Homes for Sale with a Guest House in Lewes, DE

A Rare and Beautiful Waterfront Setting in Bayfront at Rehoboth Some homes are special. Others offer a setting that takes your breath away. Set on arguably one of the most beautiful and coveted homesites in Bayfront at Rehoboth, this exceptional three-bedroom, 2.5-bath rancher embraces the natural beauty of the Delaware coast, with protected wetlands and the tranquil waters of Rehoboth Bay as its extraordinary backdrop. Here, the scenery is ever-changing, wildlife abounds, and the feeling of serenity is unmistakable. Inside, soaring ceilings and beautiful hardwood floors create an inviting first impression, while the home's thoughtful design celebrates its remarkable surroundings. From the comfortable sitting room and dining area to the enclosed porch and primary bedroom, captivating views invite you to pause, unwind, and savor the beauty just beyond your windows. The spacious kitchen is designed for everyday living and effortless entertaining, featuring an oversized island with generous prep space and three ovens—perfect for hosting family and friends. Quality craftsmanship and timeless coastal architecture distinguish Bayfront at Rehoboth, where homes are held to a higher architectural standard. Fiber-cement Hardie Plank siding, attractive stone or lattice foundations, and side-load garages contribute to the community's cohesive, understated elegance. This home features a two-car side-load garage, along with interior and exterior storage closets for added convenience. Yet what makes this property truly exceptional extends well beyond its walls. Overlooking the north shore of Rehoboth Bay, Bayfront at Rehoboth is a remarkable coastal enclave surrounded by forest, wetlands, and the rhythms of nature. Ospreys soar overhead, herons grace the shoreline, and foxes and deer wander through the surrounding landscape. With community water privileges and opportunities to enjoy the beauty of Rehoboth Bay, this is a place where morning light dances across the water, evenings invite you to linger, and the natural world becomes part of your everyday experience. The community's amenities make embracing the coastal lifestyle easy. Enjoy a private sandy beach, a winding wooden boardwalk with golf cart access, scenic walking and biking trails, and a private gazebo with kayak and canoe storage and a launch area. Horseshoe pits and sand volleyball courts offer additional opportunities for recreation and connection. Just a short walk from the home, the community pool occupies a spectacular setting at the edge of the wetlands, with unobstructed views of Rehoboth Bay. A children's playground and play area near the pool add even more appeal for families. The thoughtfully situated community center, complete with fitness facilities and meeting rooms, provides a welcoming space for gathering and recreation. Exceptional amenities and outstanding value go hand in hand at Bayfront at Rehoboth. The HOA fee is just $300 per month and includes lawn care and mowing, maintenance of the community's five ponds, common-area maintenance, snow removal, trash collection, four seasonal leaf pickups per year, and two fertilizer applications for each lot annually. It's an impressive package of services and amenities designed to help you spend less time on property upkeep and more time enjoying the setting, the community, and the coastal lifestyle. Beautifully situated, thoughtfully designed, and surrounded by extraordinary natural beauty, this is more than a home—it's an invitation to experience the Delaware coast at its most peaceful and picturesque. For those who appreciate the rare combination of captivating views, refined coastal living, community amenities, and a genuine connection to nature, this exceptional Bayfront at Rehoboth property is a place to truly call home.

23340 Horse Island Rd, Lewes

Listing courtesy of Jack Lingo - Rehoboth. Contact:

$474,900

3 Beds ⋅ 2 Baths

Your coastal getaway awaits on an exclusive corner property in Angola by the Bay with Fee Simple Ownership! The property includes two lots, with an oversized, fenced-in back yard. This gleaming residence features extensive improvements completed this year!, including fully renovated kitchen and bath spaces, soapstone countertops, new Foyer ceramic tile, water heater, professional interior painting, new electrical outlets throughout, a new patio and fire pit, a new asphalt-paved driveway, a new garage door, and vinyl fencing around the backyard. A comprehensive home energy-efficiency audit was completed in 2026, followed by crawl-space encapsulation, blown-in insulation in both attics, insulated pipes and vents, and foam sealing at all exterior-wall utility penetrations. The welcoming front porch opens to a spacious great room and dining area designed for comfortable gatherings. The bright kitchen flows into a sun-filled sunroom, which leads to an expansive deck spanning the rear of the home and overlooking the generous, fully fenced corner lot. The outdoor space offers a storage shed and ample room for creative landscaping and potential additional improvements. Upstairs, the spacious primary bedroom and elegantly updated bath provide a private retreat, while two additional bedrooms comfortably accommodate family, friends, and guests. Located in the hidden gem of Angola by the Bay, the property provides access to Burton Prong, restaurants, shopping and the pristine Rehoboth Bay. This secure gated community offers a marina, boat launch, tennis courts, playground, shuffleboard, scenic walking pier, active community center, refreshing pool, memorable sunsets, and a variety of community events, including an all-women social group called “The Sea Gals”! Only 9 miles to the Atlantic Ocean and Rehoboth Beach and 10 miles to Savannah Beach in downtown Lewes! You better come see this one before it’s SOLD!!!!

