Cypress Shadows
Homes for Sale in Kissimmee, FL
All 3,084 homes for sale in Kissimmee, FL · median $375,000 · 801 homes for sale in 34746 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Photo via Stellar MLS
Over the 12 months ending 2026-08-02, 3 recorded sales closed at a median of $290,000, $173 per square foot, a median 65 days on market, sellers accepting 91% of original asking (-16% versus the prior year). Homes listed or recently sold were built 2004–2005; 6 of 6 report an HOA (median $81/mo); none of the 6 geocoded homes sit in a FEMA special flood hazard zone (median elevation 78 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $4,420 ($3,820 with the full homestead exemption).
Last 30 days in Cypress Shadows: 1 new listing (median asking $340,000). As of October 17, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Cypress Shadows is a mid-2000s community in Kissimmee, with homes built between 2004 and 2016 and a median build year of 2005. At a median of roughly 2,200 square feet, the stock skews toward larger floor plans, and price here is driven far more by individual condition and updates than by any single benchmark. With no closings in the current window, there is no fresh sale price to anchor to, so pricing has to be worked deal by deal rather than off a recent comp.
For sellers, that thin recent activity means presentation and realistic pricing matter more than usual — you cannot lean on a hot comparable that closed last month. For buyers, it means room to negotiate on condition, since two homes of similar size can sit far apart on price depending on how much has been updated since the mid-2000s.
Cypress Shadows right now
🔴 Off the recent peak. The trailing-12-month median ($290K) is down 15.9% from the prior 12 months ($345K). With about 4 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 (3 and 4 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 18, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside CYPRESS SHADOWS right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Cypress Shadows market snapshot (as of August 2, 2026): the median sale price is about $290K ($173 per sq ft over the trailing 12 months of closed sales), and a median 65 days on market for closed sales. The trailing-12-month median is down 16% 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.
Cypress Shadows is a community of 197 homes in Kissimmee, Osceola County, built between 2004 and 2016 (median 2005), with a median living area of about 2,200 square feet. 66% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Cypress Shadows is a 186-home community in Osceola County built primarily in the mid-2000s, with generously sized floor plans around 2,200 square feet and a majority owner-occupied posture.
The setting & the homes.
Aerial and on-site photos of Cypress Shadows. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Cypress ShadowsPhotos from Stellar MLS listings in Cypress Shadows; content deemed reliable but not guaranteed.
Who Cypress Shadows is best for.
Best for
- Buyers seeking more square footage — around 2,200 on the median — in an established setting
- Long-term owner-occupants who value a stable, mostly homesteaded community
- Buyers comfortable budgeting for roof/HVAC/system updates on a roughly two-decade-old home
Probably not for
- Buyers who require new construction or the latest finishes out of the box
- Buyers who need a recent, comparable-backed sale price before committing
- Buyers wanting the lowest possible carrying costs of a smaller, newer home
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 ($290K) IS the median in the snapshot above, and the move from 2025 ($345K) IS the -15.9% one-year change.
Windows contain 0 to 15 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 2009 through 2026. Deemed reliable but not guaranteed.
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 (2026-10-18).
Cypress Shadows Market Scorecard
Cypress Shadows is currently a balanced market., and homes go under contract in about 1 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.
Homes For Sale Right Now in Cypress Shadows
Live MLS inventory for Cypress Shadows. 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 Shadows listings as of 2026-10-17, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2009 through 2026. Tap any home to ask about it.
Cypress Shadows 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.
The Cypress Shadows buying strategy.
If we were buying in Cypress Shadows 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.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
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 Shadows.
A condition-driven mid-2000s market
The homes here cluster tightly in age — the range runs 2004 to 2016, but the median build year is 2005, so most of the community is now roughly two decades old. That age is the single biggest variable in value: roofs, HVAC systems, and kitchens from the original build are reaching the point where they have either been replaced or are due. Expect a wide spread between a maintained, updated home and one that still wears its original finishes.
