Oak Island Harbor
Homes for Sale in Kissimmee, FL
All 3,127 homes for sale in Kissimmee, FL · median $375,000 · 960 homes for sale in 34747 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of November 2026, the MLS records 1 closed sale in Oak Island Harbor in Kissimmee, FL, the most recent in April 2026. 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).
Oak Island Harbor is an established Kissimmee community of 122 homes built between 1992 and 2013, with the typical home dating to the late 1990s and running just under 2,350 square feet. At this age and size, price here is driven far more by condition and updates than by any single list number. Two homes on the same street can trade well apart depending on roof, systems, and how much of the original interior remains.
Only about a third of the homes carry a homestead exemption, which tells you a meaningful share are held as second homes or rentals rather than owner-occupied. That shapes the resale pool: expect a wider spread in upkeep and finish level, and negotiate on the specific house in front of you rather than a neighborhood average. Sellers who have genuinely updated should document it; buyers should budget for inspection findings on the older stock.
Figures in this note are as of July 13, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Oak Island HarborHomes 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 mature, mid-1990s-vintage community with generously sized homes, where the mix of owner-occupied and non-homestead properties means condition varies house to house.
Stellar MLS sales records identify 38 homes in Oak Island Harbor that have changed hands since 2005, built between 1992 and 1998 (median 1996), with a median living area of about 2,045 sq ft and a typical 4-bedroom, 2.5-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 9 qualified sales in Oak Island Harbor across 2024–2024, median $454,000 — 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 Oak Island Harbor is best for.
Best for
- Buyers prioritizing living space and willing to trade newest-build for more square footage
- Renovation-minded buyers who can price in and manage updates on an older home
- Investors underwriting a specific property on condition and rental fundamentals
Probably not for
- Buyers who want new construction or the latest floor plans
- Buyers unwilling to budget for potential roof and systems work on 1990s-era homes
- Buyers expecting every home on the block to be finished to the same standard
The market around Oak Island Harbor
Oak Island Harbor is too small for its own price trend, so here is the market around it.
In ZIP 34747, 1,277 homes are on the market and 12% are under contract — a slower corner of Kissimmee.
Across Osceola County, 4,465 homes are active and 1,093 pending (20% under contract).
In ZIP 34747 (Kissimmee), 1,203 homes closed in the last 12 months at a median of $470K ($220/sq ft), down 3.0% year over year, with a median 75 days on market. Right now 447 active and 67 pending listings. See the live ZIP 34747 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not Oak Island Harbor specifically. Momentum Research analysis of MLS records.
The Oak Island Harbor buying strategy.
If we were buying in Oak Island Harbor 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 Oak Island Harbor.
An established community, priced by condition
The build window closed over a decade ago, so there is no new construction to compete with resale here. The value question is straightforward: has a given home kept pace with its age? On homes built in the 1990s, roof age, HVAC, water heater, and kitchen and bath updates separate the strong listings from the ones that will sit. The living space is on the larger side for the era, which gives updated homes real appeal and gives dated ones more square footage to modernize.
The lower homestead share is the number to sit with. With roughly a third owner-occupied, the remainder skews toward investment and seasonal use, which can mean deferred maintenance in some cases and turnkey rental-grade finishes in others. Neither is good or bad on its own; it just means you underwrite each property individually and lean on inspection rather than assuming the block sets the standard.
The location and the amenities are priced into every listing in Oak Island Harbor. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community where condition, not a headline number, sets value, our job is to read the specific house: what has been updated, what is deferred, and where the negotiation leverage actually sits. We price and inspect on the merits of the individual home rather than a neighborhood shorthand, which matters most in older stock with a mixed ownership profile.
Oak Island Harbor in 15 seconds.
Email me new listings in Oak Island Harbor
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 Oak Island Harbor
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Oak Island Harbor will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $648/year (about $54/month) · median of 32 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $648 a year ($54 a month) — the median AssociationFee across 32 MLS records, normalised to a monthly figure; most are billed annually. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.
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 Oak Island Harbor 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 Oak Island Harbor sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oak Island Harbor, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Oak Island Harbor home worth?
Get a no-obligation home value based on real comparable sales in Oak Island Harbor, 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 34747 |
|---|---|
| Homes in the community | 122 (FL DOR 2025 assessment roll) |
| Years built | 1992–2013 (median 1997.0) |
| Typical living area | 2,348 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 34% |
Data as of November 13, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2026 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Oak Island Harbor key facts,” movewithmomentum.com/neighborhoods/oak-island-harbor, data as of November 13, 2026.
Housing distress & ownership in Oak Island Harbor, 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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- Best neighborhoods
- Flood zones
- Property taxes (Osceola County)
- Homestead exemption (Osceola County)
- Home insurance cost
Florida buyer guides
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- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- 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
- Florida documentary stamp tax, explained
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Formosa Boulevard (13 homes on record)
- Drifting Lilly Loop (13 homes on record)
Recent Developments in Oak Island Harbor
Development, infrastructure, retail, and school activity affecting Oak Island Harbor, 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 5 miles southwest of Oak Island Harbor, 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 less than a mile northwest of Oak Island Harbor.
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 about 2 miles west of Oak Island Harbor.
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 8 miles northwest of Oak Island Harbor.
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 11 miles northwest of Oak Island Harbor.
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 9 miles northeast of Oak Island Harbor.
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 Oak Island Harbor?
What share of Oak Island Harbor is owner-occupied?
When were the homes in Oak Island Harbor built?
Who is the best real estate agent for Oak Island Harbor?
How do I find a top Kissimmee real estate agent who knows Oak Island Harbor?
Can Momentum Realty connect me with an agent for Oak Island Harbor?
Where is Oak Island Harbor, and what county is it in?
Should you buy in Oak Island Harbor?
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: November 2, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (5 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2014 (28 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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