Community · Kissimmee, FL
Windsor At Westside Kissimmee, FL Homes For Sale & Real Estate
Windsor At Westside, Kissimmee, FL, is a community in Osceola County with 5 homes for sale right now. Construction dates to 2017 through 2020.
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Windsor At Westside Market at a Glance
Live MLS · Updated Oct 13, 2026
- Active Inventory
- 5
- New Listings (30d)
- 1
- Pending Sales
- 0
- Median List Price
- $499,900
- Avg Days on Market
- 116
Residential MLS data for Windsor At Westside, updated nightly. View full market reports →
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Market Overview
Windsor At Westside real estate market
There are 5 active listings for sale in Windsor At Westside right now. The median list price is $499,900, or about $196 per square foot. Listings span $412,800 to $979,000, so there is inventory across most budgets. Homes are averaging 116 days on market. These figures update from the MLS as the market moves.
Windsor At Westside Market Stats
MLS data updated October 13, 2026- Active Listings
- 5
- Median List Price
- $499,900
- Median $/Sq Ft
- $196
- Avg Days on Market
- 116
- Price Range
- $412,800 to $979,000
Frequently Asked Questions
- How many homes are for sale in Windsor At Westside?
- There are 5 active listings for sale in Windsor At Westside right now, and these counts update from the MLS as homes come on the market and go under contract. Prices cluster fairly closely, with the top of the market about 2.4 times the entry level. Ask us to set up a search alert and you will see new Windsor At Westside listings the day they reach the market.
- What is the median home price in Windsor At Westside?
- The median list price in Windsor At Westside is $499,900, or roughly $196 per square foot. The median is the midpoint of what is currently listed, so about half of Windsor At Westside homes ask more and half ask less, within a broader range of $412,800 to $979,000. The median sits in the lower part of that range, so most Windsor At Westside homes are nearer the entry level and a few high-end listings pull the top up. We can pull recent comparable sales to price a specific home more precisely.
- What price range do homes in Windsor At Westside cover?
- Homes for sale in Windsor At Westside currently range from about $412,800 at the entry level to $979,000 at the top of the market. That spread reflects the local mix, from smaller condos and townhomes up to larger single-family and luxury homes, with the median list price around $499,900. The spread is moderate, so there is real choice here without the extremes some markets show. Tell us your budget and must-haves and we will send the Windsor At Westside listings that actually fit.
- How long do homes take to sell in Windsor At Westside?
- Homes in Windsor At Westside are averaging 116 days on market, measured from the day a listing goes live to the day it goes under contract. That is a measured pace, which usually leaves buyers room to negotiate and makes pricing at the outset matter more for sellers. Days on market in Windsor At Westside also shift with the season and with how a home is priced, so a sharply priced listing can still sell well ahead of the average.
About Windsor At Westside
Windsor At Westside, Kissimmee, FL, is a community in Osceola County with 5 homes for sale right now. Construction dates to 2017 through 2020. Listings update from the MLS nightly.
Homes & Architecture
Homes for sale in Windsor At Westside
Homes for sale in Windsor At Westside offer 4 to 9 bedrooms and 3.5 to 6 baths. Living areas run from about 2,102 to 4,391 square feet. The mix here includes single family and townhouse homes. Current prices run from $412,800 to $979,000. The homes on the market were built between 2017 and 2020.
Map
Where Windsor At Westside is in Kissimmee
Centred on the homes listed and recently sold in Windsor At Westside.
HOA
Windsor At Westside HOA fees
- Median HOA fee
- $606/mo
- Typical range
- $591 to $640
- Lowest to highest
- $563 to $640
- Listings with a fee
- 5 of 5
Across the 5 homes for sale in Windsor At Westside that list an HOA fee, the median is $606 a month. Half of them fall between $591 and $640. Fees quoted quarterly or yearly are converted to a monthly figure so they compare directly.
The fee most often covers grounds maintenance, cable TV, security, internet, pest control and recreation facilities. Coverage differs from one building or section to the next, so read what a specific listing includes before comparing it with another.
Listings here most often mention clubhouse, pool, fitness center, on-site management and sidewalks.
All 5 listings that state a pet policy allow pets, some with size or number limits.
From current MLS listings in Windsor At Westside; the figures change as homes come and go. Confirm the fee, any special assessments and the association's rules with the HOA before you buy.
Market & Value
Windsor At Westside market and home values
Values in Windsor At Westside track the community's own sales more closely than any broad regional number. The median list price in Windsor At Westside is around $499,900, or roughly $196 per square foot. That sits about 19% above the Osceola County median, which shows where Windsor At Westside lands in the local market. Recent asking prices have run from $412,800 to $979,000, so the home you choose within Windsor At Westside matters as much as the community average. Homes here have recently taken about 116 days to go under contract, a useful gauge of how quickly the Windsor At Westside market is moving. For pricing an offer or a listing, comparable sales within Windsor At Westside carry more weight than any headline number, since homes of the same type and size set the real range. Pure Equity can pull the active and recently sold homes in Windsor At Westside so you work from real numbers, not an estimate.
