3 Beds ⋅ 2 Baths ⋅ Windsong At Leesburg SubDv. ⋅ 34748 Zip Code

$$PRICED TO SELL$$ HUGE LOT...O.28 OF AN ACRE!!!! COMMUNITY POOL AND PLAYGROUND. Welcome to 5516 Windsong Oak Drive, an exceptionally upgraded, light & bright 3-bedroom, 2-bath home featuring a huge 3-car garage, a 0.28-acre homesite, & a cozy covered back porch, perfect for morning coffee or evening relaxation. Built in 2020 by Hanover Family Builders, this home offers a rare combination of premium finishes, thoughtful upgrades, & long-term affordability. All appliances, including the washer and dryer, plus all window treatments, are included. The community also features a pool & playground just moments from your front door. Step inside and you'll immediately appreciate the spacious feel created by the 9-foot, 3-inch ceilings, abundant natural light, upgraded porcelain tile flooring throughout the main living areas & bathrooms, designer matte black hardware and fixtures, ceiling fans, stylish lighting with dimmers, and upgraded door hardware. This is far from a cookie-cutter home—every finish has been thoughtfully enhanced. The beautifully appointed kitchen serves as the heart of the home, featuring upgraded cherry cabinetry with 42-inch upper cabinets, elegant angled crown molding, convenient triple-drawer base cabinets, quartz countertops, a Kohler Vault K-15160-CP stainless steel double-basin apron-front sink, garbage disposal, three designer pendant lights, and a microwave vented directly to the exterior. A spacious center island with a breakfast bar overlooks the family room, creating an ideal layout for entertaining. Just beyond, the covered back porch extends your living space outdoors, making gatherings with family and friends effortless. The primary suite is a true retreat, enhanced with two additional windows that fill the room with natural light. The spa-inspired bathroom features a frameless glass shower, an upgraded Kohler electric push-button rainfall shower system, a private water closet, a matching triple-drawer vanity cabinet, a ceiling fan, and custom barn doors. The impressive 8-foot by 6-foot walk-in closet has been professionally customized with built-in shelving and storage, offering exceptional organization. The oversized, insulated 3-car garage is a standout feature, boasting 11-foot ceilings, a 200-amp electrical service upgrade—perfect for EV charging, welding, or a workshop—pre-wiring for the third bay, and a keypad-entry garage door opener. Additional upgrades include a spacious laundry room with a double-basin stainless steel utility sink, an upgraded Samsung washer and dryer with steam features, a whole-house water filtration system requiring no filter changes, and a water softener. The exterior of the home has also been freshly painted, and the upgraded paver driveway and front porch add beautiful curb appeal. The value extends well beyond the upgrades. This home offers an incredible 2.7% FHA transferable interest rate—ask for details. For additional peace of mind, the air conditioning system has been fully serviced with maintenance components replaced and includes a one-year Del-Air warranty. Outdoor enthusiasts will appreciate being just moments from the community's beautiful 30-acre nature preserve, while Pear Park, located less than a quarter mile away, offers hiking trails, pickleball courts, and a dog park. Conveniently located near The Villages, you'll enjoy easy access to premier shopping, dining, golf, and entertainment. A truly upgraded home in one of Lake County's most desirable communities.

5516 Windsong Oak Drive, Leesburg

$75,000

Windsong At Leesburg SubDv. ⋅ 34748 Zip Code

Build Your Dream Home in Windsong at Leesburg. Rare opportunity to own a residential lot in the sought-after community of Windsong at Leesburg. This 0.28-acre lot sits on a curve of Windsong Oak Drive, offering a cleared, ready-to-build canvas in an established neighborhood of attractive single-family homes. Windsong is a deed-restricted community with low quarterly HOA fees ($258/quarter) that cover the community pool with cabana, two playgrounds, covered outdoor gathering spaces, and common area maintenance. Keeping the neighborhood looking its best year-round. Situated in the heart of Lake County, you're just minutes from the scenic Harris Chain of Lakes, one of Florida's premier boating and fishing destinations. Nearby the waterfront beauty of Venetian Gardens Park on Lake Harris. Lake Griffin State Park, downtown Leesburg's shops and dining, and major medical facilities are all within easy reach. Orlando and its international airport are approximately 40 miles away. Whether you're planning to build now or hold as an investment, this lot checks every box.

5620 Windsong Oak Drive, Leesburg

$330,000

4 Beds ⋅ 3 Baths ⋅ Windsong At Leesburg SubDv. ⋅ 34748 Zip Code

Virtually Staged. Picture yourself at 5605 Windsong Oak Dr, a residence where everyday comfort and practical features converge. The kitchen contains all stainless steel appliances, complementing the primary bathroom's double sinks and soothing jacuzzi tub. An inviting covered patio extends the living space outdoors. Exceptional comfort and thoughtful details define this home.. Included 100-Day Home Warranty with buyer activation

5605 Windsong Oak Drive, Leesburg

$299,000

3 Beds ⋅ 2 Baths ⋅ Windsong At Leesburg SubDv. ⋅ 34748 Zip Code

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.

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 1,700 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 1,700 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 5 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 September 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Windsong at Leesburg

$329,400Median sale price

$146Median per square foot

108 daysMedian days to contract

5Homes sold in 12 months

Sale prices ran from $305,000 to $400,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

Homes priced right sold far faster

Median days to go under contract. Shorter is better.

Never reduced 1 sales, closed at 103.8% of asking6 days

Reduced at least once 4 sales, closed at 100% of the reduced price112 days

Sellers who priced correctly and held their number went under contract in a median 6 days. Sellers who had to reduce took 112 days and still closed at 100% of their already reduced price, after a typical cut of $19,955. Opening high costs time and money, in that order.

Seller concessions

80%Of sales included a seller credit

$12,000Typical credit when there was one

4 of 5Sales 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

VA 2 sales40%

FHA 2 sales40%

Conventional 1 sales20%

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 17 September 2025 through 12 September 2026, refreshed monthly and current as of September 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.