Homes for Sale with a Guest House in Millsboro, DE

Welcome to relaxed coastal living in this beautifully maintained townhome in The Peninsula on the Indian River Bay. Thoughtfully designed with beautiful finishes throughout, this inviting move-in home offers comfortable living spaces that are equally suited for everyday enjoyment and entertaining. The spacious two story living room creates an impressive sense of openness, complemented by hardwood floors and a wall of windows with a view of the pond. The beautifully appointed kitchen features attractive cabinetry, quality finishes, gas cooking and plenty of workspace, while the separate dining room provides a welcoming setting for meals with family and friends. Generously sized bedrooms offer excellent closet space, including large walk in closets, providing plenty of room for both owners and guests. Step outside to the charming paver patio surrounded by mature landscaping, creating a private and peaceful outdoor retreat. Enjoy views of the pond while relaxing with your morning coffee, dining outdoors or unwinding at the end of the day. Relax and enjoy a low maintenance lifestyle with yard care provided by the HOA. Step outside and experience the Peninsula community, offering world class amenities within a secure gated setting. The clubhouse is the social heart of the community, featuring a full service restaurant with indoor and outdoor dining, billiards, wine and game rooms, men’s and women’s lounges, a pro shop, putting greens, driving range, bocce courts, and the renowned Jack Nicklaus golf course. Just beyond, Lakeside Village offers an exceptional wellness and recreation experience with a state of the art fitness center, indoor pool, adult outdoor pool, wave pool, and activity pool. Enjoy poolside dining throughout the summer, the popular Tiki bar, fitness classes, weight room, hot tubs, sauna, spa spaces, and a game room. Outdoor amenities continue with tennis, pickleball, a dog park, community garden, nature center, bay beach, fishing pier, and miles of scenic walking trails. A vibrant social calendar of year round events creates endless opportunities to connect and build lasting friendships. Capital contributions to the PCA of 0.5% of the sales price and $750.00 condo applies. Club membership is required with three available levels. Please see disclosures for full details. Some photos have been virtually staged to help illustrate the home's possibilities.

24303 Blue Crab Ave, Millsboro

Listing courtesy of Compass. Contact:

$239,900

3 Beds ⋅ 2 Baths

PRICE IMPROVEMENT - GET YOUR COASTAL RETREAT AND ENJOY THE HOLIDAYS BY THE BAY! NO LAND LEASE - NEW HVAC (2024) - NEW ROOF (2025) - NO HOA Nestled in the charming Oak Orchard Community, this delightful 3-bedroom, 2-bathroom home offers a perfect blend of comfort and style. The property showcases a traditional coastal architectural interior design, enhanced by modern upgrades, including shiplap walls. Step inside to discover an inviting open floor plan, where the family room seamlessly connects to the kitchen and dining area, perfect for gatherings and everyday living. The upgraded countertops and luxury vinyl plank flooring add a touch of elegance, while the walk-in closet in the master bedroom provides ample storage. NO LAND LEASE - NEW HVAC (2024) - NEW ROOF (2025) - NO HOA Enjoy the serene surroundings with water access to the beautiful Indian River Bay, perfect for kayaking or fishing enthusiasts. PUBLIC BOAT RAMP IS 5 MINUTES DOWN THE ROAD. The expansive outdoor deck is perfect for entertaining and enjoying the water life! Mature trees decorate the fully fenced yard. There's even a Fig Tree. Oak Orchard community is known for its friendly atmosphere, neighborhood walks, convenient local restaurants, grocery stores, boutiques, gym, AUCE crabs, local nightlife. With easy access to essential amenities and the natural beauty of the Bay, this home is a true gem for those seeking a peaceful yet connected lifestyle. "As Is" Condition! EMBRACE THE EXCLUSIVE LIFESTYLE THAT OAK ORCHARD COMMUNITY OFFERS. WHERE COASTAL LIVING MEETS MODERN CONVENIENCE. ITS QUIET, ITS QUAINT, IN A COMMUNITY ON THE INDIAN RIVER BAY! THIS IS MORE THAN A HOME, ITS AN OPPORTUNITY TO LIVE NEAR THE WATER AND ENJOY THE COASTAL LIFESTYLE!

