Oak Orchard Real Estate

Oak Orchard Real Estate

Welcome to Oak Orchard, a hidden gem nestled in the heart of the United States, where charm meets modern living. This picturesque subdivision is a perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and everyone in between.

As you stroll through the tree-lined streets of Oak Orchard, you'll be greeted by a welcoming community atmosphere that fosters connection and camaraderie. The well-maintained homes, adorned with beautiful landscaping, reflect a pride of ownership that is palpable throughout the neighborhood. With a variety of architectural styles, from cozy bungalows to spacious family homes, there is something for everyone in this delightful community.

Oak Orchard boasts an array of amenities designed to enhance your lifestyle. Residents enjoy access to scenic parks, walking trails, and playgrounds, providing ample opportunities for outdoor recreation and relaxation. The subdivision is also conveniently located near shopping centers, restaurants, and top-rated schools, ensuring that all your needs are within easy reach.

Nature enthusiasts will appreciate Oak Orchard's proximity to local lakes and rivers, perfect for fishing, boating, or simply enjoying a serene day by the water. The community also hosts regular events and gatherings, fostering a sense of belonging and making it easy to meet new friends.

Whether you're looking to settle down or invest in a vibrant community, Oak Orchard offers a unique blend of comfort, convenience, and charm. Come discover your new home in this enchanting subdivision, where every day feels like a retreat!

Newest Listings in Oak Orchard

🌊 Build Your Coastal Dream Near Indian River Bay! 🌊 CORNER LOT! Rare opportunity to own a cleared homesite just steps from the beautiful waters of the Indian River Bay in the sought-after Oak Orchard area. This ready-to-build parcel offers access to public utility tie-ins, making the path to your new home even easier. No HOA, Build the HOME of your DREAMS! Enjoy the laid-back coastal lifestyle that Oak Orchard is known for, with nearby boating, crabbing, fishing, kayaking, and waterfront dining just minutes from your doorstep. Launch your boat, drop a crab pot, cast a line, or simply enjoy spectacular sunsets over the bay. Whether you're looking to build a year-round residence, vacation retreat, or investment property, this location offers the perfect blend of water-oriented recreation and everyday convenience. Nearby shopping, restaurants, marinas, golf courses, and Delaware beaches provide endless opportunities for relaxation and adventure.

Mercer Ave, Millsboro

Listing courtesy of Elevated Real Estate Solutions. Contact: 3024222619

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

Located in the Oak Orchard Waterfront Boating Community and just minutes from prime beach locations, Bay to Beach Builders offers this NO HOA and No Land Lease property for you to build your new custom dream home. This property includes incredible views of the water with short walking distance to the boat ramp. Sewer Impact Fees have been paid representing a savings of nearly $8,000. All homes to be built with Bay to Beach Builders.

Lot 76 Oak Orchard, Millsboro

Listing courtesy of The Parker Group. Contact: 3022176692

Start Your Search

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!

Learn More

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.

Learn More