House for rent

Pet friendly

Updated 1 Day Ago

9566 Bolero Rd
9566 Bolero Rd, Winter Garden, FL 34787, USA

Monthly rent	$4,995
Beds	5
Baths	3.5
Sqft	3,910

Monthly rent	$4,995
Beds	5
Baths	3.5
Sqft	3,910

Updated 1 Day Ago

Highlights

Pet Friendly

Location

9566 Bolero Rd, Winter Garden, FL 34787, USA

Tour 9566 Bolero Rd

Contact

Winter Garden

Legends Realty

(689) 600-6545 ext. 2

Property Overview

9566 Bolero Rd in Winter Garden offers a strong value per square foot and a large photo set that helps provide a clearer look at the home. Outdoor spaces, no breed or pet restrictions, and tile, vinyl, or hardwood floors also make it a standout for pet friendliness and everyday livability.

Things you’ll love

More space
Balcony
Extra storage

Great for

Pet owners

Amenities for 9566 Bolero Rd

Features

Patio

Community

Cats OK	Dogs OK
Fitness Center

Grounds

Community Pool	Garage Parking
Outdoor Space	Swimming Pool
Three Car Garage	Yard

Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.

Policies and fees

Applicants

One-time.

Contact Property

REQUIRED FEES

Security Deposit

One-time. Refundable.

Contact Property

Dog Policy

Allowed

Limit1

Cat Policy

Allowed

Limit1

Questions about this property’s policies and fees?

About 9566 Bolero Rd

Home

Houses in Winter Garden

9566 Bolero Rd, Winter Garden, FL 34787, USA

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 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.

Property highlights

How 9566 Bolero Rd compares to other nearby properties.

Positives

More space: The 5-bedroom is 556 sqft larger than other listings nearby
Balcony: Easy access to the outdoors
Extra storage: In-unit features
Fitness center: The gym is just a few steps away
Images Available: There are at least 10 photos of this property
Laundry available on site: Washers and dryers are available in-building

Considerations

No in-unit dishwasher: Dishwashers aren't available

Address details

Zip code	34787
Type	House for rent

Get the latest listings anytime, anywhere

Receive similar listings in the area, download our app, and more.

Rent trends in Winter Garden

Median rents as of Oct 3 2026.

Winter Garden

A table of 4-bedroom apartment rental data trends in Winter Garden
Month	Median Rent
October 2024	$3,097
November 2024	$3,100
December 2024	$3,200
January 2025	$3,199
February 2025	$3,100
March 2025	$3,092
April 2025	$3,097
May 2025	$3,092
June 2025	$3,118
July 2025	$3,212
August 2025	$3,200
September 2025	$3,093
October 2025	$3,007
November 2025	$3,015
December 2025	$3,075
January 2026	$3,071
February 2026	$3,099
March 2026	$3,193
April 2026	$3,156
May 2026	$3,120
June 2026	$3,187
July 2026	$3,200
August 2026	$3,200
September 2026	$3,200
October 2026	$3,200