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Charming Small Towns Near The Villages Florida

by Ryan Erisman | Updated: August 7, 2025

The Villages is great, but as much as it's growing it no longer has that small-town feel that attracted so many early residents.

But if you like the location, here are some places nearby to consider.

These towns offer their own unique charms and amenities, making them potential retirement destinations near The Villages.

Tavares

Located on the eastern shore of Lake Dora, Tavares is a waterfront town known as the “Seaplane City.” It offers a relaxed lifestyle with opportunities for boating, fishing, and lakeside activities. Tavares also has a historic downtown district and hosts various events and festivals.

Tavares is home to a new 55+ community called Cresswind at Lake Harris.

Cresswind at Lake Harris offers a lakefront location just minutes from downtown Tavares and Mount Dora in Central Florida.

In addition to the community dock for boating on Lake Harris, a future lakefront, resident-only clubhouse will serve as the central hub, featuring the Cresswind SmartFIT Training Center, resort-style pool, pickleball courts, art studio, event spaces, and indoor/outdoor gathering spots to unwind and connect with neighbors.

Cresswind at Lake Harris will feature a new collection of floorplans designed specifically for active adults.

Get More Information About Cresswind at Lake Harris

Lady Lake

Lady Lake is a small town known really as the birthplace of the world's biggest retirement community. It offers a range of amenities and services, including shopping centers, golf courses, and medical facilities.

It is also home to a brand-new (opened in the Spring of 2025) 55+ community called Cresswind at Hammock Oaks.

Cresswind at Hammock Oaks is a 55+ community in Lady Lake, located less than 3 miles from The Villages.

The planned resident-only clubhouse will feature a SmartFIT Training Center with EGYM technology, resort pool, pickleball courts, art studio, and various gathering spaces. The community offers new floorplans specifically designed for active adults, with customization options available through an on-site Design Studio.

Get More Information About Cresswind at Hammock Oaks

Inverness

If you travel west on FL-44 from The Villages, the first real town you run into is Inverness. Inverness is a charming small town nestled alongside the Lakes Tsala Apopka chain, offering residents a peaceful, affordable lifestyle with easy access to outdoor activities like fishing, boating, and hiking the Withlacoochee State Trail. The historic downtown area, with its well-preserved courthouse and local shops, gives the city character while maintaining a friendly, close-knit community atmosphere that makes it particularly appealing for retirees and families looking to escape bigger city life.

Just past Inverness is where you'll find Citrus Hills:

Located less than an hour from The Villages, the Villages of Citrus Hills is a Florida Retirement Community with single-family homes and maintenance-free villas that have been built with today’s demanding baby-boomer in mind. But what makes the promise of Florida Retirement in the Villages of Citrus Hills truly come together for today’s new breed of active adult retiree is its extraordinary collection of world-class community country club amenities and extensive social activities. Villages of Citrus Hills offers a variety of home styles and neighborhoods to choose from.

Get the Citrus Hills Brochure

Summerfield

Summerfield is a small town located just north of The Villages, making it a convenient option for retirees who want to be close to the amenities and services offered by The Villages but prefer a quieter and more suburban lifestyle.

One of the notable features of Summerfield is its proximity to Lake Weir, which offers opportunities for boating, fishing, and other water-related activities. The area is known for its beautiful natural scenery and outdoor recreational opportunities.

Keep heading north and you run into Ocala and On Top of the World:

On Top of the World residents can enjoy any schedule that suits their tastes – from activity-packed to unhurried. Amenities include 54 holes of golf on three courses, indoor and outdoor swimming pools, tennis courts, a 14-acre R/C flying field, bocce, racquetball and basketball courts, fitness center, health club and spa, restaurants, cultural venues, and much more. Residents can also participate in over 175 clubs, leagues, hobbies, and lifelong learning opportunities.

Homes start in the $200k's.

Get more info. from On Top of the World

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