Village Overview
Why Buyers Choose Hemingway
Hemingway sits at the premium tier of the south-of-466 resale market. It is regularly cited in buyer forums and among residents as one of the more desirable villages in the section — a combination of home quality, community feel, and positioning. That reputation shows in the price, which is at the upper range of south-of-466 resale.
Late 2000s construction with floor plans that push into the larger south-section range. Bond balances are at the upper end of what you will find in south-of-466 — not Fenney territory, but meaningful. The premium positioning of the village is supported by strong resale demand and typically faster absorption of available inventory compared to some of its neighbors.
Bond note: Hemingway bonds typically range $14K–$26K depending on the specific property's construction date and how much the previous owner paid down. Always request the CDD district payoff statement during your inspection period — before you commit. Two homes at similar prices in this village can carry meaningfully different bond balances.
At a Glance
Hemingway Village Facts
| Location | South of Route 466, The Villages, FL — Sumter County |
| Built | Late 2000s |
| Home Size | 1,700–2,400 sq ft typical |
| Price Range | $340K–$505K (resale, 2026 estimate) |
| CDD Bond Range | $14K–$26K — must verify per property before offering |
| County | Sumter County |
| Nearest Town Square | Brownwood Paddock Square — golf cart access |
| New Construction | No — resale only |
| Lifestyle Fee | ~$195/month (2026) — same across all of The Villages |
Honest Assessment
Hemingway Pros & Considerations
Advantages
- Premium reputation in south-of-466 resale market
- Larger homes — upper end of south-section floor plan range
- Late 2000s construction quality
- Strong resale demand — faster absorption than typical
- Consistent appreciation history
Considerations
- Bond $14K–$26K — upper end for south section; verify carefully
- Upper-premium pricing in south zone
- Sumter County taxes
Orlando Metro — Live Market Data
Redfin · March 2026
$410,000
Median Sale Price
51 days
Days on Market
18,265
Metro Active Listings
South-of-466 Village Comparisons