9566 Bolero Road, FL9566 Bolero Road, FL9566 Bolero Road, FL
Stellar MLS
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$950,000

9566 Bolero Road

Winter Garden, FL 34787

Listing updated: August 27, 2026 at 11:42 AM ET

Active
Stellar MLSListing courtesy of Era Grizzard Real Estate · Lisette Maestre · MLS #O6431472 · Active · 352-735-4433
5
Beds
4
Baths
3,910
Sq Ft
0.18
Acres
2021
Built
$243/sqft
Single Family Residence

Property type

2021

Year built

7,961 sqft

Lot size

$243

Price / sq ft

$277/mo

HOA dues

11

Days on market

2

Garage spaces

X

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

Principal & interest$4,804
Property taxes$1,202
Home insurance (est.)$435
HOA dues$277

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

  1. Status: Active
    Aug 23, 2026
  2. Listed$975,000
    Aug 13, 2026
  3. 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

ElementaryBWater Spring ElementaryGreatSchools ↗
MiddleWater Spring MiddleGreatSchools ↗
High SchoolAHorizon High SchoolGreatSchools ↗

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

RoomLevelDimensions
Primary BedroomFirst
Primary BathroomFirst
Bedroom 2Second
Bedroom 3Second
Bedroom 4Second
Bedroom 5Second
Bathroom 2First
Bathroom 3Second
Bathroom 4Second
KitchenFirst
Living RoomFirst
Dining RoomFirst
DinetteFirst
LoftSecond

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 riskFEMA Zone XPanel 12095C0375F

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.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

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