


$950,000
9566 Bolero Road
Winter Garden, FL 34787
Listing updated: August 27, 2026 at 11:42 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
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! BUYER INCENTIVE INSTANT EQUITY OPPORTUNITY! Take advantage of this incredible opportunity home currently listed $100k under market value.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history11 days on market
- Status: ActiveAug 23, 2026
- Listed$975,000Aug 13, 2026
- Price reduced$950,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 11
- Subdivision
- Waterleigh Ph 3a
- County
- Orange
- Year built
- 2021
- Living area
- 3,910 sq ft
- Price/sq ft
- $243
- Lot size
- 7,961 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X (12095C0375F)
- Garage
- 2 spaces
- Annual taxes
- $14,422 (2025)
- Parcel #
- 07-24-27-7506-00-150
- Zoning
- P-D
- MLS #
- O6431472
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Interior Details
- Bedrooms
- 5
- Full bathrooms
- 3
- Half bathrooms
- 1
- Flooring
- Carpet, Ceramic Tile
- Appliances
- Cooktop, Dishwasher, Disposal, Freezer, Ice Maker, Microwave, Range Hood, Refrigerator, Trash Compactor
- Interior features
- High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Smart Home, Solid Surface Counters, Split Bedroom, Thermostat, Window Treatments
- Laundry
- Electric Dryer Hookup, Inside, Washer Hookup
- Stories / Levels
- Two
- Direction faces
- Southeast
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Driveway
HOA & Financial
- HOA fee
- $277 / Monthly
- Monthly HOA
- $277/mo
- Total monthly fees
- $277/mo
- Total annual fees
- $3,324
- HOA name
- Access Residential Management
- CDD
- No
- Min lease term
- 1-2 Years
- Listing terms
- Cash, Conventional, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Buyer agent to verify with HOA
Exterior & Construction
- Exterior features
- Rain Gutters
- Construction materials
- Block
- Roof
- Tile
- Foundation
- Slab
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Connected, Electricity Connected, Sewer Connected, Sprinkler Recycled, Water Connected
Community
- Pets allowed
- Cats OK, Dogs OK
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | |
| Primary Bathroom | First | |
| Bedroom 2 | Second | |
| Bedroom 3 | Second | |
| Bedroom 4 | Second | |
| Bedroom 5 | Second | |
| Bathroom 2 | First | |
| Bathroom 3 | Second | |
| Bathroom 4 | Second | |
| Kitchen | First | |
| Living Room | First | |
| Dining Room | First | |
| Dinette | First | |
| Loft | Second |
Listing Details
- Listing date
- 2026-08-06
- On market date
- 2026-08-13
- Original list price
- $975,000
- Occupant type
- Tenant
- MLS area
- 34787 - Winter Garden/Oakland
- Listing AOR
- Orlando Regional
- Status changed
- 2026-08-23
- Tax legal description
- WATERLEIGH PHASE 3A 99/54 LOT 15
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
429 TO SCHOFIELD RD | RIGHT ON AVALON RD | RIGHT ON WATERWAY PASSAGE DR | RIGHT ON POINT ROCK DR | LEFT ON BOLERO RD
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Listings courtesy of Stellar MLS as distributed by MLS GRID
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.
Based on information submitted to the MLS GRID as of August 27, 2026 at 11:42 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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