$1,850,000
16086 JOHNS LAKE OVERLOOK DRIVE
WINTER GARDEN, FL, 34787
Presenting 16086 Johns Lake Overlook Drive – Lakefront Elegance in Hickory Hammock – $1,850,000
Wake up to sweeping views of Johns Lake and end your day with brilliant sunsets from your own backyard. Set on a half-acre with 100 feet of lake frontage, this 5-bedroom, 4 full/2 half-bath home offers 4,474 sq ft of living space, a private dock with boat lift, and a resort-style pool combining refined finishes with functional design for both everyday comfort and entertaining.
A dramatic two-story foyer with soaring ceilings sets the stage, flowing into an expansive open layout centered around a chef’s kitchen. This culinary showpiece boasts two oversized wood-wrapped islands, lustrous quartz countertops, white cabinetry with custom storage, convection oven/microwave combo, an electric cooktop, and a walk-in pantry. The adjoining dinette and spacious family room seamlessly connect through triple sliders to the screened lanai, creating an effortless indoor-outdoor living experience.
Outdoors, enjoy a heated saltwater pool with lap lane, sun shelf, and lighting, all framed by beautiful landscaping and a fully fenced yard. On the shores of John’s Lake, your dock features a 7,500-lb lift and Trex decking for durability and functionality. Also equipped with a dedicated seating area, electric and water, this space creates a versatile outdoor retreat—perfect for entertaining or enjoying the signature experiences of lakefront living.
The first floor features a private in-law suite with its own entrance, a full bath with a walk-in shower, a walk-in closet, and direct access to a screened patio. Upstairs, the primary suite showcases breathtaking lake views through a wall of windows, French doors opening to a private balcony, elegant tray ceilings, and a spa-inspired bath with dual vanities, a soaking tub, and an expansive walk-in shower. Three additional bedrooms include one with a private en-suite bath and two connected by a Jack-and-Jill bath. A generous bonus room overlooking the water offers endless possibilities—ideal for a game room, media lounge, or executive home office.
This property also features fully paid-off solar panels, providing a net $0 electric bill—a rare and valuable benefit for Florida living. Additional highlights include engineered hardwood flooring throughout, fresh interior and exterior paint (2025), and a split three-car side-entry garage. Residents also enjoy an array of resort-style amenities, including a sparkling pool, state-of-the-art fitness center, clubhouse, tennis and volleyball courts, playground, dog park, fishing pier, and scenic walking trails.
Ideally situated near Winter Garden Village, historic downtown Winter Garden, and zoned for top-rated schools, this home offers convenient access to major highways—placing Orlando and surrounding destinations just minutes away. Experience the lakefront lifestyle without compromise. Schedule your private tour today before this rare opportunity is gone.
Wake up to sweeping views of Johns Lake and end your day with brilliant sunsets from your own backyard. Set on a half-acre with 100 feet of lake frontage, this 5-bedroom, 4 full/2 half-bath home offers 4,474 sq ft of living space, a private dock with boat lift, and a resort-style pool combining refined finishes with functional design for both everyday comfort and entertaining.
A dramatic two-story foyer with soaring ceilings sets the stage, flowing into an expansive open layout centered around a chef’s kitchen. This culinary showpiece boasts two oversized wood-wrapped islands, lustrous quartz countertops, white cabinetry with custom storage, convection oven/microwave combo, an electric cooktop, and a walk-in pantry. The adjoining dinette and spacious family room seamlessly connect through triple sliders to the screened lanai, creating an effortless indoor-outdoor living experience.
Outdoors, enjoy a heated saltwater pool with lap lane, sun shelf, and lighting, all framed by beautiful landscaping and a fully fenced yard. On the shores of John’s Lake, your dock features a 7,500-lb lift and Trex decking for durability and functionality. Also equipped with a dedicated seating area, electric and water, this space creates a versatile outdoor retreat—perfect for entertaining or enjoying the signature experiences of lakefront living.
