With over 200 years of combined real estate sales experience, Waypoint Properties has a truly dynamic sales and property management staff. We pride ourselves in the fact that our brokers and agents are well trained, well educated, experts in their fields; constantly continuing their education and increasing their knowledge base.
With a wide range of interests and expertise, we have agents with backgrounds in appraisals, investment and financial planning, commercial real estate, property management, land management, development, construction, design, marketing, and business management. We are confident that such a wide variety of skill sets shared between our agents and staff will allow us to serve nearly everyone with virtually any real estate need. Contact one of us today to see the difference Waypoint Properties can provide.
As one of Waypoint Properties founding brokers, Josh takes great pride in creating an atmosphere where buyers and sellers can feel comfortable knowing they are being helped by some of the most knowledgeable and capable brokers and agents in all of North Florida. But facts and figures can only take you so far, what really sets Josh apart, and his company, is the dedication to providing an unparalleled level of professional service without losing that personal touch of a friend. Josh’s motto is “It’s not just business, it’s personal”, and that rings true throughout the company. He’s different because he genuinely cares about doing quality work and creating long lasting relationships with customers who can count on him to provide excellent service from start to finish with a work ethic that shows his commitment and dedication to customers. He understands that buying and selling homes and land can often be a pressure filled time in his customers lives and works extremely hard to be that person that customers can turn to and count on for sound advice and accurate information. To be that friend in their corner, who understands what they are going through and is there to help because he truly cares about them.
Elaine Gary worked 24 years at The Florida Bar lawyers association where she met her husband Don. She has 3 grown children, and five grandchildren. While raising her children in Tallahassee, Elaine and her family fell in love with Wakulla County once they discovered fishing and scalloping in the Gulf of Mexico, and gathering blue crabs at Mashes Sands. Don and Elaine moved to Wakulla County in the mid 90’s due to their love of the water. Elaine got her real estate license in 2004 when real estate was booming and her broker’s license in 2006 as the market was starting to fall.
Elaine was managing broker for nine plus years in a fellow real estate company when the bottom fell out of the market and was not only able to thrive, but to build the company and its property management division while exceeding her sales goals. In September of 2015 Elaine partnered with Josh Brown in opening Waypoint Properties. Elaine and Josh knew with their high level of ethics and sales experience they would make a great team. Elaine looks forward to working with agents, customers and landlords in “Finding Their Way Home” by using Waypoint Properties for all their real estate needs.
Casey joined Waypoint in 2018 with over 10 years of a customer service background. As Property Manager, Casey manages rentals throughout Wakulla and Leon County. In 2022 she facilitated the expansion of Waypoint East adding Jefferson County to our rental portfolio. Casey stays on top of market trends, available rentals, and is a huge asset to owners looking to boost their ROI. This position requires attention 24/7 , but when she is not working, she enjoys time with her beautiful daughters and family.
Cassie Johnson has been an active member of Wakulla County for 11 years now, and is so excited to be turning that community focus toward real estate. Born in Jacksonville, raised in Tallahassee, Cassie relocated to Wakulla in 2011 for her daughter to attend the excellent schools they have to offer. Her daughter graduated from Wakulla High in 2020 and now is attending TCC to pursue Nursing.
With a passion for service she has over 23 years customer service and business experience from a career in Property Management. Cassie carries the values of hard work, integrity, and outstanding client service into everything she does. When Cassie isn’t making homeownership dreams come true for her clients, she enjoys spending time traveling and the outdoors.
Sara Robinson (A.K.A Deals on Heels)
As a seasoned realtor with over 15 years of experience, I have had the pleasure of helping countless individuals and families find their dream homes. Throughout my career, I have developed a deep passion for the real estate industry and take great pride in providing exceptional service to my clients.
My approach to real estate is rooted in honesty, integrity, and a commitment to always putting my clients’ needs first. Whether you are a first-time homebuyer or a seasoned investor, I have the knowledge and expertise to guide you through every step of the buying or selling process.
Over the years, I have built a reputation for being a trusted advisor and skilled negotiator. I understand that buying or selling a home can be a stressful and emotional experience, which is why I always strive to make the process as smooth and stress-free as possible.
I am the proud wife of a Veteran Marine pilot and the mother of two beautiful children. I truly love my work, but my real passion is spending time with my family and friends. I am a 5th generation Wakulla County resident. This is my home and I take pride in growing up here. If you are looking for a realtor who truly cares about your needs and will go above and beyond to help you achieve your goals, look no further. I am here to help and would be honored to be a part of your real estate journey.
