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$965,000
14 Days On Site

9566 BOLERO ROAD
WINTER GARDEN, FL 34787

For Sale|Single Family Residence|Active
5
Beds
4
Total Baths
3
Full Baths
1
Partial Bath
3,910
SqFt
$247
/SqFt
2021
Built
Subdivision:
WATERLEIGH PH 3A
County:
Orange

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9566 BOLERO ROAD9566 BOLERO ROAD9566 BOLERO ROAD9566 BOLERO ROAD
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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! Seller is offering $10,000 toward the buyer’s closing costs! Take advantage of this incredible opportunity to reduce your out-of-pocket expenses and make owning this beautiful Winter Garden home even more attainable.

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Listing Snapshot
Price 
$965,000
Days On Site 
14 Days
Bedrooms 
5
Inside Area (SqFt) 
3,910 sqft
Total Baths 
4
Full Baths 
3
Partial Baths 
1
Lot Size 
0.18 Acres
Year Built 
2021
MLS® Number 
O6431472
Status 
Active
Property Tax 
$14,421.76
HOA/Condo/Coop Fees 
$277 monthly
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
yesterdayListing updated with changes from the MLS®
3 days agoPrice changed to $965,000
3 days agoStatus changed to Active
2 weeks agoListing first seen on site
General Features
Acres 
0.18
Attached Garage 
Yes
Direction Faces 
Southeast
Foundation 
Slab
Garage 
Yes
Garage Spaces 
2
Levels 
Two
Number Of Stories 
2
Parking 
DrivewayAttached
Pets 
Cats OKDogs OK
Property Sub Type 
Single Family Residence
Security 
Smoke Detector(s)
Sewer 
Public Sewer
SqFt Total 
3910
Style 
Craftsman
Utilities 
Cable AvailableCable ConnectedElectricity ConnectedSewer ConnectedWater Connected
Water Source 
Public
Zoning 
P-D
Interior Features
Appliances 
CooktopDishwasherDisposalFreezerIce MakerMicrowaveRange HoodRefrigeratorTrash Compactor
Cooling 
Central Air
Flooring 
CarpetCeramic Tile
Furnished 
Unfurnished
Heating 
Central
Interior 
High CeilingsOpen FloorplanSmart Home
Laundry Features 
Electric Dryer HookupInsideWasher Hookup
Window Features 
Blinds
Bathroom 2 
Level - First
Bathroom 3 
Level - Second
Bathroom 4 
Level - Second
Bedroom 2 
Level - Second
Bedroom 3 
Level - Second
Bedroom 4 
Level - Second
Bedroom 5 
Level - Second
Dinette 
Level - First
Dining Room 
Level - First
Kitchen 
Level - FirstFeatures - Granite Counters, Kitchen Island
Living Room 
Level - First
Loft 
Level - Second
Master Bathroom 
Level - FirstFeatures - Double Vanity
Master Bedroom 
Level - First
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Exterior Features
Construction Details 
Block
Exterior 
Rain Gutters
Fencing 
Fenced
Lot Features 
Cul-De-Sac
Other Structures 
Gazebo
Patio And Porch 
CoveredFront PorchRear Porch
Roof 
Tile
View 
Water
Waterview 
Water
Windows/Doors 
Blinds
Community Features
Association Dues 
277
Community Features 
ClubhouseFitness CenterParkPlaygroundPoolTennis Court(s)Street Lights
Financing Terms Available 
CashConventionalVA Loan
HOA Fee Frequency 
Monthly
MLS Area 
34787 - Winter Garden/Oakland
Roads 
Asphalt
Township 
24
Schools
School District
Unknown
Elementary School
Water Spring Elementary
Middle School
Water Spring Middle
High School
Horizon High School
Listing courtesy of ERA GRIZZARD REAL ESTATE (407) 405-0911



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-08-26 02:37 AM EDT

Neighborhood & Commute
Source: Walkscore
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