Pine Oaks
Homes for Sale in Kissimmee, FL
All 3,127 homes for sale in Kissimmee, FL · median $375,000 · 329 homes for sale in 34744 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of November 2026, the MLS records 11 closed sales in Pine Oaks in Kissimmee, FL since 2004, the most recent in November 2025. Across Kissimmee as a whole, 4,246 homes closed in the last 12 months at a median of $360,000, 64 median days on market, with 2,907 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,480 ($4,880 with the full homestead exemption).
Price in Pine Oaks is driven by condition and vintage more than by any single template. With a build range spanning roughly a century and a median year built around 1988, no two homes carry the same bones, so the spread here is wide and condition-led. There is no starter-versus-luxury tier to point to; there is renovated versus original, and that gap is where most of the negotiation happens.
A little over half the homes carry a homestead exemption, which tells you this is more owner-occupied than churn-driven. For a seller, that means comparatively steady turnover and buyers who look hard at systems and updates. For a buyer, it means you should underwrite each house on its own merits — age of roof, mechanicals, and finishes — rather than assume a neighborhood-wide standard.
Figures in this note are as of July 14, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Pine Oaks right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Pine Oaks is a small, established pocket in Kissimmee where the housing stock ranges from early-century to brand-new, so the community reads as varied rather than uniform. Median living space sits above 2,300 square feet, which points to genuinely usable, mid-sized homes rather than compact builds.
Stellar MLS sales records identify 18 homes in Pine Oaks that have changed hands since 2005, built between 1920 and 2017 (median 1985), with a median living area of about 2,326 sq ft and a typical 4-bedroom, 3-bath layout; 94% 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.
County records show 3 qualified sales in Pine Oaks across 2024–2024, median $910,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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.
Who Pine Oaks is best for.
Best for
- Buyers who want more living space and will trade uniformity for a house with real square footage
- Renovation-minded buyers willing to underwrite an older home's systems in exchange for value
- Long-hold buyers who value a steady, owner-occupied community over quick turnover
Probably not for
- Buyers who need matching, new-construction finishes across the whole street
- Anyone unwilling to budget for inspections and potential system updates on older stock
- Buyers wanting a predictable price tier rather than condition-driven pricing
The market around Pine Oaks
Pine Oaks is too small for its own price trend, so here is the market around it.
In ZIP 34744, 447 homes are on the market and 19% are under contract — a steady corner of Kissimmee.
Across Osceola County, 4,465 homes are active and 1,093 pending (20% under contract).
In ZIP 34744 (Kissimmee), 271 homes closed in the last 12 months at a median of $390K ($212/sq ft), up 5.3% year over year, with a median 36 days on market. See the live ZIP 34744 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not Pine Oaks specifically. Momentum Research analysis of MLS records.
The Pine Oaks buying strategy.
If we were buying in Pine Oaks today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Pine Oaks.
A century of housing stock in one place
With just over 100 homes and a build range from 1920 to 2024, Pine Oaks is the kind of community where you shop house by house. The median year built near 1988 anchors the middle, but you will find genuinely old construction alongside recent builds on the same walk. That mix rewards buyers who can read a house and punishes anyone expecting consistency.
Median living area of about 2,300 square feet is the more reliable signal of what you get here: homes with real room, not entry-sized footprints. The practical takeaway is that inspection matters more than usual. Older homes may need updated systems; newer ones command a premium for it, and the price you pay should track directly to where a given house falls on that condition curve.
The location and the amenities are priced into every listing in Pine Oaks. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A community this varied — a century of build dates and a wide condition spread — is exactly where a generic valuation misleads. We price and negotiate off the specific house in front of you: its vintage, its systems, its updates. That is how you avoid overpaying for age or underselling a renovation in Pine Oaks.
Pine Oaks in 15 seconds.
Tools for a Pine Oaks buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Pine Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Pine Oaks, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Pine Oaks home worth?
Get a no-obligation home value based on real comparable sales in Pine Oaks, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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| Location | Kissimmee, Osceola County, FL · ZIP 34744 |
|---|---|
| Homes in the community | 26 (FL DOR 2025 assessment roll) |
| Years built | 1920–2019 (median 1987.5) |
| Typical living area | 2,766 sq ft (median) |
| Amenities listed by sellers | Security Lights, Security System |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 65% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Pine Oaks key facts,” movewithmomentum.com/neighborhoods/pine-oaks, data as of September 20, 2026.
Housing distress & ownership in Pine Oaks, Kissimmee
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period November 2026 through November 2026. Deemed reliable but not guaranteed.
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Frequently Asked Questions
How many homes are in Pine Oaks?
What share of Pine Oaks is owner-occupied?
When were the homes in Pine Oaks built?
Who is the best real estate agent for Pine Oaks?
How do I find a top Kissimmee real estate agent who knows Pine Oaks?
Can Momentum Realty connect me with an agent for Pine Oaks?
Where is Pine Oaks, and what county is it in?
Should you buy in Pine Oaks?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: November 12, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 34744)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2004 (11 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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