$399,000
833 Bending Oak Trail
Winter Garden, FL 34787
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage space
Flood zone
About this home
Beautifully maintained and truly turn-key, this 3-bedroom, 2.5-bath townhome is the kind of home where you can simply move in and start enjoying everything Winter Garden has to offer from day one, all while being located in the highly sought-after Golf Cart District just moments from the heart of charming Downtown Winter Garden! From the moment you walk in, you’re welcomed by bright, open living spaces, thoughtful design, and timeless finishes that make the home feel warm, elevated, and instantly inviting. Plantation shutters throughout add that polished custom touch, while the open-concept layout creates the perfect flow for both everyday living and entertaining. Upstairs, the spacious primary suite feels like its own private retreat, thoughtfully positioned away from the guest rooms so you can truly enjoy your own space. Wake up to beautiful open skies and unwind each evening with stunning sunset views right from your bedroom. This is townhome living exactly how it should be. Where else in Winter Garden can you enjoy a home like this, have pool access just a short walk away, and spend your weekends enjoying life instead of worrying about exterior upkeep? Lock it, leave it, travel when you want, and come home to a space that always feels effortlessly cared for. And the location? It’s hard to beat! Bending Oak Trail offers that true neighborhood feel with peaceful evening walks, friendly neighbors, and a sense of community that makes you feel right at home, all while being just moments from the heart of Downtown Winter Garden—one of Central Florida’s most beloved downtowns, known for its brick-lined streets, incredible local restaurants, charming boutiques, cozy coffee shops, weekend Farmer’s Market, and year-round community events that make this area so special. Hop on your golf cart and head down Plant Street for your morning coffee, dinner with friends, shopping, or an evening stroll. Even better, you’re right next to the West Orange Trail, making morning bike rides, walks, and outdoor living part of your everyday lifestyle. With quick access to 429, the Turnpike, SR-50, Disney, Downtown Orlando, and Orlando International Airport, convenience is seamlessly built into daily life. Winter Garden continues to be one of Central Florida’s most sought-after communities, and opportunities to own something this move-in ready, this well-located, and at this price point are incredibly hard to find.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history24 days on market
- Status: ActiveMay 8, 2026
- Listed$435,000May 8, 2026
- Price reduced$399,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Townhouse
- Status
- Active
- Days on market
- 24
- Subdivision
- Oaks/Brandy Lake O
- County
- Orange
- Year built
- 2009
- Living area
- 1,789 sq ft
- Price/sq ft
- $223
- Building area
- 2,290 sq ft (Public Records)
- Lot size
- 2,240 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X (12095C0215F)
- Garage
- 1 spaces
- Annual taxes
- $4,032 (2025)
- Parcel #
- 22-22-27-6124-00-400
- Zoning
- PUD
- MLS #
- O6403683
Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Half bathrooms
- 1
- Flooring
- Carpet, Tile
- Appliances
- Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer, Wine Refrigerator
- Interior features
- Ceiling Fans(s), Eat-in Kitchen, Other, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
- Laundry
- Laundry Room, Upper Level
- Stories / Levels
- Two
- Direction faces
- West
Heating & Cooling
- Heating
- Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 1
- Attached garage
- Yes
HOA & Financial
- HOA fee
- $447 / Monthly
- Monthly HOA
- $447/mo
- Total monthly fees
- $447/mo
- Total annual fees
- $5,364
- HOA name
- Vista Community Association Management
- CDD
- No
- Min lease term
- 1-2 Years
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Buyer to verify.
- Approval process
- Buyer to verify.
Exterior & Construction
- Exterior features
- Other
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Slab
- Road surface
- Asphalt, Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Electricity Available, Water Available
Community
- Pets allowed
- Cats OK, Dogs OK, Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | First | 20x22 |
| Living Room | First | 16x14 |
| Primary Bedroom | Second | 16x13 |
Listing Details
- Listing date
- 2026-05-07
- On market date
- 2026-05-08
- Original list price
- $435,000
- Occupant type
- Vacant
- MLS area
- 34787 - Winter Garden/Oakland
- Listing AOR
- Orlando Regional
- Status changed
- 2026-05-08
- Tax legal description
- OAKS AT BRANDY LAKE 68/51 LOT 40
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From Plant Street heading east, turn right on Story Road, turn left on Alexander Street, turn right on Bending Oak Trail. Property on the left at 833.
More homes like this
$530,000
729 Meadow Glade Dr
Winter Garden, FL 34787
3 bd · 2 ba · 2,070 sqft
Covington Park A B D E F G & J
MLS# O6407943
$616,900
2771 Westyn Cove Ln
Ocoee, FL 34761
5 bd · 3 ba · 3,454 sqft
Eagles Lndg Ph 3
MLS# O6406969
$525,000
12730 Grovehurst Ave
Winter Garden, FL 34787
4 bd · 3 ba · 2,529 sqft
Grovehurst A-D
MLS# G5113229
$330,000
338 Windford Ct
Winter Garden, FL 34787
3 bd · 2 ba · 1,050 sqft
Park Ave Estates
MLS# O6413058
Listings courtesy of Stellar MLS as distributed by MLS GRID
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.
Based on information submitted to the MLS GRID as of June 1, 2026 at 7:30 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA