17737 DEER ISLE CIRCLE Winter Garden, FL $ 2,950,000
17737 DEER ISLE CIRCLE
$ 2,950,000
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17737 DEER ISLE CIRCLE

Winter Garden, FL, 34787
$ 2,950,000
Bedrooms5 Baths3.2 Sq 4,886

Monthly Estimate*

$ 18,164

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Single Family Home for sale in Winter Garden, FL

for $2,950,000 with 5 bedrooms and 3 full baths, 2 half baths. This 4,886 square foot home was built in 2015 on a lot size of 1.02.

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.

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Single Family Active

Price

$ 2,950,000

Bedrooms

5

Full Bath

3

Half Bath

2

Property Type

Single Family

Taxes

$ 24,540

Style

Mediterranean

Lot Size

1.02

Year Built

2015

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6381953

Features
General
Sewer Aerobic Septic Septic Tank
Heating Central Electric Zoned
Cooling Central Air Zoned
Utilities Cable Connected Electricity Connected Propane Sprinkler Well
Possession Close Of Escrow
Roof Tile
Appliances Built-In Oven Convection Oven Cooktop Dishwasher Disposal Electric Water Heater Exhaust Fan Freezer Microwave Refrigerator Tankless Water Heater Water Softener
Zoning P-D
HOA Fee 1240
Garage Spaces 3
Association Fee Includes Private Road
Patio/Porch Features Covered Screened
Architectural Style Mediterranean
Pool Features Chlorine Free In Ground Infinity Lighting Outside Bath Access Pool Alarm Salt Water Screen Enclosure Self Cleaning
Security Features Security System
Construction Materials Block Stucco Wood Frame
Pets Allowed Yes
Year Built 2015
View Water
Levels Two
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
Waterfront Features Lake Waterfront Lake Front
Community Features Community Boat Ramp Dock Lake Water Access Waterfront Deed Restrictions Gated Community - No Guard Tennis Court(s)
Assoc Fee Paid Per Semi-Annually
County Orange
New Construction false
Property Type Residential
Association Amenities Gated Pickleball Court(s)
Attached Garage true
Energy Efficient HVAC Lighting Thermostat Water Heater Windows
Subdivision Name DEER ISLAND
Facing Direction East
Garage Y/N true
Other Structures Outdoor Kitchen
Total Rooms 14
Full Baths 3
Status Active
Directions Turnpike exit 272 onto SR 50 towards Clermont Keep left on SR 50 (west) Turn left on Colonial Dr Turn left onto Deer Isle Drive right on Deer Isle Circle Home is on the right side
High School West Orange High
City WINTER GARDEN
Body of Water JOHN'S LAKE
Association Name Sentry Management
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Acres
Lot Size Square Feet 44593
Carport Y/N false
Listing Terms Cash Conventional VA Loan
Spa Features Heated In Ground
Elementary School Tildenville Elem
Land Lease Y/N false
Tax Annual Amount 24540
Middle/Junior High School Lakeview Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 11
Legal Description DEER ISLAND 15/63 LOT 11 & THAT PART OFOCCUPIED LAND LYING BETWEEN THE LOT ANDTHE ORDINARY HIGH WATER LINE OF JOHNS LAKE BOUNDED BY THE EXTENSIONS OF THE LOTLINES EXTENDED TO THE OHWL
Water View Lake
Water Access Type Lake
Minimum Lease 8-12 Months
Water Access Y/N true
Monthly HOA Amount 206.67
Additional Rooms Den/Library/Office Formal Dining Room Separate Formal Living Room Separate Great Room
Water View Y/N true
Flood Zone Code X
DockY/N true
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Interior
Interior Amenities Cathedral Ceiling(s) Ceiling Fan(s) Coffered Ceiling(s) Crown Molding Eating Space In Kitchen High Ceilings In Wall Pest System Kitchen/Family Room Combo Open Floorplan Primary Bedroom Main Floor Solid Surface Counters Split Bedroom Stone Counters Thermostat Tray Ceiling(s) Walk-In Closet(s) Window Treatments
Flooring Travertine Hardwood
Furnished Y/N Unfurnished
Fireplace Features Gas Living Room Outside
Air Conditioning Y/N true
Heating Y/N true
Window Features Double Pane Windows Insulated Windows Low-Emissivity Windows Shutters Thermal Windows Tinted Windows
Fireplace Y/N true
Half Baths 2
Laundry Features Electric Dryer Hookup Inside Laundry Room Washer Hookup
Total Bedrooms 5
Total Baths 5
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Exterior
Exterior Amenities Balcony Fire Pit Irrigation System Lighting Outdoor Grill Outdoor Kitchen Private Mailbox Rain Gutters Sliding Doors
Vegetation Mature Landscaping Trees/Landscaped
Parking Features Driveway Garage Door Opener Garage Faces Side
Lot Features Oversized Lot Sidewalk Sloped
Water Source Well
Lot Size Area 1.0237
Foundation Details Slab
Spa true
Building Area Total 7790
Lot Size Acres 1.02
Road Surface Type Paved Asphalt
Private Pool true
Waterfront Y/N true
Covered Spaces 3
Road Frontage Type Street Paved Private Road
Road Responsibility Private Maintained Road
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* Excluded Features
List By
Premier Sotheby's Intl. Realty

Broker

candace.cassidy@sothebysrealty.com

Email

Affordability Calculator

$20,209
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Monthly Principal & Interest
$18,164
Monthly Property Taxes
$2,045
Monthly Home Insurance
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
West Orange High High School High School
Pricing History
DatePricePrice ChangeDescription
2/25/2026$2,950,000 Listed Price

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17737 DEER ISLE CIRCLE, Winter Garden, FL, 34787 is a Single Family Home for sale at $2,950,000 with 4,886 sqft and a lot size of 1.02. 17737 DEER ISLE CIRCLE has 5 bedrooms, 3.2 baths, and was built in 2015. The property's zip code is 34787 which is in Winter Garden, FL