Welcome to 14640 Pylon Court, an extraordinary waterfront home located in the highly sought after gated community of the Isles of Lake Hancock—one of Florida’s most exclusive water ski neighborhoods. This custom-designed residence offers over 4,400 square feet of luxurious living space, five bedrooms, five full and one-half baths, a 4-car garage, and sweeping water views from both the front and back of the home. Set on a premium lot with direct views of the world-renowned championship ski courses, this home offers the ultimate blend of privacy, elegance, and recreational lifestyle. Inside, rich hardwood flooring flows through spacious, light-filled living areas, including a formal dining room with detailed ceilings, a private study, and a great room with soaring ceilings, custom built-ins, a fireplace, and expansive sliding glass doors. The gourmet kitchen features a massive island, gas appliances, double ovens, and ample cabinetry—perfect for both casual family living and entertaining on a grand scale. The luxurious primary suite includes a sitting area with lake views, dual walk-in closets, a soaking tub, walk-in shower, and dual vanities. The first-floor media room offers the perfect space for movie nights or game-day gatherings, while two additional bedrooms and a balcony complete the home’s thoughtful layout. The expansive screened lanai is ideal for outdoor living, featuring a sparkling pool, summer kitchen, manicured grounds, and tranquil water vistas. As a resident of this exclusive 54-home community, you’ll enjoy access to a residents-only boat ramp, tennis courts, playground, and recreation area. Located just minutes from all of the shopping and amenities at Hamlin, yet tucked away in a quiet, gated enclave, this home offers a rare opportunity to own one of Central Florida’s most sought-after waterfront properties—where luxury meets lifestyle.
Sold for $2,000,000
$2,000,000
14640 Pylon Ct, Winter Garden, FL 34787
5beds
4,483sqft
Single Family Residence
Built in 2017
0.45 Acres Lot
$2,048,600 Zestimate®
$446/sqft
$6,027 Estimated rent
Home value
$2,048,600
$1.88M - $2.21M
$6,027/mo
Zestimate® history
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List your homeWhat's special
Expansive screened lanaiSummer kitchenSparkling poolWaterfront homeLuxurious living spaceFirst-floor media roomGourmet kitchen
Zillow last checked:
Listing updated:
Listed by:
Steve Healy 407-230-1441,
CORCORAN PREMIER REALTY 407-965-1155,
Matt Tomaszewski 407-719-5956,
CORCORAN PREMIER REALTY
Bought with:
Drew Ross, 3053364
LAKEFIELD REALTY GROUP LLC
Source: Stellar MLS,MLS#: O6330990
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Rooms
- Room types: Den/Library/Office, Family Room, Great Room, Media Room
Primary bedroom
- Features: Dual Closets
- Level: First
- Area: 768 Square Feet
- Dimensions: 32x24
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 144 Square Feet
- Dimensions: 12x12
Bedroom 3
- Features: Built-in Closet
- Level: First
- Area: 144 Square Feet
- Dimensions: 12x12
Bedroom 4
- Features: Built-in Closet
- Level: Second
- Area: 144 Square Feet
- Dimensions: 12x12
Bedroom 5
- Features: Built-in Closet
- Level: Second
- Area: 308 Square Feet
- Dimensions: 22x14
Dining room
- Level: First
- Area: 182 Square Feet
- Dimensions: 13x14
Great room
- Level: First
- Area: 380 Square Feet
- Dimensions: 20x19
Kitchen
- Level: First
- Area: 224 Square Feet
- Dimensions: 16x14
Media room
- Level: First
- Area: 272 Square Feet
- Dimensions: 16x17
Office
- Level: First
- Area: 195 Square Feet
- Dimensions: 13x15
Heating
- Central, Zoned
Cooling
- Central Air, Zoned
Appliances
- Included: Oven, Dishwasher, Disposal, Microwave, Range, Range Hood, Refrigerator
- Laundry: Inside
Features
- Built-in Features, Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
- Flooring: Carpet, Porcelain Tile, Hardwood
- Doors: Outdoor Kitchen, Sliding Doors
- Has fireplace: Yes
- Fireplace features: Electric, Living Room
Interior area
- Total structure area: 5,992
- Total interior livable area: 4,483 sqft
Property
Parking
- Total spaces: 4
- Parking features: Garage - Attached
- Attached garage spaces: 4
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered, Rear Porch, Screened
- Exterior features: Balcony, Irrigation System, Lighting, Outdoor Kitchen, Sidewalk
- Has private pool: Yes
- Pool features: Gunite, Outside Bath Access, Salt Water, Screen Enclosure
- Has view: Yes
- View description: Water, Lake
- Has water view: Yes
- Water view: Water,Lake
- Waterfront features: Pond, Lake Privileges
Lot
- Size: 0.45 Acres
- Features: Cul-De-Sac, In County, Landscaped, Sidewalk, Street Dead-End
- Residential vegetation: Mature Landscaping, Trees/Landscaped
Details
- Parcel number: 272327274100300
- Zoning: P-D
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Block, Slab, Stem Wall
- Roof: Tile
Condition
- New construction: No
- Year built: 2017
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Connected, Electricity Connected, Propane, Street Lights, Underground Utilities, Water Connected
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: ISLES/LK HANCOCK PH III
HOA
- Has HOA: Yes
- HOA fee: $283 monthly
- HOA name: contact realtor
Location
- Region: Winter Garden
Financial & listing details
- Price per square foot: $446/sqft
- Tax assessed value: $1,632,275
- Annual tax amount: $14,542
- Date on market: 7/29/2025
- Cumulative days on market: 64 days
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 11/24/2025 | Sold | $2,000,000-13%$446/sqft |
Source:  Stellar MLS #O6330990 Report a problem | ||
| 10/2/2025 | Pending sale | $2,299,000$513/sqft |
Source: Stellar MLS #O6330990 Report a problem | ||
| 9/9/2025 | Price change | $2,299,000-4.2%$513/sqft |
Source: Stellar MLS #O6330990 Report a problem | ||
| 7/29/2025 | Listed for sale | $2,400,000+145.8%$535/sqft |
Source: Stellar MLS #O6330990 Report a problem | ||
| 1/18/2018 | Sold | $976,276$218/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $14,543 +7.3% | $921,800 +3% |
| 2023 | $13,555 +3% | $894,951 +3% |
| 2022 | $13,155 +1.2% | $868,884 +3% |
| 2021 | $12,998 -1.3% | $843,577 -0.6% |
| 2020 | $13,176 -2.1% | $848,356 -0.6% |
| 2019 | $13,455 +7.2% | $853,135 +13.9% |
| 2018 | $12,550 +0% | $748,926 +225.6% |
| 2017 | $12,550 +228% | $230,000 -19.3% |
| 2016 | $3,827 -21% | $285,000 +5.6% |
| 2015 | $4,845 | $270,000 |
Find assessor info on the county website
Neighborhood: 34787
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Nearby schools
GreatSchools rating
- 9/10Summerlake ElementaryGrades: K-5Distance: 0.7 mi
- 9/10Hamlin Middle SchoolGrades: 6-8Distance: 2.5 mi
- 6/10Horizon High SchoolGrades: 9-12Distance: 2.7 mi
Schools provided by the listing agent
- Elementary: Summerlake Elementary
- Middle: Hamlin Middle
- High: Horizon High School
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
$2,048,600
Get a cash offer in 3 minutes
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Estimated market value
$2,048,600
- Florida
- Orange County
- Winter Garden
- 34787
- 14640 Pylon Ct
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