1329 WINDSOR DRIVE, KISSIMMEE, FL, 34741
Active85 days on marketListed May 1, 2026MLS #O6403991
About this home
1329 WINDSOR DRIVE
Two stories, two bedrooms, two and a half baths, with the boring expensive stuff already handled. NEW roof overhead, NEW AC, NEW hot water heater, special assessment already paid, NEW living room flooring downstairs, NEW carpet up, and FRESH paint throughout. The first floor opens into a foyer that gives way to a full dining room on one side and a kitchen with breakfast bar seating on the other, both flanking a living room that stretches to back sliders. A second set of sliders off the front leads to a private patio, so you get cross-breeze and two outdoor spots before you even head upstairs. A half bath sits tucked off the kitchen for guests. Upstairs holds two true primary suites, each with its own full bathroom and its own private balcony. One faces the front, one faces the back, both have walk-in closets, and the laundry closet lives upstairs where the laundry actually is. Windsor Pines comes with a community pool and a playground, and the location does the rest of the work. You're a few minutes from The Loop, where the grocery run, the dinner reservation, and the movie all happen in one parking lot. Ten minutes to downtown Kissimmee and the lakefront, straight onto Osceola Parkway or the Turnpike when you need to be elsewhere, and about fifteen minutes from the Disney gates when you don't. Two primaries. Two porches. Two private balconies. One opportunity.
Facts & features
The home at a glance
2
Bedrooms
2.5
Bathrooms
1,290
Sqft
0.02 ac
Lot size
1982
Year built
Two
Levels
$136
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.
$1,725 /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
$1,725/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. 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
$136 vs $209
Days on market
85 vs 45 typical
Where $136/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.
Where it sits
Inside Windsor Pines
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Kissimmee. See the full Kissimmee guide →
Windsor Pines — neighborhood snapshot
Population
2,043
Median age
30
Median income
$38,838
Median home value
$226,500
Avg household
3
Households w/ children
315
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)
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 26% below the KISSIMMEE 34741 median. See the full Kissimmee market guide →
Paper trail
This home's history
Reality check
What actually sold near 1329 WINDSOR DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jul ’25$189,000
2659 CROWN COURT UNIT 11 · same community
3 bd · 2 ba · 1,350 sqft · $140/sqft · 35 DOM
Sold · Oct ’25$186,000
445 FOUNTAINHEAD CIRCLE UNIT 262
3 bd · 2 ba · 1,246 sqft · $149/sqft · 97 DOM
Sold · May ’26$178,000
405 FOUNTAINHEAD CIRCLE UNIT 246
3 bd · 2 ba · 1,246 sqft · $143/sqft · 33 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 1329 WINDSOR DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1329 WINDSOR DRIVE — 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
1329 WINDSOR DRIVE FAQs
What would the monthly payment be for 1329 WINDSOR DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $1,725/mo — principal and interest, the actual property-tax bill, the $375/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 1329 WINDSOR DRIVE?+
The association fee works out to $375 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 1329 WINDSOR DRIVE?+
The most recent tax bill on record (2025) was $992. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 1329 WINDSOR 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 Kissimmee?+
At $175,000, this home is listed about 54% below the Kissimmee median of $379,850. The market section on this page shows how the area is trending.
Which schools are assigned to 1329 WINDSOR DRIVE?+
Highlands Elementary School (elementary), Kissimmee Middle School (middle), Osceola High School (high) — Osceola County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of SERHANT · Shawn Layton. MLS #O6403991.
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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