Jess was born and raised in Texas and moved to Florida to enjoy life more in the great outdoors.
She graduated from the University of North Texas with a Bachelor’s of Science in Criminal Justice.
Jess loves animals and people. She worked as a veterinary technician through college and in her professional life, she worked as the Director of Operations at the Texas Coalition for Animal Protection, a non-profit organization.
She enjoys nature, adventure, traveling, and the comradery of good people. Jess has a passion for dirt bike riding, scuba diving, and backpacking.
With her diverse experience, Jess is your go-to lady! She works quickly, efficiently, and thinks outside of the box. Jess would love to help you anywhere from finding your first home to your forever, dream home!
A local man with a heart for the community. Born and raised in Wakulla, Caleb grew up in church and the outdoors. Building long lasting relationships founded on trust and integrity is his trademark. He serves the youth as a local high school baseball coach and loves volunteering with church and outdoor events. Caleb’s commitment to people and investment in others is what makes him different.
For the last five years, Caleb has been a land manager and professional hunting guide in six different states. Constant communication and making a plan for success is a skill Caleb applies in every situation. With experience in land and the outdoors, he will surely get outside and get his boots dirty to find your future property.
From buying your first home, to investing for the future, Caleb realizes the pressure and strives to simplify the stress, and bring enjoyment to the process. Come and feel the difference and give Caleb a call.
Office – (850) 997-2500
Waypoint Properties – Monticello
340 S. Jefferson St.
Monticello, FL 32344
I graduated from Florida State University in 2003 with a degree in Sports Administration. In 2006, I acquired my real estate license after realizing a passion for the real estate industry that rivaled my passion for all things sports. I’m a native of the Tallahassee/Crawfordville area for the past 30 years which provides me with added knowledge of the real estate market areas and market conditions from Northern Leon County all the way to the Forgotten Coast. I look forward to helping clients in any capacity. Whether it’s buying, selling, relocating, upgrading or downsizing; I will work tirelessly to get the job done.
I have spent my entire life learning about people and enjoying the experience of helping others achieve their goals. The past 30 years have all been spent in the county that I love, serving the citizens of Wakulla in one of the best school systems in the state of Florida and as a Realtor at Waypoint. As a fourth generation Wakulla County resident and a 1980 graduate of Wakulla High School, I have had the opportunity to learn a great deal about our county and I am looking forward to sharing that lifetime of knowledge with folks who need real estate services.
I graduated from Florida State University with degrees in Criminology and Counseling and from Stetson University with a Specialist Degree in Educational Leadership. I have represented buyers and sellers in Wakulla County and every surrounding county for the last 5 years. I am eager to help you!
Whether you love the beach, hunting, fishing , or just plain old serenity, together we will find the property of your dreams. As your agent, I provide you with a smooth process – whether it be marketing your home, buying your dream home, or investing in a property. My goal is your full satisfaction; with over 30 years experience in sales and customer service and 20 years of combined real estate licensure, I know how to adapt to each individual’s wants and needs. As a long time Florida Panhandle resident, my clients trust me to provide quality properties and sound advice in Franklin, Gadsen, Wakulla, or Leon County. Looking forward to working with you and yours.
I have spent my whole life right here in the panhandle of Florida! My family moved from Tallahassee to Crawfordville 25 years ago and now I am raising my very own family in the same neck of the woods!
I grew up in the construction industry from tying rebar at 8 years old to working in that same family owned business. I have spent the last 9 years working for the State of Florida and helping Florida business owners. With both being brought up in a family owned business and working with Florida business owners, I believe in honest quality work and enjoy creating those life long relationships!
I am a mom to two very outgoing little girls and a fur mom to our English Springer! My husband is an Army Veteran and we enjoy spending time outdoors and visiting the beautiful beaches along our coast. I am a collector of passed down family recipes and I also enjoy creating my own!
I’m a lifelong resident of Wakulla County and have a passion for the lifestyle that comes with it. I have more than 10 years of experience in real estate sales, property management, and land surveying in the local area. My experience makes me familiar with the areas that will provide the type of living that you are looking for. From neighborhoods in North East Tallahassee to country living in Wakulla and the surrounding areas, if you want it I can find it. Give me a call to see how I can help you move out of your current home into your dream home!
As natives of Wakulla County, my husband and I chose to plant roots here because of what this small community means to us. We raise our children in this beautiful place we call home. We love being a part of this community and all it has to offer, it’s truly where our hearts are.