28320 Forest Dr, Millsboro

Listing courtesy of Elevated Real Estate Solutions. Contact:

$299,000

3 Beds ⋅ 3 Baths

Stunning, 3-bedroom, 2.5-bathroom coastal villa offering the perfect blend of modern luxury and effortless, low-maintenance condominium-style living. The open-concept main level features professional designer-selected Luxury Vinyl Plank (LVP) flooring, a beautiful family room, and a sunlit sunroom ideal for relaxation. The gourmet kitchen is a chef's dream, complete with a spacious island, granite countertops, premium stainless steel appliances, and gas cooking. For ultimate convenience, the home boasts a highly desirable first-floor owner's suite, alongside elegantly tiled bathrooms. Main level laundry with washer, dryer. Step outside to your private stone patio, perfect for outdoor dining and entertaining, or utilize the attached one-car garage for parking and storage. Located in a premier community featuring a resort-style pool, you will enjoy seamless access to local shopping, dining, outdoor recreation, and quaint downtown Millsboro, all while being just a short drive from the pristine Maryland and Delaware beaches.

19202 Sandstone Ln Unit 3004, Millsboro

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$499,000

5 Beds ⋅ 4 Baths

Skip the builder's wait — and the builder's upgrade prices. Built in 2024 and ready today, 24156 Hammerhead Dr offers five bedrooms and a main-level primary suite in Stonewater Creek, with the fenced yard, window treatments, and finishing touches already in place. The main level is designed for both everyday living and entertaining, with an office featuring built-in shelving, and an open-concept living room and kitchen with decorative pendant lighting over the island, granite countertops, and a gas range. A custom upgraded pantry provides additional storage, while sliding doors offer easy access to the fenced rear yard. The main-level primary suite features a spacious walk-in closet, an ensuite bathroom with a stall shower, and a private water closet — a layout that works beautifully for multigenerational living or long-term guests. Upstairs, four additional bedrooms, two full bathrooms, a spacious loft, and a dedicated laundry room provide plenty of room for family, guests, or flexible use. An attached front-entry garage adds convenience and storage. Stonewater Creek residents enjoy a community pool, clubhouse, fitness center, and playground, with shopping, dining, and grocery stores conveniently nearby. This home is in the Cape Henlopen School District, served by Love Creek Elementary, Beacon Middle, and Cape Henlopen High School. Nearly new, thoughtfully finished, and ready now: this is the space of a new build, without the wait.

24156 Hammerhead Dr, Millsboro

Listing courtesy of Keller Williams Realty. Contact:

$575,000

3 Beds ⋅ 2 Baths

Water Access! Coastal living starts here tucked away on a quiet cul-de-sac in the sought after waterfront community of Winding Creek Village. Situated on .75 acres with private community boat ramp access to Guinea Creek and the Rehoboth Bay, this property offers the space, privacy, and setting that make Coastal Delaware living so appealing. No lot rent or land lease. The 3 bedroom, 2 bath home is designed for enjoying both the indoors and out. The primary bedroom features sliding doors opening to the rear deck, while the all-season room just off the main living area also opens to the deck. An awning provides shade and creates a comfortable outdoor space for relaxing, entertaining, or simply enjoying the peaceful surroundings. A new HVAC system installed in 2025 adds modern comfort and efficiency, while a water filtration system provides added convenience and improved water quality. The unfinished second floor bonus room offers valuable flexibility and storage, with the potential to become a future guest space, game room, home office, studio, or additional living area. A separate detached artist studio provides even more space for hobbies, creative pursuits, a workshop, home office, or private retreat. For those drawn to the Coastal Delaware lifestyle, this location delivers. Spend the day on the water, enjoy a round of golf, explore local dining, or head to the beach—all within easy reach. Whether you're looking for a full time residence, second home, or beach getaway, this is a truly unique opportunity to enjoy coastal living with room to breathe.

440 Grey Gull Ln, Millsboro

Listing courtesy of Coldwell Banker Premier - Lewes. Contact:

$315,000

2 Beds ⋅ 4 Baths

Your new beach home - 1,830sf end-unit townhome - just 17-20mi to the Delaware Beaches and Ocean City! Corner lot in Plantation Lakes - a community rich with resort-inspired amenities - and just a 3-minute walk or bike ride to the North Shore Clubhouse, swimming pool, pickleball courts, tot-lot playground, restaurant, fitness center. * * * Golf memberships available to the Championship Golf course - but NOT mandatory with this particular home, which saves you money! * * * Great floorplan offers 2BRs + flex room, 2 full + 2 half baths. Built in 2019 and recently refreshed. Lots of storage, 9-foot ceilings, luxury vinyl plank flooring throughout the living, dining, kitchen, flex, and bedrooms, ceramic tile in both full baths. Foyer into the first floor with storage and utility closets on one side, attached garage on the other, flex room could function as a 3rd bedroom - attached half bath, sliders out to the fenced rear yard. The main level living area is bright and breezy with large windows, high ceilings. Dreamy kitchen with granite counters, timeless subway-tile backsplash, stainless steel appliaces, breakfast bar, pantry - dining area with sliders to the balcony. Large living room. The 2nd half bath completes the main level. Lovely primary bedroom with vaulted ceilings, walk-in closet, and luxe bath - double-sink, granite-topped vanity, tile shower. Nice-sized guest bedroom with roomy closet. 2nd full bath with tub/shower combo. Laundry room with a washer and dryer completes the home's interior. Relax or entertain on your balcony or private, fenced yard. Unlike many properties in Plantation Lakes, this home *doesn't* include a mandatory deeded golf membership, resulting in significantly lower HOA fees, while still enjoying the community’s wealth of amenities and activities. Vacation at home in one of two outdoor pools, splash fountain, clubhouses, walking paths, fitness centers, pickleball and volleyball, tons of social events. The Landing Bar & Grille at Plantation Lakes - easily accessible from the clubhouse - is a relaxed atmosphere to soak in the picturesque views of the surrounding landscape while taking in drinks or a meal with friends. Fully-stocked golf pro shop. Quick 17-20mi to the beloved Delaware Beaches or Ocean City - each boasting its own unique charm and vibe - from world-class dining to watersports - sandy beaches, boardwalks, tax-free shopping, nature trails. A paradise for nature lovers, sports enthusiasts, and anyone looking for adventure - boating, fishing, crabbing, exploring state parks, lush local history, arts and culture, unique boutique shopping - the list goes on! Miles of ocean beaches, tidal bays, rivers, and woodlands to be enjoyed. Tax paid to the Town of Millsboro for 7/01/26-6/30/27 is $1965.40 -- which includes the $822.80 town property tax + $1142.60 for the SDD - special development district - charged to Plantation Lakes through 2048. Sizes, taxes, distances approximate.

36063 Auburn Way, Millsboro

Listing courtesy of EXP Realty, LLC. Contact:

$259,000

3 Beds ⋅ 2 Baths

Charming Community Pines at Long Neck — Low HOA & You Own the Land! Bring your vision and creative touches to this spacious 3-bedroom, 2-bath Class C home in the desirable Community of Pines at Long Neck. This home offers a comfortable layout, great features, and plenty of potential for someone ready to add their own personal touches. A handicap-accessible ramp provides easy entry, along with a side deck that’s perfect for relaxing outdoors. Inside, you’ll find a spacious kitchen with plenty of cabinet storage and an eat-in area. A separate sitting room just off the kitchen offers flexible space that could be used as a home office, TV room, craft room, or whatever fits your lifestyle.The living area features a cozy gas fireplace, while the private driveway provides convenient off-street parking.This property is being offered as part of an Estate Sale and is being sold AS IS. The home needs TLC, making it a great opportunity for someone looking to bring their ideas, make improvements, and create a home of their own. Enjoy low HOA fees—and you own the land! Located in a convenient Long Neck area close to golfing, shopping, restaurants, and just a short drive to the beaches. Bring your vision and explore the possibilities! This home has been Winterized.

75 White Pine Dr, Millsboro

Listing courtesy of Mann & Sons, Inc.. Contact:

$265,000

3 Beds ⋅ 2 Baths

Welcome to 3306 Caitlins Way, a recently renovated 3-bedroom, 2-bath third-floor end unit in Millsboro! Fresh updates, abundant natural light, and a spacious open floor plan make this condo truly move-in ready. The beautifully updated kitchen features white cabinetry, butcher-block countertops, stainless steel appliances, updated hardware, and a large center island with plenty of room for gathering and entertaining. Fresh neutral finishes and updated flooring carry throughout the main living spaces, creating a bright, clean, and cohesive feel. As an end unit, the condo benefits from additional windows and natural light. The spacious living area opens to a screened porch with an adjoining open-air deck, giving you the best of both worlds—an inviting covered space for relaxing or dining and an open deck for soaking up the sunshine and fresh air. The home features three generously sized bedrooms and two full baths, including a spacious primary suite. A separate in-unit laundry area with a stacked washer and dryer adds everyday convenience. Located on the third floor with no unit above, this end unit offers added privacy along with the ease of low-maintenance condo living. Conveniently located near shopping, dining, everyday conveniences, and Delaware’s beaches and coastal attractions, it offers an ideal combination of space, updates, and location. Whether you're looking for a primary residence, second home, or coastal getaway, 3306 Caitlins Way is refreshed, move-in ready, and waiting for its next owner.

