The Oaks
Homes for Sale in Kissimmee, FL
All 2,959 homes for sale in KISSIMMEE, FL · median $374,000 · 581 homes for sale in 34746 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Homes listed or recently sold were built 1996 - 2016; 4 of 4 report an HOA (median $24/mo); 1 of the 4 geocoded homes sit in a FEMA special flood hazard zone (median elevation 63 ft). As of September 2026, the MLS records 22 closed sales in the Oaks in Kissimmee, FL since 2015, the most recent in May 2026. Across Kissimmee as a whole, 2,523 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,265 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,910 ($5,310 with the full homestead exemption).
Villages & sections of the Oaks Kissimmee
the Oaks Kissimmee in Kissimmee, FL is a master-planned community recorded as 2 named villages and sections in the MLS; 7 homes are for sale or pending across them today. Each village has its own page with its listings, sales history and HOA/CDD facts.
- Osprey Cove at the Oaks Kissimmee · 4 for sale
- Eagles Nest at the Oaks Kissimmee · 3 for sale · 1 sold/12 mo
| Location | KISSIMMEE, Osceola County, FL · ZIP 34746, 34758, 34771 |
|---|---|
| Homes in the community | 656 (FL DOR 2025 assessment roll) |
| Years built | 1987–2007 (median 2000) |
| Typical living area | 2,553 sq ft (median) |
| Amenities listed by sellers | Deed Restrictions, Park, Tennis Court(s), Golf, Playground, Community Mailbox |
| For sale right now | 0 active, 1 pending |
| Owner-occupied (homestead) share | 66% |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “THE OAKS key facts,” movewithmomentum.com/neighborhoods/the-oaks-kissimmee, data as of August 2, 2026.
Last 30 days in The Oaks: 1 new listing (median asking $510,000). As of September 28, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
The setting & the homes.
Aerial and on-site photos of The Oaks. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in The Oaks; content deemed reliable but not guaranteed.
The market around The Oaks
The Oaks is a small community — 51 recorded sales on file, most recently in 2023 — too few for its own price trend. Here is the market around it.
In ZIP 34746, 995 homes are on the market and 21% are under contract — a steady corner of Kissimmee.
Across Osceola County, 4,437 homes are active and 1,149 pending (21% under contract).
The housing mix here is 98% single family residence, 2% ?.
ZIP and county figures describe the wider market, not The Oaks specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in The Oaks
Live MLS inventory for The Oaks. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending The Oaks listings as of 2026-09-28, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2026. Tap any home to ask about it.
Every Home for Sale in The Oaks Kissimmee Right Now (2)
All 2 active and pending The Oaks Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 2912 Boating Boulevard · $510,000 · 4 bd / 2 ba · listed Aug 28, 2026 · listed by Mark Spain Real Estate
- 1524 The Oaks Boulevard · $534,900 · 4 bd / 2.5 ba · listed Jun 27, 2026 · listed by Premier Sothebys Int'L Realty
The Oaks on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at The Oaks
- Park · reported on 3 of 3 listings
- Tennis Court(s) · reported on 2 of 3 listings
- Deed Restrictions · reported on 2 of 3 listings
- Golf · reported on 1 of 3 listings
- Community Mailbox · reported on 1 of 3 listings
- Golf Carts OK · reported on 1 of 3 listings
- Fence Restrictions · reported on 1 of 3 listings
- Playground · reported on 1 of 3 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Osceola County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Pleasant Hill Elem · Elementary
- Horizon Middle · Middle
- Liberty High · High
Zoned schools reflect the assignments reported on recent The Oaks 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 The Oaks address.
Shop the zone: Homes zoned for Liberty High High School
The The Oaks buying strategy.
If we were buying in The 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 The Oaks.
A closer look at the The Oaks market
The housing stock is 656 homes built between 1987 and 2007, and 66% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in The Oaks. The deal is won or lost on condition, the comps, and the renovation math.
HOA, CDD & Fees
- HOA dues reported around $24/month (about $288/yr) · median of 64 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $24 per month ($288 a year) - the median AssociationFee across 64 MLS records, normalised to a monthly figure; most are billed annually. 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.
Tools for a The 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 The Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in The 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 The Oaks home worth?
Get a no-obligation home value based on real comparable sales in The 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.
See all homes for sale in Kissimmee →
16% of homes for sale in ZIP 34746 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-09-20).
Frequently Asked Questions
How many homes are in The Oaks?
What share of The Oaks is owner-occupied?
When were the homes in The Oaks built?
Do cash buyers compete in The Oaks?
Who is the best real estate agent for The Oaks?
How do I find a top Kissimmee real estate agent who knows The Oaks?
Can Momentum Realty connect me with an agent for The Oaks?
Where is The Oaks, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 28, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (12 streets, ZIP 34746/34758/34771)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2015 (22 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.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how THE OAKS fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near The Oaks with Momentum Realty’s local guides.