I am a realtor with Waypoint Properties, I’ve been a licensed Realtor for 7 years now and I’m the Head Coach of the Wakulla Christian Volleyball Team. My husband has a vital part in our community as a local lineman. He also plays an active role in helping coach our girls softball team at the Wakulla County Rec Park. We have 3 beautiful girls and another baby on the way!
We believe in community & family! That’s one of the many reasons I love being in real estate, it allows me to help families of all different sizes find the perfect place for them where they too can plant roots and call this place their home.
I’d love the opportunity to help you find just what you’re looking for. From my heart, to your new home
As a Florida native and Wakulla county resident for over 20 years, you can trust Jessica’s local knowledge and network to guide you in the right direction whether you are buying or selling!
Jessica is a Florida State University Alumni with a Bachelor of Science in Sport Management. She is also a personal trainer at Body Tek 24 Hour fitness in Crawfordville.
When she isn’t helping her real estate clients, Jessica and her husband, Chris, enjoy fishing, mountain biking, traveling, and spending time with her family and friends. Jessica is an animal lover and has 3 dogs of her own.
Whether you are looking to move to the coast, stay inland in a neighborhood, or find a large piece of property to build your home, Jessica is here to help your make your real estate dreams come true!
Being a 5th Generation Wakulla County Resident, I have a deep appreciation for small town living. After graduating from Wakulla High School in 2007, I moved away to Lakeland, FL, to attend Southeastern University. My college experience offered me the opportunity to tour the east coast of the United States with a band I had to audition for and represent the University at various Youth Camps. The opportunity to tour was one of the most incredible experiences of my life; however, it left me missing my small town and I became homesick. I returned back to Wakulla County in 2009 and decided to get into Real Estate as an office assistant. It wasn’t until 2013 that I decided to get into the Real Estate Industry full time, as an agent and get my license. Having 11 years’ experience in Real Estate and Office Management, I can truly say I enjoy what I do!
I am a mom to a spunky little girl and love spending my time with family, out doors enjoying the rivers, beaches and trails Wakulla has to offer! I feel abundantly blessed to call Wakulla County my home!
I have been providing real estate services for over 18 years, starting my career in SW Florida where I grew up, my family had moved to the Crawfordville area in 2010, and continued my career. I am proud to work at Waypoint Properties, an office that has “Your best interest at heart”. I have a strong foundation of providing professional real estate services, working directly with customers to make sure they are aware of every step with the transaction. I strive to keep my education up to date, professional, and provide the best agent & service to my clients. I have earned my Brokers license, GRI (Graduate Realtor Institute) RENE, SRS & C2EX. I welcome you to see what a difference it is when you are working with a “results driven” Realtor. When you work with me, you’re not just a client, you’re family.
What you can expect from me is loyalty, hard work, honesty, diligence, and patience. Having a qualified and dependable agent makes all the difference, your real estate transaction is one of the most important decisions you will make in your lifetime! I pay attention to every detail; will always keep fully informed of every step of the process and provide open communication. Ultimately, you need to find the right agent you feel comfortable and trust, I hope I will earn your trust and your referrals!
Nicki Beam began her journey into real estate by helping her husband run his local construction company, Erick Beam Construction, which has been building homes in Wakulla and the surrounding counties since 2007. This time spent in the construction industry sparked her interest in real estate, and led her to join the Waypoint Properties team as a Realtor in 2019. In addition to her work in real estate and construction, she also works as a dental hygienist in a local dentist office. When she is not working, she enjoys spending time outdoors with her two children and her husband.
Amy grew up in Tallahassee. She enjoys spending her weekends at Alligator Point. She grew up in and around the water and has loved it ever since. Amy’s family has been doing real estate since the 70’s so it was only fitting that she got her real estate license. She has had her license since 2013. Amy has been married to her husband Mike for 18 years and they have two sons Michael and Mason. Amy loves the beach, camping and spending time with family.
For the last 20 years, Jackie worked in the medical field, while her husband has worked in the construction industry since the 1980s. After leaving the medical field, she decided to join her husband in the home business by becoming a realtor. Jackie was born and raised in Taylor County, but she and her family have lived in Wakulla County for over twenty-five years. She loves the small town feeling and all it has to offer.
Jackie enjoys spending her time with her husband of 35 years, her two daughters and her two grandchildren. She also enjoys playing golf, working in her yard and scalloping. She looks forward to working with people to help them find their dream home in our great community.