33318 Butternut Ct, Lewes

Listing courtesy of EXP Realty, LLC. Contact:

$589,000

4 Beds ⋅ 2 Baths

Classic charm, light-filled spaces, and a peaceful setting come together in this custom home in The Cove on Herring Creek. Situated on an approximately half-acre cul-de-sac parcel shaded by mature trees, this home features beautiful hardwood floors, ceilings of nine feet or higher, abundant windows, and a thoughtfully designed floor plan with the convenience of main-level living. A new roof in 2026 adds to the home’s appeal, while an irrigation system supplied by a dedicated irrigation well helps maintain the landscaped grounds. A formal dining area flows into spacious living areas, where a centrally positioned gas fireplace creates a welcoming focal point and a natural division between formal and casual gathering spaces. The casual living area opens to a breezy screened porch—an inviting spot for morning coffee, outdoor dining, or unwinding with views of the tree-lined surroundings. The first-floor primary suite offers vaulted ceilings, dual closets, and an en-suite bath. An adjoining flex room, currently used for sewing, provides additional space for a home office, library, or creative pursuits. Upstairs, two guest suites offer comfortable accommodations and added privacy. Located in the waterfront community of The Cove on Herring Creek, this home enjoys access to a large community pond, gazebo, and pool, along with low community fees. Convenient to both downtown Lewes and Rehoboth and situated within the Cape Henlopen School District, this charming property brings together space, character, and access to the best of coastal Delaware!

23463 Osprey Ct, Lewes

Listing courtesy of Jack Lingo - Rehoboth. Contact:

$1,849,999

5 Beds ⋅ 5 Baths

Luxury Coastal Living Redefined in Lewes Elegance, space, and coastal proximity converge at this stunning Fishers Cove residence, ideally situated east of Route 1 within Lewes City limits. Impeccably maintained and barely lived-in, this home pairs architectural drama with everyday luxury. The heart of the home is a light-filled great room featuring soaring two-story ceilings, exposed wooden beams, and a commanding cantilever stone fireplace. Adjacent, the gourmet kitchen serves as the central gathering point, outfitted with premium stainless steel appliances, quartz countertops, custom maple cabinetry, and an oversized four-sided finished island. The main level also hosts a private primary suite complete with a rear extension, angled tray ceiling, two walk-in closets, and a luxury bath. Upstairs, a versatile loft leads to two massive secondary en-suite bedrooms—large enough for king suites—plus two additional bedrooms and ample storage. Step outside to your private entertaining haven, featuring a screened porch and a paved courtyard with a marble-top grilling station, custom stone fireplace, and outdoor shower. Complete with a deep 3-car garage outfitted for beach equipment, smart home automation, and proximity to the Lewes Marina, Cape Henlopen, and downtown Rehoboth, this property represents coastal living at its finest.

151 Jacks Way, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$450,000

3 Beds ⋅ 2 Baths

Welcome to 34432 Spring Brook Ave - Enjoy easy single-level living and exceptional value in the sought-after Villages at Red Mill Pond! Built in 2018, this 3-bedroom, 2-bath home features luxury vinyl plank flooring throughout and an inviting open floor plan designed for comfortable everyday living and entertaining. The gourmet kitchen flows seamlessly into the gathering spaces, while a beautiful stone gas fireplace creates a warm focal point in the family room. The primary bedroom offers a relaxing retreat with a private en suite bath featuring a dual vanity. Two additional bedrooms provide flexibility for guests, a home office, or hobbies. Step outside to the added rear patio and hardscaping—an ideal setting for morning coffee, outdoor dining, or relaxing at the end of the day. A 2-car garage adds convenient parking and storage. Enjoy a community lifestyle with access to two clubhouses, two pools, and a kayak launch, offering plenty of opportunities for recreation and relaxation. As one of the best-priced homes on the market in the community, this is a fantastic opportunity to enjoy single-level comfort and desirable amenities at an attractive price! Schedule your tour today!

