WESTSIDE VILLAGE
Homes for Sale in WINDERMERE, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
WESTSIDE VILLAGE right now
🟡 Balanced market. 2.6 months of supply and 0% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of August 2, 2026. Confidence: High (3 active and pending listings, 12 closed sales in 12 months).
🟡 Off the recent peak. The trailing-12-month median ($630K) is down 6.0% from the prior 12 months ($670K). With about 6 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Medium (12 and 7 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
WESTSIDE VILLAGE market snapshot (as of August 2, 2026): the median sale price is about $630K ($236 per sq ft over the trailing 12 months of closed sales), a median 62 days on market for closed sales, and 2.6 months of supply, a balanced market. The trailing-12-month median is down 6% from the prior 12 months, computed from record-level Stellar MLS closed sales (12 closings in the current window).
WESTSIDE VILLAGE is a community of 151 homes in WINDERMERE, Orange County, built between 2017 and 2018 (median 2018), with a median living area of about 2,665 square feet. 32% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of WESTSIDE VILLAGE. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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WESTSIDE VILLAGEPrice History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($630K) IS the median in the snapshot above, and the move from 2025 ($670K) IS the -6.0% one-year change.
Windows contain 0 to 15 sales each (12 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2018 through 2026. Deemed reliable but not guaranteed.
WESTSIDE VILLAGE Market Scorecard
WESTSIDE VILLAGE is currently a seller's market. About 2.8 months of supply, a median asking price of $950,000, and homes go under contract in about 22 days.
Go deeper: county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in WESTSIDE VILLAGE, WINDERMERE
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period August 2026 through August 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in WESTSIDE VILLAGE
Live MLS inventory for WESTSIDE VILLAGE. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 125 daysTop listing
Active · 31 days
Active · 1 days
Active · 69 days
Pending · 8 daysActive and pending WESTSIDE VILLAGE listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2018 through 2026. Tap any home to ask about it.
WESTSIDE VILLAGE on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at WESTSIDE VILLAGE
- Pool · reported on 10 of 13 listings
- Playground · reported on 9 of 13 listings
- Clubhouse · reported on 4 of 13 listings
- Community Mailbox · reported on 3 of 13 listings
- Park · reported on 2 of 13 listings
- Deed Restrictions · reported on 2 of 13 listings
- Fitness Center · reported on 1 of 13 listings
- Fence Restrictions · reported on 1 of 13 listings
- Trail(s) · reported on 1 of 13 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Bay Lake Elementary · Elementary
- Horizon West Middle School · Middle
- Windermere High School · High
Zoned schools reflect the assignments reported on recent WESTSIDE VILLAGE listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any WESTSIDE VILLAGE address.
The WESTSIDE VILLAGE buying strategy.
If we were buying in WESTSIDE VILLAGE today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in WESTSIDE VILLAGE.
A closer look at the WESTSIDE VILLAGE market
At a median of $236 per square foot, WESTSIDE VILLAGE prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 2.6 months of supply, a balanced market and the trailing-12-month median down 6% year over year. Homes that do trade take a median 62 days on market, useful leverage on any listing that has lingered.
The housing stock is 151 homes built between 2017 and 2018, and 32% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in WESTSIDE VILLAGE. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in WESTSIDE VILLAGE buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (5.3). Basis: Recent Direction -6.0% year-over-year; Liquidity & Demand 2.6 months of supply; Owner Commitment 32% owner-occupied; Pricing Power 94.0% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- Mandatory HOA. Confirm current dues
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a WESTSIDE VILLAGE buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed WESTSIDE VILLAGE sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in WESTSIDE VILLAGE, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your WESTSIDE VILLAGE home worth?
Get a no-obligation home value based on real comparable sales in WESTSIDE VILLAGE, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See homes for sale in WESTSIDE VILLAGE on the map →
Frequently Asked Questions
What is the median home price in WESTSIDE VILLAGE?
How long do homes in WESTSIDE VILLAGE take to sell?
Is WESTSIDE VILLAGE a buyer's or seller's market right now?
How many homes are in WESTSIDE VILLAGE?
What share of WESTSIDE VILLAGE is owner-occupied?
When were the homes in WESTSIDE VILLAGE built?
Do cash buyers compete in WESTSIDE VILLAGE?
Who is the best real estate agent for WESTSIDE VILLAGE?
How do I find a top WINDERMERE real estate agent who knows WESTSIDE VILLAGE?
Can Momentum Realty connect me with an agent for WESTSIDE VILLAGE?
Nearby Communities
Explore more neighborhoods near WESTSIDE VILLAGE with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2018 (54 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.
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