Cypresswood
Meadows

Single-family, built about 1985 to 1993 · Polk County · ZIP 33884

A 1980s to early 1990s single-family enclave inside the Cypresswood Golf and Country Club community in southeast Winter Haven.

Golf community settingEstablished single-familyOptional club membership

Live Market Pulse

50/100
Momentum

Buyer-Leaning Market (limited data)

Cypresswood Meadows is one platted enclave inside the larger Cypresswood Golf and Country Club community, so the honest read is the enclave HOA, the separate optional country club membership, and the specific lot, not a townwide average. Confirm dues, club fees, and the exact lot per listing.

Free · No obligation

Unlock Off-Market Cypresswood Meadows

Listings before the portals, true comps, and the renovation and carrying-cost math, before you tour.

Built fromLive Stellar MLS data14 years of closingsLocal renovation analysisUpdated twice daily

LiveMarket PulseStellar MLS

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Median Price

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Supply

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Avg DOM

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Seller Leverage

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Median $/Sqft

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Jon's Current Read

"Cypresswood Meadows is an established single-family enclave inside the broader Cypresswood Golf and Country Club community in southeast Winter Haven, so the read is a mature-community read: homes built mostly in the late 1980s and early 1990s where the value drivers are the lot, the condition and updates of an older house, the enclave HOA, and the optional country club membership, not new construction. Listing guides describe homes ranging from roughly 988 to 2,343 square feet with monthly HOA fees that sources cite in a wide band, so the dues and what they cover have to be confirmed per address. The country club membership is generally optional and separate, because the club is semi-private and members are not required to live in the community, so the golf, pool, and tennis access is a choice with its own cost, not an automatic inclusion. Your leverage is reading the enclave HOA, the club fee structure, and the condition of an older home honestly before you price the golf-community address."

Jon Brooks, founder, Momentum Realty · Updated June 2026

The 60-Second Overview

Cypresswood Meadows is a single-family home subdivision inside the Cypresswood Golf and Country Club community in Winter Haven, Polk County, built roughly between 1985 and 1993 (Cypresswood Country Club neighborhood real estate guides, 2026). It sits in southeast Winter Haven near Cypress Gardens Boulevard, in a mature, tree-lined setting organized around the golf course and clubhouse.

Listing guides describe homes ranging from about 988 to 2,343 square feet, a mix of modest and larger single-family floor plans typical of the era, with some lots fronting or near the golf course (homesbymarco and Watson Realty community pages, 2026). Because these are 1980s and early 1990s homes, condition, roof and system age, and interior updates vary widely by address, so each house has to be read on its own.

The broader Cypresswood Golf and Country Club is built around an 18-hole semi-private course that opened in 1973 and was designed by Ron Garl, with a clubhouse, pool, tennis, and practice facilities (Cypresswood Golf and Country Club, golf course directories, 2026). Membership is generally optional and separate, since the club is semi-private and does not require members to live in the community, so confirm what the enclave HOA covers versus what a country club membership costs.

The pitch is an established golf-community address at a Polk County price point, with US Highway 27, Legoland Florida, and the Orlando attractions corridor within reach. The work is the diligence: confirm the enclave HOA dues and inclusions, the optional club fees, and the condition of an older home before you buy the setting.

Quick Match

Who Cypresswood Meadows is best for.

Best for

Buyers who want an established single-family home in a golf-community setting
Buyers comfortable with 1980s and early 1990s homes that may need updates
Golfers who value optional access to a semi-private course and clubhouse
Buyers who will confirm the HOA dues, club fees, and home condition per address

Probably not for

Buyers who want brand-new construction with current finishes
Anyone unwilling to verify HOA dues, club fees, and roof and system age
Buyers who assume golf and amenity access is automatically included
Buyers who want a maintenance-free condo or villa rather than a yard

Market Pulse

How Cypresswood Meadows is performing right now

50/100
momentum

Buyer-Leaning Market (limited data)

Seller's marketBalancedBuyer's market

0Months of supplytight

24Median days on marketdays

0 : 0Under contract vs for salestrong demand

0Sold in last 12 monthsliquidity

+127%Median price since 2012appreciation

+0%Asking vs recent sold $/sqftroom to negotiate

Tight supply and strong demand favor sellers here. Homes still take about two months to sell, though, and with asking prices running above recent sales per square foot, a prepared buyer has room on anything overpriced. Reading each home against the real comps, not the headline trend, is where the edge is.

