Chesapeake Landing Land for Sale

Chesapeake Landing Land for Sale

Welcome to Chesapeake Landing, an enchanting subdivision nestled in the heart of Chestertown, Maryland, within the picturesque Kent County. This charming community offers a unique blend of serene landscapes and vibrant local culture, making it the perfect place to call home.

Chesapeake Landing is ideally situated near the tranquil waters of the Chesapeake Bay, providing residents with breathtaking views and easy access to a variety of outdoor activities. Imagine spending your weekends boating, fishing, or simply soaking in the sun on the beautiful shores. The subdivision is also conveniently located near the historic downtown Chestertown, where you can explore quaint shops, delightful eateries, and cultural events that celebrate the rich heritage of this charming town.

For those seeking land for sale, Chesapeake Landing has a selection of prime lots that offer a canvas for your dream home. Each parcel is thoughtfully designed to maximize both privacy and community spirit, allowing you to create a sanctuary that reflects your personal style. Whether you envision a cozy cottage or a grand estate, the possibilities are endless in this idyllic setting.

With a strong sense of community and a commitment to preserving the natural beauty of the area, Chesapeake Landing is more than just a place to live; it’s a lifestyle. Embrace the opportunity to build your future in this enchanting subdivision, where every day feels like a getaway. Don’t miss out on the chance to secure your piece of paradise in this beautiful corner of Maryland!

Newest Chesapeake Landing Land for Sale

Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

Kinglet Rd, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Spinnaker Rd, Chestertown

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709

Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

Sheldrake Dr, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

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Jessica Sauls | Realtor | Memory Lane Property Group

With over two decades of experience and thousands of successful home sales, I provide calm, confident guidance through every stage of the real estate journey. Since 2003, I’ve helped buyers, sellers, investors, military families, and those navigating major life transitions make smart, well informed decisions. I do this with clarity, integrity, and strong advocacy. Real estate is more than a transaction, it’s deeply personal. I’m known for creating a steady, reassuring experience during what can often feel overwhelming. My clients value my ability to listen closely, communicate clearly, and protect their interests at every step. Whether negotiating complex terms, preparing a home for market, or navigating unexpected challenges, I lead with professionalism, transparency, and care. As a top performing Realtor in Maryland and Pennsylvania, I combine deep market expertise with a strategic, hands on approach. I help sellers maximize value through thoughtful preparation, including repairs and upgrades with payment deferred until closing. For buyers, I provide honest insight, strong negotiation, and a no-pressure approach. I want all of my Clients to move forward with confidence. Having successfully navigated multiple market cycles, I understand how to adapt strategies in changing conditions while keeping my clients’ goals front and center. Beyond real estate, I am deeply committed to my community, supporting scholarships, housing initiatives, and local education. That commitment to service carries into my work, showing up fully, advocating fiercely, and always doing what’s right for my Clients. If you’re looking for an experienced, steady professional who will treat your goals with care and deliver a strong, strategic outcome, I would be honored to work with you. It's my Mission to provide strategic, ethical, and compassionate real estate guidance that empowers people to build stability, wealth, and a life they love. We create calm, clear, and trustworthy experiences, and we strengthen our community through service, connection, and integrity. I believe in building futures, relationships, and legacies that last.

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Brian Sauls | Realtor | Memory Lane Property Group

Brian brings a thoughtful, detail-oriented approach to every real estate transaction. He helps clients understand the true condition and quality of a home beyond surface details, offering valuable insight during showings and throughout the decision-making process. Known for his calm demeanor, reliability, and strong attention to detail, Brian ensures clients feel comfortable, informed, and well supported from start to finish. He answers questions in real time, offers practical perspective, and helps buyers assess homes with confidence and clarity. Brian’s approach is grounded, professional, and service-oriented. His ability to provide meaningful guidance while keeping the process smooth and stress-free makes him a trusted advocate for his clients every step of the way.

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Christina Jones | Client Care | Memory Lane Property Group

Christina is the heart of our client experience and serves as our Director of Client Care. From the moment a client enters our world to well beyond the closing table, Christina ensures every detail is handled with care, clarity, and consistency. With a calm, organized, and compassionate approach, Christina manages communication, timelines, and behind-the-scenes coordination so our clients feel supported and informed at every step. She is often the friendly voice checking in, the steady hand keeping everything on track, and the person making sure nothing slips through the cracks. Christina is deeply committed to creating a smooth, low-stress experience for buyers and sellers alike. She understands that real estate transactions often come during significant life moments, and she brings patience, empathy, and professionalism to each interaction. Her focus on service, follow-through, and genuine care allows our team to deliver a thoughtful, high-level experience — one where clients feel heard, respected, and confident throughout the process.

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Payson Clausen Realtor

Payson Clausen | Realtor | Memory Lane Property Group

Payson Clausen brings together years of experience in real estate, media production, and marketing to support our team and elevate the client experience. With a strong background in both the real estate industry and creative media, Payson plays a key role in how properties, brands, and stories are presented. His expertise in video production, marketing strategy, and digital content helps ensure our listings and messaging are clear, compelling, and thoughtfully executed. Beyond his professional skill set, Payson is deeply committed to serving his community. He regularly volunteers his time working with local students and is actively involved in raising funds for SkillsUSA, supporting career and technical education programs that prepare young people for future success. Payson’s blend of industry knowledge, creative talent, and community involvement reflects our team’s values — using our work not just to serve clients, but to make a meaningful impact beyond the transaction. (function() { var rg = document.createElement('script'); rg.type = 'text/javascript'; rg.async = true; rg.src = 'https://widgets.realgeeks.com/static/js/search_widget_new.js?v=3'; var s = document.getElementsByTagName('script')[0]; s.parentNode.insertBefore(rg, s); })();

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