8304 LOOKOUT POINTE DRIVE, WINDERMERE, FL, 34786
Active28 days on marketListed Aug 24, 2026MLS #O6428391
About this home
8304 LOOKOUT POINTE DRIVE
Welcome to 8304 Lookout Pointe Drive, an exceptional residence nestled in the highly sought-after Windermere Trails community. This beautifully appointed home offers over 4,100 square feet of thoughtfully designed living space, featuring 6 bedrooms, 5 bathrooms, a private office, spacious loft, and a dedicated media room—perfect for modern family living and entertaining. The heart of the home showcases an open-concept layout filled with natural light, seamlessly connecting the gourmet kitchen, dining, and living areas. The chef-inspired kitchen features premium cabinetry, expansive countertops, stainless steel appliances, and an oversized island ideal for gathering with family and friends. The luxurious primary suite offers a private retreat with a spa-like ensuite bathroom and generous walk-in closets. Additional bedrooms provide flexibility for guests, multigenerational living, or growing families. Step outside to your own private oasis featuring a heated screened-in pool overlooking a tranquil conservation area, creating the perfect setting to relax while enjoying peaceful views and added privacy. Located within the desirable Windermere Trails community, residents enjoy resort-style amenities including a community pool, playground, and scenic walking trails, all while being just minutes from Disney, premier shopping, dining, top-rated schools, and major highways. Combining elegant finishes, generous living spaces, and an unbeatable location, this exceptional home offers the very best of Central Florida living.
Facts & features
The home at a glance
6
Bedrooms
4.5
Bathrooms
4,161
Sqft
0.17 ac
Lot size
2
Garage
2017
Year built
Two
Levels
$2
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Principal and interest plus estimated taxes and insurance. Run your own numbers below.
$214 /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
$214/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Estimates only — taxes at 1.1%/yr and typical insurance; 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.
$/sqft vs Windermere actives
$2 vs $338
Days on market
28 vs 48 typical
Where $2/sqft sits among the 225 Windermere 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.
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
$3,000/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
$875K → $840K
Windermere median sold, yr/yr
96.5%
Sale-to-list ratio (12 mo)
118 of 225
Windermere actives have cut their price
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 99% below the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 8304 LOOKOUT POINTE DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jun ’26$580,000
8323 LOOKOUT POINTE DRIVE · same community
4 bd · 3.5 ba · 2,633 sqft · $220/sqft · 27 DOM
Sold · Aug ’26$625,000
8552 POWDER RIDGE TRAIL · same community
5 bd · 3.5 ba · 2,612 sqft · $239/sqft · 128 DOM
Sold · Dec ’25$507,500
8575 LOOKOUT POINTE DRIVE · same community
3 bd · 2.5 ba · 2,154 sqft · $236/sqft · 119 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
Kamilla Pagotto
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 8304 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 8304 LOOKOUT POINTE DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Kamilla's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
8304 LOOKOUT POINTE DRIVE FAQs
What would the monthly payment be for 8304 LOOKOUT POINTE DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $214/mo — principal and interest, estimated property taxes 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.
Can 8304 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 8304 LOOKOUT POINTE DRIVE?+
The listing reports pets: Cats OK, Dogs OK, Pet Deposit. 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 $7,500, this home is listed about 99% below the Windermere median of $1,089,500. The market section on this page shows how the area is trending.
Which schools are assigned to 8304 LOOKOUT POINTE DRIVE?+
Horizon West Middle (middle), Bay Lake Elementary (elementary), 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
$7,500 is 99% below the WINDERMERE 34786 median of $680,000, and at $2/sqft it sits under the Windermere average of $448.
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.
03Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
04Strong assigned schools
Horizon West Middle, Bay Lake Elementary, Windermere High — Horizon West Middle rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of NEWKEY REAL ESTATE LLC · Carol Valentino, LLC. MLS #O6428391.
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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