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$4,995
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Property Description
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
Full Property Details
Full Property Details for 9566 Bolero Rd
General
- Rent: $4,995
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6434084
- Added to Site: 46 day(s) ago
Rental Information
- Lease/Rent Term: 12 Months
Interior
- Interior Features: Other
- Appliances: Other
- Furnishings: Unfurnished
- Flooring: Tile
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Washer Hookup
Additional Information
- Shared Amenities: Pickleball Court(s)
Exterior
- Deck/Patio: Covered, Patio
- Porch/Patio/Deck: Covered, Patio
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: WATERLEIGH PH 3A
- Driving Directions: Take FL-429 S toward Winter Garden and exit toward Schofield Road/Buena Vista area. Continue toward Bolero Road, then follow Bolero Road into the community. Continue to 9566 Bolero Rd, with the property located on the right.
Community
- Community Name: 34787 - Winter Garden/Oakland
- Community Features: Clubhouse, Dog Park, Fitness Center, Playground
- Optional Amenities: Pickleball Court(s)
- Assoc. Name: Tina Lopez
- Pet Restrictions: NO HIGH RISK BREEDS
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Structural Information
- Stories/Levels: Two
- Square Feet: 3,910
- Sq. Ft. Source: Estimated
- Living Area: 3,910 Sq. Ft.
- Year Built: 2021
Lot Features
- Lot Size (Acres): 0.18
- Lot Size (Sq. Ft.): 7,961
- Lot Size: 7961
- Street/Road Desc.: Other
- Fencing (Description): Fenced, Full Backyard
Financial Considerations
- Lease Price: $4,995
- Application Fee: $75
- Security Deposit: $4,995
Disclosures and Reports
- Flood Zone Info: X
- APN: 72427750600150
- Property ID: 72427750600150
Listed and Sold by Legends Realty
Schools
Schools serving 9566 Bolero Rd
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Water Spring Elementary 16000 Water Spring Boulevard, Winter Garden, FL 34787 | PK-5 | 0.8 mi |
Water Spring Middle School-0482 10393 Seidel Road, Winter Garden, FL 34787 | 6-8 | 2.1 mi |
Horizon High School 10393 Seidel Road, Winter Garden, FL 34787 | 9-12 | 2.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 9566 Bolero Rd
Date
Details
Price
Change
Source
9/03/2026
Sold
$4,995
—
MLS
8/28/2026
Price Reduced
$4,995
-3.94%
MLS
8/17/2026
Listed
$5,200
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
9566 Bolero Road, Winter Garden, FL 34787 (MLS# O6434084) is a Single Family property that was sold at $4,995 on September 03, 2026. Want to learn more about 9566 Bolero Road? Do you have questions about finding other real estate for sale or rent in Winter Garden? You can browse all Winter Garden rentals or contact a Coldwell Banker agent to request more information.

