Conner Richardson

Properties of The Villages

Conner is proud to be a licensed real estate broker now serving the amazing community of The Villages, Florida — Florida’s Friendliest Hometown.

Conner has been blessed to have married the love of his life in 2017. His lovely wife Bailey joyfully serves much of the community with fresh homemade sourdough bread through The Daily Loaf 352. They are the proud parents of three wonderful children! Carter, their oldest, has just started third grade at The Villages Charter School. As she begins to build her passions she has fallen in love with volleyball and Conner and Bailey are excited to begin the “parents on the sidelines” phase. As the family journey continued, God gave Conner and Bailey boy-girl twins. 

Lincoln, the girl twin, and Watson, the boy twin are now five and entering a new season in kindergarten at The Villages Charter School. They have loved watching these two grow side by side and watching the innate differences as well as similarities shine through. 

In the fall of 2024 Conner and Bailey, after years of back and forth about the possibility of a move to Florida, finally felt truly called and chose to move the whole family across the country. It is the best decision they could have made. Thriving in the sunshine, in the community, in the school and finding a church to call home. Their three kids and Golden Mountain Doodle puppy have embraced all that Central Florida has to offer. 

Conner’s first role was in a small breakfast restaurant in Southern Maine. Conner’s strong love for the job turned out to be a deep love for the people. He thrived on getting to know his customers — their stories, their lives, and their dreams. That same connection is what drew Conner into real estate: it’s one of the most relationship driven industries in the world. It allows him to serve people in meaningful, life-changing ways.

For the past eight years, he has had the honor of helping customers through some of life’s biggest transitions — from first homes to final homes, from new beginnings to heartfelt goodbyes. He has handled everything from residential sales to investment and commercial properties, always looking for creative solutions and clear paths forward. Now, having joined The Villages, he is excited to bring energy, experience, and heart to the people of this incredible community.

Conner’s style as an agent is grounded in servant leadership. He leads by learning — asking questions, listening closely, and dreaming alongside his customers. He believes in helping people “dream in high definition,” taking the time to understand the why behind their desires. Whether he is walking a couple through their first purchase in forty years or helping a family say goodbye to a home full of memories, he is fully present — supportive, transparent, and always available.

Originally from Southern Maine, Conner carries with him the values his parents instilled early on: every problem has a solution if you’re willing to work hard enough and long enough to find it. Customers often describe him as enthusiastic, energetic, and knowledgeable, and he shows up every day with a heart full of gratitude and service. 

At the end of the day, Conner’s greatest hope is that customers walk away feeling confident, cared for, and excited for what’s next — knowing they had a true advocate and friend in their corner. Conner aims to serve his team, his customers, and his family with humility and heart, always giving glory to God in the process.

Let’s connect — I’d love to hear your story and help you take the next step toward your dream

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Cost of Living

The Lofts at Brownwood brings all new apartment-style living to The Villages — featuring one, two and three-bedroom open floorplans, with on-site recreation, golf car accessibility to Brownwood Paddock Square, entertainment, dining, shopping and fun! Through your monthly amenity fee, you’ll also have access to all of The Villages’ recreation, amenities and lifestyle our 55+ community offers.

Enjoy all The Villages lifestyle has to offer. Our surprisingly affordable monthly amenity fee of just $189.00 includes:

  • Free golf on all of our executive courses*
  • Swimming, tennis, pickleball, bocce and many more facilities are all conveniently located throughout the community
  • Over 3,000 organized activities every week through our Recreation Department
  • Fishing lakes, waterfront parks and fitness trails
  • 24 hour community watch service

*A trail fee applies if you wish to use your golf car on the trails of the executive courses. 

Amenity Fee

$189

Electric

$75

Water & Sewer

$48

Trash Collection

$11

Spectrum TV & Internet

$60

Total Per Month**

$383

**Total cost does not include monthly rent. Please understand that all prices reflected or estimated in printed material are subject to change without notice of obligation. Some items listed above will be charged based on usage.