Homes for Sale with a Guest House in Lewes, DE

The ULTIMATE condo experience in Historic Lewes!!! Imagine walking to any amenity in town with just steps away to the beach, all easily within walking distance and close to every shop, store, bike trail, State Park, and restaurants of choice. What a RARE opportunity to own a unit that rarely comes on the market. The condo is practically turn-key and ready for new owners to enjoy the warm summer days or the cool nights of the off-season. Each bedroom aside from one has its own en-suite bathroom for optimal privacy and a powder room for all guests to enjoy. Featuring an extra large open floor plan, spacious primary bathroom with jacuzzi tub, large covered balcony so you never have to worry about rain, and private elevator, this condo screams luxury at its finest! Never worry about finding parking, waiting in lines or traffic as this condo is at the Lewes heart's center for summer fun and enjoyment. The condo association already has flood insurance and ground rent included in the dues and pays these dues as a whole building. There is a kayak rack and storage unit in the back of the condo to store all beach chairs and toys. Truly carefree luxury living with a lovely coastal vibe. SELLERS ARE OFFERING TO PAY 2 YEARS OF CONDO FEES FOR POTENTIAL BUYERS!

404 E Savannah Road Unit 202, Lewes

Listing courtesy of Patterson-Schwartz-OceanView. Contact:

$1,849,999

6 Beds ⋅ 6 Baths

Introducing an exceptional new construction custom home by Sienna Homes, thoughtfully designed to deliver approximately 5,500 square feet of sophisticated living space in the sought-after Olde Town at White’s Pond community of Lewes. Offering 6 bedrooms, 5 full bathrooms and 1 powder room, this impressive residence pairs striking architectural details with elevated finishes and a floor plan designed for both everyday living and effortless entertaining. From the moment you enter, soaring ceilings, engineered wood flooring and abundant natural light create an immediate sense of scale. The dramatic two-story living room serves as a stunning centerpiece, featuring cathedral ceilings and expansive Andersen 100 Series windows. Thoughtful architectural details and an open-concept design create a seamless flow throughout the home’s main gathering spaces. At the heart of the home is a showstopping chef’s kitchen anchored by an impressive 9-foot island with Taj-Mahal Quartzite waterfall countertops. Premium ZLINE stainless steel appliances elevate the space, while generous cabinetry and sophisticated finishes offer the perfect balance of beauty and function. A separate butler’s pantry complete with its own dishwasher and refrigerator provides additional prep and storage space, making entertaining on any scale effortless. Designed with flexibility and luxury in mind, the home features two primary suites. The main-level primary suite creates a private retreat with the added convenience of its own dedicated laundry room. Upstairs, a second primary suite provides another beautifully appointed escape, while a second-floor laundry room adds convenience for the home’s additional bedrooms. With six bedrooms and five-and-a-half baths, the expansive layout offers abundant space for guests, home offices, recreation and multigenerational living while maintaining privacy. Carefully selected finishes and custom details complement the home’s impressive proportions throughout. The exterior continues the home’s commitment to quality with Hardie® board siding, Andersen® 100 Series windows, a two-car garage and outdoor shower—the perfect addition for life at the Delaware coast. Beyond the home, Olde Town at White’s Pond offers a lifestyle equally as impressive as the residence itself. The picturesque 85-homesite community is nestled alongside the 16-acre White’s Pond and offers direct access to the Junction & Breakwater Trail, providing miles of opportunities for walking, running and biking between Lewes and Rehoboth Beach. Residents enjoy an exceptional collection of community amenities including a pool and cabana, bathhouse, outdoor kitchen, outdoor fireplace and fire pit, lounge area, shuffleboard and bocce ball courts. Even better, Olde Town places you within one mile of Lewes Beach, Cape Henlopen State Park, and the restaurants and shops of downtown Lewes—bringing together the privacy of a luxury residential community with remarkable access to everything that makes coastal Lewes so special. 59 Filly Lane isn’t simply new construction—it’s a custom luxury residence designed for elevated coastal living, where exceptional craftsmanship, impressive scale and one of Lewes’ most desirable locations come together. Renderings are for illustrative purposes and may depict furnishings, landscaping, finishes or other features that are not included or are subject to change.

