921 BENDING OAK TRAIL, WINTER GARDEN, FL, 34787
Active86 days on marketListed May 8, 2026MLS #O6405328
About this home
921 BENDING OAK TRAIL
Virtually Staged. Welcome home to 921 Bending Oak Trail in highly sought-after, downtown, golf cart district of Winter Garden! This spacious 4-bedroom, 2.5-bath home is perfectly situated on a private oversized corner lot with serene pond views, offering both privacy and a peaceful backdrop. The thoughtfully designed layout features a first-floor primary suite and convenient downstairs laundry room. The main living areas showcase updated modern, stone-like tile flooring, while the kitchen offers a large walk-in pantry that extends under the staircase for exceptional storage. The spacious Living Room and covered patio are wired for a surround sound system and have beautiful water views from the windows and paver patio. Upstairs, you’ll find generously sized secondary bedrooms, including one with an oversized walk-in closet, along with a large loft ideal for a home office, playroom, or flex space, all featuring engineered hardwood flooring. Enjoy outdoor living with a spacious entertaining area and the added benefit of a rear-entry garage accessed through a private, owners-only alleyway where you can also enter the home without climbing any stairs. Major updates include a roof replacement in 2025, making this home as practical as it is beautiful. Lastly, the location is incredible, the neighborhood is extremely well maintained, offering a tranquil walking community around Brandy Lake and duck filled ponds, a sparkling community pool, entertaining pavilion, community greenspace, and perfect playground for the little ones.
Facts & features
The home at a glance
4
Bedrooms
2.5
Bathrooms
2,517
Sqft
0.16 ac
Lot size
2
Garage
2012
Year built
Two
Levels
$211
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.
$3,955 /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
$3,955/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
−38.5%
$/sqft vs Winter Garden actives
$211 vs $261
Days on market
86 vs 31 typical
Where $211/sqft sits among the 400 Winter Garden 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 Winter Garden
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
WINTER GARDEN 34787 — neighborhood snapshot
Population
93,064
Median age
37.4
Median income
$114,988
Median home value
$475,000
Avg household
3.02
Households w/ children
13,499
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Garden market
$580K → $570K
Winter Garden median sold, yr/yr
97.7%
Sale-to-list ratio (12 mo)
162 of 400
Winter Garden actives have cut their price
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
Paper trail
This home's history
Reality check
What actually sold near 921 BENDING OAK TRAIL
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$530,000
913 BENDING OAK TRAIL · same community
5 bd · 3 ba · 2,212 sqft · $240/sqft · 2 DOM
Sold · Nov ’25$539,000
615 GROVES END LANE
4 bd · 2.5 ba · 2,523 sqft · $214/sqft · 63 DOM
Sold · Aug ’25$540,000
309 BLACK SPRINGS LANE
3 bd · 2.5 ba · 2,529 sqft · $214/sqft · 65 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
Steeve Cadeau
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 921 BENDING OAK TRAIL — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 921 BENDING OAK TRAIL — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Steeve's phone and CRM.
Straight answers
921 BENDING OAK TRAIL FAQs
What would the monthly payment be for 921 BENDING OAK TRAIL?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,955/mo — principal and interest, the actual property-tax bill, the $125/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 921 BENDING OAK TRAIL?+
The association fee works out to $125 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 921 BENDING OAK TRAIL?+
The most recent tax bill on record (2025) was $3,791. 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 921 BENDING OAK TRAIL?+
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 Winter Garden?+
At $529,900, this home is listed about 10% below the Winter Garden median of $589,945. The market section on this page shows how the area is trending.
Which schools are assigned to 921 BENDING OAK TRAIL?+
Sunridge Elementary (elementary), Sunridge Middle (middle), West Orange High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Park/Greenbelt & Trees/Woods & Water views
The park/greenbelt and trees/woods and water view is part of what you're buying — views hold value independently of the structure.
02Time on market is leverage
86 days on market against a Winter Garden median of 31 — sellers in this position are usually ready to negotiate.
03Strong assigned schools
Sunridge Elementary, Sunridge Middle, West Orange High — Sunridge Middle rates 4 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $575,000, now $529,900 — a $45K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of LPT REALTY, LLC · Claire Sims, LLC. MLS #O6405328.
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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