34432 Spring Brook Ave, Lewes

Listing courtesy of Coldwell Banker Realty. Contact:

$589,900

3 Beds ⋅ 4 Baths

Welcome home to effortless coastal living. Perfectly positioned on a premier pond-front lot, this impeccably maintained Wheaton Model blends serene water views, architectural upgrades, and resort-style amenities into a true coastal retreat. From the moment you enter the wainscoted foyer, immediate views of the pond draw you into a bright, open-concept layout framed by wide-plank LVP flooring, tray ceilings, and custom crown molding. At the heart of the home sits a gourmet kitchen designed for entertaining, complete with high-end cabinetry, quartz countertops, a four-burner gas cooktop, a timeless tile backsplash, a deep apron-front sink, a massive seating island, and an oversized walk-in pantry. Adjacent to the kitchen, the sunlit great room centers around custom built-in cabinetry with butcher block tops and a striking floor-to-ceiling stone linear gas fireplace. The main-level primary suite serves as a private sanctuary with tray ceilings, dual walk-in closets, and a spa-inspired bath featuring double vanities and a Roman shower. Two additional generously sized bedrooms feature walk-in closets and room for queen beds, complemented by a light-filled flex room or office set behind stylish French doors, three full bathrooms, and a main-level powder room. Outdoor living is centered around breathtaking sunrise pond views from the covered rear porch, leading out to a fully fenced, irrigated yard with ample space for a custom paver patio. A rare attached three-car garage with an expanded driveway provides exceptional storage and parking. Beyond the home, enjoy Headwater Cove’s resort-style community pool, clubhouse, fitness center, firepit, and sports courts—all just minutes from local beaches, marinas, championship golf courses, and dining.

21006 Jenny Ct, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$2,250,000

1144 Savannah Rd, Lewes

Listing courtesy of Jack Lingo - Lewes. Contact:

$899,000

4 Beds ⋅ 3 Baths

Welcome to this beautifully designed 4-bedroom, 3-bath home in the sought-after Coastal Club community, where spacious interiors, thoughtful design, and exceptional resort-style amenities come together to offer the best of coastal living. Perfectly situated on a quiet cul-de-sac with a wooded backdrop and convenient access to the community's scenic walking and biking trails, this home offers a wonderful combination of privacy, comfort, and convenience. Step inside to discover a bright, open floor plan designed for both everyday living and effortless entertaining. Beautiful, engineered hardwood flooring extends throughout most of the first-floor living areas, adding warmth and continuity to the home's inviting interior. The heart of the home is the spacious gourmet kitchen, beautifully appointed with quartz countertops, a tile backsplash, farmhouse sink, pantry, and a large counter-height island with breakfast bar seating. The kitchen flows seamlessly into the generous great room and dining area, creating an inviting gathering space for family and friends. The desirable first-floor primary suite offers a peaceful retreat, complete with a spacious, light-filled bathroom featuring dual sinks, a large fully tiled walk-in shower, and a generous walk-in closet. A dedicated office provides the perfect space for working from home, reading, or pursuing your favorite hobbies. A second bedroom and full bathroom on the main level offer wonderful flexibility for guests or family members who prefer to avoid stairs. Just off the dining area, the expansive three-season porch with WeatherMaster vinyl windows is a natural extension of the home's living space. Whether enjoying a quiet morning, entertaining friends, or relaxing after a day at the beach, this inviting space overlooks the peaceful wooded setting. Step outside to the generously sized, low-maintenance deck and fenced backyard, where you'll appreciate the privacy and natural beauty surrounding the property. One of this home's especially appealing features is its convenient access to Coastal Club's scenic walking, running, and biking trails. A pathway established by the homeowners through the wooded portion of their property connects to the community trail, making it easy to enjoy a shaded morning walk, an afternoon bike ride, or an invigorating run just steps from home. It's a wonderful opportunity to embrace an active outdoor lifestyle without ever leaving the neighborhood. Upstairs, two additional bedrooms and a full bathroom provide comfortable accommodations for family and guests. A very spacious second-floor family room offers endless possibilities as a media room, recreation space, or additional gathering area. You'll also appreciate the generously sized walk-in storage room, providing that hard-to-find extra space for holiday decorations, luggage, and seasonal belongings. Beyond the home itself, Coastal Club delivers an exceptional resort-style lifestyle. The impressive 14,000-square-foot clubhouse features a heated indoor pool, fitness center, yoga studio, locker rooms, billiards and game rooms, meeting spaces, and an indoor bar. Outdoors, residents enjoy two pools, a swim-up bar, waterslide, pirate ship splash zone, bocce ball, tennis, pickleball, shuffleboard, and over three miles of scenic walking trails. The Lighthouse Club adds another inviting gathering destination with a full bar and food and beverage service. Ideally located just minutes from historic downtown Lewes, you'll enjoy convenient access to charming boutiques, wonderful restaurants, Cape Henlopen State Park, and Delaware's beautiful beaches. With its flexible floor plan, desirable first-floor living, exceptional indoor and outdoor spaces, peaceful cul-de-sac setting, and outstanding community amenities, this Coastal Club home offers a truly wonderful opportunity to enjoy the coastal lifestyle you've been dreaming of.

