GLENEAGLES
Homes for Sale in KISSIMMEE, FL
True comps, carrying-cost math, and listings before the portals.
Gleneagles is a small, established resale pocket of 188 homes built mostly in the early-to-mid 1980s, with a median living area around 1,050 square feet. That size and build era set the price conversation more than anything else here — condition, updates, and how well a unit has been maintained since original construction do most of the talking on value.
With only a single active listing against 188 total homes and 6.0 months of supply, this reads as a balanced market on paper, but that balance is really a function of scarcity — there is simply very little for sale at any given time. A seller with a ready listing has limited direct competition; a buyer waiting for options may need patience or a wider search radius within the same amenity set.
GLENEAGLES right now
🟡 Balanced market. 6.0 months of supply and 50% 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: Low (2 active and pending listings, 3 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($330K) is down 15.4% from the prior 12 months ($390K). With about 3 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: Low (3 and 3 sales in the two windows).
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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
GLENEAGLES market snapshot (as of August 2, 2026): the median sale price is about $330K ($188 per sq ft over the trailing 12 months of closed sales), a median 4 days on market for closed sales, and 6.0 months of supply, a balanced market. The trailing-12-month median is down 15% from the prior 12 months, computed from record-level Stellar MLS closed sales (3 closings in the current window).
GLENEAGLES is a community of 90 homes in KISSIMMEE, Osceola County, built between 2000 and 2004 (median 2002), with a median living area of about 2,009 square feet. 52% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a compact, guard-gated community built out in the 1980s around a golf course and a full slate of recreational amenities, where turnover is naturally slow because there is so little inventory to begin with.
The setting & the homes.
Aerial and on-site photos of GLENEAGLES. Swipe to explore the community.
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GLENEAGLESWho GLENEAGLES is best for.
Best for
- Buyers seeking a lower-maintenance home inside a full-amenity, guard-gated setting.
- Buyers comfortable evaluating and budgeting for age-appropriate updates in a 1980s-built home.
- Buyers who value on-site golf, tennis, and recreational amenities over maximum square footage.
Probably not for
- Buyers who need a large floor plan well above 1,050 square feet.
- Buyers wanting new-construction systems with no near-term update budget.
- Buyers who need to choose from multiple active listings right now rather than wait for inventory.
Price 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 ($330K) IS the median in the snapshot above, and the move from 2025 ($390K) IS the -15.4% one-year change.
Windows contain 0 to 10 sales each (3 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 2004 through 2026. Deemed reliable but not guaranteed.
GLENEAGLES Market Scorecard
GLENEAGLES is currently a buyer's market. About 6.0 months of supply, a median asking price of $429,999, 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 GLENEAGLES, KISSIMMEE
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 GLENEAGLES
Live MLS inventory for GLENEAGLES. 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 and pending GLENEAGLES listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026. Tap any home to ask about it.
GLENEAGLES 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 GLENEAGLES
- Clubhouse · reported on 4 of 4 listings
- Pool · reported on 4 of 4 listings
- Gated Community - Guard · reported on 4 of 4 listings
- Fitness Center · reported on 3 of 4 listings
- Gated · reported on 3 of 4 listings
- Golf Course · reported on 3 of 4 listings
- Tennis Court(s) · reported on 3 of 4 listings
- Golf · reported on 3 of 4 listings
- Gated Community · reported on 3 of 4 listings
- Basketball Court · reported on 2 of 4 listings
- Playground · reported on 2 of 4 listings
- Park · reported on 2 of 4 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.
The GLENEAGLES buying strategy.
If we were buying in GLENEAGLES 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 GLENEAGLES.
A tight resale market inside a mature, amenity-heavy footprint
Homes here span 1981 to 1994 construction, with a median year built of 1983 — this is a fully mature community, not a build-out in progress. At a median of roughly 1,050 square feet, the homes skew smaller and more efficient, which tends to appeal to buyers prioritizing a lower-maintenance footprint over square footage. Given the age range, expect to evaluate roofs, HVAC systems, and other major components on a home-by-home basis rather than assuming a uniform condition across the community.
The amenity package is unusually deep for a community this size: a guarded gate, clubhouse, pool, fitness center, golf course, tennis and basketball courts, a playground, park space, trails, and an on-site restaurant. That amenity density is a real part of what buyers are paying for here, and it is worth confirming current access, fees, and any usage restrictions directly with the HOA before writing an offer, since amenity terms can shift over time even when the physical assets remain.
The location and the amenities are priced into every listing in GLENEAGLES. 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 GLENEAGLES 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 (3.7). Basis: Recent Direction -15.4% year-over-year; Liquidity & Demand 6.0 months of supply; Owner Commitment 52% owner-occupied; Pricing Power 89.9% sale-to-list. Refreshed with each data update.
Why work with Momentum here
With active inventory this thin, timing and access matter more than usual — we track new listings and off-market movement in Gleneagles closely so buyers are not relying on a stale search alone, and we help sellers price against the real, current competitive set rather than a broader golf-community average.
GLENEAGLES in 15 seconds.
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 GLENEAGLES 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 GLENEAGLES sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in GLENEAGLES, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your GLENEAGLES home worth?
Get a no-obligation home value based on real comparable sales in GLENEAGLES, 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 GLENEAGLES on the map →
Frequently Asked Questions
What is the median home price in GLENEAGLES?
How long do homes in GLENEAGLES take to sell?
Is GLENEAGLES a buyer's or seller's market right now?
How many homes are in GLENEAGLES?
What share of GLENEAGLES is owner-occupied?
When were the homes in GLENEAGLES built?
Do cash buyers compete in GLENEAGLES?
Who is the best real estate agent for GLENEAGLES?
How do I find a top KISSIMMEE real estate agent who knows GLENEAGLES?
Can Momentum Realty connect me with an agent for GLENEAGLES?
Should you buy in GLENEAGLES?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near GLENEAGLES 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 2004 (41 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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