How It Compares
Windsor At Westside compared to nearby Kissimmee communities
Windsor At Westside sits 2 of 7 on median price among these Kissimmee communities. Price per square foot is the fairer comparison between communities, because it adjusts for the fact that one neighborhood builds bigger homes than another. Days on market shows how quickly each one is actually selling.
| Community | Homes | Median | $/Sq Ft | Days |
|---|---|---|---|---|
| Ambar Residences | 6 | $581,400 | $659 | 170 |
| Windsor At Westside this page | 5 | $499,900 | $196 | 116 |
| Storey Lake | 4 | $431,000 | $254 | 154 |
| Tohoqua | 2 | $404,950 | $188 | 13 |
| Spectrum At Reunion | 2 | $367,500 | $243 | 384 |
| Tanglewood Preserve | 3 | $339,000 | $212 | 201 |
| Poinciana Vlg 2 Nbhd | 3 | $300,000 | $211 | 54 |
Medians come from active listings in each community and move as inventory turns over. They describe the homes currently for sale, not what any one home is worth.
Who It Suits
Is Windsor At Westside right for you?
A quick read on who fits Windsor At Westside saves time before you visit. Windsor At Westside suits a range of buyers, from first-time owners to move-up families, who want a home in Kissimmee with the everyday conveniences of the area close by. On price, Windsor At Westside lands in the middle of the market, a common fit for move-up buyers and full-time residents. Whether Windsor At Westside is right for you depends on how you plan to use the home, full time or seasonally, and Pure Equity can walk you through the tradeoffs before you commit.
Amenities & Lifestyle
Living in Windsor At Westside
Windsor At Westside is a residential neighborhood, and its homeowners association maintains the shared areas and community standards.
Location
Windsor At Westside location
Windsor At Westside is located in Kissimmee, part of Osceola County, Florida. The Kissimmee area's shopping, dining, schools, and parks are all nearby, and the region's job centers, beaches, and airports are within driving distance.
Buying in Windsor At Westside
Buying a home in Windsor At Westside
Buying in Windsor At Westside follows the same path as the rest of Osceola County. Getting a mortgage pre-approval first tells you your real budget and lets you move quickly when the right home comes up. Property taxes factor into the monthly payment: the median annual property tax in Osceola County is about $2,498. Florida's homestead exemption lowers the taxable value of a primary residence, and the Save Our Homes cap limits how fast that assessed value can rise from year to year. Budget for homeowners insurance as well. Rates in Florida reflect wind and flood exposure, so gather quotes early and check whether a specific address sits in a FEMA flood zone. Once you are under contract, plan for a home inspection and, if you are financing, a lender appraisal, both of which fall inside the inspection period. Working with an agent who knows Kissimmee means you see new listings in Windsor At Westside the day they reach the market.
Selling in Windsor At Westside
Selling a home in Windsor At Westside
A successful sale in Windsor At Westside comes down to pricing, presentation, and marketing. List prices in Windsor At Westside currently center around $499,900, which is a starting reference for where a comparable home might be positioned. Homes that are decluttered, professionally photographed, and priced to recent comparable sales tend to draw the most interest in the first two weeks, when a listing is newest and gets the most views. Florida sellers usually pay the documentary stamp tax on the deed, currently $0.70 per $100 of the sale price in most counties, along with prorated property taxes and, by local custom in many areas, the owner's title insurance policy. We provide a no-obligation home valuation for Windsor At Westside owners in Kissimmee, so you can see what your property could sell for before you commit to listing.
Thinking of Selling?
What is your Windsor At Westside home worth?
Online estimates miss what makes a home different. Tell us about yours and a licensed listing agent will send you a pricing opinion based on what has actually closed near you in Windsor At Westside.
Listing agents and seller representation in Windsor At Westside
Thinking about selling in Windsor At Westside? The agent you pick shapes two numbers: what your home closes for, and how long it takes. A listing agent, also called a seller's agent, prices the property against what has actually closed nearby. They also prepare and market it, screen the offers that arrive, and negotiate the terms rather than just the price.
Conditions in Windsor At Westside sit close to balanced, which rewards sellers who price against real closed sales instead of neighboring asking prices. Homes here are averaging about 116 days from listing to accepted offer, so build that into your moving timeline.
Community-level detail matters most here. Association rules, what the fees cover, and which buildings sell fastest all affect your outcome. So does whether a buyer needs board approval before closing. None of it appears in a listing description. All of it decides whether a sale closes on time.
Pure Equity is a licensed Florida brokerage serving Windsor At Westside. Onias Derilus is the broker of record, Florida Real Estate Broker license BK3276618. A broker holds a higher license than an agent working under one. In practice that means the person advising you on price is also the one legally responsible for the file. That matters most when a deal gets complicated.
