Cypress Hammock
Homes for Sale in Kissimmee, FL
All 3,104 homes for sale in Kissimmee, FL · median $375,000 · 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 Hammock in Kissimmee, FL has 14 homes for sale, asking from $299,000 to $485,000 (median $409,995). Over the 12 months ending 2026-08-02, 8 recorded sales closed at a median of $411,500, $176 per square foot, a median 148 days on market, sellers accepting 85% of original asking (+2% versus the prior year). Homes listed or recently sold were built 2021 - 2024; 22 of 23 report an HOA (median $123/mo); 19 of the 23 geocoded homes sit in a FEMA special flood hazard zone (median elevation 65 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $6,270 ($5,670 with the full homestead exemption).
Last 30 days in Cypress Hammock: 2 new listings (median asking $389,500), 1 closed sale (median $340,000). As of October 24, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Homes For Sale Right Now in Cypress Hammock
Live MLS inventory for Cypress Hammock. 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 · 34 daysTop listing
Active · 322 days
Active · 34 days
Active · 72 days
Active · 105 days
Active · 253 days
Active · 120 days
Active · 138 days
Active · 141 days
Active · 72 days
Active · 117 days
Active · 179 days
Active · 5 daysActive and pending Cypress Hammock 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 Hammock right now
🟢 Buyer-leaning market. 13.2 months of supply and 15% 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: High (13 active and pending listings, 8 closed sales in 12 months).
🟡 Still climbing. The trailing-12-month median ($412K) is up 2.1% from the prior 12 months ($403K).Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Medium (8 and 24 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 Hammock market snapshot (as of August 2, 2026): the median sale price is about $412K ($176 per sq ft over the trailing 12 months of closed sales), a median 148 days on market for closed sales, and 13.2 months of supply, a buyer-leaning market. The trailing-12-month median is up 2% from the prior 12 months, computed from record-level Stellar MLS closed sales (8 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.
Flood zones in Cypress Hammock: of 19 listing addresses checked against the FEMA National Flood Hazard Layer, 100% are in an A-series high-risk zone where flood insurance is required with a federally backed mortgage. Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Kissimmee.
Cypress Hammock is a community of 500 homes in Kissimmee, Osceola County, built between 2021 and 2024 (median 2023.0), with a median living area of about 2,181 square feet. 56% 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 Hammock. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Cypress HammockCypress HammockCypress HammockCypress HammockCypress HammockCypress HammockCypress HammockCypress HammockPhotos from Stellar MLS listings in Cypress Hammock; content deemed reliable but not guaranteed.
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 ($412K) IS the median in the snapshot above, and the move from 2025 ($403K) IS the +2.1% one-year change.
Windows contain 0 to 73 sales each (8 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.
0% of homes for sale in Cypress Hammock 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 (2026-10-25).
CYPRESS HAMMOCK Market Scorecard
CYPRESS HAMMOCK is currently a strong buyer's market. About 18.7 months of supply, a median asking price of $409,995, and homes go under contract in about 117 days.
Typical home value in the 34746 ZIP is $357,258, about 6.7% 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.
Cypress Hammock 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 Hammock
- Playground · reported on 19 of 21 listings
- Pool · reported on 19 of 21 listings
- Clubhouse · reported on 10 of 21 listings
- Park · reported on 7 of 21 listings
- Community Mailbox · reported on 7 of 21 listings
- Irrigation-Reclaimed Water · reported on 5 of 21 listings
- Recreation Facilities · reported on 4 of 21 listings
- Trail(s) · reported on 3 of 21 listings
- Deed Restrictions · reported on 3 of 21 listings
- Maintenance · reported on 1 of 21 listings
- No Truck/RV/Motorcycle Parking · reported on 1 of 21 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
- Knights Point · Elementary
- Horizon Middle · Middle
- Poinciana High School · High
Zoned schools reflect the assignments reported on recent Cypress Hammock 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 Hammock address.
Shop the zone: Homes zoned for Poinciana High School
Recent Developments in Cypress Hammock
Development, infrastructure, retail, and school activity affecting Cypress Hammock, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- 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 site is about 6 miles northeast of Cypress Hammock.
Source: Spectrum News 13 - 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 site is about 5 miles southwest of Cypress Hammock.
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 5 miles northwest of Cypress Hammock.
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 Hammock buying strategy.
If we were buying in Cypress Hammock 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 Hammock.
A closer look at the Cypress Hammock market
At a median of $176 per square foot, Cypress Hammock 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 13.2 months of supply, a buyer-leaning market and the trailing-12-month median up 2% year over year. Homes that do trade take a median 148 days on market, useful leverage on any listing that has lingered.
The housing stock is 500 homes built between 2021 and 2024, and 56% 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 Hammock. 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 Hammock 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 (3.1). Basis: Recent Direction +2.1% year-over-year; Liquidity & Demand 13.2 months of supply; Owner Commitment 56% owner-occupied; Pricing Power 85.2% sale-to-list. Refreshed with each data update.
Tools for a Cypress Hammock 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 Hammock sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cypress Hammock, 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 Hammock home worth?
Get a no-obligation home value based on real comparable sales in Cypress Hammock, 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 HAMMOCK
Homes in CYPRESS HAMMOCK 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. 5 on record.
