Cypress Cay
Homes for Sale in Kissimmee, FL
All 3,104 homes for sale in Kissimmee, FL · median $375,000 · 773 townhomes for sale in Kissimmee · 797 homes for sale in 34746 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, Cypress Cay in Kissimmee, FL has 5 homes for sale and 1 pending, asking from $325,000 to $369,000 (median $344,000). Over the 12 months ending 2026-09-20, 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; 10 of 10 report an HOA (median $299/mo); none of the 10 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 · 867 daysTop listing
Active · 170 days
Active · 194 days
Active · 92 days
Active · 100 days
Pending · 231 daysActive and pending Cypress Cay listings as of 2026-10-23, 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 20, 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 20. Confidence: Low (3 and 26 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 24, 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 20, 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), 1,623 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.3% year over year, with a median 67 days on market. Right now 435 active and 80 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.
County records show 78 qualified sales in Cypress Cay across 2024 - 2025 (74 in 2024, 4 in 2025), median $374,200 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Cypress Cay: of 9 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.
Cypress Cay is a community of 134 homes in Kissimmee, Osceola County, built between 2022 and 2024 (median 2024.0), with a median living area of about 1,851 square feet. 29% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
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
Cypress CayCypress CayCypress CayCypress CayCypress CayCypress Cay
Cypress Cay
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 20 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.
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.
17% 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 (2026-10-23).
Cypress Cay Market Scorecard
Cypress Cay is currently a buyer-leaning market. About 18.0 months of supply, a median asking price of $341,500, and homes go under contract in about 170 days.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
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 contributors.
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
Recent Developments in Cypress Cay
Development, infrastructure, retail, and school activity affecting Cypress Cay, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- September 2026Development
Orange County commissioners approve Tuscana land use plan in Shingle Creek Basin on 4-3 vote
Commissioners voted 4-3 to approve the Tuscana land use application from Shingle Creek Co-Owners LLC and Geyer Development, reversing a unanimous rejection in May 2025. The plan includes more than 1,000 hotel rooms, about 4,000 apartments and commercial buildings, with conditions for a raised road, flood mitigation and wetland protection. The developer projects thousands of jobs at full build-out.
What it may mean for the marketThe approval could add substantial rental housing, hotel capacity and commercial space in the Shingle Creek area, while flood-mitigation conditions will shape how and when it is built. The site is about 5 miles north of Cypress Cay.
Source: Spectrum News 13 - September 2026Infrastructure
CFX holds public meetings on 14-mile toll road through part of Split Oak Forest
The Central Florida Expressway Authority held public meetings on Sept. 16 and 17 for a 14-mile road from State Road 417 near Boggy Creek Road in Orange County to Nova Road in Osceola County. CFX says portions could begin construction next year and that the road would ease traffic on Narcoossee Road. The agency faces a legal challenge from Orange County and is pursuing an eminent domain case.
What it may mean for the marketIf built, the road would add a new east-west route between Lake Nona and St. Cloud, changing commute options and access to east Orange and Osceola land. The project is about 17 miles east of Cypress Cay, elsewhere in Osceola County.
Source: Spectrum News 13 - August 2026Retail & Dining
Plans for Mattel indoor water park near Lake Buena Vista Factory Stores expand to 13 acres
Updated plans for the site off State Road 535 show a 95,000-square-foot indoor water park designed by Martin Aquatic, a separate 45,000-square-foot entertainment building and nearly 900 parking spaces. The tower height rises to as much as 100 feet and still needs Orange County approval. About 200 jobs are expected, and no opening date has been announced.
What it may mean for the marketThe project would add visitor attractions, dining and roughly 200 jobs near the State Road 535 corridor, with added traffic and parking demand nearby. The site is about 6 miles northwest of Cypress Cay.
Source: FOX 35 Orlando - August 2026Civic
St. Cloud council approves $6.7 million downtown apartment and parking garage agreement
The City Council unanimously approved an agreement with Atlantic Housing Partners for apartments and a parking garage next to City Hall. The Community Redevelopment Agency contributes $6.25 million and the city $460,000. The garage would hold 450 to 500 spaces, with 250 reserved for apartment residents.
What it may mean for the marketNew downtown rental housing and public parking would add residents and parking capacity to the St. Cloud core. The project is about 12 miles southeast of Cypress Cay, elsewhere in Osceola County.
Source: Spectrum News 13 - March 2026Development
Orlando approves the 380-acre Dowden Central Community Development District in Lake Nona
Orlando approved the Dowden Central Community Development District, a roughly 380-acre district in the Lake Nona area of southeast Orlando, in March 2026. The district provides the framework to build roads, drainage, utilities, and parks for future development phases.
What it may mean for the marketA new community development district lays the groundwork for large-scale growth in the Lake Nona area, a step that typically precedes new housing and commercial activity nearby. The site is about 12 miles east of Cypress Cay.
Source: ClickOrlando
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in the Orlando Metro.
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 housing stock is 134 homes built between 2022 and 2024, and 29% 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 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 4 factors (1.8). Basis: Recent Direction -13.7% year-over-year; Liquidity & Demand 18.0 months of supply; Owner Commitment 29% owner-occupied; Pricing Power 87.7% sale-to-list. Refreshed with each data update.