Live from Stellar MLS, as of June 30, 2026. Refreshed twice daily. Months of supply, days on market, and the contract-to-listing ratio are computed from current Cypresswood Meadows listings and the trailing twelve months of closed sales.

Where prices are going$850K2026 YTD

Median sale price by year. Tap a label to compare Cypresswood Country Club or Winter Haven. The 1-year price change is the median sold price over the most recent year versus the prior year, the same measure most listing sites and local Realtor reports use. It reflects the mix of homes that sold, not the change in any single home's value, which is why median price per square foot is shown alongside it to adjust for home size. In thinly traded neighborhoods, where a sale or two can swing the median, we lead with the mix-resistant price-per-square-foot trend instead.

Price per square foot$3072026 YTD

Median $/sqft by year. 2026 is year to date.

Supply and demand now0 : 0active : pending

For sale0

Pending0

Sold 12mo0

Active and pending listings now vs homes sold in the last 12 months.

8.6A- score

Momentum intelligence

Momentum buy score

Our proprietary read on how a home in Cypresswood Meadows buys, holds, and resells. See the five factors.

Interactive Map

Cypresswood Meadows on the map.

Every active, pending, and recently sold home, plotted. Toggle the layers, color the dots by status or lot type, and tap a home for the details.

Listing locations from Stellar MLS; lot type inferred from listing descriptions. Destination pins are approximate. Map data © OpenStreetMap, tiles © CARTO. Flood, school, and commute overlays are on the roadmap.

The Club & Membership

15-Second Take

Optional, member-owned club, separate from the POA
~$30M renovation underway, 2026 to 2028
18-hole course, clubhouse, pool, 10 clay courts
Strong value vs Ponte Vedra clubs
Budget the membership separately from the home

Cypresswood Meadows is an established single-family enclave inside the Cypresswood Golf and Country Club community, so the lifestyle is mature golf-community living rather than new construction. The broader community offers an 18-hole semi-private golf course, a clubhouse with dining, a pool, tennis, and practice facilities, accessed through an optional membership, along with gated entry and tree-lined streets. The enclave HOA, the optional club fees, and the condition of an older home vary, so confirm the current dues, what requires a membership, and what each home includes before you buy.

Nearby & Commute

How far is everything?

The takeaway

Cypresswood Meadows trades new construction for an established golf-community address, with Cypress Gardens Boulevard, Legoland, and US 27 close and the Orlando corridor within reach.

Drive times from the community. They are approximate and vary with traffic and your exact routine.

Cypress Gardens Boulevard retail~5 to 10 min · shops and dining

Legoland Florida~10 to 15 min · to the southwest

Downtown Winter Haven and the Chain of Lakes~10 to 15 min · lakes and dining

US Highway 27~10 to 15 min · north to south corridor

Posner Park and I-4~20 to 30 min · shopping and the interstate

Orlando attractions corridor~45 to 60 min · to the northeast

Tampa~60 to 75 min · to the west

Distances and times are approximate and vary with traffic and the specific home. Confirm your real commute at your real departure time.

Nearby Communities

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

CGCypresswood Golf& Country ClubWinter Haven, FL · adjacent CGCypresswoodOak GroveWinter Haven, FL · adjacent CHCypresswoodPatio Homes in Winter Haven, FLWinter Haven, FL · adjacent CYCypresswoodPlantationsWinter Haven, FL · adjacent CVCypresswoodTennis VillasWinter Haven, FL · adjacent CHCypresswood Homes for Sale in Winter Haven, FLWinter Haven, FL · adjacent CCCypresswoodPalma Ceia Homes for Sale in Winter Haven, FLWinter Haven, FL · 0.4 mi CHCypresswoodPlantation Homes for Sale in Winter Haven, FLWinter Haven, FL · 0.5 mi WHWhisperingTrails Homes for Sale in Winter Haven, FLWinter Haven, FL · 0.8 mi

Browse all Florida neighborhood guides →

Carrying cost · the no-CDD edge

No CDD bond means thousands less per year than newer master plans.

