4332 CHERRYWOOD STREET, WINTER HAVEN, FL, 33880
Active1 days on marketListed Sep 2, 2026MLS #L4964514
About this home
4332 CHERRYWOOD STREET
OVER $19,000 IN RECENT UPGRADES MEANS THE BIG-TICKET WORK HAS ALREADY BEEN DONE! This fully furnished Oakwood Estates home features a new roof (2023), plus new HVAC, electric water heater, rain gutters, and exterior porch tile (2024). Step inside to a bright, welcoming interior filled with natural light from double-pane windows. Luxury vinyl plank flooring flows throughout. The kitchen features stainless steel appliances, white cabinetry, wood-look countertops, and a newer sink. Built-in cabinetry adds charm and storage to the dining area, which opens to a spacious living room. Both bedrooms are generously sized, with a walk-in closet in the primary. A separate laundry room includes the washer and dryer. Enjoy additional living space in the Florida room and enclosed lanai, perfect for relaxing and enjoying the Florida lifestyle. Hurricane shutters, vinyl siding, and an updated electrical panel add even more value. Oakwood Estates is a gated, resident-owned 55+ community with two heated pools, two clubhouses, pickleball and tennis courts, shuffleboard, bocce ball, miniature golf, a fishing lake and pier, RV and boat storage, library, activities center, and an active social calendar. Major updates done, furnishings included, and ready for you to move in and enjoy!
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
1,150
Sqft
0.08 ac
Lot size
1983
Year built
One
Levels
$100
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.
$1,153 /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
$1,153/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
+3.5%
Days on market
1 vs 48 typical
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 33880 — neighborhood snapshot
Population
42,336
Median age
36.5
Median income
$56,803
Median home value
$200,900
Avg household
2.8
Households w/ children
5,516
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)
Median sold price, Winter Haven, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 50% below the WINTER HAVEN 33880 median. See the full Winter Haven market guide →
Paper trail
This home's history
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
Anealya Hammad
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 4332 CHERRYWOOD STREET — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 4332 CHERRYWOOD STREET — before you fall in love.
See it in person
Schedule a tour
Live availability from Anealya's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
4332 CHERRYWOOD STREET FAQs
What would the monthly payment be for 4332 CHERRYWOOD STREET?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $1,153/mo — principal and interest, the actual property-tax bill, the $171/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 4332 CHERRYWOOD STREET?+
The association fee works out to $171 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 4332 CHERRYWOOD STREET?+
The most recent tax bill on record (2025) was $1,124. 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 4332 CHERRYWOOD STREET?+
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 $115,000, this home is listed about 60% below the Winter Haven median of $285,000. The market section on this page shows how the area is trending.
Which schools are assigned to 4332 CHERRYWOOD STREET?+
Denison Middle School (middle), Winter Haven Senior High School (high), John Snively Elementary (elementary) — Polk County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Under the WINTER HAVEN 33880 market on paper
$115,000 is 50% below the WINTER HAVEN 33880 median of $229,900, and at $100/sqft it sits under the Winter Haven average of $172.
02Move-in furnished
The furniture conveys — a genuine head start for a second home or rental, and one less five-figure line item after closing.
03Fresh on the market
Only 1 day on market in a Winter Haven market that averages 48 — if it fits, move quickly.
Listing courtesy of KELLER WILLIAMS REALTY · Jared Weggeland. MLS #L4964514.
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.
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