59 Filly Ln, Lewes

Listing courtesy of KW Empower. Contact:

$148,750

3 Beds ⋅ 2 Baths

Looking for a great price on a larger home AND $5000 to use as you'd like? With 1848 sq ft, a great layout, private lot, a pool-side location in Lewes' premier waterfront marina community, and $5000 to use for decorating, furniture, or even your closing costs, you need to come see this one! This spacious 3 bedroom, 2 bath doublewide has been refreshed with new luxury vinyl plank flooring throughout (everywhere but the laundry room), crisp white walls and trim, and new baseboard trim in the living areas. It's a modern canvas ready for your style. The lot is a standout, directly across from one of the community's two swimming pools, with lots of room between neighbors. The huge screened porch has views of the pool and is sure to become your favorite spot for morning coffee, summer evenings, or entertaining friends and family. Inside, you'll find two large living areas: a comfortable family room with a stone-faced corner gas fireplace next to the kitchen, and an additional living room adjacent to the dining room. The kitchen has plenty of cabinets, a center island, and generous table space, and there's even a separate dining room for gatherings big and small. The split floorplan gives everyone their own space. Two large guest bedrooms, each with a walk-in closet, sit at the back of the home and share a full bath. The primary suite has two closets and an en-suite bathroom with dual vanities. Although the home features its original windows and HVAC system, the price reflects the condition and the seller's $5000 credit at closing could be put toward those updates. You'll have plenty to do without leaving the neighborhood: two swimming pools, tennis and pickleball, basketball, a marina with a boat ramp, and a fishing/crabbing pier. The marina is just a short drive or golf cart ride away. Residents plan and host quite a few clubhouse and community events throughout the year, including game nights, parties, craft fairs, and more. The community offers the best in convenience, too; You're less than 15 minutes from the fun along Coastal Hwy (Rt 1), including the Movies at Midway, restaurants, outlet shopping, and just beyond that, Rehoboth's boardwalk and Lewes' historic downtown. This is a great chance to build equity in an unbeatable location. The land rent includes sewer, trash, and recycling. Residency application required, with approval based on credit and background checks, and verification of income/assets. Hurry! $5000 seller credit is being offered for a sale that closes by Dec 15.

33540 Montgomery Ct, Lewes

Listing courtesy of Keller Williams Realty. Contact:

$585,000

2 Beds ⋅ 3 Baths

Welcome to this beautifully upgraded home in the heart of Lewes, where thoughtful finishes meet a setting that's hard to beat. From the moment you step inside, the quality is unmistakable. The kitchen is a showpiece, with custom cabinetry, gleaming granite countertops, and plenty of workspace for everyday meals or entertaining. The upgrades continue throughout the home, with details that set it apart from the ordinary. Enjoy the convenience of a main-level primary suite, offering easy single-level living with a private retreat just steps from the main living areas. Upstairs, a versatile family room provides extra space to gather, relax, or host guests, and it can easily be converted into a third bedroom to suit your needs. The sun porch is the real star. Bright and inviting, it overlooks peaceful greenspace with sweeping views of the golf course. Whether you're starting the morning with coffee or winding down at sunset, it's a space you'll want to spend every day in. Just minutes from historic downtown Lewes, Cape Henlopen State Park, and the Delaware beaches, this home offers the best of coastal living with a quiet, scenic backdrop. Schedule your private showing today!

34751 Maritime Way, Lewes

Listing courtesy of HomeZu by Simple Choice. Contact:

$175,000

4 Beds ⋅ 2 Baths

Welcome to Angola Beach! If you missed this beauty the first time around, here’s your second chance to make it yours! Whether you’re looking for a second home, an investment property, or a place to enjoy year round, this beautifully renovated 4-bedroom, 2-bath home offers a water view and plenty to love. Step onto the welcoming front deck and into a bright, open living space with coastal style. Luxury vinyl plank flooring leads into the updated kitchen, featuring white cabinets, quartz countertops, stainless steel appliances, recessed lighting, and modern fixtures. Renovations completed in 2024 include a new roof, HVAC, windows, sliding door, kitchen, and bathrooms, along with updated flooring, bedroom carpet, and lighting. All the updates you will need and have the peace of mine with buying this home. The community offers two pools, a marina with boat slips, a fishing pier, kayak storage, boat and RV storage, basketball and tennis courts, playgrounds, and a picnic area by the marina. Enjoy being within walking distance of the marina and a short drive from local restaurants, shopping, and the Rehoboth Beach Boardwalk. Don’t miss your second chance to own a piece of paradise at the shore; schedule your showing before this beauty is gone!