Typical CDD community~$2,500/yr

Cypresswood Meadows (no CDD)$0/yr

Roughly $25,000 saved over 10 years in carrying cost, before resale.

Illustrative. NE Florida CDD assessments commonly run $1,500-$3,500+/yr and vary by community; verify per property.

Schools

15-Second Take

Polk County Public Schools
Verify the zoned schools by address
Magnet and choice options may be available
Confirm current ratings before relying on them
Private and parochial options nearby

Cypresswood Meadows is served by Polk County Public Schools. Assignment is by address and can change, so confirm the exact zoned elementary, middle, and high schools for any specific home, plus any magnet or choice options. Treat published ratings as a starting point, not the full story.

Public

Polk County Public Schools (verify by address)

Verifyrating

By address

Confirm zoned elementary, middle, and high

Verifyrating

Choice

Magnet and choice options may apply

Verifyrating

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

The takeaway

What is actually shaping value at Cypresswood Meadows: the health and direction of the Cypresswood Golf and Country Club, Winter Haven growth along the US 27 and Cypress Gardens Boulevard corridor, and the realities of insuring and maintaining older Florida homes. Each item is an evergreen observation to confirm locally.

Recent Developments in Cypresswood Meadows

Development Intelligence

Our read on what is being built around Cypresswood Meadows, scored for direction, significance, and how close the effect lands. The full sourced timeline follows below.

Net OutlookBullishAn established golf-community address and steady Winter Haven demand support values, with the watch items being the long-term health of the semi-private club, older-home insurance and repair costs, and the wide HOA and club fee picture that has to be confirmed per address.

Health of the Cypresswood Golf and Country Club

Ongoing

NeutralMajor impact

SignificanceRadius: Community

The community is organized around a semi-private club, so the club operations, membership health, and amenity upkeep are central to the address and worth confirming.

Winter Haven growth along US 27 and Cypress Gardens Boulevard

Ongoing

BullishNotable impact

SignificanceRadius: Area

Continued retail and residential growth along the corridor supports demand and convenience for southeast Winter Haven communities.

Older Florida home insurance and roof costs

Ongoing

NeutralNotable impact

SignificanceRadius: Community

On late-1980s to early-1990s homes, roof age and system condition drive insurance and carrying cost, making the home inspection central diligence.

Optional country club membership structure

Ongoing

NeutralNotable impact

SignificanceRadius: Community

Because the club is semi-private and membership is generally optional, golf and amenity access is a separate cost to confirm rather than an automatic inclusion.

Legoland Florida and the attractions corridor

Ongoing

BullishMinor impact

SignificanceRadius: Area

Proximity to Legoland Florida and the Orlando attractions corridor supports the area profile and can aid demand and rentability.

Mature, established enclave character

Ongoing

BullishNotable impact

SignificanceRadius: Community

Tree-lined streets and an established golf-community setting differentiate this enclave from newer cookie-cutter subdivisions in the area.

Direction, significance, and effect-radius ratings are Momentum's proprietary, qualitative read of the sourced items below, not investment advice or a prediction for any specific home.

Development, infrastructure, retail, and school activity affecting Cypresswood Meadows, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated June 2026.

Showing the latest, scroll for all updates ↓

January 1973
Community
Cypresswood golf course opens, anchoring the community
The 18-hole Cypresswood Golf and Country Club course, designed by Ron Garl, opened in 1973 as a semi-private layout and became the anchor of the broader Cypresswood community in southeast Winter Haven. Why it matters: The golf course is the founding amenity of the community, so the long-term health of the semi-private club remains central to the value of homes in enclaves like Cypresswood Meadows. Source

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.

