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Villages History Finale, Wine Bar, and Talent Galore

Plus: Poll of the Week, Events and Live Music!

🌅 Good Morning, Villages. In today’s Village Pulse, we're spilling the (wine) on Leesburg’s coziest bistro, dishing up the last of the Villages history series, and giving a standing ovation to Villages Got Talent. Plus, polls, and a $60K home price drop? Oh yes, it’s that kind of Pulse. On this day, in 1969, Neil Armstrong became the first human to walk on the moon, declaring, "That's one small step for man, one giant leap for mankind." And they did it with less GPS tech than your golf cart!

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Let’s dive in.

— Kevin Rogers, Publisher

Poll Of The Week

Villages Pulse subscriber Sue B asked for a poll on where our readers live in The Villages, on a more geographical basis, rather than by Village (that would be a LONG poll!). I thought it would be interesting as well, so here it is!

What Area of The Villages Do You Live In?

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Last Thursday’s Poll on “do you want a whole house water filter discount was a SOLID YES, PLEASE!! 90 said YES. No promises, but I’ll do my best to get you a great deal from a local water filter company this week. I’ll let you know what happens in the near future.

Suncoast Discounted Tickets Poll was a big YES (76) as well. So which show do YOU MOST want to see?

Which Show are you MOST Interested In Seeing

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Business Briefs

Local businesses you should know

The Sipping Garden & Bistro | 605 W Magnolia St, Leesburg

Savor a charming uptown indulgence at The Sipping Garden & Bistro in Leesburg! Nestled in a cozy historic home, this intimate wine bar pours flights of reds and whites alongside gorgeous charcuterie boards, flatbreads, burrata and more. Picture yourself sipping a velvety red, sharing a beautiful meat-and-cheese spread, and letting your cares melt away. With standout service, relaxed vibes, and glowing reviews (“outstanding service,” “girls night perfection”), The Sipping Garden isn’t just a night out—it’s a mini escape. 🍷✨

Villages History

Chapter 6: Eastport Town Square – The Future Hub

The Story Looks Ahead…

In 2025, The Villages is still growing, with Eastport Town Square taking shape off Central Parkway in Sumter County, 2 miles southwest of Sawgrass Grove. Set to open in late 2025?, this 250-acre hub blends the classic town square with a regional recreation complex, hotel, shops, and dining. Designed by Schenkel Shultz, Eastport’s Welcome Center features a coffee house, lakefront porch, and 6,000 square feet of conference space overlooking Central Lake, where dragon boat races will splash. With trails, parks, and golf, Eastport aims to be a one-stop lifestyle destination. By late 2025, it’s expected to anchor new villages, pushing the population toward 150,000.

Quirky Facts & History

  • Dragon Boat Fever: Eastport’s Central Lake will host dragon boat races, a nod to Florida’s growing paddling craze. The first race is slated for fall 2025, with teams already practicing in golf cart “dry runs.”

  • Faux Factory Chic: The Welcome Center’s corridors mimic historic factories with industrial beams, but modern touches like natural light make it feel like a hip loft.

  • Infrastructure Investment: Eastport’s $35 million Welcome Center is the priciest single building in Villages history, funded by CDDs and developer cash.

  • Local Buzz: Rumors swirl that Eastport will have a “mystery attraction”—some bet on a zip line, others a virtual reality golf simulator.

Impact on Success

Eastport Town Square is poised to keep The Villages thriving as it nears build-out. Its multi-use design targets active retirees and visitors, with the hotel and recreation complex drawing tourists. The square’s 500,000 square feet of commercial space is expected to add 2,000 jobs, maintaining high occupancy rates (99% projected). New villages around Eastport will add thousands of homes by 2027, ensuring growth. Its lakefront focus and trails will enhance the outdoor lifestyle, and could spark new clubs, keeping the community engaged.

The Land Before

The Eastport site was a swampy prairie, part of Sumter County’s cattle land. In the 1800s, it was roamed by Cracker cowboys and Seminoles, with nearby Lake Panasoffkee a fishing hotspot. By the 1900s, the area had small farms growing sugar cane and peanuts, but it was remote, with dirt roads and few residents. The Turnpike’s arrival in 1957 brought minor development, but the land stayed wild, home to bobcats and egrets.

Effect of the Square

Eastport will cap The Villages’ evolution, blending tradition (town square vibes) with innovation (recreation complex). Its success will likely solidify the community’s status as a retiree mecca, drawing younger boomers and boosting tourism. The square’s infrastructure—trails, lake, and conference space—will support a denser southern population, while its modern design keeps The Villages relevant. Eastport’s opening marks a new chapter, proving the community can reinvent itself while staying true to its roots.

Final Notes

The Villages’ journey from a mail-order flop to a 33,000-acre retiree paradise is a tale of vision, infrastructure, and town square magic. Each phase—Orange Blossom Gardens, Spanish Springs, Lake Sumter, Brownwood, the Turnpike expansion, and Eastport—built on the last one, creating a community where golf carts rule, music never stops, and retirees live like they’re on eternal spring break. Quirky themes, faux histories, and resident-led clubs give it soul, while CDDs and bridges keep it humming. From Seminole lands to Cracker cowboy prairies, the area’s past adds depth to its present, making The Villages a uniquely American story.

Miss Previous Chapters? Read them here: Chapter 1, Chapter 2, Chapter 3, Chapter 4, Chapter 5

Open House

2608 Casso Ct | $390,000 | Price Reduced by $60,000!! | Open House 7/25 @ 2PM

🎉 OPEN HOUSE ALERT! 🎉
This fully furnished, expanded Cypress model in Santiago just dropped $60,000—BOND PAID and priced to move! With over 2,100 sq ft, it’s packed with perks: new roof, solar tubes, gas range, double walk-ins, outdoor speakers, and more. Tucked on a quiet cul-de-sac, it’s perfect for full-time living or snowbirding in style. 🏡 Don’t miss this sweet deal!