The first floor features a private in-law suite with its own entrance, a full bath with a walk-in shower, a walk-in closet, and direct access to a screened patio. Upstairs, the primary suite showcases breathtaking lake views through a wall of windows, French doors opening to a private balcony, elegant tray ceilings, and a spa-inspired bath with dual vanities, a soaking tub, and an expansive walk-in shower. Three additional bedrooms include one with a private en-suite bath and two connected by a Jack-and-Jill bath. A generous bonus room overlooking the water offers endless possibilities—ideal for a game room, media lounge, or executive home office.
This property also features fully paid-off solar panels, providing a net $0 electric bill—a rare and valuable benefit for Florida living. Additional highlights include engineered hardwood flooring throughout, fresh interior and exterior paint (2025), and a split three-car side-entry garage. Residents also enjoy an array of resort-style amenities, including a sparkling pool, state-of-the-art fitness center, clubhouse, tennis and volleyball courts, playground, dog park, fishing pier, and scenic walking trails.
Ideally situated near Winter Garden Village, historic downtown Winter Garden, and zoned for top-rated schools, this home offers convenient access to major highways—placing Orlando and surrounding destinations just minutes away. Experience the lakefront lifestyle without compromise. Schedule your private tour today before this rare opportunity is gone.
Property Details
Price:
$1,850,000
MLS #:
O6334047
Status:
Active
Beds:
5
Baths:
5
Address:
16086 JOHNS LAKE OVERLOOK DRIVE
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
HICKORY HAMMOCK PH 1D
Neighborhood:
34787 – Winter Garden/Oakland
City:
WINTER GARDEN
Listed Date:
Aug 11, 2025
State:
FL
Finished Sq Ft:
4,474
Total Sq Ft:
6,323
ZIP:
34787
Lot Size:
21,579 sqft / 0.50 acres (approx)
Year Built:
2015
Schools
Elementary School:
Whispering Oak Elem
Middle School:
Hamlin Middle
High School:
West Orange High
Interior
Appliances
Built- In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range Hood, Refrigerator, Touchless Faucet, Washer
Bathrooms
4 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Flooring
Engineered Hardwood, Laminate, Tile
Heating
Central
Laundry Features
Laundry Room
Exterior
Community Features
Dock, Fishing, Clubhouse, Community Mailbox, Deed Restrictions, Dog Park, Gated Community – No Guard, Golf Carts O K, Playground, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Block, Stucco
Exterior Features
Balcony, French Doors, Irrigation System, Lighting, Outdoor Shower, Rain Gutters
Parking Features
Driveway, Garage Door Opener
Roof
Shingle
Security Features
Gated Community, Smoke Detector(s)
Financial
HOA Fee
$201
HOA Frequency
Semi-Annually
HOA Includes
Community Pool, Recreational Facilities
HOA Name
Artemis Lifestyles/Sherri Kahn
Tax Year
2024
Taxes
$22,071
Mortgage Calculator
Map
Similar Listings Nearby
- 16098 JOHNS LAKE OVERLOOK DRIVE
WINTER GARDEN, FL$2,399,222
0.05 miles away
- 16606 BOLSENA DRIVE
MONTVERDE, FL$2,301,926
4.95 miles away
- 3413 LILAS COURT
WINDERMERE, FL$2,300,000
4.20 miles away
- 5909 OXFORD MOOR BOULEVARD
WINDERMERE, FL$2,299,995
4.61 miles away
- 4279 ISABELLA CIRCLE
WINDERMERE, FL$2,299,000
4.09 miles away
- 1244 WATER MAPLE DRIVE
OAKLAND, FL$2,295,000
2.05 miles away
- 16689 BROADWATER AVENUE
WINTER GARDEN, FL$2,295,000
0.28 miles away
- 16828 VINCI WAY
MONTVERDE, FL$2,260,000
4.16 miles away
- 5243 W LAKE BUTLER ROAD
WINDERMERE, FL$2,250,000
4.53 miles away
- 7346 JOHN HANCOCK DRIVE
WINTER GARDEN, FL$2,225,000
4.49 miles away

16086 JOHNS LAKE OVERLOOK DRIVE
WINTER GARDEN, FL
LIGHTBOX-IMAGES