The Strategy

The Cypresswood Meadows buying strategy.

If we were buying in Cypresswood Meadows, this is the order of operations we would run, and the one we run for our clients.

Confirm the enclave HOA dues and what they cover. Sources cite a wide monthly range across the Cypresswood community, so verify the exact Cypresswood Meadows dues and inclusions from the listing and the association.

Ask whether a country club membership is required or optional. The club is semi-private and members are not required to live here, so confirm the membership tiers and costs separately from the HOA.

Read the roof, HVAC, and system age. On a late-1980s to early-1990s home, the roof and major systems drive insurance and carrying cost, so get the ages and condition for the specific house.

Check the lot and golf-course exposure. Lots fronting the course or with mature landscaping can carry a premium, so confirm the exact lot, setbacks, and any golf-cart access.

Cross-shop the wider community, such as Cypresswood Country Club, if a different enclave, villa, or price point fits better.

The Quick Decision

Best Buy

An updated single-family home on a good lot with a clear HOA and club read

Biggest Risk

Underbudgeting an older roof, systems, and the optional club fees

Best Lot

A well-landscaped or golf-adjacent lot with documented setbacks

Smart Timing

Confirm HOA dues, club fees, and home condition before you offer

Deep-Dive Intelligence

The full read, only if you want it.

The takeaway

On mobile, tap any heading below to open it. This is the home by home, lot by lot, club and renovation detail, organized so you can jump straight to what matters to you.

Community Details at a Glance

Cypresswood Meadows Homes For Sale

What your money buys in Cypresswood Meadows.

The takeaway

Three honest price bands. Condition and lot, not the square footage alone, decide where a home lands.

Here are the broad resale bands in Cypresswood Meadows today. The right home is the one matched to your budget and the renovation math, so seeing fitting listings early is the edge.

The Entry Home

A smaller, more original late-1980s home, the affordable way into the community, where condition and updates drive value.

Lowest entry

The Core Home

A mid-size updated single-family home on a solid lot, the heart of the enclave resale market.

Most inventory

The Top

A larger, well-updated home on a premium or golf-adjacent lot, the homes that hold value best in the enclave.

Strongest resale

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

See Off-Market & Private Listings

What Your Money Buys

What ~$900K buys here.

Three realistic price bands. Where a home lands comes down to condition and lot, not square footage alone.

The Entry Home

A smaller, more original late-1980s home, the affordable way into the community, where condition and updates drive value.

The Core Home

A mid-size updated single-family home on a solid lot, the heart of the enclave resale market.

The Top

A larger, well-updated home on a premium or golf-adjacent lot, the homes that hold value best in the enclave.

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

Operator Intelligence

Renovation & Resale Intelligence

The factors that actually move value in Cypresswood Meadows, condition, lot, and the renovation math, read from current listings and recent sales.

15-Second Take

Renovation math decides the deal
Golf and lake lots resell strongest
Roof and HVAC age drive the insurance quote
Interior lots are where buyers overpay

Proprietary Data

The renovation premium.

Renovated-listing inventory in Cypresswood Meadows is too thin right now to compute a reliable renovation premium. We read condition home by home against real comps before you offer.

Lot Value

The lot premium.

On golf, lake, and preserve frontage, the homesite is the part of your money the market gives back at resale. The house can be renovated; the lot cannot, so premium lots hold their value better than interior ones. How much more they command varies by frontage, view, and condition, which is why we read it home by home against real comparable sales rather than a single headline figure.

Operator Note

Most buyers overpay on interior lots in the back half of the community. A sharp renovation can distract you, but the weaker resale position follows the lot, not the finishes. We read the homesite before the kitchen.

Resale Strength Scorecard

How well Cypresswood Meadows holds value.

Our read on the factors that protect resale here, and the one to manage.

