Cypress Cay
Homes for Sale in Kissimmee, FL
All 2,933 homes for sale in KISSIMMEE, FL · median $373,400 · 734 townhomes for sale in KISSIMMEE · 569 homes for sale in 34746 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Cypress Cay in Kissimmee, FL has 6 homes for sale and 1 pending, asking from $314,900 to $369,000 (median $349,188). Over the 12 months ending 2026-09-12, 3 recorded sales closed at a median of $320,000, $184 per square foot, a median 125 days on market, sellers accepting 88% of original asking (-14% versus the prior year). Homes listed or recently sold were built 2022 - 2024; 11 of 11 report an HOA (median $300/mo); none of the 11 geocoded homes sit in a FEMA special flood hazard zone (median elevation 80 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $4,870 ($4,270 with the full homestead exemption).
Homes For Sale Right Now in Cypress Cay
Live MLS inventory for Cypress Cay. 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 · 782 daysTop listing
Active · 46 days
Active · 29 days
Active · 23 days
Active · 110 days
Active · 149 days
Pending · 231 daysActive and pending Cypress Cay listings as of 2026-09-14, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026. Tap any home to ask about it.
Cypress Cay right now
🟢 Buyer-leaning market. 18.0 months of supply and 14% 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 September 12, 2026. Confidence: Medium (7 active and pending listings, 3 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($320K) is down 13.7% from the prior 12 months ($371K). With about 21 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 September 12. Confidence: Low (3 and 26 sales in the two windows).
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 Cay market snapshot (as of September 12, 2026): the median sale price is about $320K ($184 per sq ft over the trailing 12 months of closed sales), a median 125 days on market for closed sales, and 18.0 months of supply, a buyer-leaning market. The trailing-12-month median is down 14% from the prior 12 months, computed from record-level Stellar MLS closed sales (3 closings in the current window).
In ZIP 34746 (KISSIMMEE), 1,615 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.5% year over year, with a median 67 days on market. Right now 421 active and 72 pending listings put supply at about 6.7 months - a buyer's market. See the live ZIP 34746 housing market and the Osceola County market.
Stellar MLS sales records identify 146 homes in Cypress Cay that have changed hands since 2022, built between 2021 and 2024 (median 2023), with a median living area of about 1,699 sq ft and a typical 3-bedroom, 2.5-bath layout; 100% are townhomes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Flood zones in Cypress Cay: of 10 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Kissimmee.
The setting & the homes.
Aerial and on-site photos of Cypress Cay. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Cypress CayPhotos from Stellar MLS listings in Cypress Cay; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($320K) IS the median in the snapshot above, and the move from 2025 ($371K) IS the -13.7% one-year change.
Windows contain 0 to 70 sales each (3 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 2021 through 2026. Deemed reliable but not guaranteed.
CYPRESS CAY Market Scorecard
CYPRESS CAY is currently a strong buyer's market. About 18.0 months of supply, a median asking price of $349,188, and homes go under contract in about 78 days.
Typical home value in the 34746 ZIP is $360,381, about 6.8% 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.
Housing distress & ownership in Cypress Cay Kissimmee, 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.
Cypress Cay 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 Cay
- Playground · reported on 9 of 11 listings
- Pool · reported on 9 of 11 listings
- Dog Park · reported on 5 of 11 listings
- Park · reported on 5 of 11 listings
- Basketball Court · reported on 4 of 11 listings
- Community Mailbox · reported on 4 of 11 listings
- Deed Restrictions · reported on 4 of 11 listings
- Irrigation-Reclaimed Water · reported on 2 of 11 listings
- Clubhouse · reported on 2 of 11 listings
- Cable TV · reported on 1 of 11 listings
- Trail(s) · reported on 1 of 11 listings
- Fence Restrictions · reported on 1 of 11 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
- Poinciana High School · High
Zoned schools reflect the assignments reported on recent Cypress Cay 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 Cay address.
Shop the zone: Homes zoned for Poinciana High School
The Cypress Cay buying strategy.
If we were buying in Cypress Cay 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 Cay.
A closer look at the Cypress Cay market
At a median of $184 per square foot, Cypress Cay prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 18.0 months of supply, a buyer-leaning market and the trailing-12-month median down 14% year over year. Homes that do trade take a median 125 days on market, useful leverage on any listing that has lingered.
The location and the amenities are priced into every listing in Cypress Cay. 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 Cay 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 (1.5). Basis: Recent Direction -13.7% year-over-year; Liquidity & Demand 18.0 months of supply; Pricing Power 87.7% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $309/month (about $3,708/yr) · median of 30 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $309 per month ($3,708 a year) - the median AssociationFee across 30 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 Cay 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 Cay sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cypress Cay, 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 Cay home worth?
Get a no-obligation home value based on real comparable sales in Cypress Cay, 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 →
Frequently Asked Questions
What is the median home price in Cypress Cay?
How long do homes in Cypress Cay take to sell?
Is Cypress Cay a buyer's or seller's market right now?
Who is the best real estate agent for Cypress Cay?
How do I find a top Kissimmee real estate agent who knows Cypress Cay?
Can Momentum Realty connect me with an agent for Cypress Cay?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2021 (125 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.
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See how Cypress Cay fits the bigger picture — live prices, inventory, and Momentum Scores:
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