Sherwood Forest
Homes for Sale in Kissimmee, FL
All 3,081 homes for sale in Kissimmee, FL · median $375,000 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of November 2026, Sherwood Forest in Kissimmee, FL has 1 home for sale. Sherwood Forest is a community in Kissimmee, Osceola County, FL. Across Kissimmee as a whole, 4,248 homes closed in the last 12 months at a median of $360,000, 64 median days on market, with 2,898 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).

Sherwood Forest is a small, quiet pocket in Kissimmee with no standout community amenities pulling on price, so value here comes down to the individual home - condition, updates, lot, and layout do the work that a pool or clubhouse might elsewhere. With no shared amenity story to lean on, the house itself has to carry the sale.
The posture is clearly buyer-leaning. At 12 months of supply and only one active listing as of September 2026, there is almost nothing on the shelf, which cuts both ways: a buyer has leverage in a slow-moving market, but there is little to choose from, and a seller priced ahead of condition can sit. Patience matters more than urgency on both sides.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Sherwood Forest right now
🟢 Buyer-leaning market. 12.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.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 September 16, 2026. Confidence: Low (1 active and pending listings, 0 closed sales in 12 months).
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· Updated November 8, 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
Sherwood Forest is a modest residential enclave in Kissimmee, Osceola County, where the market moves slowly and the inventory is thin - a place to evaluate one home at a time rather than shop a broad field.
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 Sherwood Forest is best for.
Best for
- Buying to hold for the long term in a quiet, low-turnover area
- Buyers who want time to inspect and negotiate without competing offers
- Buyers willing to focus on one home's condition and merits rather than a broad field
Probably not for
- Needing a wide selection of listings to compare right now
- Wanting a quick in-and-out with fast resale and deep comps
- Expecting shared community amenities like a pool or clubhouse
The market around Sherwood Forest
Sherwood Forest is too small for its own price trend, so here is the market around it.
Across Osceola County, 4,437 homes are active and 1,077 pending (20% under contract).
ZIP and county figures describe the wider market, not Sherwood Forest specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Sherwood Forest
Live MLS inventory for Sherwood Forest. 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 Sherwood Forest listings as of 2026-06-22, priced high to low. Based on Stellar MLS data distributed by MLS GRID. Tap any home to ask about it.
The Sherwood Forest buying strategy.
If we were buying in Sherwood Forest 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 Sherwood Forest.
A thin, condition-driven market
Twelve months of supply with a single active listing tells you most of what you need to know about tempo: this is not a community where homes trade quickly, and the sample size is small enough that any one sale can move the picture. Because no community amenities surface from current MLS listings, there is no shared feature setting a floor under values - pricing follows the merits of each individual property.
For a buyer, that means time to inspect, compare against condition, and negotiate without competing offers breathing down your neck. For a seller, it means the home has to be genuinely ready and realistically priced, because there is no amenity narrative and no fast-moving market to carry a stretch.
The location and the amenities are priced into every listing in Sherwood Forest. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a thin, slow-moving market like this, the value is in reading one property correctly rather than surfing a wave of comparable sales. We help buyers judge a home on its own condition and merits, and we help sellers price to the reality of a buyer-leaning market instead of hoping activity shows up to rescue an ambitious number.
Sherwood Forest in 15 seconds.
Tools for a Sherwood Forest 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 Sherwood Forest sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Sherwood Forest, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Sherwood Forest home worth?
Get a no-obligation home value based on real comparable sales in Sherwood Forest, 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 →
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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
- How to stop a foreclosure in Florida
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Email me new listings in Sherwood Forest
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Sherwood Forest
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Sherwood Forest will answer, and the answer is published on this page for the next buyer.
16% of homes for sale in ZIP 34746 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-29).
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Osceola County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Osceola County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
Frequently Asked Questions
Is Sherwood Forest a buyer's or seller's market right now?
Who is the best real estate agent for Sherwood Forest?
How do I find a top Kissimmee real estate agent who knows Sherwood Forest?
Can Momentum Realty connect me with an agent for Sherwood Forest?
Where is Sherwood Forest, and what county is it in?
Should you buy in Sherwood Forest?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: June 22, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-12 |
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.
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. A Momentum agent can price yours against live local comps.
Looking to buy here? Search homes for sale →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Sherwood Forest fits the bigger picture — live prices, inventory, and Momentum Scores:

