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Overview

3 bd2 ba1,875 sqft2 car garageSingle Family
TypeSingle Family
HOA$258/qtr
Built2013
Lot6,226 sqft
Living area1,875 sqft
Price / sqft$157
Garage2 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Solid Wood CabinetsSplit BedroomStone CountersThermostatWalk-in Closet(s)SidewalkCommunity MailboxPlayground

5909 Windsong Oak Dr is a 2013-built home in Windsong At Leesburg, Leesburg. Inside you'll find 3 bedrooms, 2 bathrooms, and 1,875 square feet of living space. Listed at $295,000 (about $157/sqft), 141 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $258 quarterly.

From the listing

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.

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The essentials

Built
2013
Price / sqft
$157
On market
141 days
Annual tax
$3,578
HOA
$258/qtr
Flood zone
X · Low risk
Lot
6,226 sqft
Type
Single Family Residence

At a glance

Single family
Built 2013
Community pool
Shared amenity
2 car garage
6,226 sqft lot
Lot size
1,875 sqft
Living area

Payment

Est. monthly payment
$2,071/mo
Down payment (20%)
$59,000
Property taxes
$298/mo
HOA
$258/qtr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
2013
Lot
6,226 sqft
Cooling
Central Air
Heating
Central
Parking
-
Days on Market
141
Solid Wood Cabinets
Split Bedroom
Stone Counters
Thermostat
Walk-in Closet(s)
Sidewalk
Community Mailbox
Playground
Pool
Street Lights
Dishwasher
Disposal
Microwave
Refrigerator
Elementary
Leesburg Elementary
Middle
Oak Park Middle
High
Leesburg High

Districts can re-zone, so verify directly with the district before relying on these.

Homestead exemption on file Flood Zone X
Annual Tax (2025)
$3,578
Parcel #
24-20-24-2300-000-08500

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Windsong At Leesburg
County
Lake
MLS Area
34748 - Leesburg
Lot Size
6,226 sqft
ClearedSidewalkStreet Dead-EndPaved
HOA
$258/qtr
Dave Ellis

Price history

Date
Event
Price
10/7/2026
Price change
Source: Stellar MLS #O6411614
$295,000-1.3%
$157/sqft
-
Price change
Source: Stellar MLS #O6411614
$299,000+3.5%
$159/sqft
5/30/2026
Listed for sale
Source: Stellar MLS #O6411614
$289,000
$154/sqft

Neighborhood

5909 Windsong Oak Dr
Leesburg, FL, 34748 · 34748 - Leesburg

Market insights

Offer Insights

Choose an offer strength

List price: $295,000
$290,000 – $295,000
98.5% – 100% of listTops out right at the list price
80% of listList price
200 of the last 396 home closings in 34748 landed at this number or higher (51%). The median one sat 50 days before it went under contract, and this one is on day 141.

Sample: 396 closed home sales in 34748 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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Calculator

Est. monthly payment
$2,070/mo
Principal & interest$1,539
Property taxes$298
Insurance$148
HOA$86
Down payment20% · $59,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA includes any condo dues reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$295,000

$157 per sq ft

Beds and baths

3 beds, 2 baths

Size

1,875 sq ft

Time on market

141 days

Year built

2013

Monthly payment

About $2,071/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $3,578 annual tax bill, insurance, and the $258/qtr HOA fee.

HOA fee

$258/qtr

Managed by Dave Ellis.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

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Have another question?

Brokered byNEXTHOME LOTT PREMIER REALTYListing agent: Corey LottListing data from Stellar MLS, MLS# O6411614.

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