Harbour Oaks
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

Community in Kissimmee · Osceola County · ZIP 34744
Median sale $520K
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Built fromLive Stellar MLS data14 years of closingsUpdated twice daily

Over the 12 months ending 2026-09-12, 6 recorded sales closed at a median of $520,000, $229 per square foot, a median 99 days on market, sellers accepting 98% of original asking (+40% versus the prior year). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $7,920 ($7,320 with the full homestead exemption).

Live · Harbour Oaks Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Price
$520K
Median sold · 12 mo
up 40.5% vs the prior 12 months
+40.5%
1-yr price change
n = 6 and 3 sales in the two windows
$229/sf
Sold $/sqft · 12 mo
peak $229 in 2026
97.7%
Sale vs ask
Osceola median: 95.9%
Tempo
100days
Median DOM · closed
5 days at the 2025 low
6
Sold · last 12 mo
10-yr average: about 1 a year
Track record · 14 years of records
2,175sqft
Median sold home size
12-mo windows, closed sales
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Harbour Oaks Unit 1 is a value-per-square-foot story more than a scarcity story. At a median of $242.26 per square foot against a median living area of 2,894 square feet, the math on these homes is about interior space first, condition and updates second. With a year-built span running from 1928 to 2024 but a median year built of 1982, this is not a uniform-vintage subdivision — buyers are pricing individual homes on their own merits rather than leaning on a single build era as a shorthand for condition.

A median 48 days on market is a moderate pace, not a bidding-war pace. That gives buyers room to negotiate on condition and gives sellers a reason to price tightly to the comparable range rather than testing the market. With 85.9% of homes carrying a homestead exemption, the majority of this inventory is owner-occupied, which tends to show up as more day-to-day maintenance variance than an investor-owned block would, and it's worth underwriting accordingly on a home-by-home basis.

Harbour Oaks Housing Pulse · Momentum Research · as of September 12, 2026

Harbour Oaks right now

🟢 Still climbing. The trailing-12-month median ($520K) is up 40.5% from the prior 12 months ($370K). With about 1 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 12. Confidence: Low (6 and 3 sales in the two windows).

Jump to: Price history & scorecard · Homes for sale · Schools · FAQ

· Updated September 15, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness

Nearby homes for sale

No active listings inside Harbour Oaks Unit 1 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.

1495 SKYLINE DRIVE
$450K · 0.1 mi away
3 bd · 2 ba · 2,094 sqft
1495 SKYLINE DRIVE
Listed by MACERA REALTY GROUP INC
1516 PINE ISLAND ROAD
$849K · 0.1 mi away
4 bd · 2.5 ba · 2,613 sqft
1516 PINE ISLAND ROAD
Listed by KEN BAKER REAL ESTATE
1592 SKYLINE DRIVE
$560K · 0.2 mi away
3 bd · 2.5 ba · 2,410 sqft
1592 SKYLINE DRIVE
Listed by LPT REALTY, LLC
1632 REGAL COVE COURT
$1.07M · 0.2 mi away
6 bd · 5.5 ba · 4,621 sqft
1632 REGAL COVE COURT
Listed by FIERCE REALTY
1860 SAHA COURT
$653K · 0.3 mi away
4 bd · 3 ba · 2,869 sqft
1860 SAHA COURT
Listed by DEESE MANAGEMENT & REAL ESTATE
1540 GRANDVIEW BOULEVARD
$899K · 0.3 mi away
4 bd · 4.5 ba · 5,207 sqft
1540 GRANDVIEW BOULEVARD
Listed by EAST PARK REALTY LLC

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

The 60-Second Overview

Harbour Oaks market snapshot (as of September 12, 2026): the median sale price is about $520K ($229 per sq ft over the trailing 12 months of closed sales), and a median 100 days on market for closed sales. The trailing-12-month median is up 40% from the prior 12 months, computed from record-level Stellar MLS closed sales (6 closings in the current window).

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.

Stellar MLS sales records identify 61 homes in Harbour Oaks that have changed hands since 2004, built between 1973 and 2002 (median 1980), with a median living area of about 2,094 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.

Harbour Oaks Unit 1 in Kissimmee (Osceola County) is a 177-home community where the housing stock spans nearly a century of construction, anchored by a median build year of 1982 and a median home size of 2,894 square feet — large-format living space is the constant here even as architectural era varies widely.

Best for

  • Buyers prioritizing square footage and willing to budget for condition-specific inspections
  • Buyers comfortable evaluating homes individually rather than relying on a uniform build standard
  • Buyers focused on a straightforward single-family purchase without an amenity requirement

Probably not for

  • Buyers who want a community built and sold around shared recreational amenities
  • Buyers seeking a single, uniform architectural era or consistent renovation timeline across the neighborhood
  • Buyers expecting a fast, high-competition turnaround at listing given the moderate median days on market

Windows contain 0 to 6 sales each (6 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2012 through 2026. Deemed reliable but not guaranteed.

