Oak Orchard Homes for Sale

Oak Orchard Homes for Sale

Welcome to Oak Orchard, a charming subdivision nestled in the heart of Millsboro, Delaware, within Sussex County. This serene community is perfect for those seeking a blend of tranquility and modern living, making it an ideal place to call home.

Oak Orchard is renowned for its picturesque surroundings, with lush landscapes and scenic waterways that invite you to explore the great outdoors. Residents here enjoy easy access to the Indian River Bay, where boating, fishing, and kayaking become part of everyday life. The community exudes a friendly atmosphere, perfect for families, retirees, and everyone in between.

When it comes to homes for sale in Oak Orchard, you’ll find a delightful variety of options that cater to diverse lifestyles and preferences. From cozy single-family homes to spacious waterfront properties, each residence is designed with comfort and style in mind. Many homes feature modern amenities, open floor plans, and beautiful outdoor spaces, ideal for entertaining or simply enjoying the peaceful surroundings.

Living in Oak Orchard means you’re just a stone’s throw away from local attractions, including charming shops, delectable dining options, and stunning beaches. The nearby Rehoboth Beach and Bethany Beach offer endless opportunities for sun-soaked days and vibrant boardwalk experiences.

With a welcoming community spirit and an array of homes for sale, Oak Orchard is not just a place to live; it’s a lifestyle choice. Don’t miss your chance to discover the perfect home in this idyllic subdivision—where your dream lifestyle awaits!

Newest Oak Orchard Homes for Sale

3 Beds ⋅ 2 Baths

LOCATION, LOCATION and WATERFRONT this home on the Indian River Bay with its own private pier/dock. Great for docking your boat, sitting and enjoying the views!!! Crabbing off the pier/dock can be fun for all and dinner as well. Year-round living or make it your vacation spot for whenever you need to get away. The waterfront side has a walk out basement where you can sit inside and eat crabs in the A/C while enjoying the view. A MUST SEE to appreciate what this property has to offer. Priced so you can make this your forever home with your choice of upgrades. The 4-season glassed enclosed room with deck is the place to spend most of your time. The views at different times of the day and evening are fantastic! One of a few waterfront properties available on the market. Don’t let this one sell before you schedule an appointment to see. (More photo to come in a few days).

31360 River Rd, Millsboro

Listing courtesy of Jack Lingo - Lewes. Contact: (302) 645-2207

1 Beds ⋅ 1 Baths

This small stick built 1 1/2 story cottage with a detached garage may be the "Get Away Home" you have been looking for to use year round. LOCATION, LOCATION, Location!!! If living in an area with nearby waters for many things to do; this one may be for you! Fishing, boating, crabbing and water sports or just enjoying the nearby views a short distance away. PRIVATE BOAT LAUNCH for a reasonable yearly fee. The Indian River Bay, Atlantic Ocean, Lewes Beach, Cape Henlopen State Park are a short drive as well. Downtown Rehoboth offers the ocean with many quaint restaurants and shops. Historic Downtown Lewes also has quaint restaurants and shopping to enjoy. Don't forget Delaware has NO SALES TAX. Tanger Outlets offers many stores. The Lewes Historic Society on Third Street will take you back in time!! Many miss this neat experience. Head west to Millsboro and there is fresh water fishing, many places to eat and food stores for groceries. Heading south Assateague Island is about an hour away and south of there is Ocean City, MD. Land lease paid annually, this year it is $4,632.00 Please call to schedule your appointment.

28500 Ok Waw Ave Unit #6756, Millsboro

Listing courtesy of Jack Lingo - Lewes. Contact: (302) 645-2207

4 Beds ⋅ 3 Baths

Imagine the possibilities with this to-be-built custom home by award-winning Bay to Beach Builders, known for their Amish craftsmanship and exceptional attention to detail. The Chesapeake offers 2,455 heated square feet of thoughtfully designed coastal living space with 4–5 bedrooms, 3 full baths, a flexible first-floor living area, and an oversized two-car garage, perfectly suited for primary residences, vacation homes, or investment properties. This elevated design features a bright open-concept main living level, spacious owner’s suite, screened porch, and multiple gathering spaces ideal for entertaining and relaxed coastal living. Located on Lot 76 in the desirable Oak Orchard Waterfront Boating Community in Millsboro, Delaware, this 0.2 -acre cleared corner lot offers no HOA, no land lease, and public sewer, with sewer impact fees already paid—representing a savings of nearly $8,000. Enjoy water views, a short walking distance to the community boat ramp, and close proximity to prime Delaware beach destinations, marinas, dining, and shopping. Choose The Chesapeake as shown, or explore a wide variety of floor plans and custom design options to create the perfect home for this exceptional setting that fits your lifestyle and vision. Concept home pending final approvals.