Home ageBuilt about 1985 to 1993, expect updates

Roof and systemsConfirm roof, HVAC, and plumbing age per home

HOA and club costsVerify dues and optional club fees per address

Location and amenitiesEstablished golf community near Cypress Gardens Blvd

Lot and exposureVaries by lot, golf-adjacent can carry a premium

Momentum analysis based on the no-CDD structure, central location, built-out lot scarcity, the funded club plan, and the all-resale 1990s housing stock. Not a guarantee of future value.

Operator Note

The strongest value pocket is usually a renovated golf or lake home priced just under the next tier up. Buyers chasing the single biggest estate often pay estate prices for what is really a renovation project.

5 Mistakes Buyers Make in Cypresswood Meadows

15-Second Take

Calling the listing agent (who works for the seller)
Misjudging the renovation budget
Overpaying for an interior lot
Ignoring the optional club cost
Skipping the roof, HVAC, and systems check

In an all-resale, seven-figure, renovation-driven market, the same five mistakes cost buyers the most. Every one is avoidable with the right preparation before you tour.

Calling the listing agent

The agent on the sign works for the seller. In a market where condition swings price by hundreds of thousands, negotiating against that agent with no one in your corner is the costliest move of all.

Misjudging the renovation math

A dated home looks like a deal until you price the roof, HVAC, pool, and full modernization honestly. Underbudget the reno and the bargain becomes the expensive house.

Overpaying for an interior lot

Golf frontage, lakefront, and preserve lots carry real, durable premiums. Pay an estate price for an interior lot and you are buying the weakest version of the value.

Ignoring the club decision

The club is optional and separate, so two similar homes can cost very differently to own. Buyers who do not price the membership they will actually use misread their real monthly number.

Skipping the systems check

A 1990s home means 1990s-era systems unless updated. Roof age, HVAC age, pool equipment, and prior renovations drive both price and insurability, and a thorough inspection matters more here than in a new build.

“

Cypresswood Meadows is one enclave inside a golf community, not a townwide average. The deal is won or lost on the lot, the older home condition, the enclave HOA, and the optional club membership.

Jon Brooks · Founder, Momentum Realty

Momentum Intelligence

Momentum Buy Score.

Our proprietary 0 to 10 read across the five factors that decide how a home here buys, holds, and resells.

7.2B · Buy Score

Resale Strength7.1/10

Renovation Risk5.5/10

Location Efficiency7.4/10

Long-Term Defensibility7.0/10

Carrying Cost Advantage6.4/10

Momentum Intelligence Scores are our proprietary, qualitative assessment based on the analysis on this page, on a 0 to 10 scale. They are a framework for comparing communities, not a guarantee of future value or advice on a specific home.

Momentum Housing Intelligence

Why our read on Cypresswood Meadows is different.

Most pages on this community are an automated estimate wrapped in stock copy. This one is built from the live Stellar MLS feed, fourteen years of closed sales, and a renovation-by-renovation read of what actually moves value here, lot by lot. No Zestimate, no guesswork.

Live Stellar MLS feed14 years of closed salesRenovation-premium analysisLot-by-lot, no automated estimates

Jon Brooks, founder of Momentum Realty. A housing economist with a background in real estate investment banking at Deutsche Bank and consulting at Ernst & Young, who has built and analyzed Northeast Florida real estate from the ground up.

About the analyst · Our methodology

Which Lots & Views Hold Value Best

Proprietary Data · Lot Value Map

Where the value actually sits. Each home is shaded by its price per square foot (a value read, not just a price) and ringed by lot type, so you can see at a glance which pockets carry a real, durable premium and where a renovation play makes sense.

Value ($/sqft)

$261 value$401 premium

GolfLake / waterPreserveInterior

Fill = price per square foot; ring = lot type, inferred from listing descriptions. Sold homes are shown by realized $/sqft (lot type not always recorded). Asking and recent-sold figures from Stellar MLS; for orientation, not an appraisal.