33261 Waterview Ct Unit C-74, Lewes

Listing courtesy of Keller Williams Realty Delmarva. Contact:

$779,000

5 Beds ⋅ 4 Baths

Luxury 5BR Coastal Club Home In Award Winning Community! Welcome to 19151 Cavendish Way, a beautifully appointed 5-bedroom, 3.5-bath twin home in the highly desirable Coastal Club community in Lewes, Delaware. Offering a spacious floor plan, quality finishes, exceptional outdoor living, and an outstanding array of resort-style amenities, this home is ideally suited for full-time living, a second home, or enjoying the Delaware beach lifestyle with the added flexibility of rental income. The thoughtfully designed floor plan features two primary suites, including one conveniently located on the main level, along with three additional bedrooms upstairs. The chef-inspired kitchen features quartz countertops and stainless steel appliances and flows naturally into the living and dining areas, creating a comfortable and inviting space for everyday living and entertaining. The home truly shines when it comes to outdoor living. The large backyard and furnished screened porch provide plenty of space to relax, dine, and entertain. A propane grill and wood-burning fire pit create an ideal setting for summer evenings with family and friends. Additional features include an attached garage with a Level 2 EV charging station, full-size washer and dryer, and plenty of room for family and guests. Resort-Style Living at Coastal Club: Set around a 42-acre nature preserve and 5-acre pond, Coastal Club offers an exceptional combination of natural beauty and resort-style amenities. Residents can enjoy indoor and outdoor swimming pools, an infinity pool with swim-up bar, clubhouse and restaurant, fitness center, tennis, pickleball, bocce, game room, dog park, walking trails, and more. Whether you're starting the morning with a workout, spending the afternoon at the pool, enjoying the community trails, or relaxing at home, Coastal Club offers an amenity-rich lifestyle designed for enjoyment throughout the year. * An Exceptional Lewes Location 19151 Cavendish Way is conveniently located less than 5 miles from Historic Downtown Lewes, approximately 6 miles from Lewes Beach, 7 miles from Cape Henlopen State Park, and 8 miles from Rehoboth Beach. Enjoy the charm of Historic Lewes with its waterfront setting, boutique shops, galleries, and excellent restaurants, while also having easy access to beaches, state parks, boating, fishing, shopping, dining, and the many attractions of Coastal Delaware. Added Rental Flexibility: For owners who want the flexibility to offset some of the costs of ownership, Coastal Club permits weekly vacation rentals. This home also has an established vacation-rental history, which is available upon request. The home's five-bedroom layout, two primary suites, generous gathering spaces, screened porch, backyard, and extensive community amenities make it well suited for visiting family and guests as well as vacation renters. Buyers can enjoy the home themselves while retaining the option to rent it when their plans allow. Property Highlights: 5 Bedrooms | 3.5 Baths Two Primary Suites Main-Level Primary Suite Chef-Inspired Kitchen Quartz Countertops & Stainless Steel Appliances Spacious Open Living Areas Large Backyard Furnished 2-Story Screened Porch Propane Grill & Wood-Burning Fire Pit Attached Garage Level 2 EV Charging Station Coastal Club Resort-Style Amenities Indoor & Outdoor HEATED Pools Infinity Pool & Swim-Up Bar Tennis | Pickleball | Fitness Center | Bocce Clubhouse & Restaurant 42-Acre Nature Preserve & 5-Acre Pond Convenient to Downtown Lewes, Cape Henlopen & Rehoboth Beach Whether you're looking for a primary residence, second home, or beach retreat, 19151 Cavendish Way offers the space, comfort, amenities, and location to enjoy everything that makes Lewes and Coastal Delaware special—with the added benefit of rental flexibility.

