Oak Grove East
Homes for Sale in Kissimmee, FL
All 3,104 homes for sale in Kissimmee, FL · median $375,000 · 337 homes for sale in 34744 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, the MLS records 11 closed sales in Oak Grove East in Kissimmee, FL since 2013, the most recent in May 2026. Across Kissimmee as a whole, 2,523 homes closed in the last 12 months at a median of $387,990, 61 median days on market, with 2,928 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).
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.
Figures in this note are as of July 14, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Oak Grove EastHomes 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
A compact, largely owner-occupied enclave in Osceola County where a median living area under 1,500 square feet and a build span from 1954 to 2022 mean you're really shopping individual condition, not a uniform product.
Stellar MLS sales records identify 24 homes in Oak Grove East that have changed hands since 2005, built between 1973 and 1976 (median 1974), with a median living area of about 1,365 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.
County records show 3 qualified sales in Oak Grove East across 2024–2025 (1 in 2024, 2 in 2025), median $280,000 — 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 Grove East is best for.
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 too small for its own price trend, so here is the market around it.
In ZIP 34744, 418 homes are on the market and 21% are under contract — a steady corner of Kissimmee.
Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).
In ZIP 34744 (Kissimmee), 786 homes closed in the last 12 months at a median of $406K ($215/sq ft), up 1.3% year over year, with a median 33 days on market. Right now 128 active and 26 pending listings put supply at about 6.7 months — a balanced market. See the live ZIP 34744 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not Oak Grove East specifically. Momentum Research analysis of MLS records.
The Oak Grove East buying strategy.
If we were buying in Oak Grove East 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 Grove East.
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.
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.
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 Oak Grove East 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 Grove East sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oak Grove East, 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 Grove East home worth?
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Should you buy in Oak Grove East?
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: September 19, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-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.
Recent Developments in Oak Grove East
Development, infrastructure, retail, and school activity affecting Oak Grove East, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- 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. The developer projects thousands of jobs at full build-out.
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 5 miles northwest of Oak Grove East.
Source: Spectrum News 13 - September 2026Infrastructure
CFX holds public meetings on 14-mile toll road through part of Split Oak Forest
The Central Florida Expressway Authority held public meetings on Sept. 16 and 17 for a 14-mile road from State Road 417 near Boggy Creek Road in Orange County to Nova Road in Osceola County. CFX says portions could begin construction next year and that the road would ease traffic on Narcoossee Road. The agency faces a legal challenge from Orange County and is pursuing an eminent domain case.
What it may mean for the marketIf built, the road would add a new east-west route between Lake Nona and St. Cloud, changing commute options and access to east Orange and Osceola land. The project is about 14 miles east of Oak Grove East, elsewhere in Osceola County.
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 8 miles northwest of Oak Grove East.
Source: FOX 35 Orlando - August 2026Civic
St. Cloud council approves $6.7 million downtown apartment and parking garage agreement
The City Council unanimously approved an agreement with Atlantic Housing Partners for apartments and a parking garage next to City Hall. The Community Redevelopment Agency contributes $6.25 million and the city $460,000. The garage would hold 450 to 500 spaces, with 250 reserved for apartment residents.
What it may mean for the marketNew downtown rental housing and public parking would add residents and parking capacity to the St. Cloud core. The project is about 10 miles southeast of Oak Grove East, elsewhere in Osceola County.
Source: Spectrum News 13 - 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 10 miles northeast of Oak Grove East.
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.
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Common questions about Oak Grove East
Where is Oak Grove East?
Oak Grove East is a community in Kissimmee, Osceola County, Florida, ZIP 34744.
Are there homes for sale in Oak Grove East right now?
No active listings inside Oak Grove East at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Oak Grove East have an HOA or CDD?
No HOA is on record for Oak Grove East 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.
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| Location | Kissimmee, Osceola County, FL · ZIP 34744 |
|---|---|
| Homes in the community | 118 (FL DOR 2025 assessment roll) |
| Years built | 1954–2022 (median 1975.0) |
| Typical living area | 1,460 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 70% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2013 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Oak Grove East key facts,” movewithmomentum.com/neighborhoods/oak-grove-east, data as of September 20, 2026.
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Oak Grove East Market Scorecard
Oak Grove East is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 34744 ZIP is $385,786, about 10.6% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.