Pennyroyal
Homes for Sale in Kissimmee, FL

Pennyroyal Kissimmee is a newly built enclave in Osceola County where nearly every home dates to 2022 or later, giving the community a consistent, low-mileage housing stock rather than the mixed vintages typical of older subdivisions.

Stellar MLS sales records identify 38 homes in Pennyroyal that have changed hands since 2022, built between 2022 and 2024 (median 2023), with a median living area of about 2,312 sq ft and a typical 4-bedroom, 2.5-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Pennyroyal is too small for its own price trend, so here is the market around it.

In ZIP 34744, 418 homes are on the market and 21% are under contract — a steady corner of Kissimmee.

Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).

In ZIP 34744 (KISSIMMEE), 785 homes closed in the last 12 months at a median of $406K ($215/sq ft), up 1.8% year over year, with a median 34 days on market. Right now 126 active and 26 pending listings put supply at about 6.6 months - a balanced market. See the live ZIP 34744 housing market and the Osceola County market.

ZIP and county figures describe the wider market, not Pennyroyal specifically. Momentum Research analysis of MLS records.

• Partin Settlement Elem · Elementary
• Neptune Middle (6-8) · Middle
• Gateway High School (9 12) · High

Zoned schools reflect the assignments reported on recent Pennyroyal listings and can change; always confirm with Osceola County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Pennyroyal address.

At 92 homes total, Pennyroyal is a compact community, and with construction concentrated in a tight 2022-2024 window, there is little variation in age across the neighborhood. That uniformity simplifies part of the buyer's job - condition differences are more likely to come from upgrades and upkeep than from decades of deferred maintenance - but it also means the resale market here is still young and thin, reflected in the 24-month supply figure and a trailing count of just 4 active listings.

A homestead share of roughly 60% indicates a majority of homes carry an owner-occupied exemption, a data point worth factoring into how much of the community's housing stock tends to turn over versus stay put in a given cycle. Combined with the deed-restricted, amenity-rich setup - clubhouse, pool, fitness center, dog park, playground, basketball court, and an owner-managed recreation association - this points to a community built around a defined set of shared facilities rather than a loose, amenity-light layout.

A 4-listing active market is not a place to price or negotiate by feel - with so few comparables, we pull the specific closed and pending data for Pennyroyal rather than leaning on county-wide averages, and we walk you through what the deed restrictions and HOA-owned recreation setup actually mean for cost and use before you're under contract.

Listings in this community report association dues of about $150 per month ($1,800 a year) - the median AssociationFee across 18 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.