15-Second Take

In an established enclave, the lot and updates set value
Golf-adjacent and well-landscaped lots can carry a premium
Confirm the exact lot, setbacks, and golf-cart access
Read the roof and systems before the finishes
Confirm the HOA dues and optional club fees per address

In a mature single-family enclave, the part of your money the market protects is the lot, the golf-course exposure, and the quality of any updates on an older home. A well-landscaped or golf-adjacent lot with an updated house holds value better than an original home on a plain interior lot. The kitchen and baths can be renovated; the lot, the exposure, and the location inside the community cannot. Read the roof and system age, the HOA dues, and the optional club costs first, then price the condition of the home against them.

The 15-Second Verdict

Cypresswood Meadows in 15 seconds.

Best forBuyers who want an established single-family home in a golf-community setting.

Biggest advantageA mature golf-community address at a Polk County price point.

Biggest riskOlder roofs and systems plus optional club fees that can move the carrying cost.

Sweet spotAn updated home on a good lot with a clear HOA and club read.

Avoid ifYou want brand-new construction or a maintenance-free condo or villa.

HOA Dues, the Club Fee & What Is Optional

15-Second Take

Confirm the exact Cypresswood Meadows HOA dues per address
Ask what the dues cover versus what needs a club membership
Verify whether a country club membership is required or optional
Budget the roof and systems on an older home separately
Confirm gated access details and any golf-cart rules

Cypresswood Meadows carries an enclave HOA, and listing sources cite a wide monthly range across the broader Cypresswood community, so the figure has to be confirmed for this specific enclave and address. The dues typically support common-area upkeep, gated access, and shared neighborhood items, but the separate country club membership for golf, pool, and tennis is generally optional and priced on its own. Confirm the current Cypresswood Meadows dues, what they include, and the club fee structure from the listing and the association.

The enclave HOA generally covers common-area maintenance, gated or guarded entry, and shared neighborhood items, while the country club amenities such as golf, the clubhouse, pool, and tennis are accessed through a separate optional membership because the club is semi-private. Owners maintain their own homes and yards. Verify exactly what the HOA fee covers, what requires a club membership, and what each owner is responsible for before you buy.

Run Your Numbers

Tools for a Cypresswood Meadows 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 Meadows.Save Our HomesProject your homestead tax cap over time.

The takeaway

Selling here is won on condition and view, not the Zestimate. The right number comes from closed comps matched to your renovation level and lot.

Selling in Cypresswood Meadows

Price to the lot, the updates, and the real HOA and club read, not an area average.

Selling here means pricing to your specific home and lot and to the real HOA and optional club picture, not a Cypresswood-wide estimate. The lot, the golf-course exposure, the age of the roof and systems, and the quality of any updates are what set your number in a mature golf community.

Momentum listings (YTD)

97.98%

Sold-to-list ratio across our market for our agents, sellers keeping more of their price.

Market average (YTD)

96.73%

The broader metro average sold-to-list ratio over the same period.

Momentum days on market

64 days

Median days on market for our listings, faster sales mean less carrying cost and stronger leverage.

Market days on market

72 days

The broader metro median over the same period.

Sold-to-list and days-on-market figures reflect Momentum Realty listings versus our market average, year to date. Your home's result depends on pricing, condition, lot, view, and preparation.

In Cypresswood Meadows, condition and view decide your number

Because buyers here are weighing your home against renovated comps and cross-shopping Cypresswood Country Club, a home priced to the community average instead of its true condition and view either leaves money on the table or sits. A renovated kitchen, newer roof and HVAC, and a golf or lake view all deserve to show up in your price, and a buyer pool reading renovation math needs to be shown why your home is worth it. We build that case with real comps and a pricing strategy for the current market.

What is your Cypresswood Meadows home worth?

Get a no-obligation home value based on real comparable sales in Cypresswood Meadows matched to your condition, lot, and view, 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 Meadows on the map →
Or get your Cypresswood Meadows home value & selling guide →

Real comps, not a Zestimate.

Price History: What Homes Here Have Actually Sold For

Median sale prices in Cypresswood Meadows year by year since 2012, from closed MLS sales. A long track record beats a single estimate, showing what this community has really done through rate cycles rather than what a model predicts.

