San Antonio's most-compared 55+ communities. Del Webb resale vs. Toll Brothers new construction. Bexar County taxes vs. the Kendall County MUD. Military community culture vs. Hill Country walkability. The complete comparison.
These are the two communities buyers most often pit against each other in the San Antonio market. Both are high-quality 55+ options with resort amenities and strong community identity. Both attract serious buyers who have researched carefully. And yet they are fundamentally different choices — different counties, different tax structures, different community stages, different location tradeoffs.
Most comparison sites — 55places, Zillow, local agent blogs — stop at amenity lists and price ranges. This comparison goes deeper: what do you actually pay to own each, what community do you actually join, and which profile fits which buyer.
| Category | Hill Country Retreat | Regency at Esperanza |
|---|---|---|
| Builder | Del Webb + Village Builders (Pulte) | Toll Brothers |
| Status | Fully built, resale only | Active build (opened ~2023) |
| Location | Alamo Ranch, far west San Antonio | Boerne, 35 miles north of San Antonio |
| County | Bexar | Kendall (MUD #1) |
| Total homes | 1,904 (all built) | TBD (active phases) |
| Floor plans | 29 total (23 Del Webb + 6 VB), 1,109–2,838 sq ft | 15 plans, 1,625–3,206 sq ft, all single-story |
| Price range | Mid $200s–high $500s (resale) | $500K–$900K+ (new construction) |
| HOA structure | Single HOA: $185/month ($556/quarter) | Dual HOA: ~$250–350/month combined |
| HOA includes | Exterior maintenance, landscaping, trash | Regency clubhouse + Esperanza master plan |
| Amenities (exclusive) | 28,000 sq ft Resort: indoor/outdoor pools, fitness, tennis, pickleball, bocce, ballroom | Resort pool, fitness, pickleball, bocce, club spaces |
| Master plan amenities | None (standalone community) | Reunión Parque, trails, retail/restaurant, mixed-use |
| Effective property tax | 1.8–2.3% (Bexar) — with 2025 senior exemptions significantly lower for 65+ | 2.4–2.7% (Kendall MUD) — limited senior exemptions |
| 65+ tax exemption advantage | $200,000 combined school exemption + school tax freeze + City of SA $85K | Smaller Kendall exemptions, no SA municipal exemption, school freeze applies |
| Military buyer density | High — JBSA proximity, explicit military marketing | Standard — not military-focused |
| Downtown walkability | None (suburban Alamo Ranch) | Golf-cart accessible to Boerne Hill Country Mile (~5 min) |
| Distance to major medical | 10–15 min to major SA hospitals | 30–45 min to major SA hospitals |
| Construction era | 2000s–2010s (10–20 year old resale) | 2023–present (new construction, builder warranty) |
| Community maturity | Fully established — clubs, social fabric, reputation documented | Forming — community culture still developing |
To compare accurately, we model homes at different price points and the all-in monthly carrying cost for a 65+ buyer with the 2025 exemption structure applied where applicable.
Note: These are different home values ($400K vs. $600K), reflecting typical price points at each community. The cost differential reflects both the price difference and the structural tax gap between Bexar and Kendall MUD.
To isolate the tax impact, consider the same $500,000 home value in both counties for a 65+ buyer:
| Cost Line | Bexar County — $500K (65+) | Kendall MUD — $500K (65+) |
|---|---|---|
| Annual property tax | ~$9,232/year | ~$12,750/year |
| Monthly property tax | ~$769/month | ~$1,063/month |
| Annual tax gap | $3,518/year extra in Kendall MUD | |
| Monthly tax gap | $293/month extra in Kendall MUD | |
These are genuine advantages, not concession points:
New construction. You know the full maintenance history because there is no maintenance history. Toll Brothers warranty covers structural defects for 10 years, systems for 2 years. You're not inheriting someone else's deferred HVAC service, outdated plumbing, or aging appliances.
Walkable downtown access. Boerne's Hill Country Mile is the only walkable downtown adjacent to any 55+ community in the San Antonio market. For buyers who value authentic small-town character and car-free access to local shops and restaurants, this is a real differentiator.
Hill Country location and character. Boerne's elevation, landscape, and Hill Country aesthetic are genuinely different from suburban San Antonio. If that setting matters to you — and for many buyers it does — Regency provides access to it in a way Hill Country Retreat (Alamo Ranch suburban) cannot.
Master plan breadth. Esperanza's Reunión Parque, retail, and restaurant development gives Regency residents infrastructure beyond the 55+ community gates — mixed-use access that standalone communities like Hill Country Retreat don't offer.
Property tax — structurally and by a large margin. The combination of Bexar County's 2025 senior exemptions and no MUD tax means 65+ buyers at Hill Country Retreat pay dramatically less in property tax on comparable home values. At the same home value, the gap is approximately $285–$300/month — the Bexar exemptions and absent MUD together. Over 15 years on a $500K home, that difference totals approximately $51,000–$54,000 in property tax alone.
Community maturity. You can visit, tour, talk to 20 residents, sit in the ballroom on a Tuesday afternoon, and know exactly what you're buying. The clubs are established, the social calendar is real, the amenity quality is documented. There's no uncertainty about what the community will be.
Lower entry price. Resale inventory at $250K–$500K creates genuine affordability options that new Toll Brothers construction in the $500K–$900K range cannot match.
Medical proximity. 10–15 minutes to major San Antonio hospitals vs. 30–45 minutes from Boerne. For healthy retirees in their early 60s, this may be acceptable. For anyone with chronic conditions or planning for 20+ years of aging in place, the difference is real.
Single HOA simplicity. One entity, one bill, no dual-HOA governance complexity or split capital assessment risk.
Hill Country Retreat buyers underestimate how much the community's military culture shapes daily life. This isn't good or bad — it's just real. If you're not military and you expected a generic resort community, the organized, committee-driven, service-oriented culture can feel unfamiliar. Go in knowing.
Regency at Esperanza buyers underestimate the MUD tax — consistently and sometimes dramatically. Texas "no income tax" marketing is pervasive, and Kendall County's location north of San Antonio sounds financially straightforward. It isn't. Model the full MUD cost before you fall in love with a Toll Brothers model home in Boerne.