JENNIFER HAY
Broker Associate · Axen Realty — Central Florida 55+ Specialist
(352) 207-3600
← The Villages Guide
Area 4 · The New South

South of 44 — Fenney, Sawgrass Grove & Eastport, the newest frontier

Everything south of SR 44 was pasture a decade ago. Now it's the community's growth engine: the newest homes, nature preserves and boardwalk trails, Sawgrass Grove's market-hall dining and live music, and Eastport — the newest lakefront town center — anchoring the far south. Buyers here trade the established squares' maturity for new construction and room to breathe. Both halves of that trade are real.

30+ villages and growing Newest homes in the community Sawgrass Grove — Boxcar Stage & Market Eastport — newest town center Fenney nature trails & Hogeye Preserve
Neighborhoods

The villages of the south

The Fenney-era villages (2017 onward) opened the south; the Sawgrass and Eastport waves followed, and new villages are still being released. Proximity runs on a new map here: your hubs are Sawgrass Grove and Eastport, not the northern squares.

FenneyDeSotoMarsh BendMonarch GroveChitty ChattyMcClureRichmondSt. CatherineHawkinsBradfordCitrus GroveDeLunaLindenSt. JohnsCason HammockLake DenhamDabneyNewellWaters EdgeShady BrookMoultrie CreekWell Point

Village list per community directories, November 2026; the southern roster grows with each new release, and Middleton — the adjacent family community built for Villages employees and families — expands the area's shops and schools.

Community Calendar

What's on in the south

Sawgrass Grove

  • Nightly: free live entertainment at the Boxcar Stage, seven nights a week, under the orange-grove canopy
  • The Market at Sawgrass Grove — food hall and shops, recently revitalized with a unified vendor lineup
  • Daytime sessions and DJ sets keep the Grove busy beyond the evening shows

Eastport & the outdoors

  • Eastport Town Center — the newest lakefront square, with nightly entertainment (about 6–10 pm in its first season) around Center Stage and Central Lake
  • Fenney Nature Trail & Hogeye Path — boardwalks, marsh views and the community's best birding
  • Sunset kayaking and nature programming run through the southern recreation centers
  • Full north-end festival calendar is a drive, not a cart ride — plan square nights accordingly

Confirm current lineups and times on the official calendar: thevillages.com/entertainment.

Restaurants

Eating in the south

Sawgrass Grove & Fenney

  • Sawgrass Tavern — the Grove's full-service anchor: Celtic-inspired pub classics, dining room, patio and indoor-outdoor bar
  • The Market vendors — Southern Tender (hand-breaded chicken), Sizzle 'N Smash burgers, Papa Joe's Pizza, LUMA Mediterranean, Take 5 Coffee & Crepes, Darlin's Sweet Shop
  • Fenney Grill — the Fenney recreation-area grill, a neighborhood favorite for casual dinners after golf
  • Oak & Stone at Eastport — the new town center's headline opening for craft pizza and pours

Clubs & daily life

  • Southern recreation centers (Fenney, Ezell, Franklin and the newest regional centers) run full club calendars — southern clubs skew outdoors: kayaking, biking, nature and fishing groups thrive here
  • New executive courses keep opening with the villages; championship golf at Southern Oaks and the Shady Brook–era courses
  • Middleton's shops, restaurants and the US 301 corridor fill everyday needs; Brownwood is the nearest full square for a big night out
The Honest Version

What residents love — and don't — about the south

❤ Residents love

  • Brand-new everything. Current floor plans, energy codes and warranties — no renovation math
  • Nature. Preserves, springs and trails the built-out north doesn't have; Fenney is the standout for quiet and wildlife
  • Room to breathe. Less congestion than the core — for now
  • Eastport's upside. Buying near a town center still filling in has historically rewarded early buyers here

⚠ Residents warn

  • The bond bites here. Newer southern homes carry the community's largest CDD bonds — $20,000–$35,000+, or roughly $1,500–$2,500 a year on the tax bill. Get the exact balance in writing
  • Distance is the daily tax. The Sharon, Spanish Springs and long-time friends up north are 30–45+ minutes by cart; most southern residents drive more than they expected
  • Construction is a neighbor. New phases mean trucks, noise and changing views for years
  • Amenities are still maturing. Some southern cart paths, shops and services are catching up to the rooftops
  • Landscaping is young. Shade is a decade away in the newest villages

New construction or resale in the south — which pencils better?

I'll compare them honestly, bond included — a resale with a paid-down bond often beats the shiny new build on true cost.

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