Date
Details
Price
Change
Source
2/28/2026
Listed
$2,100
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/17
$2,100
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1/17
Property Description
AVAILABLE NOW! Beautiful 3-bedroom, 2-bath townhome available for rent in the heart of Winter Garden! This 1,180 sq. ft. home features brand-new windows, a new microwave, a brand new AC, new roof, a new sliding glass door, an updated electrical panel, offering comfort, efficiency, and peace of mind. FIRST FLOOR BEDROOM with ensuite bathroom, then remaining 2 bedrooms upstairs. The interior boasts bright, open living spaces with a functional layout ideal for everyday living and entertaining. Screen room is tiled with artificial turf in the fenced backyard. Enjoy a prime location just minutes from Historic Downtown Winter Garden, where you'll find the popular Plant Street Market, a weekly farmers market, boutique shopping, and local dining. Winter Garden offers a charming small-town atmosphere with convenient access to major highways and top-rated schools. Plus, you're just a short drive from Walt Disney World and other Central Florida attractions-making this an ideal place to call home.
Full Property Details
Full Property Details for 1009 Westside Dr
General
- Rent: $2,100
- Status: Active
- Type: Townhouse
- Source: MidFloridaRegionalMLS
- MLS ID: O6386529
- Updated: 2/28/2026
- Added to Site: 9 day(s) ago
Interior
- Number of Rooms: 1
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Thermostat
- Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Carpet, Laminate
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside
Additional Information
- Security/Safety: Smoke Detector(s)
Exterior
- Exterior Features: Lighting, Sidewalk, Sliding Doors
- Deck/Patio: Patio, Screened
- Porch/Patio/Deck: Patio, Screened
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: WESTSIDE TWNHMS
- Driving Directions: Turn right onto W Smith St, Turn left onto Dillard St, Continue straight as Dillard St becomes Winter Garden Vineland Rd (CR 535), Drive approximately 2.5–3 miles. Take the ramp onto SR-429 (Daniel Webster Western Beltway) toward your desired direction (north or south)
School Information
- Elementary School: SunRidge Elementary
- Middle School: SunRidge Middle
- High School: West Orange High
Community
- Community Name: 34787 - Winter Garden/Oakland
- Community Features: Pool
- Association: Yes
- Assoc. Name: Westside Townhomes HOA
- Number of Pets: 1
- Pet Restrictions: 25lbs.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Electricity Connected, Sewer Connected, Street Lights
Structural Information
- Windows: Blinds
- Stories/Levels: Two
- Square Feet: 1,180
- Sq. Ft. Source: Public Records
- Year Built: 1986
Lot Features
- Lot Size (Acres): 0.05
- Lot Size (Sq. Ft.): 2,044
- Lot Size: 2044
- Street/Road Desc.: Paved
- Fencing (Description): Fenced, Full Backyard
Financial Considerations
- Lease Price: $2,100
- Assoc Fee Desc.: Required
- Application Fee: $50
- Security Deposit: $2,100
- Pet Deposit: $250
Disclosures and Reports
- APN: 272227923101040
- Property ID: 272227923101040
Listed by Independence Realty Group Llc
Schools
Schools serving 1009 Westside Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Sunridge Elementary School 14455 Sunridge Boulevard, Winter Garden, FL 34787 | PK-5 | 0.8 mi |
SunRidge Middle School 14955 Sunridge Boulevard, Winter Garden, FL 34787 | 6-8 | 0.8 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 2.2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 1009 Westside Dr
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- Townhouse
- Active
- 3Beds
- 3Total Baths
- 1,644Sq. Ft.
Listed by Florida Realty Investments
- Townhouse
- Active
- Updated 11 days ago
- 3Beds
- 3Total Baths
- 1,460Sq. Ft.
Listed by Lpt Realty, Llc
- Townhouse
- Active
- Updated 5 days ago
- 3Beds
- 3Total Baths
- 1,345Sq. Ft.
Listed by Century 21 Carioti
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- Single Family
- Active
- Updated 7 hours ago
- 4Beds
- 3Total Baths
- 2,529Sq. Ft.
Listed by Nova Real Estate Services Inc
- Single Family
- Active
- Updated 1 day ago
- 4Beds
- 3Total Baths
- 2,100Sq. Ft.
Listed by Wra Business & Real Estate
- Single Family
- Active
- Updated 5 hours ago
- 4Beds
- 2Total Baths
- 1,704Sq. Ft.
Listed by Orlando Realty & Property Mgnt
- Single Family
- Active
- Updated 8 hours ago
- 4Beds
- 3Total Baths
- 2,601Sq. Ft.
Listed by Wra Business & Real Estate
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- Single Family
- Active
- Updated 3 days ago
- 5Beds
- 5Total Baths
- 3,401Sq. Ft.
Listed by Agent Group Realty
- Single Family
- Active
- Updated 5 days ago
- 4Beds
- 4Total Baths
- 2,945Sq. Ft.
Listed by Wra Business & Real Estate
- Single Family
- Active
- Updated 6 days ago
- 3Beds
- 3Total Baths
- 2,190Sq. Ft.
Listed by Scates Realty & Investment Pro
- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 2Total Baths
- 1,778Sq. Ft.
Listed by Mack 1 Realty Group
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- Townhouse
- Closed
- 3Beds
- 2Total Baths
- 1,216Sq. Ft.
Listed and Sold by Independence Realty Group Llc
- Townhouse
- Closed
- 3Beds
- 2Total Baths
- 1,440Sq. Ft.
Listed by Avid Realty Llc
Sold by Avid Realty Llc
Sold by Avid Realty Llc
- Townhouse
- Closed
- 3Beds
- 2Total Baths
- 1,076Sq. Ft.
Listed by La Rosa Realty Llc
Sold by La Rosa Realty Llc
Sold by La Rosa Realty Llc
- Condo
- Closed
- Updated 11 days ago
- 3Beds
- 3Total Baths
- 1,699Sq. Ft.
Listed by Yellow Mountain Realty, Llc
Sold by Yellow Mountain Realty, Llc
Sold by Yellow Mountain Realty, Llc
1009 Westside Drive, Winter Garden, FL 34787 (MLS# O6386529) is a Townhouse property with 3 bedrooms and 2 full bathrooms. 1009 Westside Drive is currently listed for rent at $2,100 and was received on February 28, 2026. Want to learn more about 1009 Westside Drive? Do you have questions about finding other real estate for sale or rent in Winter Garden? You can browse all Winter Garden rentals or contact a Coldwell Banker agent to request more information.