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Explore Luxury Real Estate with Jonathan Dempsey in the Poconos

Our agents bring a wealth of experience to ensure your buying or selling experience is successful.
Jonathan Dempsey
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Jonathan Dempsey

As a Pocono local, avid STR investor, and STR Revenue manager of Live Free Hospitality, JD has an iron grip on the Pocono STR market.   

JD has done over $50M in volume between 2024 and 2025, helping investors enter quality equity positions through strategic development, remodeling, or timely turnkey entrance.

JD can assist you with acquisition, remodeling, interior design, and hosting through a tight network of elite vendor partners.   

JD has developed and operated many of the Poconos leading revenue producing properties.   Reach out today

In his free time, JD loves to read, travel, lead, and embrace the moment.  With a firm belief in acquiring experience with those you care about, then sharing great experiences with clients, guests, and all of this in the Live Free network.

Contact Details

Email address [email protected]
Primary phone (484) 318-0737
Address 4758 Route 447 Canadensis PA, 18325
License #RS346832
See Why Our Clients Love Us

Success Stories

Read what our clients have to say about working with us.
"I had a fantastic stay at this Airbnb! The home is exactly as described—clean, cozy, and well-maintained. It’s located in a quiet neighborhood, which makes for a peaceful and relaxing getaway. The space was perfect for unwinding, with comfortable furnishings and all the amenities I needed for a stress-free stay. The host was responsive and helpful throughout the booking process and during my stay. Check-in was seamless, and everything was clearly communicated. One of the highlights was the convenient location—close to nature, yet only a short drive from shops, restaurants, and local attractions in the Poconos. Whether you’re looking for a weekend retreat or a longer stay, I highly recommend this property. I’d definitely stay here again!"
"I had a fantastic stay at this Airbnb! The home is exactly as described—clean, cozy, and well-maintained. It’s located in a quiet neighborhood, which makes for a peaceful and relaxing getaway. The space was perfect for unwinding, with comfortable furnishings and all the amenities I needed for a stress-free stay. The host was responsive and helpful throughout the booking process and during my stay. Check-in was seamless, and everything was clearly communicated. One of the highlights was the convenient location—close to nature, yet only a short drive from shops, restaurants, and local attractions in the Poconos. Whether you’re looking for a weekend retreat or a longer stay, I highly recommend this property. I’d definitely stay here again!"
McFart
"Fabulous house! All the amenities for a great stay, and very thorough communication. Highly recommend!"
"Fabulous house! All the amenities for a great stay, and very thorough communication. Highly recommend!"
Kari L.
"Everything was great, nice cozy place, all the parking you need. I loved it, definitely will recommend it."
"Everything was great, nice cozy place, all the parking you need. I loved it, definitely will recommend it."
Fabian O.
"The cabin was easy to access and clean. Our host, Jonathan, was absolutely great and made our stay smooth and comfortable."
"The cabin was easy to access and clean. Our host, Jonathan, was absolutely great and made our stay smooth and comfortable."
Jennifer P.
"Very clean! Spacious inside and outside, beautiful setup with very comfortable bedrooms."
"Very clean! Spacious inside and outside, beautiful setup with very comfortable bedrooms."
B. Spencer
"I've stayed at a few of the properties run by this company, and they are always incredibly kind and on top of things! Taking care of their properties, clients, and customers with all-around professionalism and genuine love for what they do. A quality company to work with and stay with always."
"I've stayed at a few of the properties run by this company, and they are always incredibly kind and on top of things! Taking care of their properties, clients, and customers with all-around professionalism and genuine love for what they do. A quality company to work with and stay with always."
Alexis G.
"Great property management company located in the Poconos. I’ve worked with the team for a while, and they take great care of my home while providing a 5-star service to guests."
"Great property management company located in the Poconos. I’ve worked with the team for a while, and they take great care of my home while providing a 5-star service to guests."
Carrie H.
"If you own a short-term rental in the Pocono Mountains and are looking for a property management company to take it to the next level, look no further than Live Free Hospitality! Their expertise, professionalism, and dedication to maximizing the potential of vacation rentals are unmatched. From day one, their team has been a game-changer for my properties. They handle everything with precision and care, from stunning professional photography to dynamic marketing strategies that ensure my listings stand out on all major booking platforms. My bookings and revenue have significantly increased since partnering with them! What sets Live Free apart is their attention to the guest experience. They go above and beyond to ensure every visitor has a memorable stay, which has resulted in glowing reviews and repeat bookings for my properties. Their communication with guests is prompt, friendly, and professional, taking all the stress out of hosting. Behind the scenes, their operations are seamless. They manage cleaning, maintenance, and turnovers with military precision, ensuring my property is always in top-notch condition. I’ve received countless compliments from guests about how clean and well-maintained the space is—and that’s all thanks to Live Free Hospitality! Another standout feature is their understanding of the unique demands of the short-term rental market in the Poconos. Whether it's optimizing pricing during peak seasons or ensuring my property is equipped for the area's outdoor-loving visitors, their local expertise has been invaluable. Partnering with Live Free Hospitality has been one of the best decisions I’ve made as a property owner. They’ve turned my rentals into a thriving business while giving me the peace of mind that everything is handled professionally. I can’t recommend them enough for anyone looking to elevate their short-term rental game in the Poconos!"
"If you own a short-term rental in the Pocono Mountains and are looking for a property management company to take it to the next level, look no further than Live Free Hospitality! Their expertise, professionalism, and dedication to maximizing the potential of vacation rentals are unmatched. From day one, their team has been a game-changer for my properties. They handle everything with precision and care, from stunning professional photography to dynamic marketing strategies that ensure my listings stand out on all major booking platforms. My bookings and revenue have significantly increased since partnering with them! What sets Live Free apart is their attention to the guest experience. They go above and beyond to ensure every visitor has a memorable stay, which has resulted in glowing reviews and repeat bookings for my properties. Their communication with guests is prompt, friendly, and professional, taking all the stress out of hosting. Behind the scenes, their operations are seamless. They manage cleaning, maintenance, and turnovers with military precision, ensuring my property is always in top-notch condition. I’ve received countless compliments from guests about how clean and well-maintained the space is—and that’s all thanks to Live Free Hospitality! Another standout feature is their understanding of the unique demands of the short-term rental market in the Poconos. Whether it's optimizing pricing during peak seasons or ensuring my property is equipped for the area's outdoor-loving visitors, their local expertise has been invaluable. Partnering with Live Free Hospitality has been one of the best decisions I’ve made as a property owner. They’ve turned my rentals into a thriving business while giving me the peace of mind that everything is handled professionally. I can’t recommend them enough for anyone looking to elevate their short-term rental game in the Poconos!"
Danial K.
"The whole house itself feels comfortable and cozy the gaming room is great!"
"The whole house itself feels comfortable and cozy the gaming room is great!"
Jose C.
"Beautiful, very clean and trustworthy."
"Beautiful, very clean and trustworthy."
Leonardo G.

Browse My

Active Listings

Browse my current listings online or contact me for further information.

  • 257 Lidio Road Pending

    $1,150,000

    257 Lidio Road, Blakeslee, PA 18610

    • 7 Beds
    • 3 Baths
    • 3,000 Sq.Ft.
  • 216 Sutton Place For Sale

    $310,000

    216 Sutton Place, Pocono Summit, PA 18346

    • 2 Beds
    • 1 Bath
    • 816 Sq.Ft.
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