- 4943 Royal Point Avenue · off market
- 5014 Royal Point Avenue · off market
- 5016 Blue Hammock Court · off market
- 5179 Royal Point Avenue · off market
- 5346 Royal Point Avenue · off market
| Location | Kissimmee, Osceola County, FL · ZIP 34746 |
|---|---|
| Homes in the community | 500 (FL DOR 2025 assessment roll) |
| Years built | 2021–2024 (median 2023.0) |
| Typical living area | 2,181 sq ft (median) |
| Home types (current listings and sales) | single-family 65%, townhouses 35% |
| Amenities listed by sellers | Playground, Pool, Clubhouse, Community Mailbox, Irrigation-Reclaimed Water, Park |
| Sale prices, last 12 months | $411,500 median across 8 closed sales · $176 per sq ft · +2.1% vs the prior 12 months |
| Days on market (closed sales) | 148 median |
| For sale right now | 11 active, 2 pending · median asking $400,000 · 13.2 months of supply |
| Owner-occupied (homestead) share | 56% |
Data as of August 2, 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 Hammock key facts,” movewithmomentum.com/neighborhoods/cypress-hammock-kissimmee, data as of August 2, 2026.
Housing distress & ownership in CYPRESS HAMMOCK, 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 Hammock
The newest homes for sale in Cypress Hammock right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 1275 Wispy Cypress Drive $299,000 · 4 bd · 2.5 ba · 1,876 sq ft · listed Oct 17, 2026 Courtesy of KELLER WILLIAMS LEGACY REALTY
- 5317 Royal Point Avenue $485,000 · 4 bd · 3 ba · 2,178 sq ft · listed Sep 18, 2026 Courtesy of URBAN-O REAL ESTATE SOLUTIONS
- 5285 Royal Point Avenue $469,900 · 4 bd · 3 ba · 2,178 sq ft · listed Sep 18, 2026 Courtesy of QP HOMES REALTY LLC
- 5003 Royal Point Avenue $360,000 · 3 bd · 2 ba · 1,424 sq ft · listed Aug 11, 2026 Courtesy of THE LANDRUA GROUP REAL ESTATE INC
- 1466 Woodmont Boulevard $469,900 · 4 bd · 2.5 ba · 2,155 sq ft · listed Aug 11, 2026 Courtesy of REAL BROKER, LLC
- 5049 Blue Hammock Court $450,000 · 4 bd · 2.5 ba · 2,248 sq ft · listed Jul 9, 2026 Courtesy of KELLER WILLIAMS LEGACY REALTY
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Cypress Hammock Kissimmee Right Now (12)
All 12 active and pending Cypress Hammock Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 1275 Wispy Cypress Drive · $299,000 · 4 bd / 2.5 ba · listed Oct 18, 2026 · listed by Keller Williams Legacy Realty
- 5317 Royal Point Avenue · $485,000 · 4 bd / 3 ba · listed Sep 19, 2026 · listed by Urban-O Real Estate Solutions
- 5285 Royal Point Avenue · $469,900 · 4 bd / 3 ba · listed Sep 19, 2026 · listed by Qp Homes Realty Llc
- 5003 Royal Point Avenue · $360,000 · 3 bd / 2 ba · listed Sep 10, 2026 · listed by The Landrua Group Real Estate Inc
- 1254 Wispy Cypress Drive · $400,000 · 3 bd / 2.5 ba · listed Sep 10, 2026 · listed by Century 21 Next Level Realty
- 1259 Wispy Cypress Drive · $334,900 · 4 bd / 2.5 ba · listed Sep 4, 2026 · listed by Forteza Realty Llc
- 1466 Woodmont Boulevard · $469,900 · 4 bd / 2.5 ba · listed Sep 1, 2026 · listed by Real Broker, Llc
- 5049 Blue Hammock Court · $450,000 · 4 bd / 2.5 ba · listed Aug 28, 2026 · listed by Keller Williams Legacy Realty
- 1188 Woody Cypress Drive · $389,990 · 4 bd / 2.5 ba · listed by My Realty Group, Llc.
- 1255 Wispy Cypress Drive · $375,000 · 4 bd / 2.5 ba · listed by Keller Williams Heritage Realty
- 1286 Wispy Cypress Drive · $325,000 · 3 bd / 2.5 ba · listed by Axen Realty, Llc
- 5018 Royal Point Avenue · $419,990 · 4 bd / 2.5 ba · listed by Dream Finders Realty Group Corp
Recently sold in Cypress Hammock Kissimmee
- 5346 Royal Point Avenue · sold $340,000
- 4943 Royal Point Avenue · sold $450,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
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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
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Royal Point Avenue (63 homes on record)
- Woodmont Boulevard (16 homes on record)
- Royal Point Avenue (12 homes on record)
- Wispy Cypress Drive (12 homes on record)
- Woodmont Boulevard (10 homes on record)
- Royal Point Avenue (5 homes on record)
- Royal Point Avenue (1 homes on record)
- Wispy Cypress Drive (1 homes on record)
What it really costs to own in Cypress Hammock
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 $123/month across 22 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 19 listing addresses checked against the FEMA flood map, 0% sit outside the high-risk zone and 100% inside one, where flood insurance is required with a federally backed mortgage. 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 24 listings. Newer roofs and current wind-mitigation features usually mean the lower end of insurance quotes. |
Email me new listings in Cypress Hammock
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 Hammock
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Cypress Hammock 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 Hammock?
How long do homes in Cypress Hammock take to sell?
Is Cypress Hammock a buyer's or seller's market right now?
How many homes are in Cypress Hammock?
What share of Cypress Hammock is owner-occupied?
When were the homes in Cypress Hammock built?
Do cash buyers compete in Cypress Hammock?
Who is the best real estate agent for Cypress Hammock?
How do I find a top Kissimmee real estate agent who knows Cypress Hammock?
Can Momentum Realty connect me with an agent for Cypress Hammock?
Where is Cypress Hammock, and what county is it in?
Is Cypress Hammock a good place to live?
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 August 2, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (13 streets, ZIP 34746)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2021 (180 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?
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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 HAMMOCK fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Cypress Hammock
- Home values · What homes in Cypress Hammock actually sell for
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