Villas At Shaddow Bay
Homes for Sale in Kissimmee, FL

All 2,933 homes for sale in Kissimmee, FL · median $373,400 · Osceola County homes for sale

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Built fromLive Stellar MLS dataUpdated twice daily

Villas At Shaddow Bay is a community in Kissimmee, Osceola County, FL. Across Kissimmee as a whole, 2,431 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,223 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,910 ($5,310 with the full homestead exemption).

Live · Villas At Shaddow Bay Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Track record · years of records
0
Failed listings · 2025
peaked at 1 in 2025
Jon Brooks, founder of Momentum Realty
Jon's Current Read

There is not enough active listing data in the current MLS feed for Villas At Shaddow Bay to point to a median price or a pace-of-market figure right now, and that itself is the read: this is a small, quiet villa community where inventory can sit thin for stretches at a time. When a unit does list, pricing tends to be set unit-by-unit against condition and any recent updates rather than against a running comp trend, because there simply are not enough concurrent sales to build one.

For a buyer, that means doing your own legwork on recent closed sales rather than leaning on an average, since one or two transactions can swing what looks like a 'typical' price here. For a seller, thin inventory can work in your favor at listing time, but it also means you should not expect a flood of competing offers to force the issue. Price it on the home's own condition and let the villa format do the rest.

Nearby homes for sale

No active listings inside Villas At Shaddow Bay right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.

3115 FOX SQUIRREL DRIVE #3115
$160K · 0.0 mi away
3 bd · 2 ba · 1,250 sqft
3115 FOX SQUIRREL DRIVE #3115
Listed by CENTURY 21 ALL HOMES & PROPERT
3111 RIO GRANDE TRAIL
$257K · 0.0 mi away
3 bd · 2 ba · 1,375 sqft
3111 RIO GRANDE TRAIL
Listed by M2M REALTY
3023 RIO GRANDE TRAIL #3023
$209K · 0.0 mi away
3 bd · 2 ba · 1,250 sqft
3023 RIO GRANDE TRAIL #3023
Listed by KELLER WILLIAMS ADVANTAGE III
3226 RIO GRANDE TRL #3226
$165K · 0.1 mi away
3 bd · 2 ba · 1,375 sqft
3226 RIO GRANDE TRL #3226
Listed by KN PREMIER REALTY, INC
2931 RIO GRANDE TRAIL #2981
$180K · 0.1 mi away
2 bd · 2 ba · 1,025 sqft
2931 RIO GRANDE TRAIL #2981
Listed by LPT REALTY, LLC
3226 FOX SQUIRREL DRIVE
$190K · 0.1 mi away
2 bd · 2 ba · 1,100 sqft
3226 FOX SQUIRREL DRIVE
Listed by SMART MIAMI REALTY, LLC.

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

The 60-Second Overview

Villas At Shaddow Bay is a compact villa community in Kissimmee, Osceola County, and current MLS records show no community amenities documented against active listings, so what you are buying is the unit and its immediate maintenance structure rather than a packaged clubhouse or recreation set.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Best for

  • Buyers wanting a smaller, easier-upkeep home in Kissimmee without a large yard to maintain
  • Buyers comfortable evaluating price on a unit-by-unit basis rather than leaning on a community-wide average
  • Buyers who are not shopping for organized common amenities and are fine with a plain, low-frills setup

Probably not for

  • Buyers who want a pool, clubhouse, or other documented recreational amenity as part of the purchase
  • Buyers who want a large lot or significant private outdoor space
  • Buyers who need a high volume of current comps to feel confident pricing quickly

The market around Villas At Shaddow Bay

Villas At Shaddow Bay is a small community — 1 recorded sale on file, most recently in 2025 — too few for its own price trend. Here is the market around it.

Across Osceola County, 4,370 homes are active and 1,137 pending (21% under contract).

Homes here are condominium.

ZIP and county figures describe the wider market, not Villas At Shaddow Bay specifically. Momentum Research analysis of MLS records.

If we were buying in Villas At Shaddow Bay today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Villas At Shaddow Bay.

Best Buy
Buyers who want a smaller, lower-maintenance home in Kissimmee rather than a large single-family lot.
Biggest Risk
Thin current listing activity makes it hard to pin down a reliable price benchmark at any given moment.
Sweet Spot
A buyer or seller comfortable pricing off recent closed comps rather than a running community average.
Avoid If
You are shopping specifically for a community with a documented amenity package like a pool or clubhouse.

A quiet, low-frills villa product

The villa format itself is the headline here more than any shared amenity package. Attached or paired homes like this typically mean a smaller footprint, less exterior upkeep, and a homeowners' association structure that handles at least some of the grounds and building exterior — though buyers should confirm exactly what's covered unit by unit, since that split is not uniform across every villa community in the area.

With no amenities identified from current MLS listings, this is not a community to shop for a pool, a fitness room, or organized common space. It's a fit for someone who wants a smaller, lower-maintenance home in Kissimmee and is comfortable with a plain, no-frills setup rather than a resort-style package.

The location and the amenities are priced into every listing in Villas At Shaddow Bay. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

In a community this small and this thin on current listing data, the value we add is in digging past the MLS summary — pulling actual closed comps, reading HOA documents line by line for maintenance responsibility, and telling you plainly if the numbers don't support the ask. That kind of on-the-ground verification matters more here than in a large, high-volume community where the data does most of the talking on its own.

Villas At Shaddow Bay in 15 seconds.

Best forBuyers who want a smaller, lower-maintenance home in Kissimmee rather than a large single-family lot.
Biggest advantageThe villa format cuts down on exterior upkeep compared to a standard detached home.
Biggest riskThin current listing activity makes it hard to pin down a reliable price benchmark at any given moment.
Sweet spotA buyer or seller comfortable pricing off recent closed comps rather than a running community average.
Avoid ifYou are shopping specifically for a community with a documented amenity package like a pool or clubhouse.

HOA, CDD & Fees

In short
  • HOA status not on record. Verify any dues before you offer
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Villas At Shaddow Bay sales matched to your home.

What is your Villas At Shaddow Bay home worth?

Get a no-obligation home value based on real comparable sales in Villas At Shaddow Bay, 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 Villas At Shaddow Bay on the map →

Real comps, not an automated estimate.
Buyers wanting a smaller, easier-upkeep home in Kissimmee without a large yard to maintainExcellent fit
Buyers comfortable evaluating price on a unit-by-unit basis rather than leaning on a community-wide averageExcellent fit
Buyers who are not shopping for organized common amenities and are fine with a plain, low-frills setupExcellent fit
Buyers who want a pool, clubhouse, or other documented recreational amenity as part of the purchaseProbably not
Buyers who want a large lot or significant private outdoor spaceProbably not
Buyers who need a high volume of current comps to feel confident pricing quicklyProbably not

Data sources & freshness

Under-contract sharesStellar MLS records, as of 2026-07-12

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.

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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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Common questions about Villas At Shaddow Bay

Where is Villas At Shaddow Bay?

Villas At Shaddow Bay is a community in Kissimmee, Osceola County, Florida.

Are there homes for sale in Villas At Shaddow Bay right now?

No active listings inside Villas At Shaddow Bay at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.

Does Villas At Shaddow Bay have an HOA or CDD?

No HOA is on record for Villas At Shaddow Bay in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.

Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.

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