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$300,000
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Property Description
Virtually Staged. Lowest Price per foot in Windsong at Leesburg! Seller will put on a NEW Roof prior to closing with accepted contract! Welcome to 5909 Windsong Oak Drive NEAR the quiet culdesac in the very back of this quiet community, in the desirable Windsong at Leesburg community-where modern comfort, convenience, and Florida living come together beautifully. This move-in-ready home offers 1,875 square feet of thoughtfully designed living space featuring attractive stone accents, durable block-and-stucco construction, energy-efficient double-pane windows, and a spacious two-car garage. Step through the impressive foyer and discover an open-concept floor plan highlighted by large ceramic tile flooring, abundant natural light, and spacious gathering areas perfect for entertaining or everyday living. The heart of the home is the oversized kitchen featuring rich espresso cabinetry, granite countertops, stainless steel appliances, abundant prep space, and a large dining area ideal for family dinners and holiday celebrations. The expansive living room flows seamlessly to the large covered lanai through oversized sliding glass doors, creating the perfect indoor-outdoor lifestyle. Whether you're enjoying your morning coffee, relaxing after work, or hosting friends and family, this inviting space is designed to be enjoyed year-round. The oversized primary suite serves as a private retreat with plenty of room for a sitting area, a huge walk-in closet, and a luxurious ensuite bath featuring dual vanities, solid-surface countertops, a soaking tub, and a separate walk-in shower. Secondary bedrooms are with comfort and privacy, while the oversized laundry room provides additional storage and functionality. Beyond the home itself, Windsong at Leesburg offers exceptional community amenities with low HOA fees. Residents enjoy a beautiful community pool, covered seating and gathering areas, and a playground, creating the perfect setting for relaxation, recreation, and neighborhood gatherings. Location is another standout feature. Conveniently situated near Publix, shopping, restaurants, medical facilities, and daily conveniences, everything you need is just minutes away. Outdoor enthusiasts will appreciate the close proximity to public boat ramps and the area's beautiful lakes, providing endless opportunities for boating, fishing, kayaking, and waterfront fun. Commuters will love the easy drive to Clermont, Minneola, and surrounding Central Florida destinations, while wine enthusiasts can enjoy nearby weekends at Lakeridge Winery, one of Florida's premier wineries known for its scenic vineyards, festivals, and live entertainment. If you've been searching for a move-in-ready home in Leesburg with granite countertops, stainless steel appliances, an oversized primary suite, covered lanai, low HOA fees, community pool, playground, and convenient access to shopping, boating, and Clermont, then 5909 Windsong Oak Drive is the opportunity you've been waiting for. Schedule your private showing today and discover why this exceptional home stands out from the competition.
Full Property Details
Full Property Details for 5909 Windsong Oak Dr
General
- Price: $300,000
- HOA FEE: $86/month
- HOA FEE FREQ.: Quarterly
- Taxes: $3,578 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6411614
- Updated: 6/26/2026
- Added to Site: 47 day(s) ago
Rental Information
- Min. Lease: 7 Months
Interior
- Number of Rooms: 6
- Interior Features: Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
- Appliances: Dishwasher, Disposal, Microwave, Refrigerator
- Furnishings: Unfurnished
- Flooring: Carpet, Ceramic Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room
Exterior
- Exterior Features: Irrigation System, Sidewalk, Sliding Doors
- Deck/Patio: Covered, Rear Porch
- Porch/Patio/Deck: Covered, Rear Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 34748 - Leesburg
- County: Lake
- Development Name: 34748 - Leesburg
- Subdivision: WINDSONG AT LEESBURG
- Driving Directions: US HWY 27 north to Leesburg to Windsong Oak Dr. home on left at back of community.
- Direction Faces: East
School Information
- Elementary School: Leesburg Elementary
- Middle School: Oak Park Middle
- High School: Leesburg High
Community
- Community Name: 34748 - Leesburg
- Community Features: Community Mailbox, Playground, Pool
- Association: Yes
- Assoc. Name: Dave Ellis
- Assoc. Fees Include: Community Pool
- Pet Restrictions: SEE HOA Bylaws and Leesburg rules/regs
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Electricity Connected, Sewer Connected, Street Lights
Structural Information
- Architectural Info: Traditional
- Architectural Style: Traditional
- Exterior Const.: Block
- Roof: Shingle
- Stories/Levels: One
- Square Feet: 1,875
- Sq. Ft. Source: Public Records
- Year Built: 2013
Lot Features
- Lot Size (Acres): 0.14
- Lot Size (Sq. Ft.): 6,226
- Lot Size: 6226
- Frontage: Street Dead-End, Street Paved
- Street/Road Desc.: Paved, Asphalt
Green Features
- Indoor Air Quality: Ventilation
Financial Considerations
- Association Fee: $258
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $3,578
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WINDSONG AT LEESBURG PB 57 PG 36-39 LOT 85 ORB 5709 PG 1474
- Flood Zone Info: X
- APN: 242024230000008500
- Property ID: 242024230000008500
Listed by Nexthome Lott Premier Realty
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Schools
Schools serving 5909 Windsong Oak Dr
School District:Lake County School District
| Name | Grades | Distance |
|---|---|---|
Leesburg Elementary School 2229 South Street, Leesburg, FL 34748 | PK-5 | 5.7 mi |
Oak Park Middle School 2101 South Street, Leesburg, FL 34748 | 6-8 | 5.7 mi |
Leesburg High School 1401 Yellow Jacket Way, Leesburg, FL 34748 | 9-12 | 5.9 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 5909 Windsong Oak Dr
Date
Details
Price
Change
Source
6/26/2026
Price Reduced
$300,000
-1.64%
MLS
6/18/2026
Price Reduced
$305,000
-3.17%
MLS
6/02/2026
Price Increased
$315,000
9%
MLS
5/30/2026
Listed
$289,000
21.43%
MLS
4/21/2021
Sold
$238,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 5909 Windsong Oak Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,643
2%
$266,210
3%
2024
$3,555
—
$258,710
3%
2024
$3,555
4%
$251,420
3%
2023
$3,406
—
$244,100
3%
2022
$3,397
5%
$236,996
26%
2021
$3,237
17%
$187,970
25%
2018
$2,773
8%
$150,303
9%
2017
$2,557
-2%
$137,821
—
2016
$2,597
1%
$137,821
4%
2015
$2,566
-15%
$132,318
-18%
2019
$3,006
25%
$160,717
24%
2014
$2,399
976%
$130,041
970%
2013
$223
—
$12,150
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 5909 Windsong Oak Dr
5909 Windsong Oak Drive, Leesburg, FL 34748 (MLS# O6411614) is a Single Family property with 3 bedrooms and 2 full bathrooms. 5909 Windsong Oak Drive is currently listed for $300,000 and was received on May 30, 2026. Want to learn more about 5909 Windsong Oak Drive? Do you have questions about finding other Single Family real estate for sale in Leesburg? You can browse all Leesburg real estate or contact a Coldwell Banker agent to request more information.

