
$2,199,000
505 Jennifer Lane
Windermere, FL 34786
Listing updated: June 10, 2026 at 4:11 PM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
Villa Casablanca | Luxury Windermere Estate on 1-Acres— this estate makes an immediate architectural statement. A circular motor court, tiered fountain, and mature canopy trees establish presence before you ever step inside. What unfolds within is architectural theater. Vaulted ceilings rise to a dramatic 14-foot peak as skylights and expansive windows flood the interiors with natural light. A sculptural chandelier crowns the volume, while a full-height stone fireplace ascends as the focal point. French glass doors frame panoramic views of the private rear oasis — creating a seamless connection between interior grandeur and outdoor serenity. The chef’s kitchen commands attention. A grand Taj Mahal quartzite island defines the center. White oak cabinetry spans floor to ceiling. The Thor range and sculpted hood rise against a full-height stone backdrop. pot filler., Viking refrigerator. Glass pendants hover overhead -- Every finish carries presence. The scullery unfolds unexpected, elevated, and unforgettable — Deep olive custom cabinetry, textured tile, LED-lit shelving, beverage refrigeration, and layered storage make it as functional as it is striking. A split plan introduces the primary suite — vaulted, private, composed. A sculptural chandelier anchors the ceiling while tailored wall moldings define the room. Dual concealed walk-in closets preserve symmetry. The primary bath is a statement of design: matte stone soaking tub beneath clerestory light, full-height stone extending into a curbless marble shower, dual tailored vanities with brushed brass accents, and patterned marble floor grounding the space in immersive opulence. An adjoining vaulted extension captures pool views and opens to the lanai. The powder room shifts tone — charcoal paneled walls, sculptural marble sink, polished brass fittings, arched mirror, and bold tile creating a rich, moody presence. A formal office behind glass French doors offers focused productivity and polished presentation. An arched corridor leads to the secondary wing where three additional bedrooms offer privacy and versatility. One suite provides direct exterior access, functioning as a cabana retreat with its own en suite bath — ideal for guests or seamless indoor-outdoor living. Outdoors, the property transforms into a private compound. A covered veranda spans the rear with classical columns and herringbone flooring. The fully equipped summer kitchen, custom wood pergola lounge, expansive lawn, fresh sod, rear gate access, and lush landscaping offer scale impossible to replicate in today’s market. Villa Casablanca is not comparable to new construction. It is rarer.
Estimated monthly payment
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 history37 days on market
- Status: SoldJun 10, 2026
- Listed$2,250,000Feb 27, 2026
- Price reduced$2,199,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Sold
- Days on market
- 37
- Subdivision
- Windermere Oaks
- County
- Orange
- Year built
- 1989
- Living area
- 3,525 sq ft
- Price/sq ft
- $624
- Building area
- 5,344 sq ft (Public Records)
- Lot size
- 43,566 sq ft
- Lot category
- 1 to less than 2
- Flood zone
- X (12095C0385F)
- Garage
- 3 spaces
- Pool
- Private pool
- Annual taxes
- $7,624 (2024)
- Parcel #
- 09-23-28-9354-00-050
- Zoning
- SFR
- MLS #
- O6384643
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Half bathrooms
- 1
- Flooring
- Hardwood, Tile
- Appliances
- Dishwasher, Disposal, Microwave, Range, Range Hood, Refrigerator
- Interior features
- Built-in Features, Ceiling Fans(s), Chair Rail, Dumbwaiter, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s)
- Laundry
- Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
- Stories / Levels
- One
- Direction faces
- West
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 3
- Attached garage
- Yes
- Parking features
- Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Oversized, Parking Pad
HOA & Financial
- HOA fee
- $4,000 / Annually
- Monthly HOA
- $333/mo
- Total monthly fees
- $333/mo
- Total annual fees
- $4,000
- HOA name
- Stuart Atherton
- CDD
- No
- Min lease term
- No Minimum
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Buyer responsible for verifying all lease restrictions.
- Approval process
- Buyer responsible for verifying all lease restrictions.
Exterior & Construction
- Exterior features
- French Doors, Lighting
- Construction materials
- Brick, Stucco
- Roof
- Shingle
- Foundation
- Slab
- Pool
- Private pool
- Water access
- Yes
- Road surface
- Brick, Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Well
- Utilities
- Electricity Connected
Community
- Pets allowed
- Yes
Schools
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
| Room | Level | Dimensions |
|---|---|---|
| Great Room | First | |
| Kitchen | First | |
| Primary Bedroom | First |
Listing Details
- Listing date
- 2026-02-26
- On market date
- 2026-02-27
- Original list price
- $2,250,000
- Occupant type
- Vacant
- MLS area
- 34786 - Windermere
- Listing AOR
- Orlando Regional
- Status changed
- 2026-06-10
- Tax legal description
- WINDERMERE OAKS 10/27 LOT 5
Flood risk
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
Head south on Apopka-Vineland Rd toward Isleworth. Continue past the Isleworth entrance, then turn right onto Jennifer Lane. 505 Jennifer Lane will be on your right.
Property sale history
Public records505 JENNIFER LN, Windermere 34786
- Jul 2025$1,225,000
- Sep 2024$950,000
3,259 sq ft · Built 1989 · 1.0001 acres
Sale data from Florida public records (Department of Revenue / county property appraiser). Deemed reliable but not guaranteed; may not reflect current market or MLS status. Not Stellar MLS data.
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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 June 10, 2026 at 4:11 PM 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.
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