Shenandoah
Homes for Sale in Kissimmee, FL
All 3,127 homes for sale in Kissimmee, FL · median $375,000 · 329 homes for sale in 34744 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 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, 4,246 homes closed in the last 12 months at a median of $360,000, 64 median days on market, with 2,907 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,480 ($4,880 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.
Figures in this note are as of July 14, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside ShenandoahHomes for Sale in Kissimmee, FL 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.
County records show 6 qualified sales in Shenandoah across 2024–2025 (4 in 2024, 2 in 2025), median $295,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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, 447 homes are on the market and 19% are under contract — a steady corner of Kissimmee.
Across Osceola County, 4,465 homes are active and 1,093 pending (20% under contract).
In ZIP 34744 (Kissimmee), 271 homes closed in the last 12 months at a median of $390K ($212/sq ft), up 5.3% year over year, with a median 36 days on 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.
See all homes for sale in Kissimmee →
| Location | Kissimmee, Osceola County, FL · ZIP 34744 |
|---|---|
| Homes in the community | 134 (FL DOR 2025 assessment roll) |
| Years built | 1979–2004 (median 1980.0) |
| Typical living area | 1,383 sq ft (median) |
| Owner-occupied (homestead) share | 66% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Shenandoah key facts,” movewithmomentum.com/neighborhoods/shenandoah-unit-2, data as of September 20, 2026.
Housing distress & ownership in Shenandoah Unit 2, 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 September 2026 through September 2026. Deemed reliable but not guaranteed.
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Kissimmee guides & data
- Market data
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- Flood zones
- Property taxes (Osceola County)
- Homestead exemption (Osceola County)
- Home insurance cost
Florida buyer guides
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- Florida property tax calculator
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- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
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- Florida documentary stamp tax, explained
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Ask an agent about Shenandoah
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Recent Developments in Shenandoah Unit 2
Development, infrastructure, retail, and school activity affecting Shenandoah Unit 2, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Parks & Amenities
145,000 sq ft All Sports Dome planned on Gus Road in Kissimmee
All Sports Dome Southeast plans a climate-controlled indoor inflatable dome at 3070 Gus Road with multi-sport courts, turf fields and training areas. It would be the brand's first Greater Orlando location, with an opening expected in 2027 and no exact date given.
What it may mean for the marketAn indoor sports venue would add year-round recreation and event space on Kissimmee's Gus Road area. The project is about 3 miles southwest of Shenandoah Unit 2, elsewhere in Osceola County.
Source: What Now Orlando - October 2026Infrastructure
Turnpike widening in Osceola County runs ahead of schedule at Fortune Road Bridge
Steel beams for the new westbound Fortune Road Bridge are in place a month early as Florida's Turnpike is widened from two to four lanes each way between Partin Settlement Road and Osceola Parkway. Westbound bridge traffic is expected at the start of 2027, and the broader project targets 2031. The bridge adds bike lanes and sidewalks.
What it may mean for the marketDoubling Turnpike capacity through this stretch should ease regional commutes between Kissimmee and the Orlando area once complete. The site is about 1 mile east of Shenandoah Unit 2.
Source: WFTV - October 2026Development
Experience Kissimmee launches Film Kissimmee commission to recruit productions
The new film commission markets Osceola County to production companies through an online database of more than 100 filming locations and has hired a location manager. Leaders say productions could become a new economic driver, citing spending on hotels, vehicles, food and crew services.
What it may mean for the marketFilm work could add temporary jobs and visitor spending for hospitality and service businesses across Osceola County. The site is less than a mile south of Shenandoah Unit 2.
Source: WFTV - September 2026Development
Orange County commissioners approve Tuscana land use plan in Shingle Creek Basin on 4-3 vote
Commissioners voted 4-3 to approve the Tuscana land use application from Shingle Creek Co-Owners LLC and Geyer Development, reversing a unanimous rejection in May 2025. The plan includes more than 1,000 hotel rooms, about 4,000 apartments and commercial buildings, with conditions for a raised road, flood mitigation and wetland protection.
What it may mean for the marketThe approval could add substantial rental housing, hotel capacity and commercial space in the Shingle Creek area, while flood-mitigation conditions will shape how and when it is built. The site is about 7 miles northwest of Shenandoah Unit 2.
Source: Spectrum News 13 - August 2026Retail & Dining
Plans for Mattel indoor water park near Lake Buena Vista Factory Stores expand to 13 acres
Updated plans for the site off State Road 535 show a 95,000-square-foot indoor water park designed by Martin Aquatic, a separate 45,000-square-foot entertainment building and nearly 900 parking spaces. The tower height rises to as much as 100 feet and still needs Orange County approval. About 200 jobs are expected, and no opening date has been announced.
What it may mean for the marketThe project would add visitor attractions, dining and roughly 200 jobs near the State Road 535 corridor, with added traffic and parking demand nearby. The site is about 10 miles northwest of Shenandoah Unit 2.
Source: FOX 35 Orlando - March 2026Development
Orlando approves the 380-acre Dowden Central Community Development District in Lake Nona
Orlando approved the Dowden Central Community Development District, a roughly 380-acre district in the Lake Nona area of southeast Orlando, in March 2026. The district provides the framework to build roads, drainage, utilities, and parks for future development phases.
What it may mean for the marketA new community development district lays the groundwork for large-scale growth in the Lake Nona area, a step that typically precedes new housing and commercial activity nearby. The site is about 10 miles northeast of Shenandoah Unit 2.
Source: ClickOrlando
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
Frequently Asked Questions
How many homes are in Shenandoah?
What share of Shenandoah is owner-occupied?
When were the homes in Shenandoah built?
Who is the best real estate agent for Shenandoah?
How do I find a top Kissimmee real estate agent who knows Shenandoah?
Can Momentum Realty connect me with an agent for Shenandoah?
Where is Shenandoah, and what county is it in?
Should you buy in Shenandoah?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Housing stock & ownership | Florida DOR assessment roll (street-list match (5 streets, ZIP 34744)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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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