Lot 76 Oak Orchard, Millsboro

Listing courtesy of The Parker Group. Contact: 3022176692

3 Beds ⋅ 3 Baths

Located in the sought-after Oak Orchard Waterfront Boating Community, this new construction opportunity by Bay to Beach Builders offers the perfect blend of coastal charm and modern convenience. Just minutes from Delaware’s premier beaches, this property delivers an enviable lifestyle without the burden of HOA fees or land lease restrictions. Enjoy stunning water views and a short walk to the community boat ramp — ideal for boaters and water lovers alike. Sewer impact fees have already been paid, representing a savings of nearly $8,000. Every home will be built exclusively by Bay to Beach Builders, known for their High-Quality Amish Craftsmanship, thoughtful design, and commitment to custom detail. Whether you envision a year-round residence or a weekend escape, this property sets the stage for your perfect coastal home.

32804 Oak Orchard Rd, Millsboro

Listing courtesy of The Parker Group. Contact: 3022176692

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Joe Sterner

Greetings! I’m Joe Sterner and the Rehoboth Beach area has been home to me since 2003, though my connection to DelMarVa goes back to childhood summers in Ocean City, MD. Originally from Central PA, my partner and I first made coastal Delaware our second home while we owned and operated a national internet marketing company. After selling that successful business in 2013, we moved permanently to Rehoboth Beach, where we purchased The Homestead Bed & Breakfast. As a local bed and breakfast owner, I get to help guests discover coastal Delaware every day. What makes the Delaware beaches truly unique is the lifestyle—and helping people navigate the different communities and towns here is something I genuinely enjoy. My process is simple: I listen carefully to understand your goals, lifestyle, and what you value, and then work with my exceptional team to make your move as seamless as possible. From industry-leading marketing to a vast network of trusted partners, I take care of everything to ensure your move is a success. In addition to my work as an innkeeper and a realtor, I also volunteer on the Clear Space Theatre board as vice-chair. In this role, I’ve had the pleasure of collaborating with people from across our state to help support the arts right here in Rehoboth Beach. To me, the arts are what keep our community vibrant—so if you like theatre or are just curious about what’s happening in town, please don’t be afraid to ask! Additionally, having personally bought and sold millions of dollars in commercial property (both real estate and IP), I regularly work with entrepreneurs and savvy investors to navigate the buying and selling process. When I’m not selling real estate or making breakfast for our B&B guests, you’ll find me hosting dinner parties, surf fishing with friends, tending to the vegetable garden, rooting for my favorite football team in the fall, or simply enjoying a dirty martini in our courtyard. My pledge to you as your agent is the same as if you were a guest in my home or a new neighbor I’m welcoming to the community. You will always receive honesty, hospitality, and straightforward guidance while I work to make your real estate experience as smooth and enjoyable as possible. Cheers!

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David Brinton

Hello there! My name is David Brinton, and I’ve proudly called Coastal Delaware home since 2003. After years of spending summers here, my husband and I decided to purchase a second home—and before long, we made the move to live in Rehoboth Beach full-time. We quickly fell in love with the coastal lifestyle and welcoming community. From forming lasting friendships to enjoying endless entertainment and exceptional dining, living in Coastal Delaware has truly been a dream come true. Today, I’m grateful to share that same lifestyle with my real estate clients. Helping others create their own life at the beach—while discovering all that these incredible communities have to offer—is incredibly rewarding. There’s nothing better than hearing how happy new residents are after making the move. With a degree in Hospitality Management and a minor in Travel and Tourism, I bring a client-first approach to real estate. I take the time to understand your goals and preferences so I can guide you toward homes and communities that align with your vision. Paired with the expert resources of the Coastal Homestead Group, our partnership delivers exceptional service, unmatched resources, and proven results. In my spare time, I enjoy watching movies, catching a football game, relaxing by the pool at our B&B, fishing, spending time at the beach, and being with friends and family.

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