The real cost & risk here

Before the list price, the Florida math the portals skip. These are Polk County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.

$1,609/mo

Polk County typical true cost to own

$110/mo

Polk County typical home insurance

No CDD

No community development district bond

Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Polk 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.

Cypresswood Meadows Market Scorecard

Strong seller's market

Cypresswood Meadows is currently a strong seller's market. About 1.8 months of supply, a median asking price of $1,019,500, and homes go under contract in about 58 days.

1.8

Months supply

$1,019,500

Median list

$847,500

Median sold

$313

Per sqft

Days on mkt

6/8/41

Active/Pend/Sold

Typical home value in the 32224 ZIP is $456,759, about 13.7% above the Florida norm (Zillow Home Value Index).

Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.

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

Frequently Asked Questions

Where is Cypresswood Meadows?

It is a single-family enclave inside the Cypresswood Golf and Country Club community in southeast Winter Haven, Polk County, ZIP 33884, near Cypress Gardens Boulevard.

When were the homes built?

Listing guides describe Cypresswood Meadows as built roughly between 1985 and 1993 (Cypresswood Country Club neighborhood real estate guides, 2026), making these established late-1980s to early-1990s homes.

Is Cypresswood Meadows a 55+ community?

No. Cypresswood Meadows is described as a standard single-family enclave. The broader Cypresswood area includes a separate 55+ gated section, so confirm the specific enclave and any age rules per address.

Is this part of the larger Cypresswood community?

Yes. Cypresswood Meadows is one platted enclave within the Cypresswood Golf and Country Club community, which also includes other single-family enclaves, villas, and patio homes. Confirm which enclave a listing is in.

Do I have to join the country club?

Generally no. The club is semi-private and members are not required to live in the community, so a country club membership for golf, pool, and tennis is typically optional and priced separately. Confirm the current rules and tiers.

What does the HOA fee cover?

The enclave HOA generally covers common-area upkeep, gated access, and shared neighborhood items, while golf and clubhouse amenities are accessed through a separate optional membership. Confirm the exact inclusions and dues per address.

How much are the HOA dues?

Listing sources cite a wide monthly range across the broader Cypresswood community, so the exact Cypresswood Meadows figure has to be confirmed for the specific enclave and address from the listing and the association.

What size are the homes?

Listing guides cite homes ranging from roughly 988 to 2,343 square feet, a mix of modest and larger single-family floor plans. Confirm the exact size, bedroom count, and lot for any specific home.

Tell me about the golf course.

The Cypresswood Golf and Country Club course is an 18-hole semi-private layout that opened in 1973 and was designed by Ron Garl, with a clubhouse, pool, tennis, and practice facilities (golf course directories, 2026). Access is through an optional membership.

Is the community gated?

Community guides describe gated and guarded access for the Cypresswood community. Confirm the current entry arrangement, any guard hours, and golf-cart rules for the specific enclave and address.

What should I check on an older home here?

On a late-1980s to early-1990s home, confirm the roof age, the HVAC and plumbing condition, any updates, and insurance costs, since these drive the real carrying cost more than the list price.

What schools serve Cypresswood Meadows?

It is served by Polk County Public Schools, with assignment by address that can change. Confirm the exact zoned elementary, middle, and high schools for the specific home, and note that magnet and choice options may apply.

What is nearby?

Cypress Gardens Boulevard, US Highway 27, Legoland Florida, and the Winter Haven Chain of Lakes are close, with the Orlando attractions corridor within reach. Confirm real drive times for your routine.

Is Cypresswood Meadows a good investment?

An established golf-community address at a Polk County price point supports demand, but these are older homes, so condition, the HOA, and the optional club costs drive the outcome. This is not a guarantee of future value; read the documents and the home.

Who is the best real estate agent for Cypresswood Meadows?

The best agent for Cypresswood Meadows is one who actively works Winter Haven and knows the community's pricing, HOA and CDD details, 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 Meadows.

How do I find a top Winter Haven real estate agent who knows Cypresswood Meadows?

