Jon Dempsey Hile

Port Charlotte FL

PARADISE EXCLUSIVE INC

65 Closed Sales

$23.3M Total Value

$80K - $1.9M Price Range

$358.1K Average Price

Prior five years

About Jon

At Partners in Paradise, we are dedicated to helping clients successfully navigate one of life’s biggest transitions—buying or selling a home. With over eight years of experience in the local real estate market, our team is committed to delivering exceptional service before, during, and long after each transaction. Our business is built on trust, results, and referrals from satisfied clients who value our white glove hands-on approach and proven results.

As proud residents of Englewood, Florida, we embrace the coastal lifestyle and take great pride in helping others find their place in paradise.

Tawnya:
I relocated to Florida from Massachusetts with my family in 1985 and have called Charlotte County home ever since. I enjoy spending time outdoors—kayaking, fishing, and collecting shells and shark teeth. Real estate is a family tradition, with both my mother and brother also in the industry. Helping clients find their dream home is my true passion.

Jonathan:
Originally from Louisville, Kentucky, I come from a family rooted in public service and leadership. Before transitioning to real estate, I had a rewarding career in the fire service, including time spent assisting in New York following the 9/11 attacks. I’ve also been active in athletics, including semi-pro football and rugby. Above all, I’m a proud father of two amazing children, and I bring the same dedication and drive to my clients as I do to my family.

Home Types: House, Manufactured, Lot/Land, Townhouse, Condo

Years of Experience: 3

Transaction History

1 Year
2 Year
5 Year

Seller Deals

Total Deals

Total Value

$6,296,900

Average Sale Price

$299,852

Price Range

$25K - $725K

Buyer Deals

Total Deals

Total Value

$2,451,700

Average Sale Price

$306,463

Price Range

$160K - $750K

1 Year View by Quarter

Seller Deals

Total Deals

Total Value

$9,049,400

Average Sale Price

$282,794

Price Range

$20K - $725K

Buyer Deals

Total Deals

Total Value

$5,147,690

Average Sale Price

$367,692

Price Range

$160K - $965K

2 Year View by Quarter

Seller Deals

Total Deals

Total Value

$13,017,400

Average Sale Price

$295,850

Price Range

$14K - $725K

Buyer Deals

Total Deals

Total Value

$10,259,360

Average Sale Price

$488,541

Price Range

$160K - $1.9M

Neighborhoods Jon is Experienced In

Jon's Open Houses

$534,900 Open Sun 12PM - 2PM
- 3 Beds
- 3 Baths
- 2,294 Sq Ft
10350 Coral Landings Ln

Unit 61

Placida, FL
**MOTIVATED SELLER!!** Coastal Luxury Meets Blissful Waterfront Serenity and Privacy. Experience the best of coastal living in this 2019-built WATERFRONT luxury townhome offering 2,294 sq. ft. of refined living space (TURNKEY FURNISHED) with unmatched, undisturbed panoramic water views. From your private balcony and the serene master suite, take in enchanting views of dolphins, manatees and

Jon Dempsey Hile PARADISE EXCLUSIVE INC

Jon's Active Listings

$569,900
- 3 Beds
- 3 Baths
- 2,449 Sq Ft
8553 Saint Kitts Cir

Englewood, FL
Live Your Best Florida Life at Island Lakes at Coco Bay! **OPTION to PURCHASE TURNKEY FURNISHED for $15K outside of contract.** Welcome to your dream home in the gated, resort-style community of Island Lakes at Coco Bay where coastal relaxation meets everyday luxury. This immaculately built 2024 Summerville II is Lennar's flagship model for this community. The beautifully designed and built 3

Jon Dempsey Hile PARADISE EXCLUSIVE INC

$550,000
- 3 Beds
- 2 Baths
- 1,354 Sq Ft
352 Oak St

Englewood, FL
**Paradise Found on Lemon Bay!** All life begins in and around the water and this home is where your life can be lived to the fullest. With 100 feet of canal frontage leading directly to the crystal-blue intracoastal waters of Lemon Bay, you’re just a 20-minute boat ride to the Gulf and only half a mile from Royal Palm Marina, truly a boater’s paradise. Start your mornings fishing right off your

Jon Dempsey Hile PARADISE EXCLUSIVE INC

$399,000
- 3 Beds
- 2 Baths
- 2,309 Sq Ft
425 Cypress Forest Dr

Englewood, FL
Welcome to Park Forest – Englewood’s Premier 55+ Gated Community! Step into this impeccably updated and move-in ready home offering an impressive 2,309 square feet of living space with breathtaking 180 lake views from the moment you walk through the door. Designed for comfort, style, and easy living, this residence perfectly blends modern updates with tranquil Florida charm. Inside, you’ll find

Jon Dempsey Hile PARADISE EXCLUSIVE INC

$245,000
- 2 Beds
- 2 Baths
- 1,240 Sq Ft
1311 Washington Dr

Englewood, FL
Location, Location, LOCATION! Brimming with coastal charm, this delightful home sits in a quiet neighborhood just 7 minutes from beautiful Englewood Beach! This neighborhood is included in the exclusive Englewood Gardens Beach Club, offering deeded private beach access, a clubhouse, restrooms, picnic area, plus bay access with a fishing dock and kayak launch—all for a minimal annual fee.

Jon Dempsey Hile PARADISE EXCLUSIVE INC

$219,900
- 2 Beds
- 2 Baths
- 1,263 Sq Ft
749 Portwine Ct

Englewood, FL
Paradise Found in Vibrant 55+ Gated Community! Welcome home to "The Coastal Retreat!" If you’ve been dreaming of life in a lively, amenity-rich 55+ gated community—just minutes from the pristine beaches of Southwest Florida—yet crave the peace and privacy of a quiet cul-de-sac, your search ends here. Welcome home to your own slice of paradise! This resident-owned, land-included (no lot rent!)

Jon Dempsey Hile PARADISE EXCLUSIVE INC

Co-Listing Agent

$412,000
- 3 Beds
- 2 Baths
- 1,957 Sq Ft
7095 Beardsley St

Englewood, FL
A LUXURIOUS COASTAL RETREAT — POOL READY & EXQUISITELY RENOVATED! Every inch of this meticulously reimagined 1,957 sq. ft. residence radiates sophistication and refined coastal elegance. Built in 1990 and completely remodeled with premium finishes, this captivating home offers a dedicated pool bath already in place and direct patio access from both the primary suite and one of the guest bedrooms

Jon Dempsey Hile PARADISE EXCLUSIVE INC

Co-Listing Agent

$399,000
- 3 Beds
- 2 Baths
- 1,974 Sq Ft
5 Barbados Rd

Unit 31

Englewood, FL
Discover the perfect blend of luxury, leisure, and location in this rare opportunity within the highly sought-after BOCA ROYALE Golf & Country Club! Tucked away on a quiet cul-de-sac, this exceptional villa resides in the exclusive enclave known as Englewood Golf Villas—a charming community of only 45 residences, complete with its very own private pool. Step inside and be captivated by nearly

Jon Dempsey Hile PARADISE EXCLUSIVE INC

Other Experience

First Time Home Buyers, Investments, Luxury Homes, Military Families, New Construction, Senior Communities

Agent License: Florida #3535631

Jon Dempsey Hile

(941) 231-6016

Jon Dempsey Hile

About Jon

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Neighborhoods Jon is Experienced In

Jon's Listings and Deals

Jon's Open Houses

Jon's Active Listings

Other Experience