3306 Caitlins Way Unit 3306, Millsboro

Listing courtesy of Iron Valley Real Estate Premier. Contact:

$310,000

2 Beds ⋅ 2 Baths

144 Hudson Aly, Millsboro

Listing courtesy of Century 21 Emerald. Contact:

$259,900

2 Beds ⋅ 3 Baths

Welcome to Plantation Lakes! This well designed 2 bedroom, 2 1/2 bath townhome offers comfortable living with plenty of versatile space and convenient amenities. The lower level features a flexible bonus area that can easily serve as a den, home office, fitness room, or additional living space. The main level offers an inviting open layout with a living room, dining area, and fully equipped kitchen complete with a center island and ample pantry storage. Upstairs, the primary suite features a vaulted ceiling, walk-in closet, and private ensuite bath. A generously sized second bedroom and additional full bath complete the upper level. Enjoy outdoor living on the rear deck, along with the convenience of an attached 1 car garage. Located in the amenity-rich Plantation Lakes community, this townhome offers a wonderful combination of comfort, functionality, and lifestyle. Come discover everything this exciting community has to offer!

20548 Asheville Dr, Millsboro

Listing courtesy of INDIAN RIVER LAND CO. Contact:

$549,900

3 Beds ⋅ 2 Baths

Beautifully maintained and thoughtfully updated, this inviting home offers an exceptional blend of comfortable indoor living and impressive outdoor amenities. An open floor plan and vaulted ceilings create a spacious, light-filled atmosphere throughout the main living areas. The well-designed layout features a comfortable primary suite, two additional bedrooms, a second full bathroom, and a dedicated study, providing plenty of flexibility for everyday living, guests, or working from home. The main living spaces are centered around a striking stone fireplace and flow seamlessly into the kitchen and dining areas, creating an ideal setting for both relaxed evenings and entertaining. The renovated primary bathroom adds a stylish touch to the private primary retreat. Step outside to your own private backyard oasis, where an 8' x 14' inground fiberglass saltwater pool is surrounded by extensive hardscaping, mature landscaping, and a fully fenced rear yard. The thoughtfully designed outdoor spaces offer plenty of room for lounging, dining, and entertaining. Owned solar panels provide an added energy-efficient benefit. With its bright, open interior, attractive updates, private outdoor setting, and resort-like backyard, this home offers a wonderful combination of comfort, style, and easy living. Property is back on market through no fault of the Seller or the Property.

25520 Huntley Glen Ct, Millsboro

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$949,900

4 Beds ⋅ 3 Baths

Nestled on a sprawling 1.42-acre +/- lot in a rural setting, enjoy this custom Cape Cod residence built in 1992 with major upgrades made over the years including a new roof completed this September 2026 and thoroughly maintained. This home offers a blend of elegance and comfort, perfect for those seeking plenty of room. Enjoy the columned, covered front porch. Enter the front door that leads you to a foyer where you will find the living room to the left for some relaxing and quiet conversation, or to the right, the formal dining room which provides for special occasions and is convenient to the kitchen. Straight ahead is the Great room with stone propane fire place, built in entertainment center, hardwood floors and easy access to the screen porch, or doors leading you to the amazing back yard. The heart of the home is a gourmet kitchen, featuring upgraded countertops, a spacious island, and stainless steel appliances, including a commercial range. The kitchen flows into the great room, ideal for entertaining, The residence features four generously sized bedrooms, including a first floor primary suite complete with a room size walk-in closet and a spa-like bathroom featuring a jetted tub and a walk-in shower. For leisure and relaxation, the home features two inviting fireplaces, creating a cozy ambiance both inside and outside. A dedicated 2nd floor Game room/bar area enhances the entertainment experience with its own set of stairs, separating you from the additional 3 bedrooms upstairs. The exterior of the property is equally impressive, showcasing extensive hardscaping, lush landscaping, and a personal in-ground pool surrounded by a tranquil setting. Enjoy outdoor living with multiple patios, a screened porch, and an recently updated (2025) deck, perfect for unwinding in the hot tub, enjoying the pond or outdoor dining with built in BBQ grill. Convenient outdoor shower, kids play house, and more making it an entertainer's paradise. Additional features include a three-car attached garage with added storage, a detached 3 car garage with 2nd floor storage unless you choose to finish area off for something special, and a pool equipment shed, all providing abundant storage options. This home offers a unique blend of privacy and accessibility, with road frontage and landscaping that enhances its charm. where every detail has been thoughtfully planned out. This residence is not just a home; it's a sanctuary that invites you to indulge in simply the finer things in life. Easy to view so call today.

30352 Cordrey Rd, Millsboro

Listing courtesy of BURTON REALTY INC. Contact:

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