17737 DEER ISLE CIRCLE WINTER GARDEN FL 34787 MLS #O6381953

17737 DEER ISLE CIRCLE
WINTER GARDEN, FL, 34787
$2,950,000
5 Beds
4 Baths
4,886 SqFt
1.02 Acres
Add
MLS #O6381953 image #0
Experience over an acre of elevated direct sunset lakefront luxury living on the naturally spring-fed waters of John’s Lake. Offered publicly for the first time, this fully custom estate represents a rare convergence of beauty, privacy and enduring design. Nearly 5,000 square feet of interior living space unfold effortlessly into an additional 1,000 square feet of exceptionally well-appointed enclosed outdoor living, creating seamless indoor to outdoor living. Positioned within the private gated enclave of Deer Island and presented in impeccable condition since its 2015 construction, the home reflects meticulous care and pride of ownership. Thoughtfully designed for a life well lived by owners and guests alike, every detail was executed with intention. Arrival is elegant and memorable, welcomed by a central fountain and expansive motor court leading to an oversized three-car garage, while two bedrooms on the main level, including the primary and guest suite, provide comfort, privacy and effortless livability for generations. Designed for entertaining, walls of fully retractable sliding glass doors dissolve the boundary between indoors and out, allowing the living and great rooms to open to the terrace beyond. The covered outdoor lounge, finished with a wood-paneled ceiling, gas fireplace and fully equipped outdoor kitchen, extends daily living outdoors. The infinity pool and spa, framed by gas fire bowls, merge seamlessly with the lake view itself, while a dedicated pool access bath enhances convenience. Privately positioned to capture sweeping lake views, the primary suite opens directly to the lanai and features dual walk-in closets. Its bath is anchored by a freestanding copper soaking tub, hammered copper sinks set within custom vanities, and a full stone walk-in shower with multiple showerheads and built-in bench. The kitchen features custom wood cabinetry, oversized island, induction cooktop, separate built-in refrigerator and freezer, professional-grade appliances, and walk in pantry. Architectural details include travertine flooring, coffered and tray ceilings, refined millwork and wrought iron staircase. All closets feature custom built-ins. The second-floor media room may also serve as a spacious fifth bedroom with private balcony overlooking the lake. Beyond the terrace, tiered gardens descend toward the shoreline, where Four Seasons marble statuary is thoughtfully placed throughout the grounds, like a work of art set within the landscape. A private putting green, fire pit and manicured lawn enhance the setting. The composite dock includes dual lifts for boat and jet ski, water and electric service, and upper level sun deck positioned for sunset views. John’s Lake spans over 2,500 acres and is known for exceptional clarity, ideal for skiing, boating, water sports and fishing. Deer Island offers gated entry with waterside tennis, pickleball and basketball courts. The home is serviced by a private well. Less than one mile from the Florida Turnpike and 25 minutes to downtown Orlando. Contact for your private viewing.

Property Details

Price:
$2,950,000
MLS #:
O6381953
Status:
Active
Beds:
5
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
DEER ISLAND
Neighborhood:
34787wintergardenoakland
Listed Date:
Feb 25, 2026
Finished Sq Ft:
4,886
Total Sq Ft:
7,790
Lot Size:
44,593 sqft / 1.02 acres (approx)
Year Built:
2015
MediterraneanWaterfrontLakefrontPoolTennisPrimary Bedroom Main FloorCommunity Gated34787 – Winter Garden/oakland34787wintergardenoaklandDeer IslandTildenville ElemLakeview MiddleWest Orange HighJohn’s LakeWaterBuyer To Confirm Current Guidelines With Hoa8-12 MonthsPets Allowed

Ask a Question

See this Listing

Send
  

Schools

Elementary School:
Tildenville Elem
Middle School:
Lakeview Middle
High School:
West Orange High

Interior

Appliances
Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Exhaust Fan, Freezer, Microwave, Refrigerator, Tankless Water Heater, Water Softener
Bathrooms
3 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air, Zoned
Flooring
Travertine, Hardwood
Heating
Central, Electric, Zoned
Laundry Features
Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup

Exterior

Architectural Style
Mediterranean
Association Amenities
Gated, Pickleball Court(s)
Community Features
Community Boat Ramp, Dock, Lake, Water Access, Waterfront, Deed Restrictions, Gated Community – No Guard, Tennis Court(s)
Construction Materials
Block, Stucco, Wood Frame
Exterior Features
Balcony, Fire Pit, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors
Other Structures
Outdoor Kitchen
Parking Features
Driveway, Garage Door Opener, Garage Faces Side
Roof
Tile
Security Features
Security System

Financial

HOA Fee
$1,240
HOA Frequency
Semi-Annually
HOA Includes
Private Road
HOA Name
Sentry Management
Tax Year
2024
Taxes
$24,540

Map

Community

Subdivisions in WINTER GARDEN

Market Summary

Current real estate data for Single Family in WINTER GARDEN as of Mar 14, 2026
736
Single Family Listed
103
Avg DOM
281
Avg $ / SqFt
$760,327
Avg List Price

Property Summary

    Located in the DEER ISLAND subdivision, 17737 DEER ISLE CIRCLE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $2,950,000 and features 5 beds, 4 baths, and has approximately 4,886 square feet of living space, and was originally constructed in 2015. The current price per square foot is $604. The average price per square foot for Single Family listings in WINTER GARDEN is $281. The average listing price for Single Family in WINTER GARDEN is $760,327. To schedule a showing of MLS#o6381953 at 17737 DEER ISLE CIRCLE in WINTER GARDEN, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

Similar Listings Nearby

broker reciprocity
MLS# O6354264broker reciprocity
15746 PENDIO DR
MONTVERDE, FL

$3,700,000

3.0 miles away

broker reciprocity
MLS# O6364796broker reciprocity
510 BRILEY AVENUE
OAKLAND, FL

$3,575,000

1.8 miles away

broker reciprocity
MLS# G5101161broker reciprocity
16103 PENDIO DRIVE
MONTVERDE, FL

$3,448,000

2.3 miles away

broker reciprocity
MLS# G5098859broker reciprocity
10301 SAVANNAH RIDGE LANE
WINTER GARDEN, FL

$3,299,999

3.1 miles away

broker reciprocity
MLS# G5106408broker reciprocity
16118 PENDIO DRIVE
MONTVERDE, FL

$3,292,955

2.4 miles away

broker reciprocity
MLS# O6371219broker reciprocity
17710 BROAD STREET
MONTVERDE, FL

$3,150,000

4.6 miles away

17737 DEER ISLE CIRCLE
WINTER GARDEN, FL