I am fourth generation Floridian who has lived in North Florida my entire life. As a young child I spent many hours with my Dad hunting in the pine woodlands and fishing in the lakes and rivers of Leon, Franklin and Wakulla Counties. Through this time spent with my Dad I developed a love and respect for this area and the natural beauty it holds. These experiences as a child have carried over to my favorite pastimes, spending time on our beaches, camping, and fishing. I graduated from Leon High School and attended Gordon Military College and Tallahassee Community College. I served twenty three years in the Florida Army National Guard retiring with the rank of Sergeant First Class. I started in real estate sale in the early 70s. My career spans the entire area of sales, rental, leasing, and development. By joining Waypoint Properties I will be using my many years of experience to assist the people of this area with all their real estate needs.
In 1969 I married the love of my life, Carolyn Cissne Faulk. We are the proud parents of two daughters Bonnie and Amy. Some of their fondest memories are of the time they spent at our home on Alligator Point and the lazy summer days playing on the beach. We have five grandchildren. We enjoy spending time with them camping and visiting the many historic sites in Florida. By doing this we hope to instill an appreciation for the beauty and history our state has to offer.
By combining my years of experience with the full real estate services of Waypoint Properties, I look forward to serving your real estate needs
Levi has been in Tallahassee for over 16 years where he met his wife Kate in college. Levi went to FSU where he received a bachelor’s degree in Environmental Science and a Master of Business Administration. His wife Kate works at the Tallahassee Memorial Hospital Cancer Center as a radiation therapist. Levi and Kate are expecting a baby girl this September and are excited for the new adventure. Levi has met and befriended many Tallahassee, Crawfordville, and Monticello natives playing slow-pitch softball over the last 10 years. When they aren’t at the softball fields, Levi and Kate enjoy working out at Modern Fitness Tallahassee and traveling to see their families in Ocala, Florida, North Carolina, and Nebraska.
Levi also helped start a small real estate investment group in Tallahassee and hopes to grow the group to help investors network and be successful in their real estate endeavors. He is excited to be a part of Waypoint Properties and hopes to become an asset in the Tallahassee area helping buyers and sellers meet their real estate goals!
Bridget Davis grew up locally in Perry, FL. She moved to Monticello and became very active in the community. She works at Rev Cafe part-time during the week, engaging with all of her wonderful customers. Getting
to know everyone on a personal level is something she enjoys, which sparked an interest in real estate. Family means everything in her life. She has two beautiful baby boys who make her world go around. In her personal time, she loves traveling, spending time with family and going boating. With a passion for helping others find their forever home,
Bridget is determined to help you with all your real estate needs.
Ken Nichols was born in Quincy, raised in Tallahassee, and now resides in Monticello. He attended Rickards High School where he played football for four years. After graduating in 1980 he then served in the U.S. Air Force at the Air Force Flight Test Center, Edwards AFB, California. Following his time in the military, Ken met and married his beautiful wife Donna and they have raised two children, Josh and Mikayla. Ken and Donna are proud grandparents of five grandchildren.
Ken coached football at the middle and high school levels in Tallahassee serving at Chiles High School (2001), Cobb Middle School (2002-2013), and North Florida Christian School where he served as head Middle School Coach for four years (2017-2020). Ken has enjoyed coaching young athletes for over 30 years in Tallahassee all together including Church leagues and Parks and recreation leagues.
Ken spent almost forty years in customer service in the office machine industry and has learned how to listen and care about the needs of others through his experiences. He decided to enter the real estate field because he feels like the buying and selling of a home is one of the biggest decisions someone will make in their lifetime and would like to help people through this process knowing someone is there for them helping guide them through every step of the way. Ken strives to be the kind of person who is trustworthy, honest, and knowledgeable. He believes passionately that in this life we are either leading others toward Christ or away from him by the example we set for others. He seeks to lead towards!
Born in Georgia, but raised in Franklin and Wakulla County, Jack’s roots run deep in the south. He currently studies at Florida State University, striving to receive a degree in the business of finance. A driven, determined and hard-working individual, Jack always finds a solution to problems, answers questions, and takes the time to get the job done right. Jack is happy to serve in his county helping current and new residents settle down in a place he calls home. He grew up loving to golf, fish, and hunt. Luckily, Wakulla County has seemingly endless places to enjoy these hobbies. It has everything a sportsman like Jack dreams of including multiple rivers, beaches, and is surrounded by thousands of acres of National Forest. Jack is excited to share all of this area’s natural beauty as few places have as much to offer. Jack looks forward to his career in real estate and to being given the opportunity to help buyers and sellers find their way home…..
