7765 TOSTETH STREET, KISSIMMEE, FL, 34747
Active23 days on marketListed Jul 13, 2026MLS #O6423586
About this home
7765 TOSTETH STREET
Welcome to 7765 Tosteth Street, a beautifully appointed vacation home in the heart of Windsor Hills Resort — Orlando's premier gated short-term rental community, just minutes from Walt Disney World. This spacious 6-bedroom, 4-bathroom pool home offers 2,812 sq ft of thoughtfully designed living space, perfect for large groups looking for comfort, privacy, and resort-style amenities. The open-concept main floor features a generous living and dining area, a fully equipped kitchen, a first-floor bedroom with full bath — ideal for guests who prefer single-level living — a dedicated laundry room, and a game room for added entertainment. Step outside to your private screened pool with heated spa, surrounded by a covered patio and deck — the perfect setting for relaxing afternoons under the Florida sun. Windsor Hills Resort amenities include a clubhouse, resort-style community pool, waterpark, fitness center, game room, tennis courts, and 24-hour gated security — everything your guests need without ever leaving the community. Whether you're looking for a turn-key investment property with strong short-term rental potential or a private family retreat steps from the magic of Orlando, 7765 Tosteth Street is ready to deliver. Offered fully furnished and ready to generate income from day one.
Facts & features
The home at a glance
6
Bedrooms
4
Bathrooms
2,812
Sqft
0.14 ac
Lot size
2
Garage
2005
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.
$4,976 /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
$4,976/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.
$/sqft vs Kissimmee actives
$249 vs $208
Days on market
23 vs 52 typical
Where $249/sqft sits among the 400 Kissimmee 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 Windsor Hills, 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
$2,100/mo median
Live Kissimmee rental listing data — this home’s rate depends on size, condition and furnishing.
Where it sits
Inside Windsor Hills
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Windsor Hills is a short-term-rental community. See the full guide →
Windsor Hills — neighborhood snapshot
Population
686
Median age
31
Median income
$92,154
Median home value
$297,100
Avg household
4
Households w/ children
78%
For the school run
Osceola County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Kissimmee market
$365K → $350K
Kissimmee median sold, yr/yr
97.3%
Sale-to-list ratio (12 mo)
164 of 400
Kissimmee actives have cut their price
Median sold price, Kissimmee, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 75% above the KISSIMMEE 34747 median. See the full Kissimmee market guide →
Paper trail
This home's history
Reality check
What actually sold near 7765 TOSTETH STREET
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$690,000
7803 BASNETT CIRCLE · same community
6 bd · 4 ba · 2,812 sqft · $245/sqft · 20 DOM
Sold · Jul ’26$619,000
7753 BASNETT CIRCLE · same community
6 bd · 4 ba · 2,812 sqft · $220/sqft · 7 DOM
Sold · Nov ’25$729,000
7801 BASNETT CIRCLE · same community
7 bd · 4 ba · 2,812 sqft · $259/sqft · 80 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 7765 TOSTETH STREET — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 7765 TOSTETH STREET — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
7765 TOSTETH STREET FAQs
What would the monthly payment be for 7765 TOSTETH STREET?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,976/mo — principal and interest, the actual property-tax bill, the $171/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 7765 TOSTETH STREET?+
The association fee works out to $171 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 7765 TOSTETH STREET?+
The most recent tax bill on record (2025) was $7,331. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Can 7765 TOSTETH STREET be rented short-term?+
Yes — this home sits inside Windsor Hills, 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 7765 TOSTETH STREET?+
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 Kissimmee?+
At $699,000, this home is listed about 84% above the Kissimmee median of $379,000. The market section on this page shows how the area is trending.
Which schools are assigned to 7765 TOSTETH STREET?+
Celebration High School (high), Westside K-8 School (elementary) — Osceola County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$699,000 runs 75% above the KISSIMMEE 34747 median — but at 2,812 sqft it's also 56% larger than the typical Kissimmee listing.
02Zoned for nightly rentals
Windsor Hills 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.
Keep looking
Similar homes nearby
Listing courtesy of FLORIDA 360 REALTY LLC · Cristobal Murature Reggiardo. MLS #O6423586.
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.
Never miss a listing
New Kissimmee homes, in your inbox
Like 7765 TOSTETH STREET but not quite? A daily digest of every new listing in Kissimmee — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask David to ping you on any price or status change →