19151 Cavendish Way, Lewes

Listing courtesy of Keller Williams Realty. Contact:

$685,000

3 Beds ⋅ 3 Baths

Offering $10K in buyer incentives!! Welcome to the best-value, never-lived-in model home, ideally situated on a premium pond-front lot in the amenity-rich Chase Oaks community of Lewes—just a five-minute walk from your doorstep to community amenities. Thoughtfully designed and impeccably finished, this exceptional residence features more than $267,000 in carefully curated upgrades (i.e. complete options sheet in documents section), delivering a level of quality and craftsmanship that would be both difficult and costly to replicate with new construction today. The open-concept, two-level floor plan effortlessly blends sophistication with everyday comfort. The main level is anchored by a chef’s kitchen showcasing a large center island, upgraded cabinetry, premium quartz countertops, and a professional-grade appliance package. The kitchen flows seamlessly into the dining area and family room, creating an inviting setting for entertaining and daily living. This central living space is a true showpiece, highlighted by shiplapped ceilings with exposed beams, custom trim work, and designer lighting throughout. Just beyond, the screened porch offers serene pond views and features a stacked-stone gas fireplace—an ideal retreat for year-round enjoyment. The primary suite is privately tucked away off the family room and designed as a relaxing sanctuary, complete with a sitting area, porch access, a spa-inspired bath, and a spacious walk-in closet. A secondary bedroom with a shared hall bath is located at the front of the home, offering flexibility for guests or family. An additional flex space on this level is perfect for a home office, library, or additional living room. The upper level expands the living space with a generous bonus room, third bedroom, and full bath—perfect for visitors, hobbies, or additional entertaining. Additional highlights include upgraded luxury vinyl plank flooring on both levels, a convenient drop zone with built-in cubbies, a main-level laundry room, and a two-car garage. Chase Oaks offers an exceptional location just minutes from historic downtown Lewes and Delaware’s pristine beaches, along with resort-style amenities that elevate everyday living. Residents enjoy a beautifully appointed clubhouse with a great room and built-in bar, a fully equipped fitness center, pickleball courts, and a stunning pool with cabanas and a community fire pit. With its premium finishes, tranquil pond-side setting, and immediate availability, this remarkable property presents an opportunity not to be missed as a primary or investment home.

30019 Chase Oaks Dr, Lewes

Listing courtesy of Compass. Contact:

$95,000

3 Beds ⋅ 2 Baths

Coastal Living at Its Best! Enjoy the best of the Delaware beach lifestyle in this charming mobile home conveniently located near Lewes and the beautiful Delaware beaches. This home offers comfortable living with an inviting layout, a great opportunity for a beach retreat, vacation home, or year-round residence. Enjoy easy access to beaches, shopping, dining, boating, and all that Lewes and the surrounding coastal area have to offer. A wonderful opportunity to own a home minutes from the beach at an affordable price!

16301 Grandview St, Lewes

Listing courtesy of The Parker Group. Contact:

$2,500,000

EXTRAORDINARY OPPORTUNITY IN THE HEART OF DOWNTOWN HISTORIC LEWES! Situated in a high-visibility location along Savannah Road, this landmark 6,089 total sq. ft. transformed Victorian property seamlessly combines timeless coastal elegance with high-capacity commercial infrastructure. Rich in local history, this distinctive Queen Anne–style house was originally built for Johnston, a noted diver and salvager of shipwrecks, by his business partner, contractor William H. Virden. The home's architectural character includes an ornate piazza and an elaborate interior staircase crafted from quartersawn red oak. A mid-twentieth-century owner was Otis H. Smith, longtime mayor of Lewes from 1950 to 1968 and head of Fish Products Company, then the town's largest employer. After deteriorating into a rundown rental property by the 1970s, the historic home was subsequently restored and is currently occupied by a business operating under the name "Harvard House." Boasting 4,012 sq. ft. of primary space across multiple levels along with an additional 2,040 sq. ft. lower level for storage, prep, laundry, and operational support, the footprint offers unmatched scale and versatility. Currently configured as an upscale 105 seat restaurant, the main floor features light-filled dining rooms with hardwood flooring, skylights, a full custom bar, and a charming wrap-around porch with a gazebo area for outdoor seating. Culinary operations are supported by a fully functional kitchen setup featuring a modern, fully integrated dumbwaiter, a convenient modern improvement that serves as a charming nod to classic Victorian architecture (please note: restaurant equipment does not convey with the real estate, but is available for purchase separately). The upper floors offer numerous private rooms, providing endless adaptability. Whether you envision continuing its success as a premier restaurant, converting it into a luxury Bed & Breakfast, establishing high-end retail boutiques, or housing corporate and professional suites, this trophy asset is ready for its next chapter. Rare properties of this distinction and prime location seldom become available; bring your vision to Downtown Lewes today!

