Overoaks
Homes for Sale in Kissimmee, FL
All 2,920 homes for sale in Kissimmee, FL · median $374,990 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 29 closed sales in Overoaks Rep 01 in Kissimmee, FL since 2015, the most recent in September 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).
Overoaks Rep 01 is a built-out early-2000s pocket in Kissimmee, with homes dating from 1996 to 2005 and a median build year around 2001. At a median of roughly 2,574 living square feet, this is a larger-format community, so what sets price here is less about square footage and more about condition and updates. Two homes of the same footprint can sit far apart on price depending on whether the kitchen, baths, roof, and systems have been touched since original construction.
With 319 homes and a homestead share near 61%, this is a predominantly owner-occupied enclave rather than a rental-heavy one. That tends to mean steadier inventory and fewer distressed listings, but it also means a seller should not expect a bidding frenzy off scarcity alone. Buyers should price to condition, and sellers should invest where it shows. The closing window here is thin, so read individual comps carefully rather than leaning on broad averages.
Nearby homes for sale
No active listings inside Overoaks Rep 01 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
Overoaks Rep 01 is an established, owner-heavy neighborhood of larger early-2000s homes in Osceola County, where the spread in value is driven far more by updates and upkeep than by floor plan or age.
Stellar MLS sales records identify 94 homes in Overoaks that have changed hands since 2004, built between 1987 and 2005 (median 1997), with a median living area of about 2,249 sq ft and a typical 4-bedroom, 3-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 Overoaks is best for.
Best for
- Buyers seeking a larger floor plan around 2,574 square feet in an established Kissimmee setting
- Buyers comfortable budgeting for updates in exchange for a lower condition-adjusted price
- Long-hold owner-occupants who value an owner-heavy, low-turnover neighborhood
Probably not for
- Buyers who require new construction or the newest systems and finishes
- Buyers on a tight budget who cannot absorb potential roof or HVAC replacement
- Investors chasing high rental turnover, given the strong owner-occupied share
The market around Overoaks
Overoaks is too small for its own price trend, so here is the market around it.
In ZIP 34746, 975 homes are on the market and 17% 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 34746 (Kissimmee), 1,615 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.5% year over year, with a median 67 days on market. Right now 421 active and 72 pending listings put supply at about 6.7 months — a buyer's market. See the live ZIP 34746 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not Overoaks specifically. Momentum Research analysis of MLS records.
The Overoaks buying strategy.
If we were buying in Overoaks 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 Overoaks.
Condition is the real variable
When a community is this uniform in vintage — clustered around 2001, with a tight 1996 to 2005 range — the homes themselves are not the differentiator. What separates a strong sale from a soft one is what has happened inside since original construction: roof age, HVAC, kitchens, and baths. At a median near 2,574 square feet, these are substantial homes, and substantial homes carry substantial deferred-maintenance risk when systems reach their natural replacement age.
For buyers, that argues for a disciplined inspection and a hard look at what has and has not been replaced. For sellers, it means the return on visible, verifiable updates is real here. Because the closing window is narrow, do not anchor to a single recent sale in either direction; the pricing evidence is thin enough that condition-adjusted comparison beats headline numbers every time.
The location and the amenities are priced into every listing in Overoaks. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a thin-turnover, condition-driven neighborhood like this, the difference between an accurate price and a guess is field knowledge. We underwrite each home on its actual updates and systems rather than a per-square-foot average, and we will tell a seller candidly where the money should go before listing — and tell a buyer just as candidly when a listing is priced for a condition it does not have.
Overoaks 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 Overoaks 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 Overoaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Overoaks, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Overoaks home worth?
Get a no-obligation home value based on real comparable sales in Overoaks, 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 Overoaks?
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 2015 (29 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 Overoaks Rep 01 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Overoaks
Where is Overoaks?
Overoaks is a community in Kissimmee, Osceola County, Florida, ZIP 34746.
Are there homes for sale in Overoaks right now?
No active listings inside Overoaks at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Overoaks have an HOA or CDD?
No HOA is on record for Overoaks 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 Overoaks with Momentum Realty’s local guides.