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.
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Recently off market in Cypress Cay
Homes in Cypress Cay 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. 1 on record.
- 4705 Sparkling Shell Avenue · off market
| Location | Kissimmee, Osceola County, FL · ZIP 34746 |
|---|---|
| Homes in the community | 134 (FL DOR 2025 assessment roll) |
| Years built | 2022–2024 (median 2024.0) |
| Typical living area | 1,851 sq ft (median) |
| Home types (current listings and sales) | townhouses 100% |
| Amenities listed by sellers | Playground, Pool, Dog Park, Park, Community Mailbox, Basketball Court |
| Sale prices, last 12 months | $320,000 median across 3 closed sales · $184 per sq ft · -13.7% vs the prior 12 months |
| Days on market (closed sales) | 125 median |
| For sale right now | 6 active, 1 pending · median asking $341,500 · 18.0 months of supply |
| Owner-occupied (homestead) share | 29% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Cypress Cay key facts,” movewithmomentum.com/neighborhoods/cypress-cay-kissimmee, data as of September 20, 2026.
Housing distress & ownership in Cypress Cay, 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 October 2026 through October 2026. Deemed reliable but not guaranteed.
Just listed in Cypress Cay
The newest homes for sale in Cypress Cay right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 4576 Sparkling Shell Avenue $339,000 · 3 bd · 2.5 ba · 1,699 sq ft · listed Jul 22, 2026 Courtesy of NORTHGROUP REAL ESTATE, INC
- 4581 Sparkling Shell Ave $325,000 · 3 bd · 2.5 ba · 1,782 sq ft · listed Jul 14, 2026 Courtesy of IMAGINATION REALTY, INC
- 2511 Bright Jewel Street $355,000 · 3 bd · 2.5 ba · 1,683 sq ft · listed May 5, 2026 Courtesy of MY REALTY GROUP, LLC.
- 2639 Buena View Road $344,000 · 3 bd · 2.5 ba · 1,699 sq ft · listed Apr 11, 2026 Courtesy of RESILIENT MIND REALTY GROUP
- 2609 Bright Jewel Street #2909 $369,000 · 3 bd · 2.5 ba · 1,699 sq ft · listed Jun 7, 2024 Courtesy of TALENT REALTY SOLUTIONS
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Cypress Cay Kissimmee Right Now (6)
All 6 active and pending Cypress Cay Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 4576 Sparkling Shell Avenue · $339,000 · 3 bd / 2.5 ba · listed Aug 18, 2026 · listed by Northgroup Real Estate, Inc
- 4581 Sparkling Shell Ave · $319,000 · 3 bd / 2.5 ba · listed Aug 12, 2026 · listed by Imagination Realty, Inc
- 2511 Bright Jewel Street · $355,000 · 3 bd / 2.5 ba · listed Jul 26, 2026 · listed by My Realty Group, Llc.
- 2639 Buena View Road · $344,000 · 3 bd / 2.5 ba · listed by Resilient Mind Realty Group
- 4617 Sparkling Shell Avenue · $275,000 · 3 bd / 2.5 ba · pending · listed by Mosaic Partners Group
- 2609 Bright Jewel Street #2909 · $369,000 · 3 bd / 2.5 ba · listed by Talent Realty Solutions
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Kissimmee guides & data
- Market data
- Cost of living
- Best neighborhoods (ranked by data)
- Best neighborhoods
- Flood zones
- Property taxes (Osceola County)
- Homestead exemption (Osceola County)
- Home insurance cost
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
Real estate agent in Kissimmee? Join Momentum in Kissimmee: 100% commission, one $12K cap.
Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Sparkling Shell Avenue (67 homes on record)
- Cypress Cay Way (21 homes on record)
- Sparkling Shell Avenue (5 homes on record)
- Cypress Cay Way (4 homes on record)
- Sparkling Shell Avenue (2 homes on record)
- Sparkling Shell Avenue (1 homes on record)
- Cypress Cay Way (1 homes on record)
What it really costs to own in Cypress Cay
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | Median $298/month across 9 MLS listings (most billed monthly; 2026-10-24). Dues cover what the documents say they cover; ask for the budget and reserve study. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Osceola County is $1,735/yr (2,188 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. Flood: of 9 listing addresses checked against the FEMA flood map, 100% sit outside the high-risk zone. Statewide, a Zone X flood policy runs about $500-$700/yr and a high-risk zone $1,200-$2,500/yr (FEMA Risk Rating 2.0 averages, not quotes). |
| Roof and age | Median build year 2022 across 9 listings. Newer roofs and current wind-mitigation features usually mean the lower end of insurance quotes. |
Email me new listings in Cypress Cay
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Cypress Cay
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Cypress Cay will answer, and the answer is published on this page for the next buyer.
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?
How many homes are in Cypress Cay?
What share of Cypress Cay is owner-occupied?
When were the homes in Cypress Cay built?
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?
Where is Cypress Cay, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 23, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 34746)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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.
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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:
More on Cypress Cay
- Home values · What homes in Cypress Cay actually sell for
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