Homes sold per 12-mo window
024620122014201620182020202220242026
0 to 6 a year; 6 in the current window.
How much local inventory is already under contract

21% of homes for sale in ZIP 34744 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 (2026-09-08).

If we were buying in Harbour Oaks today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Harbour Oaks.

Best Buy
Buyers who want a larger floor plan and are comfortable evaluating each home on its own condition rather than a uniform community standard.
Biggest Risk
The wide year-built range means mechanical age and renovation history vary sharply from one address to the next.
Sweet Spot
Homes built closer to the 1982 median where updates and original systems are easiest to assess against comparable sales.
Avoid If
You are shopping specifically for a community with organized shared amenities, since none are identified here.

A wide build range, priced individually

The spread from 1928 to 2024 in year built means Harbour Oaks Unit 1 is not a tract-built subdivision with one dominant look and one dominant maintenance profile. A median year built of 1982 puts the typical home at a stage where mechanical systems, roofs, and finishes are squarely a due-diligence item rather than an assumption, and the presence of homes at both much older and much newer ends of that range means inspection findings will vary house to house more than they would in a single-phase development.

No community amenities have been identified from current MLS listings, so buyers should treat this as a straightforward single-family setting rather than an amenity-driven purchase — the value proposition here is the home and the lot, not a shared clubhouse or recreation package. At $492,000 median price and a median 48 days on market, pricing discipline tied to condition and square footage will do more for a seller than marketing around amenities that aren't part of the package.

The location and the amenities are priced into every listing in Harbour Oaks. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

In a community with this much variation in build year and no shared amenity package to lean on, pricing a home correctly means comparing it against the right handful of similar-vintage, similar-size sales rather than a blanket neighborhood average — that's the analysis we run before a listing goes live or an offer goes in.

Harbour Oaks in 15 seconds.

Best forBuyers who want a larger floor plan and are comfortable evaluating each home on its own condition rather than a uniform community standard.
Biggest advantageMedian living space of 2,894 square feet gives buyers more room per dollar than a compact-lot community would.
Biggest riskThe wide year-built range means mechanical age and renovation history vary sharply from one address to the next.
Sweet spotHomes built closer to the 1982 median where updates and original systems are easiest to assess against comparable sales.
Avoid ifYou are shopping specifically for a community with organized shared amenities, since none are identified here.

HOA, CDD & Fees

In short
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Harbour Oaks sales matched to your home.

What is your Harbour Oaks home worth?

Get a no-obligation home value based on real comparable sales in Harbour Oaks, 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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Real comps, not an automated estimate.

Frequently Asked Questions

What is the median home price in Harbour Oaks?
The median sale price in Harbour Oaks was $520K over the 12 months ending September 12, 2026 (6 closed sales, Stellar MLS).
How long do homes in Harbour Oaks take to sell?
Homes that closed in the 12 months ending September 12, 2026 took a median 100 days on market (6 sales, Stellar MLS).
Who is the best real estate agent for Harbour Oaks?
The best agent for Harbour Oaks is one who actively works Kissimmee and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Harbour Oaks.
How do I find a top Kissimmee real estate agent who knows Harbour Oaks?
Share a few details in the form on this page. Momentum Realty has 320+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Harbour Oaks and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Harbour Oaks?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Harbour Oaks purchase or sale - no call center and no pressure.
Buyers prioritizing square footage and willing to budget for condition-specific inspectionsExcellent fit
Buyers comfortable evaluating homes individually rather than relying on a uniform build standardExcellent fit
Buyers focused on a straightforward single-family purchase without an amenity requirementExcellent fit
Buyers who want a community built and sold around shared recreational amenitiesProbably not
Buyers seeking a single, uniform architectural era or consistent renovation timeline across the neighborhoodProbably not
Buyers expecting a fast, high-competition turnaround at listing given the moderate median days on marketProbably not

Data sources & freshness

Community market statsStellar MLS closed sales, 12-month windows ending September 12, 2026
Under-contract sharesStellar MLS records, as of 2026-09-08
Historical depthClosed-sale records back to 2012 (14 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.

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. 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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CallFree valuation →
Thinking of selling in Harbour Oaks Unit 1? 6 recorded closings; median 99 days on market (window ending 2026-09-12). See the Osceola County sell-now-or-wait data, what made 201,552 Florida listings fail in the last 12 months, or compare a cash offer vs. listing. Compiled from MLS records; deemed reliable but not guaranteed.

Nearby Communities

Explore more neighborhoods near Harbour Oaks with Momentum Realty’s local guides.

RPRegal Point Estates0.1 mi awayRPRegal Point0.2 mi awayHOHarbour Oaks0.2 mi awayRORegal Oak Shores0.3 mi away · median $442K, 5 sales/12 mo

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