8394 LOOKOUT POINTE DRIVE, WINDERMERE, FL, 34786
Active3 days on marketListed Jul 22, 2026MLS #O6427316
About this home
8394 LOOKOUT POINTE DRIVE
FREE DISNEY FIREWORKS show nightly with purchase! Perfectly positioned in the highly sought-after community of Windermere Trails, this beautifully updated home overlooks picturesque Lake Reams and offers the kind of lifestyle that makes people fall in love with Central Florida. From the stately elevation featuring stone accents, a tile roof, paver driveway, and elegant color palette, you'll immediately notice the attention to detail. Inside, exquisite marble floors, crown moulding, upgraded lighting, and a dramatic wrought iron staircase create a timeless first impression. The recently renovated kitchen is truly the heart of the home. Crisp white cabinetry adorned with traditional millwork, glass display cabinets, brushed gold pendant lighting, and an oversized island blend beauty and function effortlessly. Quartzite, granite, and other fine stone finishes have been thoughtfully incorporated throughout, creating a refined yet comfortable atmosphere. Designed for both entertaining and everyday living, the home features a formal dining room, spacious eat-in kitchen, and multiple gathering spaces overlooking the pool and Lake Reams beyond. Two sets of French doors open to the covered lanai, seamlessly connecting indoor and outdoor living. With five bedrooms, four bathrooms, and a dedicated office on the main level, there is flexibility for growing families, remote work, guests, or multigenerational living. Wake up to water views and enjoy evening sunsets from your private backyard retreat featuring a sparkling pool and covered lanai. The upstairs loft also offers the same beautiful view! Residents of Windermere Trails enjoy miles of walking trails, a community pool, playground, picnic pavilion, and some of the area's most desirable schools. Located just minutes from shopping, dining, and approximately 10 minutes from Disney, this location offers convenience without sacrificing the charm and character that make Windermere so special.
Facts & features
The home at a glance
5
Bedrooms
4
Bathrooms
3,971
Sqft
0.17 ac
Lot size
2
Garage
2016
Year built
Two
Levels
$1
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.
$200 /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
$200/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
$1 vs $346
Days on market
3 vs 32 typical
Where $1/sqft sits among the 246 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
$3,100/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)
119 of 246
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 8394 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 · Aug ’25$949,000
8352 LOOKOUT POINTE DRIVE · same community
6 bd · 4.5 ba · 5,098 sqft · $186/sqft · 95 DOM
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 ’25$585,000
8359 LOOKOUT POINTE DRIVE · same community
4 bd · 4 ba · 2,604 sqft · $225/sqft · 3 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
Kat Bonelli
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 8394 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 8394 LOOKOUT POINTE DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Kat's phone and CRM.
Straight answers
8394 LOOKOUT POINTE DRIVE FAQs
What would the monthly payment be for 8394 LOOKOUT POINTE DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $200/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 8394 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 8394 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 $5,500, this home is listed about 99% 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 8394 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
Five things that matter here
01Under the WINDERMERE 34786 market on paper
$5,500 is 99% below the WINDERMERE 34786 median of $799,000, and at $1/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.
03Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
04Fresh on the market
Only 3 days on market in a Windermere market that averages 32 — if it fits, move quickly.
05Strong assigned schools
Bay Lake Elementary, Horizon West Middle, Windermere High — Bay Lake Elementary rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of LAKEFIELD REALTY GROUP LLC · Autumn Makin. MLS #O6427316.
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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