Growing up on the water and in the woods, as well as managing a 50-year-old family owned bait and tackle store opens a lot of doors when it comes to real estate. It allowed Jacob to be able to meet many members of the community, learn the strengths and weaknesses of the local market and establish ties with local business owners. His knowledge and contacts will help people seamlessly navigate the housing market.
He also has a heart for service. He chose a career path as a firefighter and EMT to help fulfill his desire to serve others. Finding a family their perfect home as stress-free as possible is one more way to service others! You can find Jacob with his family, hunting, fishing, or playing a round of cornhole. His reputation as a go-getter and trusted member of this community precedes itself. Whether it’s buying land to build your dream house on or buying a beachfront property to relax at, he realizes the importance of any transaction and will strive to make it as stress free as possible. Give him a call to help make your dreams reality.
As someone who has grown up and lived in Franklin and Gulf counties her whole life, Nailah knows just how special this piece of Florida actually is. Ever since she was a child, Nailah has loved the beach, being outdoors and spending time with family and friends. Growing up on the sandy white beaches of the Forgotten Coast has given her a deep connection and appreciation for this place that she gets to call home. More than anything, she wishes to see this area prosper and thrive through real estate. With years of experience in the hospitality industry prior to her real estate profession, she knows that her number one goal should be the satisfaction of her customers. One of Nailah’s greatest pleasures is helping people out, no matter what it takes. Whatever the task may be, she is on the job to get it done in the best way possible. Putting your needs above all, she will help you find your own slice of a paradise- a place she gets to call home and welcomes you to join her in enjoying.
As a born and raised Wakulla County resident, Bethany has served the citizens of this county as a local business owner over the last 18 years at Dazzles Hair Studio. The relationships and connections she has made along with the knowledge she has gained will allow her the opportunity to help you fulfill all of your real estate needs.
She has been married to her wonderful husband Adam Lassiter for 16 years and they have two very active children that keep them involved in lots of activities the county has to offer. Adam owns Dorado Design and Construction building houses and also has sold real estate for the last 17 years.
When she is not working, you can find her at the beautiful beaches in the Destin/Miramar area, so whether you are looking for a vacation home in paradise or a small town home in the country, she would love the opportunity to help!
Wynter Harvey was born and raised right here in Wakulla County. A graduate from Wakulla High School in 2018, she went on to attain a Bachelors of Science Degree in Criminal Justice at Florida State University. After graduating from FSU, she then graduated from Pat Thomas Law Enforcement Academy, and began to serve her community at Tallahassee Police Department.
As most Florida natives, Wynter loves being outdoors. She enjoys kayaking on the Wakulla River, visiting our beautiful local beaches, and fishing with her dad in her free time.
Wynter is a strong believer in faith, community, and family. She is so excited to make new, lasting connections here and continue serving her community. Wynter would love to help you find your forever home!
Accessible & Responsive
Dedicated & Strong Work Ethic
Trustworthy & Passionate
Professional & Tech Savvy
“Your needs are my #1 priority. I am easily accessible and here to listen, guide, educate and help you find your special home that is a perfect fit for your lifestyle!” Connie brings strong credentials with over 30 + years of experience as Vice President of a Public Relations firm, business owner, event planning expert, teacher, and juvenile justice program director professional. These specialties along with a strong background in sales management make her a tremendous asset as an agent. She has a superb understanding of people and a keen insight into the real estate market. Living on the coast for over 30 years, Connie is well aware of the many amenities the coastal life affords. That’s why she moved here, that’s why she stayed. Contact Connie to help you find your perfect home or investment property, be it a fisherman’s cottage by the sea, a farm with acreage and room for livestock, a condo in town, or a starter home for first time buyers. Call her now to begin (or continue) the journey of home ownership or real estate investment.
I moved to the Wakulla County area in 1996 and fell in love with the small hometown feel of Crawfordville. Wakulla County has wide open spaces to enjoy just about any type of outdoor activity and sports from fishing in the Gulf or local rivers to hunting in our national forests as well as driving down our country roads just enjoying our abundant wildlife and our wonderful beaches.
After spending over 17 years in the legal field as a Paralegal, I have found another niche in a fantastic career in the ever changing real estate industry. I am diligent and hardworking, my approach with real estate Customers is somewhat low-keyed. I spend time with each Customer, be it a Seller or a Buyer, to get of feel of what their real estate needs are. I specialize in Crawfordville and surrounding areas in Wakulla County. I have been in the real estate business since 2005 and continue to update my education to be the best possible Realtor and now a Broker Associate, I can be to my Customers. I know the area and market thoroughly and I have the experience and the advanced training in the field of real estate and will continue to advance my real estate training.