Villages Got Talent Coming

Get ready, Villagers—the spotlight’s on YOU! 🎤 The Villages Got Talent show by WAND Entertainment is coming, and it’s your chance to witness local legends dazzle, dance, and maybe even juggle flaming ukuleles (okay, maybe not flaming). From powerhouse vocals to jaw-dropping magic and everything in between, this is not your average talent show—it’s Villagers gone viral. 🎭✨ Don’t miss the standing ovations, the surprises, and the bragging rights. Grab your tickets now and cheer on your neighbors as they strut their stuff under the bright lights! 👏🎶 Submit your Audition HERE »

Upcoming Events

Want a Featured Event with a poster/image? Reach out.

♠️Shirley’s Senior(50+) Hold’em Tourney | Oxford Downs | Mon Jul 21 | 11:15 | Details

Boozy Bingo | Back Porch Mulberry | Mon Jul 21 | 5 PM | Details

🏌️‍♀️ Ladies Basics of Golf | Palmer Legends | Jul 22 | 9 am | Details

Jukebox Bingo V4V | Old Mill Playhouse | Tue Jul 22 | 6:30 PM | Details

🎾Advanced Pickleball (4.0+) Mixed | Oxford Downs | Tue Jul 22 | 6 - 9pm | Details

🦵Joaniefit Cardio Kickboxing | Sawgrass | Wed Jul 23 | 9 am | Details

🎾Open Play Pickleball | Oxford Downs | Wed Jul 23 | 6 - 9 pm | Details

⛳️ Joey’s Short Game Clinic | Sarasota Practice | Thu Jul 24 | 7:30 am | Details

🎤Donna & Dunning Show: Better Than Vegas | Evans Prairie | Thu Jul 24 | Details

🦞 Cousins Maine Lobster | Holy Shmokes | Thu Jul 24 | 12 - 8 PM | Details

⁉️Murder Mystery: Buying The Farm | Bistro Grand Oaks | Jul 24 | Tickets

🎭️ Villages Theater Company Presents: Tribute | Mulberry Grove Rec | Jul 25 - 28 | Details and Tix

🍷 Sip, Savor, and Song: A Wine Tasting, Food & Music Event | Lake Miona Rec | Jul 26 | Details

🍷 Wine Class | Legacy Restaurant | Sat July 26 | 1 pm | Reserve

🍽️Cooking Class | Legacy Restaurant | Tue July 29 | 12 pm or 2:30 pm 🔥 Going Fast

🎨🍷Paint & Sip | Legacy Restaurant | Thu July 31 | 12 PM | Register 🔥 Sells out Fast

Mah Jongg Tournament | Temple Shalom | Aug 6 | Details and Registration Form

If you have an event you want to announce to 6,000+ local Villagers, email us the details at [email protected]

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Weather

Monday: 93 🌡️ 78 | ⛈️ | 60% | 🌬️ W 5 mph

Tuesday: 87 🌡️ 76 | ⛈️ | 70% | 🌬️ SW 5 mph

Wednesday 88 🌡️ 76 | ⛈️ | 70% | 🌬️ Light winds

Live Music Lowdown

Monday

Spanish Springs

Justin Heet Band - rock

5 - 9 PM

Lake Sumter

Leonard Brothers Band

5 - 9 PM

Brownwood Paddock

5.0.1. - classic rock

5 - 9 PM

Sawgrass Grove

Boozy Bingo

5 - 9 PM

Edna’s On The Green

Todd Dikeman

3 - 6 PM

Red Sauce Sumter

Chris Patti

6 - 9 PM

RJ Gators Sumter

Mike & Terrie

2 - 5 PM

Holy Shmokes

Bobby Blackmon

5 - 8 PM

Tuesday

Spanish Springs

Anita Drink Band - rock

5 - 9 PM

Lake Sumter

Studio 77 - pop

5 - 9 PM

Brownwood Paddock

Zee-R Band - rock

5 - 9 PM

Sawgrass Grove

Luck of The Draw - rock

5 - 9 PM

Edna’s On The Green

Dan Flok

3 - 6 PM

Red Sauce Sumter

Mark Raisch

6 - 9 PM

RJ Gators Sumter

Coyote Joe

2 - 5 PM

Holy Shmokes

Diamond Dave Karaoke

6 - 9 PM

Wednesday

Spanish Springs

Ssnakeyez

5 - 9 PM

Lake Sumter

Trip 19 - classic rock

5 - 9 PM

Brownwood Paddock

ICON - top 40

5 - 9 PM

Sawgrass Grove

Stella Beat - top 40/latin

5 - 9 PM

Edna’s On The Green

KennaDee

3 - 6 PM

City Fire Sumter Landing

Karaoke

7 - 10 PM

Red Sauce Sumter

Billy D Williams

6 - 9 PM

RJ Gators Sumter

The Beach Billies

2 - 5 PM

Glenview Country Club

Chris Patti

5 - 8 PM

Legacy Pool Bar

Castaway

5 - 8 PM

Holy Shmokes

Gilly & The Girl

6 - 9 PM

Blondie’s Bar

John Johnson

2 - 4 PM

Boosters Bar & Grill

Andy Shreeve

4 - 6 PM

Tierra Del Sol

Thomas Watkins

3 - 5 PM

Thanks!

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P.S. Want to get your business in front of 6,000+ local Villagers? Reach out here.