Cypress Lake
Homes for Sale in Kissimmee, FL

All 2,944 homes for sale in Kissimmee, FL · median $373,250 · 111 homes for sale in 34743 · Osceola County homes for sale

Community in Kissimmee · Osceola County · ZIP 34743
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Built fromLive Stellar MLS data21 years of closingsUpdated twice daily

As of October 2026, the MLS records 10 closed sales in Cypress Lake Ph One in Kissimmee, FL since 2005, the most recent in April 2025. Across Kissimmee as a whole, 2,523 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,265 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,910 ($5,310 with the full homestead exemption).

Part of Cypress Lake, Kissimmee, FL — see all Cypress Lake homes for sale (0 listings across 3 sections in the MLS).

Jon Brooks, founder of Momentum Realty
Jon's Current Read

Cypress Lake Ph One is a built-out pocket of 225 homes in Kissimmee, with construction running from 1994 to 2008 and a median build year of 1997. That age band is what actually drives price here: this is a condition-and-updates market, not a new-construction one. Two homes of the same square footage can trade well apart depending on roof age, HVAC, kitchens, and whether the systems have been touched since the original build.

With a median living area around 1,512 square feet, this is a modest-footprint community, and the homestead share sitting at 44% tells you a meaningful slice of these homes are non-owner-occupied. For a buyer, that means you should underwrite condition carefully and expect a wide spread. For a seller, presentation and updated systems are the lever — an honestly updated home separates itself from the pack quickly.

Nearby homes for sale

No active listings inside Cypress LakeHomes for Sale in Kissimmee, FL 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.

2329 WATER VIEW LOOP
$289K · 0.1 mi away
3 bd · 2.5 ba · 1,460 sqft
2329 WATER VIEW LOOP
Listed by FIGLOFT INC
2321 WATER VIEW LOOP
$265K · 0.1 mi away
3 bd · 2.5 ba · 1,460 sqft
2321 WATER VIEW LOOP
Listed by REMAX PREMIER PROPERTIES
2041 LACIE JO LANE
$340K · 0.1 mi away
3 bd · 2.5 ba · 1,807 sqft
2041 LACIE JO LANE
Listed by SOVERA REALTY GROUP, LLC
2039 CYPRESS BAY BOULEVARD
$299K · 0.1 mi away
3 bd · 2.5 ba · 1,382 sqft
2039 CYPRESS BAY BOULEVARD
Listed by SELLING TOWN REALTY LLC
2024 CYPRESS BAY BOULEVARD
$295K · 0.2 mi away
3 bd · 2.5 ba · 1,807 sqft
2024 CYPRESS BAY BOULEVARD
Listed by CHARLES RUTENBERG REALTY ORLANDO
2018 CYPRESS BAY BOULEVARD
$300K · 0.2 mi away
3 bd · 2.5 ba · 1,824 sqft
2018 CYPRESS BAY BOULEVARD
Listed by EXP REALTY LLC

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

The 60-Second Overview

A mature, fully established Kissimmee community of 225 homes built between 1994 and 2008, where the story is less about location amenities and more about how well each individual house has been maintained and updated over its life.

Stellar MLS sales records identify 54 homes in Cypress Lake that have changed hands since 2004, built between 1991 and 1998 (median 1995), with a median living area of about 1,177 sq ft and a typical 3-bedroom, 2-bath layout; 93% 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.

County records show 17 qualified sales in Cypress Lake across 2024–2025 (10 in 2024, 7 in 2025), median $285,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

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.

Best for

  • Buyers seeking a modestly sized, established home and willing to reward updated systems over square footage
  • Value-focused buyers ready to budget for roof, HVAC, or cosmetic updates on an older home
  • Investors comparing owner-occupied and rental-condition inventory in a stable, built-out area

Probably not for

  • Buyers wanting new construction or turnkey modern finishes with no work
  • Buyers needing a large-footprint home well above the roughly 1,512-square-foot median
  • Buyers who want to skip inspection and rely on list price to reflect true condition

The market around Cypress Lake

Cypress Lake is too small for its own price trend, so here is the market around it.

In ZIP 34743, 146 homes are on the market and 23% are under contract — a steady corner of Kissimmee.

Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).

In ZIP 34743 (Kissimmee), 352 homes closed in the last 12 months at a median of $348K ($239/sq ft), down 2.6% year over year, with a median 31 days on market. Right now 27 active and 6 pending listings put supply at about 4.5 months — a balanced market. See the live ZIP 34743 housing market and the Osceola County market.

