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. Located just minutes from Downtown Orlando, Walt Disney World, and Universal Studios Orlando.
Sold for $779,000
Zestimate®
$779,000
4433 WINDERWOOD CIRCLE, ORLANDO, FL 32835
4beds
2,750sqft
Single Family Residence
Built in 1989
0.25 Acres Lot
$779,000 Zestimate®
$283/sqft
$3,746 Estimated rent
Home value
$779,000
$717,000 - $849,000
$3,746/mo
Zestimate® history
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List your homeWhat's special
Beautifully updated pool homeNew roofExterior paintOpen floor planHot water heaterNew kitchen cabinetryRemodeled laundry room
Zillow last checked:
Listing updated:
Listed by:
Monica Perlas 407-446-8086,
COLDWELL BANKER REALTY 407-352-1040
Bought with:
Brad Kramer, 3501369
KELLER WILLIAMS ADVANTAGE 2 REALTY
Source: Stellar MLS,MLS#: O6391295
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 273 Square Feet
- Dimensions: 21x13
Bathroom 1
- Level: First
- Area: 209 Square Feet
- Dimensions: 19x11
Bathroom 2
- Level: First
- Area: 132 Square Feet
- Dimensions: 11x12
Dining room
- Level: First
- Area: 210 Square Feet
- Dimensions: 15x14
Kitchen
- Level: First
- Area: 275 Square Feet
- Dimensions: 11x25
Living room
- Level: First
- Area: 357 Square Feet
- Dimensions: 17x21
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Refrigerator, Washer
- Laundry: Laundry Room
Features
- Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s)
- Flooring: Ceramic Tile, Luxury Vinyl, Tile
- Doors: French Doors, Outdoor Grill, Outdoor Shower
- Windows: Skylight(s), Window Treatments
- Has fireplace: Yes
- Fireplace features: Masonry
Interior area
- Total structure area: 3,454
- Total interior livable area: 2,750 sqft
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Garage Door Opener
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: One
- Stories: 1
- Patio & porch: Covered, Patio, Screened
- Exterior features: Fire Pit, Irrigation System, Outdoor Grill, Outdoor Shower, Rain Gutters, Sidewalk
- Has private pool: Yes
- Pool features: Diving Board, In Ground, Outside Bath Access
- Fencing: Vinyl,Wood
- Has view: Yes
- View description: Pool
Lot
- Size: 0.25 Acres
- Features: Sidewalk, Unincorporated
Details
- Parcel number: 112328933300270
- Zoning: R-1AA
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Florida
- Property subtype: Single Family Residence
Materials
- Block, Concrete, Stucco
- Foundation: Slab
- Roof: Shingle
Condition
- Completed
- New construction: No
- Year built: 1989
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Electricity Available, Water Connected
Community & HOA
Community
- Features: Sidewalks
- Security: Fire Alarm, Security System
- Pet fee: $0 monthly
- Subdivision: WINDERWOOD
HOA
- Has HOA: Yes
- Services included: Electricity, Reserve Fund, Insurance, Maintenance Repairs, Water
- HOA fee: $35 monthly
- HOA name: Jan Addison
- HOA phone: 407-758-9860
Location
- Region: Orlando
Financial & listing details
- Price per square foot: $283/sqft
- Tax assessed value: $540,038
- Annual tax amount: $4,678
- Date on market: 3/17/2026
- Cumulative days on market: 41 days
- Listing terms: Cash,Conventional,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 5/12/2026 | Sold | $779,000$283/sqft |
Source:  Stellar MLS #O6391295 Report a problem | ||
| 4/28/2026 | Pending sale | $779,000$283/sqft |
Source: Stellar MLS #O6391295 Report a problem | ||
| 3/17/2026 | Listed for sale | $779,000+0.5%$283/sqft |
Source: Stellar MLS #O6391295 Report a problem | ||
| 1/16/2026 | Listing removed | -- |
Source: Owner Report a problem | ||
| 1/9/2026 | Price change | $775,000-1.1%$282/sqft |
Source: Stellar MLS #O6353692 Report a problem | ||
| 12/13/2025 | Price change | $784,000-1.9%$285/sqft |
Source: Space Coast AOR #1060860 Report a problem | ||
| 10/26/2025 | Price change | $799,000-3.1%$291/sqft |
Source: Stellar MLS #O6353692 Report a problem | ||
| 10/19/2025 | Price change | $824,900-3%$300/sqft |
Source: Stellar MLS #O6353692 Report a problem | ||
| 10/18/2025 | Price change | $850,000+1.6%$309/sqft |
Source: Owner Report a problem | ||
| 10/3/2025 | Listed for sale | $837,000+289.5%$304/sqft |
Source: Owner Report a problem | ||
| 9/23/1999 | Sold | $214,900$78/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $4,434 +7.6% | $281,106 +3% |
| 2023 | $4,121 +4.2% | $272,918 +3% |
| 2022 | $3,955 +1.6% | $264,969 +3% |
| 2021 | $3,894 +0.7% | $257,251 +1.4% |
| 2020 | $3,868 +1.2% | $253,699 +2.3% |
| 2019 | $3,821 +1.3% | $247,995 +1.9% |
| 2018 | $3,770 | $243,371 -23.9% |
| 2017 | $3,770 +1.5% | $319,703 +2% |
| 2016 | $3,716 +0.9% | $313,389 +10.7% |
| 2015 | $3,682 -3% | $283,100 +15.7% |
| 2014 | $3,794 +1.9% | $244,744 +6.6% |
| 2013 | $3,725 +0.9% | $229,677 +3.1% |
| 2012 | $3,692 +0.3% | $222,812 -4.2% |
| 2011 | $3,680 +4.4% | $232,627 -4.9% |
| 2010 | $3,526 | $244,598 -13.6% |
| 2009 | -- | $283,072 -15.9% |
| 2008 | $3,256 -2.2% | $336,444 -7.5% |
| 2007 | $3,329 -5.8% | $363,542 +12.4% |
| 2006 | $3,533 +1.3% | $323,422 +25% |
| 2005 | $3,487 +4.6% | $258,635 +11.5% |
| 2004 | $3,334 +0.6% | $231,915 +9.9% |
| 2003 | $3,316 +2.8% | $210,975 +3.7% |
| 2002 | $3,224 -1.4% | $203,481 +10.8% |
| 2001 | $3,271 +2.5% | $183,606 +5.7% |
| 2000 | $3,192 | $173,771 |
Find assessor info on the county website
Neighborhood: 32835
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Nearby schools
GreatSchools rating
- 9/10Windy Ridge K-8Grades: PK-8Distance: 0.7 mi
- 5/10Olympia High SchoolGrades: 9-12Distance: 1 mi
- 3/10Chain Of Lakes Middle SchoolGrades: 6-8Distance: 0.9 mi
Schools provided by the listing agent
- Elementary: Windy Ridge Elem
- Middle: Windy Ridge (K-8)
- High: Olympia High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$779,000
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Estimated market value
$779,000
- Florida
- Orange County
- Orlando
- 32835
- 4433 WINDERWOOD CIRCLE
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