Under contract-accepting backup offers. 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.
Property Details
Price:
$825,000
MLS #:
O6398496
Status:
Pending
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
CYPRESS LANDING PH 01
Neighborhood:
32835orlandometrowestorlovista
Listed Date:
Apr 13, 2026
Finished Sq Ft:
3,194
Total Sq Ft:
3,194
Lot Size:
15,310 sqft / 0.35 acres (approx)
Year Built:
1996
See this Listing
Schools
Elementary School:
Windy Ridge Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High
Interior
Appliances
Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry Features
Laundry Room
Levels
Two
Exterior
Architectural Style
Contemporary
Association Amenities
Basketball Court, Pickleball Court(s), Playground
Attached Garage YN
1
Community Features
Deed Restrictions, Playground, Tennis Court(s)
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
West
Exterior Features
Rain Gutters, Sidewalk, Sliding Doors, Sprinkler Metered
Garage Spaces
3
Open Parking YN
1
Parking Features
Driveway, Garage Faces Side
Patio And Porch Features
Enclosed, Rear Porch, Screened
Roof
Shingle
Spa Features
In Ground
Window Features
Blinds
Financial
HOA Fee
$723
HOA Fee Frequency
Annually
HOA Name
Carrie Culp
HOA Phone
407-455-5950
Tax Year
2025
Taxes
$6,531
Map
Community
- Address3865 WINDING LAKE CIRCLE ORLANDO FL
- SubdivisionCYPRESS LANDING PH 01
- CityORLANDO
- CountyOrange
- Zip Code32835
Market Summary
Current real estate data for Single Family in ORLANDO as of Apr 19, 2026
2,988
Single Family Listed
101
Avg DOM
288
Avg $ / SqFt
$666,632
Avg List Price
Property Summary
- Located in the CYPRESS LANDING PH 01 subdivision, 3865 WINDING LAKE CIRCLE ORLANDO FL is a Single Family for sale in ORLANDO, FL, 32835. It is listed for $825,000 and features 4 beds, 4 baths, and has approximately 3,194 square feet of living space, and was originally constructed in 1996. The current price per square foot is $258. The average price per square foot for Single Family listings in ORLANDO is $288. The average listing price for Single Family in ORLANDO is $666,632. To schedule a showing of MLS#o6398496 at 3865 WINDING LAKE CIRCLE in ORLANDO, FL, contact your agent at 407-583-9870.
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Courtesy of EXP REALTY LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than include the name of the listing broker. Neither the listing company nor shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 3865 WINDING LAKE CIRCLE
ORLANDO, FL
