Cypresswood
Plantation Homes for Sale in Winter Haven, FL

Single-family enclave · Polk County · ZIP 33884

A 115-home single-family enclave with its own Plantations HOA inside the gated Cypresswood golf community in Winter Haven, the residential read for buyers who want a home behind the gate.

Gated golf communitySingle-family enclaveOwn Plantations HOA

Live Market Pulse

50/100
Momentum

Buyer-Leaning Market (limited data)

This is one named single-family enclave inside a larger gated golf community, so the honest read is the layered dues, the Plantations sub-HOA plus the master community fee, what each covers, and the condition of the specific home, not a townwide average. Confirm every line per home and per the current association documents.

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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

0mo

Supply

91days

Avg DOM

Soft

Seller Leverage

n/a

Median $/Sqft

n/a

1-Yr Price Change

0now

Distress

Jon's Current Read

"Cypresswood Plantation is one named enclave inside the gated Cypresswood Golf and Country Club community in Winter Haven, so the read is a sub-community read: a cluster of about 115 single-family homes that sit under both a Plantations sub-HOA and the broader Cypresswood Community Association, where the value drivers are the layered dues, what each layer covers, the amenity and golf picture behind the gate, and the condition and outlook of the specific home, not a community-wide average. The Plantations enclave runs along Plantation Road and Plantation Way and backs several golf holes, so a home with a green outlook reads differently from an interior lot. Most of the Cypresswood housing stock dates to the 1980s onward, so the diligence is age-appropriate: read the roof, the HVAC, the plumbing, and any updates per home, and confirm what the sub-HOA maintains versus what the owner carries. The gate, the 18-hole Ron Garl golf course, the pool, the tennis and pickleball courts, and the clubhouse are the draw, but they also mean recurring fees and the reserve picture of a master association, so read the current budgets and reserve study before you buy the lifestyle. Your leverage is reading the two dues layers and the home condition honestly before the amenities sell you."

Jon Brooks, founder, Momentum Realty · Updated June 2026

The 60-Second Overview

Cypresswood Plantation is a single-family enclave inside the gated Cypresswood Golf and Country Club community in Winter Haven, Polk County (Cypresswood Community Association, 2026). It has its own named Plantations HOA, one of several sub-associations under the broader Cypresswood Community Association, with the association reporting about 115 homes on streets including Plantation Road, Plantation Way, Beauchamp Court, and Post Oak Court.

The Plantations HOA page notes the enclave is adjacent to golf course holes three through eight, so many homes sit near the course (Cypresswood Community Association, 2026). The wider Cypresswood community is described by its association as an established master-planned community of roughly 1,063 developed homes and homesites, with patio homes, villas, estate homes, and condominiums, and Plantation is the single-family product within that mix.

Because this is a sub-community inside a master association, the money is made or lost on the layered dues and the home, not on the address. The drivers are the Plantations sub-HOA assessment, the separate Cypresswood Community Association fee, what each layer maintains and insures, the amenity and golf operations behind the gate, and the condition and outlook of the specific home, all of which have to be read from the current association documents.

The pitch is a gated, country-club lifestyle: a staffed entrance, an 18-hole championship golf course, a swimming pool, tennis and pickleball courts, a wellness center, and a clubhouse with a restaurant and lounge, all off Cypress Gardens Boulevard near US 27 in south Winter Haven. The work is the diligence: read both dues layers, confirm what is maintained, and check the age-related condition of the home before you buy the amenities.

Quick Match

Who Cypresswood Plantation is best for.

Best for

Buyers who want a single-family home behind a gate
Golfers who want to live on or near an 18-hole course
Lock-and-leave buyers, year-round or seasonal, who value amenities
Buyers who will read both the sub-HOA and the master community dues

Probably not for

Buyers who want a large private lot with no association rules
Anyone unwilling to verify the two dues layers and what each covers
Buyers who want brand-new construction with the latest finishes
Buyers who do not want gate procedures or community restrictions

Market Pulse

How Cypresswood Plantation is performing right now

50/100
momentum

Buyer-Leaning Market (limited data)

Seller's marketBalancedBuyer's market

0Months of supplytight

91Median days on marketdays

0 : 1Under 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 26, 2026. Refreshed twice daily. Months of supply, days on market, and the contract-to-listing ratio are computed from current Cypresswood Plantation 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 Fairway Patio Homes 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 now1 : 0active : pending

For sale1

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 Plantation buys, holds, and resells. See the five factors.

Homes For Sale Right Now in Cypresswood Plantation

Live MLS inventory for Cypresswood Plantation. 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.

2935 Plantation Road home for sale in Cypresswood Plantation

Active · 91 daysTop listing

$588,900

4 bd · 3.5 ba · 2,724 sqft · built 1983

2935 Plantation Road, WINTER HAVEN, 33884

Strong resaleReno opportunityBest value

Listed by LBJ REALTY AND ASSOCIATES LLC

Active and pending Cypresswood Plantation listings as of 2026-06-26, priced high to low. Listings courtesy of Stellar MLS as distributed by MLS GRID.. Tap any home to ask about it.

Interactive Map

Cypresswood Plantation 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 Plantation is a single-family enclave inside a gated golf community rather than a standalone neighborhood, so the lifestyle is country-club living behind the gate. The wider Cypresswood Golf and Country Club community offers a staffed entrance, an 18-hole championship golf course, a junior Olympic sized swimming pool, lighted tennis and pickleball courts, a wellness center, and a clubhouse with a restaurant and lounge, all off Cypress Gardens Boulevard near US 27 in south Winter Haven. Amenities, golf membership terms, pet rules, and what each dues layer covers vary, so confirm the current rules and inclusions with the associations before you buy.

Nearby & Commute

How far is everything?

The takeaway

Cypresswood Plantation trades a large private lot for a gated golf lifestyle, with Cypress Gardens Boulevard, Legoland, and the Chain of Lakes close and the interstate a manageable drive.

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

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

Legoland Florida~10 to 15 min · theme park

Winter Haven Chain of Lakes~10 to 15 min · lakes and boating

Downtown Winter Haven~10 to 15 min · to the north

US 27 corridor~5 to 10 min · regional route

Interstate 4~25 to 35 min · to Tampa or Orlando

Orlando attractions~45 to 60 min · to the north

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 CypresswoodPlantation Homes for Sale in Winter Haven, FL with Momentum Realty’s local guides.

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 Plantation (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 Plantation 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)

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By address

Confirm zoned elementary, middle, and high

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Choice

Magnet and choice options may apply

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

The takeaway

What is actually shaping value at Cypresswood Plantation: the recent renovation of the community golf course, the layered association dues and reserves, and the steady appeal of a gated golf community in south Winter Haven. Each item is sourced or dated.

Recent Developments in Cypresswood Plantation

Development Intelligence

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

Net OutlookBullishA renovated golf course and an established gated community support demand, with the watch items being the layered dues and reserve picture of the master association and the age-related condition of the 1980s-era housing stock.