9566 BOLERO ROAD, WINTER GARDEN, FL, 34787
Active1 days on marketListed Aug 17, 2026MLS #O6434084
About this home
9566 BOLERO ROAD
Welcome to this stunning 5-bedroom, 3.5-bathroom, 3,910 sq. ft. home built in 2021, ideally situated on a quiet cul-de-sac with a 3-car garage, oversized fully fenced yard, and beautiful pond views. This spacious home features a desirable first-floor primary suite, two-story foyer, and a versatile upstairs loft. The gourmet kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinets with crown molding, upgraded stainless-steel appliances, vent hood, large island with quartz countertops, upgraded tile backsplash, pendant lighting, walk-in pantry, and a convenient butler's pantry for additional storage. The kitchen overlooks the family room and pond, with sliding doors leading to a large covered patio and extended paver lanai. The spacious first-floor primary suite offers a large walk-in closet and luxurious primary bathroom with dual vanities, large shower, and garden tub. Upstairs, enjoy a generous loft with pond views, along with four additional bedrooms. Bedrooms 2 and 3 share a full bathroom, while Bedrooms 4 and 5 feature a convenient Jack-and-Jill bathroom. Additional upgrades include walnut wood-plank tile throughout the main living areas, upgraded cabinetry, designer lighting, upgraded ceiling fans, custom accent walls, gutters, landscape lighting, and a fully fenced yard. The laundry room includes washer and dryer hookups. Located in the highly desirable Waterleigh community, residents enjoy an extensive collection of amenities, including three resort-style pools, two clubhouses with fitness centers, walking trails, sand volleyball, dog park, fishing and observation pier, tennis, pickleball, playgrounds, and more. HOA lawn maintenance is included, allowing you to enjoy the community without the hassle of yard care. Conveniently located near Disney, shopping, dining, SR 429, I-4, and SR 417
Facts & features
The home at a glance
5
Bedrooms
3.5
Bathrooms
3,910
Sqft
0.18 ac
Lot size
3
Garage
2021
Year built
Two
Levels
$1
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Principal and interest plus estimated taxes and insurance. Run your own numbers below.
$198 /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
$198/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Estimates only — taxes at 1.1%/yr and typical insurance; 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.
$/sqft vs Winter Garden actives
$1 vs $259
Days on market
1 vs 40 typical
Where $1/sqft sits among the 400 Winter Garden actives
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 Hickory Hut
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
Hickory Hut — neighborhood snapshot
Population
5,306
Median age
38
Median income
$152,813
Median home value
$545,824
Avg household
3
Households w/ children
664
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Garden market
$585K → $620K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
196 of 400
Winter Garden actives have cut their price
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 99% below the WINTER GARDEN 34787 median. See the full Winter Garden market guide →
Paper trail
This home's history
Reality check
What actually sold near 9566 BOLERO ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jul ’26$975,000
9549 BOLERO ROAD · same community
5 bd · 3.5 ba · 3,910 sqft · $249/sqft · 207 DOM
Sold · Nov ’25$720,000
9422 JAYWOOD ROAD · same community
5 bd · 3.5 ba · 3,299 sqft · $218/sqft · 7 DOM
Sold · Nov ’25$795,000
9406 BOLERO ROAD · same community
5 bd · 3.5 ba · 3,299 sqft · $241/sqft · 3 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
Ashton Harris
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 9566 BOLERO ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 9566 BOLERO ROAD — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Ashton's phone and CRM.
Straight answers
9566 BOLERO ROAD FAQs
What would the monthly payment be for 9566 BOLERO ROAD?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $198/mo — principal and interest, estimated property taxes 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.
Are pets allowed at 9566 BOLERO ROAD?+
The listing reports pets: Cats OK, Dogs OK. 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 Garden?+
At $5,200, this home is listed about 99% below the Winter Garden median of $575,000. The market section on this page shows how the area is trending.
Which schools are assigned to 9566 BOLERO ROAD?+
Water Spring Elementary (elementary), Horizon High School (high), Water Spring Middle School (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Under the WINTER GARDEN 34787 market on paper
$5,200 is 99% below the WINTER GARDEN 34787 median of $525,000, and at $1/sqft it sits under the Winter Garden average of $277.
02Fresh on the market
Only 1 day on market in a Winter Garden market that averages 40 — if it fits, move quickly.
03Strong assigned schools
Water Spring Elementary, Horizon High School, Water Spring Middle School — Horizon High School rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of LEGENDS REALTY · Tina Lopez. MLS #O6434084.
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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