8931 LOOKOUT POINTE DRIVE, WINDERMERE, FL, 34786
Active1 days on marketListed Jul 24, 2026MLS #O6427614
About this home
8931 LOOKOUT POINTE DRIVE
Investor opportunity in the sought after Windermere Trails community! This tenant-occupied home offers immediate rental income in a high-demand location just minutes from Disney World (Magic Kingdom, Hollywood Studios, Animal Kingdom, Epcot Center and Disney Springs), Winter Garden Historic District, Doctor Philips Restaurant hub, Hamlin Town Center, Horizon West, top-rated schools, shopping, dining, and major highways. Recent updates include new interior and exterior paint, new luxury vinyl plank flooring throughout the second floor, new stair carpet, and a new refrigerator; roof is approximately 9 years old. A turnkey addition to any investment portfolio with excellent long-term appreciation potential. (Updated 2nd floor photos will be added soon to show new flooring)
Facts & features
The home at a glance
5
Bedrooms
4
Bathrooms
2,989
Sqft
0.14 ac
Lot size
2
Garage
2017
Year built
Two
Levels
$249
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.
$5,315 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
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
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$5,315/mo
Includes estimated PMI — it drops off once you reach 20% equity. 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
+1.6%
Days on market
1 vs 32 typical
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.
The investor lens
Two ways this home pays
This home sits inside Lakeside Village, a community zoned to allow true short-term rentals — so it can earn as a nightly rental or a traditional lease. Here’s how the two paths compare.
Short-term rental
Zoned & eligible
Projected nightly rate, occupancy and annual revenue for this exact home.
Long-term rental
$3,100/mo median
Live Windermere rental listing data — this home’s rate depends on size, condition and furnishing.
Where it sits
Inside Lakeside Village
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Lakeside Village is a short-term-rental community. See the full guide →
Lakeside Village — neighborhood snapshot
Population
19,390
Median age
36
Median income
$123,605
Median home value
$489,452
Avg household
3
Households w/ children
2,897
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Windermere market
$839K → $1.0M
Windermere median sold, yr/yr
96.4%
Sale-to-list ratio (12 mo)
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 7% below the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
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
Eric Chery
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 8931 LOOKOUT POINTE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 8931 LOOKOUT POINTE DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Eric's phone and CRM.
Straight answers
8931 LOOKOUT POINTE DRIVE FAQs
What would the monthly payment be for 8931 LOOKOUT POINTE DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,315/mo — principal and interest, the actual property-tax bill, the $9/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 8931 LOOKOUT POINTE DRIVE?+
The association fee works out to $9 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 8931 LOOKOUT POINTE DRIVE?+
The most recent tax bill on record (2025) was $10,154. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Can 8931 LOOKOUT POINTE DRIVE be rented short-term?+
Yes — this home sits inside Lakeside Village, a community zoned to allow short-term rentals. Nightly-rental income could change the math on this purchase entirely; request a free rental income analysis and our team will prepare projections for this exact home.
Are pets allowed at 8931 LOOKOUT POINTE DRIVE?+
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 Windermere?+
At $745,000, this home is listed about 32% below the Windermere median of $1,099,500. The market section on this page shows how the area is trending.
Which schools are assigned to 8931 LOOKOUT POINTE DRIVE?+
Bay Lake Elementary (elementary), Horizon West Middle (middle), Windermere High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Under the WINDERMERE 34786 market on paper
$745,000 is 7% below the WINDERMERE 34786 median of $799,000, and at $249/sqft it sits under the Windermere average of $447.
02Zoned for nightly rentals
Lakeside Village is one of the communities zoned to allow true short-term rentals — nightly income could change the math on this purchase entirely. Ask for the free rental analysis below.
03Fresh on the market
Only 1 day on market in a Windermere market that averages 32 — if it fits, move quickly.
04Strong assigned schools
Bay Lake Elementary, Horizon West Middle, Windermere High — Bay Lake Elementary rates 4 of 5. Always verify assignments with the district.
Listing courtesy of SPECIALIZED PROPERTY MANAGEMENT · Lilly Vazquez. MLS #O6427614.
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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