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$779,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,750 Sq. Ft.
  • Updated 1 day ago
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Location, location, location! Nestled in a quiet, safe, single-loop community of just 47 homes with no through traffic, this beautifully updated pool home sits beneath mature oak tree-lined streets and offers the perfect blend of privacy, convenience, and modern upgrades. Situated in the highly desirable area of Dr. Phillips and served by A-rated schools, the home is also within walking distance to restaurants, Fresh Market, coffee shops, salons, medical services, and everyday conveniences. Extensive recent updates include new roof and skylights (2024), exterior paint (2025), hot water heater (2025), Bosch dishwasher (2025), new kitchen cabinetry (2025), and new flooring in the entry and kitchen (2025). The pool was newly refinished in 2025, creating a beautiful outdoor retreat ideal for relaxing or entertaining. The home features an open floor plan, custom arched windows that fill the interior with natural light, and French doors from both the living area and primary suite leading directly to the pool. The custom remodeled primary bathroom (2024) and remodeled laundry room (2023) add thoughtful modern touches. The kitchen and two bathrooms feature granite countertops, while the pool bathroom includes elegant marble counters. Appliances include a Maytag convection microwave oven, GE refrigerator and a new Samsung extra-large washer and dryer set. Built in 1989 by respected builder David Weekley, this home combines timeless construction with modern upgrades and an unbeatable location just minutes from Downtown Orlando, Walt Disney World, and Universal Studios Orlando. Schedule a viewing today!

Full Property Details for 4433 Winderwood Cir

General

  • Price: $779,000
  • HOA FEE: $35/month
  • HOA FEE FREQ.: Annually
  • Taxes: $4,678 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6391295
  • Updated: 3/17/2026
  • Added to Site: 2 day(s) ago

Rental Information

  • Min. Lease: 6 Months

Interior

  • Number of Rooms: 6
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Skylight(s), Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Masonry
  • Appliances: Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Luxury Vinyl, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Diving Board, In Ground, Outside Bath Access
  • Security/Safety: Fire Alarm, Security System

Exterior

  • Exterior Features: Fire Pit, French Doors, Irrigation System, Outdoor Grill, Outdoor Shower, Rain Gutters, Sidewalk
  • Deck/Patio: Covered, Patio, Screened
  • Porch/Patio/Deck: Covered, Patio, Screened

Parking

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

Location

  • Area: 32835 - Orlando/Metrowest/Orlo Vista
  • County: Orange
  • Development Name: 32835 - Orlando/Metrowest/Orlo Vista
  • Subdivision: WINDERWOOD
  • Driving Directions: Head toward Hal Ct. Take Good Homes Rd and S Apopka Vineland Rd to Winderside Pl. Drive to Winderwood Cir
  • Direction Faces: West

School Information

  • Elementary School: Windy Ridge Elem
  • Middle School: Windy Ridge (K-8)
  • High School: Olympia High

Community

  • Community Name: 32835 - Orlando/Metrowest/Orlo Vista
  • Community Features: Sidewalks
  • Association: Yes
  • Assoc. Name: Jan Addison
  • Assoc. Fees Include: Electricity, Escrow Reserves Fund, Insurance, Maintenance Repairs, Water

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: Electricity Available, Water Connected

Structural Information

  • Architectural Info: Florida
  • Architectural Style: Florida
  • Exterior Const.: Block, Concrete, Stucco
  • Roof: Shingle
  • Windows: Drapes, Rods, Shades
  • Stories/Levels: One
  • Square Feet: 2,750
  • Sq. Ft. Source: Owner
  • Year Built: 1989

Lot Features

  • Property View: Pool
  • Lot Size (Acres): 0.25
  • Lot Size (Sq. Ft.): 11,050
  • Lot Size: 11050
  • Frontage: Street Paved, Private Road
  • Street/Road Desc.: Paved
  • Fencing (Description): Vinyl, Wood

Financial Considerations

  • Association Fee: $418
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $4,678.08
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINDERWOOD 18/13 LOT 27
  • Flood Zone Info: X
  • APN: 112328933300270
  • Property ID: 112328933300270
Buyer's Brokerage Compensation: Contact Listing Agent
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— 4433 Winderwood Cir —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 4433 Winderwood Cir

School District:Orange County School District
NameGradesDistance
Windy Ridge K-8
3900 Beech Tree Drive, Orlando, FL 32835
K-80.7 mi
Chain Of Lakes Middle School
8700 Conroy Windermere Road, Orlando, FL 32835
6-80.9 mi
Olympia High School
4301 South Apopka Vineland Road, Orlando, FL 32835
9-121 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 4433 Winderwood Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/17/2026
Listed
$779,000
262.49%
MLS
9/23/1999
Sold
$214,900
—
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 4433 Winderwood Cir

Year
Property Taxes
Change
Tax Assessment
Change
2024
$4,434
—
$289,258
3%
2024
$4,434
8%
$281,106
3%
2023
$4,121
6%
$272,918
6%
2021
$3,894
-2%
$257,251
-3%
2022
$3,955
2%
$264,969
4%
2021
$3,894
2%
$253,699
2%
2019
$3,821
1%
$247,995
2%
2018
$3,770
1%
$243,371
2%
2017
$3,716
1%
$238,365
2%
2016
$3,682
-2%
$233,462
1%
2015
$3,740
-1%
$231,839
1%
2014
$3,794
2%
$229,999
2%
2013
$3,725
—
$226,600
—
View All
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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4433 Winderwood Circle, Orlando, FL 32835 (MLS# O6391295) is a Single Family property with 4 bedrooms and 3 full bathrooms. 4433 Winderwood Circle is currently listed for $779,000 and was received on March 17, 2026. This property is listed by Monica Perlas from our Southwest Orlando Office.Want to learn more about 4433 Winderwood Circle? Do you have questions about finding other Single Family real estate for sale in Orlando? You can browse all Orlando real estate or contact a Coldwell Banker agent to request more information.

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