ZIP and county figures describe the wider market, not Cypress Lake specifically. Momentum Research analysis of MLS records.

Cypress Lake Ph One by the numbers

From county property records and closed MLS sales for the Cypress Lake Ph One subdivision: 39 homes on record; built 1994–1998; typical size about 1,177 heated sq ft; 3 bedrooms is the median. Housing mix: townhome 92%, single-family 5%, condo 2%.

YearRecorded salesMedian price
20122$68,750
20131$99,000
20143$97,000
20161$128,000
20224$245,000
20251$285,000

Newest recorded sale: $285,000 on 2025-04-25.

Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.

If we were buying in Cypress Lake today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Lake.

Best Buy
Buyers comfortable evaluating an established home on its systems rather than chasing new construction.
Biggest Risk
Wide condition spread means two similar homes can be worth very different money.
Sweet Spot
A well-maintained home near the median footprint with recent roof and HVAC.
Avoid If
You want move-in-modern finishes without doing any updating yourself.

A condition-driven resale market

Because nearly every home here predates 2008 and the median dates to 1997, big-ticket components matter more than square footage on paper. Roofs, HVAC, water heaters, and windows are all at or past the point where original equipment has typically been replaced at least once. The homes that command the top of the range are the ones where that work is done and documented; the ones that sit are usually the ones asking today's price on yesterday's systems.

The 44% homestead share also shapes inventory. A little over half of these homes are not owner-occupied, which historically means a mix of maintenance philosophies — some meticulously kept, some run harder as rentals. That variance is exactly why a walk-through and a real inspection carry more weight here than any headline stat. There is value in this community, but it rewards buyers who look closely.

“

The location and the amenities are priced into every listing in Cypress Lake. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

In a market this condition-sensitive, the number that matters is not the list price — it is what the roof, systems, and finishes are actually worth today. We price and negotiate off the specific house in front of us, not a neighborhood average, and we will tell a seller when their updates justify pushing and a buyer when a bargain is really deferred maintenance in disguise.

Cypress Lake in 15 seconds.

Best forBuyers comfortable evaluating an established home on its systems rather than chasing new construction.
Biggest advantageA built-out community where updated homes stand out clearly from dated ones.
Biggest riskWide condition spread means two similar homes can be worth very different money.
Sweet spotA well-maintained home near the median footprint with recent roof and HVAC.
Avoid ifYou want move-in-modern finishes without doing any updating yourself.

HOA, CDD & Fees

A note on who we are: Momentum Realty is a real estate brokerage. We are not the Cypress Lake homeowners association, its management company or its developer, and we cannot help with dues, gate access, violations, amenity bookings or association documents. To reach the association, check your closing package, the recorded declaration at the county clerk, or search the association’s name at sunbiz.org for its registered agent. Call or message us to buy or sell a home in Cypress Lake.
In short
  • HOA status not on record. Verify any dues before you offer
  • Any club/amenity membership is billed separately

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Cypress Lake sales matched to your home.

What is your Cypress Lake home worth?

Get a no-obligation home value based on real comparable sales in Cypress Lake, 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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Real comps, not an automated estimate.
Buyers seeking a modestly sized, established home and willing to reward updated systems over square footageExcellent fit
Value-focused buyers ready to budget for roof, HVAC, or cosmetic updates on an older homeExcellent fit
Investors comparing owner-occupied and rental-condition inventory in a stable, built-out areaExcellent fit
Buyers wanting new construction or turnkey modern finishes with no workProbably not
Buyers needing a large-footprint home well above the roughly 1,512-square-foot medianProbably not
Buyers who want to skip inspection and rely on list price to reflect true conditionProbably not

Data sources & freshness

Under-contract sharesStellar MLS records, as of 2026-09-08
Historical depthClosed-sale records back to 2005 (10 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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Common questions about Cypress Lake

Where is Cypress Lake?

Cypress Lake is a community in Kissimmee, Osceola County, Florida, ZIP 34743.

How many homes are in Cypress Lake?

County property records list 39 homes in Cypress Lake, built between 1994 and 1998; the typical home is about 1,177 heated square feet.

What do homes in Cypress Lake sell for?

Cypress Lake has no MLS sales in the last 12 months. The most recent year with recorded sales on file is 2025 (1 sale, median $285,000). For context, ZIP 34743 has 146 homes on the market with 23% under contract.

Are there homes for sale in Cypress Lake right now?

No active listings inside Cypress Lake at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.

Does Cypress Lake have an HOA or CDD?

No HOA is on record for Cypress Lake in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.

Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.

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