. The 1400 square ft Unfinished basement offers excellent storage and future possibilities, with a plumbing rough-in and egress window already in place. Enjoy outdoor living with a deck and awning, hot tub, outdoor shower, irrigation system, and beautiful pond views. Henlopen Landing offers a Clubhouse with Fitness Center, Gathering Rooms, an In ground pool, and Playground. Conveniently located near Route 1, with easy access to Tax Free Shopping, Award Winning Dining, Entertainment, and the beaches of Lewes and Rehoboth!

32900 Ocean Bluff Dr, Lewes

Listing courtesy of Patterson-Schwartz-Rehoboth. Contact:

69 Filly Ln, Lewes
$625,000
Introducing 69 Filly Lane - an exceptional opportunity to build a custom home in Olde Town, one of Lewes’ most desirable new communities. This 0.23-acre unimproved homesite offers a blank slate for a new buyer to create a home tailored to their vision, with no builder tie-in. The location is hard to beat. The homesite is adjacent to the Junction & Breakwater Trail, directly across from the Lewes Public Library, and just a short distance from downtown Lewes, Cape Henlopen State Park, the beaches, shopping and dining. Within the Olde Town community, the lot is conveniently located near the pool and pool house, making it easy to enjoy the neighborhood amenities while staying connected to town and the trail. The community amenities also include a covered grilling and entertaining area, dual sided fireplace and outdoor TV, shuffleboard, bocce and fire pit. With its desirable location and the freedom to build from the ground up, 69 Filly Lane presents a unique chance to create a custom home in the heart of Lewes.

69 Filly Ln, Lewes

Listing courtesy of Jack Lingo - Lewes. Contact:

31593 Janice Rd, Lewes
$88,000
3 Beds ⋅ 2 Baths
The dream of affordable beach living has arrived! Located minutes from the beach and historic Lewes, this home is packed with pluses. It features a spacious master bedroom and bathroom privately located in the rear. The open kitchen, dining, and living room is perfect for entertaining guests before they retire to their coastal quarters. Substantial upgrades to the property include a new HVAC, washer/dryer, ductwork and skirting. Outside, the ample yard has two large sheds for storage and direct access to the Lewes-Georgetown bike trail when you want to connect to nature. As a resident, benefit from hassle-free perks such as an oversized community pool, waste management, and snow removal. Easy access from Route 1 (thanks to the newly added Minos-Conaway Project) and even easier access to Lewes Senior Activity Center adds to its merit. Schedule a showing today and be in your home for the holidays!

31593 Janice Rd, Lewes

Listing courtesy of Patterson-Schwartz-Rehoboth. Contact:

1 Coventry Ln Unit 42025, Lewes
$159,900
2 Beds ⋅ 2 Baths
Sussex East/West is a leased-land, 55-plus* community (*up to 20% of owners may be younger than 55-years-old). Sussex East is located approximately 5.5 miles from the Lewes public beach, with the Cape Henlopen State Park beaches...and the famous Rehoboth Beach boardwalk...not much farther away. This community has a unique location with access to the State Park’s hiking/biking trail via the trail head on Minos Conaway Rd. There have been many updates and renovations to this home, the addition of the living room with vaulted ceiling, New kitchen with quartz counter tops, stainless appliances, new natural gas furnace, central Ac, tankless water heater, All new flooring, updated baths. plus much more. Two pets are allowed in Sussex East, and they have a fenced dog park near the community’s indoor salt-water pool. New pickle ball court, too. (Note: Family & friends may always visit, but rentals are NOT permitted in this community). Leasehold Interest with Lot Rent of approx. $1057/month (Leases renew annually with any increase capped as per 25 Del. C. Ch. 70). The Community Owner requires an Application from the Buyer and all occupants 18-years-of-age or older, with acceptance in the community based on: 1)income verification, 2)Credit bureau score (including debt-to-income ratio), and 3)Clean criminal background check. Leased land properties do not meet the requirements for conventional 30-year mortgages, but financing may be available to qualified borrowers from a few Lenders that specialize in installment/chattel loans for manufactured homes on leased land. Buyer will have a real estate transfer tax (3.75% DMV Doc Fee) as part of their closing costs & a settlement agent fee.

1 Coventry Ln Unit 42025, Lewes

Listing courtesy of SEA BOVA ASSOCIATES INC.. Contact:

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