210 Savannah Rd, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$2,990,000

5 Beds ⋅ 5 Baths

ELEVATED COASTAL LIVING IN ANGLERS NEST! This expanded and heavily upgraded custom home delivers luxury across three expansive levels. Backing to serene wetlands just a short stroll from the beach, canal, and Historic Lewes dining and shopping, the residence boasts striking coastal contemporary curb appeal and beautiful views. The light-filled, open-concept floor plan features high-end finishes throughout, including rich hardwood floors, exposed ceiling beams, 9ft+ ceilings, and three gas fireplaces. The chef’s gourmet kitchen is equipped with a luxury double-oven six-burner gas range, a grand waterfall island, custom cabinetry, a walk-in pantry, and top-of-the-line stainless steel appliances. Designed for effortless indoor-outdoor living, all three levels feature incredible outdoor spaces, including multiple private balconies, a screened porch, and an oversized deck ideal for taking in the coastal views. Accommodations include a primary suite complete with sitting area, gas fireplace, custom walk-in closets, and spa-inspired tiled bath - along with four additional spacious bedrooms. Further highlighted by a ground-level office, recreation room, mudroom with custom built-ins, tankless hot water, an elevator, and a 2-car garage, this exceptional residence combines unmatched convenience with coastal style. Property is being sold "AS-IS". Call and schedule a showing today!

212 Grey Plover Ct, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$420,000

3 Beds ⋅ 3 Baths

Beautiful pond views and a spacious, thoughtfully designed layout highlight this three-bedroom, two-and-a-half-bath townhome in Lewes. Ideally positioned overlooking the community pond, the home offers inviting indoor and outdoor spaces designed to take full advantage of its peaceful setting. A welcoming entry foyer opens to a generous main level with hardwood flooring and comfortable spaces for everyday living and entertaining. The large table-space kitchen features ceramic tile flooring, abundant counter space, ample cabinetry, and breakfast bar seating, while its open connection to the expansive family room keeps the entire space bright and inviting. A gas fireplace provides a warm focal point for the family room. At the rear of the home, a gorgeous sunroom showcases the pond setting with a wall of windows overlooking the water. Ceramic tile flooring makes this versatile space ideal for casual dining, morning coffee, reading, or simply relaxing while enjoying the view. A rear entry leads directly to the outdoor patio, extending the living space outdoors and providing another wonderful spot to enjoy the pond. A convenient powder room completes the main level. Upstairs, the spacious primary suite includes a private en suite bath and walk-in closet. Two additional bedrooms share a full hall bath, while a conveniently located upper-level laundry area keeps everyday tasks close to all three bedrooms. Located in Lewes, this home puts the best of coastal Delaware within easy reach. Enjoy convenient access to historic downtown Lewes with its locally owned shops and restaurants, the beaches along the Delaware Bay, Cape Henlopen State Park, scenic biking and walking trails, and the area's many opportunities for boating, fishing, and outdoor recreation. Rehoboth Beach, Coastal Highway shopping, dining, entertainment, and everyday conveniences are also just a short drive away, making this an ideal home base for enjoying the Delaware coast.

17434 Taramino Pl, Lewes

Listing courtesy of Northrop Realty. Contact:

$1,795,000

4 Beds ⋅ 3 Baths

Live and Love the Beach! Just steps from a tranquil beach, this charming 4-bedroom, 2½-bath home sits on a desirable corner lot and offers the perfect combination of a beach getaway and investment opportunity. Renovated in 1995 and offered turnkey, the home comes fully furnished, including kitchen supplies, pots and pans, and linens. The second floor features two bedrooms and a full bath with a skylight and relaxing soaking tub. The first floor has two additional bedrooms, 1½ baths, a living room, kitchen/dining area, family room, den, and a rear screened porch. There is also a deck, outdoor shower, shed for beach gear, and a garage for additional storage. A double driveway provides convenient off-street parking. This property has an excellent rental history and strong rental performance, making it an attractive investment opportunity. Or, make it your own private beach retreat and enjoy it with family and friends. Located just minutes from the heart of Lewes, you'll have easy access to fine dining, unique shops, historic sites, and all that this charming coastal town has to offer. Bring your beach chairs and start enjoying the Delaware coast! PLEASE NOTE:Tax record is incorrect as it only has square footage for the original cottage. So owner and agent believes Zillow value is incorrect because they are using the tax records for size. Land lease-cost is city taxes

12 New Hampshire Ave, Lewes

Listing courtesy of RE/MAX Associates. Contact:

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