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$975,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,910 Sq. Ft.
  • Updated 4 days ago
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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!

Full Property Details for 9566 Bolero Rd

General

  • Price: $975,000
  • HOA FEE: $277/month
  • Taxes: $14,421 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6431472
  • Updated: 8/13/2026
  • Added to Site: 4 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 14
  • Interior Features: High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Smart Home, Solid Surface Counters, Split Bedroom, Thermostat, Window Treatments
  • Appliances: Cooktop, Dishwasher, Disposal, Freezer, Ice Maker, Microwave, Range Hood, Refrigerator, Trash Compactor
  • Furnishings: Unfurnished
  • Flooring: Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Electric Dryer Hookup, Inside, Washer Hookup

Additional Information

  • Security/Safety: Smoke Detector(s)

Exterior

  • Exterior Features: Irrigation System, Rain Gutters
  • Deck/Patio: Covered, Front Porch, Rear Porch
  • Porch/Patio/Deck: Covered, Front Porch, Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: WATERLEIGH PH 3A
  • Driving Directions: 429 TO SCHOFIELD RD | RIGHT ON AVALON RD | RIGHT ON WATERWAY PASSAGE DR | RIGHT ON POINT ROCK DR | LEFT ON BOLERO RD
  • Direction Faces: Southeast

School Information

  • Elementary School: Water Spring Elementary
  • Middle School: Water Spring Middle
  • High School: Horizon High School

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Clubhouse, Community Mailbox, Dog Park, Fitness Center, Golf Carts OK, Irrigation-Reclaimed Water, Park, Playground, Pool, Tennis Court(s)
  • Association: Yes
  • Assoc. Name: Access Residential Management
  • Pet Restrictions: Buyers agent to verify with HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Sewer Connected, Sprinkler Recycled, Street Lights, Water Connected

Structural Information

  • Architectural Info: Craftsman
  • Architectural Style: Craftsman
  • Exterior Const.: Block
  • Roof: Tile
  • Windows: Blinds
  • Stories/Levels: Two
  • Square Feet: 3,910
  • Sq. Ft. Source: Public Records
  • Year Built: 2021

Additional Structures

  • Other Structures: Gazebo

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.18
  • Lot Size (Sq. Ft.): 7,961
  • Lot Size: 7961
  • Street/Road Desc.: Asphalt
  • Fencing (Description): Fenced

Water Features

  • Water View: Yes

Green Features

  • Water Conservation: Drip Irrigation, Irrigation-Reclaimed Water

Financial Considerations

  • Association Fee: $277
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $14,421.76
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WATERLEIGH PHASE 3A 99/54 LOT 15
  • Flood Zone Info: X
  • APN: 72427750600150
  • Property ID: 72427750600150
  • Block/Lot/Section: 15

Listed by Era Grizzard Real Estate

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Listing agent

— 9566 Bolero Rd —

  • Era Grizzard Real Estate

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 9566 Bolero Rd

School District:Orange County School District
NameGradesDistance
Water Spring Elementary
16000 Water Spring Boulevard, Winter Garden, FL 34787
PK-50.8 mi
Water Spring Middle School-0482
10393 Seidel Road, Winter Garden, FL 34787
6-82.1 mi
Horizon High School
10393 Seidel Road, Winter Garden, FL 34787
9-122.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 9566 Bolero Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/13/2026
Listed
$975,000
55.83%
MLS
5/25/2021
Sold
$625,681
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 9566 Bolero Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,422
—
$845,950
-1%
2025
$14,422
5%
$855,680
4%
2024
$13,789
36%
$822,983
24%
2023
$10,152
368%
$662,012
488%
2021
$2,169
-77%
$112,500
-82%
2022
$9,580
342%
$626,885
470%
2021
$2,169
—
$110,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Era Grizzard Real Estate

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9566 Bolero Road, Winter Garden, FL 34787 (MLS# O6431472) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 9566 Bolero Road is currently listed for $975,000 and was received on August 13, 2026. Want to learn more about 9566 Bolero Road? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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