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5909 Windsong Oak Drive, Leesburg
$295,000
3 Beds ⋅ 2 Baths ⋅ Windsong At Leesburg SubDv. ⋅ 34748 Zip Code
One or more photo(s) has been virtually staged. Lowest Price per foot in Windsong at Leesburg! Welcome to 5909 Windsong Oak Drive NEAR the quiet cul-de-sac in the very back of this quiet community, in the desirable Windsong at Leesburg Subdivision—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 great 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.

5909 Windsong Oak Drive, Leesburg

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Lake County › Leesburg › Windsong at Leesburg

Windsong at Leesburg, Leesburg

Windsong at Leesburg is a neighborhood in south Leesburg, in the 34748 zip code, built mostly in the 2000s. Homes are block and stucco, predominantly single story. Most homes fall between about 1,600 and 2,900 square feet under air, the median lot is roughly a fifth of an acre, and a two car garage is standard.

Homes here carry an HOA, billed quarterly, typically around $235. Confirm the figure on a specific parcel before relying on it.

What the homes are

  • Built Mostly built in the 2000s, with homes from 2005 to 2023.
  • Construction Block and stucco. Shingle roofs are near universal.
  • Size Most homes fall between about 1,600 and 2,900 square feet under air.
  • Bedrooms Four bedrooms is the most common plan, then three, then five.
  • Garage A two car garage is standard.
  • Lot The median lot is roughly a fifth of an acre.
  • HOA Billed quarterly, typically around $235. Confirm on a specific parcel before relying on it.

This page tracks what homes in Windsong at Leesburg actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 9 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated October 2026.

What homes sold for in Windsong at Leesburg

$315,150Median sale price
$163Median per square foot
73 daysMedian days to contract
9Homes sold in 12 months

Sale prices ran from $292,800 to $400,000.

By size

Home sizeSalesMedian priceMedian $/sq ftMedian days
Under 2,000 sq ft5$312,000$18544 days
2,000 to 3,000 sq ft3$323,000$14394 days

Larger homes usually show a lower price per square foot. That is normal and it is why a price per foot taken from the whole neighborhood should never be applied straight to one house.

Price cuts and time to contract

Median days to go under contract. Shorter is better.

Never reduced 3 sales, closed at 97.8% of asking14 days
Reduced at least once 6 sales, closed at 100% of the reduced price86 days

Sellers who held their number went under contract in a median 14 days. Sellers who had to reduce took 86 days and closed at 100% of their already reduced price, after a typical cut of $22,450.

Seller concessions

67%Of sales included a seller credit
$10,750Typical credit when there was one
6 of 9Sales carrying a credit

A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.

How buyers paid

Conventional 5 sales56%
FHA 2 sales22%
VA 2 sales22%

Cash was 0% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Windsong at Leesburg, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Windsong at Leesburg in Leesburg, Lake County, covering closed sales from 31 October 2025 through 26 October 2026, refreshed monthly and current as of October 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.

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