CYPRESS RIDGE
Homes for Sale in KISSIMMEE, FL
True comps, carrying-cost math, and listings before the portals.
Cypress Ridge sits in a buyer-leaning posture right now, with nine months of supply against just three active listings across a 375-home community. That combination is unusual: the raw count of homes for sale is thin, but the pace of sales relative to that supply is slow enough to keep leverage with buyers rather than sellers.
With homestead share at zero, none of the current owners have filed for a homestead exemption here, which points to a community currently weighted toward non-primary or investment ownership rather than owner-occupied use. That matters for how you negotiate and how you underwrite a purchase — pricing conversations here are likely to be shaped more by carrying-cost math than by move-in urgency.
CYPRESS RIDGE right now
🟢 Buyer-leaning market. 7.2 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: Medium (3 active and pending listings, 4 closed sales in 12 months).
🟡 Off the recent peak. The trailing-12-month median ($330K) is down 6.7% from the prior 12 months ($353K). With about 2 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Low (4 and 3 sales in the two windows).
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
CYPRESS RIDGE market snapshot (as of August 2, 2026): the median sale price is about $330K ($187 per sq ft over the trailing 12 months of closed sales), a median 74 days on market for closed sales, and 7.2 months of supply, a buyer-leaning market. The trailing-12-month median is down 7% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).
Cypress Ridge is a gated, deed-restricted community in Wimauma (Hillsborough County) built around a small set of shared amenities rather than a large resort-style package, with reclaimed irrigation service keeping landscaping costs in check for the HOA.
The setting & the homes.
Aerial and on-site photos of CYPRESS RIDGE. Swipe to explore the community.
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CYPRESS RIDGEWho CYPRESS RIDGE is best for.
Best for
- Buyers who want deed-restricted, gated community structure without guard-staffed access
- Investment-minded buyers comfortable underwriting in a market with zero current homestead-exemption share
- Patient buyers who can work with a limited pool of active listings and slower absorption
Probably not for
- Buyers who need a large pool of active comparables to negotiate confidently
- Buyers seeking an extensive amenity package beyond a pool, playground, and trails
- Buyers who want a fast, competitive-offer environment rather than a buyer-leaning one
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($330K) IS the median in the snapshot above, and the move from 2025 ($353K) IS the -6.7% one-year change.
Windows contain 0 to 4 sales each (4 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2019 through 2026. Deemed reliable but not guaranteed.
CYPRESS RIDGE Market Scorecard
CYPRESS RIDGE is currently a buyer's market. About 7.2 months of supply, a median asking price of $345,990, and homes go under contract in about 8 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.
Housing distress & ownership in CYPRESS RIDGE, 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 CYPRESS RIDGE
Live MLS inventory for CYPRESS RIDGE. 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 CYPRESS RIDGE listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2019 through 2026. Tap any home to ask about it.
CYPRESS RIDGE 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 CYPRESS RIDGE
- Playground · reported on 7 of 7 listings
- Pool · reported on 5 of 7 listings
- Community Mailbox · reported on 2 of 7 listings
- Gated Community - No Guard · reported on 2 of 7 listings
- Trail(s) · reported on 2 of 7 listings
- Deed Restrictions · reported on 2 of 7 listings
- Irrigation-Reclaimed Water · reported on 2 of 7 listings
- Gated · reported on 1 of 7 listings
- Gated Community · reported on 1 of 7 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
- Kissimmee Middle · Middle
- Osceola County School for Arts · High
Zoned schools reflect the assignments reported on recent CYPRESS RIDGE 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 CYPRESS RIDGE address.
The CYPRESS RIDGE buying strategy.
If we were buying in CYPRESS RIDGE 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 CYPRESS RIDGE.
A thin market moving at its own pace
Three active listings out of 375 total homes is a small slice of inventory by any measure. Normally that would signal a tight, competitive market, but the nine-month supply figure tells the other half of the story: at the current sales pace, it would take roughly nine months to clear what's on the market today. That's a buyer-leaning read — supply is outrunning demand even though the absolute number of homes for sale is low.
The amenity set — playground, pool, trails, community mailbox, and gated access without a guard — is standard deed-restricted community infrastructure, not a luxury package. Deed restrictions and HOA governance are in place, so buyers should expect architectural and use guidelines typical of a managed community, and should confirm current rules and fees directly with the HOA rather than assume anything from the listing history.
The location and the amenities are priced into every listing in CYPRESS RIDGE. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in CYPRESS RIDGE buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (4.9). Basis: Recent Direction -6.7% year-over-year; Liquidity & Demand 7.2 months of supply; Pricing Power 96.1% sale-to-list. Refreshed with each data update.
Why work with Momentum here
With only three active listings, there's little room for guesswork — we track this community's Stellar MLS activity closely enough to flag a new listing or a shift in the supply picture before it's obvious from the outside, and we push directly to the HOA for amenity and restriction verification rather than relying on secondhand listing notes.
CYPRESS RIDGE 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 CYPRESS RIDGE 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 CYPRESS RIDGE sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in CYPRESS RIDGE, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your CYPRESS RIDGE home worth?
Get a no-obligation home value based on real comparable sales in CYPRESS RIDGE, 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 CYPRESS RIDGE on the map →
Frequently Asked Questions
What is the median home price in CYPRESS RIDGE?
How long do homes in CYPRESS RIDGE take to sell?
Is CYPRESS RIDGE a buyer's or seller's market right now?
Do cash buyers compete in CYPRESS RIDGE?
Who is the best real estate agent for CYPRESS RIDGE?
How do I find a top KISSIMMEE real estate agent who knows CYPRESS RIDGE?
Can Momentum Realty connect me with an agent for CYPRESS RIDGE?
Should you buy in CYPRESS RIDGE?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near CYPRESS RIDGE with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2019 (13 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 your area comps.
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