More on this: understanding your listing agreement · selling a house with an HOA violation
Realtors and real estate agents serving Windsor At Westside
People search for realtors, real estate agents, and real estate brokers more or less interchangeably. For most purposes the job title matters less than licensing and representation. Every licensed agent in Florida works under a broker. That broker carries final responsibility for the transaction.
What separates real estate professionals in Windsor At Westside is specificity. Can they answer questions about your street, not just your city? Ask what they have closed nearby and how they arrived at a price. A grounded answer cites particular recent sales. It also explains why those homes compare to yours. Vague reassurance is the warning sign.
More on this: how waterfront homes are valued · how South Florida condos are valued · when and how to price your home
Buyer's agents in Windsor At Westside
A buyer's agent represents the purchaser rather than the owner. They identify properties that actually fit and research what comparable homes sold for, not what they asked. They also advise on offer strategy. Finally, they manage inspection and financing deadlines through to closing.
Where buyers have room to negotiate, as they do in Windsor At Westside, the leverage is only worth something if you know where it exists and what to ask for. If you are buying and selling at the same time, which is common for people moving within Osceola County, sequencing the two is its own skill: contingencies, timing, and what happens if one closing slips all need planning before either home goes on the market.
What representation costs
Real estate commissions are negotiable. No law, multiple listing service, or association sets them. If an agent tells you there is a standard rate, they are misinforming you. What you pay is agreed between you and the brokerage you hire. Get it in writing before the work begins.
Industry rules changed in 2024. Now a buyer and their agent must put compensation in a written buyer agreement before touring homes together. Sellers may still offer to contribute toward the buyer's side. However, that is negotiated rather than assumed. It is worth thinking through with your listing agent before you go live.
More on this: how commission is actually structured · how long it takes to sell a house · what you actually walk away with
Buying Instead?
Search Windsor At Westside with someone local
We will tell you which listings are worth your time, what comparable homes actually closed for, and how to structure an offer that holds up through inspection and financing.
Frequently asked questions
How do I find a listing agent in Windsor At Westside?
Ask any listing agent you interview two questions. Which homes have they closed near Windsor At Westside, and how did they arrive at their suggested price? A grounded answer names recent closed sales. It also explains why those homes compare to yours. With a median around $499,900 here, the gap between realistic pricing guidance and optimistic guidance is real money. Verify the license too. Florida licenses are public and searchable through the state's DBPR portal. Pure Equity is a licensed brokerage serving Osceola County. You can reach the broker directly at (561) 835-5400.
What does a seller's agent actually do?
A seller's agent prices the home against comparable closed sales. Before it goes live, they advise on repairs and presentation. Then they handle photography and marketing, and put the home in front of buyers and other agents. When offers arrive, they screen them and negotiate both price and terms. Terms matter as much as the number, because inspection windows, financing contingencies, and closing dates all affect whether an offer reaches the closing table.
How much does a real estate agent cost in Windsor At Westside?
Commissions are fully negotiable. No law or real estate board sets them. What you pay is whatever you and your brokerage agree to in writing before work begins. Since the 2024 rule changes, buyers and their agents must agree compensation in a written buyer agreement before touring homes. Any seller contribution toward the buyer's side is negotiated rather than automatic. Ask any agent you interview to put their fee in writing.
What is the difference between a realtor, a real estate agent, and a broker?
A real estate agent holds a state license to represent buyers and sellers. A broker holds a higher-level license and can operate a brokerage. That broker also carries final legal responsibility for the office's transactions. Realtor is a membership term for agents belonging to the National Association of Realtors. For someone buying or selling in Windsor At Westside, three practical questions matter. Is the person licensed, who do they represent in your transaction, and what can they actually tell you about your local market?
Do I need an agent to buy a home in Windsor At Westside?
You are not legally required to use one, but most buyers in Windsor At Westside do. A buyer's agent handles the parts that are easy to get wrong. That means identifying what comparable homes actually closed for, spotting condition or association issues early, and managing inspection and financing deadlines. Even in a slower market, negotiating room is only useful if you know where it exists.
Can one agent help me sell my current home and buy the next one?
Yes. For people moving within Osceola County it is often the more practical route, because one person coordinates both timelines. Sequencing is the hard part. Should your purchase be contingent on your sale? How would you cover a gap if the closings do not line up? What happens if one side is delayed? Plan all of that before either home is listed, rather than after an offer arrives.
Public Records
Look up Windsor At Westside property records
Anything on this page that affects what a home costs to own, assessed value, exemptions, flood zone, is published by a public agency. These are the official sources, not our summaries of them.
Florida property appraisers by county
Assessed value, homestead exemption status, and recorded sales history for any parcel.
FEMA Flood Map Service Center
Look up the official flood zone for an address before you budget for insurance.
Florida Department of Revenue, property taxes
How Florida assesses property, and which exemptions you can claim.
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