300 GREENFIELD ROAD, WINTER HAVEN, FL, 33884
Active1 days on marketListed Aug 14, 2026MLS #P4939591
About this home
300 GREENFIELD ROAD
ON THE GOLF COURSE IN THE BEAUTIFUL & GATED COMMUNITY OF CYPRESSWOOD GOLF & COUNTRY CLUB!!! Recently remodeled, open, spacious & ready to move in! Enjoy the Cypresswood Country Club lifestyle, including an active clubhouse, junior Olympic size pool, pickle ball courts, tennis, golf and a great restaurant with bar! When you're not enjoying all of the amenities, take a walk or ride your bike on the quiet, tree-lined streets throughout the community! This is a one-of-a-kind, two-story classic home on an extra-large lot. No rear neighbors, just Florida nature and golf in your backyard! Great place for socializing, family gathering and just lots of relaxing! You can park a dozen cars in your driveway and park up to 6 cars in your garage! The oversized garages come complete with a "golf cart" garage in the rear of the home. Freshly remodeled by Bill Reed Construction, the updates include a freshly painted & neutral color scheme and luxury vinyl flooring throughout. You'll enjoy the golf-course views in the updated kitchen with granite tops and GE appliances. The open & bright kitchen nook area has sliding glass doors, and the family room is adjacent as well as a spacious dining room with lots of windows to enjoy! There is a separate living room with glass sliding doors to the oversized screened lanai and features a brick wood-burning fireplace creating a cozy area with lots of "flex" space. Room for all with 4 bedrooms and the primary suite boasts a walk-in closet, built-ins, dual sinks and a modern barn door. Three of the bedrooms are on the second floor. Mature landscaping and shade trees make perfect areas for enjoying the outdoor beauty and watching golf. Cypresswood is just minutes to Highway 27, great shopping, medical and the new Publix. Right in the heart of Central Florida with a "Chain of Lakes" for boating, fishing and a great "foodie" scene in the charming downtown district. This property has so much for your family to enjoy!!! Call today to schedule your private tour!
Facts & features
The home at a glance
4
Bedrooms
2.5
Bathrooms
2,350
Sqft
0.48 ac
Lot size
6
Garage
1975
Year built
Two
Levels
$181
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$3,565 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$3,565/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+26.6%
$/sqft vs CYPRESSWOOD
$181 vs $174
Days on market
1 vs 49 typical
Where $181/sqft sits among the 6 homes for sale in CYPRESSWOOD
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Winter Haven
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Haven. See the full Winter Haven guide →
WINTER HAVEN 33884 — neighborhood snapshot
Population
36,395
Median age
45.3
Median income
$70,516
Median home value
$269,400
Avg household
2.58
Households w/ children
3,777
For the school run
Polk County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Haven market
$283K → $280K
Winter Haven median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
3 of 6
CYPRESSWOOD have cut their price
Median sold price, Winter Haven, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 50% above the WINTER HAVEN 33884 median. See the full Winter Haven market guide →
Paper trail
This home's history
Reality check
What actually sold near 300 GREENFIELD ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Dec ’25$175,000
241 GREENFIELD ROAD · same community
2 bd · 2 ba · 2,394 sqft · $73/sqft · 25 DOM
Sold · Dec ’25$420,000
340 GREENFIELD ROAD · same community
4 bd · 2.5 ba · 2,460 sqft · $171/sqft · 2 DOM
Sold · Mar ’26$455,000
3155 BEAUCHAMP COURT · same community
3 bd · 2 ba · 2,103 sqft · $216/sqft · 25 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Chad Creech
President, Commercial and Development Services · CENTURY 21 Edge
Tours, negotiation, and every question about 300 GREENFIELD ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 300 GREENFIELD ROAD — before you fall in love.
See it in person
Schedule a tour
Live availability from Chad's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
300 GREENFIELD ROAD FAQs
What would the monthly payment be for 300 GREENFIELD ROAD?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,565/mo — principal and interest, the actual property-tax bill, the $152/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 300 GREENFIELD ROAD?+
The association fee works out to $152 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 300 GREENFIELD ROAD?+
The most recent tax bill on record (2025) was $6,763. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 300 GREENFIELD ROAD?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Haven?+
At $425,000, this home is listed about 49% above the Winter Haven median of $284,995. The market section on this page shows how the area is trending.
Which schools are assigned to 300 GREENFIELD ROAD?+
Elbert Elementary School (elementary), Winter Haven Senior High School (high), Denison Middle School (middle) — Polk County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of THE K TEAM REAL ESTATE SERVICES LLC · Cathy Kluytenaar. MLS #P4939591.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
Never miss a listing
New Winter Haven homes, in your inbox
Like 300 GREENFIELD ROAD but not quite? A daily digest of every new listing in Winter Haven — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Chad to ping you on any price or status change →