4063 ROLLING OAKS DRIVE, WINTER HAVEN, FL, 33880
Active0 days on marketListed Aug 10, 2026MLS #S5155389
About this home
4063 ROLLING OAKS DRIVE
Welcome to 4063 Rolling Oaks in Winter Haven, located in Oakwood Estates, a desirable co-op 55+ community. This well-maintained 2 bedroom, 2 bathroom home offers a spacious and versatile floor plan featuring a bonus room and a Florida room, providing plenty of space for relaxing, entertaining, hobbies or a home office. Laminate flooring flows throughout the main living areas and bedrooms, while the Florida room features tile flooring. The dining room includes a built-in buffet with display cabinets and additional storage, creating the perfect space for showcasing your favorite pieces and hosting family and friends. The kitchen offers a convenient closet pantry for added storage, and both bedrooms feature generous walk-in closets. Exterior features include window awnings and an attached carport. A BRAND NEW ROOF was put on (08/2026). Oakwood Estates offers an affordable Florida lifestyle with low HOA fees that include water and trash service. Residents can also enjoy many amenities of this lakefront community including; two clubhouses, two swimming pools, an activity center with a pool table, tennis & pickleball courts, a mini golf course and a lake with fishing dock. Don’t miss this opportunity to own a home in a welcoming community conveniently located near shopping, dining, and all the great amenities and attractions Winter Haven is known for.
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
1,320
Sqft
0.08 ac
Lot size
1983
Year built
Three Or More
Levels
$87
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.
$1,092 /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
$1,092/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
+18%
Days on market
0 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 →
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 60% below the Winter Haven 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
Donna Layton
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 4063 ROLLING OAKS DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 4063 ROLLING OAKS DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Donna's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
4063 ROLLING OAKS DRIVE FAQs
What would the monthly payment be for 4063 ROLLING OAKS DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $1,092/mo — principal and interest, the actual property-tax bill, the $163/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 4063 ROLLING OAKS DRIVE?+
The association fee works out to $163 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 4063 ROLLING OAKS DRIVE?+
The most recent tax bill on record (2025) was $492. 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 4063 ROLLING OAKS DRIVE?+
The listing reports pets: Cats OK, Number Limit. 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 $114,995, 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.
Listing courtesy of RE/MAX HERITAGE PROFESSIONALS · Patricia De Graaff, Llc. MLS #S5155389.
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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