833 BENDING OAK TRAIL, Winter Garden, FL, 34787 | $399,000

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.

Features

  • Rooms: 3
  • Bedrooms: 3
  • Baths: 2 full / 1 half
  • Laundry: Laundry Room, Upper Level
  • Year Built: 2009
  • Garage: 1-car
  • Heating: Electric
  • Cooling: Central Air
  • Approx Sq. Feet: 1,789
  • Acreage: 0.05
  • Est. Taxes: $4,032
  • HOA Fee: $447 Monthly
  • Elem. School: Tildenville Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High
  • Pet Policy: Cats OK, Dogs OK, Yes
  • Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer, Wine Refrigerator
  • MLS#: O6403683
  • Days on Market: 13 days
  • Website: https://www.raveis.com
    /prop/O6403683/833bendingoaktrail_wintergarden_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is 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. (last updated 5/22/2026 6:07:51 PM)
Listing courtesy of GLOBAL FLORIDA REALTY   Phone: 407-380-3030

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

Melissa.Cohn@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
  • Offers you pre-approval in minutes!
  • Provides a guaranteed closing date that meets your needs
  • Has access to hundreds of loan programs, all at competitive rates
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Pedro DelgadilloInsurance Sales Director, William Raveis Insurance

305.922.5393

Pedro.Delgadillo@raveis.com

Our Insurance Division:

  • Will Provide a home insurance quote within 24 hours
  • Offers full-service coverage such as Homeowner's, Auto, Life, Renter's, Flood and Valuable Items
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    Encompass, Travelers, Fireman's Fund, Middleoak Mutual, One Beacon and American Reliable

833 BENDING OAK TRAIL, Winter Garden, FL, 34787

$399,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Conforming*
30 Year
Fixed-Rate Conforming
15 Year
Fixed-Rate Conforming
Loan Amount $319,200 $319,200 $319,200
Term 360 months 360 months 180 months
Initial Interest Rate** 6.250% 6.490% 5.750%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.474% 6.640% 5.972%
Monthly Tax Payment $336 $336 $336
H/O Insurance Payment $75 $75 $75
Initial Principal & Interest Pmt $1,965 $2,015 $2,651
Total Monthly Payment $2,376 $2,426 $3,062

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.