Shadow Bay
Homes for Sale in Kissimmee, FL

All 2,933 homes for sale in Kissimmee, FL · median $373,400 · 173 homes for sale in 34741 · Osceola County homes for sale

Community in Kissimmee · Osceola County · ZIP 34741
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Built fromLive Stellar MLS data20 years of closingsUpdated twice daily

As of September 2026, the MLS records 49 closed sales in Shadow Bay Unit 4 in Kissimmee, FL since 2006, the most recent in October 2025. Recorded prices since 2024 ran from $282,000 to $450,000 (median $365,000), on homes of 1,590 to 2,124 sq ft. 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 $5,560 ($4,960 with the full homestead exemption).

Live · Shadow Bay Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
1
Sold · last 12 mo
10-yr average: about 3 a year
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Shadow Bay Unit 4 is a tight, single-phase subdivision built out between 1984 and 1989, with a median build year of 1987. That means most of the housing stock is now well into its fourth decade, so condition and updates — roof age, HVAC, kitchens, windows — do more to separate one listing from another than location within the community does. Two buyers looking at homes a few doors apart can be looking at very different renovation timelines.

With 230 homes total and just over half (54.3%) recorded as homesteaded, this reads as a community with a meaningful base of longer-term owners rather than a rotating rental or investment pool, though it is not exclusively one or the other. The recent closings window is short, which means pricing conclusions should be drawn carefully and updated as new sales post rather than anchored to older comps.

Nearby homes for sale

No active listings inside Shadow Bay Unit 4 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.

2331 PEPPERCORN STREET
$410K · 0.0 mi away
3 bd · 2 ba · 1,769 sqft
2331 PEPPERCORN STREET
Listed by KELLER WILLIAMS REALTY SMART
2207 CARIBBEAN DRIVE
$195K · 0.1 mi away
2 bd · 2 ba · 991 sqft
2207 CARIBBEAN DRIVE
Listed by AGENT TRUST REALTY CORPORATION
2342 BARBADOS COURT
$230K · 0.2 mi away
2 bd · 2 ba · 991 sqft
2342 BARBADOS COURT
Listed by FLORIDA FANTASY REAL ESTATE INC
2121 AVIAN LOOP
$460K · 0.2 mi away
4 bd · 2.5 ba · 2,176 sqft
2121 AVIAN LOOP
Listed by LA ROSA REALTY KISSIMMEE
2123 ST MARTEEN COURT
$195K · 0.2 mi away
2 bd · 2 ba · 991 sqft
2123 ST MARTEEN COURT
Listed by LPT REALTY, LLC
2718 RIO GRANDE TRAIL #2718
$180K · 0.2 mi away
3 bd · 2 ba · 1,250 sqft
2718 RIO GRANDE TRAIL #2718
Listed by CASAQUIERO LLC

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

The 60-Second Overview

Shadow Bay Unit 4 in Kissimmee is a 1980s-built subdivision of 230 homes with a median living area of 1,579 square feet — a scale and footprint typical of established Osceola County neighborhoods from that era, without an on-record amenity package tied to the community itself.

Stellar MLS sales records identify 83 homes in Shadow Bay that have changed hands since 2004, built between 1984 and 2006 (median 1985), with a median living area of about 1,900 sq ft and a typical 3-bedroom, 2-bath layout; 98% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

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 who want a modest-footprint, established home and are comfortable evaluating condition on a house-by-house basis.
  • Buyers focused on long-term ownership who are not seeking a bundled amenity package.
  • Buyers with renovation budget or plans who can take advantage of the wide condition spread across 1980s-built homes.

Probably not for

  • Buyers who want move-in-ready systems with no inspection contingencies given the community's age.
  • Buyers whose priority is on-site recreational amenities, since none are currently identified.
  • Buyers seeking larger, newer-build square footage rather than a compact 1980s floor plan.

The market around Shadow Bay

Shadow Bay is too small for its own price trend, so here is the market around it.

In ZIP 34741, 299 homes are on the market and 15% are under contract — a slower corner of Kissimmee.

Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).

In ZIP 34741 (Kissimmee), 745 homes closed in the last 12 months at a median of $411K ($205/sq ft), down 2.2% year over year, with a median 44 days on market. Right now 201 active and 47 pending listings put supply at about 6.0 months — a balanced market. See the live ZIP 34741 housing market and the Osceola County market.

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

If we were buying in Shadow 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 Shadow Bay.

Best Buy
Buyers prioritizing an established, mid-size Kissimmee home over a community amenity package.
Biggest Risk
Age-driven condition variance is the main risk, since most homes date to the mid-to-late 1980s.
Sweet Spot
Homes with documented system updates that offset the 1987 median build year.
Avoid If
Avoid if you are specifically shopping for community amenities like a pool or clubhouse, since none are identified here.

A 1987 build year sets the terms

The build window of 1984 to 1989, with a median of 1987, is the single most important fact about this community. Homes of this vintage are old enough that major systems — roofs, water heaters, HVAC — are commonly past or approaching their second replacement cycle. Buyers should expect to budget for inspection findings and treat unrenovated listings differently in negotiation than turnkey ones, even within the same square footage range.

At a median of 1,579 square feet, the homes here sit in a modest, efficient footprint rather than sprawling floor plans, which keeps maintenance and utility scope proportionate. No community amenities are identified in current MLS listings, so this is a neighborhood to evaluate on the house and lot itself — not on a clubhouse, pool, or recreation package — and any amenity value should be verified directly rather than assumed.

The location and the amenities are priced into every listing in Shadow 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 built across a narrow five-year window with no shared amenity draw, the work is in the details — matching a buyer to a home's actual condition, age of systems, and true comparable set rather than a general neighborhood price. We track closings here as they post, not on a stale quarterly basis, so pricing guidance reflects what is actually happening on the ground right now.

Shadow Bay in 15 seconds.

Best forBuyers prioritizing an established, mid-size Kissimmee home over a community amenity package.
Biggest advantageA manageable footprint — a median 1,579 square feet keeps carrying costs and maintenance scope in check.
Biggest riskAge-driven condition variance is the main risk, since most homes date to the mid-to-late 1980s.
Sweet spotHomes with documented system updates that offset the 1987 median build year.
Avoid ifAvoid if you are specifically shopping for community amenities like a pool or clubhouse, since none are identified here.

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 Shadow Bay sales matched to your home.

What is your Shadow Bay home worth?

Get a no-obligation home value based on real comparable sales in Shadow 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.

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Real comps, not an automated estimate.
Buyers who want a modest-footprint, established home and are comfortable evaluating condition on a house-by-house basis.Excellent fit
Buyers focused on long-term ownership who are not seeking a bundled amenity package.Excellent fit
Buyers with renovation budget or plans who can take advantage of the wide condition spread across 1980s-built homes.Excellent fit
Buyers who want move-in-ready systems with no inspection contingencies given the community's age.Probably not
Buyers whose priority is on-site recreational amenities, since none are currently identified.Probably not
Buyers seeking larger, newer-build square footage rather than a compact 1980s floor plan.Probably not

Data sources & freshness

Under-contract sharesStellar MLS records, as of 2026-09-08
Historical depthClosed-sale records back to 2006 (49 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.

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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 local comps.

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CallFree valuation →
Thinking of selling in Shadow Bay Unit 4? 1 recorded closings (window ending 2026-09-12). See the Osceola County sell-now-or-wait data, what made 201,552 Florida listings fail in the last 12 months, or compare a cash offer vs. listing. Compiled from MLS records; deemed reliable but not guaranteed.

Common questions about Shadow Bay

Where is Shadow Bay?

Shadow Bay is a community in Kissimmee, Osceola County, Florida, ZIP 34741.

Are there homes for sale in Shadow Bay right now?

No active listings inside Shadow 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 Shadow Bay have an HOA or CDD?

No HOA is on record for Shadow 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.

Nearby Communities

Explore more neighborhoods near Shadow Bay with Momentum Realty’s local guides.

CVCaribbean Villas0.1 mi away · 1 for saleCVCaribbean Villas Condo0.2 mi awayCVCaribbean Villas Condo0.2 mi awayCVCaribbean Villas Condo Phs A F0.2 mi awayTVThe Villas At Shadow Bay0.3 mi away · 17 homes, built 1986–86, 1 for saleCKCascades Kissimmee Condo0.4 mi awayCACascades At Kissimmee Condo0.4 mi away

Browse all neighborhood guides →

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