Location: Windsong At Leesburg, Leesburg
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5909 WINDSONG OAK DR, LEESBURG, FL 34748
$289,000Listed 05/30/2026 7:56AM MLS ID: O6411614
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1875 Built: 2013Monthly Fee: $86 Tax: $3,578 (2025)Community: Windsong At LeesburgSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,578
Elementary School: Leesburg Elementary
High School: Leesburg High
Tax Year: 2025
Middle School: Oak Park Middle
Remarks: One or more photo(s) has been virtually staged. 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.
Listing is courtesy of: NEXTHOME LOTT PREMIER REALTY (407-222-0495)
Listing Agent: Corey Lott (407-222-0495)
26143 FEATHERGRASS CIR, LEESBURG, FL 34748
$349,9001 Day on yellowkey MLS ID: G5112508
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2215 Built: 2022Monthly Fee: $80 Tax: $4,424 (2025)Community: Windsong At LeesburgSingle Family
Taxes:$4,424
Remarks: Welcome home to this spacious home located in the Windsong community of Leesburg. Designed with an open layout, the kitchen features a center island overlooking the dining and living areas, creating a comfortable space for everyday living and entertaining. The owner’s suite offers a private bath with dual sinks, a large walk-in shower, and a roomy walk-in closet. Upstairs, the loft provides additional flexible living space that works well for a game room, media area, office, or relaxing area. Additional features include stainless steel appliances, solid surface countertops, and tile flooring in the wet areas. Windsong offers residents a fabulous location and setting with opportunities to enjoy the outdoors, along with community amenities including recreation areas, a tot lot, and dog park. Conveniently located off Highway 27, the community is just minutes from shopping, dining, and entertainment in historic downtown Leesburg and an easy commute to the interstate and turnpike.
Listing is courtesy of: MORRIS REALTY AND INVESTMENTS (352-435-4663)
Listing Agent: Lena Williams (352-435-4663)
5712 BRISTLELEAF CT, LEESBURG, FL 34748
$379,990106 Days on yellowkey MLS ID: G5107689
REDUCED by $4,910 (1.3%) on 05/12/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2600 Built: 2023Monthly Fee: $80 Tax: $5,449 (2025)Community: Windsong At LeesburgSingle Family
Taxes:$5,449
Remarks: Welcome HOME! This spacious 2023 built home is located in the beautiful community of Windsong—with a fabulous location. You have close access to both the interstate and turnpike for easy travel. This beauty has all of the modern living benefits and being so new, you will have plenty of peace of mind knowing your major home repairs will be minimal! This beautifully upgraded 4-bedroom, 2.5-bath home features a well thought floorplan with flexible living spaces and energy-efficient features throughout. Your main living and entertaining will be done downstairs with the spacious open kitchen, family room, flex room, and half bath... all flowing and open to each other nicely. The bright, modern kitchen features shaker-style cabinetry, quartz countertops, and stainless-steel appliances, making it perfect for everyday living and entertaining. The flex room off the foyer provides endless possibilities—home office, playroom, or formal sitting area. The first floor also features a spacious family room, dining area for memorable meals, and a patio ideal for outdoor living. Upstairs, a grand loft creates additional shared living space while all of your private bedrooms are upstairs as well. The Owner’s Suite includes a luxurious en-suite bath with dual sinks, a large walk-in shower, and a spacious walk-in closet. Three additional bedrooms and a convenient utility room with top-of-the-line washer and dryer complete the second level. Enjoy outdoor gatherings in the fully fenced backyard featuring a vinyl privacy fence and extended patio—perfect for hosting family and friends.
26016 SINGING LARK CT, LEESBURG, FL 34748
$326,500141 Days on yellowkey MLS ID: TB8461364
REDUCED by $3,400 (1.0%) on 05/14/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1868 Built: 2008Monthly Fee: $86 Tax: $1,725 (2025)Community: Windsong At LeesburgSingle Family
Taxes:$1,725
Remarks: ***PRICE REDUCTION*** Turnkey 4 Bedroom | 2 Bath | Metal Frame Construction | Roof 2022 Charming, solidly built, and thoughtfully refreshed, this 4-bedroom, 2-bath home offers strength, style, and comfort in one beautifully maintained package. Constructed with durable metal 2x4 framing throughout, this home provides lasting structural integrity and peace of mind. A new roof (2022) adds additional confidence for years to come. Inside, you’ll find fresh paint throughout and four brand-new, never-used kitchen appliances, creating a clean and modern feel. Strategically placed SolaTubes bring in abundant natural light — 12” tubes brighten the hallway and bathrooms, while an impressive 18” SolaTube fills the kitchen with daylight during meal preparation. The main bathroom features a relaxing Jacuzzi tub with full tile surround, creating a spa-like retreat. The second bathroom includes a double sink for added convenience. Updated faucets, showerhead, and hardware provide fresh finishing touches. ClosetMaid adjustable systems throughout closets, pantry, and laundry room maximize organization and functionality. Additional Features: • Full paver driveway • Glassed-in rear porch • Separate grilling patio • Surround sound speakers in main bedroom and family room • Nest & Alexa compatible WiFi/Bluetooth thermostat • Wired for whole-house alarm system • Whole-house water filtration system • Privacy-fenced yard • Peach and loquat trees • Blueberries, blackberries, and Barbados cherry bushes This home offers the rare combination of durable construction, thoughtful upgrades, and effortless move-in readiness. Simply unlock the door and begin your next chapter. Schedule your private walkthrough today.
Listing is courtesy of: LUXE PROPERTIES (305-809-7650)
Listing Agent: Cara Hagan (305-809-7650)
5511 BRAKEN FERN WAY, LEESBURG, FL 34748
$379,00071 Days on yellowkey MLS ID: TB8480432
Bed: 6 Bath: 3.0 Liv Area Sq Ft: 2580 Built: 2023Community: Windsong At LeesburgSingle Family
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: FOR SALE: 6BR Home with Incredible Backyard Oasis Windsong Oak Community $379,000 Rare opportunity to own a spacious 6-bedroom, 3-bath home with an open floor plan and an outdoor space that truly stands out. Inside features: Open, airy layout Large master suite with private bath Upstairs jack-and-jill bathroom Full bedroom + bath downstairs (great for guests or office) Outdoor oasis includes: Entertaining deck Peaceful koi pond Grassy play area or future fire-pit space Raised garden beds Plenty of room to relax or host Homes with this much space and outdoor living don’t come up often.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
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