OAKS AT CYPRESS WOODS THE
Homes for Sale in KISSIMMEE, FL
True comps, carrying-cost math, and listings before the portals.
This is a small-inventory read: a single active listing and only one closing in the recent window are driving a 12-month supply figure. That math says more about how few transactions this community sees than about genuine oversupply, so treat the 'buyer-leaning' label as a signal of thin activity rather than a glut of competing homes.
With so little on the market, a buyer has almost no side-by-side comparison to work with, and a seller has almost no recent-sale benchmark to price against. Both sides need to lean on direct comparables from nearby Kissimmee inventory rather than what little is showing inside the community itself.
OAKS AT CYPRESS WOODS THE right now
🟢 Buyer-leaning market. 12.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of August 2, 2026. Confidence: Low (1 active and pending listings, 1 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Oaks At Cypress Woods sits in Kissimmee within Osceola County as a gated-feel, amenity-supported community, but current MLS activity here is minimal, which limits how much the numbers alone can tell a buyer or seller.
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.
The setting & the homes.
Aerial and on-site photos of OAKS AT CYPRESS WOODS THE. Swipe to explore the community.
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OAKS AT CYPRESS WOODS THEWho OAKS AT CYPRESS WOODS THE is best for.
Best for
- A buyer prioritizing amenity access (clubhouse, recreation facilities) over having many homes to compare
- A buyer or seller willing to verify HOA amenity terms and access directly rather than relying on listing descriptions
- A buyer comfortable pricing off broader Kissimmee-area comparables rather than in-community sales history
Probably not for
- A buyer who wants several active listings to compare floor plans, condition, and pricing side by side
- A seller expecting a deep pool of recent in-community closings to benchmark a list price against
- A buyer unwilling to do independent due diligence on amenity access and HOA terms before writing an offer
The market around OAKS AT CYPRESS WOODS THE
OAKS AT CYPRESS WOODS THE is a small community — 7 recorded sales on file, most recently in 2025 — too few for its own price trend. Here is the market around it.
In ZIP 34758, 395 homes are on the market and 29% are under contract — a steady corner of KISSIMMEE.
Across Osceola County, 4,437 homes are active and 1,149 pending (21% under contract).
Homes here are single family residence.
ZIP and county figures describe the wider market, not OAKS AT CYPRESS WOODS THE specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in OAKS AT CYPRESS WOODS THE, 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 August 2026 through August 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in OAKS AT CYPRESS WOODS THE
Live MLS inventory for OAKS AT CYPRESS WOODS THE. 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 OAKS AT CYPRESS WOODS THE listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2012 through 2026. Tap any home to ask about it.
OAKS AT CYPRESS WOODS THE 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 OAKS AT CYPRESS WOODS THE
- Association Recreation - Lease · reported on 1 of 1 listings
- Association Recreation - Owned · reported on 1 of 1 listings
- Clubhouse · reported on 1 of 1 listings
- Community Mailbox · reported on 1 of 1 listings
- Security Fencing/Lighting/Alarms · reported on 1 of 1 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
- Floral Ridge Elementary · Elementary
- Harmony Middle · Middle
- Poinciana High School · High
Zoned schools reflect the assignments reported on recent OAKS AT CYPRESS WOODS THE 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 OAKS AT CYPRESS WOODS THE address.
The OAKS AT CYPRESS WOODS THE buying strategy.
If we were buying in OAKS AT CYPRESS WOODS THE 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 OAKS AT CYPRESS WOODS THE.
A Market With Almost No Data to Read
With one active listing and a single closing feeding the supply calculation, this community's 12-month supply figure is a mathematical artifact of low volume, not a market forecast. It would be a mistake to read it the way you would a 12-month supply number in a high-volume subdivision with dozens of recent sales.
The amenity package reported across this community's listings includes a clubhouse, both leased and owned recreation facilities, community mailbox service, and security fencing, lighting, and alarm infrastructure. Access and current condition of any of these should be verified directly with the HOA before a buyer treats them as settled facts.
The location and the amenities are priced into every listing in OAKS AT CYPRESS WOODS THE. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community this thin on active listings, pricing and timing decisions can't rely on the community's own data alone. We pull comparable closings from the broader Kissimmee market, confirm HOA amenity details directly rather than taking listing notes at face value, and help you build a realistic offer or list strategy when the subject community itself isn't giving you enough to go on.
OAKS AT CYPRESS WOODS THE in 15 seconds.
HOA, CDD & Fees
- Mandatory HOA. Confirm current dues
- Any club/amenity membership is billed separately
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 OAKS AT CYPRESS WOODS THE 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 OAKS AT CYPRESS WOODS THE sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in OAKS AT CYPRESS WOODS THE, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your OAKS AT CYPRESS WOODS THE home worth?
Get a no-obligation home value based on real comparable sales in OAKS AT CYPRESS WOODS THE, 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 homes for sale in OAKS AT CYPRESS WOODS THE on the map →
OAKS AT CYPRESS WOODS THE Market Scorecard
OAKS AT CYPRESS WOODS THE is currently a strong buyer's market. About 12.0 months of supply, a median asking price of $298,999, and homes go under contract in about 238 days.
Go deeper: county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Frequently Asked Questions
Is OAKS AT CYPRESS WOODS THE a buyer's or seller's market right now?
How many homes are in OAKS AT CYPRESS WOODS THE?
What share of OAKS AT CYPRESS WOODS THE is owner-occupied?
When were the homes in OAKS AT CYPRESS WOODS THE built?
Do cash buyers compete in OAKS AT CYPRESS WOODS THE?
Who is the best real estate agent for OAKS AT CYPRESS WOODS THE?
How do I find a top KISSIMMEE real estate agent who knows OAKS AT CYPRESS WOODS THE?
Can Momentum Realty connect me with an agent for OAKS AT CYPRESS WOODS THE?
Should you buy in OAKS AT CYPRESS WOODS THE?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near OAKS AT CYPRESS WOODS THE with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (3 streets, ZIP 34758)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2012 (7 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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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 your area comps.
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