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CYPRESSWOOD MDWS in WINTER HAVEN

CYPRESSWOOD MDWS
Homes for Sale in WINTER HAVEN, FL

Community in WINTER HAVEN · Polk County · ZIP 33884
120 homesBuilt 1975–1993
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True comps, carrying-cost math, and listings before the portals.

Built fromLive Stellar MLS data5 years of closingsFL DOR public recordsUpdated twice daily
Live · CYPRESSWOOD MDWS Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Tempo
0 · 0
For sale · pending
live counts, refreshed twice daily
2
Sold · last 12 mo
10-yr average: about 1 a year
Ownership and context
71%
Owner-occupied · CYPRESSWOOD MDWS
85 of 120 parcels homesteaded (FL DOR 2025)
29%
Non-owner-occupied · CYPRESSWOOD MDWS
incl. 6% trust or LLC-held · 8% out-of-state
120
Homes in the community
120 residential parcels (FL DOR 2025)
Track record · 5 years of records
Est. 1975
Community established
homes built 1975-1993, median 1981 (FL DOR 2025)
0
Failed listings · 2025
peaked at 1 in 2024
1.7%/yr
Turnover rate
about 2 of 120 homes trade a year
The Area Market

The market around CYPRESSWOOD MDWS

CYPRESSWOOD MDWS is a small community — 2 recorded sales on file, most recently in 2025 — too few for its own price trend. Here is the market around it.

In ZIP 33884, 457 homes are on the market and 25% are under contract — a steady corner of WINTER HAVEN.

Across Polk County, 5,189 homes are active and 1,757 pending (25% under contract).

Homes here are single family residence.

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

Housing distress & ownership in CYPRESSWOOD MDWS, WINTER HAVEN

Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.

Active inventory in distress
0.0%
0 of 31 listings

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 August 2026 through August 2026. Deemed reliable but not guaranteed.

Schools

In short
  • Polk County Public Schools
  • Verify the zoned schools by address
  • Magnet and choice options may be available
  • Polk County Public Schools (verify by address) · Public
  • Confirm zoned elementary, middle, and high · By address
  • Magnet and choice options may apply · Choice

Zoned schools reflect the assignments reported on recent CYPRESSWOOD MDWS listings and can change; always confirm with Polk County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any CYPRESSWOOD MDWS address.

The Strategy

The CYPRESSWOOD MDWS buying strategy.

If we were buying in CYPRESSWOOD MDWS 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 CYPRESSWOOD MDWS.

The Deep Dive

A closer look at the CYPRESSWOOD MDWS market

The housing stock is 120 homes built between 1975 and 1993, and 71% 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 CYPRESSWOOD MDWS. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

HOA, CDD & Fees

In short
  • Mandatory HOA - confirm current dues
  • 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.

Run Your Numbers

Tools for a CYPRESSWOOD MDWS buy.

Free calculators to pressure-test the real cost before you tour.

Mortgage paymentPrincipal, interest, taxes, and insurance on a specific price.Property taxPolk County millage and the homestead picture.Rent vs buyThe breakeven on owning in CYPRESSWOOD MDWS.Save Our HomesProject your homestead tax cap over time.
The takeaway

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

Selling in CYPRESSWOOD MDWS

Price it to the comps and condition, not an automated estimate.

If you are thinking about selling in CYPRESSWOOD MDWS, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.

What is your CYPRESSWOOD MDWS home worth?

Get a no-obligation home value based on real comparable sales in CYPRESSWOOD MDWS, 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 homes for sale in CYPRESSWOOD MDWS on the map →

Real comps, not an automated estimate.

Cypresswood Meadows Market Scorecard

Thin data

Cypresswood Meadows is currently a thin data market. Limited supply, a median asking price of n/a.

n/a
Months supply
n/a
Median list
n/a
Median sold
n/a
Per sqft
n/a
Days on mkt
0/0/0
Active/Pend/Sold

Go deeper: true cost calculator · affordability calculator.

Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.

Frequently Asked Questions

How many homes are in CYPRESSWOOD MDWS?
The Florida DOR 2025 assessment roll shows 120 homes in CYPRESSWOOD MDWS (public records).
What share of CYPRESSWOOD MDWS is owner-occupied?
71% of CYPRESSWOOD MDWS parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in CYPRESSWOOD MDWS built?
Homes in CYPRESSWOOD MDWS were built between 1975 and 1993, with a median year built of 1981.0 (FL DOR 2025 roll).
What schools serve CYPRESSWOOD MDWS?
CYPRESSWOOD MDWS is served by Polk County Public Schools, typically Polk County Public Schools (verify by address) and Confirm zoned elementary, middle, and high. Confirm the exact zoning by address with the district.
Who is the best real estate agent for CYPRESSWOOD MDWS?
The best agent for CYPRESSWOOD MDWS is one who actively works WINTER HAVEN and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for CYPRESSWOOD MDWS.
How do I find a top WINTER HAVEN real estate agent who knows CYPRESSWOOD MDWS?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows CYPRESSWOOD MDWS and the wider WINTER HAVEN area.
Can Momentum Realty connect me with an agent for CYPRESSWOOD MDWS?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your CYPRESSWOOD MDWS purchase or sale - no call center and no pressure.

Nearby Communities

Explore more neighborhoods near CYPRESSWOOD MDWS with Momentum Realty’s local guides.

Cypresswood Plantations Winter HavenWINTER HAVEN, FL · 0.0 miCypresswood Tennis VlsWINTER HAVEN, FL · 0.0 miCypresswood Golf Country Club Winter HavenWINTER HAVEN, FL · 0.0 miCypresswood Winter HavenWINTER HAVEN, FL · 0.0 miCypresswood Patio HomesWINTER HAVEN, FL · 0.0 miCypresswood OakgroveWINTER HAVEN, FL · 0.0 miCPCypresswood Palma CeiaWINTER HAVEN, FL · 0.4 miCPCypresswood PlantationWINTER HAVEN, FL · 0.5 mi

Browse all Florida neighborhood guides →

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: June 30, 2026)
Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (2 streets, ZIP 33884))
Under-contract sharesStellar MLS records, as of 2026-08-01
Schools2025-26 district assignments + FLDOE school grades; verify with the district
Historical depthClosed-sale records back to 2021 (7 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 your area comps.

Looking to buy here? Search homes for sale →

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