5909 WINDSONG OAK DRIVE, LEESBURG, FL, 34748
Active66 days on marketListed May 30, 2026MLS #O6411614
About this home
5909 WINDSONG OAK DRIVE
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.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,875
Sqft
0.14 ac
Lot size
2
Garage
2013
Year built
One
Levels
$159
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$2,437 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$2,437/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+1%
$/sqft vs Leesburg actives
$159 vs $171
Days on market
66 vs 56 typical
Where $159/sqft sits among the 400 Leesburg actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Leesburg
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Leesburg. See the full Leesburg guide →
LEESBURG 34748 — neighborhood snapshot
Population
45,960
Median age
60.4
Median income
$53,768
Median home value
$226,200
Avg household
2.14
Households w/ children
3,516
For the school run
Lake County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Leesburg market
$269K → $290K
Leesburg median sold, yr/yr
96.1%
Sale-to-list ratio (12 mo)
209 of 400
Leesburg actives have cut their price
Median sold price, Leesburg, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 7% above the LEESBURG 34748 median. See the full Leesburg market guide →
Paper trail
This home's history
Reality check
What actually sold near 5909 WINDSONG OAK DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jul ’26$305,000
26016 SINGING LARK COURT · same community
4 bd · 2 ba · 1,868 sqft · $163/sqft · 155 DOM
Sold · Oct ’25$339,400
5515 WINDSONG OAK DR · same community
4 bd · 2 ba · 1,749 sqft · $194/sqft · 108 DOM
Sold · Jul ’26$380,000
5712 BRISTLELEAF COURT · same community
4 bd · 2.5 ba · 2,600 sqft · $146/sqft · 117 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 5909 WINDSONG OAK DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5909 WINDSONG OAK DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
5909 WINDSONG OAK DRIVE FAQs
What would the monthly payment be for 5909 WINDSONG OAK DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,437/mo — principal and interest, the actual property-tax bill, the $86/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 5909 WINDSONG OAK DRIVE?+
The association fee works out to $86 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 5909 WINDSONG OAK DRIVE?+
The most recent tax bill on record (2025) was $3,578. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 5909 WINDSONG OAK DRIVE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Leesburg?+
At $299,000, this home is priced right at the Leesburg median.
Which schools are assigned to 5909 WINDSONG OAK DRIVE?+
Oak Park Middle School (middle), Leesburg Elementary School (elementary), Leesburg High School (high) — Lake County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of NEXTHOME LOTT PREMIER REALTY · Corey Lott. MLS #O6411614.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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