18374 Southampton Dr, Lewes

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

$495,000

4 Beds ⋅ 3 Baths

PRIVATE-ENTRY GUEST SUITE + ONE-LEVEL LIVING + OVERSIZED PRIVATE YARD + LOW HOA! Rarely does a home offer this much flexibility, privacy, and value in one package! This beautifully maintained 4-bedroom, 3-full-bath home in desirable Chapel Green offers nearly 2,400 sq. ft. of easy one-level living, plus a separate private-entry guest/in-law suite with generous parking. Perfect for multi-generational living, an au pair, adult child, extended family, long-term guests, a home office, or your own private retreat, this versatile space gives you options while preserving privacy. The main home features an inviting open layout, fresh paint throughout, eat-in kitchen, sunroom, formal dining room, and comfortable single-level living. An attached 2-car garage and 2018 roof add even more value. Step outside to an oversized, private backyard with room for entertaining, gardening, pets, play, or simply enjoying the outdoors. And the location? You’re directly across from the community pool, clubhouse, and tennis courts, with low HOA fees. Just minutes to Lewes, Rehoboth, the beaches, dining, shopping, and coastal attractions. Flexible. Spacious. Private. Convenient. And priced below appraised value. Homes offering this combination are hard to find 16 Ancient Oak Drive is the one you've been searching for, schedule your showing today!

16 Ancient Oak Dr, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$899,900

4 Beds ⋅ 3 Baths

Here is your opportunity to live in one of Coastal Delaware's most sought-after communities. Welcome to Coastal Club. This beautifully appointed Schell Brothers property features 4/5 bedrooms, 3 baths and an impressive outdoor living area just as lovely and spacious as the inside. With an open and airy floorplan and standout features like 5 in wide plank hand-scraped hickory wood flooring, a main level library w/ glass panel doors (currently used as a 5th bedrm), plantation shutters, closet organizing system in every bedroom and lighted built-ins flanking the fireplace in the great room. The kitchen features a center island, breakfast bar, glass panel cabinetry, a 5 burner gas cooktop, GE Profile stainless appliances and a walk-in pantry. Just off of the garage (w/built in cabinetry) is the laundry room w/LG top load washer/dryer and convenient drop zone. The primary suite is spacious with wood flooring, a tray ceiling and 2 walk-in closets. The primary bath features a walk-in shower, double vanity sink, linen and water closets. Upstairs you will find room for guests to enjoy the huge loft area, 4th bedroom, full bath and a 17 x 21 walk-in attic providing easy storage. Extending the living space to outdoors you will find a lovely screened in porch, deck w/pergola and a sunshade, a paver patio and a fenced yard all overlooking open space and a pond. Enjoy all this vibrant community offers with a host of organized activities, a state of the art fitness center, yoga studio, food and beverage services and an indoor lap pool. The outdoor pool is truly amazing with a swim up bar, water slide and a playful pirate ship. Live minutes from Lewes and Rehoboth Beach, Coastal Hwy, the Outlets and all of the fabulous dining and tax-free shopping.