With about two-thirds of homes homesteaded, this reads as an owner-occupied community rather than an investor-churn one, which tends to translate into better-kept exteriors and less turnover pressure. The larger median footprint near 2,200 square feet gives buyers real room, but it also means higher carrying costs to maintain and cool — something to weigh against a smaller, newer home elsewhere in the area.
The location and the amenities are priced into every listing in Cypress Shadows. 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 Shadows 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 (4.1). Basis: Recent Direction -15.9% year-over-year; Owner Commitment 66% owner-occupied; Pricing Power 90.6% sale-to-list. Refreshed with each data update.
Why work with Momentum here
With no recent closings to anchor a price, Cypress Shadows rewards someone who knows how to read condition against a thin comp set. We price and negotiate off the details that actually move value here — roof and system age, updates since the mid-2000s, and how a home's 2,200-odd square feet is laid out — rather than off a headline number that may not exist yet.
Cypress Shadows in 15 seconds.
What it really costs to own in Cypress Shadows
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 $75/month across 160 MLS listings (most billed quarterly; 2026-10-15). 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. |
| Roof and age | Median build year 2005 across 6 listings. An original roof here would be about 21 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Cypress Shadows
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 Shadows
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Cypress Shadows will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $75/month (about $900/yr) · median of 160 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $75 per month ($900 a year) — the median AssociationFee across 160 MLS records, normalised to a monthly figure; most are billed quarterly. 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, 2026-10.
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 Shadows 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 Shadows sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cypress Shadows, 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 Shadows home worth?
Get a no-obligation home value based on real comparable sales in Cypress Shadows, 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 →
| Location | Kissimmee, Osceola County, FL · ZIP 34746 |
|---|---|
| Homes in the community | 197 (FL DOR 2025 assessment roll) |
| Years built | 2004–2016 (median 2005) |
| Typical living area | 2,200 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Basketball Court, Community Mailbox, Deed Restrictions, Park, Playground |
| Sale prices, last 12 months | $290,000 median across 3 closed sales · $173 per sq ft · -15.9% vs the prior 12 months |
| Days on market (closed sales) | 65 median |
| Owner-occupied (homestead) share | 66% |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2009 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Cypress Shadows key facts,” movewithmomentum.com/neighborhoods/cypress-shadows, data as of August 2, 2026.
Housing distress & ownership in CYPRESS SHADOWS, 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.
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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.
- Spring Blossom Drive (21 homes on record)
- Spring Blossom Drive (16 homes on record)
- Shadow Creek Drive (13 homes on record)
- Spring Blossom Drive (11 homes on record)
- Spring Blossom Drive (11 homes on record)
- Spring Blossom Drive (8 homes on record)
- Creeks Run Boulevard (8 homes on record)
- Creeks Run Boulevard (7 homes on record)
- Creeks Run Boulevard (6 homes on record)
- Spring Blossom Drive (5 homes on record)
- Spring Blossom Drive (5 homes on record)
- Shadow Creek Drive (5 homes on record)
Recent Developments in Cypress Shadows
Development, infrastructure, retail, and school activity affecting Cypress Shadows, 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 8 miles northwest of Cypress Shadows.
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 15 miles northeast of Cypress Shadows, 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 10 miles northwest of Cypress Shadows.
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 9 miles east of Cypress Shadows, 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 10 miles northeast of Cypress Shadows.
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 Northeast Florida.
Frequently Asked Questions
What is the median home price in Cypress Shadows?
How long do homes in Cypress Shadows take to sell?
How many homes are in Cypress Shadows?
What share of Cypress Shadows is owner-occupied?
When were the homes in Cypress Shadows built?
Do cash buyers compete in Cypress Shadows?
Who is the best real estate agent for Cypress Shadows?
How do I find a top Kissimmee real estate agent who knows Cypress Shadows?
Can Momentum Realty connect me with an agent for Cypress Shadows?
Where is Cypress Shadows, and what county is it in?
Should you buy in Cypress Shadows?
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: October 17, 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 (5 streets, ZIP 34746)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2009 (49 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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See how CYPRESS SHADOWS fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
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More on Cypress Shadows
- Home values · What homes in Cypress Shadows actually sell for