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$935,000
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Property Description
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!
Full Property Details
Full Property Details for 744 Lake Brim Dr
General
- Sold For: $935,000
- HOA FEE: $208/month
- HOA FEE FREQ.: Quarterly
- Taxes: $9,275 (2025)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6388775
- Added to Site: 133 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 11
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Open Floorplan, Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)
- Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Carpet, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside
Additional Information
- Shared Amenities: Clubhouse, Park, Playground, Pool, Trail(s)
Exterior
- Exterior Features: Fire Pit, French Doors, Irrigation System, Outdoor Grill, Outdoor Kitchen
- Deck/Patio: Covered, Front Porch, Rear Porch, Screened, Wrap Around
- Porch/Patio/Deck: Covered, Front Porch, Rear Porch, Screened, Wrap Aroun
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Alley Access, Driveway, Garage Faces Rear
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: OAKLAND PARK
- Driving Directions: From Windermere, head west on Highway 50. Turn right onto Avalon Road, left onto Oakland Ave. The community is on the right-turn right onto Oakland Park Blvd, then left onto Lake Brim Dr. Pass over the West Orange Trail. The home is on your left facing the park.
- Direction Faces: East
School Information
- Elementary School: Tildenville Elem
- Middle School: Lakeview Middle
- High School: West Orange High
Community
- Community Name: 34787 - Winter Garden/Oakland
- Community Features: Waterfront, Dog Park, Golf Carts OK, Park, Playground, Pool
- Optional Amenities: Clubhouse, Park, Playground, Pool, Trail(s)
- Association: Yes
- Assoc. Name: LeLand Management/Erin Lewis
- Assoc. Fees Include: Community Pool
- Pet Restrictions: Buyer to verify with HOA
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable Connected, Natural Gas Connected, Public
Structural Information
- Exterior Const.: Block, Cement Siding, Wood Frame
- Roof: Shingle
- Windows: Blinds
- Stories/Levels: Two
- Square Feet: 2,667
- Sq. Ft. Source: Public Records
- Living Area: 2,667 Sq. Ft.
- Year Built: 2016
Additional Structures
- Other Structures: Outdoor Kitchen
Lot Features
- Property View: Park/Greenbelt, Trees/Woods
- Lot Size (Acres): 0.15
- Lot Size (Sq. Ft.): 6,492
- Lot Size: 6492
- Frontage: Street Paved
- Street/Road Desc.: Paved, Concrete
- Fencing (Description): Vinyl
Water Features
- Water Front Desc.: Waterfront
Financial Considerations
- Association Fee: $625
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $9,275
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: OAKLAND PARK UNIT 4A 87/105 LOT 282
- Flood Zone Info: X
- APN: 212227609802820
- Property ID: 212227609802820
Listed by Bhhs Florida Realty
Sold by Fannie Hillman & Associates
Get Pre-Approved Today
Schools
Schools serving 744 Lake Brim Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Tildenville Elementary School 1221 Brick Road, Winter Garden, FL 34787 | PK-5 | 0.3 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 0.6 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 3.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 744 Lake Brim Dr
Date
Details
Price
Change
Source
6/30/2026
Sold
$935,000
-1.48%
MLS
5/22/2026
Price Reduced
$949,000
-2.06%
MLS
4/24/2026
Price Reduced
$969,000
-2.61%
MLS
3/10/2026
Listed
$995,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
744 Lake Brim Drive, Winter Garden, FL 34787 (MLS# O6388775) is a Single Family property that was sold at $935,000 on June 30, 2026. Want to learn more about 744 Lake Brim Drive? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