37058 Sheepscot Rd, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$249,000

3 Beds ⋅ 2 Baths

26 Whitehaven features a well-maintained 28 X 56, 1,700 sq/ft home with three bedrooms, two bathrooms, a 10 x 15 four season sunroom off of the kitchen, and a large living room and dining room. The primary suite has a walk-in tub/shower and a walk-in closet. The kitchen features a walk-in pantry, stainless steel appliances, a natural gas range, built-in microwave, double door refrigerator and a disposal. The 18 x 22 garage with an attic is an added plus. Home has a block foundation. New HVAC was installed in 2023. Tankless water heater. Natural gas. Washer and dryer are included. Garage has a pull down attic with fantastic storage. New windows throughout except the sunroom! The community of Sussex West is less than 6 miles to Lewes Beach. The community has direct access to the Lewes-Georgetown and Breakwater Junction Trail for biking and walking to Lewes and Rehoboth Beach. Cape Henlopen State Park and the Cape May Lewes Ferry are just minutes away from this fantastic location. Drive on or walk on for a beautiful 1 hour, 10 minute ride to Cape May. Community features include a year-round indoor pool, outdoor pool, a pickleball court, a dog park, bocce ball, horseshoe pit and an RV storage lot. Sussex West is a beautifully maintained community that is close to all necessities, shopping, dining, and entertainment.

26 Whitehaven Way Unit 13, Lewes

Listing courtesy of Patterson-Schwartz-Rehoboth. Contact:

$650,000

4 Beds ⋅ 3 Baths

Where Gardens Flourish & Coastal Living Begins - Introducing 75 Gainsborough Drive, a beautifully updated 4-bedroom, 3-bath residence nestled on a lushly landscaped half-acre homesite in the desirable Rolling Meadows community of Lewes, Delaware. Surrounded by mature trees, colorful seasonal gardens, and thoughtfully designed outdoor living spaces, this exceptional home offers an inviting blend of comfort, style, and coastal charm, with two levels of versatile living designed for today's lifestyle. Step inside and discover an impressive open-concept design where cathedral ceilings, abundant natural light, and thoughtful architectural details create a warm and welcoming atmosphere. The spacious living room is anchored by a beautiful gas fireplace framed by a shiplap feature wall, creating a cozy gathering place. Flowing seamlessly into the dining area and expansive family room/sunroom addition, these interconnected spaces offer wonderful opportunities for entertaining while showcasing panoramic views of the surrounding lawn and gardens. At the heart of the home, the gourmet kitchen is both beautiful and functional, featuring granite countertops, abundant 42-inch custom cabinetry with under-cabinet lighting, a stylish tile backsplash, and stainless steel appliances, including a GE Café refrigerator added in 2022. A generous peninsula with breakfast bar seating and an adjoining breakfast room provide inviting spaces for casual meals, conversation, and memorable gatherings. The thoughtfully designed split-bedroom floor plan offers a peaceful retreat in the main-level primary suite. This serene sanctuary features a spacious walk-in closet with custom organization, a beautifully appointed ensuite bath with dual vanities, custom storage cabinetry, and an expansive glass-enclosed shower. Private deck access invites you outdoors to enjoy tranquil garden views and the beauty of the surrounding landscape. Two additional guest bedrooms and a well-appointed full bath occupy the opposite wing of the home, offering comfort and privacy. An expansive laundry and mudroom connects to the oversized two-car garage and provides access to the finished lower level, where an entirely new dimension of living awaits. Featuring a fourth bedroom with its own ensuite bath, two additional flexible living areas, generous storage, and a separate entrance through the garage, this level presents wonderful possibilities for multigenerational living, extended guests, recreation, or a private home office. Outdoor living is equally impressive! Step from the family room onto an expansive paver patio surrounded by lush landscaping, flowering gardens, and mature trees. Thoughtfully arranged areas for alfresco dining, lounging, and gathering around the dedicated firepit create a private outdoor retreat perfect for everything from quiet mornings to lively celebrations. The expansive fenced backyard offers plenty of room for outdoor enjoyment, while established gardens provide endless inspiration for those with a green thumb. Additional highlights include a solar energy system, a tankless water heater installed in 2022, and extensive encapsulated crawlspace areas beneath the main home and addition, complete with lighting and abundant additional storage. Interior painting completed in 2020 and recent exterior power washing further complement this lovingly maintained property. Rolling Meadows offers a wonderful neighborhood setting with a community pool and low HOA fees. Ideally situated just minutes from historic downtown Lewes, Cape Henlopen State Park and its beautiful beaches, Tanger Outlets, exceptional dining, entertainment, and the vibrant resort destinations of Rehoboth Beach and its iconic boardwalk, this location places the best of coastal Delaware within easy reach. Beautifully maintained, thoughtfully updated, and surrounded by nature's beauty, 75 Gainsborough Drive is ready for its next chapter of coastal living. Will you be the author?

75 Gainsborough Dr, Lewes

Listing courtesy of Northrop Realty. Contact:

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