Shenandoah
Homes for Sale in Kissimmee, FL
All 2,933 homes for sale in Kissimmee, FL · median $373,400 · 247 homes for sale in 34744 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 19 closed sales in Shenandoah Unit 2 in Kissimmee, FL since 2006, the most recent in August 2025. 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).
Shenandoah Unit 2 is a small, established pocket of 93 homes built across a tight window from 1979 to 1982. That age and consistency matter: floor plans and lot layouts are broadly similar, so what actually sets one home's price apart from the next is condition and updating, not square footage swings. The median home runs about 1,483 living square feet, which puts this squarely in the modest-footprint tier of Osceola County.
Because the stock is uniform in vintage, expect a wide spread in what sellers ask depending on how much work a home has absorbed over four-plus decades. Updated systems, roofs, and interiors command a premium here; deferred maintenance gets discounted hard. For buyers, that means the negotiation is a condition conversation. For sellers, the path to the top of the market is renovation receipts, not just a fresh listing.
Nearby homes for sale
No active listings inside Shenandoah Unit 2 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.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
This is a compact, single-era community in Kissimmee where homes share a common build period and a modest footprint. With just 93 homes, turnover is limited, so serious buyers should be ready to move when the right condition comes available.
Stellar MLS sales records identify 56 homes in Shenandoah that have changed hands since 2004, built between 1980 and 2004 (median 1980), with a median living area of about 1,188 sq ft and a typical 3-bedroom, 2-bath layout; 100% 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.
Who Shenandoah is best for.
Best for
- Buyers targeting a modest-footprint home around 1,483 square feet who plan to occupy it themselves
- Renovation-minded buyers willing to trade a dated home for a lower entry point and do the work
- Buyers who value an established, low-turnover community over amenities and newness
Probably not for
- Buyers who want new or newer construction and modern floor plans
- Buyers needing significant square footage above the modest median here
- Buyers unwilling to budget for potential updates on a home built around 1980
The market around Shenandoah
Shenandoah is too small for its own price trend, so here is the market around it.
In ZIP 34744, 418 homes are on the market and 21% are under contract — a steady corner of Kissimmee.
Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).
In ZIP 34744 (Kissimmee), 785 homes closed in the last 12 months at a median of $406K ($215/sq ft), up 1.8% year over year, with a median 34 days on market. Right now 126 active and 26 pending listings put supply at about 6.6 months — a balanced market. See the live ZIP 34744 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not Shenandoah specifically. Momentum Research analysis of MLS records.
The Shenandoah buying strategy.
If we were buying in Shenandoah 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 Shenandoah.
A single-vintage enclave where condition is the whole story
Homes here were built between 1979 and 1982, with the median year landing at 1980. Four-plus decades in, the meaningful questions are about the roof, the HVAC, the electrical panel, and whether major updates have been done. Two homes of nearly identical size can price very differently based purely on how they've been maintained and modernized.
The owner-occupancy signal is notable: roughly 68% of homes carry a homestead exemption. That points to a community held largely by people living in their homes rather than a heavy investor or rental concentration, which tends to correlate with steadier upkeep and a more stable resale environment. At 1,483 median living square feet, these are right-sized homes rather than sprawling ones.
The location and the amenities are priced into every listing in Shenandoah. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a 93-home community where price is driven by condition rather than size, our job is to read the difference between a home that's been genuinely updated and one that's been staged to look that way. We walk the systems, price against the specific median profile of this neighborhood, and tell you plainly when an asking price assumes work that hasn't been done.
Shenandoah in 15 seconds.
HOA, CDD & Fees
- 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.
Tools for a Shenandoah 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 Shenandoah sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Shenandoah, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Shenandoah home worth?
Get a no-obligation home value based on real comparable sales in Shenandoah, 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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Should you buy in Shenandoah?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2006 (19 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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See how Shenandoah Unit 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Shenandoah
Where is Shenandoah?
Shenandoah is a community in Kissimmee, Osceola County, Florida, ZIP 34744.
Are there homes for sale in Shenandoah right now?
No active listings inside Shenandoah at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Shenandoah have an HOA or CDD?
No HOA is on record for Shenandoah 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 Shenandoah with Momentum Realty’s local guides.