Under contract-accepting backup offers. Welcome home! This turnkey, exquisite custom home enables you to wake up to shimmering water views of Johns Lake and step into the lakefront lifestyle you’ve been dreaming of. On an acre in a gated community, sellers spared no expense on a complete renovation— exterior to interior and down to the studs. New windows, high end finishes, and designer details in every room rival new construction. Upon entering, you’ll be captivated by an abundance of natural light, soaring ceilings and panoramic water views. The foyer leads to the spacious living/office/flex space and dining room with stunning dry bar and 180+ bottle wine fridge. The large family room with fireplace feature wall and bay window adjoins the true gourmet kitchen for open concept living, overlooking the lake and community pond with lighted fountain. A chef’s kitchen features tall kitchen cabinets for extra storage, massive center island, large sink, Fisher and Paykel double-drawer dishwasher, Scotsman pellet icemaker. The all Viking appliance pkg includes a 36” refrigerator with 30” freezer, dbl ovens, warming drawer, 6 burner induction stove top. A plumbed, built-in Miele espresso machine provides your favorite morning coffee, hot water, and more. A reverse osmosis water filtration system feeds the kitchen sink, icemakers, coffee machine. The sunroom boasts two walls of new Pella hurricane rated slider doors that flood the home with natural light and frame the stunning waterfront scenery and provides a seamless connection between indoor and outdoor living opening onto the sandstone lanai with oversized resort style sparkling saltwater pool, spa and waterfall. The lanai roof structure is unique in that the vaulted roof and screening provides all weather protection to the pool, built in bar and overflow patio area allowing for entertaining in any weather or watching the Disney fireworks or rocket launches. The lanai is outfitted with 3 large DC ceiling fans and integrated watering system. Spacious primary bedroom with lanai access overlooks the lake and boasts a spa-like bathroom with dual vanities, frameless zero entry shower, free-standing tub and large walk-in closet. The split bedroom plan allows for maximum privacy. Secondary bedrooms are spacious with oversized closets. The exterior, with its professional landscape design and lighting, is designed for play, relaxation and beauty. Enjoy direct access to Johns Lake and spend your days boating, jet skiing, kayaking, paddle boarding, fishing or simply relaxing. A paver walkway from the house leads to the expansive back yard, beachfront, and large fire pit area, perfect for play and entertaining. Private dock with remote boat lift and double jet ski lift allows for lake enjoyment with effortless access. Dock is equipped with running water, lights and no/low maintenance composite decking and handrails. The deep garage is oversized with storage racks and an additional air-conditioned bonus space to be used as a craft/exercise room/home office or air-conditioned storage. Neighborhood amenities include community dock, boat ramp, tennis/pickleball court, basketball court, cable/internet. Conveniently and centrally located with easy access to the Turnpike, 429, 408, downtown Winter Garden and Orlando, the airport, Disney, Universal and area attractions. Minutes to restaurants, shops, hospitals, West Orange Trail.
Property Details
Price:
$1,495,000
MLS #:
O6440044
Status:
Active Under Contract
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
DEER ISLAND
Neighborhood:
34787wintergardenoakland
Listed Date:
Sep 14, 2026
Finished Sq Ft:
2,735
Total Sq Ft:
5,123
Lot Size:
42,004 sqft / 0.96 acres (approx)
Year Built:
1988
See this Listing
Schools
Elementary School:
Tildenville Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Ice Maker, Kitchen Reverse Osmosis System, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Ceramic Tile
Heating
Central, Electric
Interior Features
Built-in Features, Ceiling Fan(s), Dry Bar, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Architectural Style
Traditional
Association Amenities
Basketball Court, Cable TV, Gated, Pickleball Court(s), Tennis Court(s)
Attached Garage YN
1
Community Features
Community Boat Ramp, Dock, Lake, Waterfront, Deed Restrictions, Gated Community – No Guard, Golf Carts OK, Sidewalks, Tennis Court(s)
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
West
Exterior Features
Fire Pit, Irrigation System, Lighting, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors, Storage
Garage Spaces
2
Lot Features
Landscaped, Level, Oversized Lot, Sidewalk, Unincorporated
Open Parking YN
1
Other Structures
Boat House, Storage
Parking Features
Driveway, Garage Door Opener, Garage Faces Side, Ground Level, Oversized, Workshop in Garage
Patio And Porch Features
Covered, Front Porch, Patio, Screened
Roof
Shingle
Security Features
Gated Community
Spa Features
Heated, In Ground
View
Water
Waterfront Features
Lake, Waterfront, Lake Front, Lake – Chain of Lakes
Window Features
Double Pane Windows
Financial
HOA Fee
$1,481
HOA Fee Frequency
Semi-Annually
HOA Includes
Cable TV, Common Area Taxes, Escrow Reserves Fund, Internet, Private Road
HOA Name
Sentry Management
HOA Phone
352-243-4595
Tax Year
2025
Taxes
$7,930
Map
Community
- Address263 DEER ISLE DRIVE WINTER GARDEN FL
- SubdivisionDEER ISLAND
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Oct 18, 2026
806
Single Family Listed
119
Avg DOM
278
Avg $ / SqFt
$744,002
Avg List Price
Property Summary
- Located in the DEER ISLAND subdivision, 263 DEER ISLE DRIVE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $1,495,000 and features 3 beds, 3 baths, and has approximately 2,735 square feet of living space, and was originally constructed in 1988. The current price per square foot is $547. The average price per square foot for Single Family listings in WINTER GARDEN is $278. The average listing price for Single Family in WINTER GARDEN is $744,002. To schedule a showing of MLS#o6440044 at 263 DEER ISLE DRIVE in WINTER GARDEN, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
Similar Listings Nearby
Courtesy of BHHS FLORIDA REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 263 DEER ISLE DRIVE
WINTER GARDEN, FL
