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$825,000 Just Listed
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Property Description
NOTICE: This home was never supposed to be for sale, and honestly it shouldn't be. But life had other plans. More on that in a moment. Since this residence is now available, here's why this opportunity is so rare. It's located in Cypress Landing where peaceful neighborhood living meets effortless access to everything Orlando has to offer. Just minutes from famous Restaurant Row, Universal Orlando, Walt Disney World and SeaWorld, this home places you right in the center of it all, yet tucked away in a quiet, established community. Imagine evenings spent dining on Restaurant Row, weekends by your private pool, and effortless access to world-class entertainment and shopping. When you step inside the first thing you notice is the soaring 14 ft tall ceilings that immediately open up the home. This semi-custom home has everything you'd expect in a home of the stature, a formal living room, of course overlooking the pool, and formal dining room for holiday meals. But where this home really shines is where life happens, the kitchen and family room. With upgraded appliances, granite countertops, and a layout that opens seamlessly into the family room, everything flows toward the pool and oversized backyard. The home offers a spacious layout with a true split floor plan, offering real owner privacy, while the upstairs bonus room gives you flexibility as a home office, media room, "teenager apartment" or even a private guest retreat with its own bathroom. A couple of things to note that you certainly won't find in other homes; the entire HVAC system replaced 2025, including ducts, air handlers, exterior units; full plumbing re-pipe 2025; septic drain field replaced 2024; fresh interior and exterior paint 2025; new water heater 2020; updated vanities, toilets, countertops and lighting in three of four bathrooms. Step outside and enjoy your own private pool, perfect for relaxing afternoons or entertaining friends after a day at the parks. Something that Floridians know and most out-of-state buyers find out the hard way, the importance of an East facing backyard. In Florida, that's a BIG deal - it's the difference between a lanai you actually use and one that looks great in photos but sits empty every afternoon. Homes with the West facing backyards and lanais are unusable with the afternoon sun because it gets so hot. In this home, you'll have the morning sun and the coolness of the shade in the afternoon. A perfect environment for outdoor grilling and entertaining. It's a forever home, and speaking of that, the owners were never selling. The kids grew up here. Schools were minutes away. Holidays, birthdays, grandchildren by the pool this house holds countless memories. They weren't planning to leave. But life changes. A loss in the family and after a while, the pull of her home state, where generations of family are waiting - brothers, sisters, lifelong friends, and grandchildren. You can imagine the emotional "calling" to return there, and it wasn't an easy decision. But it's the right one. And that's the only reason this home is now available. We'd like to invite you to come take a look. Wouldn't it be wonderful if this was your forever home? Schedule your private showing today.
Full Property Details
Full Property Details for 3865 Winding Lake Cir
General
- Price: $825,000
- HOA FEE: $60/month
- HOA FEE FREQ.: Annually
- Taxes: $6,531 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6398496
- Updated: Today (4/13/2026)
- Added to Site: Today
Rental Information
- Min. Lease: 1-2 Years
Interior
- Number of Rooms: 9
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Family Room, Wood Burning
- Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Carpet, Ceramic Tile
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 4
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Basketball Court, Pickleball Court(s), Playground
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, In Ground, Screen Enclosure
- Spa: Yes
- Spa Description: In Ground
Exterior
- Exterior Features: Rain Gutters, Sidewalk, Sliding Doors, Sprinkler Metered
- Deck/Patio: Enclosed, Rear Porch, Screened
- Porch/Patio/Deck: Enclosed, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Driveway, Garage Faces Side
Location
- Area: 32835 - Orlando/Metrowest/Orlo Vista
- County: Orange
- Development Name: 32835 - Orlando/Metrowest/Orlo Vista
- Subdivision: CYPRESS LANDING PH 01
- Driving Directions: Conroy-Windermere Rd, West past Hiawassee Rd, right on Cypress Landing, house on the right.
- Direction Faces: West
School Information
- Elementary School: Windy Ridge Elem
- Middle School: Southwest Middle
- High School: Olympia High
Community
- Community Name: 32835 - Orlando/Metrowest/Orlo Vista
- Community Features: Deed Restrictions, Playground, Tennis Court(s)
- Optional Amenities: Basketball Court, Pickleball Court(s), Playground
- Association: Yes
- Assoc. Name: Carrie Culp
- Number of Pets: 2
- Pet Restrictions: Buyer to check with county and HOA.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Septic Tank
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Water Connected
Structural Information
- Architectural Info: Contemporary
- Architectural Style: Contemporary
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Windows: Blinds
- Stories/Levels: Two
- Square Feet: 3,194
- Sq. Ft. Source: Public Records
- Year Built: 1996
Lot Features
- Lot Size (Acres): 0.35
- Lot Size (Sq. Ft.): 15,310
- Lot Size: 15310
- Street/Road Desc.: Asphalt
Financial Considerations
- Association Fee: $723
- Assoc Fee Freq.: Annually
- Assoc Fee Desc.: Required
- Tax Amount: $6,531.13
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: CYPRESS LANDING PHASE ONE 33/3 LOT 11
- Flood Zone Info: X
- APN: 102328191400110
- Property ID: 102328191400110
- Block/Lot/Section: 00/00
Listed by Exp Realty Llc
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Schools
Schools serving 3865 Winding Lake Cir
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Windy Ridge K-8 3900 Beech Tree Drive, Orlando, FL 32835 | K-8 | 0.6 mi |
Chain Of Lakes Middle School 8700 Conroy Windermere Road, Orlando, FL 32835 | 6-8 | 0.8 mi |
Olympia High School 4301 South Apopka Vineland Road, Orlando, FL 32835 | 9-12 | 0.8 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 3865 Winding Lake Cir
Date
Details
Price
Change
Source
4/13/2026
Listed
$825,000
—
MLS
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
Tax History for 3865 Winding Lake Cir
Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,260
—
$403,977
3%
2024
$6,260
7%
$392,592
3%
2023
$5,851
6%
$381,157
6%
2021
$5,539
-2%
$359,277
-3%
2022
$5,644
2%
$370,055
4%
2021
$5,539
2%
$354,317
2%
2019
$5,417
1%
$346,351
2%
2018
$5,356
2%
$339,893
2%
2017
$5,272
1%
$332,902
2%
2016
$5,244
-2%
$326,055
1%
2015
$5,332
-1%
$323,788
1%
2014
$5,396
2%
$321,218
1%
2013
$5,292
—
$316,471
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 3865 Winding Lake Cir
3865 Winding Lake Circle, Orlando, FL 32835 (MLS# O6398496) is a Single Family property with 4 bedrooms and 4 full bathrooms. 3865 Winding Lake Circle is currently listed for $825,000 and was received on April 13, 2026. Want to learn more about 3865 Winding Lake 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.

