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744 LAKE BRIM DRIVE
WINTER GARDEN, FL, 34787
$995,000
4 Beds
3.5 Baths
2,667 SqFt
0.15 Acres
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MLS #O6388775 image #0
Perfectly positioned fronting one of Oakland Park’s picturesque green spaces, this exceptional home offers a rare opportunity to enjoy PARK-SIDE living in one of Winter Garden’s most celebrated communities. Oakland Park, a PARADE of HOMES award-winning neighborhood, is admired for its timeless architecture & inviting outdoor spaces that create a true sense of community. This beautifully designed Seaside floorplan blends classic charm with modern livability, offering 4 bedrooms, 3.5 baths, a STUDY, dining area, spacious loft, oversized garage, & FENCED yard. The primary suite is conveniently located on the main level, creating a peaceful retreat complete with a generous walk-in closet, a separate linen closet, & direct access to the laundry room, which has been enhanced with custom cabinetry for optimal storage & organization. Upstairs, the loft provides a versatile secondary living area—ideal for a media room or play space—accompanied by three additional bedrooms & two full baths, including one private en-suite. At the center of the home, the expansive kitchen is designed for both everyday living & effortless entertaining, enhanced with under cabinet lighting & tile backsplash. Abundant cabinetry & extensive counter space provide exceptional functionality, while the large island offers ample seating, making it the natural gathering place for family & guests alike. The adjoining dining area is equally impressive, featuring a dedicated buffet—perfect for hosting celebrations, holidays, or casual dinners. The home showcases rich WOOD flooring throughout the main living areas, adding warmth and sophistication, while soft carpeting in the bedrooms enhances comfort & tranquility. One of the home’s most captivating features is the inviting wraparound front porch, where French doors open to sweeping views of the beautifully maintained park. The home’s outdoor living continues in the screened rear porch, thoughtfully designed with retractable screens to maximize comfort & flexibility throughout the seasons. Beyond the porch, the backyard has been carefully curated as a private entertainment retreat. A paver patio anchors the space, complemented by a cozy FIRE-PIT, additional seating areas, & an outdoor kitchen featuring a built-in grill, mini fridge, & sink. Pet lovers will appreciate the dedicated dog area finished with low-maintenance artificial turf, creating a convenient & attractive space for four-legged family members. With its prime park-front location, versatile living spaces, & thoughtfully designed indoor-outdoor lifestyle, this home offers an exceptional blend of elegance, comfort, & community. Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!

Property Details

Price:
$995,000
MLS #:
O6388775
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OAKLAND PARK
Neighborhood:
34787wintergardenoakland
Listed Date:
Mar 10, 2026
Finished Sq Ft:
2,667
Total Sq Ft:
3,948
Lot Size:
6,492 sqft / 0.15 acres (approx)
Year Built:
2016
PoolPrimary Bedroom Main Floor34787 – Winter Garden/oakland34787wintergardenoaklandOakland ParkTildenville ElemLakeview MiddleWest Orange HighBuyer To Verify With Hoa8-12 MonthsPets Allowed

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Schools

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

Interior

Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Tile, Hardwood
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, Open Floorplan, Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)
Laundry Features
Inside
Levels
Two

Exterior

Association Amenities
Clubhouse, Park, Playground, Pool, Trail(s)
Attached Garage YN
1
Community Features
Waterfront, Dog Park, Golf Carts OK, Park, Playground, Pool
Construction Materials
Block, Cement Siding, Wood Frame
Covered Spaces
2
Direction Faces
East
Exterior Features
Fire Pit, French Doors, Irrigation System, Outdoor Grill, Outdoor Kitchen
Fencing
Vinyl
Garage Spaces
2
Lot Features
Sidewalk
Open Parking YN
1
Other Structures
Outdoor Kitchen
Parking Features
Alley Access, Driveway, Garage Faces Rear
Patio And Porch Features
Covered, Front Porch, Rear Porch, Screened, Wrap Around
Roof
Shingle
View
Park/Greenbelt, Trees/Woods
Waterfront Features
Waterfront
Window Features
Blinds

Financial

HOA Fee
$608
HOA Fee Frequency
Quarterly
HOA Includes
Community Pool
HOA Name
LeLand Management/Erin Lewis
HOA Phone
407-409-8594
Tax Year
2025
Taxes
$9,275

Map

Community

Subdivisions in WINTER GARDEN

Market Summary

Current real estate data for Single Family in WINTER GARDEN as of Apr 23, 2026
778
Single Family Listed
109
Avg DOM
282
Avg $ / SqFt
$749,117
Avg List Price

Property Summary

    Located in the OAKLAND PARK subdivision, 744 LAKE BRIM DRIVE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $995,000 and features 4 beds, 4 baths, and has approximately 2,667 square feet of living space, and was originally constructed in 2016. The current price per square foot is $373. The average price per square foot for Single Family listings in WINTER GARDEN is $282. The average listing price for Single Family in WINTER GARDEN is $749,117. To schedule a showing of MLS#o6388775 at 744 LAKE BRIM DRIVE in WINTER GARDEN, FL, contact your Preferred Real Estate Brokers agent at 4076987254.

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744 LAKE BRIM DRIVE
WINTER GARDEN, FL