Cypress Ridge Kissimmee
Homes for Sale in Wimauma, FL
All 271 homes for sale in Wimauma, FL · median $362,000 · 11 townhomes for sale in Wimauma · 184 homes for sale in 33598 · Hillsborough County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, cypress ridge in Wimauma, FL has 1 home for sale. Homes listed or recently sold were built 2018 - 2021; 7 of 7 report an HOA (median $250/mo); none of the 7 geocoded homes sit in a FEMA special flood hazard zone (median elevation 86 ft).

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 Kissimmee right now
🔴 Seller-leaning market. 2.0 months of supply and 0% of the inventory already under contract give sellers the pressure advantage.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 September 12, 2026. Confidence: Low (1 active and pending listings, 0 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 15, 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 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.
Stellar MLS sales records identify 6 homes in cypress ridge that have changed hands since 2025, built between 2025 and 2026 (median 2026), with a median living area of about 2,430 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.
The setting & the homes.
Aerial and on-site photos of Cypress Ridge Kissimmee. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Cypress Ridge Kissimmee; content deemed reliable but not guaranteed.
Who Cypress Ridge Kissimmee 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
The market around Cypress Ridge Kissimmee
Cypress Ridge Kissimmee is too small for its own price trend, so here is the market around it.
In ZIP 33598, 331 homes are on the market and 25% are under contract — a steady corner of Wimauma.
Across Hillsborough County, 6,274 homes are active and 1,939 pending (24% under contract).
In ZIP 33598 (Wimauma), 932 homes closed in the last 12 months at a median of $360K ($174/sq ft), down 4.9% year over year, with a median 38 days on market. Right now 169 active and 57 pending listings put supply at about 3.7 months - a balanced market. See the live ZIP 33598 housing market and the Hillsborough County market.
ZIP and county figures describe the wider market, not Cypress Ridge Kissimmee specifically. Momentum Research analysis of MLS records.
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 September 2026 through September 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in Cypress Ridge Kissimmee
Live MLS inventory for Cypress Ridge Kissimmee. 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 Kissimmee listings as of 2026-09-14, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2025 through 2025. Tap any home to ask about it.
Cypress Ridge Kissimmee 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 Kissimmee
- 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.
The Cypress Ridge Kissimmee buying strategy.
If we were buying in Cypress Ridge Kissimmee 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.
Come strong and clean. Homes here move, so lead with your best terms and financing ready rather than a low anchor.
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 Kissimmee.
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 Kissimmee. The deal is won or lost on condition, the comps, and the renovation math.
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 Kissimmee in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $250/month (about $3,000/yr) · median of 21 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $250 per month ($3,000 a year) - the median AssociationFee across 21 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.
Tools for a Cypress Ridge Kissimmee 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 Kissimmee 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 Kissimmee, 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 Kissimmee home worth?
Get a no-obligation home value based on real comparable sales in Cypress Ridge Kissimmee, 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 Wimauma →
Recently off market in cypress ridge
Homes in cypress ridge that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 2 on record.
- 2724 Pleasant Cypress Circle · off market
- 2759 Pleasant Cypress Circle · off market
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Osceola County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Osceola County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
CYPRESS RIDGE Market Scorecard
CYPRESS RIDGE is currently a strong seller's market. About 2.0 months of supply, a median asking price of $335,995, and homes go under contract in about 112 days.
Typical home value in the 34741 ZIP is $286,616, about 14.2% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Frequently Asked Questions
Is Cypress Ridge Kissimmee a buyer's or seller's market right now?
Who is the best real estate agent for Cypress Ridge Kissimmee?
How do I find a top Wimauma real estate agent who knows Cypress Ridge Kissimmee?
Can Momentum Realty connect me with an agent for Cypress Ridge Kissimmee?
Should you buy in Cypress Ridge Kissimmee?
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: September 14, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2025 (3 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 →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how cypress ridge fits the bigger picture — live prices, inventory, and Momentum Scores:
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