Oak Grove East
Homes for Sale in Kissimmee, FL

Community in Kissimmee · Osceola County
118 homesBuilt 1954–2022
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Built fromLive Stellar MLS data13 years of closingsFL DOR public recordsUpdated twice daily
Live · Oak Grove East Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Ownership and context
70%
Owner-occupied · Oak Grove East
83 of 118 parcels homesteaded (FL DOR 2025)
30%
Non-owner-occupied · Oak Grove East
incl. 8% trust or LLC-held · 5% out-of-state
118
Homes in the community
118 residential parcels (FL DOR 2025)
Track record · 13 years of records
Est. 1954
Community established
homes built 1954-2022, median 1975 (FL DOR 2025)
0
Failed listings · 2023
peaked at 2 in 2006
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Oak Grove East is a small, established pocket of Kissimmee — 118 homes with a median build year of 1975 and a footprint that spans everything from mid-1950s cottages to construction as recent as 2022. That build range tells you most of what you need to know about price here: this is a condition-driven market, not a spec-sheet one. Two homes on the same street can sit far apart in value depending on roof, systems, and how much of the original 1975 stock has actually been updated.

With a homestead share around 70%, this leans owner-occupied rather than investor-churned, which tends to mean tighter inventory and homes that don't turn over casually. For a buyer, that means patience and a willingness to underwrite renovation costs. For a seller, the older median age of the housing puts a premium on documented updates — the improvements you can prove are what separate your listing from the dated comp down the block.

Best for

  • Buyers comfortable with an older home who can underwrite renovation or systems work into their budget
  • Owner-occupants seeking a compact, established neighborhood rather than a large new build
  • Value-minded buyers willing to wait for the right updated listing in a thin-inventory market

Probably not for

  • Buyers who require new construction and modern square footage
  • Investors looking for high turnover and rental churn in a heavily homesteaded pocket
  • Anyone needing move-in-ready certainty without inspecting for aging roof and systems

The market around Oak Grove East

Oak Grove East is a small community — 17 recorded sales on file, most recently in 2023 — too few for its own price trend. Here is the market around it.

Across Osceola County, 4,370 homes are active and 1,137 pending (21% under contract).

Homes here are single family residence.

ZIP and county figures describe the wider market, not Oak Grove East specifically. Momentum Research analysis of MLS records.

If we were buying in Oak Grove East 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 Oak Grove East.

Best Buy
Buyers who want an established Osceola pocket and will judge each home on condition.
Biggest Risk
The 1975 median build year means aging systems and wide variation in condition.
Sweet Spot
An updated home in the sub-1,500-square-foot range with a documented improvement history.
Avoid If
You need new construction uniformity or a large-footprint layout.

An older, small-footprint market

The median home here runs about 1,460 square feet — modest by current standards — and the median build year of 1975 means many of these houses have lived through multiple ownership cycles. The value question isn't square footage alone; it's whether the roof, HVAC, electrical, and plumbing have kept pace with the calendar. Homes built closer to 2022 exist in this community, but they're the exception against a mostly mid-century-to-1970s backbone.

Because inventory is thin at 118 homes and roughly seven in ten are homesteaded, well-updated listings tend to draw attention while dated ones sit until the price reflects the work needed. Buyers should budget for the gap between move-in-ready and project. Sellers should invest in the paperwork trail — permits, receipts, dates — because in a market this varied, proof of condition does the heavy lifting.

The location and the amenities are priced into every listing in Oak Grove East. 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 market where price hinges on condition rather than a tidy price band, our job is to read each home on its own terms — pull the permit history, weigh the systems against the 1975-era median, and tell you honestly where a listing sits between project and turnkey. That's how we keep buyers from overpaying for cosmetics and help sellers get credit for the updates that matter.

Oak Grove East in 15 seconds.

Best forBuyers who want an established Osceola pocket and will judge each home on condition.
Biggest advantageA largely owner-occupied community with tight, non-churning inventory.
Biggest riskThe 1975 median build year means aging systems and wide variation in condition.
Sweet spotAn updated home in the sub-1,500-square-foot range with a documented improvement history.
Avoid ifYou need new construction uniformity or a large-footprint layout.

HOA, CDD & Fees

In short
  • Mandatory HOA — confirm current dues
  • 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 Oak Grove East sales matched to your home.

What is your Oak Grove East home worth?

Get a no-obligation home value based on real comparable sales in Oak Grove East, 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 homes for sale in Oak Grove East on the map →

Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Oak Grove East?
The Florida DOR 2025 assessment roll shows 118 homes in Oak Grove East (public records).
What share of Oak Grove East is owner-occupied?
70% of Oak Grove East parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Oak Grove East built?
Homes in Oak Grove East were built between 1954 and 2022, with a median year built of 1975.0 (FL DOR 2025 roll).
Who is the best real estate agent for Oak Grove East?
The best agent for Oak Grove East 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 Oak Grove East.
How do I find a top Kissimmee real estate agent who knows Oak Grove East?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Oak Grove East and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Oak Grove East?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Oak Grove East purchase or sale - no call center and no pressure.
Buyers comfortable with an older home who can underwrite renovation or systems work into their budgetExcellent fit
Owner-occupants seeking a compact, established neighborhood rather than a large new buildExcellent fit
Value-minded buyers willing to wait for the right updated listing in a thin-inventory marketExcellent fit
Buyers who require new construction and modern square footageProbably not
Investors looking for high turnover and rental churn in a heavily homesteaded pocketProbably not
Anyone needing move-in-ready certainty without inspecting for aging roof and systemsProbably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (3 streets, ZIP 34744))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2013 (11 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 your area comps.

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