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$2,099,999

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 2 Partial Baths
  • 4,498 Sq. Ft.
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Experience breathtaking lakefront living in this exceptional estate home with a private dock in one of Winter Garden's most sought-after gated communities: Hickory Hammock at Johns Lake. Perfectly positioned on the shores of Johns Lake, this spacious 5-bedroom, 4 full-bath, 2 half-bath residence offers the ideal combination of elegance, comfort, and outdoor adventure. Whether unwinding on the dock at sunset, setting out for a day of boating and fishing, or simply enjoying the serenity of the water from the private backyard, this home provides a rare opportunity to embrace the Florida lifestyle. Designed for both entertaining and everyday living, the thoughtfully crafted interior features an expansive open floor plan with abundant natural light. The chef-inspired kitchen boasts double islands, premium cabinetry, Silestone countertops, a stylish glass tile backsplash, and a reverse osmosis system, with an adjacent walk-in pantry for added convenience. The family room is designed for comfort, complete with built-in surround sound and seamless indoor-outdoor connectivity through triple sliding doors leading to a covered lanai with retractable screens. A first-floor guest suite includes a private bath and custom Murphy bed, offering flexible space for visitors or a home office, with its own lanai access. Upstairs, the game room with office nook provides additional living space, while the primary suite is a true retreat, featuring French doors opening to a screened balcony with stunning lake views. The luxurious primary bath includes dual vanities, upgraded cabinetry, a walk-in shower, and a garden tub, creating a spa-like atmosphere. Three additional bedrooms, including one with an en-suite bath and two sharing a Jack-and-Jill bathroom, complete the second level, along with a fully equipped laundry room. Outside, the 40' x 20' saltwater pool and expansive deck create the perfect setting for entertaining or quiet relaxation. The fully fenced backyard offers both privacy and space to enjoy the beautiful lakefront setting. As part of the prestigious Hickory Hammock community, residents have access to resort-style amenities, including a clubhouse, fitness center, tennis and volleyball courts, a fishing pier, playground, dog park, picnic areas, and scenic walking trails-plus, golf carts are welcome. Conveniently located near Winter Garden Village, historic downtown Winter Garden, top-rated hospitals, and major highways, this home also offers easy access to Disney, Universal, fine dining, luxury shopping, and entertainment.

Full Property Details for 15986 Johns Lake Overlook Dr

General

  • Price: $2,099,999
  • HOA FEE: $212/month
  • Taxes: $16,937 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6337081
  • Updated: 11/13/2025
  • Added to Site: 149 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 9
  • Interior Features: High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s)
  • Appliances: Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Washer, Water Filtration System
  • Furnishings: Unfurnished
  • Flooring: Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 4
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Clubhouse, Fitness Center, Gated, Park, Playground, Pool, Tennis Court(s)
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground, Lighting, Tile
  • Spa: Yes
  • Spa Description: Heated, In Ground

Exterior

  • Exterior Features: Balcony, Irrigation System, Lighting, Sidewalk, Sliding Doors
  • Deck/Patio: Deck, Patio, Screened
  • Porch/Patio/Deck: Deck, Patio, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3
  • Parking Features: Garage Door Opener, Garage Faces Side, On Street

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: HICKORY HAMMOCK PH 1D
  • Driving Directions: Take Exit 272 for FL-50 toward Winter Garden/Clermont, then turn right onto FL-50 West. Continue for about 4 miles, then turn left onto Hartle Road. Follow Hartle Road for approximately 2 miles, then turn right onto Johns Lake Overlook Drive. Continue straight, and 15986 Johns Lake Overlook Drive will be on your left.
  • Direction Faces: South

School Information

  • Elementary School: Whispering Oak Elem
  • Middle School: Hamlin Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Lake, Clubhouse, Dog Park, Fitness Center, Gated Community - No Guard, Park, Playground, Pool, Tennis Court(s)
  • Optional Amenities: Clubhouse, Fitness Center, Gated, Park, Playground, Pool, Tennis Court(s)
  • Association: Yes
  • Assoc. Name: Sherry Khan
  • Number of Pets: 2
  • Pet Restrictions: Verify with HOA/Orange County

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water District: JOHNS LAKE
  • Water: Public
  • Utility Description: Electricity Connected, Sewer Connected, Water Connected

Structural Information

  • Exterior Const.: Block
  • Roof: Shingle
  • Windows: Double Pane Windows, ENERGY STAR Qualified Windows
  • Stories/Levels: Two
  • Square Feet: 4,498
  • Sq. Ft. Source: Public Records
  • Year Built: 2015

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.55
  • Lot Size (Sq. Ft.): 23,872
  • Lot Size: 23872
  • Street/Road Desc.: Asphalt

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake
  • Water Extras: Yes
  • Water Front Name: JOHNS LAKE
  • Water Front Desc.: Lake, Lake Front

Financial Considerations

  • Association Fee: $212
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: None
  • Tax Amount: $16,937
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: HICKORY HAMMOCK PHASE 1D 83/116 LOT 91
  • Flood Zone Info: AE
  • APN: 322227360200910
  • Property ID: 322227360200910
  • Block/Lot/Section: 2055

Listed by Stockworth Realty Group

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Listing agent

— 15986 Johns Lake Overlook Dr —

  • Stockworth Realty Group

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 15986 Johns Lake Overlook Dr

School District:Orange County School District
NameGradesDistance
Whispering Oak Elementary School
15300 Stoneybrook West Parkway, Winter Garden, FL 34787
PK-51.2 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-123.8 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 15986 Johns Lake Overlook Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/13/2025
Price Reduced
$2,099,999
-2.33%
MLS
9/22/2025
Price Reduced
$2,150,000
-2.27%
MLS
8/22/2025
Listed
$2,200,000
109.52%
MLS
9/18/2019
Sold
$1,050,000
—
Public Record
Get Price Alerts and Save Property
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 for 15986 Johns Lake Overlook Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$16,937
—
$1,133,542
3%
2024
$16,937
5%
$1,101,596
5%
2023
$16,134
10%
$1,053,977
17%
2021
$14,625
-7%
$899,131
-12%
2022
$15,704
7%
$1,023,279
17%
2021
$14,625
37%
$874,248
29%
2019
$10,665
1%
$679,488
2%
2018
$10,585
3%
$666,818
2%
2017
$10,320
-10%
$653,103
-8%
2016
$11,468
196%
$706,985
221%
2015
$3,868
—
$220,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Stockworth Realty Group

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15986 Johns Lake Overlook Drive, Winter Garden, FL 34787 (MLS# O6337081) is a Single Family property with 5 bedrooms, 4 full bathrooms and 2 partial bathrooms. 15986 Johns Lake Overlook Drive is currently listed for $2,099,999 and was received on August 22, 2025. Want to learn more about 15986 Johns Lake Overlook Drive? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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