9566 BOLERO ROAD
WINTER GARDEN, FL 34787
About this home
Welcome to 9566 Bolero Rd, where luxury, space, and location come together in one of Central Florida’s most desirable and rapidly growing communities—Winter Garden. Situated on a premium 60-foot lot with beautiful pond views, this impressive North Haven model offers 5 bedrooms, 3.5 baths, a first-floor primary suite, spacious loft, and oversized fenced yard, all tucked away on a quiet cul-de-sac. Step inside through the dramatic two-story foyer and discover a bright, modern floor plan designed for both everyday living and entertaining. The gourmet kitchen features 42” cabinetry with crown molding, upgraded stainless-steel appliances, a vent hood, generous workspace, and an open layout overlooking the family room and picturesque pond beyond. Extend your living outdoors to the spacious backyard featuring a pergola, fenced yard, and tranquil water views—the perfect setting for morning coffee, entertaining, or relaxing at the end of the day. The first-floor primary suite offers privacy and convenience with a spacious walk-in closet and ensuite bath featuring dual vanities, a large walk-in shower, and garden tub. Upstairs, a generous loft provides flexible space for a media room, playroom, home office, or second living area. Bedrooms 2 and 3 share a full bath, while Bedrooms 4 and 5 are connected by a convenient Jack-and-Jill bath. The laundry room is also pre-plumbed for a utility sink. Enjoy the benefits of a resort-style, maintenance-free community while being surrounded by everything that makes Winter Garden such an exceptional place to call home. The area continues to flourish with new restaurants, shopping, grocery stores, entertainment, and everyday conveniences, while still offering the charm and lifestyle Winter Garden is known for. Enjoy easy access to Walt Disney World, Disney Springs, Publix, SR-429, I-4, and SR-417, connecting you to Orlando’s world-class attractions, employment centers, and entertainment. Whether you're enjoying peaceful pond views from your backyard, exploring nearby dining and shopping, or heading out for a day at Disney, 9566 Bolero Rd offers the space, lifestyle, and location you've been looking for. Welcome home!
Facts & features
Interior
- Bedrooms
- 5
- Bathrooms
- 4
- Living area
- 3,910 sqft
- Heating
- Central
- Cooling
- Central Air
- Flooring
- Carpet, Ceramic Tile
- Stories
- 2
- Features
- High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Smart Home, Solid Surface Counters…
- Appliances
- Cooktop, Dishwasher, Disposal, Freezer, Ice Maker, Microwave…
Exterior & lot
- Lot size
- 7,961 sqft (0.18 ac)
- Roof
- Tile
- Construction
- Block
- Exterior
- Rain Gutters
Parking
- Garage
- 2 spaces
Financial
- HOA dues
- $277 / monthly
- Annual tax
- $14,422 (2025)
- Price / sqft
- $249/sqft
Utilities
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- Cable Connected, Electricity Connected, Sewer Connected, Sprinkler Recycled, Water Connected
Property
- Property type
- Single Family
- Year built
- 2021
- Subdivision
- WATERLEIGH PH 3A
- County
- Orange
Assigned schools
- Elementary
- Water Spring Elementary
- Middle
- Water Spring Middle
- High
- Horizon High School
Listing
- Status
- Active
- Days on market
- Today
- MLS #
- MFR802099317
- Source
- Stellar MLS
Listed by Lisette Maestre · ERA GRIZZARD REAL ESTATE
Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.
Sample estimate — not an appraisal
Based on 25 comparable sales within 1 mile of WINTER GARDEN, FL, this home is priced in line with RENA ValiQ.
Reference only. Estimates blend public sale comps, neighbourhood trend and the listing’s own metrics. Final price moves on diligence, terms and timing — RENA is your second read, not your agent.
Estimate your monthly cost
PITI + HOA- Principal & interest
- $4,930/mo
- Property tax
- $1,202/mo
- Home insurance
- $0/mo
- HOA dues
- $277/mo
Opens at 20% down over 30 years at 6.5%, the same assumptions as the answers below. Property tax is this listing's own bill; insurance is left out until you enter a quote, because Florida premiums turn on roof age, elevation and carrier. Every field is editable.
Ask about this property
Answered from this listing’s own figures and the sales around it.
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Aug 6, 2026 | Listed | $975,000 | — |
NeighbourhoodSample data
Reference scores for WINTER GARDEN, FL. Schools, mobility and amenities feed live data once the dedicated provider connection lands.
Location
Similar homes nearby
Homes for sale in WINTER GARDEN within the same price band.
