7755 GRASSENDALE STREET, KISSIMMEE, FL, 34747
Active79 days on marketListed Apr 23, 2026MLS #O6396993
About this home
7755 GRASSENDALE STREET
Welcome to 7755 Grassendale Street! This TURNKEY, well-maintained 4-bedroom, 4-bath home is move-in ready and ideal as a primary residence or short-term vacation rental. The open-concept layout features a large foyer, spacious dining area, family room, and a well-appointed kitchen with stainless steel appliances, granite countertops, breakfast bar, and nook. All bedrooms feature luxury vinyl plank flooring and are tastefully themed, while the main living areas are tile. The converted 2-car garage (2021) is air-conditioned and serves as an entertainment space with a home theater, gaming consoles, and a sit-down arcade game. Step outside to the covered lanai and enjoy the refurbished (2022) pool and spa—perfect for relaxing in the Florida sun. The community offers a 24-hour guard-gated entrance and resort-style amenities, including a 10,000 sq. ft. clubhouse, lagoon-style pool with water slides, fitness center, movie theater, sports courts, playground, and walking trail. Conveniently located minutes from Disney, with dining, shopping, and everyday essentials nearby. This truly is a MUST SEE home!
Facts & features
The home at a glance
4
Bedrooms
4
Bathrooms
1,824
Sqft
0.14 ac
Lot size
2
Garage
2007
Year built
One
Levels
$337
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.
$4,393 /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
$4,393/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
+21.8%
$/sqft vs Kissimmee actives
$337 vs $211
Days on market
79 vs 45 typical
Where $337/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 · projected
$53,368/yr gross
Projected nightly rate, occupancy and annual revenue for this exact home.
Long-term rental
$2,150/mo median
Live Kissimmee rental listing data — this home’s rate depends on size, condition and furnishing.
The Four Corners short-term market
▼ Softening48%
Occupancy
▼ 37% yr/yr
$325
Avg nightly rate
▲ 13% yr/yr
$38K/yr
Revenue per listing
$151
RevPAR
78 days
Booking lead time
5.7 nights
Avg stay
3
Typical min nights
11,479
Active rentals
▼ 20% supply
Seasonality — monthly occupancy
Peaks at 57% in Jul · bottoms at 36% in Jun
Last 12 months of data, January–December, bars scaled to the seasonal peak. Market-wide averages across all home sizes in Four Corners — the projection above is specific to this home’s size.
Where it sits
Inside Windsor Hills
Drive times from this address
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
$369K → $358K
Kissimmee median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
143 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 62% above the Windsor Hills median. See the full Kissimmee market guide →
Paper trail
This home's history
Reality check
What actually sold near 7755 GRASSENDALE STREET
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Feb ’26$595,000
2619 PAWNALL STREET · same community
4 bd · 4 ba · 1,824 sqft · $326/sqft · 28 DOM
Sold · Dec ’25$627,750
7749 TEASCONE BOULEVARD · same community
5 bd · 5 ba · 2,342 sqft · $268/sqft · 8 DOM
Sold · Aug ’25$600,000
7754 TEASCONE BOULEVARD · same community
5 bd · 5 ba · 2,342 sqft · $256/sqft · 21 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
Lyra Rae
Realtor · CENTURY 21 Edge
Tours, negotiation, and every question about 7755 GRASSENDALE STREET — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 7755 GRASSENDALE STREET — before you fall in love.
See it in person
Schedule a tour
Live availability from Lyra's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
7755 GRASSENDALE STREET FAQs
What would the monthly payment be for 7755 GRASSENDALE STREET?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,393/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 7755 GRASSENDALE 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 7755 GRASSENDALE STREET?+
The most recent tax bill on record (2025) was $6,149. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Can 7755 GRASSENDALE 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 7755 GRASSENDALE 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 $615,000, this home is listed about 62% above the Kissimmee median of $379,850. The market section on this page shows how the area is trending.
Which schools are assigned to 7755 GRASSENDALE 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
Four things that matter here
01Positioned at the premium end
$615,000 runs 62% above the Windsor Hills median.
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.
04The price has already moved
Listed at $625,000, now $615,000 — a $10K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of FLORIDA REALTY RESULTS LLC · Greg Lowe. MLS #O6396993.
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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