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 Meadows and the wider Winter Haven area.

Can Momentum Realty connect me with an agent for Cypresswood Meadows?

Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Cypresswood Meadows purchase or sale - no call center and no pressure.

The Verdict

Should you buy in Cypresswood Meadows?

An honest fit check. We will tell you when it is not your community.

Buyers who want an established single-family home in a golf-community settingExcellent fit

Buyers comfortable with 1980s and early 1990s homes that may need updatesExcellent fit

Golfers who value optional access to a semi-private course and clubhouseExcellent fit

Buyers who will confirm the HOA dues, club fees, and home conditionExcellent fit

Buyers who want a mature, tree-lined setting at a Polk County price pointExcellent fit

Buyers who want brand-new construction with current finishesProbably not

Anyone unwilling to verify HOA dues, club fees, and roof and system ageProbably not

Buyers who assume golf and amenity access is automatically includedProbably not

Buyers who want a maintenance-free condo or villa rather than a yardProbably not

Buyers unwilling to budget for older-home repairs and updatesProbably not

Get the inside read on Cypresswood Meadows

Whether you are buying a renovation project, comparing the lots and views, weighing the optional club, or selling your Cypresswood Meadows home, tell us what you need. Every inquiry comes straight to us. We represent you, not the seller, and what your agent is paid is negotiable and set in a written buyer agreement up front. No obligation, no spam, no high-pressure follow-up.

You are all set.

A Momentum Realty Cypresswood Meadows specialist will reach out personally, usually the same day.

Thinking about hiring an agent here? How to find the best real estate agent in Cypresswood Meadows - what to look for, questions to ask, and your local expert.

Cypresswood Meadows median home price history from 2012 to 2026, chart by Momentum Realty — Median sale price in Cypresswood Meadows, Florida by year (2012 to 2026). Source: Momentum Realty.

Photography on this page is sourced from active and recently sold MLS listings in this community and remains the property of the listing brokerage and/or photographer. Listings courtesy of Stellar MLS as distributed by MLS GRID. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing; deemed reliable but not guaranteed by MLS GRID.

CypresswoodMeadows

The 60-Second Overview

Who Cypresswood Meadows is best for.

Best for

Probably not for

How Cypresswood Meadows is performing right now

Cypresswood Meadows on the map.

The Club & Membership

How far is everything?

Nearby Communities

Schools

Polk County Public Schools (verify by address)

Confirm zoned elementary, middle, and high

Magnet and choice options may apply

Recent Developments in Cypresswood Meadows

Health of the Cypresswood Golf and Country Club

Winter Haven growth along US 27 and Cypress Gardens Boulevard

Older Florida home insurance and roof costs

Optional country club membership structure

Legoland Florida and the attractions corridor

Mature, established enclave character

Cypresswood golf course opens, anchoring the community

The Cypresswood Meadows buying strategy.

The full read, only if you want it.

What your money buys in Cypresswood Meadows.

What ~$900K buys here.

Renovation & Resale Intelligence

The renovation premium.

The lot premium.

How well Cypresswood Meadows holds value.

5 Mistakes Buyers Make in Cypresswood Meadows

Calling the listing agent

Misjudging the renovation math

Overpaying for an interior lot

Ignoring the club decision

Skipping the systems check

Momentum Buy Score.

Why our read on Cypresswood Meadows is different.

Which Lots & Views Hold Value Best

Cypresswood Meadows in 15 seconds.

HOA Dues, the Club Fee & What Is Optional

Tools for a Cypresswood Meadows buy.

Price to the lot, the updates, and the real HOA and club read, not an area average.

In Cypresswood Meadows, condition and view decide your number

What is your Cypresswood Meadows home worth?

Price History: What Homes Here Have Actually Sold For

The real cost & risk here

Cypresswood Meadows Market Scorecard

Frequently Asked Questions

Should you buy in Cypresswood Meadows?

Get the inside read on Cypresswood Meadows

You are all set.

Need to sell fast in Polk County?

You just read the data. Now see what your home is worth.

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