Cypresswood-Oakgrove
Homes for Sale in Winter Haven, FL
All 793 homes for sale in WINTER HAVEN, FL · median $280,000 · 331 homes for sale in 33884 · Polk County homes for sale
True comps, carrying-cost math, and listings before the portals.
| Location | WINTER HAVEN, Polk County, FL · ZIP 33884 |
|---|---|
| Homes in the community | 53 (FL DOR 2025 assessment roll) |
| Years built | 2001–2006 (median 2004) |
| Typical living area | 2,308 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 70% |
| Zoned public schools | Polk County Public Schools (verify by address); Confirm zoned elementary, middle, and high; Magnet and choice options may apply |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “CYPRESSWOOD-OAKGROVE key facts,” movewithmomentum.com/neighborhoods/cypresswood-oakgrove, data as of August 2, 2026.
Nearby homes for sale
No active listings inside CYPRESSWOOD-OAKGROVE 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.
As of September 2026, the MLS records 4 closed sales in Cypresswood-Oakgrove in Winter Haven, FL since 2014, the most recent in September 2025. Across Winter Haven as a whole, 42 homes closed in the last 12 months at a median of $308,400, 65 median days on market, with 16 homes for sale today. At that median and Polk County's FY2025-26 rate of 16.19 mills, annual property tax runs about $4,990 ($4,320 with the full homestead exemption).
The market around Cypresswood-Oakgrove
Cypresswood-Oakgrove is a small community — 4 recorded sales on file, most recently in 2012 — 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-Oakgrove specifically. Momentum Research analysis of MLS records.
Schools
- 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-Oakgrove 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-Oakgrove address.
The Cypresswood-Oakgrove buying strategy.
If we were buying in Cypresswood-Oakgrove 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 Cypresswood-Oakgrove.
A closer look at the Cypresswood-Oakgrove market
The housing stock is 53 homes built between 2001 and 2006, and 70% 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-Oakgrove. The deal is won or lost on condition, the comps, and the renovation math.
HOA, CDD & Fees
- 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.
Tools for a Cypresswood-Oakgrove 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 Cypresswood-Oakgrove sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cypresswood-Oakgrove, 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-Oakgrove home worth?
Get a no-obligation home value based on real comparable sales in Cypresswood-Oakgrove, 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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Cypresswood Oak Grove Market Scorecard
Cypresswood Oak Grove is currently a thin data market. Limited supply, a median asking price of n/a.
Go deeper: true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, 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-Oakgrove?
What share of Cypresswood-Oakgrove is owner-occupied?
When were the homes in Cypresswood-Oakgrove built?
What schools serve Cypresswood-Oakgrove?
Who is the best real estate agent for Cypresswood-Oakgrove?
How do I find a top Winter Haven real estate agent who knows Cypresswood-Oakgrove?
Can Momentum Realty connect me with an agent for Cypresswood-Oakgrove?
Where is Cypresswood-Oakgrove, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: June 30, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 33884)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Schools | 2025-26 district assignments + FLDOE school grades; verify with the district |
| Historical depth | Closed-sale records back to 2014 (4 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.
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